Location: Sarasota , 34242
Do Not Show Listings
329 BEACH RD #A, SARASOTA, FL 34242
$3,895,00011 Days on yellowkey MLS ID: A4688489
Bed: 5 Bath: 6.0 Liv Area Sq Ft: 4563 Built: 2020 Tax: $31,490 (2024)Community: 329 Beach Land CondominiumSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$31,490
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: Spirited, curated, and elevated, The Rooftop feels less like a single residence and more like a composition of places — where natural materials, global textures, and deep coastal tones come together in a way that is both grounded and transportive. Rich woods, sculptural elements, and layered finishes create a sense of depth throughout, while a sleek, modern kitchen introduces contrast with clean lines and contemporary precision. Positioned to capture stunning Gulf views from every vantage point, the home unfolds across nearly 4,000 square feet of thoughtfully designed living space. Six en-suite bedrooms, including custom bunk accommodations, provide flexibility for hosting, while the main living level is anchored by an expansive great room that opens to a balcony overlooking the water. Here, indoor and outdoor living merge seamlessly, framed by sunset skies and kissed by the coastal breeze. At the top, the residence reveals its defining feature. A 500-square-foot rooftop deck offers unobstructed Gulf views, with bar seating, lounge areas, and a setting designed for sunrise, sunset and every moment in between. Adjacent, an air-conditioned club room extends the experience with additional space for gathering, gaming, and relaxation, creating a seamless connection between interior comfort and open-air living. Below, the outdoor environment is equally immersive. A heated saltwater pool with integrated volleyball and waterslide, an oversized spa that doubles as a swim-up bar, and a covered patio with dining, lounge seating, and entertainment spaces create a private setting designed for both energy and ease. The entire space is framed by lush landscaping, enhanced with coastal style, and enclosed for privacy, reinforcing the home’s sense of retreat. Layered, expressive, and distinctly its own, The Rooftop is a residence that invites both escape and arrival. Designed for the discerning collector, this residence pairs sophisticated, storm-ready durability with an expansive layout optimized for both private family legacy and the high-capacity demands of elite coastal vacationing. More than a home, The Rooftop is part of an exclusive Vunique collection with a proven history of strong rental performance — each residence one-of-one, purpose-built to balance bold design and bespoke experience. Here, ownership transcends address; it becomes a mark of belonging to something beautifully uncommon.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Rudy Dudon (941-234-3991)
1280 DOLPHIN BAY WAY #503, SARASOTA, FL 34242
$1,589,00027 Days on yellowkey MLS ID: A4687031
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 2217 Built: 1998Monthly Fee: $1,985 Tax: $13,269 (2025)Community: Dolphin Bay-Siesta Key Sec ACondo
Taxes:$13,269
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: Experience endless panoramic views of downtown Sarasota and Sarasota Bay from the climate-controlled balcony of this newly renovated top-floor residence in the gated community of Dolphin Bay on Siesta Key. This spacious condo offers over 2,200 square feet of beautifully updated living space, featuring 2 bedrooms, 2 bathrooms, and a den, all enhanced by vaulted ceilings that create an open and airy coastal atmosphere. Enjoy stunning sunsets over Siesta Key Beach from the front entryway each evening, and wake to beautiful sunrises from the primary bedroom and lanai—an exceptional feature of this remarkable home. Residents of Dolphin Bay enjoy a true waterfront lifestyle with access to a private community dock, clubhouse, tennis courts, fitness center, and a resort-style pool. A private one-car garage, with epoxy flake floors, is conveniently located just steps from the elevator. Perfectly situated within minutes of the beach, shops, and restaurants, this residence combines luxury, convenience, and the best of Siesta Key living. Enjoy the waterfront lifestyle at its finest in this exceptional move-in-ready home. Contact me for a private showing today.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Maryana Zilinskiy (941-744-6065)
