Location: Sarasota , 34242
Do Not Show Listings
5830 MIDNIGHT PASS RD #3, SARASOTA, FL 34242
$649,0002 Days on yellowkey MLS ID: A4697756
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 728 Built: 1960 Tax: $3,964 (2025)Community: Jamaica RoyaleVilla
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,964
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Wonderful gulf side attached villa in an all ground level association, so no milestone inspections required. This completely updated, open floor plan. Upgrades galore!! 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!
Listing is courtesy of: TIDELINE REAL ESTATE BROKERS (941-587-1669)
Listing Agent: Steve Cavanaugh (941-587-1669)
4708 OCEAN BLVD #E4, SARASOTA, FL 34242
$2,199,00072 Days on yellowkey MLS ID: A4689440
REDUCED by $91,000 (4.0%) on 05/21/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2277 Built: 1981 Tax: $16,662 (2025)Community: Windward PassageCondo
Taxes:$16,662
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Middle School: Brookside Middle
Remarks: Expansive floor-to-ceiling sliders open wide to welcome refreshing Gulf breezes and showcase unobstructed, panoramic water views, turning your open-floorplan living space into an indoor/outdoor oasis. With over 2,300 square feet, this light-filled condominium lives like a private home suspended above shimmering waters. The gourmet kitchen is both elegant and functional, featuring quartz countertops, custom wood cabinetry, and premium appliances, including a Thermador refrigerator and freezer, Wolf double ovens, Wolf microwave, and a Thermador induction cooktop. Panel-ready finishes, a built-in beverage cooler, and exceptional storage make this space ideal for both everyday living and entertaining. Rich acacia engineered wood flooring adds warmth and sophistication throughout the main living areas. The spacious primary suite captures sweeping Gulf views and offers a serene escape, complete with a beautifully renovated spa-inspired bath featuring split vanities and a large walk-in shower. Two additional bedrooms and stylishly updated baths are thoughtfully positioned on the opposite side of the residence for added privacy. Impact-rated windows and sliders provide peace of mind, eliminating the need for hurricane shutters. A private two-car garage with ample storage adds to the home’s convenience. Windward Passage features a Gulf-side pool, lushly landscaped grounds, and a pet-friendly setting. Perfectly positioned on the sought-after north end of the key, you’re just a short walk to the Village for charming boutiques, dining, and live entertainment.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Mina Johnson (608-345-7089)
6415 MIDNIGHT PASS RD #211, SARASOTA, FL 34242
$799,900188 Days on yellowkey MLS ID: A4675481
REDUCED by $50,000 (5.9%) on 06/13/2026
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 2358 Built: 1975 Tax: $7,544 (2025)Community: AnchorageSpa: NoCondo
Taxes:$7,544
Remarks: Huge opportunity to own a spacious 2,400 sq ft, 3 bedroom condo on Siesta Key with an aggressive, new price drop! Now being offered at $799,900 - an unbelievable $339.22 per square foot (vs recent SK sales average of $460 per square foot). This is a fabulous family investment with plenty of room to sleep 8 people (Note: a 4th bedroom could easily be added). This condo has brand new floor-to-ceiling high impact hurricane sliders that run the entire length of the condo and open to a full 95’ lanai for a nice open-air feeling. Allow your family to enjoy your new vacation home, then use the successful in-house rental program to make additional income for yourself. The best of both worlds! Gated-community amenities abound here: both private beach access and intracoastal access with use of free boat slips and kayak racks. One of the largest heated pools on the Key. Brand new pickleball and tennis courts. Tropical landscaping that includes areas for nice seating on the intracoastal, outdoor grilling and picnics, shuffleboard, cornhole, and basketball goal. Fitness center and party/event space. Wheel-chair accessible property. You can go from car to kitchen with no steps! This condo offers a very desirable split floorplan with the primary bedroom on one end and the other two bedrooms on the opposite end with 2 distinct heating/cooling systems. Also includes 2.5 baths with both a tub and shower option. Generous closets in each room, plus a large owner’s closet, beach closet and unique private, full storage closet in hallway next to condo. Whether you are searching for a spacious family getaway, a peaceful primary residence, and/or a high-performing rental, this rare offering delivers.
