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Location, location, location! Just steps from world-famous Bean Point and unforgettable Gulf sunsets, Absolutely Anna is a rare coastal gem in the heart of Anna Maria. This beautifully designed 2-bedroom, 2-bathroom retreat captures the essence of island living with a seamless indoor-outdoor flow and timeless coastal charm. The light-filled open floor plan creates an inviting atmosphere, where the airy living space transitions effortlessly into a well-appointed kitchen, perfect for entertaining after a day at the beach. A spacious screened-in front porch sets the stage for morning coffee and evening breezes, while the expansive covered outdoor living area offers a relaxed cabana-style escape ideal for year-round enjoyment. The primary suite is a private sanctuary, complete with a spa-inspired ensuite featuring double vanities, a walk-in shower, and a private balcony overlooking the pool. The second bedroom, also with its own ensuite bath, opens directly to the screened-in porch, providing guests with a peaceful and private retreat. Whether you’re relaxing poolside, strolling to Bean Point, or soaking in the laid-back island lifestyle, Absolutely Anna delivers the ultimate Anna Maria experience. The home boasts a strong rental history, making it an exceptional opportunity as both a personal escape and an income-producing investment. Adding to its appeal is exciting future potential. Conceptual plans indicate the possibility of adding over 700 square feet on a new upper level, along with a rooftop deck offering sweeping views from the island’s coveted north end, offering an opportunity to further enhance value and flexibility. (All additions subject to city approval and current building regulations.) This is your chance to own a piece of paradise near one of the island’s most iconic beaches. Schedule your private showing today and experience Absolutely Anna for yourself.

2 Beds ⋅ 2 Baths ⋅ Shore Acres SubDv. ⋅ 34216 Zip Code

Location, location, location! Just steps from world-famous Bean Point and unforgettable Gulf sunsets, Absolutely Anna is a rare coastal gem in the heart of Anna Maria. This beautifully designed 2-bedroom, 2-bathroom retreat captures the essence of island living with a seamless indoor-outdoor flow and timeless coastal charm. The light-filled open floor plan creates an inviting atmosphere, where the airy living space transitions effortlessly into a well-appointed kitchen, perfect for entertaining after a day at the beach. A spacious screened-in front porch sets the stage for morning coffee and evening breezes, while the expansive covered outdoor living area offers a relaxed cabana-style escape ideal for year-round enjoyment. The primary suite is a private sanctuary, complete with a spa-inspired ensuite featuring double vanities, a walk-in shower, and a private balcony overlooking the pool. The second bedroom, also with its own ensuite bath, opens directly to the screened-in porch, providing guests with a peaceful and private retreat. Whether you’re relaxing poolside, strolling to Bean Point, or soaking in the laid-back island lifestyle, Absolutely Anna delivers the ultimate Anna Maria experience. The home boasts a strong rental history, making it an exceptional opportunity as both a personal escape and an income-producing investment. Adding to its appeal is exciting future potential. Conceptual plans indicate the possibility of adding over 700 square feet on a new upper level, along with a rooftop deck offering sweeping views from the island’s coveted north end, offering an opportunity to further enhance value and flexibility. (All additions subject to city approval and current building regulations.) This is your chance to own a piece of paradise near one of the island’s most iconic beaches. Schedule your private showing today and experience Absolutely Anna for yourself.

805 N Bay Boulevard, Anna Maria

$1,600,000

Incredible opportunity on the North end of Anna Maria Island. Located in the heart of the city of Anna Maria. Short walks to the Gulf or Bay beaches and all of the lovely attractions on Pine Avenue. Currently on the massive, lots 3&4, 11,500 square foot lot sits two duplex units. A total of FOUR short term 2 bed 1 bath units in Anna Maria!!! Units are ready for your vision, just waiting to become instagram famous. Units like this are few and far between on the North end. 3 of 4 units are equipped with washer/dryer hookups. If having the most famous duplex in Anna Maria is not your thing, then there is potential to build two single family homes on lots 3&4 or an enormous single family home. The gentlemen who acquired this property more than a half century ago had a dream for his family, now it's your turn.

