$2,999,000 Just completed and ready for immediate occupancy! Discover refined island living in this newly built coastal contemporary residence by Modus Builders, recognized as the 2025 Home of the Year. Nestled in the heart of Holmes Beach, this exceptional 4-bedroom, 3.5-bath home showcases sophisticated architecture, superior craftsmanship and an unbeatable setting only 3 blocks to the beach and 5 blocks to dining & Shopping. Constructed with exceptional attention to detail, the home features impact-rated glass, a durable metal roof and upscale finishes throughout, offering both elegance and lasting durability. Outside, enjoy your own secluded tropical oasis complete with a heated pool and spa, expansive covered lounge area and a fully equipped summer kitchen designed for effortless year-round enjoyment. The rooftop deck and upper level provide breathtaking sunrise views over the mangrove preserve along with glowing sunsets across the Gulf. Conveniently located near IMG Academy, pristine Gulf beaches, Publix and beloved local destinations including Toasted Mango Café, Duffys Tavern, Bridge Street and The Beach House, this home offers the perfect balance of luxury and accessibility. Situated within a Monthly Rental Zone, the property provides enhanced tranquility and privacy without the frequent turnover associated with weekly rental areas. This newly completed coastal sanctuary presents a rare opportunity to own in one of Holmes Beach’s most sought-after locations and enjoy the island lifestyle. 4 Beds ⋅ 4 Baths ⋅ Ilexhurst SubDv. ⋅ 34217 Zip Code Just completed and ready for immediate occupancy! Discover refined island living in this newly built coastal contemporary residence by Modus Builders, recognized as the 2025 Home of the Year. Nestled in the heart of Holmes Beach, this exceptional 4-bedroom, 3.5-bath home showcases sophisticated architecture, superior craftsmanship and an unbeatable setting only 3 blocks to the beach and 5 blocks to dining & Shopping. Constructed with exceptional attention to detail, the home features impact-rated glass, a durable metal roof and upscale finishes throughout, offering both elegance and lasting durability. Outside, enjoy your own secluded tropical oasis complete with a heated pool and spa, expansive covered lounge area and a fully equipped summer kitchen designed for effortless year-round enjoyment. The rooftop deck and upper level provide breathtaking sunrise views over the mangrove preserve along with glowing sunsets across the Gulf. Conveniently located near IMG Academy, pristine Gulf beaches, Publix and beloved local destinations including Toasted Mango Café, Duffys Tavern, Bridge Street and The Beach House, this home offers the perfect balance of luxury and accessibility. Situated within a Monthly Rental Zone, the property provides enhanced tranquility and privacy without the frequent turnover associated with weekly rental areas. This newly completed coastal sanctuary presents a rare opportunity to own in one of Holmes Beach’s most sought-after locations and enjoy the island lifestyle. 2908 Avenue B, Bradenton Beach
$1,799,000 Welcome to your island paradise, just steps from the sugary white sands of Manatee Beach, where gentle Gulf breezes and the laid-back Anna Maria Island lifestyle await. This beautifully maintained elevated concrete block home offers the perfect blend of coastal elegance, modern updates, and exceptional investment potential. The home is situated on an oversized corner lot, providing privacy and peaceful outdoor living. Featuring 3 bedrooms, 2 bathrooms, and a private elevator, this spacious home is designed for both comfortable everyday living and effortless vacation enjoyment. The open-concept floor plan is filled with natural light and centers around a large kitchen island, perfectly positioned beneath an oversized window overlooking the sparkling pool and rear deck—ideal for entertaining family and friends or enjoying an alfresco meal! The generous primary suite is a true retreat, offering a huge walk-in closet and a luxurious ensuite bath complete with a relaxing Jacuzzi soaking tub. Step outside to your private tropical oasis featuring a newly resurfaced (2022) heated saltwater pool and spa, surrounded by an elegant brick paver deck and professionally landscaped grounds. Enjoy morning coffee on the new front deck (2022) or unwind on the spacious rear deck while soaking in the peaceful island atmosphere and enjoying endless sunsets. The oversized lower level provides incredible flexibility with ample space for a home gym, game room, workshop, or additional storage. A large driveway and covered carports provide abundant parking for family and guests. Major updates include a durable metal roof installed in 2020 offering peace of mind for years to come. Inside features tray ceilings, crown molding, updated lighting and fresh paint in beachy neutral tones. Located in one of Anna Maria Island's most desirable areas, you'll love being able to stroll to Manatee Beach, restaurants, boutiques, and local entertainment. Hop aboard the free island trolley and explore everything the island has to offer—from historic Pine Avenue to Bridge Street and breathtaking Gulf sunsets. With weekly rentals permitted, this property offers outstanding flexibility as a full-time residence, vacation getaway, or income-producing investment, allowing rental income to help offset ownership expenses. Whether you're searching for your dream beach home or an exceptional island investment, this coastal retreat truly offers the best of Anna Maria Island living. 3 Beds ⋅ 2 Baths ⋅ Jones Sub SubDv. ⋅ 34217 Zip Code Welcome to your island paradise, just steps from the sugary white sands of Manatee Beach, where gentle Gulf breezes and the laid-back Anna Maria Island lifestyle await. This beautifully maintained elevated concrete block home offers the perfect blend of coastal elegance, modern updates, and exceptional investment potential. The home is situated on an oversized corner lot, providing privacy and peaceful outdoor living. Featuring 3 bedrooms, 2 bathrooms, and a private elevator, this spacious home is designed for both comfortable everyday living and effortless vacation enjoyment. The open-concept floor plan is filled with natural light and centers around a large kitchen island, perfectly positioned beneath an oversized window overlooking the sparkling pool and rear deck—ideal for entertaining family and friends or enjoying an alfresco meal! The generous primary suite is a true retreat, offering a huge walk-in closet and a luxurious ensuite bath complete with a relaxing Jacuzzi soaking tub. Step outside to your private tropical oasis featuring a newly resurfaced (2022) heated saltwater pool and spa, surrounded by an elegant brick paver deck and professionally landscaped grounds. Enjoy morning coffee on the new front deck (2022) or unwind on the spacious rear deck while soaking in the peaceful island atmosphere and enjoying endless sunsets. The oversized lower level provides incredible flexibility with ample space for a home gym, game room, workshop, or additional storage. A large driveway and covered carports provide abundant parking for family and guests. Major updates include a durable metal roof installed in 2020 offering peace of mind for years to come. Inside features tray ceilings, crown molding, updated lighting and fresh paint in beachy neutral tones. Located in one of Anna Maria Island's most desirable areas, you'll love being able to stroll to Manatee Beach, restaurants, boutiques, and local entertainment. Hop aboard the free island trolley and explore everything the island has to offer—from historic Pine Avenue to Bridge Street and breathtaking Gulf sunsets. With weekly rentals permitted, this property offers outstanding flexibility as a full-time residence, vacation getaway, or income-producing investment, allowing rental income to help offset ownership expenses. Whether you're searching for your dream beach home or an exceptional island investment, this coastal retreat truly offers the best of Anna Maria Island living. 140 50th Street, Holmes Beach
$4,000,000 Welcome to one of Anna Maria Island's most extraordinary waterfront estates, where timeless coastal elegance meets world-class boating and resort-style living. Perfectly positioned on a nearly ¼-acre corner lot with breathtaking open water frontage, this custom-built residence offers an exceptional combination of privacy, luxury, and direct access to Tampa Bay. Designed for both full-time living and luxury vacation rental potential, the home features 4 spacious en suite bedrooms, each with its own private bath. Expansive open-concept living space feature soaring ceilings, designer finishes and walls of glass capturing panoramic water views. The open kitchen has a separate butler's pantry, Thermador Appliance package and seamlessly connects indoor and outdoor living areas. Step outside to your private tropical retreat featuring a heated saltwater pool and spa, covered outdoor living spaces, and a fully equipped outdoor kitchen designed for effortless entertaining. Lush landscaping creates a tranquil island setting, while the waterfront becomes the centerpiece of the property. For boating enthusiasts, the property offers a private dock with a 20,000-pound boat lift and direct boating access to Tampa Bay and the Gulf of Mexico with no fixed bridges, making it ideal for everything from offshore fishing to sunset cruises. Take your golf cart to the white sand beaches, dining and shopping. Have peace of mind with 4 newer HVACs. This exceptional residence offers the rare opportunity to own a premier waterfront property that serves equally well as an exclusive private retreat or a high-performing luxury vacation rental. 4 Beds ⋅ 5 Baths ⋅ Sportsmans Harbor SubDv. ⋅ 34217 Zip Code Welcome to one of Anna Maria Island's most extraordinary waterfront estates, where timeless coastal elegance meets world-class boating and resort-style living. Perfectly positioned on a nearly ¼-acre corner lot with breathtaking open water frontage, this custom-built residence offers an exceptional combination of privacy, luxury, and direct access to Tampa Bay. Designed for both full-time living and luxury vacation rental potential, the home features 4 spacious en suite bedrooms, each with its own private bath. Expansive open-concept living space feature soaring ceilings, designer finishes and walls of glass capturing panoramic water views. The open kitchen has a separate butler's pantry, Thermador Appliance package and seamlessly connects indoor and outdoor living areas. Step outside to your private tropical retreat featuring a heated saltwater pool and spa, covered outdoor living spaces, and a fully equipped outdoor kitchen designed for effortless entertaining. Lush landscaping creates a tranquil island setting, while the waterfront becomes the centerpiece of the property. For boating enthusiasts, the property offers a private dock with a 20,000-pound boat lift and direct boating access to Tampa Bay and the Gulf of Mexico with no fixed bridges, making it ideal for everything from offshore fishing to sunset cruises. Take your golf cart to the white sand beaches, dining and shopping. Have peace of mind with 4 newer HVACs. This exceptional residence offers the rare opportunity to own a premier waterfront property that serves equally well as an exclusive private retreat or a high-performing luxury vacation rental. 220 N Harbor Drive, Holmes Beach
$650,000 No Storm damage or flooding from hurricanes! Beautifully updated and fully furnished, this second-floor waterfront condo in Westbay Point & Moorings is one of the few units in the community to include both a DEEDED BOAT SLIP and a PRIVATE CARPORT. Enjoy your morning coffee or evening sunsets from the west-facing enclosed lanai overlooking the canal and your boat slip. The spacious floor plan offers two large bedrooms, each with its own private bath, along with generous closet space throughout. A separate utility closet on the screened front lanai includes the stackable washer and dryer and provides extra storage. Whether you enjoy fishing from the dock, taking your golf cart around the island, or heading out by boat for a day on the Intracoastal Waterway and Tampa Bay, this condo makes it easy to enjoy the Florida lifestyle. The updated interior features granite countertops, wood-look ceramic tile flooring, modern appliances, and quality finishes throughout. Remote-controlled electric hurricane shutters on the rear lanai and accordion shutters on the front provide added protection and peace of mind. Westbay Point & Moorings is a well-maintained waterfront community with an on-site manager, low condo fees, and a quiet location in the heart of Holmes Beach. You're within walking distance of the beach, local parks, restaurants, and shopping. Whether you're looking for a full-time residence, a seasonal getaway, or an investment opportunity, this condo offers excellent flexibility. Rentals are permitted with a 30-day minimum, giving you the option to generate rental income when you're not enjoying it yourself! 2 Beds ⋅ 2 Baths ⋅ Westbay Point SubDv. ⋅ 34217 Zip Code No Storm damage or flooding from hurricanes! Beautifully updated and fully furnished, this second-floor waterfront condo in Westbay Point & Moorings is one of the few units in the community to include both a DEEDED BOAT SLIP and a PRIVATE CARPORT. Enjoy your morning coffee or evening sunsets from the west-facing enclosed lanai overlooking the canal and your boat slip. The spacious floor plan offers two large bedrooms, each with its own private bath, along with generous closet space throughout. A separate utility closet on the screened front lanai includes the stackable washer and dryer and provides extra storage. Whether you enjoy fishing from the dock, taking your golf cart around the island, or heading out by boat for a day on the Intracoastal Waterway and Tampa Bay, this condo makes it easy to enjoy the Florida lifestyle. The updated interior features granite countertops, wood-look ceramic tile flooring, modern appliances, and quality finishes throughout. Remote-controlled electric hurricane shutters on the rear lanai and accordion shutters on the front provide added protection and peace of mind. Westbay Point & Moorings is a well-maintained waterfront community with an on-site manager, low condo fees, and a quiet location in the heart of Holmes Beach. You're within walking distance of the beach, local parks, restaurants, and shopping. Whether you're looking for a full-time residence, a seasonal getaway, or an investment opportunity, this condo offers excellent flexibility. Rentals are permitted with a 30-day minimum, giving you the option to generate rental income when you're not enjoying it yourself! 6500 Flotilla Drive Unit 235, Holmes Beach