5600 BEACH WAY DR #315, SARASOTA, FL 34242
$780,000311 Days on yellowkey MLS ID: A4655560
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1259 Built: 1970 Tax: $7,099 (2024)Community: Beachway AptsCondo
Taxes:$7,099
Remarks: Are you ready to create your lifestyle in the sun, steps away from the quartz crystal white powdery sands and warm Gulf waters of the award-winning Siesta Key Beach? This wonderfully located turn-key, furnished condo end unit is oh so unique on the top floor with views of the beautiful beach and Gulf waters, a rare, remodeled find on the spectacular Gulf coasts of Florida! The rental income is excellent! This recently, completely remodeled from ceiling to floor, wall to wall, unit has 2 bedrooms, 2 bathrooms, hard flooring throughout, a sprawling island, quartz countertops, impact windows and sliders, AND has a spacious balcony, ready for you to relax and enjoy. This unit transfers with $50,000 in furnishings and furniture. This is a perfect place for you to have your dream of a beach life come to reality, with the potential of using it to generate income with monthly rentals. This amazing mid-rise condominium community offers a heated community pool, outside grills, a clubroom with a kitchen, plenty of guest parking and a laundry room on each floor. Recent improvements include newer roofs 2020, a newer elevator 2019, re-plumbed stacks 2018, refreshed landscaping 2020, and new vinyl fencing 2021. The quarterly fee includes access to the heated community pool, basic cable, water/sewer, pest control, weekend on-site maintenance person, and community insurance. Enjoy convenient access to Siesta Key Beach and to Siesta Key Village shops and restaurants with the free trolley service that stops right in front of the Beach Way community, or, walk, orrrrr take a bike cruise to many nearby shops and restaurants… You are not only buying a beach property, you are buying a lifestyle in the beautiful Southwest Florida Sun. This unit can be your own sanctuary escape and your retirement investment... Come see, come sigh and make this Siesta Key lifestyle in the Sun your own.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Karie Backman (941-404-8389)
225 HOURGLASS WAY #106, SARASOTA, FL 34242
$575,00057 Days on yellowkey MLS ID: A4683200
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1271 Built: 1969Monthly Fee: $1,566 Tax: $3,860 (2025)Community: Whispering SandsCondo
Taxes:$3,860
Remarks: Step into your own island retreat with this rare ground floor END unit in the highly sought after GULF FRONT property of Whispering Sands! Perfectly positioned with a full length screened & glassed lanai overlooking the picturesque lagoon and lush tropical landscaping, this residence captures a peaceful, serene setting with a touch of everyday luxury. Thoughtfully updated and designed for effortless living, the OPEN CONCEPT floor plan features non-slip porcelain tile placed on the diagonal, a skip trowel ceiling, and a spacious light-filled living space with sunny west facing window. The nicely RENOVATED kitchen is a standout, offering granite countertops, colorful tile backsplash, a 9’ x 4’ breakfast bar, white soft-close cabinetry, and a suite of GE, Whirlpool, Frigidaire, and LG appliances, all enhanced by overhead recessed LED lighting with dimmer. The cabinetry and granite extend into the entire length of the dining area, creating additional storage and an elegant serving space ideal for entertaining. The original interior living room sliders have been removed to seamlessly incorporate the lanai, transforming it into a sun-drenched sunroom that expands your cooled living space and invites the outdoors in. Just outside, a small brick paver patio off the sunroom offers the perfect spot for grilling, sunning, or unwinding after a day at the beach. Both bathrooms in this unit have been tastefully updated with NEW vanities, fixtures, and cabinetry. Additional highlights include a complete set of 2016 hurricane impact sunroom sliders and 2025 water heater. At Whispering Sands, every day feels like a vacation—with 800’ of PRIVATE beach, two heated pools with new travertine tile decks, clubhouse – currently undergoing a complete remodel which will include a catering kitchen and fitness rooms – beachside Tiki Hut, grills, and canoe/kayak—all just a short stroll to the vibrant shops and dining options of Siesta Key Village. Your island getaway awaits!