8 Beds ⋅ 4 Baths ⋅ Shore Acres SubDv. ⋅ 34216 Zip Code

Incredible opportunity on the North end of Anna Maria Island. Located in the heart of the city of Anna Maria. Short walks to the Gulf or Bay beaches and all of the lovely attractions on Pine Avenue. Currently on the massive, lots 3&4, 11,500 square foot lot sits two duplex units. A total of FOUR short term 2 bed 1 bath units in Anna Maria!!! Units are ready for your vision, just waiting to become instagram famous. Units like this are few and far between on the North end. 3 of 4 units are equipped with washer/dryer hookups. If having the most famous duplex in Anna Maria is not your thing, then there is potential to build two single family homes on lots 3&4 or an enormous single family home. The gentlemen who acquired this property more than a half century ago had a dream for his family, now it's your turn.

411 Alamanda Road, Anna Maria

$1,575,000

This stunning and private retreat is perfect for those who enjoy indoor/outdoor living, floating in a pool or lounging at your very own tiki bar. Light and bright open concept floor plan and impact sliders that open up to the pool and backyard oasis. This home is offered turnkey furnished and ready to move in or ready to be a great vacation rental. Zoned for 1-7 days. The primary bedroom is spacious and comfortable with your own private bathroom and access directly to the pool area. The other bedroom uses the hallway bathroom. Enjoy the large yard, tiki bar, tropical landscaping, turf put-put golf and more! Plenty of yard for kids to run around and dogs to play and plenty of parking too! Nestled in Anna Maria's quiet north end, it's steps away from sunrise on Tampa Bay and a short walk to sunset at the exclusive Bean Point beach. Quaint shops and restaurants of Anna Maria are just blocks away and close to Pine Avenue. This unique home is the perfect combination of a modern cottage set in a serene tropical environment with a quiet sense of luxury and simple detail. Schedule your private showing today!

2 Beds ⋅ 2 Baths ⋅ Shore Acres SubDv. ⋅ 34216 Zip Code

This stunning and private retreat is perfect for those who enjoy indoor/outdoor living, floating in a pool or lounging at your very own tiki bar. Light and bright open concept floor plan and impact sliders that open up to the pool and backyard oasis. This home is offered turnkey furnished and ready to move in or ready to be a great vacation rental. Zoned for 1-7 days. The primary bedroom is spacious and comfortable with your own private bathroom and access directly to the pool area. The other bedroom uses the hallway bathroom. Enjoy the large yard, tiki bar, tropical landscaping, turf put-put golf and more! Plenty of yard for kids to run around and dogs to play and plenty of parking too! Nestled in Anna Maria's quiet north end, it's steps away from sunrise on Tampa Bay and a short walk to sunset at the exclusive Bean Point beach. Quaint shops and restaurants of Anna Maria are just blocks away and close to Pine Avenue. This unique home is the perfect combination of a modern cottage set in a serene tropical environment with a quiet sense of luxury and simple detail. Schedule your private showing today!

412 Alamanda Road, Anna Maria

$1,555,000

“Anna Maria Oasis” is a Bimini Bay Coastal Classic, perfectly positioned on the coveted north end in the City of Anna Maria. With deep-water access directly from your backyard, no bridges to the bay or the Gulf of Mexico, and a 50’ dock with pilings already in place for lift installation, this property is truly a boater’s and fisherman’s paradise. Originally built in 1972, the home was completely transformed in a top-to-bottom remodel in 2025, blending modern luxury with timeless island charm. No detail was overlooked. Highlights include imported Filipino shell stone flooring throughout, all-new drywall, insulation, plumbing, electrical, paint, fixtures, kitchen, and fresh landscaping. The living space was thoughtfully expanded with energy-efficient mini-split systems, increasing the under-air square footage from 1,582 sq ft to approximately 2,131 sq ft, offering enhanced comfort and flexibility. Additional upgrades include a new pool (2019), new AC unit 2025 and new roof (2020). Designed for effortless indoor-outdoor living, this home is ideal for entertaining, launching a sunset cruise, or unwinding while taking in tranquil water views. This one-of-a-kind island property delivers the ultimate coastal lifestyle. Don’t miss this rare opportunity to own waterfront luxury in the heart of Anna Maria—where elegant design meets laid-back island living. Currently an active vacation rental please see remarks for link to the site.

