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8440 Sanderling Road, Sarasota
$4,750,000
Sanderling Club SubDv. ⋅ 34242 Zip Code
Discover an unparalleled opportunity to build your dream estate in one of Siesta Key’s most exclusive and private Gulf-front enclaves. Welcome to 8440 Sanderling Road—an extraordinary homesite located within the prestigious, guard-gated Sanderling Club. Spanning over an acre and offering approximately 275 feet of direct beachfront along the Gulf of Mexico, this rare property is a true slice of paradise. Positioned on a pristine stretch of tropical Siesta Key beach and backed by the tranquil waters of Heron Lagoon, the lot also includes a kayak launch for private water access to the lagoon. Its unique positioning offers both expansive Gulf views and the peaceful serenity of lagoon frontage, creating a setting that’s as rare as it is breathtaking. Sanderling Club residents enjoy unmatched privacy, tropical beauty, and access to exclusive community amenities including a bayside marina, tennis courts, and 24-hour security. As a volunteer site for the Mote Marine Turtle Preservation Program, the property also plays a quiet role in local conservation efforts. Whether you envision a modern architectural statement or a secluded coastal retreat, this Gulf-to-lagoon homesite provides the canvas for a one-of-a-kind legacy property on Siesta Key.

8440 Sanderling Road, Sarasota

1001 Point Of Rocks Road Unit 312, Sarasota
$1,398,000
2 Beds ⋅ 2 Baths ⋅ Siesta Sands Resort SubDv. ⋅ 34242 Zip Code
This spacious and well-appointed direct beachfront condo, located at the southern end of Crescent Beach in one of Siesta Key's most desirable boutique resort communities, offers an exceptional coastal living experience. Unit 312, situated on the 3rd floor, features 2 bedrooms, 2 bathrooms, and two private balconies overlooking the beach, where you can enjoy sweeping Gulf views, refreshing tropical breezes, and unforgettable sunsets year-round. A private parking space, in-unit laundry, and private storage add everyday convenience. Residents of Siesta Sands enjoy an impressive array of resort-style amenities, including beach service for lounge chairs and umbrellas, two heated pools, community Wi-Fi, a poolside gazebo, gas grills, an exercise room, and the serene bamboo lounge. This boutique beachfront community offers a secluded, gated retreat with only 31 units and exclusive private beach access to Crescent Beach. The unbeatable location places you just steps from Siesta Key's South Village.

1001 Point Of Rocks Road Unit 312, Sarasota

9226 Midnight Pass Road Unit 4A, Sarasota
$800,000
2 Beds ⋅ 2 Baths ⋅ Castaway Cove SubDv. ⋅ 34242 Zip Code
Welcome to your boutique waterfront condominium community, Castaway Cove at the south end of Siesta Key. This is one of only eight condominiums, an end unit with a community boat slip and dock on a saltwater canal with quick access to the Gulf. Open floor plan with two bedrooms, two baths, great room and dining room views as well as a screened rear porch overlooking the canal and the Gulf. Enjoy sunsets watching the waves crashing on the beach and the manatees and dolphins splashing in your backyard. Grab a kayak and go for a perfect paddle through the mangrove tunnels or out Midnight Pass into the Gulf. Utilize the available kayak storage. New seawall and new roof on the building. The trolley is nearby and will take you right up the road to Siesta Beach or the Village. Yes, you can have it all on Siesta Key!

9226 Midnight Pass Road Unit 4A, Sarasota

6415 Midnight Pass Road Unit 310, Sarasota
$600,000
2 Beds ⋅ 2 Baths ⋅ Anchorage SubDv. ⋅ 34242 Zip Code
Welcome to The Anchorage Yacht and Tennis Club on Siesta Key, a gated waterfront community that combines resort-style amenities, private deeded beach access just across the street, and rare value for boaters, all in one of the island’s most desirable locations. This turnkey furnished 2-bedroom, 2-bath condo features a split floor plan, ensuite bedrooms, new flooring, and abundant natural light, offering a move-in-ready retreat with strong weekly rental potential. What truly sets The Anchorage apart is its canal-front dockage with first-come, first-serve boat slips, providing direct access to Little Sarasota Bay and the Intracoastal Waterway. For boating enthusiasts, this is an exceptional value—offering a rare opportunity to enjoy waterfront living and boating convenience without the premium price or waitlists typically found on Siesta Key. The Anchorage also features an unmatched amenity package: the largest Olympic-size heated pool on Siesta Key, lighted tennis and pickleball courts, a fitness center, sauna, kayak storage and launch, shuffleboard, BBQ and picnic areas, and lush, tropical landscaping throughout the beautifully maintained grounds. The unit includes one covered assigned parking space, with ample guest parking available. Located mid-Key, just minutes from Siesta Key Village, this property offers the ideal balance of access and escape. Whether you're looking for a beach retreat, a boating lifestyle, an income-producing rental, or all three, this property delivers exceptional value, flexibility, and location in one of Florida’s top coastal destinations.