$389,000 *Vintage income producing elevated corner unit on Anna Maria Island. Vacation rentals approved* Discover the perfect blend of beach lifestyle and investment potential ideally located just a short stroll from the sugar-sand beaches of Anna Maria Island. Whether you're searching for a personal island escape, an income-producing vacation rental, or the flexibility to enjoy both, this property checks all the boxes with 7-day minimum rentals permitted. One of the standout features is the rare private covered garage, offering plenty of space for your vehicles, golf carts, bikes, beach gear, and additional storage, an amenity that's increasingly hard to find on the island. The association fee includes water, sewer, trash, exterior insurance, exterior maintenance, and reserves, making ownership simple and predictable with electricity as the only separate utility. Leave the car behind and enjoy one of the Island's most walkable locations, with the beach, restaurants, shopping, grocery store, and local bars just moments away. Clean, well maintained, and ready to enjoy from day one, this is an outstanding opportunity to own a piece of Anna Maria Island at an attractive price point with the income flexibility today's buyers are looking for. 1 Beds ⋅ 1 Baths ⋅ Palms Condominium The SubDv. ⋅ 34217 Zip Code *Vintage income producing elevated corner unit on Anna Maria Island. Vacation rentals approved* Discover the perfect blend of beach lifestyle and investment potential ideally located just a short stroll from the sugar-sand beaches of Anna Maria Island. Whether you're searching for a personal island escape, an income-producing vacation rental, or the flexibility to enjoy both, this property checks all the boxes with 7-day minimum rentals permitted. One of the standout features is the rare private covered garage, offering plenty of space for your vehicles, golf carts, bikes, beach gear, and additional storage, an amenity that's increasingly hard to find on the island. The association fee includes water, sewer, trash, exterior insurance, exterior maintenance, and reserves, making ownership simple and predictable with electricity as the only separate utility. Leave the car behind and enjoy one of the Island's most walkable locations, with the beach, restaurants, shopping, grocery store, and local bars just moments away. Clean, well maintained, and ready to enjoy from day one, this is an outstanding opportunity to own a piece of Anna Maria Island at an attractive price point with the income flexibility today's buyers are looking for. 315 58th Street Unit D, Holmes Beach
$1,250,000 Welcome to the highly sought-after Anna Maria Island Club, one of the island's premier Gulf-front communities where opportunities like this rarely become available. This beautifully maintained 2-bedroom, 2-bath condominium is being offered turnkey furnished, making it truly move-in or rental ready from day one. Currently operating as a successful active vacation rental, this property offers an exceptional opportunity for investors or those looking to own their own slice of paradise while generating income. The community allows two-week minimum rentals, providing excellent flexibility and strong rental potential in one of Florida's most desirable beach destinations. AC 2026, Roof 2026. Inside, you'll find a bright, open floor plan designed for comfortable coastal living, with everything you need already in place. Simply bring your suitcase and start enjoying the island lifestyle or continue the property's established rental success. Whether you're searching for a vacation home, an investment property, or both, this is your chance to own in the prestigious Anna Maria Island Club, a community where listings are few and demand remains high. 2 Beds ⋅ 2 Baths ⋅ Anna Maria Island Club SubDv. ⋅ 34217 Zip Code Welcome to the highly sought-after Anna Maria Island Club, one of the island's premier Gulf-front communities where opportunities like this rarely become available. This beautifully maintained 2-bedroom, 2-bath condominium is being offered turnkey furnished, making it truly move-in or rental ready from day one. Currently operating as a successful active vacation rental, this property offers an exceptional opportunity for investors or those looking to own their own slice of paradise while generating income. The community allows two-week minimum rentals, providing excellent flexibility and strong rental potential in one of Florida's most desirable beach destinations. AC 2026, Roof 2026. Inside, you'll find a bright, open floor plan designed for comfortable coastal living, with everything you need already in place. Simply bring your suitcase and start enjoying the island lifestyle or continue the property's established rental success. Whether you're searching for a vacation home, an investment property, or both, this is your chance to own in the prestigious Anna Maria Island Club, a community where listings are few and demand remains high. 2600 Gulf Drive N Unit 12, Bradenton Beach
$1,199,000 Wake up to Gulf breezes, stroll across the street to the sugar-white sands and turquoise waters of Anna Maria Island, and end each day watching spectacular sunsets from your private wraparound deck with partial Gulf views. This beautifully updated and fully furnished three-bedroom, two-bath home with two car garage offers the ultimate island lifestyle while allowing weekly rentals, creating an exceptional opportunity for both personal enjoyment and investment income. With an elevated home and hurricane windows and sliding glass doors, you'll feel relaxed and worry-free. One of the community's most desirable residences, this property features the largest lot in the neighborhood, offering nearly twice the yard space of neighboring units along with an expansive outdoor living area, covered patio, garage, laundry, and abundant storage. Inside, the light-filled open floor plan is designed for effortless coastal living, featuring a beautifully updated kitchen that flows seamlessly into the living and dining areas, while the spacious primary suite offers a stunning renovated walk-in shower. Upstairs, a charming loft connects two guest bedrooms and a full bath, providing comfortable accommodations for family and guests. Recent improvements include a new roof, fresh exterior paint, updated wraparound deck, new washer and dryer, new lighting fixtures, and stylish new furnishings, allowing the next owner to begin enjoying or renting the property immediately. Just steps from the heated community pool, beach access, restaurants, shopping, and everything Holmes Beach and Anna Maria Island have to offer, this turnkey residence presents a rare opportunity to own one of the community's premier properties. With weekly rentals permitted and excellent income potential, this is Florida beach living at its finest. 3 Beds ⋅ 2 Baths ⋅ Holmes Beach SubDv. ⋅ 34217 Zip Code Wake up to Gulf breezes, stroll across the street to the sugar-white sands and turquoise waters of Anna Maria Island, and end each day watching spectacular sunsets from your private wraparound deck with partial Gulf views. This beautifully updated and fully furnished three-bedroom, two-bath home with two car garage offers the ultimate island lifestyle while allowing weekly rentals, creating an exceptional opportunity for both personal enjoyment and investment income. With an elevated home and hurricane windows and sliding glass doors, you'll feel relaxed and worry-free. One of the community's most desirable residences, this property features the largest lot in the neighborhood, offering nearly twice the yard space of neighboring units along with an expansive outdoor living area, covered patio, garage, laundry, and abundant storage. Inside, the light-filled open floor plan is designed for effortless coastal living, featuring a beautifully updated kitchen that flows seamlessly into the living and dining areas, while the spacious primary suite offers a stunning renovated walk-in shower. Upstairs, a charming loft connects two guest bedrooms and a full bath, providing comfortable accommodations for family and guests. Recent improvements include a new roof, fresh exterior paint, updated wraparound deck, new washer and dryer, new lighting fixtures, and stylish new furnishings, allowing the next owner to begin enjoying or renting the property immediately. Just steps from the heated community pool, beach access, restaurants, shopping, and everything Holmes Beach and Anna Maria Island have to offer, this turnkey residence presents a rare opportunity to own one of the community's premier properties. With weekly rentals permitted and excellent income potential, this is Florida beach living at its finest. 6327 Gulf Drive, Holmes Beach
$5,495,000 Imagine waking to the gentle lap of the Intracoastal Waterway just beyond your windows, where 240 feet of prime waterfront unfolds into sweeping panoramic vistas that stretch across the bay. This architecturally stunning custom residence has uncompromising attention to detail, commands one of Holmes Beach’s most coveted bayfront settings — a true waterfront sanctuary on Anna Maria Island’s serene shores. Spanning 4,007 square feet under air with 4 bedrooms and 4.5 bathrooms, this home is a masterclass in coastal luxury living. Sun-drenched interiors flow effortlessly to expansive outdoor realms, where a beach-entry pool beckons for effortless days of swimming and lounging beneath Florida’s endless blue skies. Two private docks and two boat lifts put you seconds from open water — perfect for spontaneous sunset cruises, fishing excursions, or simply watching dolphins play against the horizon. Step inside and discover thoughtfully designed living spaces that embrace the views from nearly every room. A dedicated mother-in-law suite offers privacy and comfort for extended family or guests, while the generous 3-car garage ensures ample room for vehicles, toys, and beach gear. Just a short, leisurely walk to the Gulf of Mexico’s sugar-sand beaches, this location delivers the ultimate island lifestyle: effortless access to world-class shelling, dining, and the laid-back charm that defines Anna Maria Island. Whether entertaining on the waterfront terraces, retreating to the poolside oasis, or simply savoring quiet mornings with coffee overlooking the water, this home captures the essence of elevated coastal living. Rare, refined, and ready for its next chapter — this is island living at its absolute finest. 4 Beds ⋅ 5 Baths ⋅ Sunrise Park SubDv. ⋅ 34217 Zip Code Imagine waking to the gentle lap of the Intracoastal Waterway just beyond your windows, where 240 feet of prime waterfront unfolds into sweeping panoramic vistas that stretch across the bay. This architecturally stunning custom residence has uncompromising attention to detail, commands one of Holmes Beach’s most coveted bayfront settings — a true waterfront sanctuary on Anna Maria Island’s serene shores. Spanning 4,007 square feet under air with 4 bedrooms and 4.5 bathrooms, this home is a masterclass in coastal luxury living. Sun-drenched interiors flow effortlessly to expansive outdoor realms, where a beach-entry pool beckons for effortless days of swimming and lounging beneath Florida’s endless blue skies. Two private docks and two boat lifts put you seconds from open water — perfect for spontaneous sunset cruises, fishing excursions, or simply watching dolphins play against the horizon. Step inside and discover thoughtfully designed living spaces that embrace the views from nearly every room. A dedicated mother-in-law suite offers privacy and comfort for extended family or guests, while the generous 3-car garage ensures ample room for vehicles, toys, and beach gear. Just a short, leisurely walk to the Gulf of Mexico’s sugar-sand beaches, this location delivers the ultimate island lifestyle: effortless access to world-class shelling, dining, and the laid-back charm that defines Anna Maria Island. Whether entertaining on the waterfront terraces, retreating to the poolside oasis, or simply savoring quiet mornings with coffee overlooking the water, this home captures the essence of elevated coastal living. Rare, refined, and ready for its next chapter — this is island living at its absolute finest. 522 Bayview Drive, Holmes Beach