3 Beds ⋅ 2 Baths ⋅ Wells Bay Harbor SubDv. ⋅ 34216 Zip Code

“Anna Maria Oasis” is a Bimini Bay Coastal Classic, perfectly positioned on the coveted north end in the City of Anna Maria. With deep-water access directly from your backyard, no bridges to the bay or the Gulf of Mexico, and a 50’ dock with pilings already in place for lift installation, this property is truly a boater’s and fisherman’s paradise. Originally built in 1972, the home was completely transformed in a top-to-bottom remodel in 2025, blending modern luxury with timeless island charm. No detail was overlooked. Highlights include imported Filipino shell stone flooring throughout, all-new drywall, insulation, plumbing, electrical, paint, fixtures, kitchen, and fresh landscaping. The living space was thoughtfully expanded with energy-efficient mini-split systems, increasing the under-air square footage from 1,582 sq ft to approximately 2,131 sq ft, offering enhanced comfort and flexibility. Additional upgrades include a new pool (2019), new AC unit 2025 and new roof (2020). Designed for effortless indoor-outdoor living, this home is ideal for entertaining, launching a sunset cruise, or unwinding while taking in tranquil water views. This one-of-a-kind island property delivers the ultimate coastal lifestyle. Don’t miss this rare opportunity to own waterfront luxury in the heart of Anna Maria—where elegant design meets laid-back island living. Currently an active vacation rental please see remarks for link to the site.

519 South Drive, Anna Maria

$1,499,000

Some homes are simply felt before they are fully understood. The moment you arrive at 417 Poinsettia Road, something shifts — the salt air, the sound of water moving gently at the canal's edge, the way the light falls across the pool in the late afternoon. This home is designed for the honest and unhurried experience of Anna Maria Island that we call "Island Time". Tucked on the north end of the island on an oversized lot with canal frontage and a brand-new dock, this two-bedroom, two-bath coastal retreat offers what so many search a lifetime to find: a direct, effortless connection to the water and the world-renowned shores of Anna Maria just steps from your door. Walk to Bean Point, to the Bay beaches, to the City Pier, to the beloved shops and restaurants along Pine Street. The island's azure waters and sugar sand beaches aren't just a destination from here — they are your neighborhood. Inside, the sunroom stretches along the back of the home, framing the pool and canal like a living painting. The pool — recently replastered and retiled in 2022 with a newly rescreened cage in 2025 — is ready to be heated on cooler evenings when the days at the beach run long. The kitchen is complete and thoughtfully equipped, and a park-style charcoal grill awaits for alfresco evenings under the palms. The home has been carefully maintained and meaningfully updated: a metal roof installed in 2020, impact windows, impact doors, and impact garage doors were all replaced in 2025, and a termite treatment was completed this year for absolute peace of mind. The new dock, also completed in 2025, invites early morning launches and golden hour returns — with easy canal access that flows directly to the gulf. Whether you are searching for a private island sanctuary, a legacy property to gather your family & friends, or an island address with short-term rental zoning already in place, 417 Poinsettia offers something rare: the full Anna Maria experience, leaving nothing to want.