6415 Midnight Pass Road Unit 310, Sarasota

9397 Midnight Pass Road Unit 505, Sarasota
$530,000
2 Beds ⋅ 2 Baths ⋅ Pointe On Midnight Pass SubDv. ⋅ 34242 Zip Code
Discover an exclusive, gated oasis at the southernmost tip of Siesta Key. This recently renovated 5th-floor condo, nestled within the private 5.2 acre community of The Pointe, offers a lifestyle of unparalleled luxury & tranquility. The residence provides a rare opportunity to witness breathtaking sunrises over Sarasota Bay & celebrate unforgettable sunsets over Midnight Pass & the Gulf of America. Inside, a chef’s kitchen features solid-wood, soft-close cabinetry, granite countertops & several new appliances. The 2 full bathrooms are equally modern with new fixtures & sleek quartz vanity tops. Throughout the light-filled, move-in-ready home with Impact Glass windows, elegant luxury vinyl & porcelain tile provide low-maintenance sophistication. The new professional staging can be included or purchased separately. Relax on your spacious, 29-foot screened lanai as you watch kayakers glide over the water & observe the natural beauty of the Neville Bird Sanctuary. Engage with resort-style amenities, including a heated lap pool & spa, lighted tennis & pickleball courts, a fitness center & saunas. The pet-friendly community offers the ultimate peace of mind with a dedicated management team & dual elevators. For the boater, slips up to 26 feet & kayak storage are available for a nominal annual fee. Located on an elevated part of the Key, this property had no water damage or storm assessments in 2024. Enjoy the convenience of a short stroll to Turtle Beach & the free public trolley to Siesta Village & Siesta Beach.

9397 Midnight Pass Road Unit 505, Sarasota

5830 Midnight Pass Road Unit 89, Sarasota
$650,000
2 Beds ⋅ 2 Baths ⋅ Jamaica Royale SubDv. ⋅ 34242 Zip Code
Wonderful gulf side attached villa in an all ground level association, so no milestone inspections required. This completely updated, open floor plan unit has porcelain tile throughout, new appliances, hot water heater, interior washer and dryer, all new plumbing (Pex), hurricane impact front door and sliders, new closet doors, bathrooms, and more. Fantastic rental history! The HOA installed a new roof on the property in 2023, too! Jamaica Royale allows short term rentals so this could be a great investment property or keep it for your own second home. This is the closest gulf side weekly rental property to the main public beach offering 3 swimming pools, grilling stations and shuffle board. Make this great property yours today at a value!

5830 Midnight Pass Road Unit 89, Sarasota

8773 Midnight Pass Road Unit 204G, Sarasota
$575,000
2 Beds ⋅ 2 Baths ⋅ Island Reef SubDv. ⋅ 34242 Zip Code
Have It All in This Beautifully Remodeled & Fully Furnished "Beach House" style Condo! Welcome to one of Siesta Key’s most desirable pet-friendly communities, perfectly positioned Gulf-to-Bay with quiet, deeded beach access just steps away. This impeccably updated residence offers a smart split floor plan that provides ideal privacy between the main bedroom suite and the guest room. Enjoy morning coffee or evening cocktails on the gorgeous, enclosed lanai, overlooking lush tropical gardens and the sparkling community pool. The well-appointed kitchen features room for a cozy breakfast table and has been completely renewed with high-quality finishes. No detail has been Overlooked: Impact windows, New electric and plumbing, All-new kitchen, Beautifully renovated bathrooms, New flooring throughout, Tasteful, neutral furnishings—move-in ready with no contractor visits needed! Step outside and live the resort lifestyle with multiple pools, boat docks (lifts permitted), tennis and pickleball courts, a fitness center, and grilling areas. After a day at the beach or pool, cast a line from the dock—fish are plentiful! The Siesta Key trolley stops right at your door, offering easy access to shopping, dining, and all the island’s best attractions. First time on the market and truly a must-see—this property checks every box. Let the beach life begin!

8773 Midnight Pass Road Unit 204G, Sarasota

810 Siesta Drive, Sarasota
$3,845,000
3 Beds ⋅ 4 Baths ⋅ Bay Island SubDv. ⋅ 34242 Zip Code
Look no further. Welcome home to your coastal Siesta Key waterfront retreat, a boater’s dream come true. On the desired north end of Siesta Key, this four-bedroom, four-bath residence spans 4,622 square feet of meticulously designed living space. Elevated above flood plain, the residence blends architectural craftsmanship with a premier waterfront lifestyle. Directly on the Intracoastal Waterway with no fixed bridges, the property offers swift access to Big Pass and open Gulf waters. The dock presents panoramic bay views and a new 95-foot seawall with a 40-foot slip equipped with power, water and solar lit pilings, ideal for boating or serene sunrise and sunset viewing. The outdoor experience is elevated by a heated saltwater pool and spa, complete with smart controls, waterfall features and porcelain shellstone decking. Inside, a gourmet kitchen centers the home, featuring a Sub-Zero refrigerator, six-burner Dacor gas range with stainless vent hood, Advantium microwave-convection oven, wine refrigerator, wet bar, soft-close cabinetry with glass uppers, decorator granite surfaces, expansive island and illuminated custom cabinetry. The open-concept family room showcases a cathedral ceiling with sweeping bay vistas, creating a striking indoor-outdoor connection. The expansive primary suite features a private waterfront balcony, new carpet, custom walk-in closet and a spa-style en-suite with a deep soaking tub, frameless rain shower, and dual vanities. Two guest bedrooms are on the first floor, including a rear en-suite with a private entrance that also serves as a dedicated pool bath. A bonus room used as a game and fitness space offers flexible potential and can easily be converted into a fourth bedroom. This residence is within the city limits, allowing for potential short-term rental income, making it an attractive opportunity for personal enjoyment and investment. Additional highlights include hurricane-impact windows and doors, Hunter Douglas custom treatments, crown molding, Brazilian cherry wood flooring and refined interior finishes throughout. Professionally landscaped grounds with new sod, an irrigation system and hardscape pathways complete the setting. Minutes from Siesta Key Beach and Village and a short drive to Southside Village and downtown Sarasota, this residence merges waterfront access with design, privacy and location, offering a rare opportunity to own a premier property on Florida’s Gulf Coast. Click on the fly-through video and Matterport walk-through for more images. Live where every day feels like a resort vacation, make it come true!