$1,050,000 ***UNBELIEVABLE BRADENTON BEACH VALUE***Imagine waking up just 100 steps from the pristine white-sand beaches of Bradenton Beach on the Gulf of Mexico and ending each day with spectacular Gulf sunsets. Located directly across the street from the beach in the highly sought-after Bermuda Bay Club, this beautifully maintained, Key West-style townhouse offers 2 bedrooms, 2.5 baths, a rare private elevator and oversized 2-3 tandem car garage, water views, and weekly rentals permitted, making it the perfect island getaway, full-time residence, or investment property. The main living level features an open-concept floor plan with a bright family room, dining area, eat-in kitchen with brand-new stainless-steel appliances, guest half bath, and laundry. Step outside to the large Trex-deck balcony and enjoy refreshing coastal breezes along with views of both the Intracoastal Bay and the turquoise waters of the Gulf of Mexico. Recently installed hurricane-impact windows and doors provide peace of mind, energy efficiency, and abundant natural light throughout. Upstairs, you'll find two spacious ensuite bedrooms, each with walk-in closets. The primary suite features a private balcony with water views, creating the perfect place to unwind after a day in the sun. The guest suite offers comfortable accommodations for family and friends, making this property ideal as a personal retreat or income-producing vacation rental. A rare feature for island living, the oversized tandem garage offering plenty of room for vehicles, beach gear, bicycles, kayaks, paddleboards, and even a golf cart. An outdoor shower and rear deck make rinsing off after a day at the beach easy and convenient, while the private elevator provides effortless access to all levels of the home. Bermuda Bay Club offers resort-style amenities including a heated pool and spa, grilling area, and a private boardwalk through the mangroves where you can enjoy watching dolphins, pelicans, and other native wildlife along the Intracoastal Waterway. Perfectly positioned between the Gulf and the Bay, this exceptional property is within walking distance of the popular Historic Bridge Street with restaurants, shopping, bars, and plenty of entertainment. The free Anna Maria Island Trolley stops directly in front of the community, providing convenient access to the entire island without ever needing a car. Start your mornings with a walk along the beach, spend your afternoons by the pool or exploring the island, and end your evenings enjoying breathtaking Florida sunsets Whether you're seeking a full-time residence, vacation getaway, or investment property, Bermuda Bay Club offers weekly rentals permitted, lower condo fees, resort-style amenities, and one of the most desirable locations on Anna Maria Island. Opportunities to own a property with a private elevator, tandem garage, stunning water views, and beach access within 100ft to the Gulf and 50ft to the Bay are rare! Don't Just Dream It... Live It and start living your own Florida Paradise today! 2 Beds ⋅ 3 Baths ⋅ Bermuda Bay Club SubDv. ⋅ 34217 Zip Code ***UNBELIEVABLE BRADENTON BEACH VALUE***Imagine waking up just 100 steps from the pristine white-sand beaches of Bradenton Beach on the Gulf of Mexico and ending each day with spectacular Gulf sunsets. Located directly across the street from the beach in the highly sought-after Bermuda Bay Club, this beautifully maintained, Key West-style townhouse offers 2 bedrooms, 2.5 baths, a rare private elevator and oversized 2-3 tandem car garage, water views, and weekly rentals permitted, making it the perfect island getaway, full-time residence, or investment property. The main living level features an open-concept floor plan with a bright family room, dining area, eat-in kitchen with brand-new stainless-steel appliances, guest half bath, and laundry. Step outside to the large Trex-deck balcony and enjoy refreshing coastal breezes along with views of both the Intracoastal Bay and the turquoise waters of the Gulf of Mexico. Recently installed hurricane-impact windows and doors provide peace of mind, energy efficiency, and abundant natural light throughout. Upstairs, you'll find two spacious ensuite bedrooms, each with walk-in closets. The primary suite features a private balcony with water views, creating the perfect place to unwind after a day in the sun. The guest suite offers comfortable accommodations for family and friends, making this property ideal as a personal retreat or income-producing vacation rental. A rare feature for island living, the oversized tandem garage offering plenty of room for vehicles, beach gear, bicycles, kayaks, paddleboards, and even a golf cart. An outdoor shower and rear deck make rinsing off after a day at the beach easy and convenient, while the private elevator provides effortless access to all levels of the home. Bermuda Bay Club offers resort-style amenities including a heated pool and spa, grilling area, and a private boardwalk through the mangroves where you can enjoy watching dolphins, pelicans, and other native wildlife along the Intracoastal Waterway. Perfectly positioned between the Gulf and the Bay, this exceptional property is within walking distance of the popular Historic Bridge Street with restaurants, shopping, bars, and plenty of entertainment. The free Anna Maria Island Trolley stops directly in front of the community, providing convenient access to the entire island without ever needing a car. Start your mornings with a walk along the beach, spend your afternoons by the pool or exploring the island, and end your evenings enjoying breathtaking Florida sunsets Whether you're seeking a full-time residence, vacation getaway, or investment property, Bermuda Bay Club offers weekly rentals permitted, lower condo fees, resort-style amenities, and one of the most desirable locations on Anna Maria Island. Opportunities to own a property with a private elevator, tandem garage, stunning water views, and beach access within 100ft to the Gulf and 50ft to the Bay are rare! Don't Just Dream It... Live It and start living your own Florida Paradise today! 1469 Gulf Drive N, Bradenton Beach
$4,250,000 Located in the heart of Holmes Beach on Anna Maria Island, this reimagined waterfront home offers deep-water boating access, direct Gulf views, elevator access, and a beach location that is hard to beat, just steps from the front door to the sand. Set on one of the closest canal-front streets to the beach, the property provides protected dockage, quick access to Tampa Bay, downtown St. Petersburg, and the Gulf of Mexico, along with the everyday ease of true island living. Originally rebuilt from the block in 2022 in collaboration with Richard Haas, the home was thoughtfully redesigned with clean architectural lines, quality coastal construction, and low-maintenance ownership in mind. The result is a modern Anna Maria Island waterfront residence built for comfort, efficiency, and long-term durability without sacrificing style, function, or quality. Inside, the living spaces were designed to maximize natural light and keep water views connected to daily life. The main living area, kitchen, and secondary primary suite all capture direct Gulf views, while large glass openings connect the interior spaces to the outdoor terraces. A custom floating red oak staircase serves as a striking architectural focal point and adds warmth to the clean modern design. The kitchen was designed for both entertaining and everyday use, featuring Cosentino Quartz counters, custom full-height cabinetry, JennAir Professional appliances, and a walk-in pantry. More than fifteen slabs of quartz were incorporated throughout the kitchen and bedroom suites, creating a consistent level of finish throughout the home. Smart-home features, remote-controlled shades, custom lighting, elevator access, and thoughtfully curated finishes contribute to a comfortable and efficient living environment. The primary suite offers a private retreat with a custom-built walk-in closet and a spa-inspired bath featuring Toto fixtures, dual vanities, and multi-function shower features. Additional upgrades include dual high-efficiency HVAC systems, buried gas storage, generator readiness, tankless water heaters, and water-softening systems. A newly installed dock and Golden boat lift accommodate larger vessels, while recent dredging improves canal access for serious boaters. Combining modern coastal architecture, deep-water boating access, Gulf views, updated construction, and one of the most walkable beach locations on Anna Maria Island, this Holmes Beach waterfront residence represents a rare opportunity within Florida's luxury coastal market. Easy access to North bridge/Manatee Ave via two different routes. Please note: A pool permit has been approved. Pool plans, specifications, and contractor quote are available in the attachments. 5 Beds ⋅ 4 Baths ⋅ Sportsmans Harbor SubDv. ⋅ 34217 Zip Code Located in the heart of Holmes Beach on Anna Maria Island, this reimagined waterfront home offers deep-water boating access, direct Gulf views, elevator access, and a beach location that is hard to beat, just steps from the front door to the sand. Set on one of the closest canal-front streets to the beach, the property provides protected dockage, quick access to Tampa Bay, downtown St. Petersburg, and the Gulf of Mexico, along with the everyday ease of true island living. Originally rebuilt from the block in 2022 in collaboration with Richard Haas, the home was thoughtfully redesigned with clean architectural lines, quality coastal construction, and low-maintenance ownership in mind. The result is a modern Anna Maria Island waterfront residence built for comfort, efficiency, and long-term durability without sacrificing style, function, or quality. Inside, the living spaces were designed to maximize natural light and keep water views connected to daily life. The main living area, kitchen, and secondary primary suite all capture direct Gulf views, while large glass openings connect the interior spaces to the outdoor terraces. A custom floating red oak staircase serves as a striking architectural focal point and adds warmth to the clean modern design. The kitchen was designed for both entertaining and everyday use, featuring Cosentino Quartz counters, custom full-height cabinetry, JennAir Professional appliances, and a walk-in pantry. More than fifteen slabs of quartz were incorporated throughout the kitchen and bedroom suites, creating a consistent level of finish throughout the home. Smart-home features, remote-controlled shades, custom lighting, elevator access, and thoughtfully curated finishes contribute to a comfortable and efficient living environment. The primary suite offers a private retreat with a custom-built walk-in closet and a spa-inspired bath featuring Toto fixtures, dual vanities, and multi-function shower features. Additional upgrades include dual high-efficiency HVAC systems, buried gas storage, generator readiness, tankless water heaters, and water-softening systems. A newly installed dock and Golden boat lift accommodate larger vessels, while recent dredging improves canal access for serious boaters. Combining modern coastal architecture, deep-water boating access, Gulf views, updated construction, and one of the most walkable beach locations on Anna Maria Island, this Holmes Beach waterfront residence represents a rare opportunity within Florida's luxury coastal market. Easy access to North bridge/Manatee Ave via two different routes. Please note: A pool permit has been approved. Pool plans, specifications, and contractor quote are available in the attachments. 201 N Harbor Drive, Holmes Beach
$4,295,000 Discover coastal elegance at its finest in this stunning 4-bedroom, 4.5-bathroom waterfront home in the heart of Holmes Beach. Designed for both relaxed island living and effortless entertaining, this boater’s dream residence sits directly on the canal with breathtaking views of the bay and spectacular sunrise vistas that greet you each morning. Step outside to your private waterfront oasis featuring a heated, uniquely shaped triangle pool. The property offers two robust boat lifts, one 7,500 lb and the other is a 39ft slip with a 20,000 lb making it ideal for everything from a center console to a larger cruising vessel. Multiple balconies and upper deck invite you to unwind with the gentle bay breeze, while lush tropical landscaping provides privacy and a serene, resort-like atmosphere. Inside, the chef’s kitchen shines with high-end appliances, wine fridge, farm sink, gas burner and thoughtful design, making it a joy for culinary enthusiasts. Hurricane-rated impact windows and sliders throughout offer peace of mind and seamless indoor-outdoor flow. A spacious single car garage with storage for toys and beach gear. This home perfectly blends luxury and functionality—elevated finishes, generous living spaces, and that enviable waterfront lifestyle Anna Maria Island is known for. Whether you’re watching dolphins cruise by, hosting sunset gatherings, or simply enjoying the privacy of your canal-front sanctuary, every day feels like a vacation. A rare opportunity to own a true boater’s paradise in one of Florida’s most sought-after beach communities. Schedule your private showing today and experience coastal living at its best. 4 Beds ⋅ 5 Baths ⋅ Holmes Beach SubDv. ⋅ 34217 Zip Code Discover coastal elegance at its finest in this stunning 4-bedroom, 4.5-bathroom waterfront home in the heart of Holmes Beach. Designed for both relaxed island living and effortless entertaining, this boater’s dream residence sits directly on the canal with breathtaking views of the bay and spectacular sunrise vistas that greet you each morning. Step outside to your private waterfront oasis featuring a heated, uniquely shaped triangle pool. The property offers two robust boat lifts, one 7,500 lb and the other is a 39ft slip with a 20,000 lb making it ideal for everything from a center console to a larger cruising vessel. Multiple balconies and upper deck invite you to unwind with the gentle bay breeze, while lush tropical landscaping provides privacy and a serene, resort-like atmosphere. Inside, the chef’s kitchen shines with high-end appliances, wine fridge, farm sink, gas burner and thoughtful design, making it a joy for culinary enthusiasts. Hurricane-rated impact windows and sliders throughout offer peace of mind and seamless indoor-outdoor flow. A spacious single car garage with storage for toys and beach gear. This home perfectly blends luxury and functionality—elevated finishes, generous living spaces, and that enviable waterfront lifestyle Anna Maria Island is known for. Whether you’re watching dolphins cruise by, hosting sunset gatherings, or simply enjoying the privacy of your canal-front sanctuary, every day feels like a vacation. A rare opportunity to own a true boater’s paradise in one of Florida’s most sought-after beach communities. Schedule your private showing today and experience coastal living at its best. 511 59th Street, Bradenton Beach