1260 DOLPHIN BAY WAY #404, SARASOTA, FL 34242
$1,395,000204 Days on yellowkey MLS ID: A4673762
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2200 Built: 1997 Tax: $12,793 (2025)Community: Dolphin BaySpa: YesCondo
Taxes:$12,793
Remarks: ENJOY SERENE INTRA-COASTAL WATER VIEWS from this this 4th floor, end unit, 3 bedroom, 3 full bath condo at Dolphin Bay. This community lives life to the fullest! Lots of social activities and friendly and caring neighborhood. Take a new look and enjoy the fresh new decor and new high impact windows and sliders, all added in 2025! Reduced condo fees. This meticulously maintained condo lives like a single family home with charm and character. The kitchen was custom built by Yoder Construction, a well-known local company, highly respected for their craftsmanship. Living room and dining area are bright and spacious. The large primary bedroom has a walk-in closet and ensuite with shower and separate soaking tub. There are two other ensuite bedrooms. All three bedrooms have California Closet systems. All windows have custom plantation shutters, adding to the charm and comfort of this amazing condo. You will want to spend your day on the light filled lanai, perfect for entertaining or simply relaxing. Dolphin Bay is a highly desirable, gated, pet friendly, 50-unit complex with a fun filled community atmosphere with three Har-Tru tennis courts, an active clubhouse, fitness center, pool and spa, day dock, fishing pier and kayak access. Dolphin Bay is well maintained with a freshly updated exterior and new elevators in 2024 and beautifully landscaped grounds. Just a short walk to the world famous, white crystal sands of Siesta Key beach.
1240 DOLPHIN BAY WAY #401, SARASOTA, FL 34242
$1,199,000268 Days on yellowkey MLS ID: A4658380
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2200 Built: 1998 Tax: $12,546 (2025)Community: Dolphin BaySpa: YesCondo
Taxes:$12,546
Remarks: Huge Price Reduction!!! Fourth-floor end unit offering breathtaking views of the intracoastal waterway, featuring three spacious bedrooms and three full ensuite baths. Newly installed luxury vinyl plank flooring graces the entire unit. The expansive glassed lanai boasts recently replaced sliding doors, complete with accordion shutters on the inner doors and impact-resistant glass on the outer ones. The kitchen has been thoughtfully opened up and reconfigured for optimal enjoyment. The living and dining areas are bright and roomy. Dolphin Bay is a sought-after, gated, pet-friendly community with only 50 units, each having its own private underbuilding garage, and well-known for its vibrant atmosphere. Amenities include three Har-Tru tennis courts, an active clubhouse, fitness center, pool and spa, day dock, fishing pier, and kayak access. The complex is well-maintained, with a freshly updated exterior and new elevators in 2024, set amidst beautifully landscaped grounds. Just a short stroll to the world-renowned, white crystal sands of Siesta Key beach. Condo fees at Dolphin Bay are being lowered in 2026.
Listing Agent: Ethel Lovelace (941-586-7390)
1269 DOCKSIDE PL #115, SARASOTA, FL 34242
$825,000268 Days on yellowkey MLS ID: A4656792
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1217 Built: 1982 Tax: $6,667 (2024)Community: Harbour TowneSpa: YesCondo
Taxes:$6,667
Tax Year: 2024
Remarks: This spacious condo has easy access to Siesta Key Beach and a DEEDED 25-FOOT BOAT SLIP WITH A LIFT!! There is water and electric to the slip (#38). Yes, this is a rare opportunity to have both your boat and a nearby world-famous beach in a nicely laid out two-bedroom, two-bath turnkey furnished condo. The master bedroom has views of the harbor while the guest room has a peaceful garden view. This condo features tile flooring throughout with both HVAC and appliances that are only a couple of years old. The roof was replaced in November 2021, and the unit has a one-car garage with storage above as well as a dedicated parking space in front. In addition, this unit has one of the few private outdoor decks in the community. Harbour Towne offers fantastic amenities, including a clubhouse, heated pool, spa, and tennis/pickleball courts. Enjoy the village by day or evening for great dining, shopping and live music. A complimentary trolley runs by the complex on a regular schedule in season. This is a great place to live and play! Look no further, this is where your fun-filled life begins.
1255 E PEPPERTREE DR #201, SARASOTA, FL 34242
$499,000317 Days on yellowkey MLS ID: A4661191
2 Days Off yellowkey (back on 6/8/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1460 Built: 1972 Tax: $5,890 (2024)Community: Peppertree Bay ISpa: NoCondo
Taxes:$5,890
Remarks: Under contract-accepting backup offers. Move in ready AND priced to sell quickly! Don't miss the chance to own this beautifully updated turnkey furnished 2-bedroom condo at Peppertree Bay, available at an unbeatable price! Experience resort-style living in this bayfront and beachside community. The interior boasts an open floor plan with spacious, welcoming rooms, tile and luxury vinyl plank flooring, and a generous 29-foot lanai. Peppertree Bay offers luxurious amenities, including under building parking, private beach access, two heated swimming pools, tennis and pickleball courts, two clubhouses, a fitness center, and a fishing pier. It’s like a vacation every day! When you want a change of pace, leave your car behind and take the trolley to all the wonderful restaurants and shopping Siesta Key has to offer. With onsite management and a rental desk, this Peppertree Bay condo serves as an ideal coastal getaway or a smart investment choice. Don’t let this one get away.