810 Siesta Drive, Sarasota

1250 N Portofino Drive Unit 208, Sarasota
$462,500
2 Beds ⋅ 2 Baths ⋅ Siesta Harbor SubDv. ⋅ 34242 Zip Code
Second Floor CORNER END UNIT ON THE CANAL! This is the One You've Been Waiting For on Siesta Key, 2 bedroom 2 bathroom condo next to the Heated Pool and an easy walk across the street to our Private Beach Access through Crescent Arms! Welcome to this delightful, ready to move in 2-bedroom, 2-bath canal front condominium, ideally situated near the Stickney Point Bridge on Siesta Key. Easy on and off the island. Gorgeous granite countertops with a large open kitchen area including bar seating. Absolutely Stunning Porcelain floors throughout the kitchen, living area, bedrooms, hallway and entry. Gorgeous completely renovated bathrooms with Granite countertops in light brown tones and stunning showers. This condo has everything that you will need to move right in. If you are looking for a vacation home with a water view or retiring to a warm climate with a breeze - This is it! Dock your boat at our Harbor for a reasonable fee, clean your fish at one of the many Fishing Stations at our Harbor and enjoy the Deep Water Canal leading directly to the Sailboat Water of the Intracoastal Waterway. Have your morning coffee on the lanai and enjoy the breeze or close the Impact windows and work from your lanai with no distractions, just a breathtaking water view. You'll love how conveniently located you are to exceptional restaurants, Siesta Key Village and the natural beauty of Siesta Key Beach – an easy walk directly across the street. This condo boasts a spacious open floor plan adorned with extra windows since it is an end unit, bathing the dwelling in warm, natural light. The contemporary new flooring adds a classic touch to the layout. Among its foremost features, this unit comes with Impact Windows, a new Air Conditioner, a dedicated carport parking spot, outside storage space and enjoys amenities like a community pool, fitness center, and laundry on the second, third and fourth floors. Elevate your living experience in this beach home, and enjoy all the benefits and convenience it offers. Don't miss this chance to reside in one of the best locations in Sarasota! Active community with lots of activities in season, private beach access directly across the street. The location is wonderful, scat and trolley right outside your door, easy on and off the key, this is an over 55 community! Close to the Heated pool, clubhouse, Grills, outdoor spa, saunas, fishing pier on the Intracoastal Waterway with a great seating area, Exercise Room, Library and Shuffleboard Courts! This is a great community. You Deserve Paradise!

1250 N Portofino Drive Unit 208, Sarasota

940 Siesta Key Place, Sarasota
$1,680,000
4 Beds ⋅ 3 Baths ⋅ Siesta Bayside SubDv. ⋅ 34242 Zip Code
North Siesta Key Waterfront Sanctuary — Where Vision Meets Value An invitation to live extraordinarily on North Siesta Key — where artistry, architecture, and the water’s edge converge. Set on a rare 15,000 sq. ft. peninsula with over 300+ feet of canal frontage, this exceptional property is defined by its sense of seclusion, natural beauty, and endless potential. Mature tropical landscaping and graceful palms create a private world of tranquility within a quiet cul-de-sac of multi-million-dollar estate homes, just moments from Sarasota’s vibrant mainland. Currently graced by a 4-bedroom, 3-bath residence spanning 3,450 sq. ft., the home captures panoramic water views through walls of glass that dissolve the boundary between indoors and out. Expansive living and dining areas open to a serene pool terrace and lush gardens — an ideal stage for gatherings beneath the Gulf Coast sun. Yet the true magic lies in what this setting makes possible. Enjoy the residence as it is, refresh it with your own modern expression, or design a new architectural masterpiece worthy of its rare peninsula site. This is deep-water, no-bridge boating access to Sarasota Bay, steps from Siesta Beach’s world-famous sands and minutes to downtown Sarasota’s acclaimed dining, arts, and cultural scene — a lifestyle that blends coastal ease with cosmopolitan energy. Exceptionally priced to inspire vision, creativity, and investment confidence, 940 Siesta Key Place offers both immediate enjoyment and enduring value within one of Sarasota’s most exclusive waterfront enclaves.

940 Siesta Key Place, Sarasota

4894 Oxford Drive, Sarasota
$762,000
3 Beds ⋅ 3 Baths ⋅ Siesta Bayside SubDv. ⋅ 34242 Zip Code
POOL HOME!! Priced To Sell!! Nestled on the peaceful tranquil island of Siesta Key, renowned for its world-class beach and romantic sunsets. JUST MINUTES FROM Siesta Beach & Village. This is the most wonderful place to embrace island-style living. This north island location on a quiet canopy street is walkable to the village, beach, and renowned Out-of-Door Academy. This 3 Bedroom and 2 & 1/2 Bathroom home is ready for your personal touches. Enjoy relaxing in your Caged Pool & Patio area. This Single family home has approximately 1834 sq.ft. +/- living area and a 2 car garage. The existing home—professionally remediated after flood damage—presents a unique opportunity for those looking to reimagine or completely rebuild. Almost 13,000 sq.ft lot with luscious natural landscaping and mature oaks. Updated roof in late 2019.

