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$1,025,000
3 Beds 2 Baths A4594551 MLS
Welcome to paradise in Siesta Cove located half a mile from Siesta Key's famous white sands of Siesta Key Beach off Gulf of Mexico's beautiful, shallow, warm waters. If you are planning to move to Florida, this neighborhood should be on your must-see list. Siesta Key's laid back coastal lifestyle, shops, restaurants and cafes of Siesta Key Village, playground and tennis courts bring joy to all ages. Ample open floor plan opens up to large lanai by 4 sliders and pool bath. The caged 30' x 15' pool is surrounded by serenity with outdoor vegetation privacy wall on three sides; Live Oaks; Palms; Camellias; red, pink & yellow Hibiscus; large Birds of Paradise; multiple Calusa bushes; Bromeliad. Stay out in the spring showers under around 400 sqft of overhang covered seating & lounging area with 3 cooling ceiling fans with lighting. Decorative leaded glass at front door and side panels welcome you into the living and dining room combo. Split 2 bedroom, pool bath wing protects guest's privacy by pocket door separated from main living area. Pool bath has tiled tub/shower. 18” square porcelain white tiles throughout the house. Wood burning fireplace warms up family room, kitchen combo with built-ins. Firebox, internal flue and chimney top spiffed up in 2021, with new stainless steel topside damper installed, operated with pull chain in firebox to keep yours hands safe. Two walk-in closets, dual sinks, Ceramic tiled, large walk-in shower with shelf found in primary bedroom/bath with plenty of storage space. Guest bedrooms have lighted closets that are almost room-width long. Central vacuum canister in garage; outlets throughout house & High-speed Ethernet cables from router entry to two of the bedrooms (~725 mbps download speed) Nice attic for partial storage, with drop down ladder access from garage. Built-in cabinetry in garage; location of large capacity clothes washer & dryer. Whole-yard irrigation Rain Master system with separate valve for automatic pool filling. Landscape up-lighting installed front and back 2023. Kitchen; stainless steel appliances: Bosch Dishwasher (age unknown) and Bosch French Door Refrigerator with separate Crisper drawer, 3-drawer freezer with icemaker (Nov. 2021); Cabinetry is custom made wood by Kitchen Maid; Microwave (2022); Scotsman bar-quality built-in extra icemaker; pantry storage/front entry closet; 2nd refrigerator/freezer in garage. New roof in 2019, Bosch French Door Refrigerator with separate Crisper drawer, 3-drawer freezer with icemaker (Nov. 2021); Microwave (2022).

1216 S View Drive, Siesta Key

$1,025,000
2 Beds 2 Baths A4573746 MLS 6480 BLDG.
Give yourself a gift of paradise on the pristine, crystal, sandy beach of Siesta Key. Dreamy, luxury living in your fifth floor, island get-away! This unit comes fully furnished! With 300 feet of Gulf Coast private beach, you will live your best life on the shimmering waters of the Gulf of Mexico. Take a moonlit stroll, enjoy sunsets at the beach, relax in your Heated pool, or chill from your screened balcony with an inviting tropical courtyard view. This premium condo has an assigned Carport, WEEKLY rentals (52 weeks a year), 2 lighted tennis courts, a lovely clubhouse, and it is a Gated community. Siesta Breakers caters to your comfort & style, with accommodating beach chairs and beautifully manicured grounds to compete with any other resort -style condo on the key. The interior is light and bright, with an updated kitchen and baths; interior washer & dryer, split plan bedrooms, and plenty of storage. The unit has an accompanied storage unit for all your beach toys. An elevator adds convenience and quick access to your condo. Siesta Breakers is a weekly rental complex with an on-site rental management office. Dining, shopping and a great marina (with jet skis and fishing excursions) are right across the street. The free Trolley takes you up and down the key every 15-20 minutes. Siesta Breakers is a great location with easy on & off access to the mainland. Siesta Key is a 14-minute drive to downtown Sarasota and nearby St Armands Circle.

6480 Midnight Pass Road Unit 503, Siesta Key

$1,022,000
4 Beds 4 Baths A4666929 MLS
Charming Coastal Oasis in the Heart of Siesta Key Nestled on a serene, tree-lined property, this inviting 4-bedroom, 3.5-bath beach-style home offers the perfect blend of tranquility, charm, and central location. Step into a spacious, light-filled living area with an open kitchen layout—ideal for hosting friends and making family memories. Freshly updated with new paint, gleaming quartz countertops, and stainless steel appliances, this move-in-ready home is designed for easy, coastal living. The open floor plan includes a spacious upstairs primary suite with French doors leading to a private balcony—your own quiet retreat. Three additional guest bedrooms are thoughtfully located on the first floor, including a separate guest suite with its own private entrance, offering comfort and flexibility. Step outside into your private backyard oasis featuring a beautiful pool and spa, fully enclosed with a lovely paver deck—perfect for relaxing, entertaining, or enjoying sunny Florida days in peace and privacy. There's still plenty of yard space to garden or play. Slip on your sandals for a short stroll to the world-famous Siesta Key Beach, ranked #1 in the U.S. by TripAdvisor, or bike to the charming Siesta Key Village with its eclectic mix of shops, restaurants, and entertainment. Don’t miss this peaceful, spacious retreat—your own slice of paradise on Siesta Key.