6703 MIDNIGHT PASS RD #101, SARASOTA, FL 34242
$424,90044 Days on yellowkey MLS ID: A4693235
REDUCED by $15,000 (3.4%) on 06/23/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 964 Built: 1974 Tax: $4,605 (2025)Community: Sea WindsCondo
Taxes:$4,605
Remarks: LOCATION, LOCATION, LOCATION – Live the “beach life” and a wonderful investment opportunity in beautiful Siesta Key, Florida! Enjoy your own piece of paradise at Sea Winds Condominium, Unit 101. This inviting first-floor, turnkey- “fully furnished”condo offers 2 bedrooms, 2 bathrooms, and beautiful views, all within a short walk to the world-famous beaches of Siesta Key. Meticulously decorated and thoughtfully designed, this charming condo features a comfortable living space with easy first-floor access. The unit comfortably sleeps 7 guests. The spacious primary bedroom includes a queen bed, tv, and dedicated workspace, making it ideal for remote work or extended stays. The second bedroom features a trundle bed with an additional matching twin bed, along with its own television. The living room offers additional sleeping accommodations with a queen-size sleeper sofa. The fully-equipped kitchen provides everything needed for everyday living and entertaining, while the dining area seats 6 comfortably. An adjustable coffee table offers seating for two additional guests. The unit includes a designated parking space directly in front of the condo, along with additional guest parking. Cable, water, and sewer are included in the Condo fee. Step outside to your own large, fully fenced private patio oasis featuring a Weber grill, a dining table with umbrella seating for six, and a relaxing conversation area with chairs— perfect for enjoying the Florida sunshine or entertaining guests outdoors. Residents of Sea Winds Condominium enjoy access to a heated community pool with lounge chairs, umbrellas, outdoor shower, and bathrooms for year-round enjoyment. Additional amenities include bicycle storage room, a social room for gatherings, barbeque grill and two shared laundry facilities. For added convenience, the condo also includes beach chairs, beach towels, and a rolling beach storage cart and a large storage unit on the 2nd floor. Beyond the comfort of the condominium, you are only a five-minute walk from the pristine quartz sands of Siesta Key Beach, consistently ranked among the top beaches in the United States. Spend your days soaking up the sun, strolling along the shoreline, or enjoying the spectacular sunsets for which Siesta Key is famous. Leave the light on in the condo, because when you walk back from the beach at night, it feels like a beacon calling you back. Just a short walk away, you’ll find the South Village area featuring restaurants, boutiques, beach bars, ice cream shops, and rental companies offering fishing equipment, boats, kayaks, bicycles, and passenger golf carts. A daily trolley service with stops directly in front of the Sea Winds complex provides convenient access to Siesta Key Village and other island attractions. Being well built all above Sea Level, this inviting two level complex has enjoyed being water free from any storm or hurricane since it was built. Recent community improvements include:• New roof (2024)• Newly renovated swimming pool (2025)• New storm drainage and sewer lines (2025)• Newly paved and striped parking area (2026)Do not miss this incredible opportunity to enjoy coastal living at its finest. This Sea Winds Condominium offers the perfect combination of relaxation, convenience, and adventure in one of Florida’s most sought-after beach destinations. More important though, to truly appreciate this little gem, come and see it for yourself. This unit is precious and deserves to be loved.