4894 Oxford Drive, Sarasota

9397 Midnight Pass Road Unit 906, Sarasota
$624,500
2 Beds ⋅ 2 Baths ⋅ Pointe On Midnight Pass SubDv. ⋅ 34242 Zip Code
Experience breathtaking panoramic views of the Gulf of Mexico and Little Sarasota Bay from this beautifully renovated 9th-floor, 2-bedroom, 2-bathroom condo at The Pointe—nestled on the southernmost tip of Siesta Key. The chef’s kitchen features sleek quartz countertops, custom white cabinetry, and durable porcelain tile flooring. The open-concept living and dining area is designed for both comfort and entertaining, offering stunning vistas from every angle. Wake up to serene bay sunrises in the spacious master suite, complete with an updated en-suite bathroom and generous closet space. The en-suite bath showcases elegant tile flooring and a luxurious walk-in shower. Step onto the expansive lanai to take in breathtaking views of dolphins, manatees, kayakers, paddle boarders, and boats gliding through pristine waters. This private outdoor oasis also overlooks a lush nature preserve, providing a peaceful retreat. Set on over 5 acres of Siesta Key’s stunning coastline, The Pointe offers an array of resort-style amenities, including boat docks, a kayak/canoe launch, a heated pool, spa, sauna, tennis/pickleball courts, BBQ gazebos, a clubhouse, and a fitness center with mesmerizing views of the Intracoastal Waterway. Enjoy the sights and sounds of vibrant wildlife, from playful dolphins to majestic seabirds, all while soaking in the refreshing Gulf breeze. The Pointe is just a short walk or drive to fine and casual dining, with a full-service marina less than a mile away. Turtle Beach is also within walking distance, and nearby shops, coffee spots, nightlife, and public transportation make island living effortless. With captivating sunrises, breathtaking sunsets, and endless natural beauty, this coastal retreat is the ultimate Siesta Key getaway. Schedule your private tour today!

9397 Midnight Pass Road Unit 906, Sarasota

6140 Midnight Pass Road Unit 103, Sarasota
$750,000
1 Beds ⋅ 1 Baths ⋅ Horizons West SubDv. ⋅ 34242 Zip Code
Experience the ultimate island lifestyle in this TURNKEY FURNISHED, west-facing condo at Horizons West—just steps from your private Siesta Key beach! This spacious 1-bedroom retreat boasts over 1,000 sq. ft., soaring ceilings, and a wall of oversized windows framing breathtaking panoramic Gulf, beach, resort pool and sunsets sunset views, including dolphin sightings. Enjoy an open, airy floorplan with a designer kitchen featuring stone countertops, stainless appliances, and a breakfast bar. Relax in the king-sized bedroom with custom California Closets, or host family and friends on the living room sleeper sofa. Recent upgrades include impact windows/doors, 2020 AC, and 2021 water heater. Resort-style amenities abound: 300 ft. of private beach, two pools, spa, cabanas, grills, and a bayside park with day dock. Plus, private carport storage for all your beach toys! Hop on the free Siesta Key trolley for world-class dining and shopping. Come see why Siesta Key is ranked #1 Beach in the USA and #4 in the world—your piece of paradise awaits! View the Video: https://youtu.be/5NK5aBPx5vM

6140 Midnight Pass Road Unit 103, Sarasota

5780 Midnight Pass Road Unit 303, Sarasota
$852,500
2 Beds ⋅ 2 Baths ⋅ Gulf N Bay SubDv. ⋅ 34242 Zip Code
Enjoy the best of Siesta Key living in this bright and airy 2-bedroom, 2-bath condo located within the gated Gulf & Bay Club community. Surrounded by tropical landscaping and peaceful water views, this home offers the perfect mix of comfort and resort-style living just steps from the sand. The spacious floor plan features a welcoming living area that flows into a dedicated dining space and an extended sunroom lined with large windows. Flooded with natural light, this flexible area is ideal for reading, relaxing, or taking in the view of swaying palms and the shimmering Gulf beyond. Gulf & Bay Club spans 32 acres of beautifully maintained beachfront grounds with top-tier amenities including three heated swimming pools, tennis and pickleball courts, saunas, a modern fitness center, EV charging stations, and a clubhouse designed for social gatherings and events. The community also provides private access to Siesta Key’s iconic white-sand beach, recognized among the finest in the country. An elevator offers easy access, and the free island trolley is just outside, ready to take you to the shops, restaurants, and live music of Siesta Village. Whether you’re searching for a year-round residence or a seasonal escape, this home captures the essence of coastal comfort and island living.