2 Beds ⋅ 2 Baths ⋅ Luana Isles SubDv. ⋅ 34216 Zip Code

Some homes are simply felt before they are fully understood. The moment you arrive at 417 Poinsettia Road, something shifts — the salt air, the sound of water moving gently at the canal's edge, the way the light falls across the pool in the late afternoon. This home is designed for the honest and unhurried experience of Anna Maria Island that we call "Island Time". Tucked on the north end of the island on an oversized lot with canal frontage and a brand-new dock, this two-bedroom, two-bath coastal retreat offers what so many search a lifetime to find: a direct, effortless connection to the water and the world-renowned shores of Anna Maria just steps from your door. Walk to Bean Point, to the Bay beaches, to the City Pier, to the beloved shops and restaurants along Pine Street. The island's azure waters and sugar sand beaches aren't just a destination from here — they are your neighborhood. Inside, the sunroom stretches along the back of the home, framing the pool and canal like a living painting. The pool — recently replastered and retiled in 2022 with a newly rescreened cage in 2025 — is ready to be heated on cooler evenings when the days at the beach run long. The kitchen is complete and thoughtfully equipped, and a park-style charcoal grill awaits for alfresco evenings under the palms. The home has been carefully maintained and meaningfully updated: a metal roof installed in 2020, impact windows, impact doors, and impact garage doors were all replaced in 2025, and a termite treatment was completed this year for absolute peace of mind. The new dock, also completed in 2025, invites early morning launches and golden hour returns — with easy canal access that flows directly to the gulf. Whether you are searching for a private island sanctuary, a legacy property to gather your family & friends, or an island address with short-term rental zoning already in place, 417 Poinsettia offers something rare: the full Anna Maria experience, leaving nothing to want.

417 Poinsettia Road, Anna Maria

$1,400,000

Prime Beachside Retreat – Steps to the Sand on Anna Maria Island! Discover coastal living at its finest in this beautifully remodeled and updated 3-bedroom, 2-bathroom single-family home, perfectly positioned west of Gulf Drive in the heart of Anna Maria. Just a short stroll (literally steps away) from the pristine, sugar sandy beaches of the Gulf of Mexico, this residence offers effortless access to turquoise waters, breathtaking sunsets, and the relaxed island vibe that makes Anna Maria a sought-after paradise. The home boasts modern upgrades throughout, including fresh finishes, an open and inviting floor plan, and thoughtful touches that blend comfort with contemporary style. The spacious layout is ideal for families, weekend getaways, or as a high-demand vacation rental investment. One of the standout features? Ample room to add your dream pool—imagine lazy days by your private oasis, just moments from the beach! West of Gulf Drive means no busy roads to cross for beach access, putting you in the most desirable pocket of the island. Enjoy peaceful mornings with the sound of waves, evening walks along the shore, and the charm of nearby Pine Avenue’s shops, restaurants, and cafes—all while owning a piece of true Anna Maria magic. Whether you’re seeking a primary residence, second home, or lucrative rental property, this beachside gem delivers the ultimate in Florida coastal sophistication and easy island living. Don’t miss your chance to own steps from the Gulf—schedule your private showing today!

3 Beds ⋅ 2 Baths ⋅ Gulf View Sub SubDv. ⋅ 34216 Zip Code

Prime Beachside Retreat – Steps to the Sand on Anna Maria Island! Discover coastal living at its finest in this beautifully remodeled and updated 3-bedroom, 2-bathroom single-family home, perfectly positioned west of Gulf Drive in the heart of Anna Maria. Just a short stroll (literally steps away) from the pristine, sugar sandy beaches of the Gulf of Mexico, this residence offers effortless access to turquoise waters, breathtaking sunsets, and the relaxed island vibe that makes Anna Maria a sought-after paradise. The home boasts modern upgrades throughout, including fresh finishes, an open and inviting floor plan, and thoughtful touches that blend comfort with contemporary style. The spacious layout is ideal for families, weekend getaways, or as a high-demand vacation rental investment. One of the standout features? Ample room to add your dream pool—imagine lazy days by your private oasis, just moments from the beach! West of Gulf Drive means no busy roads to cross for beach access, putting you in the most desirable pocket of the island. Enjoy peaceful mornings with the sound of waves, evening walks along the shore, and the charm of nearby Pine Avenue’s shops, restaurants, and cafes—all while owning a piece of true Anna Maria magic. Whether you’re seeking a primary residence, second home, or lucrative rental property, this beachside gem delivers the ultimate in Florida coastal sophistication and easy island living. Don’t miss your chance to own steps from the Gulf—schedule your private showing today!