5151 Saint Albans Avenue, Siesta Key

$1,020,000
2 Beds 2 Baths A4592866 MLS Siesta Towers BLDG.
Searching for the ultimate tropical lifestyle? You found it with this beautiful, turnkey furnished, modern coastal retreat that is in a class in itself. Located on the idyllic northern end of Siesta Key, the open plan with two en-suite bedrooms provides comfortable casual living yet is ideally situated for entertaining. Your extensive balcony provides mesmerizing morning views of sparkling blue-green Gulf waters and evening views of spectacular sunsets. Leave your car behind as nearby are both the beach (0.8 miles to Beach Access #2) and vibrant Siesta Key Village (0.5 miles) with its vibrant, open-air restaurants and charming island boutiques. Both the condominium and the building have undergone a renaissance to reflect the best in modern coastal design. The condominium flooring is reminiscent of driftwood and sets the tone of the home. Cambria marble in the kitchen, soft-close white cabinetry with contemporary pulls and stainless steel appliances build on this idyllic coastal theme. Stunning wave tile, along with contemporary lighting and cabinetry, continues through both baths. Furnishings are sophisticated and stylish and will be left for the convenience of the buyer. Building amenities complete the lifestyle. Cool off in the Gulf-side newly renovated heated pool, with an outdoor kitchen area to use or fish at the dock, enjoy an exhilarating workout in the fitness center or enjoy happy hour near by or the beautiful sunset from your balcony. This is your opportunity to feel as if you are on vacation year-round.

4822 Ocean Boulevard Unit 4B, Siesta Key

$1,010,000
3 Beds 2 Baths A4649500 MLS
Newly adjusted price - an exceptional opportunity to own a charming beach retreat on Siesta Key minutes from world-famous Siesta Beach—consistently ranked among the best beaches in the U.S. With powdery white sands, crystal-clear turquoise waters, and unforgettable Gulf sunsets close by, this home captures the essence of relaxed island living. Located in the desirable, deed-restricted community of Siesta Isles, this three-bedroom, two-bath residence is set on a lushly landscaped, nearly 15,000-square-foot lot adorned with more than 40 mature palm trees, bromeliads, and a rare, show-stopping staghorn fern. The expansive property offers exceptional outdoor privacy, ample room for entertaining or recreation, and space to add a pool. Inside, the open-concept floor plan features generously sized rooms filled with natural light. A wraparound wall of windows in the living and breakfast areas frames serene views of the tropical backyard, creating a seamless indoor-outdoor connection. The renovated kitchen is thoughtfully designed with white quartz countertops, glass tile backsplash, and newer appliances, while a separate dining room provides comfortable space for gatherings. The primary suite includes an en-suite bath and a tranquil retreat feel. Two additional bedrooms offer flexibility, including a third bedroom with contemporary barn doors—ideal for a home office, den, or guest space. With a base flood elevation of 8'8" the home remained high and dry with no water intrusion during the storms; the elevation certificate and inspection certification are available. Additional highlights include a private, low-maintenance, six-foot fenced backyard, an oversized circular paver driveway with generous parking, and a two-car garage for storage and convenience. The home may be purchased turnkey furnished (with a few exclusions), making it well-suited as a beach getaway, seasonal residence, or income-producing property. Recent improvements totaling over $100,000 add peace of mind and value, including a metal roof (2022), HVAC system (2023), paver driveway (2022), six-foot PVC fencing (2020), and re-piped sewer and water lines. Just one mile from Siesta Village’s boutiques, dining, and live music—and a short drive to downtown Sarasota’s cultural attractions, farmers markets, and waterfront destinations—this property also offers long-term potential as a future residential building site due to its prime island location. With a voluntary HOA of only $200 annually and a newly improved price, this is a compelling opportunity to secure your place on Siesta Key. Schedule your private showing today and experience the island lifestyle you’ve been waiting for.

5432 Cape Leyte Drive, Siesta Key

$1,010,000
3 Beds 3 Baths A4592886 MLS Turtle Bay BLDG.
Enjoy the roominess of this full three-bedroom, three-bath updated condominium located at Turtle Bay on the south end of Siesta Key. This corner unit has a pleasant view of the Intracoastal Waterway, and Turtle Bay has boat docks available to rent, a fishing pier, outdoor grills, pool, spa, tennis and pickleball courts, along with beach access across MP Rd via the Tortuga parking lot. There are two en-suite bedrooms, plus a third bedroom with easy access to the third full bath. In addition to the water-view, glassed-in lanai, there is a second screened-in lanai extending 33 feet along one of the bedroom en-suites and breakfast room. This unit includes your own secured garage with plenty of storage. Plantation shutters throughout add to the tropical island-living lifestyle.

8735 Midnight Pass Road Unit 101B, Siesta Key

$1,010,000
2 Beds 2 Baths A4575897 MLS Boca Siesta BLDG.
Privately owned (deeded) boat dock & lift! A boater and beach lover’s delight. Extremely rare and fully remodeled end unit condominium with deeded boat dock and newer 13,000-pound lift located on the Siesta Key bayside with Gulf beach access. This two-bedroom, two-bath home is beautifully remodeled including new hurricane windows and sliding doors and is offered completely furnished. Large Sofa bed in great room provides additional sleeping accommodations. This unit also has an extended balcony overlooking the marina and gorgeous grounds. Enjoy a wonderfully maintained community that features a private marina that includes a newer seawall, docks and lift. The grounds are professionally landscaped to perfection and also include a tennis court with pickleball markings, large heated pool overlooking the Intracoastal Waterway and a large clubhouse for social gatherings and community events. Covered parking is provided for one car under the building plus outside guest parking is available. Boca Siesta has beach access with chairs directly across the street at the Sarasota Surf and Racquet Club, as well as on-property management for your convenience. Siesta Key Village is 1.8 miles away. Publix on Stickney and 41 is 2 miles away as well as Gulf Gate restaurants and shopping. Downtown Sarasota (Whole Foods, theaters, etc.) is 7 miles away. Truly a special opportunity.