Listing is courtesy of: FINE PROPERTIES (941-782-0000)
Listing Agent: Sean Hickey (941-587-4244)
6140 MIDNIGHT PASS RD #606, SARASOTA, FL 34242
$1,279,00031 Days on yellowkey MLS ID: A4694184
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1521 Built: 1967Monthly Fee: $1,354 Tax: $13,588 (2025)Community: Horizons WestSpa: YesCondo
Taxes:$13,588
Remarks: Nestled on the renowned shores of Siesta Key, Horizons West offers a truly exceptional waterfront living experience where breathtaking panoramic views and unforgettable sunsets become part of everyday life. This meticulously cared-for two-bedroom, two-bathroom residence, elevated on the sixth floor, delivers unparalleled luxury and privacy in a home that has never been in a rental program, resulting in exceptionally minimal wear and tear. Following a comprehensive top-to-bottom renovation that stripped the unit to its concrete box, every inch of this residence reflects the pride of true ownership with timeless, sophisticated design. The gourmet kitchen and bathrooms feature custom Harlan solid wood cabinetry sourced from Indiana, sleek granite countertops, and a premium suite of KitchenAid stainless steel appliances. Modern infrastructure is seamlessly integrated throughout, including Cat 6 data outlets, a commercial-grade PakEdge Wi-Fi router, and a whole-home surge protector. Comfort is guaranteed with a brand-new HVAC system installed in July 2025, complete with an air scrubber for active air purification. The home is an audiophile’s dream with a built-in multi-zone sound system featuring Vienna Acoustics speakers and a Marantz receiver. Elegant touches abound, from recessed LED and runway lighting to motorized Hunter Douglas window treatments and custom California Closets. Offered turnkey and fully furnished, the residence includes high-end pieces like an American Leather sofa and Westin Heavenly Bed® mattresses, along with the rare convenience of a roughed-in space for an in-unit washer and dryer. Horizons West spans 11 acres with over 300 feet of deeded beach access, a beachside pool and spa, and a serene bay-side park with a day dock. This is a rare opportunity to own a residence finished to the highest standard on the world-renowned shores of Siesta Key. Welcome home.
Listing is courtesy of: ENGEL + VOELKERS SARASOTA (941-388-9800)
Listing Agent: Brian Partie, Jr, Pa (941-544-8298)
6287 MIDNIGHT PASS RD #201, SARASOTA, FL 34242
$630,00021 Days on yellowkey MLS ID: A4695909
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1401 Built: 1982 Tax: $6,836 (2025)Community: Excelsior Beach To Bay 6Condo
Taxes:$6,836
Remarks: Beautiful Excelsior Beach to Bay - absolutely gorgeous condo complex and beautifully refreshed and remodeled unit. This condo lives large - plenty of room to relax and not feel cramped on a rainy day! Jumbo sized Master bedroom with private, totally remodeled and updated bath and ample sized walk in closet. Second bedroom holds two queen sized beds for multiple guests and has access to secondary, totally remodeled bathroom that includes stacked washer and dryer. Plantation shutters. New luxury vinyl flooring throughout - no carpet to catch our beautiful Siesta Key sand! Covered and enclosed lanai area off the living room. Condo complex offers access to not only the intracoastal but more importantly your private beach area on the Gulf side. Newer appliances in kitchen. New air conditioning and water heater.
Listing is courtesy of: COLDWELL BANKER REALTY (941-907-1033)
Listing Agent: Kimberlie Macdonald (941-928-1953)
9150 BLIND PASS RD #206, SARASOTA, FL 34242
$874,99933 Days on yellowkey MLS ID: C7526359
REDUCED by $25,001 (2.8%) on 06/22/2026
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1710 Built: 1975 Tax: $9,204 (2025)Community: Fishermans HavenCondo
Taxes:$9,204
Remarks: Some photos have been virtually staged. Welcome to Fishermans Haven on South Siesta Key, where coastal comfort and modern updates come together in this beautifully renovated 3-bedroom, 3-bath waterfront condo. Offering over 1,700 square feet of bright, open living space, this residence has been fully updated from top to bottom with new flooring, a beautifully redesigned kitchen, updated bathrooms, and stylish finishes throughout. Natural light pours into the living areas, creating a warm and airy feel, while the private patio offers peaceful water views that perfectly capture the relaxed island lifestyle. Located right next to Turtle Beach and just a short drive from the world-famous Siesta Key Beach, you’ll enjoy easy access to beaches, boating, kayaking, restaurants, and shopping. The community features great amenities including a heated pool, sundeck, grilling area, kayak and bike storage, and elevator access. Additional updates include a new HVAC system and hot water tank replaced in 2026. Community improvements are also underway and expected to be completed this summer, including pool restoration, exterior painting, and parking lot repairs making this an even more attractive opportunity to own your piece of paradise on Siesta Key.