$3,899,000 This fully remodeled 3-bedroom, 3.5-bath waterfront home is a rare find—offering breathtaking views, modern upgrades throughout, and direct access to Tampa Bay and the Gulf of Mexico in the highly sought after neighborhood of Key Royale on Anna Maria Island. Situated on a tranquil south-facing cove along the Intracoastal Waterway, this property provides both stunning scenery and natural protection. Upon entering the home, you will find an open, airy floor plan featuring all-new wood flooring, new interior and exterior doors, new windows with shutters, and exceptional craftsmanship at every turn. The chef’s kitchen is a true showstopper, showcasing top-of-the-line Thermador appliances, custom cabinetry, and a spacious layout designed for effortless hosting and everyday living. The primary suite is a retreat of its own with large walk -in closet and a beautifully updated ensuite bath. The second bedroom functions like a second primary, offering a generous bedroom space and its own private ensuite bathroom—ideal for guests or multi-generational living. Outdoors, the home transforms into a private waterfront paradise. Enjoy a saltwater pool and spa, an outdoor kitchen with a gas BBQ, green egg, griddle, and your own putting green—all overlooking sparkling water views where dolphins are frequent visitors. Boaters will appreciate the 16,000-lb boat lift, deep water access, and plenty of side-yard space for additional toys, including a 50-amp RV hookup and room for a boat or trailer. Additional peace of mind comes with recent updates: the lanai was screened in March 2026, and a full home inspection was completed in January 2026 by SWF Home Inspections. With luxury updates, protected water, and unparalleled views, this is Florida waterfront living at its finest! 3 Beds ⋅ 4 Baths ⋅ Key Royale SubDv. ⋅ 34217 Zip Code This fully remodeled 3-bedroom, 3.5-bath waterfront home is a rare find—offering breathtaking views, modern upgrades throughout, and direct access to Tampa Bay and the Gulf of Mexico in the highly sought after neighborhood of Key Royale on Anna Maria Island. Situated on a tranquil south-facing cove along the Intracoastal Waterway, this property provides both stunning scenery and natural protection. Upon entering the home, you will find an open, airy floor plan featuring all-new wood flooring, new interior and exterior doors, new windows with shutters, and exceptional craftsmanship at every turn. The chef’s kitchen is a true showstopper, showcasing top-of-the-line Thermador appliances, custom cabinetry, and a spacious layout designed for effortless hosting and everyday living. The primary suite is a retreat of its own with large walk -in closet and a beautifully updated ensuite bath. The second bedroom functions like a second primary, offering a generous bedroom space and its own private ensuite bathroom—ideal for guests or multi-generational living. Outdoors, the home transforms into a private waterfront paradise. Enjoy a saltwater pool and spa, an outdoor kitchen with a gas BBQ, green egg, griddle, and your own putting green—all overlooking sparkling water views where dolphins are frequent visitors. Boaters will appreciate the 16,000-lb boat lift, deep water access, and plenty of side-yard space for additional toys, including a 50-amp RV hookup and room for a boat or trailer. Additional peace of mind comes with recent updates: the lanai was screened in March 2026, and a full home inspection was completed in January 2026 by SWF Home Inspections. With luxury updates, protected water, and unparalleled views, this is Florida waterfront living at its finest! 605 Key Royale Drive, Holmes Beach
$2,995,000 Experience the ultimate island lifestyle in this exquisite coastal retreat on Anna Maria Island. Nestled on one of the island’s most breathtaking tropical lots, this beautifully updated four-bedroom, three-and-a-half-bath residence offers deepwater canal access to the Gulf and the perfect blend of luxury, comfort, and waterfront living. Sold fully furnished and including a golf cart for added convenience, the home underwent an extensive remodel in 2021 and has been thoughtfully upgraded throughout. Recent improvements include a new seawall and dock with a 10,000-pound boat lift upgraded in 2024, as well as a whole-house propane generator installed in 2026. The property has also had no flood damage. Inside, expansive wood-look plank tile flooring creates a warm and inviting atmosphere throughout the home. The stunning chef’s kitchen features quartz countertops, custom cabinetry, and premium high-end appliances. The main living level includes three spacious guest bedrooms, while the entire upper level is dedicated to a luxurious primary suite complete with dual vanities, a spa-inspired bathroom, and an oversized walk-in closet with washer/dryer. Additional highlights include a 200-square-foot insulated storage attic, a private man cave, and a unique indoor entertainment space featuring an indoor grill, bar, and television area that flows seamlessly to the resort-style pool and outdoor living space. From your private dock, enjoy direct boating access to nearby beaches, waterfront dining, and all the charm that island living has to give. This exceptional property is a rare opportunity to own a true waterfront paradise on one of Florida’s most sought-after islands. Don’t miss your chance to make this dream home your reality. 4 Beds ⋅ 4 Baths ⋅ Bay Palms SubDv. ⋅ 34217 Zip Code Experience the ultimate island lifestyle in this exquisite coastal retreat on Anna Maria Island. Nestled on one of the island’s most breathtaking tropical lots, this beautifully updated four-bedroom, three-and-a-half-bath residence offers deepwater canal access to the Gulf and the perfect blend of luxury, comfort, and waterfront living. Sold fully furnished and including a golf cart for added convenience, the home underwent an extensive remodel in 2021 and has been thoughtfully upgraded throughout. Recent improvements include a new seawall and dock with a 10,000-pound boat lift upgraded in 2024, as well as a whole-house propane generator installed in 2026. The property has also had no flood damage. Inside, expansive wood-look plank tile flooring creates a warm and inviting atmosphere throughout the home. The stunning chef’s kitchen features quartz countertops, custom cabinetry, and premium high-end appliances. The main living level includes three spacious guest bedrooms, while the entire upper level is dedicated to a luxurious primary suite complete with dual vanities, a spa-inspired bathroom, and an oversized walk-in closet with washer/dryer. Additional highlights include a 200-square-foot insulated storage attic, a private man cave, and a unique indoor entertainment space featuring an indoor grill, bar, and television area that flows seamlessly to the resort-style pool and outdoor living space. From your private dock, enjoy direct boating access to nearby beaches, waterfront dining, and all the charm that island living has to give. This exceptional property is a rare opportunity to own a true waterfront paradise on one of Florida’s most sought-after islands. Don’t miss your chance to make this dream home your reality. 522 68th Street, Holmes Beach
$1,900,000 Stunning Key West style home only 2 blocks away from the sugar sands and turquoise waters of the Gulf beaches, this beautifully maintained 4-bedroom, 3.5-bath residence offers the ideal blend of island charm, comfort, and coastal living. Lovingly owner-occupied and meticulously cared for, the home showcases pride of ownership throughout. Spacious living areas and multiple balconies invite you to unwind with your morning coffee while enjoying the refreshing Gulf breeze. Catch the Osprey sightings from the top balcony! Open concept living, kitchen and dining that is perfect for entertaining and family fun. Fabulous features throughout consist of stainless steel appliances, granite counter tops, tile and bamboo flooring for easy clean up, large walk-in showers, soaking tub and more. Very ideal is there are 2 primary suites, one on the main level and one on the upper level. 2 car garage and even more driveway parking for ultimate convenience. 2 a/c units (replaced in 2023). Opportunities are endless as this home would make a great primary, seasonal or investment property. Step outside to your private tropical retreat featuring a heated pool surrounded by lush landscaping, creating the perfect setting for relaxing afternoons or entertaining guests year-round. Located in the heart of Holmes Beach’s most desirable areas, you’re just moments from the beach, local dining, boutique shopping, and everything island life has to offer! 4 Beds ⋅ 4 Baths ⋅ Anna Maria Island Beachwalk SubDv. ⋅ 34217 Zip Code Stunning Key West style home only 2 blocks away from the sugar sands and turquoise waters of the Gulf beaches, this beautifully maintained 4-bedroom, 3.5-bath residence offers the ideal blend of island charm, comfort, and coastal living. Lovingly owner-occupied and meticulously cared for, the home showcases pride of ownership throughout. Spacious living areas and multiple balconies invite you to unwind with your morning coffee while enjoying the refreshing Gulf breeze. Catch the Osprey sightings from the top balcony! Open concept living, kitchen and dining that is perfect for entertaining and family fun. Fabulous features throughout consist of stainless steel appliances, granite counter tops, tile and bamboo flooring for easy clean up, large walk-in showers, soaking tub and more. Very ideal is there are 2 primary suites, one on the main level and one on the upper level. 2 car garage and even more driveway parking for ultimate convenience. 2 a/c units (replaced in 2023). Opportunities are endless as this home would make a great primary, seasonal or investment property. Step outside to your private tropical retreat featuring a heated pool surrounded by lush landscaping, creating the perfect setting for relaxing afternoons or entertaining guests year-round. Located in the heart of Holmes Beach’s most desirable areas, you’re just moments from the beach, local dining, boutique shopping, and everything island life has to offer! 309 68th Street, Holmes Beach
$3,500,000 Virtually Staged. Imagine arriving at a private estate tucked along the shimmering waters of Tampa Bay on Anna Maria Island, where 235 feet of pristine waterfront create a rare sense of space, privacy and uninterrupted views. This four-bedroom, six-bath coastal residence in Holmes Beach is designed to capture the beauty of the bay from nearly every angle. Expansive walls of glass and sliding doors frame panoramic water vistas, filling the home with natural light and bringing the outdoors in, a hallmark of luxury waterfront homes in this area. Inside, the home blends refined elegance with relaxed island living. A grand open-concept layout connects the living room, dining area and a chef’s kitchen outfitted with high-end appliances, custom cabinetry and generous entertaining space. Multiple living areas, often found in premier Anna Maria Island homes, offer flexibility for hosting guests or enjoying quiet retreats. Each of the four bedrooms is generously sized, while the six total baths provide a resort-style convenience ideal for family and guests. The primary suite is typically a sanctuary of its own, featuring water views, private balcony access and a spa-inspired bath. Outside, the property becomes exceptional. A resort-style pool and spa overlook the bay, surrounded by lush tropical landscaping and expansive outdoor living areas designed for entertaining or unwinding in the coastal breeze. Waterfront homes here often emphasize seamless indoor-outdoor flow, creating an island lifestyle experience. With 235 feet of frontage, the property offers a private dock and boat lift, ideal for direct access to the open waters of Tampa Bay and the Gulf beyond. Whether you’re setting out for a sunset cruise, fishing at dawn or simply watching dolphins and manatees pass by, the water becomes an extension of daily life. Set on one of the desirable stretches of Anna Maria Island, this home combines rare waterfront scale, luxury amenities and effortless boating access, a showcase of elevated coastal living. 4 Beds ⋅ 6 Baths ⋅ Holmes Beach SubDv. ⋅ 34217 Zip Code Virtually Staged. Imagine arriving at a private estate tucked along the shimmering waters of Tampa Bay on Anna Maria Island, where 235 feet of pristine waterfront create a rare sense of space, privacy and uninterrupted views. This four-bedroom, six-bath coastal residence in Holmes Beach is designed to capture the beauty of the bay from nearly every angle. Expansive walls of glass and sliding doors frame panoramic water vistas, filling the home with natural light and bringing the outdoors in, a hallmark of luxury waterfront homes in this area. Inside, the home blends refined elegance with relaxed island living. A grand open-concept layout connects the living room, dining area and a chef’s kitchen outfitted with high-end appliances, custom cabinetry and generous entertaining space. Multiple living areas, often found in premier Anna Maria Island homes, offer flexibility for hosting guests or enjoying quiet retreats. Each of the four bedrooms is generously sized, while the six total baths provide a resort-style convenience ideal for family and guests. The primary suite is typically a sanctuary of its own, featuring water views, private balcony access and a spa-inspired bath. Outside, the property becomes exceptional. A resort-style pool and spa overlook the bay, surrounded by lush tropical landscaping and expansive outdoor living areas designed for entertaining or unwinding in the coastal breeze. Waterfront homes here often emphasize seamless indoor-outdoor flow, creating an island lifestyle experience. With 235 feet of frontage, the property offers a private dock and boat lift, ideal for direct access to the open waters of Tampa Bay and the Gulf beyond. Whether you’re setting out for a sunset cruise, fishing at dawn or simply watching dolphins and manatees pass by, the water becomes an extension of daily life. Set on one of the desirable stretches of Anna Maria Island, this home combines rare waterfront scale, luxury amenities and effortless boating access, a showcase of elevated coastal living. 518 58th Street, Holmes Beach