5911 Midnight Pass Road Unit 108, Siesta Key

$1,005,000
2 Beds 2 Baths A4612864 MLS B BLDG.
Rarely available gulf front large 2 bedroom, 2 bath corner unit with a twenty six foot long balcony off the gulf facing living room. This unit is so expansive there is an additional lounge area adjacent to the dining room. The kitchen features wood cabinets, granite counters and stainless appliances. The kitchen was expanded into the eat-in area for additional storage. There is an additional private balcony off the twenty one foot long primary bedroom. It has two large north facing windows so it is a bright and sunny space. Large enough to create a sitting area. The guest bedroom currently holds 2 full size beds and has a walk in closet as well. Just across the hallway is a full bathroom, and the laundry room. The unit is unfurnished, but some furnishings can be purchased in a separate bill of sale. This is a Gulf to Bay community, with Boat Docks (7 slips currently available, lifts allowed) and an amazing private Beach. The sea oats, and sand dunes are reminiscent to the Siesta Key of the 70's. Resort-style amenities: two heated pools, tennis, pickle ball, billiards, 2 fitness center, clubhouse, social room, gas grills, Kayak racks, grilling patios, bike and Kayak storage and more. PET FRIENDLY (30 LBS). Tropical gardens add to the appeal of Island Reef and the owner was the one who created the beautiful landscape plan for the entire development. This community has an amazing on site staff in office throughout the week. Its a wonderful community and it's close to the three South end restaurants on the key. 1 parking space comes with the unit and it is fairly close to the buildings main entrance.

8770 Midnight Pass Road Unit B304, Siesta Key

$1,000,000
2 Beds 2 Baths A4692725 MLS Fishermans Cove BLDG.
Welcome to Fisherman’s Cove, a rare opportunity to own a beautifully updated top-floor beachfront condo located on Siesta Key! This 2-bedroom, 2-bath condo offers 1,132 square feet of coastal living space, including an enclosed lanai with breathtaking direct Gulf, beach, and sunset views. One of the standout upgrades includes stunning floor-to-ceiling glass sliders in the lanai, a $30,000 enhancement designed to maximize panoramic water views and natural light. Enjoy the perfect blend of beachfront serenity and boating lifestyle with direct Gulf frontage and Intracoastal Waterway access. Fisherman’s Cove features 900 feet of sandy beach, gated access, a heated community pool, kayak storage and dock, fishing from the docks, and 40 boat slips available to owners and renters at no charge, accommodating boats up to 30 feet with electricity included. Inside, the condo features tile flooring with sound buffer installation in the living room, custom wood kitchen cabinetry, granite countertops, stainless steel appliances, and a spacious walk-in utility closet with washer and dryer. The residence is being sold turnkey furnished, making it ideal for a primary residence, vacation home, or investment property. Additional conveniences include elevators, assigned parking, ample guest parking, storage, on-site management and rental office, and gas grills located along the lagoon side of the property. Experience the best of Siesta Key living with unmatched sunsets, private beach access, and resort-style amenities all in one exceptional waterfront community.

8900 Blind Pass Road Unit A306, Siesta Key

$1,000,000
3 Beds 3 Baths A4682650 MLS Excelsior BLDG.
New price - $100K less! Offered for the first time, this rare three-bedroom, three-bath waterfront villa at Excelsior’s coveted Beach-to-Bay community presents an exceptional opportunity to own one of only eight residences of its kind. Positioned on Sarasota Bay and the Intracoastal Waterway, the villa enjoys extraordinary privacy, peacefulness, and sweeping 180-degree water views from the expansive 36-foot lanai and most principal rooms. This light-filled corner residence lives beautifully like a single-family home, elevated above a private two-car garage and framed by windows on three sides. The open floor plan is spacious and airy, enhanced by vaulted ceilings in the living room, primary suite, and guest bedroom, hardwood flooring, and sliding glass doors that invite the waterfront setting indoors. A wood-burning fireplace adds warmth and character, while ceiling fans, custom window treatments, and 3M hurricane film on windows provide comfort and peace of mind. The updated kitchen opens seamlessly to the main living areas, creating an ideal space for entertaining or relaxed island living. The primary suite features a walk-in closet, a walk-in shower, and an updated bath. A new HVAC system, in-residence washer and dryer, and thoughtful upgrades throughout add to the villa’s move-in-ready appeal. Excelsior’s villas are uniquely situated directly on Sarasota Bay’s Intracoastal Waterway, with no other residences between you and the water. Only eight villas exist in total, four three-bedroom residences and four two-bedroom villas, making this a limited opportunity. Residents of Excelsior enjoy an unparalleled resort lifestyle with deeded beach access to Siesta Key’s world-renowned white sands, turquoise Gulf waters, and mango-colored sunsets. Amenities include two large, heated pools, two hot tubs, tennis and pickleball courts, shuffleboard, a fitness center, a library, a community room, and tranquil, tree-lined walkways with ponds and fountains. The fishing and lounging pier, grilling areas and picnic spaces are just moments away. The community is pet-friendly (small dogs), offers easy access to South Bridge and a short distance to Crescent Village, with free trolley service to Siesta Village. With a two-week minimum rental policy and on-site property management services available, the residence also offers attractive flexibility for seasonal or investment use. From morning experiences along the shoreline to breathtaking sunsets over the Gulf, every day on Siesta Key feels like a vacation. And when you're ready to explore beyond the island, downtown Sarasota is just a short drive away, offering world-class dining, arts and culture, including the Ringling Museum, Van Wezel Performing Arts Hall, and St. Armands Circle. Rarely available and exceptionally positioned, this waterfront villa captures the best of Siesta Key living, privacy, views, resort amenities and effortless access from beach to bay.