Listing is courtesy of: RE/MAX PALM REALTY (941-743-5525)
Listing Agent: Taylor Brady (239-896-6433)
19 WHISPERING SANDS DR #201, SARASOTA, FL 34242
$899,000151 Days on yellowkey MLS ID: A4679748
REDUCED by $51,000 (5.4%) on 05/15/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1464 Built: 1973Monthly Fee: $1,440 Tax: $3,007 (2025)Community: Whispering SandsCondo
Taxes:$3,007
Middle School: Heron Creek Middle
Remarks: Front row FULL Gulf views—just one floor above the sand! Priced below market, this lovely 2 bed/2 bath GULF FRONT tower residence in the premiere Siesta Key property of Whispering Sands represents an opportunity to move right in, and if desired, ultimately take your time to create your own vision and make it your own - and enjoy a lifetime of memories. Don’t hesitate - this is currently the best priced Gulf front tower unit in Whispering Sands. Upon entry, you’re greeted with spectacular, unobstructed 180-degree views of the shimmering aquamarine Gulf. Along with its direct FULL GULF VIEWS, this unit is just one floor away from the sparkling beachside pool and 800’ of Whispering Sands' own private beach. This unit features a nicely remodeled kitchen and great OPEN CONCEPT floor plan, enabling easy interaction between you and your guests. The kitchen includes granite countertops & backsplash, an 8’ breakfast bar, recessed LED & under cabinet lighting, convenient built-in desk, and an abundance of cabinet storage. Experience true Florida living by opening the floor to ceiling sliders in the living room and primary bedroom and take in the fresh salt breezes and the gentle sound of the surf. Both sets of sliders include remote controlled shades. The primary bedroom includes a custom walk-in closet, large vanity area, and ensuite bath with marble countertops, glassed walk-in shower, and linen closet with pullout drawers. A set of glassed French doors with privacy shades opens into the guest bedroom, which can serve as both an office and a bedroom with a fantastic SICO wall bed, desk, and built-ins. This unit is being sold As Is. Whispering Sands is a premiere 55+ Gulf front community offering 2 heated pools, Tower Lounge, Clubhouse – both of which are undergoing remodeling with a completion date in 2026 – beachside Tiki hut and grills, shuffleboard, canoe/kayak storage, and 800’ of private beach on the Gulf. In one of the best locations on Siesta Key, Whispering Sands is right around the corner from the colorful boutiques and restaurants of Siesta Key Village. Don’t miss this opportunity!
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Harriet Stopher (404-316-8944)
239 HOURGLASS WAY #V7, SARASOTA, FL 34242
$640,00045 Days on yellowkey MLS ID: A4691064
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1327 Built: 1968Monthly Fee: $1,793 Tax: $5,346 (2025)Community: Whispering SandsVilla
Taxes:$5,346
Remarks: Tucked away in a peaceful, private setting overlooking the tranquil, shimmering lagoon - with its abundant fish, birds, and aquatic life - this beautifully updated 3 Bed/2 Bath villa in the premier GULF FRONT property of Whispering Sands offers the perfect blend of comfort, style and serenity. Step inside to discover a bright NEW kitchen featuring new granite countertops, stainless appliances, recessed & under cabinet lighting and an open, inviting feel ideal for everyday living and entertaining alike. Engineered wood flooring flows throughout the home, complemented by neutral paint tones, new interior doors, and thoughtfully updated baths with granite counters, new vanities and modern fixtures. A spacious screened brick paver lanai extending the full length of the residence may well be the star of the show, creating an ideal private indoor-outdoor living space to relax and enjoy the lush tropical surroundings. A private fenced brick paver patio offers an additional retreat for entertaining, dining al fresco, or simply unwinding in the Florida sunshine. Additional upgrades include a newly painted 1-car garage with new full-sized washer and dryer and new sink. The freshly painted front door, new screen door - along with a brick paver sidewalk and driveway - enhance the home’s welcoming curb appeal. Newly painted exterior in 2025. New landscaping is planned for the complex in 2026. Whispering Sands is a 55+ Gulf front property offering 800’ of PRIVATE beach, 2 heated pools, beachside Tiki Hut and grills, shuffleboard, & canoe/kayak storage. The clubhouse is currently undergoing complete remodeling and will include fitness rooms, a full catering kitchen, large screen TV, and an elegant, comfortable space for social events. Ideally located just around the corner from the shops and restaurants of Siesta Key Village, this move-in ready property combines stylish updates, abundant outdoor living space, and a truly peaceful location to create the perfect coastal retreat!