120 Maple Avenue, Anna Maria

$1,275,000

Welcome to Hawaiian Punch located at 125 Crescent, a charming canal-front retreat in the heart of Anna Maria, Florida. This 4 bedroom, 2 bath home offers a comfortable living space and an enviable location just moments from the island’s beautiful beaches of the beautiful Gulf of Mexico. Enjoy the local shops, restaurants, and waterfront attractions off Pine Avenue. One of the home’s standout features is its canal-front setting with a dock, providing easy access to the water for stand-up paddleboarding, kayaking, and small boats. Spend your mornings on the water, enjoy an afternoon paddle, or simply relax and take in the peaceful surroundings and wild life viewing. When you're ready to explore, Pine Avenue is nearby, offering a wonderful selection of shops, restaurants, and ice cream spots, along with the iconic City Pier. And, of course, the stunning Gulf of Mexico beaches are just a short distance away, making it easy to enjoy everything that makes Anna Maria Island such a special destination. With four bedrooms, two bathrooms, a generous 8,800-square-foot lot, and a prime canal-front location, 125 Crescent offers an ideal combination of space, water access, and island convenience. Whether you're looking for a full-time residence, vacation getaway, or investment opportunity, this property puts the best of Anna Maria right outside your door. This is a very active short term rental with even more potential with some upgrades. Come live the Anna Maria Life!

4 Beds ⋅ 2 Baths ⋅ Luana Isles SubDv. ⋅ 34216 Zip Code

Welcome to Hawaiian Punch located at 125 Crescent, a charming canal-front retreat in the heart of Anna Maria, Florida. This 4 bedroom, 2 bath home offers a comfortable living space and an enviable location just moments from the island’s beautiful beaches of the beautiful Gulf of Mexico. Enjoy the local shops, restaurants, and waterfront attractions off Pine Avenue. One of the home’s standout features is its canal-front setting with a dock, providing easy access to the water for stand-up paddleboarding, kayaking, and small boats. Spend your mornings on the water, enjoy an afternoon paddle, or simply relax and take in the peaceful surroundings and wild life viewing. When you're ready to explore, Pine Avenue is nearby, offering a wonderful selection of shops, restaurants, and ice cream spots, along with the iconic City Pier. And, of course, the stunning Gulf of Mexico beaches are just a short distance away, making it easy to enjoy everything that makes Anna Maria Island such a special destination. With four bedrooms, two bathrooms, a generous 8,800-square-foot lot, and a prime canal-front location, 125 Crescent offers an ideal combination of space, water access, and island convenience. Whether you're looking for a full-time residence, vacation getaway, or investment opportunity, this property puts the best of Anna Maria right outside your door. This is a very active short term rental with even more potential with some upgrades. Come live the Anna Maria Life!

125 Crescent Drive, Anna Maria

$1,267,500

Build your custom island retreat on the north end of Anna Maria Island. This residential lot offers 6500 square feet and presents a rare opportunity to build your dream coastal home directly across the street from the beach. Fantastic potential for sweeping Gulf views from upper levels; perfectly positioned to take advantage of its prime location and beach access, this property offers the ideal canvas for creating a serene seaside escape or standout investment. Adjacent south parcel is available for those looking to expand their vision.

Wells Sub SubDv. ⋅ 34216 Zip Code

Build your custom island retreat on the north end of Anna Maria Island. This residential lot offers 6500 square feet and presents a rare opportunity to build your dream coastal home directly across the street from the beach. Fantastic potential for sweeping Gulf views from upper levels; perfectly positioned to take advantage of its prime location and beach access, this property offers the ideal canvas for creating a serene seaside escape or standout investment. Adjacent south parcel is available for those looking to expand their vision.