6275 Midnight Pass Road Unit 6275, Siesta Key

$1,000,000
2 Beds 2 Baths A4678534 MLS Crystal/708 BLDG.
RARELY AVAILABLE! Crystal Sands, Gulf Side GROUND FLOOR UNIT! Just out the door of your lanai and it is just steps to the pool and crystal white sands of Siesta Beach! This 2 bedroom, 2 bath split plan offers the best in beachside living. Beautiful, newly remodeled kitchen with extended peninsula is perfect for prep and entertaining! New appliances as well. Bathrooms are both nicely appointed with updated fixtures. Primary bath features separate dressing area/vanity and new shower with glass enclosure. Both bedrooms have walk in closets plus an additional double closet in the guest bedroom for extra storage or a perfect owner's closet. In addition, there is a large utility room with your own washer and dryer that allows even more storage. The generous lanai is accessible from the living and both bedrooms. Enjoy a peek-a-boo view of the gulf while enjoying your favorite beverage! Crystal Sands is one of the most desirable communities on Siesta Key and a highly sought rental destination. (2 week minimum) Situated perfectly right in the heart of Crescent Beach! There are 2 heated pools, assigned covered parking, community grills and an onsite management office. Gated access for extra security and comfort. Now is your opportunity to own a unit in this famous building at a great price! Rentals in place. Please contact agent for showing availability. All information believed to be accurate but should be verified by buyer.

6300 Midnight Pass Road Unit 110, Siesta Key

$1,000,000
3 Beds 3 Baths TB8459412 MLS
An exceptional opportunity on iconic Higel Avenue in Sarasota, where value is firmly rooted in land, location, and waterfront lifestyle. Situated on over 15,000 square feet, nearly half an acre, this property offers 92 feet of canal frontage and endless potential to renovate, expand, or build your dream coastal retreat.The existing residence features 3 bedrooms, 2 full bathrooms, and 1 half bath, providing immediate functionality while allowing flexibility for future plans. Whether envisioned as a personal residence, investment, or redevelopment opportunity, the setting alone is truly compelling.The location is unmatched. Just 0.6 miles to the vibrant Siesta Village, enjoy easy access to boutique shopping, acclaimed dining, and local nightlife. Beach lovers will appreciate being only 0.7 miles to the nearest beach access, with the main entrance to world-renowned Siesta Beach just over a mile away, celebrated for its powdery white sands and crystal-clear waters.This is more than a property. It is a rare chance to secure a premier canal-front parcel in one of Sarasota’s most desirable coastal corridors, offering a lifestyle defined by proximity to the water, the beach, and everything that makes Siesta Key extraordinary.

5036 Higel Avenue, Siesta Key

$1,000,000
2 Beds 2 Baths C7516381 MLS Siesta Breakers BLDG.
Fabulous Siesta Beach Condo at the Siesta Breakers #403 — Where Paradise Meets Profit Some properties are nice. This one is life-changing. Welcome to Unit #403 at Siesta Breakers — a rare, true beachfront end-unit perched directly on Crescent Beach, one of the most celebrated stretches of coastline on the planet. This isn't just a condo. It's a front-row seat to the Gulf of Mexico, every single day. Siesta Key's world-famous quartz-crystal sand stays cool even in the Florida heat — and 340 linear feet of it belongs exclusively to you and your guests. Across 5.6 lush acres, this gated community delivers a resort lifestyle that most only dream about. Inside, everything is already perfect. Bright. Open. Elevated. The open-concept living space flows effortlessly from designer interiors to a private balcony where sweeping Gulf views and legendary Siesta Key sunsets steal the show — every evening, without fail. The primary suite is a true sanctuary: a generous walk-in closet, an updated bath, and serene water views to wake up to. The guest bedroom is smartly designed for comfort, making it ideal for family or high-paying renters alike. It's offered completely turnkey — furniture, décor, and everything in between. Walk in and start living. Or start earning. Speaking of earning, the numbers speak for themselves. Unit #403 consistently generates $85,000+ annually in rental income, is already booked weekly through July 2026, and plugs directly into Siesta Breakers' highly sought-after weekly rental program. This isn't speculative income potential — the bookings are already in place. The community matches the lifestyle. Heated resort-style pool with tropical landscaping, Lighted tennis & pickleball courts, Private clubhouse, Security Gated Entrance, Secure under-building parking, Steps to island dining, boutique shopping & the free Siesta Key Breeze Trolley. Why #403 is the one: ? Prime beachfront end-unit — panoramic Gulf, pool & sunset views ? 340 ft. of private beach on world-renowned Crescent Beach ? Turnkey furnished & rental-ready from day one ? $85,000+ proven annual rental income ? Bookings already in place through July 2026 ? Low-maintenance luxury in a treasured, gated community Whether you're seeking your forever escape, a luxury vacation retreat, or a high-performing investment — this is the rare opportunity where all three align perfectly. Siesta Breakers #403 isn't just a purchase. It's a decision you'll never regret. Showings are only available on Saturdays between 2pm-4pm. Property is rented weekly thru July 2026.

6480 Midnight Pass Road Unit 403, Siesta Key

$1,000,000
3 Beds 2 Baths A4655333 MLS
Coastal Living Meets Elevated Views in Siesta Key Discover this unique waterfront retreat nestled on a saltwater canal in one of Siesta Key’s most sought-after neighborhoods. Featuring a 3-car garage and a main-floor primary suite, this home offers a flexible layout ideal for full-time living or a vacation getaway. The third floor boasts two additional bedrooms, a full bath, and a lofted overlook with views of the second floor’s open design. But the true showstopper? A rooftop observation deck with sweeping views of Big Pass and the Gulf of Mexico — the perfect sunset perch. Located on a street undergoing transformation with multiple new luxury builds, this property is a rare opportunity to enjoy now or reimagine later. At the end of the road, you’ll find a hidden beach enclave, offering a peaceful escape just steps from home. Whether you're drawn by the boating lifestyle, redevelopment potential, or panoramic rooftop vistas, this Siesta Key gem delivers coastal charm with untapped upside.