Listing Agent: Harriet Stopher (404-316-8944)
7233 PINE NEEDLE RD, SARASOTA, FL 34242
$4,300,00016 Days on yellowkey MLS ID: A4688394
Bed: 3 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4294 Built: 1950Monthly Fee: $450 Tax: $9,991 (2025)Community: Siesta Properties IncSpa: YesSingle Family
Taxes:$9,991
Remarks: Pre-Construction. To be built. A rare and compelling opportunity to create a custom coastal estate within the prestigious Sanderling Club on Siesta Key, one of the island’s most private and sought-after enclaves. Set on an expansive .70-acre homesite, this future residence will feature a thoughtfully designed footprint spanning 4,294 square feet under air and over 6,400 total square feet, offering a refined blend of scale, comfort, and architectural presence. Positioned to capture desirable southern exposure, the property enjoys a serene natural backdrop, creating a setting rich in privacy, wildlife, and unobstructed beauty. The home will be delivered with the structural framework and layout in place, while allowing the future owner to curate finishes, materials, and design details to their exact vision, resulting in a truly personalized luxury residence. The Sanderling Club is renowned for its understated elegance and unmatched seclusion, offering 24-hour guard-gated security and a lifestyle centered around privacy and connection to nature. Residents enjoy access to tennis and pickleball courts, a private marina, and a historic beachfront clubhouse with exclusive access to the powdery white sands of Siesta Key Beach. Quiet, secure, and distinctly refined, this is an extraordinary chance to bring your vision to life within one of Sarasota’s most coveted coastal communities—where luxury is defined not only by design, but by space, serenity, and discretion.
925 BEACH RD #107, SARASOTA, FL 34242
$629,00021 Days on yellowkey MLS ID: A4687498
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 940 Built: 1972 Tax: $3,927 (2025)Community: La SiestaCondo
Taxes:$3,927
Remarks: Located directly across the street from world-famous Siesta Key Beach—recently ranked the #1 Beach in the United States and among the top beaches in the world— this residence offers exceptional convenience and effortless access to the sand. Simply walk to the beach in approximately five minutes—no driving, no searching for parking, just easy coastal living. Enjoy morning walks and evening sunsets on Siesta Key Beach just steps away. This 2-bedroom, 2 full bath residence offers approximately 940 square feet of comfortable living space with an open layout designed for relaxed island living. The updated kitchen features wood cabinetry, granite countertops, and stainless steel appliances, flowing seamlessly into the dining and living areas. Tile flooring throughout provides durability and easy maintenance, while the split-bedroom floor plan allows for privacy between residents and guests. One of the largest 2-bedroom, 2 full bath floor plans in the community, competitively priced at $629,000. Weekly rentals are permitted, offering outstanding flexibility for both personal use and income potential. Onsite property management is available, making guest coordination and rental operations easy and convenient. Covered parking is included, along with ample guest parking. La Siesta residents enjoy access to a heated pool, fitness room, clubhouse, and beautifully maintained grounds. Located just minutes from Siesta Key Village’s restaurants, shopping, and entertainment, this property offers the ideal balance of relaxation and accessibility. Whether you’re searching for a personal beach retreat, seasonal residence, or an income-producing investment, this location delivers the lifestyle buyers and vacationers come to Siesta Key to enjoy.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Lisa Garcia (941-266-9060)
6962 BELGRAVE DR, SARASOTA, FL 34242
$1,950,000167 Days on yellowkey MLS ID: A4670404
REDUCED by $199,000 (9.3%) on 04/06/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2224 Built: 1974Monthly Fee: $83 Tax: $16,001 (2024)Community: Princes GateSingle Family
Taxes:$16,001
Remarks: FABULOUS Siesta Key property on protected canal with direct Intracoastal and Little Sarasota Bay access. The star of this property is the protected canal with cement seawall and dock just 5 homes from the Intracoastal Waterway. Easy Gulf access via newly opened Midnight Pass allows expanded boating options. The 0.39 acre lot has plenty of room to expand the current home if desired. The location can’t be beat: less than 1 mile to the Stickney Point Bridge. 0.4 miles to Siesta Key Beach Access #13. Only 4 blocks to dining, shopping and entertainment. This home is on a quiet, private cul-de-sac. Move right in, expand, or build your dream home. The fenced yard is perfect for family and pets. A new metal Roof was added in 2025 and a new AC in May 2024. The 2020/2021 remodel extended and updated the kitchen, enclosed the rear lanai, relocated the front door to add an interior foyer, and upgrade most windows and sliders. The kitchen expansion includes new cabinets and an oversized breakfast bar. This split-plan home has a large primary bedroom with French doors opening to the pool. On the other side of the home find a guest bedroom, updated full pool bath, and secondary suite with a half bath (with plenty of room to create a full bath) that also opens to the pool. The current office can be utilized as a 4th bedroom with closet and ramp directly to the garage. With a separate living room and family room, there is plenty of space for everyone to spread out. Outside, find a large pool area overlooking the canal and a large, circular driveway that has beautiful pavers and two large side yards. This home experienced NO flooding during the 2024 storm season. Come see all the opportunities this property has to offer.