5780 Midnight Pass Road Unit 303, Sarasota

5112 Jungle Plum Road, Sarasota
$1,600,000
2 Beds ⋅ 3 Baths ⋅ Hidden Harbor SubDv. ⋅ 34242 Zip Code
Attention architecture enthusiasts: This midcentury-modern waterfront home seamlessly blends timeless design with modern convenience. Resilient through three major storms, it sustained no damage beyond minor landscaping impacts and minimal water in the garage. Set on a lush 0.61-acre lot in the coveted Hidden Harbor neighborhood, this jungle oasis offers an unparalleled living experience. The property boasts tropical landscaping, a tranquil koi pond, and a canal-front boat dock. A circular paver driveway leads to a two-car attached garage, while the backyard oasis features a screened patio, multiple paver seating areas, and two upper-level balconies with breathtaking long canal views. Built for durability, the home includes a buried propane tank connected to a whole-house generator and an irrigation system fed by a dedicated well. Inside, the living room captivates with vaulted cypress ceilings, exposed beams, a wood-burning fireplace, hardwood flooring, and double French doors that open to the patio overlooking the canal. The dining room, adjacent to the kitchen, offers hardwood flooring, sliding glass doors, and a charming chandelier. The kitchen combines functionality and elegance, featuring granite countertops, under-cabinet lighting, and a reverse osmosis water filtration system. Upstairs, the primary suite is a private retreat with vaulted ceilings, a spacious walk-in cedar closet, and sliding glass doors opening to a balcony with sweeping canal views. The en-suite bathroom features dual sinks, a soaking tub, a walk-in shower, and vintage tile accents. An adjacent office/den offers built-in shelving, transom windows, and access to two balconies — one overlooking the canal and the other the front yard. On the main floor, the guest suite includes an 11-foot vaulted ceiling, private deck access, and an en-suite bathroom. Additional spaces include a cozy family room with dual sliding glass doors to the patio and an interior atrium filled with lush plants. Conveniently located just 1.3 miles from Siesta Key Beach and dining, 2 miles from shopping, and a short drive to downtown Sarasota, Sarasota Memorial Hospital, and the airport, this home offers both serenity and accessibility. This is a rare opportunity to own a piece of architectural history in a prime location. Experience the perfect fusion of timeless design, modern amenities, and waterfront living in this Hidden Harbor gem.

5112 Jungle Plum Road, Sarasota

6350 Midnight Cove Road Unit 710, Sarasota
$420,000
2 Beds ⋅ 2 Baths ⋅ Midnight Cove Bayside SubDv. ⋅ 34242 Zip Code
If you're searching for deeded beach access and resort-style living on beautiful Siesta Key, this 2-bedroom, 1.5-bath condo could be your perfect match. Enjoy peaceful canal views and lush, mature landscaping in a community that remained untouched by flooding during recent hurricanes. The condo is in original condition and ready for your personal touch to transform it into your coastal retreat. Midnight Cove II offers deeded beach access and an impressive array of resort-style amenities, including a heated pool, tennis courts with pickleball nets, a basketball hoop, car wash station, barbecue grills, fitness center, and covered carport parking. Private docks are also available for your boat. Ideally located on Siesta Key, you'll be just steps from the pristine white sands of Crescent Beach and minutes from world-famous Siesta Beach. A quick ride brings you to Siesta Key Village, where you'll find lively restaurants, shops, and entertainment. Or take a short five-minute stroll to nearby dining and conveniences. Relax and embrace the Siesta Key lifestyle where every day feels like a vacation.

6350 Midnight Cove Road Unit 710, Sarasota

6236 Midnight Pass Road Unit 300, Sarasota
$771,250
2 Beds ⋅ 2 Baths ⋅ Siesta Dunes Beach SubDv. ⋅ 34242 Zip Code
Experience coastal living at its finest in residence #300 at Siesta Dunes, ideally on renowned Siesta Key Beach. This meticulously remodeled two-bedroom, two-bath condominium offers 1,150 square feet of luxurious living space on the third floor, providing a tranquil ambiance and a sense of escape. Crown molding accents the professionally decorated interior, creating a sophisticated atmosphere. Sold turnkey furnished, this residence offers a seamless transition into upscale beachside living. Go inside to find chiseled travertine tile flooring throughout, adding natural coastal charm. The chef’s kitchen is equipped with granite countertops, stainless steel appliances and maple cabinetry, blending style and functionality. French glass doors open to a private lanai terrace surrounded by lush garden views. The lanai is enclosed with hurricane-resistant sliders, while the primary suite features hurricane-resistant windows for added peace of mind. The primary suite also includes a custom-organized walk-in closet, enhancing storage and convenience. A convenient stackable washer and dryer are in the unit. Additional features include an assigned covered carport, a private storage closet, ample guest parking and access to the building elevator. Siesta Dunes is a gated community offering a wealth of resort-style amenities, including a heated pool and spa for year-round enjoyment, a beachside deck, pavilion, clubhouse, and tennis and pickleball courts. Utilizing the on-site property management company makes renting the property easy and carefree. With excellent rental potential, two-week minimum stays from January 15 through the end of April and one-week minimums the rest of the year, this condominium is a compelling investment opportunity as well as a personal retreat. Siesta Dunes is in a good location, making it easy to explore Sarasota’s world-class dining, shopping and entertainment. Siesta Key Beach is just a short distance away, recently named the No. 1 beach in America by TripAdvisor. Renowned for its powdery white sand, clear waters and stunning sunsets, it’s no wonder Siesta Beach is considered the pinnacle of coastal living. Whether you seek a full-time residence, a luxurious vacation retreat or a high-value investment, this extraordinary property exemplifies the best of gulf-front living.