3737 Bayou Louise Lane, Siesta Key

$1,000,000
4 Beds 4 Baths A4633041 MLS
SIGNIFICANT PRICE IMPROVEMENT! Discover the rare opportunity to build or renovate on an exceptional .36-acre canal-front property located in the sought-after Sara Sands neighborhood on Siesta Key. Tucked away in a serene, upscale enclave just moments from the vibrant Siesta Key Village and the world-renowned Siesta Key Beach, this property offers the perfect blend of tranquility and convenience. The existing home—professionally remediated after flood damage—presents a unique opportunity for those looking to reimagine or completely rebuild. With ideal north-south exposure, this lot provides the perfect canvas for creating a custom-designed retreat that captures the coastal lifestyle. Boating enthusiasts will appreciate the private dock on a wide, deep-water canal, granting effortless access to the scenic Grand Canal and the Intracoastal Waterway. Whether you envision peaceful mornings on the water, lively gatherings by the pool, or simply relaxing in your personal oasis, the possibilities are endless. 5072 Higel Avenue is more than just a homesite—it's a lifestyle destination. Walk or bike to the #1 beach in the USA, then return to your private paradise. Enjoy world-class boating, fishing, fine dining, boutique shopping, and the cultural offerings of downtown Sarasota—all just minutes away. Bring your contractors, your architect, and your vision. This is your chance to create something truly special in one of Siesta Key’s most desirable locations. Don’t miss this exceptional opportunity. Schedule your private showing today.

5072 Higel Avenue, Siesta Key

$1,000,000
3 Beds 2 Baths A4607256 MLS
Nestled within the serene enclave of Siesta Key, where sun-kissed shores and vibrant island living converge, lies a haven of tranquility awaiting your arrival. Welcome to 49 Island Circle, a picturesque retreat with coastal charm and timeless elegance located on Palm Island in the heart of Siesta Key, steps away from the world renowned Siesta Key Beach Access #10. Enter into this captivating 3-bedroom, 2-bath pool home and instantly feel the embrace of island living. As sunlight dances through the windows, illuminating the terrazzo flooring with a subtle gleam, you will be enchanted by the seamless blend of classic style and modern comfort. Designed for both relaxation and entertainment, the heart of this home is its inviting living spaces. The spacious living room offers a cozy sanctuary for unwinding after a day of beachside adventures while the adjacent dining area beckons for memorable gatherings with loved ones. From morning coffee to evening cocktails, this home provides the perfect perch to savor every moment. As you step outside, a private lush oasis awaits with tropical landscaping that invites you to indulge in the ultimate outdoor experience. Immerse yourself in the refreshing waters of the sparkling, 40 foot courtyard pool, or simply unwind poolside with a good book as gentle breezes sway the palm trees. Beyond the confines of your retreat, the allure of Siesta Key beckons. Located just moments from the world renowned Siesta Key Beach, known for its powdery sand and crystal-clear waters, as well as the charming Siesta Key Village, brimming with eclectic shops, dining delights, and vibrant nightlife, each attraction presents an opportunity for adventure. Whether you are seeking a permanent residence, a vacation getaway, or an investment opportunity, 49 Island Circle offers the quintessential island lifestyle you have been dreaming of. Don't miss your chance to make this Siesta Key gem your own and embark on a lifetime of memories in paradise.

49 Island Circle, Siesta Key

$1,000,000
3 Beds 2 Baths A4590653 MLS 1237 BLDG.
“Living the Siesta Key Life” is waiting for you. DEEDED BOAT DOCK AND DEEP- WATER BASIN. Private single car garage too! This three-bedroom condo is totally updated, with a new kitchen with quartz countertops, breakfast bar and three pantries! New beautiful easy-care tile throughout. Step into the open floor plan for dining and casual living room with 20-foot ceilings and skylights to brighten your day! The living room and master bedroom open to a private 13 foot glassed and screened lanai. The second bedroom enjoys a private tropical garden view. The loft room is very versatile, it accommodates two beds, office space and workout equipment with an additional 11X26 storage room that affords you the luxury of saving your favorite seasonal and travel extras. The association has an amazing clubhouse, grills, large swimming pool, spa, tennis, pickleball courts and fishing pier. Gravitate to the quartz crystal white sand of world-famous Siesta Key Beach and enjoy swimming, walking, sunning and reading in paradise. Dine in casual and formal restaurants, listen to live music entertainment, great shopping, and free transportation to and from the village! This is your opportunity to live in the FUN FILLED “HOT SPOT” area of the Sunshine State and have it all!

1237 Dockside Place Unit 208, Siesta Key

$1,000,000
2 Beds 2 Baths A4589177 MLS Tower 1 BLDG.
Discover the ultimate island Jamaica Royale living experience with breathtaking views of the Gulf of Mexico and Siesta Key's famous powdery quartz sand. This stunning 2-bedroom, 2-bathroom unit is perfect for beach renters, investors, and families looking for their piece of paradise. Recently updated with fresh paint throughout, modern bathrooms, and granite countertops, this stylish and comfortable space is perfect for enjoying the island lifestyle. Step outside onto your balcony to enjoy the vibrant sunsets, or take a few steps and find yourself on the pristine beach. The building itself underwent a complete facelift in 2019, featuring hurricane windows, doors, UV sliders, and a fresh coat of paint. With a weekly rental minimum, this property presents a fantastic investment opportunity or vacation residence. On-site management ensures the smooth running of this island oasis, and with year-over-year increases in rentals, you can be sure your investment is in good hands. Amenities include three heated pools – one of which is located at the water's edge – gas grilling stations, shuffleboard, deeded beach access, and beachfront chairs. A short stroll down Siesta Key Beach brings you to tennis courts, pickle-ball, yoga, volleyball and a variety of other activities. Pet owners can enjoy the freedom of owning pets up to 100 lbs, and first-floor storage lockers provide extra convenience. This prime location is perfect for immersing yourself in island life, with fresh produce, seafood restaurants, and lively steel drum music just a trolley or bike ride away. Plus, easy access to Sarasota's mainland offers even more culture, shopping, and dining options. Don't miss this incredible opportunity to make the beach your personal playground, with all the comforts of home just steps away.