$4,499,000 This full duplex offering delivers a unique chance to own a large-scale coastal asset in a highly desirable vacation rental market. Consisting of two separate residences with a combined total of 8 bedrooms and 7 bathrooms, the property is well-suited for maximizing guest capacity, multi-generational travel demand, and premium rental appeal. Designed with entertaining in mind, both residences feature spacious open-concept layouts, vaulted ceilings with beam accents, multiple covered balconies with Gulf-to-Bay views, and private elevators providing seamless access throughout each home. The kitchens are finished with solid wood cabinetry and granite countertops, while the bedroom layouts prioritize comfort and privacy with en-suite bathrooms and walk-in closets. The outdoor living experience was built for the vacation lifestyle, centered around a private pool area with covered lounging and dining spaces, plus a waterfall feature that enhances the resort-style atmosphere guests are drawn to. With the ability to accommodate daily or weekly rentals and a location just moments from the beach, bay, Bridge Street, restaurants, shopping, and trolley access, this property offers the kind of combination investors consistently search for: strong location appeal, high guest functionality, and exceptional income-producing potential. 8 Beds ⋅ 8 Baths ⋅ Cortez Beach SubDv. ⋅ 34217 Zip Code This full duplex offering delivers a unique chance to own a large-scale coastal asset in a highly desirable vacation rental market. Consisting of two separate residences with a combined total of 8 bedrooms and 7 bathrooms, the property is well-suited for maximizing guest capacity, multi-generational travel demand, and premium rental appeal. Designed with entertaining in mind, both residences feature spacious open-concept layouts, vaulted ceilings with beam accents, multiple covered balconies with Gulf-to-Bay views, and private elevators providing seamless access throughout each home. The kitchens are finished with solid wood cabinetry and granite countertops, while the bedroom layouts prioritize comfort and privacy with en-suite bathrooms and walk-in closets. The outdoor living experience was built for the vacation lifestyle, centered around a private pool area with covered lounging and dining spaces, plus a waterfall feature that enhances the resort-style atmosphere guests are drawn to. With the ability to accommodate daily or weekly rentals and a location just moments from the beach, bay, Bridge Street, restaurants, shopping, and trolley access, this property offers the kind of combination investors consistently search for: strong location appeal, high guest functionality, and exceptional income-producing potential. 105 4th Street S, Bradenton Beach
$985,000 DEEDED BOAT SLIP and ROOM FOR A POOL! Discover the best of island living in beautiful Holmes Beach. Nestled on a quiet street in a peaceful neighborhood, you’ll love the combination of boating access and close proximity to the beach this home has to offer. Elevated with impact windows, this 2-bedroom, 2-bathroom home is turnkey furnished and includes a deeded, unimproved boat slip at the end of 85th Street, perfect for boating enthusiasts and those seeking the ultimate coastal lifestyle. NEW ROOF installed in August 2025. The downstairs area has been professionally remediated and renovated, while the upstairs living area remained untouched by hurricanes in 2024. Situated on an expansive 9,000sqft lot, there is ample space to add a pool and create your own private oasis. Whether you’re seeking a primary residence or a tropical getaway, this property is ideal for enjoying Anna Maria Island living. Book your showing today! 2 Beds ⋅ 2 Baths ⋅ Holmes Beach SubDv. ⋅ 34217 Zip Code DEEDED BOAT SLIP and ROOM FOR A POOL! Discover the best of island living in beautiful Holmes Beach. Nestled on a quiet street in a peaceful neighborhood, you’ll love the combination of boating access and close proximity to the beach this home has to offer. Elevated with impact windows, this 2-bedroom, 2-bathroom home is turnkey furnished and includes a deeded, unimproved boat slip at the end of 85th Street, perfect for boating enthusiasts and those seeking the ultimate coastal lifestyle. NEW ROOF installed in August 2025. The downstairs area has been professionally remediated and renovated, while the upstairs living area remained untouched by hurricanes in 2024. Situated on an expansive 9,000sqft lot, there is ample space to add a pool and create your own private oasis. Whether you’re seeking a primary residence or a tropical getaway, this property is ideal for enjoying Anna Maria Island living. Book your showing today! 221 85th Street, Holmes Beach
$2,695,000 Perfectly positioned in the middle of the Gulf and the Intercostal, you get the best of both worlds! This 4 bedroom, 3 bathroom pool home is 2,678 sq ft and decorated in fun beachy decor. Offering incredible views in every direction because it’s situated in the best location on the entire island! The island is only 150 yards wide where this 3-story condo is located. The Gulf is merely 75 yards to the west, and Florida’s Intracoastal Waterway is 75 yards to the east. Relax on the 3rd-floor, ceramic-tiled balcony with screened-in lanai, and gaze out across the serene aquamarine Gulf waters, the Intracoastal Waterway, and Florida’s Sunshine Bridge over Tampa Bay and the Bradenton Beach Marina. The open-concept design of the kitchen/living/dining area makes for easy entertaining. The kitchen island boasts a granite-top bar with stool seating for two, below stylish pendant lamps. The kitchen flows into a dining area with hardwood floors and a beautiful tropical ceiling fan with natural palm blades, which circulates fresh air throughout the main living space. Enjoy the covered lanai, just off the kitchen/living area to dine or relax. The Primary bedroom (third floor) has gorgeous hardwood floors and a walk-in closet. Enjoy your own private balcony/covered lanai with a sitting area and dazzling views of the turquoise Gulf. Just the spot to sip your morning coffee. The Primary ensuite bathroom has a large double-sink granite vanity, huge well-lit mirror, marble floors, oversize jacuzzi soaking tub, and separate walk-in glass door showers. Heated pool, outdoor kitchen and large one car garage, the list goes on. Enjoy breathtaking sunrises and sunsets from multiple decks overlooking both the bay and the Gulf. Leave your car at home and walk to the beach, restaurants, shopping, the pier, and Bridge Street! Come explore everything this stunning home has to offer! 4 Beds ⋅ 3 Baths ⋅ Mma Twnhs SubDv. ⋅ 34217 Zip Code Perfectly positioned in the middle of the Gulf and the Intercostal, you get the best of both worlds! This 4 bedroom, 3 bathroom pool home is 2,678 sq ft and decorated in fun beachy decor. Offering incredible views in every direction because it’s situated in the best location on the entire island! The island is only 150 yards wide where this 3-story condo is located. The Gulf is merely 75 yards to the west, and Florida’s Intracoastal Waterway is 75 yards to the east. Relax on the 3rd-floor, ceramic-tiled balcony with screened-in lanai, and gaze out across the serene aquamarine Gulf waters, the Intracoastal Waterway, and Florida’s Sunshine Bridge over Tampa Bay and the Bradenton Beach Marina. The open-concept design of the kitchen/living/dining area makes for easy entertaining. The kitchen island boasts a granite-top bar with stool seating for two, below stylish pendant lamps. The kitchen flows into a dining area with hardwood floors and a beautiful tropical ceiling fan with natural palm blades, which circulates fresh air throughout the main living space. Enjoy the covered lanai, just off the kitchen/living area to dine or relax. The Primary bedroom (third floor) has gorgeous hardwood floors and a walk-in closet. Enjoy your own private balcony/covered lanai with a sitting area and dazzling views of the turquoise Gulf. Just the spot to sip your morning coffee. The Primary ensuite bathroom has a large double-sink granite vanity, huge well-lit mirror, marble floors, oversize jacuzzi soaking tub, and separate walk-in glass door showers. Heated pool, outdoor kitchen and large one car garage, the list goes on. Enjoy breathtaking sunrises and sunsets from multiple decks overlooking both the bay and the Gulf. Leave your car at home and walk to the beach, restaurants, shopping, the pier, and Bridge Street! Come explore everything this stunning home has to offer! 109 6th Street N Unit A, Bradenton Beach
$2,695,000 Perfectly positioned in the middle of the Gulf and the Intercostal, you get the best of both worlds! This 4 bedroom, 3 bathroom pool home is 2,678 sq ft and ready for you! Offering incredible views in every direction because it’s situated in the best location on the entire island! The island is only 150 yards wide where this 3-story condo is located. The Gulf is merely 75 yards to the west, and Florida’s Intracoastal Waterway is 75 yards to the east. Relax on the 3rd-floor, ceramic-tiled balcony with screened-in lanai, and gaze out across the serene aquamarine Gulf waters, the Intracoastal Waterway, and Florida’s Sunshine Bridge over Tampa Bay and the Bradenton Beach Marina. The open-concept design of the kitchen/living/dining area makes for easy entertaining. The kitchen island boasts a granite-top bar with stool seating for two, below stylish pendant lamps. The kitchen flows into a dining area with hardwood floors and a beautiful tropical ceiling fan with natural palm blades, which circulates fresh air throughout the main living space. Enjoy the covered lanai, just off the kitchen/living area to dine or relax. The Primary bedroom (third floor) has gorgeous hardwood floors and a walk-in closet. Enjoy your own private balcony/covered lanai with a sitting area and dazzling views of the turquoise Gulf. Just the spot to sip your morning coffee. The Primary ensuite bathroom has a large double-sink granite vanity, huge well-lit mirror, marble floors, oversize jacuzzi soaking tub, and separate walk-in glass door showers. Heated pool, outdoor kitchen and large one car garage, the list goes on. Enjoy breathtaking sunrises and sunsets from multiple decks overlooking both the bay and the Gulf. Leave your car at home and walk to the beach, restaurants, shopping, the pier, and Bridge Street! Come explore everything this stunning home has to offer! 4 Beds ⋅ 3 Baths ⋅ Mma Twnhs SubDv. ⋅ 34217 Zip Code Perfectly positioned in the middle of the Gulf and the Intercostal, you get the best of both worlds! This 4 bedroom, 3 bathroom pool home is 2,678 sq ft and ready for you! Offering incredible views in every direction because it’s situated in the best location on the entire island! The island is only 150 yards wide where this 3-story condo is located. The Gulf is merely 75 yards to the west, and Florida’s Intracoastal Waterway is 75 yards to the east. Relax on the 3rd-floor, ceramic-tiled balcony with screened-in lanai, and gaze out across the serene aquamarine Gulf waters, the Intracoastal Waterway, and Florida’s Sunshine Bridge over Tampa Bay and the Bradenton Beach Marina. The open-concept design of the kitchen/living/dining area makes for easy entertaining. The kitchen island boasts a granite-top bar with stool seating for two, below stylish pendant lamps. The kitchen flows into a dining area with hardwood floors and a beautiful tropical ceiling fan with natural palm blades, which circulates fresh air throughout the main living space. Enjoy the covered lanai, just off the kitchen/living area to dine or relax. The Primary bedroom (third floor) has gorgeous hardwood floors and a walk-in closet. Enjoy your own private balcony/covered lanai with a sitting area and dazzling views of the turquoise Gulf. Just the spot to sip your morning coffee. The Primary ensuite bathroom has a large double-sink granite vanity, huge well-lit mirror, marble floors, oversize jacuzzi soaking tub, and separate walk-in glass door showers. Heated pool, outdoor kitchen and large one car garage, the list goes on. Enjoy breathtaking sunrises and sunsets from multiple decks overlooking both the bay and the Gulf. Leave your car at home and walk to the beach, restaurants, shopping, the pier, and Bridge Street! Come explore everything this stunning home has to offer! 109 6th Street N Unit B, Bradenton Beach
$659,900 JUST REDUCED $30,000 The moment you step inside this exceptional second-floor end unit, you’ll feel as though you are living right on top of the water. Offering stunning panoramic views of Sarasota Bay, added privacy, and exceptional tranquility, this beautifully renovated bayfront residence is one of Runaway Bay’s most desirable and rarely available locations. Runaway Bay has only four second-floor bayfront end units and just 16 second-floor bayfront units total, making this an extremely limited opportunity expected to sell quickly. This two-bedroom, two-bath condo features unobstructed bay views, breathtaking sunrises, a private balcony, an A/C system replaced in January 2021, and a new hot water tank installed in 2023. Enjoy daily swims in the Gulf of Mexico with designated private beach access leading to six miles of powdery sand beaches. Community amenities include a heated saltwater pool, fitness room with sauna, tennis, pickleball, bocce ball, shuffleboard, clubhouse, grilling area, fishing pier, and kayak launch. The Anna Maria Island Trolley stops right outside the complex, offering easy access to dining, shopping, miniature golf, live music, and the Historic Bridge Street area. Currently used as the owner’s private residence, this stunning bayfront condo offers the perfect combination of privacy, water views, and Anna Maria Island living. 2 Beds ⋅ 2 Baths ⋅ Runaway Bay SubDv. ⋅ 34217 Zip Code JUST REDUCED $30,000 The moment you step inside this exceptional second-floor end unit, you’ll feel as though you are living right on top of the water. Offering stunning panoramic views of Sarasota Bay, added privacy, and exceptional tranquility, this beautifully renovated bayfront residence is one of Runaway Bay’s most desirable and rarely available locations. Runaway Bay has only four second-floor bayfront end units and just 16 second-floor bayfront units total, making this an extremely limited opportunity expected to sell quickly. This two-bedroom, two-bath condo features unobstructed bay views, breathtaking sunrises, a private balcony, an A/C system replaced in January 2021, and a new hot water tank installed in 2023. Enjoy daily swims in the Gulf of Mexico with designated private beach access leading to six miles of powdery sand beaches. Community amenities include a heated saltwater pool, fitness room with sauna, tennis, pickleball, bocce ball, shuffleboard, clubhouse, grilling area, fishing pier, and kayak launch. The Anna Maria Island Trolley stops right outside the complex, offering easy access to dining, shopping, miniature golf, live music, and the Historic Bridge Street area. Currently used as the owner’s private residence, this stunning bayfront condo offers the perfect combination of privacy, water views, and Anna Maria Island living. 1801 Gulf Drive N Unit 293, Bradenton Beach