206 HOURGLASS WAY #V10, SARASOTA, FL 34242
$640,00046 Days on yellowkey MLS ID: A4690141
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1462 Built: 1968Monthly Fee: $1,793 Tax: $5,579 (2025)Community: Whispering SandsVilla
Taxes:$5,579
Remarks: Welcome to your coastal retreat in the form of this secluded, 2 bed/2 bath freestanding villa with one car garage in the premiere GULF FRONT property of Whispering Sands. OFFERED FURNISHED. This surprisingly large, 1,462 square foot property has been UPDATED in 2025 with fresh paint, NEW crown molding & baseboards, NEW kitchen and updated baths. The exceptionally large living room allows for multiple seating groups, while a wall of floor to ceiling sliders – treated with beautiful shades - provides an abundance of natural light. Meal prep is easy in your bright NEW kitchen featuring white cabinetry, subway tile backsplash, granite counters, stainless Whirlpool appliances, recessed lighting, fandelier, & vinyl plank flooring. Three sets of new hurricane impact sliders open from the kitchen, dining room, and 2nd bedroom into your private fenced brick paver patio which offers valuable outdoor space for sunny relaxation or effortless entertaining. Both newly carpeted bedrooms feature an extended living space to accommodate a small seating group, desk, or exercise equipment. The bathrooms have been refreshed with NEW granite countertops, cabinets, vanities & fixtures. NEW 2026 stacked W/D in garage. 2019 HVAC. Recent enhancements include exterior pressure washing and villa painting in February 2026. Newly updated brick paver driveway. New landscaping is being planned by the HOA starting in 2026. Whispering Sands is a premiere 55+ Gulf front property ideally located next to the colorful boutiques and dining options of Siesta Key Village, and offers 800’ of PRIVATE beach, 2 heated pools, new beachside Tiki Hut, grills, shuffleboard, canoe/kayak storage, security, & onsite management. The clubhouse is scheduled to be remodeled in 2026 and when completed will include fitness rooms, catering kitchen, and an elegant and comfortable space for social gatherings. Seller is willing to include 3 year new Kia SUV automobile with acceptable offer. Your coastal retreat awaits!
20 WHISPERING SANDS DR #1201, SARASOTA, FL 34242
$1,195,000163 Days on yellowkey MLS ID: A4678026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1282 Built: 1973Monthly Fee: $1,398 Tax: $10,552 (2025)Community: Whispering SandsCondo
Taxes:$10,552
Remarks: A truly RARE offering, this TOP floor, GULF FRONT penthouse residence crowns the northwest CORNER of the South Tower of Whispering Sands – the premiere 55+ Gulf front enclave on the idyllic westernmost point of Siesta Key where only a fortunate few enjoy world class, panoramic views of the sparkling Gulf and 800’ of PRIVATE quartz sand beach! FULL GULF views from this unit unfurl in every direction, offering a daily masterpiece of colors that shift with the rising and setting sun. Wake up to breathtaking Gulf views that seem to stretch to infinity, offering a tranquil retreat from the ordinary. In the evening, enjoy the golden hues of Florida sunsets and starlit dinners from your expansive 28’ balcony, where the Gulf breezes and soft cries of the seagulls serve as the perfect soundtrack. This penthouse is more than just a property – it’s also a canvas for your imagination. Distinctive architectural elements and premium untapped potential invite you to curate a space that reflects your own unique style and vision. Whether you envision modern sophistication, coastal charm, or timeless elegance, the untapped possibilities of this unit invite your imagination to run free as you create the ultimate sanctuary tailored to your personal vision. Whispering Sands' relaxed, informal lifestyle provides the perfect backdrop for your next chapter. Start your day with a set of vigorous laps or water aerobics in one of two beautiful, heated pools - one beachside, one clubside. You’ll never need to leave the property to get your gym workout in the main clubhouse currently undergoing a complete remodel. Plant your feet in the cool quartz sand and enjoy daily dips in the balmy Gulf. Beach loungers are set out daily for the exclusive use of owners. Enjoy an impromptu game of beachside shuffleboard followed by a picnic supper at the Tiki Hut. Whether spending time exploring the vibrant cultural offerings of Sarasota just across the North Bridge, indulging in the local arts scene, or simply relaxing on your breezy private balcony with a good book, the options this property offers are endless. Secure your private viewing of this unique residence and claim your place in this coveted coastal community!