5830 Midnight Pass Road Unit 32, Siesta Key

$1,000,000
2 Beds 2 Baths A4584515 MLS 20 Whispering Sands BLDG.
Remarkable Opportunity at a Below Market Price for a Top Floor Beachfront Condo on Siesta Key! Have you been waiting for an opportunity that’s just too good to pass up? This spacious two bedroom, two bathroom home offers a versatile layout perfect for personal use, rental income, or a renovation project. Very clean and well maintained, this top-floor condo places you right on Siesta Key's powdery quartz sands and offers unobstructed, breathtaking views of the Gulf of Mexico. The balcony is approximately 100 square feet larger than the floors below and offers the ultimate in privacy and tranquility, allowing you the opportunity to enjoy the breathtaking sunsets while watching the soothing waves roll in without interruption. To make this offer even better, there are new impact windows and sliding doors, water heater installed in 2019, HVAC installed in 2021 and new front door will be installed with exterior concrete restoration project that is underway. There is also an additional storage room with a large private storage locker just outside the front door. Whispering Sands is a resort-style community with amenities that include two swimming pools, two clubhouses, exercise rooms, a picnic area with a tiki hut and grills, kayak and canoe storage, a large lagoon, meticulously landscaped grounds and more than 800 feet of private beach. Situated in the heart of world-renowned Siesta Key Village, you'll have private access to the island's vibrant dining, shopping and entertainment scene along with all the services you'll need to enjoy an island lifestyle. And you’ll be just minutes from the many cultural attractions Sarasota offers such as the Ringling Museum, Selby Botanical Gardens, the Florida Studio Theatre, Sarasota’s own Opera, Orchestra and Ballet, the Van Wezel Performing Arts Center, Mote Marine, Sarasota Jungle Gardens, world-class golf courses, professional sports teams and much more. Whether you're seeking a vacation retreat, investment property, or year-round beachfront living, this Whispering Sands condo offers a remarkable opportunity. Don't miss the chance to see this incredible below-market value!

20 Whispering Sands Drive Unit 1205, Siesta Key

$1,000,000
3 Beds 2 Baths A4571168 MLS
Two separate lots! This home, quaint, charming, loved, is located just over the bridge to the heart shaped Palm Island, the "HEART OF SIESTA KEY". A short walk to the private community access #10 to the crystal sands of Siesta beach. Homeowner is motivated and will respond to all offers! The home has everything one needs to live the island lifestyle, 3 bedrooms, two full /one 1/2 baths, sitting area, separate living room and enclosed “Florida or All Season” room. The home is surrounded by original palm trees and tropical gardens. But it is the double lot that this home is situated on which adds so many options and potential. Move into this home as it is, use it as an investment property, or remove the current home and either build two homes on the two buildable lots, or build your new dream home. A quick walk to the restaurants and shops of Siesta Village and even a shorted walk to Siesta Key Beach. Priced under recent appraisal value.

5355 Calle Florida, Siesta Key

$999,000
2 Beds 2 Baths A4577353 MLS 19 BLDG.
Catch dazzling Florida sunsets from this 4th floor condo in the North Tower of Whispering Sands. Enjoy the luxury of having never-ending FULL Gulf views plus 800 ft. of private crystal quartz beach below. That is not all, from this 55+ condo community, you can walk into Siesta Village to restaurants, bars, and shopping. The 2 bedroom/2 bath condo has been owned by the same owner for 19 years, and rented by her for the previous 8 years, so lovingly maintained by the same person for 27 years. The unit has hurricane impact windows, and sliding glass doors in the living room and Master bedroom leading out to the lanai, plus impact sliders on the lanai for added protection. Kitchen appliances were replaced in 2020 and 2021. The AC was replaced in July 2023, and hot water heater in 2015. With all this completed, it's now time for a new owner to come along, and make it their own. Whispering Sands has beautiful landscaped grounds, 2 heated pools, clubhouse, fitness room, beachside grills, tiki hut, canoe/kayak storage racks, and rare on Siesta Key, their own private beach. The North and South Towers share the lounge in between the two towers with a kitchen, TV, Billard table overlooking the pool, Gulf, and beach. In addition to that, the community has an onsite manager, and a secured fob key system for access to the buildings and clubhouse. A common laundry is on each floor. This Gulf front condo has the best of both worlds with breathtaking water views, incredible sunsets to lower your stress levels, a private beach with no hassle finding a parking place, and the ability to walk into Siesta Village for your entertainment. Downtown Sarasota is only a short distance away for even more to offer in restaurants, the arts and culture activities.