810 N Bay Boulevard, Anna Maria

$1,250,000

Love the beach and love to boat? Delightful waterfront home with direct access to open water. Located on the famed North end of Anna Maria Island. This 2 bedroom 2 bathroom home offers incredible opportunities for adventure. Whether it is the sand of the Gulf beaches you seek or if enjoying the water from a boat, kayak, or paddle board is your thing the choice is yours. Another incredible benefit of this location is the proximity to Pine Ave, full of fun shopping and eateries. Generously sized lot is positioned on a cul-de-sac providing privacy due to no through traffic. Concrete block paired with a metal roof creates a formidable structure. As you enter the home you will be welcomed by a sense of coziness. The kitchen features solid wood cabinetry and exquisite Taj Mahal quartzite countertops. Entertaining is aided by the in-ceiling home speaker system. Enjoy year around serene water views from the 300 square foot screened-in lanai equipped with four ceiling fans. Single car garage for all your storage needs or get creative for a possible third bedroom. The large lot leaves ample room for a pool to the front of the house. Schedule a showing today and discover if this piece of paradise if right for you.

2 Beds ⋅ 2 Baths ⋅ Luana Isles SubDv. ⋅ 34216 Zip Code

Love the beach and love to boat? Delightful waterfront home with direct access to open water. Located on the famed North end of Anna Maria Island. This 2 bedroom 2 bathroom home offers incredible opportunities for adventure. Whether it is the sand of the Gulf beaches you seek or if enjoying the water from a boat, kayak, or paddle board is your thing the choice is yours. Another incredible benefit of this location is the proximity to Pine Ave, full of fun shopping and eateries. Generously sized lot is positioned on a cul-de-sac providing privacy due to no through traffic. Concrete block paired with a metal roof creates a formidable structure. As you enter the home you will be welcomed by a sense of coziness. The kitchen features solid wood cabinetry and exquisite Taj Mahal quartzite countertops. Entertaining is aided by the in-ceiling home speaker system. Enjoy year around serene water views from the 300 square foot screened-in lanai equipped with four ceiling fans. Single car garage for all your storage needs or get creative for a possible third bedroom. The large lot leaves ample room for a pool to the front of the house. Schedule a showing today and discover if this piece of paradise if right for you.

109 Tern Drive, Anna Maria

$1,175,000

Virtually Staged. Lowest priced 3 bedroom home currently available on the north end of Anna Maria Island. Located in the City of Anna Maria, where short term rentals are permitted with a 1 to 7 day minimum subject to city registration and compliance, this beautifully updated island home presents an exceptional opportunity to own in one of the most sought after locations on the island. This inviting single level residence offers 3 bedrooms, 2 renovated bathrooms, and a versatile den or mudroom. Vaulted tongue and groove wood ceilings create warmth and character throughout the main living space, while the redesigned kitchen features updated cabinetry, countertops, and newer appliances. New flooring throughout the home complements the bright coastal feel and move in ready condition. Set on an oversized 7,500 square foot lot, the property offers something increasingly difficult to find on the north end of Anna Maria Island: space. Whether you envision a custom pool, outdoor kitchen, tropical entertaining area, or your own private backyard retreat, there is ample room to create the outdoor lifestyle buyers dream about when moving to the island. A current survey is available to assist with future planning. The primary suite opens to a private porch, perfect for morning coffee or evening relaxation, while the expansive screened porch extends the living space outdoors and provides the ideal setting for entertaining family and friends year round. Additional features include a new AC system installed in 2025, a one car garage, outdoor shower, storage shed, fenced yard, mature tropical landscaping, and generous off street parking, a rare and valuable feature on the north end. The location is truly exceptional. Walk or bike to Pine Avenue’s charming shops, restaurants, and cafes. Bayfront Park, Bean Point, and some of Anna Maria Island’s most beautiful beach accesses are all nearby, allowing you to enjoy the very best of island living without ever needing to get in your car. Whether you are searching for a full time residence, seasonal getaway, investment property, or future island retreat, this home offers an outstanding combination of location, flexibility, and value. At $1,290,000, it represents one of the most compelling opportunities currently available on the north end of Anna Maria Island. Come experience the island lifestyle that continues to make Anna Maria one of Florida’s most treasured coastal communities.

