Location: Sarasota , 34242
Do Not Show Listings
336 AVENIDA DE MAYO, SARASOTA, FL 34242
$5,395,00078 Days on yellowkey MLS ID: A4687301
REDUCED by $200,000 (3.6%) on 05/18/2026
Bed: 8 Bath: 8.5 Gar: 2 Liv Area Sq Ft: 3811 Built: 2019 Tax: $25,684 (2024)Community: Sarasota BeachSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$25,684
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Tax Year: 2024
Middle School: Brookside Middle
Remarks: Experience refined seaside luxury in this extraordinary 8-bedroom, 8.5-bathroom residence just moments from Siesta Key Beach and Siesta Key Village. Currently operating as a successful vacation rental property, this home is thoughtfully designed to maximize both guest experience and income potential. Its expansive layout, high-end finishes, and prime location make it highly desirable for short-term rentals, with ample space to comfortably host large groups. Spanning four levels and serviced by a private elevator, the home is purpose-built for hosting. The layout includes two bedrooms on the second level, five well-appointed guest suites on the third floor—many with private baths and balconies—and a top-floor bedroom offering additional privacy. Two bunk-style rooms with a shared Jack-and-Jill bath further enhance its ability to accommodate larger parties. The primary suite provides a luxurious retreat with its own balcony and spa-inspired bathroom. The open-concept main living area serves as the heart of the home, featuring a designer kitchen with premium appliances, a large gathering island, and a dedicated bar area—ideal for entertaining. Multiple dining areas, both inside and out, create flexibility for group stays, while an upper-level flex room adds value as a game room, media space, or additional lounge area. Outdoors, guests can enjoy a private resort-style setting complete with a heated pool, sun shelf, built-in spa, and covered patio designed for comfort and entertainment. Multiple balconies and a rooftop deck offer additional gathering spaces, with sweeping Gulf views and unforgettable sunsets that consistently maximize the Florida experience. With its proven rental appeal, generous accommodations, and unbeatable location, this property presents a rare opportunity to own a **turnkey, income-producing investment** or a luxurious personal getaway in one of Florida’s most sought-after beach destinations.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Samantha Callaway (630-865-3189)
1900 COVE II PL #138, SARASOTA, FL 34242
$599,900203 Days on yellowkey MLS ID: A4672795
1 Days Off yellowkey (back on 5/18/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 860 Built: 1979 Tax: $6,023 (2023)Community: Midnight Cove IiCondo
Taxes:$6,023
Elementary School: None
High School: None
Tax Year: 2023
Middle School: None
Remarks: Under contract-accepting backup offers. Find safety and security from possible inclement weather near your beach dwelling with a top floor unit with eastern exposure at this wonderful Midnight Cove II unit. Priced extremely competitively on Siesta Key, this nicely renovated unit overlooks the boat traffic and wildlife playground that is the intracoastal waterway that runs between Siesta Key and the mainland. A unique opportunity to capitalize on attractive income while utilizing this third-floor perch to drink in a saltwater breeze when your schedule permits. From your sun deck, a wall of glass sliders connects you to the main living space, flooded with cheerful Florida sunshine. Delight in low maintenance living with the handsome LVP flooring throughout the space. The kitchen offers updated cabinetry, chic stainless appliances and granite counters that shine under the recessed lighting. The dining area offers seating for six while the living area is the perfect place to kick up your feet after a day of Siesta Key adventures. The principal suite is bright and fresh with a beautifully renovated full bath. The second bedroom offers an attractive headboard wall. Guests and families will be quite comfortable with the unique, second full bath allowing for a private space to refresh. With amenities that rival or bests many communities, Midnight Cove II is a vibrant, welcoming place to call home with a marina, tennis courts, barbecue area, fitness room and heated pool. You will also enjoy deeded beach access to Crescent Beach, Siesta Key’s renowned beach with powdery white sands along the Gulf of Mexico. Take a stroll or a trolley to any one of the eateries and shopping opportunities along Siesta Key or venture off island and explore Sarasota and beyond!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Rudy Dudon (941-234-3991)
915 SEASIDE DR #412, SARASOTA, FL 34242
$1,799,000122 Days on yellowkey MLS ID: A4681675
REDUCED by $200,000 (10.0%) on 05/18/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1750 Built: 2009 Tax: $16,278 (2025)Community: Siesta Key Beach Residences IiSpa: YesCondo
Taxes:$16,278
Tax Year: 2025
Remarks: Welcome to a premier Siesta Key Beach condo that delivers the ultimate combination of luxury coastal living and high-performing rental income potential. This beautifully updated 3-bedroom, 2-bath condominium is professionally managed through an established onsite program, offering owners a seamless, turnkey experience with the ability to enjoy the home personally while also participating in a proven, income-producing rental program. Located directly on world-famous Siesta Key Beach, consistently ranked among the top beaches in Florida, the U.S., and the world, this property benefits from strong year-round demand for high-end vacation rentals. Whether you’re looking for a beachfront vacation home, a short-term rental investment, or the ideal blend of both, this residence is positioned to deliver outstanding lifestyle value and long-term upside. The current owner has successfully utilized the rental program while still enjoying substantial personal use, making this an exceptional opportunity for buyers seeking a condo with documented rental history and the flexibility to reserve premium seasonal time for themselves. Inside, the condo features a bright, open layout with spacious living areas and finishes that appeal to both owners and guests. Enjoy partial Gulf of Mexico views and Siesta Key Beach scenery from the primary suite, living room, and private lanai—capturing the coastal lifestyle today’s vacation renters are looking for. Owners and guests enjoy access to desirable resort-style amenities, including a sparkling pool, fitness center, concierge services, and professional onsite management. With unbeatable beach access, nearby attractions, and a consistent track record of rental demand, this is one of the most compelling income-producing condos on Siesta Key. Schedule your private showing today and discover the value of owning a luxury Siesta Key vacation rental property.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Kelly Mooney (941-587-8430)
8750 MIDNIGHT PASS RD #302, SARASOTA, FL 34242
$429,000129 Days on yellowkey MLS ID: A4680093
Bed: 1 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 800 Built: 1980 Tax: $4,916 (2025)Community: TortugaCondo
Taxes:$4,916
Remarks: Come live the dream in this great "fully furnished" residence on the south end of Siesta Key. Share amenities with Turtle Bay across the street like tennis, pickleball, and boat slips. Directly on the gulf, enjoy beach and sun year round. Secure, under building covered parking. Washer/dryer combo in unit! This unit is clean and in fabulous condition and comes fully furnished. Situated at the southern end of Siesta Key, it offers a more remote feel. Take the trolley into the village for dinner and shopping. This unit shows excellent and is priced right!