Listing Agent: Suki Scollo (941-587-2289)
226 OGDEN ST, SARASOTA, FL 34242
$1,000,000189 Days on yellowkey MLS ID: A4668141
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1559 Built: 1974 Tax: $12,834 (2025)Community: Siesta Rev OfSpa: NoSingle Family
Taxes:$12,834
Remarks: Tucked away on the quiet, residential north side of Siesta Key, this once-charming 2-bedroom pool home is ready for its next chapter. The property was impacted by last summer’s hurricanes, but the good news is: the metal roof held strong and didn’t leak. With solid bones, a private pool, and a cute backyard that still hints at the home’s former charm, this is a golden opportunity for someone with vision to bring it back to life. The location alone makes this one special, just minutes to the beach, village shops, and dining, yet surrounded by peaceful island neighborhoods. Whether you’re looking to restore it as your island getaway, rebuild for modern coastal living, or invest in a premium piece of Siesta Key real estate, this property is full of potential and promise. Come see what’s possible in one of the most desirable corners of Sarasota’s barrier islands.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Beth Helvey Pa (941-330-3600)
4185 ROBERTS POINT LOT 18 CIR, SARASOTA, FL 34242
$3,400,000174 Days on yellowkey MLS ID: A4669711
Bed: 5 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 3200 Built: 2027 Tax: $11,511 (2024)Community: Roberts Point 2Spa: YesSingle Family
Taxes:$11,511
Remarks: Pre-Construction. To be built. Joint-Venture opportunity partnering with investors up and down Florida's coast. Brought to you by Noah Thomas Builders — where modern luxury meets timeless coastal elegance. A masterclass in luxury homebuilding, this Noah Thomas Builders contemporary coastal home offers an exceptional blend of modern aesthetics and is built to FEMA's latest standards. Step inside this 3240 sqft home offering four bedrooms, four bathrooms, an open-concept floor plan with high ceilings and premium finishes throughout. It features all hurricane-rated windows and doors and is constructed to be as hurricane and flood-proof as possible-giving you peace of mind while living steps from the water. The kitchen boasts quartz countertops, top-tier appliances, and a spacious island perfect for entertaining. Retreat to the luxurious master suite with spa-inspired bath and expansive walk-in closets. Endless sunshine, gentle breezes, and your own private pool and spa — relax, unwind, and entertain in your personal outdoor oasis. Additional highlights include a private elevator, gas generator and wine room. The rooftop deck, however, defines this residence. This elevated sanctuary invites you to experience Siesta Key from a completely new perspective. Your private escape above it all — a space built for sunsets, sea breezes, and unforgettable gatherings. Situated on the quiet north end of Siesta Key, Roberts Point is prized for its natural beauty, privacy, and proximity to Siesta Beach, Siesta Village, and downtown Sarasota. All images, renderings, and descriptions illustrate the intended design and style by Noah Thomas Builders. Finishes, materials, and specifications may change during the build process. Pricing, availability, and final details subject to adjustment prior to completion.