6236 Midnight Pass Road Unit 300, Sarasota

101 Whispering Sands Drive Unit 205, Sarasota
$325,000
2 Beds ⋅ 2 Baths ⋅ Whispering Sands SubDv. ⋅ 34242 Zip Code
Another REDUCTION! Bring your offers! Here's your opportunity to customize your dream waterfront condo on Siesta Key in the sought after Whispering Sands community! Featuring 2 bedrooms and 2 full baths..and boasting your own private, and expansive water view from your huge enclosed lanai. Location is prime.. short stroll to Siesta Village, filled with shopping, restaurants and fun.. Impressive amenities .. 800 feet of private beach on the Gulf, 2 heated pools, fitness centers, clubhouse with catering kitchen, kayak storage, tiki hut , grill area, shuffleboard, and pathways throughout the lush, tropical, grounds that surround the Gulf waters and lagoon filed with abundant nature. Design your own little piece of ISLAND PARADISE and experience the lifestyle on World famous Siesta Key! 55+ community, 2 month min. rental, 2 times a year

101 Whispering Sands Drive Unit 205, Sarasota

1100 Cove Ii Place Unit 910, Sarasota
$900,000
2 Beds ⋅ 2 Baths ⋅ Midnight Cove Ii SubDv. ⋅ 34242 Zip Code
Rare 1st Floor End-Unit Condominium with Boat Slip, across from Crescent Beach! Welcome to this rarely available 1700 square foot 1st-floor end-unit condominium decorated by Robb and Stucky. Ideally located across the street from Crescent Beach and just minutes from the world-renowned Siesta Key Beach. This property includes an exclusive 24' boat slip, just steps away from your back door, equipped with both electric and water hookups. The Association allows boat lifts for ultimate boating convenience. The home boasts a recently updated kitchen featuring a stunning new backsplash, waterfall quartz countertops, modern appliances with new microwave, and more. In addition to the spacious primary bedroom with an en-suite bathroom, the unit offers a second bedroom and a versatile bonus room, perfect as an office, den or additional sleeping space. It features an in-unit laundry room with a new washer and dryer. Cable TV and Fiber Internet is included in the condo fee! Turnkey furnished and move-in ready, making it the perfect retreat or investment property. The updated lanai includes a wine refrigerator, stone countertop and large storage area, ideal for enjoying morning coffee or entertaining guests. The guest bath features a luxurious jacuzzi tub for added relaxation. Enjoy a variety of community amenities, including a heated pool, basketball, tennis, and pickleball courts, as well as a fitness center. If you’re seeking an investment opportunity, Midnight Cove II allows weekly rentals and offers an optional on-site rental department. The community is financially strong, with fully funded reserves and has passed a recent SIRS inspection with flying colors. The property is well maintained and the building just had a new elevator installed. Don’t miss the chance to own this incredible property with endless possibilities!

1100 Cove Ii Place Unit 910, Sarasota

26 Sandy Hook Road N, Sarasota
$10,500,000
5 Beds ⋅ 7 Baths ⋅ Sandy Hook SubDv. ⋅ 34242 Zip Code
Welcome to this extraordinary Gulf-front estate located in one of Siesta Key’s most exclusive enclaves. Situated on a full acre in the private Sandy Hook community, this fully renovated, turnkey residence offers over 5,000 square feet of refined living space and more than 3,000 square feet of covered outdoor areas, all just a short stroll from Siesta Key Village and with direct access to a private community beach. Inside, the layout features five en-suite bedrooms, two powder baths, a dedicated office, and a three-car garage with beach cruisers and kayaks included. Floor-to-ceiling Andersen impact windows frame panoramic Gulf views, while rich finishes like Sapele mahogany siding, IPE hardwood decking, and a custom Pecky Cypress entertainment system reflect the home’s elevated craftsmanship. The chef’s kitchen is a showpiece, centered around a Labradorite Lumarian Blue granite island imported from Brazil, with Wolf, Miele, and Sub-Zero appliances throughout. The spa-inspired primary suite includes a waterfall feature wall, dual curbless shower, lighted soaking tub, and Toto smart toilets. A private elevator and full smart-home system ensure ease and efficiency. Outdoor living is exceptional, with a heated saltwater pool and Jacuzzi, a fully equipped summer kitchen, a covered outdoor living room with fireplace and TV, a poolside theater with dual fireplaces and TVs, and a sunset-facing gas fire pit. The professionally designed $1M+ tropical landscape includes advanced mosquito-misting and irrigation systems for effortless maintenance. With direct access to a private, resident-only beach and an ideal location just minutes from restaurants, shopping, and entertainment, this one-of-a-kind estate offers a rare opportunity to experience the best of coastal living on Siesta Key. Designed for elevated living and effortless enjoyment, 26 Sandy Hook Road S is more than a home—it is a fully realized Gulf-front sanctuary.

26 Sandy Hook Road N, Sarasota

6100 Midnight Pass Road Unit 401, Sarasota
$6,925,000
4 Beds ⋅ 5 Baths ⋅ Halcyon Siesta Key SubDv. ⋅ 34242 Zip Code
A Once-in-a-Lifetime Offering! Introducing Penthouse #401 at Halcyon Siesta Key—an extraordinary coastal sanctuary where architectural brilliance meets unparalleled exclusivity. This is not just a residence; it’s a legacy. Set atop a boutique, six-unit Gulf-front building, Penthouse #401 is the first and only unit ever to be offered for sale—a true rarity as timeless and coveted as the quartz-crystal sands of Siesta Key Beach, just beyond your expansive floor-to-ceiling windows. Enter through a private elevator into your own foyer and be instantly captivated by panoramic views of the Gulf of Mexico. Encompassing 3,525 square feet, this residence was masterfully designed to blend modern sophistication with relaxed coastal luxury. At the heart of the home lies a chef’s kitchen that redefines gourmet living: top-of-the-line Wolf appliances, double ovens, dual sinks, an oversized island, built-in wine fridge, walk-in pantry, coffee bar, and bespoke cabinetry—crafted for both grand entertaining and effortless everyday living. The open-concept layout flows gracefully through dining and living spaces, enhanced by polished terrazzo flooring and Lutron-controlled lighting and shades that adjust with the touch of a button. Wake up to shimmering Gulf views in the tranquil primary suite, a true retreat offering a spa-like en-suite with radiant heated floors, dual vanities, a sculptural soaking tub, and an oversized glass-enclosed shower. Step outside to a spectacular 674 sq. ft. wraparound balcony—ideal for morning espresso, sunset cocktails, or simply soaking in Siesta Key’s year-round beauty. Three additional guest suites provide private en-suite baths and generous closet space, while a full laundry room, powder bath, and abundant storage complete the home’s thoughtful layout. A private two-car garage ensures convenience and security—an invaluable feature in this exclusive enclave. Life at Halcyon is curated for ease and elegance, with upscale amenities including on-site maintenance, a historic clubhouse, beachfront pool, grilling station, fire pit, and private beach access. Just minutes from Siesta Key Village and Sarasota’s cultural and culinary delights, this location offers the perfect blend of privacy and accessibility. Penthouse #401 is more than a luxury residence—it’s a one-of-one opportunity to own a piece of Gulf-front history on Florida’s most treasured beach.