$2,650,000 Virtually Staged. Welcome to this extensively renovated waterfront residence in the highly desirable Key Royale community. This 4-bedroom, 4-bath home pairs elevated coastal living with modern improvements and direct boating access to the Gulf. Renovated from top to bottom, including a redesigned chef’s kitchen features high-end finishes and opens to spacious living and entertaining areas, while each bathroom has been updated with clean, contemporary detail. The property includes a new roof, four new A/C units, updated landscaping, a new garage door, and new garage flooring. For added flexibility, the private fourth bedroom above the garage has its own entrance—ideal for guests, multigenerational living, a home office, or a bonus flex space. Designed for entertaining, the home offers a new wet bar and effortless indoor-outdoor flow. Outside, enjoy private canal frontage with a boat lift and direct Gulf access—perfect for boating and island living. Move-in ready and beautifully appointed, this home delivers luxury, versatility, and a true waterfront lifestyle just minutes from renowned beaches, dining, and shopping. Discover modern elegance and relaxed coastal charm in one of Anna Maria Island’s premier boating communities. 4 Beds ⋅ 4 Baths ⋅ Key Royale SubDv. ⋅ 34217 Zip Code Virtually Staged. Welcome to this extensively renovated waterfront residence in the highly desirable Key Royale community. This 4-bedroom, 4-bath home pairs elevated coastal living with modern improvements and direct boating access to the Gulf. Renovated from top to bottom, including a redesigned chef’s kitchen features high-end finishes and opens to spacious living and entertaining areas, while each bathroom has been updated with clean, contemporary detail. The property includes a new roof, four new A/C units, updated landscaping, a new garage door, and new garage flooring. For added flexibility, the private fourth bedroom above the garage has its own entrance—ideal for guests, multigenerational living, a home office, or a bonus flex space. Designed for entertaining, the home offers a new wet bar and effortless indoor-outdoor flow. Outside, enjoy private canal frontage with a boat lift and direct Gulf access—perfect for boating and island living. Move-in ready and beautifully appointed, this home delivers luxury, versatility, and a true waterfront lifestyle just minutes from renowned beaches, dining, and shopping. Discover modern elegance and relaxed coastal charm in one of Anna Maria Island’s premier boating communities. 528 Key Royale Drive, Holmes Beach
$5,250,000 Perfectly positioned in the middle of the Gulf and the Intercostal, you get the best of both worlds! Being sold as a whole- each side is 4 bedrooms and 3 bathrooms and both have their own pool!! Offering incredible views in every direction because it’s situated in the best location on the entire island! The island is only 150 yards wide where this 3-story condo is located. The Gulf of Mexico is merely 75 yards to the west, and Florida’s Intracoastal Waterway is 75 yards to the east. Relax on the 3rd-floor, ceramic-tiled balcony with screened-in lanai, and gaze out across the serene aquamarine Gulf waters, the Intracoastal Waterway, and Florida’s Sunshine Bridge over Tampa Bay and the Bradenton Beach Marina. Each side is 2,678 sq ft luxury condo is one-half of a duplex (shared wall format with extra thick/soundproof wall.) But everything about the condo is private, not shared. Heated pool, outdoor kitchen and large garage, the list goes on. Possibilities are endless, rent out as a whole for investment or live on one side and rent the other. Enjoy breathtaking sunrises and sunsets from multiple decks overlooking both the bay and the Gulf. Leave your car at home and walk to the beach, restaurants, shopping, the pier, and Bridge Street! Come explore everything this stunning home has to offer! 8 Beds ⋅ 6 Baths ⋅ Mma Twnhs SubDv. ⋅ 34217 Zip Code Perfectly positioned in the middle of the Gulf and the Intercostal, you get the best of both worlds! Being sold as a whole- each side is 4 bedrooms and 3 bathrooms and both have their own pool!! Offering incredible views in every direction because it’s situated in the best location on the entire island! The island is only 150 yards wide where this 3-story condo is located. The Gulf of Mexico is merely 75 yards to the west, and Florida’s Intracoastal Waterway is 75 yards to the east. Relax on the 3rd-floor, ceramic-tiled balcony with screened-in lanai, and gaze out across the serene aquamarine Gulf waters, the Intracoastal Waterway, and Florida’s Sunshine Bridge over Tampa Bay and the Bradenton Beach Marina. Each side is 2,678 sq ft luxury condo is one-half of a duplex (shared wall format with extra thick/soundproof wall.) But everything about the condo is private, not shared. Heated pool, outdoor kitchen and large garage, the list goes on. Possibilities are endless, rent out as a whole for investment or live on one side and rent the other. Enjoy breathtaking sunrises and sunsets from multiple decks overlooking both the bay and the Gulf. Leave your car at home and walk to the beach, restaurants, shopping, the pier, and Bridge Street! Come explore everything this stunning home has to offer! 109 6th Street N Unit A & B, Bradenton Beach
$2,495,000 BRAND NEW ROOF | HURRICANE IMPACT WINDOWS & DOORS | 95 STEPS TO THE BEACH | HIGH-PERFORMING NIGHTLY RENTAL| MOTIVATED SELLER Welcome to one of Bradenton Beach’s most exceptional income-producing coastal investments, where luxury lifestyle, proven rental performance, and unbeatable location come together just 95 steps from the sugar-white sands and turquoise waters of Bradenton Beach. Positioned in the heart of one of Florida’s most sought-after beach destinations, this fully renovated beachside duplex presents a rare opportunity to own a turn-key, high-performing short-term rental with no minimum rental restrictions and bookings already extending into 2026. Whether you are an investor seeking strong cash flow, a lifestyle buyer wanting a second home that offsets ownership costs, or someone searching for a legacy beach property, this offering checks every box. Each spacious unit offers over 1,500 square feet of beautifully designed living space with two bedrooms, two bathrooms, private lanais, upscale coastal finishes, and the flexibility to rent separately or together for maximum income potential. Guests are drawn to the property’s walkable island lifestyle. Mornings spent enjoying coffee on the lanai, afternoons on the beach, and evenings filled with Gulf sunsets, live music, and local dining all just moments away. The property has undergone extensive renovations and capital improvements, creating a low-maintenance and highly desirable investment asset. Upgrades include a brand-new roof, hurricane-impact windows and sliding glass doors throughout, Hardie siding, luxury kitchens, spa-inspired bathrooms with oversized walk-in showers and Jacuzzi tubs, hand-scraped maple flooring, elevator access, private garages, and custom coastal details throughout. A true standout feature is the stunning 4th-floor rooftop deck complete with panoramic Gulf and bay views, a saltwater pool and spa, and an unforgettable entertainment space that consistently drives repeat guests and premium rental demand. Since entering the vacation rental market in 2023, the property has demonstrated strong and consistent rental performance with increasing year-over-year demand. With nightly rental flexibility and an irreplaceable location in the heart of Bradenton Beach, this property offers the rare combination of immediate income potential, long-term appreciation, and an unmatched coastal lifestyle. This is more than a beach home, it is a luxury investment experience designed to generate income, create memories, and deliver lasting value for years to come. 4 Beds ⋅ 5 Baths ⋅ Ilexhurst SubDv. ⋅ 34217 Zip Code BRAND NEW ROOF | HURRICANE IMPACT WINDOWS & DOORS | 95 STEPS TO THE BEACH | HIGH-PERFORMING NIGHTLY RENTAL| MOTIVATED SELLER Welcome to one of Bradenton Beach’s most exceptional income-producing coastal investments, where luxury lifestyle, proven rental performance, and unbeatable location come together just 95 steps from the sugar-white sands and turquoise waters of Bradenton Beach. Positioned in the heart of one of Florida’s most sought-after beach destinations, this fully renovated beachside duplex presents a rare opportunity to own a turn-key, high-performing short-term rental with no minimum rental restrictions and bookings already extending into 2026. Whether you are an investor seeking strong cash flow, a lifestyle buyer wanting a second home that offsets ownership costs, or someone searching for a legacy beach property, this offering checks every box. Each spacious unit offers over 1,500 square feet of beautifully designed living space with two bedrooms, two bathrooms, private lanais, upscale coastal finishes, and the flexibility to rent separately or together for maximum income potential. Guests are drawn to the property’s walkable island lifestyle. Mornings spent enjoying coffee on the lanai, afternoons on the beach, and evenings filled with Gulf sunsets, live music, and local dining all just moments away. The property has undergone extensive renovations and capital improvements, creating a low-maintenance and highly desirable investment asset. Upgrades include a brand-new roof, hurricane-impact windows and sliding glass doors throughout, Hardie siding, luxury kitchens, spa-inspired bathrooms with oversized walk-in showers and Jacuzzi tubs, hand-scraped maple flooring, elevator access, private garages, and custom coastal details throughout. A true standout feature is the stunning 4th-floor rooftop deck complete with panoramic Gulf and bay views, a saltwater pool and spa, and an unforgettable entertainment space that consistently drives repeat guests and premium rental demand. Since entering the vacation rental market in 2023, the property has demonstrated strong and consistent rental performance with increasing year-over-year demand. With nightly rental flexibility and an irreplaceable location in the heart of Bradenton Beach, this property offers the rare combination of immediate income potential, long-term appreciation, and an unmatched coastal lifestyle. This is more than a beach home, it is a luxury investment experience designed to generate income, create memories, and deliver lasting value for years to come. 2300 Avenue B, Bradenton Beach
$1,449,000 **ACTIVE Short Term Rental** Financials and Insurance information available upon request. Bookings for 2026 and 2027 in place with strong reviews. 2025 Income $146K with 63% Occupancy (Owners used the Property extensively) still producing $104K NET INCOME.COASTAL INVESTMENT OPPORTUNITY! Elevated duplex. Weekly rentals. One block to the beach. Rare deeded boat slip. Turnkey, Fully Furnished, and Income-Producing from DAY ONE! Welcome to island living at its finest at 8106 Gulf Drive, Units A & B, in Holmes Beach on beautiful Anna Maria Island. This Property offers the ideal blend of personal retreat and exceptional income-producing opportunity, along with private residential beach access to the Gulf of Mexico just one block away. With established rental history, and exceptional guest reviews providing immediate confidence for investors, this turnkey property is ready to generate rental income from day one while offering the flexibility of a personal island getaway whenever the mood strikes. Located just one street from the Anna Maria city limits, where weekly short-term rentals are permitted, it maximizes income potential in one of the island's most desirable locations. Each thoughtfully updated 2-bedroom, 2-bath unit is beautifully furnished with coastal-inspired décor, newer appliances and comfortable mattresses that guests consistently rave about. Simply arrive, unpack, and start enjoying everything island life has to offer. Buy with added peace of mind knowing a pre-listing inspection has already been completed. Highlights include a durable metal roof, well-maintained A/C systems, hurricane impact windows and sliding glass doors (approximately four years old), plus an elevated design with flood barriers for added confidence. Outside, the island lifestyle takes center stage. Private balconies with Adirondack chairs invite morning coffee, sunset breezes and front-row seats to the laid-back rhythm of Holmes Beach. The fully fenced yard, installed just six months ago, creates a welcoming outdoor gathering space, while the side yard grill is perfect for relaxing after a day at the beach. Rinse off in the outdoor shower, store your gear in the owner's storage room and enjoy the convenience of separate laundry and utility rooms with washers and dryers, along with golf cart plug-ins for each unit. The island lifestyle comes fully equipped. Two kayaks, a paddleboard and bicycles are included, making it easy for owners and guests alike to experience the very best of Anna Maria Island. For boating enthusiasts, the story gets even better! A rare deeded boat slip conveys with the property, offering immediate access for launching the included kayaks while presenting the opportunity to create a future dock. It's an uncommon bonus that adds both lifestyle appeal and long-term value. Whether you choose to live in one residence while generating income from the other or maximize your investment by leasing both, this exceptional property offers flexibility, strong rental potential and a collection of amenities rarely found together in a single investment opportunity on Anna Maria Island. Follow your nose to the salt air. Chase another spectacular Gulf sunset. Own your slice of paradise with built-in income potential. No shoes required! 