19 Whispering Sands Drive Unit 404, Siesta Key

$995,000
2 Beds 2 Baths A4607051 MLS Gulf & Bay BLDG.
Exquisite, updated, turnkey-furnished two-bedroom, two-bath beach oasis! Located in the heart of Siesta Key at the exclusive upscale Gulf & Bay Club. Featuring high-end detailed finishes and interiors professionally crafted to perfection. This unit is a rare find in the highly sought-after B Building with beach access just steps away. Enjoy breathtaking sunsets from your personal enclosed veranda. The sandy white powder stretches 800 feet across this pristine 32-acre meticulously cared-for tropical community. Enjoy the comfort of 24-hour gated security, heated pools, fitness center, dry saunas, hot tub, tennis courts, racquetball, and pickleball courts. Multiple barbecues and tiki hut picnic areas are great for entertaining your guests. The clubhouse has a library, bar, pool table, and TVs for your enjoyment. Electric car charging stations and on-site car wash. You are moments away from Siesta Village to enjoy outdoor dining with live music, specialty shopping, and more! Take a short trip to downtown and discover theater, art, and fine dining. This is the island resort lifestyle you have been looking for; don't let your chance of fine beach living slip away.

5780 Midnight Pass Road Unit 504, Siesta Key

$990,000
2 Beds 2 Baths A4679696 MLS Gulf & Bay BLDG.
Experience Luxury Living on Siesta Key! Welcome to the Gulf & Bay Club Condominium perfectly situated on the pristine shores of Siesta Key. This stunning Gulf-front property offers unparalleled beach living, making it the ultimate coastal retreat. This unit is offered turnkey furnished, ready for immediate enjoyment. 2-bedroom, 2-bathroom residence presents an expansive floor plan highlighted with a new kitchen featuring new appliances, granite countertops,new cabinets, and refined accents. The kitchen seamlessly transitions into a spacious living area with enclosed lanai adding additional space in your living area. Offered turnkey furnished with a sophisticated beach ambiance. Master bath featuring dual sinks, quartz countertops and large walk-in shower. The additional bedroom for your guests includes an ensuite bath which offers ample space. Door lock, gate, building, and beach access. Plus an owner’s storage closets for rental convenience. This property serves as a tranquil retreat in an exceptional location whether you're seeking a permanent residence, a vacation getaway, or a profitable rental property. The building boasts an array of amenities designed to elevate everyday living, including onsite management for added convenience. Two electric vehicle charging stations that are available, 3 Large heated pools w/wifi including 1 lap pool, 800ft Private soft white sandy beach, 6 Tennis courts including 1 Har-Tru court, 6 Pickleball courts, Basketball/Racquetball/Pickleball courts, Shuffleboard court, Organized seasonal golf for men and women, State of the art fitness center, including free weights and yoga room, 6 Dry saunas, hot tub, 2 Clubhouses – library with books, bar, pool table and TV’s, Numerous social activities during season, World famous Siesta Key Beach – #1 by TripAdvisor, Directly on the beautiful Gulf of Mexico, Spectacular sunrises and sunsets

5780 Midnight Pass Road Unit 207, Siesta Key

$990,000
2 Beds 2 Baths A4637738 MLS 20 BLDG.
***PRICE REDUCED*** This stunning beachfront condo offers a rare combination of luxury, convenience, and breathtaking natural beauty. Nestled on the powdery soft white sands of Siesta Key Beach, this end unit features an additional window which floods the space with an abundance of natural light and provides panoramic views of the sparkling Gulf of Mexico. This condo isn’t just a home; it’s a lifestyle. It comes fully furnished with exquisite turnkey furnishings the likes of Waterford, Mackenzie-Childs, Serena & Lilly, Pottery Barn, Rugs As Art, and more. Every detail has been thoughtfully curated ensuring both elegance and ease of use so you can settle in and start enjoying the coastal lifestyle right away. As you enter, you will be greeted by an open-concept design and fabulous views of the Gulf of Mexico. The kitchen features stainless appliances along with quartz countertops, custom cabinetry and a large breakfast bar perfect for casual dining. Just off the kitchen, French doors lead you into a guest retreat spacious enough for the king bed or you can separate the Pottery Barn base into two twin beds. The elegant guest bath with custom tiled shower and quartz countertops will have your guests planning their next visit before they even leave. Experience the ultimate in beachfront luxury with nearly forty feet of dining and living space showcasing the finest gulf views. Next, imagine waking up to the sound of waves and endless views made possible by the large glass sliders in the master bedroom overlooking the private beach. Last, but certainly not least, is the ensuite which has even more custom cabinetry, a double vanity and custom tiled walk-in shower. Additional features include impact windows and doors, motorized blinds, plantation shutters, remote controlled ceiling fans, new (nearly silent) HVAC system and additional storage just outside your front door. This premier 55+ community also includes a beachfront pool, a clubhouse pool, community rooms, fitness room, kayak storage, tiki hut with grilling area, a lagoon and a private gate leading right into the heart of Siesta Key Village, which is known for its vibrant dining, shopping, entertainment and all the conveniences needed for an island lifestyle. You're also just minutes from Sarasota's cultural attractions such as the Ringling Museum, Selby Botanical Gardens, Florida Studio Theatre, Sarasota Opera, as well as boating, fishing, golf courses and professional sports venues. Whether you're seeking a vacation retreat or year-round coastal living, this turn-key furnished condo has it all. Contact me today to schedule your private tour and start living the Siesta Key lifestyle you've always dreamed of.