19 WHISPERING SANDS DR #204, SARASOTA, FL 34242
$995,000137 Days on yellowkey MLS ID: A4681694
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1282 Built: 1973Monthly Fee: $1,440 Tax: $8,669 (2025)Community: Whispering SandsCondo
Taxes:$8,669
Remarks: Embrace the rare opportunity to own a GULF FRONT residence in the coveted Siesta Key community of Whispering Sands – where breathtaking FULL GULF views, an unbeatable location, and endless potential come together. This 2 bed/2 bath 2nd floor tower unit showcases panoramic vistas of the shimmering Gulf, on 800’ of your own PRIVATE quartz sand beach, and the nightly spectacle of vibrant symphonies of colorful sunsets from your expansive 24’ open-air balcony. Offered in largely original condition, this residence is a true blank canvas—an exceptional value in today’s buyer’s market and the perfect chance to design and remodel from top to bottom in your own personal style. Create the coastal retreat you’ve always envisioned while investing in a premier Gulf front address known for its timeless appeal and strong long-term desirability. Reputable contractor names are available to help bring your vision to life. Life in the sought after 55+ community of Whispering Sands is peaceful and resort inspired. Enjoy two heated, fenced pools with new travertine decks, beach loungers for the exclusive use of owners and their guests, beachside Tiki Hut, gas grills, shuffleboard, canoe/kayak storage, and a beautifully soon to be remodeled clubhouse and Tower Lounge—the latter of which is reserved for the exclusive use of tower residents outside community events, and conveniently located on your floor. You’re also just an elevator ride down to the sparkling Gulf side pool and powder soft sand. Ideally positioned just moments from Siesta Key Village, you can leave your car behind and stroll to charming boutiques, live music, and an array of dining options. End each day with your toes in the sand or on your private balcony, savoring the tranquil rhythm of the waves and the company of friends as the sun melts into the horizon. This is more than a condo—it’s a lifestyle, a legacy of memories in the making, and a chance to secure your own piece of world class Gulf front paradise.
101 WHISPERING SANDS DR #107, SARASOTA, FL 34242
$475,000203 Days on yellowkey MLS ID: A4674069
REDUCED by $20,000 (4.0%) on 05/04/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1271 Built: 1969 Tax: $5,864 (2024)Community: Whispering SandsCondo
Taxes:$5,864
Remarks: One or more photo(s) has been virtually staged. Welcome to affordable GULF FRONT living! This is one of the best values in Whispering Sands. The seller is willing to offer a $60,000 SELLER CREDIT with an acceptable offer to offset any future improvements or assessments. This recently updated, 2 bed/2 bath, DOUBLE LANAI CORNER unit is nestled in the southwest corner of the popular Tropic View building, the Whispering Sands midrise closest to the Gulf and 800' of your own private beach! The freshly painted interior features NEW luxury vinyl plank flooring, NEW interior doors, and NEW overhead designer lighting and fans. Four sets of floor-to-ceiling sliders open from the living areas and bedrooms into TWO separate 24’ glassed and screened lanais – complete with epoxy flooring and NEW ceiling fans to capture the coastal breezes. After a full day at the beach, meal prep is easy in your partially open kitchen featuring NEW granite countertops, farmhouse style stainless sink, and NEW 2025 Whirlpool and GE stainless appliances. The spacious primary bedroom includes a nice walk-in closet and an ensuite bath, while the generous second bedroom comfortably accommodates up to two queen beds and boasts a full wall of closet space. Both updated bathrooms feature NEW cabinets, vanities, & fixtures, with glassed walk-in showers and recessed lighting. Brand NEW 2026 HVAC system and 2025 water heater. The unit also comes with its own assigned storage locker located just across the hall, ideal for storing all of your beach essentials. Conveniently located next door to the colorful shops and restaurants of Siesta Key Village, Whispering Sands is a premiere 55+ Gulf front property offering two heated pools, beachside Tiki Hut and gas grills, shuffleboard, canoe/kayak storage, and 800' of PRIVATE quartz sand beach. The clubhouse is currently undergoing complete remodeling. Upon completion in 2026, it will include a full catering kitchen, fitness rooms, large screen TV, and an elegant space for community wide or private social events. New landscaping plan for the building and throughout the entire 25-acre property is currently underway. Attractively priced below market, this unit represents a great investment. Don’t miss this opportunity to experience the ease of island living at Whispering Sands!