3 Beds ⋅ 2 Baths ⋅ Luana Isles SubDv. ⋅ 34216 Zip Code

Virtually Staged. Lowest priced 3 bedroom home currently available on the north end of Anna Maria Island. Located in the City of Anna Maria, where short term rentals are permitted with a 1 to 7 day minimum subject to city registration and compliance, this beautifully updated island home presents an exceptional opportunity to own in one of the most sought after locations on the island. This inviting single level residence offers 3 bedrooms, 2 renovated bathrooms, and a versatile den or mudroom. Vaulted tongue and groove wood ceilings create warmth and character throughout the main living space, while the redesigned kitchen features updated cabinetry, countertops, and newer appliances. New flooring throughout the home complements the bright coastal feel and move in ready condition. Set on an oversized 7,500 square foot lot, the property offers something increasingly difficult to find on the north end of Anna Maria Island: space. Whether you envision a custom pool, outdoor kitchen, tropical entertaining area, or your own private backyard retreat, there is ample room to create the outdoor lifestyle buyers dream about when moving to the island. A current survey is available to assist with future planning. The primary suite opens to a private porch, perfect for morning coffee or evening relaxation, while the expansive screened porch extends the living space outdoors and provides the ideal setting for entertaining family and friends year round. Additional features include a new AC system installed in 2025, a one car garage, outdoor shower, storage shed, fenced yard, mature tropical landscaping, and generous off street parking, a rare and valuable feature on the north end. The location is truly exceptional. Walk or bike to Pine Avenue’s charming shops, restaurants, and cafes. Bayfront Park, Bean Point, and some of Anna Maria Island’s most beautiful beach accesses are all nearby, allowing you to enjoy the very best of island living without ever needing to get in your car. Whether you are searching for a full time residence, seasonal getaway, investment property, or future island retreat, this home offers an outstanding combination of location, flexibility, and value. At $1,290,000, it represents one of the most compelling opportunities currently available on the north end of Anna Maria Island. Come experience the island lifestyle that continues to make Anna Maria one of Florida’s most treasured coastal communities.

216 Gladiolus Street, Anna Maria

$950,000

Located in the highly desirable Anna Maria zip code, this original 1979 two-bedroom, one-bath elevated home sits on a full, enclosed garage foundation and is positioned on an exceptionally large lot. The home is move-in ready while offering the opportunity for significant updates or customization. For buyers seeking an affordable, cost-effective structure that already meets flood elevation requirements, this property is an excellent option. With a generous 141-foot-deep lot, there is ample space to add a pool or create additional outdoor living features. Opportunities like this are becoming increasingly rare in Anna Maria—smaller homes that with a lower purchase costs, reduced taxes, insurance, and maintenance. Whether you choose to renovate the existing residence or take advantage of the expansive lot to build your dream home, this property provides multiple paths to achieve your vision.

2 Beds ⋅ 1 Baths ⋅ Anna Maria Beach SubDv. ⋅ 34216 Zip Code

Located in the highly desirable Anna Maria zip code, this original 1979 two-bedroom, one-bath elevated home sits on a full, enclosed garage foundation and is positioned on an exceptionally large lot. The home is move-in ready while offering the opportunity for significant updates or customization. For buyers seeking an affordable, cost-effective structure that already meets flood elevation requirements, this property is an excellent option. With a generous 141-foot-deep lot, there is ample space to add a pool or create additional outdoor living features. Opportunities like this are becoming increasingly rare in Anna Maria—smaller homes that with a lower purchase costs, reduced taxes, insurance, and maintenance. Whether you choose to renovate the existing residence or take advantage of the expansive lot to build your dream home, this property provides multiple paths to achieve your vision.

416 Magnolia Avenue, Anna Maria

$950,000

Spectacular North End Lot cleared and ready for your new home! Enjoy the Island Life in a central location! Only a block away from Pine Ave shops and Trolley Stop.Tampa Bay and canal views await from the upper levels of new build. Take in the beauty of Bean Point and the sugar sand beaches.Optional HOA provides common dock area for fishing & kayak with direct access channel leading into Tampa Bay. This premier lot gives access to all Anna Maria Island has to offer along with the best sunsets in the world! Options abound with this property: 70 foot width gives ample room for a home intended for full time living, while permitted 1-7 day rentals provide opportunity for investment income. Preliminary plan available for 3077 sq ft 4 bedroom 4.5 bath home w/ 3 car garage or design your own custom home.Your dreams await this blank canvas where Anna Maria Island tranquility meets convenience.