20 Whispering Sands Drive Unit 306, Siesta Key

$990,000
3 Beds 2 Baths A4633981 MLS
A HURRICANE SURVIVOR SUPERSTAR--NO DAMAGE HERE!! This CHARMING COASTAL HOME invites you to live the ultimate seaside dream! This home has been IMPECCABLY MAINTAINED and is in a GREAT LOCATION! Only 1.4 miles to the ICONIC #1 rated SIESTA KEY BEACH and 2.4 miles to SIESTA KEY VILLAGE. Surrounded by vibrant, beachy charm, this home offers the perfect escape- where relaxation meets adventure. Your new home offers tranquil living in a secluded serene ambience just a few minutes away from all that SIESTA KEY has to offer. This home has a split floor plan and offers a seamless transition between indoor and outdoor living with four sliders to the beautiful, huge caged pool lanai from the primary bedroom, the dining room, the family room and another bedroom. This lanai is quite unusual with a very large covered area making it ideal for entertaining regardless of weather! Picture sipping your morning coffee or evening cocktail on your spacious private, secluded lanai. The large impact resistant windows and sliders let the SUN SHINE IN to brighten your every day here in PARADISE! This home has: ALL NEW HURRICANE IMPACT WINDOWS, SLIDERS AND GARAGE DOOR, HVAC was replaced 3/23, EPOXY SEALED GARAGE FLOOR and an ALUMNINUM ROOF. There is a huge walk-in shower in the primary ensuite with a rainfall shower head. A new Bosch dishwasher was just installed in February. Beach more, worry less! Here are some of the highlights of living here from the lovely and active owners: "We love living at the end of a canopy street with it's lush green trees. Not having neighbors on one side of us has made for a very peaceful and quiet experience. Sitting outside with all of the Eureka palms makes you feel like you are in your own oasis. The covered lanai space has been the very best feature. The lanai covering allows us all to be outside in the sun or rain and it is delightful to be able to walk inside to many rooms, including the bathroom. We love the kitchen window with the counter outside. The heated pool has been enjoyed for health and healing. Having two inside gathering spaces and three interior places to eat have been a great detail. Being able to go to Siesta Beach or Turtle Beach in minutes by either walking, car or biking is such a great benefit! Glebe park is about 1/4 mile away and has basketball, baseball, soccer, playground, picnic area and a nice walking track. It is a great place for children and adults. We love to ride bikes to the Village and grab something to eat at the many fine restaurants. Date night to the Made in Rome Gelato---ahhh, it's like you are in Italy. We enjoy riding bikes to Turtle Beach and getting lunch at the grill down there. Every sunset at Siesta Key is the best with multicolor differences every night." This home is perfect for a year-round resident, a snowbird home or an investment property. COME TAKE A PEEK AT A GREAT VALUE ON SIESTA KEY AND MAKE AN OFFER ON YOUR OWN SLICE OF PARADISE! Remember, Beach days keep the doctor away!

5159 Oakmont Place, Siesta Key

$985,000
2 Beds 2 Baths A4678810 MLS Siesta Towers BLDG.
Major Price Reduction and what an opportunity! In a word...Stunning. Introducing this fully renovated and stylishly furnished 9th floor condominium offering refined Gulf-front living on Siesta Key, where breathtaking sunsets and gentle Gulf breezes set the tone for everyday life. This beautifully redesigned 1,435-square-foot residence features two bedrooms and two full baths and was completely renovated in 2020 with quality finishes and thoughtful details throughout. The open, light-filled layout creates an elegant yet inviting coastal retreat, perfect for both quiet evenings and entertaining guests. With a split bedroom floorplan, your guests will enjoy their ensuite bathroom and slider doors leading to the expansive patio overlooking the Gulf and it's forever views. The primary suite has it's own private balcony and water and Island views expand from downtown Sarasota all the way up to mid Longboat Key. Boat watching is a must! The building is exceptionally well maintained with strong financial reserves and stands apart as association fees have actually decreased, reflecting extensive completed improvements designed to enhance storm protection and long-term value. A brand-new seawall is currently being installed and is already fully funded, providing additional peace of mind. Residents enjoy an impressive array of amenities, including a Gulf-front pool ideal for watching the sun melt into the horizon, an outdoor kitchen with grills for sunset gatherings, a beautifully appointed social room, a fitness room with equipment, a spacious bike room, and a dedicated fishing room for rod and gear storage. Each floor has a laundry room with storage and you may also install an approved washer and dryer in your apartment. A new fishing pier and social sunset pier are being completed, offering the perfect waterfront setting for entertaining, relaxing, and savoring evening skies painted in coastal hues. Ideally located just moments from Siesta Key Village, this exceptional residence places coffee, wine, shopping, and dining just steps away, blending relaxed island charm with an elevated Gulf-front lifestyle. Move right in - turnkey furnished!

4822 Ocean Boulevard Unit 9A, Siesta Key

$985,000
3 Beds 3 Baths A4666867 MLS
One or more photo(s) has been virtually staged. Tucked away at the end of quiet Estrada De Costa, a single lane road with just three homes, this unique and spacious Siesta Key 3 bedroom/3 bath lakefront property offers rare privacy, flexibility, and charm. The home was expanded in 2001, the property includes a 2 bedroom/2 bath main house, and a fully equipped one bedroom/one bath separate suite with its own private entrance, cozy living room, kitchen, walk-in closet, and screened porch with tranquil water views. Ideal for multigenerational living, guest accommodations, or income potential. Saltillo(Mexican) tile flooring flows throughout both living spaces and adds character and charm to every room, while the open layout flows seamlessly for comfortable everyday living. Sliding glass doors on the water side fill the rooms with natural light. The house did have water in the home after Hurricane Helene, so the owner completed some thoughtful and stylish renovations such as Shaker cabinets, quartz counters, subway tile backsplash, all new LG stainless steel appliances, new AC, and hot water heaters in both living spaces, and solid paneled doors throughout. New roof in 2022, and drain pipes lines in 2024. Located on Lake Rittwood, a serene neighborhood pond teeming with tilapia, turtles, ducks and birds, this home is a retreat. Stroll into Siesta Key Village, or catch sunset views at the Big Pass/Gulf public access at the West end of Givens St. and Ocean Blvd. This home offers the end-of-the-road seclusion, but still close to the wonderful activities of Siesta Key and Sarasota. Whether you're hosting guests, housing extended family, or exploring rental potential, this unique layout offers flexible living options rarely found on the Key.

4830 Estrada De Costa, Siesta Key

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