6100 Midnight Pass Road Unit 401, Sarasota

1093 Lake House Circle Unit C205, Sarasota
$650,000
2 Beds ⋅ 2 Baths ⋅ Our House At The Bch SubDv. ⋅ 34242 Zip Code
Discover this wonderful beach retreat and investment opportunity! Perfectly located in one of the most desirable locations in the community and just across the street from the soft, powdery sands of Siesta Key Public Beach ranked # 1 in the USA. This true split plan 2 -bedroom, 2-bath condo at Our House at the Beach offers the ideal setup for coastal living and rental potential. As you step inside the townhouse, you are greeted with high ceilings and bright open spaces. The eat-in kitchen is filled with natural light and connects seamlessly to the dining and living areas which open onto a spacious balcony for enjoying the gulf breezes and spectacular sunsets or winding down after a day at the beach. primary suite features a newly renovated bathroom with a walk-in shower, shaker-style vanity, generous closet space, and a private dressing area. This turnkey unit is sold fully furnished, including some fresh new pieces recently added by the owners. Currently used as an active rental on Airbnb and the rental community website. Weekly rentals are allowed and there is an on-site rental office which makes managing guests simple and convenient. The community offers resort style amenities including a heated swimming pool, two tennis courts, a pavilion with grilling stations. Your own private one-car garage with extra storage ensures there is no beach parking stress! Just load up your cart and head across the street to enjoy Siesta Key Beach, sand volleyball, pickleball & tennis, and Sunday Sunset Drum Circle. When you're ready to explore the island, there is easy access to the free Siesta Key trolley. You can explore the excellent local restaurants, bars, ice cream shops, boutiques, and grocery store which are only a short ride away. Whether you're looking for a beach getaway, an excellent income producing vacation rental, or a coastal home, this turnkey condo delivers the ultimate in comfort, convenience, and laid-back island lifestyle. Don’t miss your chance to own a piece of paradise on Siesta Key.

1093 Lake House Circle Unit C205, Sarasota

6150 Midnight Pass Road Unit V12, Sarasota
$615,000
2 Beds ⋅ 2 Baths ⋅ Island House SubDv. ⋅ 34242 Zip Code
This is the one * WELCOME TO THIS STUNNING WATERFRONT SIESTA KEY VILLA IN MUCH SOUGHT AFTER ISLAND HOUSE BEACH RESORT *The LOWEST PRICED VILLA and the BEST VALUE in ISLAND HOUSE * The current homeowner painstakingly oversaw every step of the renovations from the NEW KITCHEN to the NEW BATHROOMS, NEW FLOORING & NEW LIGHTING * 1 Car Carport with Utility Room which includes a Washer & Dryer * Thoughtfully reimagined Chef's Kitchen with NEW Shaker-style cabinets, QUARTZ countertops, large center island & stainless steel appliances * 2 Bedrooms & 2 Full Baths * Family Room is adjacent to the open Kitchen * PLUS an Enclosed Florida Room * This is the perfect location to create family memories; it's perfect for entertaining family & guests or for simply relaxing in your slice of paradise * On-site rental management is ideal for creating income as a perfect opportunity for investment * This villa SHOWS LIGHT & BRIGHT with an ABUNDANCE OF NATURAL LIGHT * DIRECT ACCESS TO WORLD FAMOUS SIESTA KEY BEACH * Private Cabanas, Community Heated Pool and a Recreation Center * Ideally located in the HEART OF SIESTA KEY * Close to all of the Siesta Key amenities * One look & you'll fall in love *