199 WHISPERING SANDS DR #204, SARASOTA, FL 34242
$609,000116 Days on yellowkey MLS ID: A4684412
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1271 Built: 1970Monthly Fee: $1,579 Tax: $5,538 (2025)Community: Whispering SandsCondo
Taxes:$5,538
Remarks: Welcome to effortless coastal living in this beautifully UPDATED second floor midrise residence in the premier GULF FRONT property of Whispering Sands! Designed with an OPEN CONCEPT floor plan, this light-filled condo showcases a bright, sophisticated 2023/2024 REMODELED kitchen featuring quartz countertops, stainless Samsung appliances, an impressive 8' breakfast bar with seating for 3, soft close cabinetry, and recessed lighting—all complemented by an elegant uplit tray ceiling. A true highlight is the expansive 29' x 8' lanai stretching the full length of the residence—offering an inviting extension of the living space ideal for relaxing, dining, or working from home, complete with hurricane impact sliders for total peace of mind. Both bathrooms have been tastefully updated with granite countertops and tiled, glass-enclosed walk-in showers, while ceiling fans and crown molding add comfort and sophistication throughout the unit. Beyond the residence, Whispering Sands offers true resort-style living in a premier Gulf front setting. Spend your days lounging on your private beach, taking a refreshing swim in one of two heated pools, an invigorating workout in the gym, or enjoying the vibrant social atmosphere of the clubhouse just steps from your door. Whether it’s a peaceful morning walk along the shoreline or a sunset gathering with neighbors, every day feels like a vacation. Perfectly positioned just steps from the clubhouse—currently undergoing complete remodeling in 2026—and pool, and a short stroll along the sidewalk to your 800' of your own private beach, this residence embodies the very best of resort style living. Ideally located just around the corner from the boutiques and restaurants of Siesta Key Village, you'll enjoy the perfect balance of relaxed beachfront living and easy access to dining, entertainment and island charm. Move right in and start enjoying the easy island lifestyle you’ve been dreaming of!
225 HOURGLASS WAY #202, SARASOTA, FL 34242
$510,00076 Days on yellowkey MLS ID: A4689015
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1271 Built: 1969Monthly Fee: $1,566 Tax: $5,016 (2025)Community: Whispering SandsCondo
Taxes:$5,016
Remarks: Discover elevated, light-filled coastal living in this beautifully updated 2nd floor residence in the premiere Gulf front property of Whispering Sands! Offered completely TURNKEY FURNISHED. The wonderful OPEN CONCEPT layout flows seamlessly from the kitchen, living and dining spaces into your own private, 34’ south facing lanai—perfect for enjoying sunny mornings, gentle breezes, and relaxed indoor-outdoor living year round. As a bonus, this is a highly desirable end unit, with a wonderful extra window in the living space that invites in abundant natural light, enhancing the open, airy feel throughout. Designed for both style and function, the beautifully REMODELED, kitchen features sleek stone countertops, soothing neutral tile backsplash, an 8’ breakfast bar with seating for 4, stainless Frigidaire and Samsung appliances, soft close cabinetry, and wonderful overhead recessed lighting. Both bathrooms have been tastefully updated with stone counters, while the primary suite offers a private ensuite bath and a walk-in closet for comfortable everyday living. Equally spacious, the guest bedroom is large enough to accommodate two queen beds. Nestled on the westernmost point of Siesta Key, Whispering Sands is a highly desirable 55+ Gulf front community offering resort style living – all ideally just moments away from the colorful boutiques, dining options, and charm of world famous Siesta Key Village. The complex offers 800’ of PRIVATE quartz sand beach on the sparkling Gulf, 2 heated pools, new beachside grills and Tiki Hut, shuffleboard, and canoe/kayak storage, The main clubhouse – just steps from this unit - is currently undergoing complete remodeling and upon completion will include fitness rooms, a full catering kitchen, large screen TV, and an elegant, comfortable space for social events or private entertaining. Effortless island living starts here. Don’t miss this opportunity to own this move-in ready, coastal escape in an exceptional island setting!
5507 CONTENTO DR, SARASOTA, FL 34242
$1,725,000124 Days on yellowkey MLS ID: A4683288
REDUCED by $50,000 (2.8%) on 06/22/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1788 Built: 1969 Tax: $15,484 (2025)Community: Siesta IslesSpa: NoSingle Family
Taxes:$15,484
Middle School: Sarasota Middle
Remarks: A BOATER'S DREAM! Welcome to your Siesta Key waterfront dream home on a third of an acre lot! Private dock with a 7,000lb boat lift on a wide part of the Grand Canal! Move right in and start enjoying the island lifestyle! This home features great water view on the widest part of the canal! Brand new landscaping and freshly painted exterior. Sold furnished with a few exceptions. The heated pool and panoramic pool cage create a serene setting. Mostly Hurricane rated windows, new dishwasher and refrigerator, wine refrigerator, custom wood cabinets, granite counters and breakfast bar. Tile floors and engineered wood, built-out closets, open floor plan, 2 car garage, circular driveway, outdoor shower. 3 bedrooms and 3 full bathrooms plus laundry room. A few blocks from world famous SIESTA BEACH, short drive to downtown Sarasota, St Armand's, Lido and much more. ***THIS HOME HAS NOT HAD ANY STORM DAMAGE AND NO FLOODING.****BASE ELEVATION 10 Ft***SELLER MOTIVATED***
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Livya Hament (941-735-1227)
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