Listing is courtesy of: 1ST CLASS REAL ESTATE SUNCOAST (386-882-6644)
Listing Agent: Holly Wikfors, Llc (239-777-8075)
9397 MIDNIGHT PASS RD #901, SARASOTA, FL 34242
$896,50050 Days on yellowkey MLS ID: A4683506
0 Days Off yellowkey (back on 4/6/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1630 Built: 1975Monthly Fee: $1,433 Tax: $7,721 (2025)Community: Pointe On Midnight PassSpa: YesCondo
Taxes:$7,721
Middle School: Booker Middle
Remarks: Under contract-accepting backup offers. Absolutely stunning, furnished, and truly one-of-a-kind THREE-BEDROOM residence at The Pointe at Midnight Pass — the only 3-bedroom currently available in this highly sought-after community. Positioned on the 9th floor at the southern tip of Siesta Key, this impeccably renovated corner unit sits at a rare coastal convergence where the Gulf, Little Sarasota Bay, and Blind Pass Lagoon meet. Enjoy panoramic sunrise views across the Intracoastal waters, glowing Gulf sunsets, and protected preserve vistas — all from one extraordinary setting. High-end finishes define the interior, including solid wood cabinetry, granite countertops, stainless appliances, and thoughtfully curated details throughout. The spacious primary suite features a beautifully updated en-suite bath with a jetted shower and a custom walk-in closet designed for optimal storage. Two additional bedrooms function seamlessly as guest suites, office, or den. The Gulf side bedroom is equipped with a custom Murphy bed and built-ins, offering flexibility without sacrificing style. The second bath features a Jacuzzi tub for relaxed coastal living. The expansive, air-conditioned lanai invites year-round enjoyment, offering a serene vantage point overlooking the Jim Neville Preserve and surrounding waterways. A pass-through utility room with washer, dryer, laundry sink, and folding counter adds everyday practicality. New hurricane-impact windows and sliding glass doors, along with an energy-efficient HVAC system, provide comfort and peace of mind. A rare double parking space under the building further distinguishes this offering. The Pointe is a gated, pet-friendly, five-acre waterfront community featuring boat and kayak docks, resort-style pool, tennis and pickleball courts, fitness center, saunas, clubhouse amenities, and a private island gazebo. More than a condominium, this is a private waterfront retreat positioned in one of Siesta Key’s most iconic locations.
Listing is courtesy of: CAPITAL REAL ESTATE ENTERPRISE (941-921-1000)
Listing Agent: Andrea Eck (941-704-7222)
9397 MIDNIGHT PASS RD #905, SARASOTA, FL 34242
$749,000180 Days on yellowkey MLS ID: A4669008
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1348 Built: 1975 Tax: $5,944 (2025)Community: Pointe On Midnight PassCondo
Taxes:$5,944
Remarks: Welcome to 9397 Midnight Pass Rd #905 Sarasota, FL 34242 at The Pointe on Siesta Key, a fully renovated 1,348 SF, 2-bedroom, 2-bathroom luxury condo offering breathtaking Little Sarasota Bay and Intracoastal waterway views from the 9th floor. This stunning residence underwent a complete custom renovation in 2023, setting it apart from every other unit in the building. The open-concept kitchen features quartz countertops, vaulted ceilings with a bold rock-and-metal aesthetic, and a one-of-a-kind handcrafted glass-art backsplash, with bar seating connecting seamlessly to the dining and living areas, a custom layout rarely found at The Pointe. Luxury vinyl plank flooring flows throughout every room including the lanai, while wood acoustical paneling enriches both the living space and primary suite. Additional upgrades include HD-mounted televisions, a 2023 AC system, and a new LG washer and dryer, making this unit nearly turnkey and move-in ready. Step onto your private lanai, protected by hurricane-grade sliders, and take in tranquil water views of Little Sarasota Bay, where dolphins, manatees, and sailboats pass through calm Intracoastal waters daily. As a resident of The Pointe's gated five-acre community, enjoy resort-style amenities including boat docks, kayak and canoe access, a heated pool and spa, sauna, tennis and pickleball courts, BBQ gazebos, a clubhouse, and a fitness center with panoramic Intracoastal views. Located just minutes from Turtle Beach, Siesta Key Village, waterfront dining, local marinas, and coastal cafés, this property is ideal whether you're seeking a luxury Siesta Key waterfront residence, a vacation condo, or a Sarasota investment property. Negotiable furnishings available. Schedule your private showing today.
Listing is courtesy of: HARRY ROBBINS ASSOC INC (941-924-8346)
Listing Agent: Emerson Robbins (941-404-0382)
116 GARDEN LN, SARASOTA, FL 34242
$2,150,000161 Days on yellowkey MLS ID: A4671064
Bed: 4 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 2971 Built: 2017 Tax: $20,113 (2024)Community: Siesta Rev OfSingle Family
Taxes:$20,113
Remarks: Effortless Island Living on Siesta Key’s Coveted North End. Discover the perfect blend of modern luxury and low-maintenance living in this contemporary coastal retreat, ideally located on the quiet North End of Siesta Key. Enjoy deeded beach access, mesmerizing Gulf and Big Pass views, and effortless proximity to Siesta Village, the North Bridge, and downtown Sarasota. Built in 2017 to the highest standards by MGB—My Green Building—this four-level residence was designed for comfort, efficiency, and peace of mind. Solid construction, energy-smart design, impact-rated materials, and a brand new A/C system (March 2026) make it the ideal lock-and-leave home for those seeking a worry-free coastal lifestyle. Light-filled living spaces flow seamlessly between the gourmet kitchen, dining, and family areas, all centered on the third floor for optimal views and connection. The private primary suite spans the top level with its own balcony retreat, while three guest bedrooms on the second floor offer space for family or friends. An elevator connects all four floors for easy access, and the flexible lower level provides extra room for a fitness area, studio, or media lounge. Designed for those who value quality, comfort, and ease, this home offers all the benefits of coastal living—without the upkeep. From morning beach walks to sunset cocktails overlooking the Gulf, every day here feels like a vacation.
Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: Gerard Healy (941-961-2240)
765 SIESTA KEY CIR, SARASOTA, FL 34242
$3,799,00013 Days on yellowkey MLS ID: A4688871
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3446 Built: 1972Monthly Fee: $83 Tax: $20,136 (2025)Community: Siestas BaysideSingle Family
Taxes:$20,136
Middle School: Sarasota Middle
Remarks: Welcome to Your Slice of Paradise. A Boater’s Dream on Siesta Key Rare waterfront compound on nearly 1 acre in the heart of Siesta Key. This 5-bedroom estate features 100+ feet of deep-water frontage, your own private beach, and a private dock with direct access to the Intracoastal and Gulf—a true boater’s dream. Privately set behind a 250-ft circular driveway, the property offers a heated pool, basketball court, and expansive outdoor space rarely found on the island. Inside, enjoy two master suites (one upstairs and one downstairs), bonus rooms for an office or gym, marble flooring, designer finishes, and a chef’s kitchen with GE Café appliances. Built for comfort and efficiency with full spray foam insulation, plus 3 newer HVAC systems and a recently updated pool heater. A true slice of paradise offering space, privacy, and the ultimate waterfront lifestyle.
Listing is courtesy of: FLATFEE.COM (954-965-3990)
Listing Agent: Cliff Glansen
3941 HAMILTON CLUB CIR #9, SARASOTA, FL 34242
$2,290,00035 Days on yellowkey MLS ID: A4685652
REDUCED by $100,000 (4.2%) on 04/02/2026
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2856 Built: 1989Monthly Fee: $1,400 Tax: $15,416 (2025)Community: Hamilton ClubSingle Family
Taxes:$15,416
Remarks: PRICE IMPROVEMENT... Located in the highly sought-after Hamilton Club community on Siesta Key, this beautifully updated 3-bedroom, 3.5-bath residence offers the ideal blend of coastal comfort, boating convenience, and island living. A large screened-in porch overlooking the water provides a peaceful setting to enjoy morning coffee and gentle coastal breezes. Designed for both everyday living and entertaining, the home features a new private elevator, impact windows and doors, and your own private 10,000-lb boat lift with quick access to the water, making it easy to enjoy boating and the surrounding waterways. Each well-appointed bedroom offers its own private en-suite bathroom, providing exceptional privacy for family and guests. The residence has been thoughtfully upgraded with kitchen updates completed in 2023, updated lighting throughout (2023), fully renovated bathrooms (2022–2023), and new wood flooring, creating a fresh, modern aesthetic with timeless coastal appeal. Additional improvements include a new water softener and water pressure pump installed in 2025, enhancing everyday comfort and functionality. The home is offered furnished or unfurnished, allowing buyers the flexibility to move right in or personalize the space to their style. Hamilton Club residents will also enjoy new community landscaping scheduled for this summer, with exterior building painting planned for 2027, both covered within HOA dues for added peace of mind. Ideally located just minutes from Siesta Key’s world-famous beaches, dining, and shopping, this residence offers an exceptional combination of water views, private boating access, modern upgrades, and relaxed island living.