Lake La Vista Sub SubDv. ⋅ 34216 Zip Code

Spectacular North End Lot cleared and ready for your new home! Enjoy the Island Life in a central location! Only a block away from Pine Ave shops and Trolley Stop.Tampa Bay and canal views await from the upper levels of new build. Take in the beauty of Bean Point and the sugar sand beaches.Optional HOA provides common dock area for fishing & kayak with direct access channel leading into Tampa Bay. This premier lot gives access to all Anna Maria Island has to offer along with the best sunsets in the world! Options abound with this property: 70 foot width gives ample room for a home intended for full time living, while permitted 1-7 day rentals provide opportunity for investment income. Preliminary plan available for 3077 sq ft 4 bedroom 4.5 bath home w/ 3 car garage or design your own custom home.Your dreams await this blank canvas where Anna Maria Island tranquility meets convenience.

132 Crescent Drive, Anna Maria

$525,000

“Sittin’ on the dock of the Bay…” Welcome to an effortless island retreat designed for relaxed second-home living on Anna Maria Island. This elevated 2-bedroom, 1-bath waterfront condo is being offered turnkey furnished and includes its own deeded boat slip, providing direct access to Tampa Bay and quick passage to open water. Set along a peaceful canal, the home invites you to slow down and unwind. Enjoy morning coffee or evening breezes from your private back patio as manatees glide by and seabirds fill the air. When you are ready to explore, you are perfectly positioned on iconic Pine Avenue, just steps from local shops, dining, and island favorites, with the historic City Pier nearing completion nearby. Inside, the condo offers a clean, comfortable layout with two generously sized bedrooms and a full bath. The space is move-in ready as is, while also offering future flexibility. Many owners in the Bayou Condo Complex have enhanced their units by opening the kitchen to the living area, adding interior laundry, or converting the walk-in closet into an additional bath, creating exciting options to personalize over time. This residence has been lovingly used as a second home and also allows twice-monthly rentals, offering optional income when you are away. The well-maintained Bayou Condo community recently completed new metal roofs in 2025 and features low condo fees, a designated parking space, and ample guest parking. Whether you envision weekend escapes, seasonal stays, or boating adventures right outside your door, this waterfront condo delivers the ultimate lock-and-leave island lifestyle. Schedule your private showing and discover how easy owning a second home on Anna Maria Island can be.

2 Beds ⋅ 1 Baths ⋅ Bayou Condominium SubDv. ⋅ 34216 Zip Code

“Sittin’ on the dock of the Bay…” Welcome to an effortless island retreat designed for relaxed second-home living on Anna Maria Island. This elevated 2-bedroom, 1-bath waterfront condo is being offered turnkey furnished and includes its own deeded boat slip, providing direct access to Tampa Bay and quick passage to open water. Set along a peaceful canal, the home invites you to slow down and unwind. Enjoy morning coffee or evening breezes from your private back patio as manatees glide by and seabirds fill the air. When you are ready to explore, you are perfectly positioned on iconic Pine Avenue, just steps from local shops, dining, and island favorites, with the historic City Pier nearing completion nearby. Inside, the condo offers a clean, comfortable layout with two generously sized bedrooms and a full bath. The space is move-in ready as is, while also offering future flexibility. Many owners in the Bayou Condo Complex have enhanced their units by opening the kitchen to the living area, adding interior laundry, or converting the walk-in closet into an additional bath, creating exciting options to personalize over time. This residence has been lovingly used as a second home and also allows twice-monthly rentals, offering optional income when you are away. The well-maintained Bayou Condo community recently completed new metal roofs in 2025 and features low condo fees, a designated parking space, and ample guest parking. Whether you envision weekend escapes, seasonal stays, or boating adventures right outside your door, this waterfront condo delivers the ultimate lock-and-leave island lifestyle. Schedule your private showing and discover how easy owning a second home on Anna Maria Island can be.

522 Pine Avenue Unit 7D, Anna Maria

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How much is your home worth?