4 Beds ⋅ 4 Baths ⋅ Edgemere Sub SubDv. ⋅ 34217 Zip Code **ACTIVE Short Term Rental** Financials and Insurance information available upon request. Bookings for 2026 and 2027 in place with strong reviews. 2025 Income $146K with 63% Occupancy (Owners used the Property extensively) still producing $104K NET INCOME.COASTAL INVESTMENT OPPORTUNITY! Elevated duplex. Weekly rentals. One block to the beach. Rare deeded boat slip. Turnkey, Fully Furnished, and Income-Producing from DAY ONE! Welcome to island living at its finest at 8106 Gulf Drive, Units A & B, in Holmes Beach on beautiful Anna Maria Island. This Property offers the ideal blend of personal retreat and exceptional income-producing opportunity, along with private residential beach access to the Gulf of Mexico just one block away. With established rental history, and exceptional guest reviews providing immediate confidence for investors, this turnkey property is ready to generate rental income from day one while offering the flexibility of a personal island getaway whenever the mood strikes. Located just one street from the Anna Maria city limits, where weekly short-term rentals are permitted, it maximizes income potential in one of the island's most desirable locations. Each thoughtfully updated 2-bedroom, 2-bath unit is beautifully furnished with coastal-inspired décor, newer appliances and comfortable mattresses that guests consistently rave about. Simply arrive, unpack, and start enjoying everything island life has to offer. Buy with added peace of mind knowing a pre-listing inspection has already been completed. Highlights include a durable metal roof, well-maintained A/C systems, hurricane impact windows and sliding glass doors (approximately four years old), plus an elevated design with flood barriers for added confidence. Outside, the island lifestyle takes center stage. Private balconies with Adirondack chairs invite morning coffee, sunset breezes and front-row seats to the laid-back rhythm of Holmes Beach. The fully fenced yard, installed just six months ago, creates a welcoming outdoor gathering space, while the side yard grill is perfect for relaxing after a day at the beach. Rinse off in the outdoor shower, store your gear in the owner's storage room and enjoy the convenience of separate laundry and utility rooms with washers and dryers, along with golf cart plug-ins for each unit. The island lifestyle comes fully equipped. Two kayaks, a paddleboard and bicycles are included, making it easy for owners and guests alike to experience the very best of Anna Maria Island. For boating enthusiasts, the story gets even better! A rare deeded boat slip conveys with the property, offering immediate access for launching the included kayaks while presenting the opportunity to create a future dock. It's an uncommon bonus that adds both lifestyle appeal and long-term value. Whether you choose to live in one residence while generating income from the other or maximize your investment by leasing both, this exceptional property offers flexibility, strong rental potential and a collection of amenities rarely found together in a single investment opportunity on Anna Maria Island. Follow your nose to the salt air. Chase another spectacular Gulf sunset. Own your slice of paradise with built-in income potential. No shoes required! 8106 Gulf Drive, Holmes Beach
$1,449,000 COASTAL INVESTMENT OPPORTUNITY! Elevated duplex. Weekly rentals. One block to the beach. Rare deeded boat slip. Turnkey, Fully Furnished, and Income-Producing from DAY ONE! Welcome to island living at its finest at 8106 Gulf Drive, Units A & B, in Holmes Beach on beautiful Anna Maria Island. This Property offers the ideal blend of personal retreat and exceptional income-producing opportunity, along with private residential beach access to the Gulf of Mexico just one block away. With established rental history, and exceptional guest reviews providing immediate confidence for investors, this turnkey property is ready to generate rental income from day one while offering the flexibility of a personal island getaway whenever the mood strikes. Located just one street from the Anna Maria city limits, where weekly short-term rentals are permitted, it maximizes income potential in one of the island's most desirable locations. Each thoughtfully updated 2-bedroom, 2-bath unit is beautifully furnished with coastal-inspired décor, newer appliances and comfortable mattresses that guests consistently rave about. Simply arrive, unpack, and start enjoying everything island life has to offer. Buy with added peace of mind knowing a pre-listing inspection has already been completed. Highlights include a durable metal roof, well-maintained A/C systems, hurricane impact windows and sliding glass doors (approximately four years old), plus an elevated design with flood barriers for added confidence. Outside, the island lifestyle takes center stage. Private balconies with Adirondack chairs invite morning coffee, sunset breezes and front-row seats to the laid-back rhythm of Holmes Beach. The fully fenced yard, installed just six months ago, creates a welcoming outdoor gathering space, while the side yard grill is perfect for relaxing after a day at the beach. Rinse off in the outdoor shower, store your gear in the owner's storage room and enjoy the convenience of separate laundry and utility rooms with washers and dryers, along with golf cart plug-ins for each unit. And...The island lifestyle comes fully equipped! Two kayaks, a paddleboard and bicycles are included, making it easy for owners and guests alike to experience the very best of Anna Maria Island. For boating enthusiasts, the story gets even better! A rare deeded boat slip conveys with the property, offering immediate access for launching the included kayaks while presenting the opportunity to create a future dock. It's an uncommon bonus that adds both lifestyle appeal and long-term value. Whether you choose to live in one residence while generating income from the other or maximize your investment by leasing both, this exceptional property offers flexibility, strong rental potential and a collection of amenities rarely found together in a single investment opportunity on Anna Maria Island. Follow your nose to the salt air. Chase another spectacular Gulf sunset. Own your slice of paradise with built-in income potential. No shoes required! 4 Beds ⋅ 4 Baths ⋅ Holmes Beach SubDv. ⋅ 34217 Zip Code COASTAL INVESTMENT OPPORTUNITY! Elevated duplex. Weekly rentals. One block to the beach. Rare deeded boat slip. Turnkey, Fully Furnished, and Income-Producing from DAY ONE! Welcome to island living at its finest at 8106 Gulf Drive, Units A & B, in Holmes Beach on beautiful Anna Maria Island. This Property offers the ideal blend of personal retreat and exceptional income-producing opportunity, along with private residential beach access to the Gulf of Mexico just one block away. With established rental history, and exceptional guest reviews providing immediate confidence for investors, this turnkey property is ready to generate rental income from day one while offering the flexibility of a personal island getaway whenever the mood strikes. Located just one street from the Anna Maria city limits, where weekly short-term rentals are permitted, it maximizes income potential in one of the island's most desirable locations. Each thoughtfully updated 2-bedroom, 2-bath unit is beautifully furnished with coastal-inspired décor, newer appliances and comfortable mattresses that guests consistently rave about. Simply arrive, unpack, and start enjoying everything island life has to offer. Buy with added peace of mind knowing a pre-listing inspection has already been completed. Highlights include a durable metal roof, well-maintained A/C systems, hurricane impact windows and sliding glass doors (approximately four years old), plus an elevated design with flood barriers for added confidence. Outside, the island lifestyle takes center stage. Private balconies with Adirondack chairs invite morning coffee, sunset breezes and front-row seats to the laid-back rhythm of Holmes Beach. The fully fenced yard, installed just six months ago, creates a welcoming outdoor gathering space, while the side yard grill is perfect for relaxing after a day at the beach. Rinse off in the outdoor shower, store your gear in the owner's storage room and enjoy the convenience of separate laundry and utility rooms with washers and dryers, along with golf cart plug-ins for each unit. And...The island lifestyle comes fully equipped! Two kayaks, a paddleboard and bicycles are included, making it easy for owners and guests alike to experience the very best of Anna Maria Island. For boating enthusiasts, the story gets even better! A rare deeded boat slip conveys with the property, offering immediate access for launching the included kayaks while presenting the opportunity to create a future dock. It's an uncommon bonus that adds both lifestyle appeal and long-term value. Whether you choose to live in one residence while generating income from the other or maximize your investment by leasing both, this exceptional property offers flexibility, strong rental potential and a collection of amenities rarely found together in a single investment opportunity on Anna Maria Island. Follow your nose to the salt air. Chase another spectacular Gulf sunset. Own your slice of paradise with built-in income potential. No shoes required! 8106 Gulf Drive Unit A&B, Holmes Beach
$760,000 THIS is the ultimate beachfront "Turn-Key" Investment where shorter-term rentals are permitted. Skip the furniture trucks and design stress and start enjoying a fully furnished vacation home that pays you when you're not using it! Located in the heart of one of the world’s top beaches, Anna Maria Island, this spacious and open concept features a 2-bedroom, 2-bathroom slice of paradise has a flexible 2 week rental policy with a proven track record. This unit is ready for your first sunset or your first rental guest the moment you close. With a "secret" beach access, you are steps away from the sugar-white sands of the Gulf. Enjoy what feels like a private beach experience with exclusive access points sets the mood for intimate sunsets front and center as this building only has 38 units on the beachside. Unlike many island properties, this unit has undergone a complete structural, foundation and reserve milestones so you can relax stress free. From the sparkling heated pool and spa to the tennis courts/pickleball, shuffleboard, elevator and lush tropical grounds, the entire complex radiates a "newly opened" resort energy. Bright and airy with ceramic tile throughout (perfect for sandy toes), plenty of closet space, two skylights for natural Florida sunshine along with being an end unit allowing more natural light, and a private lanai with entries from both the living room and primary suite to take in sunsets. The convenience of having underground assigned parking, a private storage locker for your beach gear, and an in-unit washer/dryer make living here feel like home! With the Hop on the free Island Trolley right outside to explore Pine Avenue's boutiques or walk to the nearby Holmes Beach Plaza, you’ll never run out of things to do whether you live on vacation or are actually on vacation. Invest in a property that works as hard as you do. Between the scarcity of beachfront units and the booming rental market on Anna Maria Island, Unit 207 is the smartest…and most beautiful…move you’ll make this year. Pack your swimsuit and leave the rest to us. Schedule your showing today! 2 Beds ⋅ 2 Baths ⋅ Playa Encantada Condominium SubDv. ⋅ 34217 Zip Code THIS is the ultimate beachfront "Turn-Key" Investment where shorter-term rentals are permitted. Skip the furniture trucks and design stress and start enjoying a fully furnished vacation home that pays you when you're not using it! Located in the heart of one of the world’s top beaches, Anna Maria Island, this spacious and open concept features a 2-bedroom, 2-bathroom slice of paradise has a flexible 2 week rental policy with a proven track record. This unit is ready for your first sunset or your first rental guest the moment you close. With a "secret" beach access, you are steps away from the sugar-white sands of the Gulf. Enjoy what feels like a private beach experience with exclusive access points sets the mood for intimate sunsets front and center as this building only has 38 units on the beachside. Unlike many island properties, this unit has undergone a complete structural, foundation and reserve milestones so you can relax stress free. From the sparkling heated pool and spa to the tennis courts/pickleball, shuffleboard, elevator and lush tropical grounds, the entire complex radiates a "newly opened" resort energy. Bright and airy with ceramic tile throughout (perfect for sandy toes), plenty of closet space, two skylights for natural Florida sunshine along with being an end unit allowing more natural light, and a private lanai with entries from both the living room and primary suite to take in sunsets. The convenience of having underground assigned parking, a private storage locker for your beach gear, and an in-unit washer/dryer make living here feel like home! With the Hop on the free Island Trolley right outside to explore Pine Avenue's boutiques or walk to the nearby Holmes Beach Plaza, you’ll never run out of things to do whether you live on vacation or are actually on vacation. Invest in a property that works as hard as you do. Between the scarcity of beachfront units and the booming rental market on Anna Maria Island, Unit 207 is the smartest…and most beautiful…move you’ll make this year. Pack your swimsuit and leave the rest to us. Schedule your showing today! 6006 Gulf Drive Unit 207, Holmes Beach