Listing Agent: Jennifer Thompson, Pa (941-928-0790)
4839 GIVENS CT, SARASOTA, FL 34242
$2,750,00046 Days on yellowkey MLS ID: A4683309
Bed: 5 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 3524 Built: 1994 Tax: $25,564 (2025)Community: Siesta HammockSingle Family
Taxes:$25,564
Remarks: **Rare Siesta Key Estate Compound | 4 Lots | Guest House + Studio | Minutes to Beach & Village** A truly exceptional offering on Siesta Key—this private multi-residence estate spans four combined lots, creating a rare sense of space, flexibility, and opportunity just moments from the world-renowned Siesta Beach and vibrant Siesta Key Village. The main residence features 3 bedrooms and 3.5 baths, thoughtfully designed for comfortable coastal living and effortless entertaining. Complementing the main home, a detached guest house and separate studio apartment provide additional private accommodations—ideal for extended family, visitors, or flexible use as a home office, creative space, or potential income-producing opportunity. Set within a quiet residential enclave, the expansive property offers a level of privacy seldom found on the island. Mature landscaping and generous grounds create a true “compound” feel—perfect for multi-generational living, seasonal retreats, or those seeking room to expand and customize. Whether envisioned as a private coastal retreat, a legacy family property, or a redevelopment opportunity, the possibilities here are unmatched. The oversized parcel presents potential for future expansion or reconfiguration, making this a compelling option for both end-users and investors alike. Located less than a mile from Siesta Key’s powdery soft sand beaches and the dining, shopping, and entertainment of the Village, this property delivers the best of island living—space, privacy, and proximity. **Opportunities like this are exceptionally rare on Siesta Key.**
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Caroline Amory (941-524-0463)
5507 CONTENTO DR, SARASOTA, FL 34242
$1,775,00056 Days on yellowkey MLS ID: A4683288
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1788 Built: 1969 Tax: $15,484 (2025)Community: Siesta IslesSingle Family
Taxes:$15,484
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)
144 GARDEN LN, SARASOTA, FL 34242
$875,00018 Days on yellowkey MLS ID: A4687753
Bed: 4 Bath: 2.5 Liv Area Sq Ft: 1702 Built: 1956 Tax: $11,003 (2025)Community: Siesta Rev OfSingle Family
Taxes:$11,003
Remarks: Exceptional opportunity on the highly sought-after North end of Siesta Key, just steps from Shell Beach. This property offers a prime location less than a block to the Gulf, with convenient access on and off the island via the North bridge. Located only 3 miles to Siesta Key’s world-renowned Main Beach, and under 15 minutes to the vibrant dining, shopping, and cultural scene of downtown Sarasota. The existing structure sustained significant hurricane damage and has been remediated, presenting a unique opportunity for a full renovation or redevelopment. Due to current FEMA guidelines and the 50% rule, the property is best suited for a comprehensive remodel bringing the home up to current code, or as a teardown to maximize the full potential of the lot. Zoned RSF2 with weekly rentals permitted, this property is ideal for those looking to create a luxury coastal retreat, a high-performing income-producing vacation rental, or both. The unbeatable location places you in the heart of Siesta Key’s laid-back yet vibrant beach lifestyle, surrounded by world-class beaches, boating, dining, and entertainment. Whether you envision building your dream home or capitalizing on strong rental demand, this is a rare chance to secure a premier lot in one of Sarasota’s most desirable coastal neighborhoods.
Listing Agent: Shane O'Neill (949-230-2616)
5201 AVENIDA DEL MARE, SARASOTA, FL 34242
$1,495,00072 Days on yellowkey MLS ID: A4680975
REDUCED by $65,000 (4.2%) on 04/01/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2802 Built: 2008 Tax: $6,145 (2025)Community: Sarasota BeachSingle Family
Taxes:$6,145
Remarks: WELCOME to one of Siesta Key's hidden gems. From this Key West style home, you can walk or bike ride to the soft, quartz sands of Siesta Beach or the quaint Siesta Village in minutes. This exceptional home offers high end finishes throughout. The native yard features beach sunflowers and other native plants and shrubs. The front door entrance invites you into the main level with an easy flow between the living room and the dining room. The gourmet kitchen features wood cabinets, granite countertops, stainless steel appliances and French Door refrigerator. The guest bath, laundry room and bonus room complete the downstairs. The backyard is a fenced, private oasis with a pool surrounded by stone pavers with room for lounge chairs, grill and an outdoor table setting. Mature royal palm trees and smaller palms create a beautiful habitat for birds and other wildlife. The second floor has two comfortable bedrooms, one with a private balcony. A full bath completes this level. The top level offers a spacious Primary Bedroom and En Suite Bathroom retreat with exceptional amenities, a large bathroom with granite countertops, wrap-around walk-in shower, and separate garden tub, with a screened-in balcony overlooking the pool area. The top level is completed by an additional Bedroom with an en suite Bathroom with walk-in shower, linen closet, and granite countertops. Additional features include solar panels (paid in full), a security system, stone paved driveway and walkway, along with an oversized 2 car garage. This open, sunny home is located in a quiet neighborhood at the end of the street and has so many quality features. It is definitely worth a visit.