6150 Midnight Pass Road Unit V12, Sarasota

548 Siesta Drive, Sarasota
$2,695,000
3 Beds ⋅ 4 Baths ⋅ Bay Island SubDv. ⋅ 34242 Zip Code
548 Siesta Drive is more than just a home—it’s a gateway to the best of Siesta Key living with unmatched flexibility, location, and waterfront luxury. Welcome to this luxury coastal retreat on North Siesta Key, perfectly positioned inside Sarasota city limits, making it a rare short-term rental–friendly opportunity. With deep water access just seconds from the Bay, two boat lifts, and a jet ski lift, this home is tailor-made for boaters, water enthusiasts, and investors seeking a strong rental return. Property Highlights • 3 bedrooms | 3.5 bathrooms | Bonus room • Over 4,300 sq. ft. of living space • Nearly 5,000 sq. ft. total under roof • Prime North Siesta Key location in city limits • Quick drive to Downtown Sarasota and Siesta Key Village • Short-term rental potential in one of Sarasota’s hottest markets Interior Features As you step inside, you’re greeted by soaring vaulted ceilings and gleaming oversized porcelain white tile floors that set the tone for the home’s regal, modern style. • Living Room: Expansive and open with dramatic volume ceilings • Bonus Room: Hidden retreat above the garage ideal for a quiet office, playroom, or guest space • First Suite: Convenient en suite bedroom on the main floor • Primary Suite: Oversized retreat with a private screened lanai, spacious walk-in closets, and a beautifully remodeled spa-style shower • Third Bedroom: Private en suite with direct access to the pool deck The chef’s kitchen and entertaining area have been fully remodeled with high-end finishes, blending function and style for both everyday living and gatherings. Outdoor Living Step outside to your large lap pool with water views, framed by paver decking and multiple lounging areas. With direct boating access, two boat lifts, and a jet ski lift, the water is truly an extension of your backyard. Key Upgrades This home has been renovated from top to bottom, ensuring a move-in-ready experience with timeless finishes and thoughtful design details.

548 Siesta Drive, Sarasota

1235 Dockside Place Unit 108, Sarasota
$800,000
2 Beds ⋅ 2 Baths ⋅ Harbour Towne SubDv. ⋅ 34242 Zip Code
“Living the Siesta Key Life” is waiting for you. BOAT DOCK AND DEEP- WATER BASIN.( 13,000 lb lift) Private single car garage too! This first floor 2-bedroom condo is totally updated, with a new kitchen, quartz countertops and breakfast bar, spacious bathrooms, custom doors and new beautiful easy-care tile throughout. This unit is selling totally furnished. Open floor plan for entertaining family and friends. The master has water views with sliding glass door for lots of light. The second bedroom enjoys a private tropical garden view. This community offers an amazing clubhouse, grills, large swimming pool, spa, tennis, pickleball courts and fishing pier. Walk to the crystal white sands and blue water of world-famous Siesta Key Beach and enjoy swimming, walking, sunning and reading in paradise. Walk or take the trolley to lively Siesta Key Village for dining in casual and formal restaurants, enjoy listening to live music.

1235 Dockside Place Unit 108, Sarasota

19 Whispering Sands Drive Unit 1105, Sarasota
$1,270,000
2 Beds ⋅ 2 Baths ⋅ Whispering Sands SubDv. ⋅ 34242 Zip Code
EXQUISITE GULF FRONT LUXURY! Just one floor from the top, this stunning, 11th floor, FULLY remodeled GULF FRONT tower residence offers a seamless blend of sophistication and coastal style against a background of breathtaking, unobstructed 180-degree views of the shimmering Gulf! A rare combination of sophistication, comfort, and coastal beauty, this residence defines modern Gulf front luxury living. Every detail of this 2022 remodel reflects the finest in contemporary design and craftsmanship. The open concept interior is graced with beautiful wide plank tile flooring, seamlessly connecting living, dining, and kitchen spaces to the endless blue horizon beyond. True floor-to-ceiling 2020 hurricane impact sliders open to mesmerizing Gulf vistas, enhanced by Hunter Douglas motorized light-filtering shades for effortless ambiance control. The gourmet kitchen is a showpiece featuring striking Cambria® quartz surfaces, a dramatic 8’ waterfall breakfast bar with dimmable pendant lighting, Bosch stainless appliances, 32 bottle wine refrigerator, fabulous under counter drawer microwave, and custom soft-close cabinetry. The serene primary suite is equally refined, featuring a spa-inspired ensuite tiled bath with Cambria® quartz dual vanity and glassed walk-in shower. The guest bath echoes the same refined elegance. FURNITURE AND FURNISHINGS including Robb & Stucky pieces are included with the sale of the property, minus a small exclusion list.

19 Whispering Sands Drive Unit 1105, Sarasota

5223 Shadow Lawn Drive, Sarasota
$700,000
3 Beds ⋅ 2 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code
One or more photo(s) has been virtually staged. Siesta Key Beach Retreat – Now $829,000 Welcome to 5223 Shadow Lawn Dr, a 3-bedroom, 2-bath home in coveted Siesta Isles, just 1 mile from the sugar sands of Siesta Key Beach. Located on a quiet cul-de-sac with preserve views and mature palms, this 1,459 sq. ft. property blends lifestyle, privacy, and investment potential. Inside, you'll find a bright open layout, modern laminate flooring, neutral finishes, and a renovated kitchen with granite countertops, stainless steel appliances, and crisp light cabinetry. The living area opens to a spacious screened lanai with a fully restored pool (completed October 2025)—now crystal clear and ready to enjoy. The primary suite features an updated en-suite bath, while two additional bedrooms and a second bath provide flexibility for guests, family, or a home office. With no HOA, 30-day rentals permitted, and a prime location near Siesta Village and Downtown Sarasota, this property delivers both lifestyle and upside. Highlights: - 3 Beds | 2 Baths | 1,459 Sq. Ft. - Fully restored pool (Oct 2025) - Renovated kitchen with granite & stainless - Spacious screened lanai + private preserve backdrop - Quiet cul-de-sac location - No HOA | 30-day rentals allowed - 1 mile to Siesta Key Beach One of the best-priced homes in Siesta Isles.

5223 Shadow Lawn Drive, Sarasota

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