$1,074,000 Competitively Priced to sell, come see this beautifully maintained home for yourself! Welcome to your slice of Old Florida charm in the heart of Holmes Beach on Anna Maria Island. Just a 2-minute walk to the beach, this turnkey furnished home captures the easygoing coastal lifestyle that makes Holmes Beach so special. With its laid-back island feel, tropical setting and inviting spaces, this property is ideal as a primary residence, second home or income-producing property. Inspired by the character Holmes Beach is known for; cozy beach-town living, tropical surroundings and a relaxed pace - this home perfectly fits right in. Beautifully maintained and ready to enjoy, the home offers a flexible layout with a non-conforming 4th bedroom, an oversized garage with rec-room area, a screened-in Florida room and a covered patio perfect for enjoying the coastal breeze. The outdoor shower, lush landscaping and welcoming outdoor spaces add to the relaxed island appeal. With recent updates to include the roof replaced in 2018, hurricane impact windows in 2020, bathrooms updated in 2019, water heater replaced in 2022, as well as fresh interior paint, wainscoting and epoxy garage flooring completed in 2025 this home is ready for your next worry-free chapter on Anna Maria Island. The seller has also completed a pre-listing 4-point inspection with clean results, offering added peace of mind. Conveniently located near the beach, island dining and local shops, this is a wonderful opportunity to own a lovingly cared-for home in one of the most charming communities on Anna Maria Island. Note: Pool Rendering and estimate in attachments for informational purposes only. This property qualifies for a lender credit when using preferred lender. Inquire for details. 3 Beds ⋅ 2 Baths ⋅ Ilexhurst SubDv. ⋅ 34217 Zip Code Competitively Priced to sell, come see this beautifully maintained home for yourself! Welcome to your slice of Old Florida charm in the heart of Holmes Beach on Anna Maria Island. Just a 2-minute walk to the beach, this turnkey furnished home captures the easygoing coastal lifestyle that makes Holmes Beach so special. With its laid-back island feel, tropical setting and inviting spaces, this property is ideal as a primary residence, second home or income-producing property. Inspired by the character Holmes Beach is known for; cozy beach-town living, tropical surroundings and a relaxed pace - this home perfectly fits right in. Beautifully maintained and ready to enjoy, the home offers a flexible layout with a non-conforming 4th bedroom, an oversized garage with rec-room area, a screened-in Florida room and a covered patio perfect for enjoying the coastal breeze. The outdoor shower, lush landscaping and welcoming outdoor spaces add to the relaxed island appeal. With recent updates to include the roof replaced in 2018, hurricane impact windows in 2020, bathrooms updated in 2019, water heater replaced in 2022, as well as fresh interior paint, wainscoting and epoxy garage flooring completed in 2025 this home is ready for your next worry-free chapter on Anna Maria Island. The seller has also completed a pre-listing 4-point inspection with clean results, offering added peace of mind. Conveniently located near the beach, island dining and local shops, this is a wonderful opportunity to own a lovingly cared-for home in one of the most charming communities on Anna Maria Island. Note: Pool Rendering and estimate in attachments for informational purposes only. This property qualifies for a lender credit when using preferred lender. Inquire for details. 2905 Avenue C, Holmes Beach
$695,000 Short-term rentals are permitted! Enjoy coastal living at Playa Encantada on Anna Maria Island. This beautifully remodeled second-floor condo features 2 bedrooms and 2 bathrooms and comes fully furnished, making it truly move-in ready. Located in one of the island’s most sought-after beachfront communities, residents enjoy a wide range of amenities including private beach access, a heated swimming pool, spa, tennis and pickleball courts, shuffleboard, elevator access, covered parking, and convenient beach entry just across the street. The unit offers desirable southern exposure with views overlooking the tennis courts. Inside, you’ll find a beautifully remodeled kitchen with elegant quartz countertops, stainless steel appliances, including a spacious double oven and an open-concept layout ideal for entertaining. The primary suite features a generous walk-in closet and a beautifully updated bathroom with a walk-in shower. Crown molding and tile flooring throughout add a refined touch. Additional highlights include an in-unit stackable washer and dryer, a tankless water heater, stainless appliances installed in 2023 and an A/C system installed in 2021. Step out onto the large covered lanai to enjoy Florida’s lush scenery and stunning skies. A private owner’s storage room along with a dedicated parking spot is also included on the ground level. With a two-week minimum rental policy, this property offers excellent potential as an income-producing investment or a relaxing second home. Experience the best of the Florida lifestyle, including convenient private beach access with limited public entry nearby for added privacy. The condo is ideally located near a trolley stop, offering free and easy transportation to nearby restaurants and shops. Call for your private showing today. 2 Beds ⋅ 2 Baths ⋅ Playa Encantada Condominium SubDv. ⋅ 34217 Zip Code Short-term rentals are permitted! Enjoy coastal living at Playa Encantada on Anna Maria Island. This beautifully remodeled second-floor condo features 2 bedrooms and 2 bathrooms and comes fully furnished, making it truly move-in ready. Located in one of the island’s most sought-after beachfront communities, residents enjoy a wide range of amenities including private beach access, a heated swimming pool, spa, tennis and pickleball courts, shuffleboard, elevator access, covered parking, and convenient beach entry just across the street. The unit offers desirable southern exposure with views overlooking the tennis courts. Inside, you’ll find a beautifully remodeled kitchen with elegant quartz countertops, stainless steel appliances, including a spacious double oven and an open-concept layout ideal for entertaining. The primary suite features a generous walk-in closet and a beautifully updated bathroom with a walk-in shower. Crown molding and tile flooring throughout add a refined touch. Additional highlights include an in-unit stackable washer and dryer, a tankless water heater, stainless appliances installed in 2023 and an A/C system installed in 2021. Step out onto the large covered lanai to enjoy Florida’s lush scenery and stunning skies. A private owner’s storage room along with a dedicated parking spot is also included on the ground level. With a two-week minimum rental policy, this property offers excellent potential as an income-producing investment or a relaxing second home. Experience the best of the Florida lifestyle, including convenient private beach access with limited public entry nearby for added privacy. The condo is ideally located near a trolley stop, offering free and easy transportation to nearby restaurants and shops. Call for your private showing today. 6005 Gulf Drive Unit 219, Holmes Beach
$6,195,000 Experience luxury coastal living in this gorgeous modern BEACH HOUSE on Anna Maria Island! Offering full, unobstructed Gulf views this 6-bedroom, 5.5-bath residence features 3,375 sq ft of thoughtfully designed living space and includes an elevator for convenient access to all 3 levels of the home. The open-concept great room showcases panoramic water views and connects seamlessly to the gourmet kitchen, complete with high-end appliances, premium cabinetry, and a sleek dining area. A spacious balcony extends the living space outdoors, providing the perfect setting for enjoying the incredible water views. This property comes exquisitely turnkey furnished. The primary suite offers a relaxing retreat with a king-sized bed, spa-style ensuite bathroom, walk-in shower, soaking tub, and double vanities. Guest bedrooms are each generously sized for comfort and relaxation. Outdoor living is exceptional, highlighted by a rooftop deck with a seating area, and fire pit, ideal for stunning AMI sunsets over the Gulf and complete sunrises over the Bay. The oasis inspired yard features a private heated pool, in-ground spa, outdoor kitchen and a poolside putting green. Located in beautiful Bradenton Beach, this residence is steps from the shoreline and close to local dining, shopping, and the island’s free trolley. With breathtaking Gulf views from nearly every room and successful vacation rental history, this property is ideal as a full-time residence or investment opportunity. If you are dreaming of a BEACH HOME, this is the one! 6 Beds ⋅ 6 Baths ⋅ Cortez Beach SubDv. ⋅ 34217 Zip Code Experience luxury coastal living in this gorgeous modern BEACH HOUSE on Anna Maria Island! Offering full, unobstructed Gulf views this 6-bedroom, 5.5-bath residence features 3,375 sq ft of thoughtfully designed living space and includes an elevator for convenient access to all 3 levels of the home. The open-concept great room showcases panoramic water views and connects seamlessly to the gourmet kitchen, complete with high-end appliances, premium cabinetry, and a sleek dining area. A spacious balcony extends the living space outdoors, providing the perfect setting for enjoying the incredible water views. This property comes exquisitely turnkey furnished. The primary suite offers a relaxing retreat with a king-sized bed, spa-style ensuite bathroom, walk-in shower, soaking tub, and double vanities. Guest bedrooms are each generously sized for comfort and relaxation. Outdoor living is exceptional, highlighted by a rooftop deck with a seating area, and fire pit, ideal for stunning AMI sunsets over the Gulf and complete sunrises over the Bay. The oasis inspired yard features a private heated pool, in-ground spa, outdoor kitchen and a poolside putting green. Located in beautiful Bradenton Beach, this residence is steps from the shoreline and close to local dining, shopping, and the island’s free trolley. With breathtaking Gulf views from nearly every room and successful vacation rental history, this property is ideal as a full-time residence or investment opportunity. If you are dreaming of a BEACH HOME, this is the one! 101 7th Street S, Bradenton Beach
$1,500,000 Newly updated with fresh paint throughout, brand new stainless steel appliances, quartz countertops on kitchen and bathrooms and so much more!! Nestled near the north end of Anna Maria Island, 215 81st Street is a three-bedroom, two and a half bath home boasting over 2,000 square feet of living space—an Airbnb gem zoned for weekly rentals. Just two blocks from some of the island’s most pristine beaches, this property offers a true tropical paradise out back. The fully fenced oasis features a gorgeous pool with a built-in hot tub, while the expansive paver-lined lounge area creates a true island escape. The elevated design includes a two-car garage and a game room—currently set up with a ping pong table, connect 4, and Tic Tac Toe but offering ample space to add additional attractions for guests. The second floor invites you into a bright, open living, dining, and kitchen area featuring a brand new LG stainless steel appliance package and gorgeous quartz countertops. This floor also features a half bath, complemented by a massive, screened-in balcony deck (freshly screened in less then a year ago) overlooking the pool oasis below—perfect for soaking in the tropical ambiance. You will also find a dedicated interior laundry room with full size washer and dryer on this floor as well. On the third floor, you’ll find three spacious bedrooms and two full baths, with the primary suite offering not only luxury but also absolutely gorgeous views from every angle—a panoramic reminder of the beauty that surrounds you on Anna Maria Island. This home is packed with recent updates: a 2022 roof, 2019 AC, and a brand-new water heater. The exterior shines with hardie board siding installed less than a year ago and fresh paint. Beyond the home, you’re a stone’s throw from Pine Avenue’s charm and all that Anna Maria offers—laid-back vibes, local eateries, and coastal culture. Fully furnished and turnkey, this is both a thriving investment and an island escape waiting for you. 3 Beds ⋅ 3 Baths ⋅ Holmes Beach SubDv. ⋅ 34217 Zip Code Newly updated with fresh paint throughout, brand new stainless steel appliances, quartz countertops on kitchen and bathrooms and so much more!! Nestled near the north end of Anna Maria Island, 215 81st Street is a three-bedroom, two and a half bath home boasting over 2,000 square feet of living space—an Airbnb gem zoned for weekly rentals. Just two blocks from some of the island’s most pristine beaches, this property offers a true tropical paradise out back. The fully fenced oasis features a gorgeous pool with a built-in hot tub, while the expansive paver-lined lounge area creates a true island escape. The elevated design includes a two-car garage and a game room—currently set up with a ping pong table, connect 4, and Tic Tac Toe but offering ample space to add additional attractions for guests. The second floor invites you into a bright, open living, dining, and kitchen area featuring a brand new LG stainless steel appliance package and gorgeous quartz countertops. This floor also features a half bath, complemented by a massive, screened-in balcony deck (freshly screened in less then a year ago) overlooking the pool oasis below—perfect for soaking in the tropical ambiance. You will also find a dedicated interior laundry room with full size washer and dryer on this floor as well. On the third floor, you’ll find three spacious bedrooms and two full baths, with the primary suite offering not only luxury but also absolutely gorgeous views from every angle—a panoramic reminder of the beauty that surrounds you on Anna Maria Island. This home is packed with recent updates: a 2022 roof, 2019 AC, and a brand-new water heater. The exterior shines with hardie board siding installed less than a year ago and fresh paint. Beyond the home, you’re a stone’s throw from Pine Avenue’s charm and all that Anna Maria offers—laid-back vibes, local eateries, and coastal culture. Fully furnished and turnkey, this is both a thriving investment and an island escape waiting for you. 215 81st Street, Holmes Beach