Listing Agent: Mary Kassen (941-900-9776)
8701 MIDNIGHT PASS RD #106A, SARASOTA, FL 34242
$595,000183 Days on yellowkey MLS ID: A4668247
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1357 Built: 1980 Tax: $7,433 (2024)Community: Turtle Bay Sec 2Condo
Taxes:$7,433
Remarks: PRICE ADJUSTMENT!! Motivated sellers, seller financing will be considered! Turtle Bay community has a 3-month minimum rental policy. Experience the best of Siesta Key in this beautifully unfurnished 2BR/2BA condo in the highly desirable Turtle Bay community. Enjoy breathtaking views of Little Sarasota Bay from the enclosed, screened lanai, ideal for relaxing mornings or evening breezes. The remodeled kitchen features stainless steel appliances, updated quartz countertops, and a breakfast bar that opens into the spacious, open-concept living and dining area, perfect for entertaining. The primary suite offers an updated en-suite bathroom, walk-in closet, and built-in vanity. The generously sized second bedroom is perfect for guests or a home office. Additional conveniences include an in-unit laundry room. Recent updates include a 2023 2.5-ton Trane HVAC unit, renovated bathrooms, LED recessed lighting, and popcorn ceiling removed. A rare 12x22 detached end-unit garage provides excellent storage for your vehicle, bikes, or beach and boating gear. Turtle Bay offers resort-style amenities, including a heated pool, hot tub, clubhouse, onsite management, tennis and pickleball courts, lush landscaping, newly updated fishing pier, and boat docks - boat slips are available for nominal fee on a first-come, first-served basis. Milestone Inspection has been completed for the new owner's piece of mind. Enjoy easy access to the sparkling Gulf of Mexico waters with deeded beach access just across the street via the Tortuga Community. Conveniently close to Siesta Key Village and Siesta Key Public Beach via the free trolley stop just steps away. Coastal living at its finest! Schedule your showing today!
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Justin Piccillo (908-670-3209)
9011 MIDNIGHT PASS RD #329, SARASOTA, FL 34242
$549,000541 Days on yellowkey MLS ID: C7499000
1 Days Off yellowkey (back on 4/4/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1093 Built: 1974Monthly Fee: $999 Tax: $3,805 (2023)Community: Sunrise Cove Sec 4Condo
Taxes:$3,805
Tax Year: 2023
Remarks: Enjoy the Siesta Key lifestyle in this beautiful 2 bedroom 2 bath condo located on the 3rd floor at Sunrise Cove Siesta Key FL. Stunning views of the back bay and located across the street from Turtle Beach and Park. This public Park & Beach area features separate motorboat, kayak & canoe launches, as well as a playground, and a local trolly stop. This updated condo is being sold totally turnkey. It is ready for new owners to move in and enjoy!! Sunrise Cove residents have access to two community pools, fitness center, bayside BBQ grills and picnic tables overlooking the bay, kayak and bike storage racks, tennis and pickleball courts. There are boat slips to rent w/water & power hook-ups, a new seawall, newer roofing installed on all 4 buildings in 2018. There is a full-time onsite facility manager and maintenance manager available. Both Turtles Pub & Café and Turtles Restaurant are right next door, as well as a marina for all your boating needs. Just south of Sunrise Cove is the gourmet waterfront restaurant Ophelia’s on The Bay, which is consistently ranked as Sarasota's #1 most romantic dining destination. Siesta Key Ranked the #2 Beach in the U.S. and #9 Best Beach in the World in 2024 by TripAdvisor’s Traveler’s Choice Awards Come enjoy the quartz-crystal powdery sand and experience the soft waves and the abundance of sun & fun at gorgeous Siesta Beach!! Let us navigate you home to this amazing find in Siesta Key!!
Listing is courtesy of: PREMIERE PLUS REALTY COMPANY (239-732-7837)
Listing Agent: Dean Chesnut (941-626-2784)
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