Listing is courtesy of: HOUSEMAX REALTY LLC (941-315-1990)
Listing Agent: Paul Defelice (941-315-1990)
3210 HIGEL AVE, SARASOTA, FL 34242
$11,950,000169 Days on yellowkey MLS ID: A4676047
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3884 Built: 2026 Tax: $26,394 (2025)Community: Siesta Rev OfSpa: YesSingle Family
Taxes:$26,394
Middle School: Booker Middle
Remarks: Under Construction. Perfectly positioned on the highly coveted north end of Siesta Key, this exceptional property overlooks the aquamarine waters of Big Pass and the Gulf of Mexico where dolphins frolic in your backyard. To be custom built by renowned builders - Trend Homes, the residence is thoughtfully designed to capture the very best of island living. The home will feature exquisite custom kitchen cabinetry paired with top-of-the-line appliances, along with elegant stonework and refined millwork throughout. The spacious primary suite offers generous walk-in closets, while expansive windows provide breathtaking water views from nearly every room. Additional highlights include a 3-car garage, and an open, light-filled floor plan ideal for both everyday living and entertaining. Offering over 4,500 square feet of living space, the home includes four bedrooms and four and half bathrooms. Outdoor amenities are equally impressive, featuring a beautiful swimming pool, private boat dock, and seawall. Located just minutes from premier shopping and dining, and close to Siesta Key’s world-famous white-sand beaches, this is a rare opportunity to own a custom waterfront retreat in one of Sarasota’s most desirable locations. There’s still time for the buyer to personalize this to-be-built home by selecting certain design finishes and features to match their style.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Kim Ogilvie (941-951-6660)
324 SIESTA DR, SARASOTA, FL 34242
$1,400,00031 Days on yellowkey MLS ID: A4692790
0 Days Off yellowkey (back on 5/17/2026)
Bed: 5 Bath: 4.0 Gar: 1 Liv Area Sq Ft: 2510 Built: 1950 Tax: $12,328 (2025)Community: Siesta Rev OfSpa: YesSingle Family
Taxes:$12,328
Middle School: Sarasota Middle
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to the #1 beach in the US and top 50 in the world- Siesta Key, FL. Whether you're seeking a primary residence or a high-performing Airbnb investment, this fully renovated 5-bedroom, 4-bathroom coastal contemporary pool home offers the best of both worlds! Ideally situated on an oversized corner lot on Siesta Key and located within city limits, this MOVE-IN READY gem legally qualifies for 7-day minimum rentals, making it a prime opportunity for full-time living, or a lucrative short-term vacation rental. Nestled behind a grand privacy wall, this unique masterpiece provides a true tropical retreat for you and your guests. From the moment you step inside, you'll be captivated by the soaring 12-foot ceilings on both levels, the open concept floor plan, and elegant travertine marble flooring throughout. The primary suite is conveniently located on the first floor, offering both comfort and privacy with French doors that lead to your outdoor private patio. Custom hurricane-impact French doors wrap the entire main living area, seamlessly blending indoor and outdoor spaces, creating a dramatic view of your tropical oasis. Enjoy peace of mind with HURRICANE-IMPACT WINDOWS and DOORS installed throughout the home. Ample on-site parking for up to 4 vehicles adds exceptional convenience for both owners and guests. The chef’s kitchen is fully equipped with high-end finishes, including a gourmet gas range and hood, custom wood cabinetry, quartz countertops, an oversized BLANCO sink, and wine cooler, perfect for hosting and entertaining. Some of the recent upgrades include two brand-new HVAC systems (one for each level), new hot water heater, all new appliances, fresh interior and exterior paint, new landscaping and irrigation, and plumbing complete with a convenient manifold in the garage for your shut off valves. The newly resurfaced pool, paired with new pool equipment, invites you to relax in total serenity. Surrounded by lush, tropical landscaping, the spacious outdoor area offers plenty of room to entertain guests or simply soak in the Florida sunshine in total privacy. This residence is located just four blocks from the nearest beach access at N. Shell Rd, and near the North bridge for convenient access to and from the Key. Take a short ride to the world-famous Siesta Key Beach and Village, where you'll enjoy fine dining, boutique shopping, and vibrant island living. Known for its powder-soft quartz sand, Siesta Key consistently ranks among the top beaches in the United States, making this a premier location for homeowners and investors alike. Call today to schedule your private showing!
Listing Agent: Angela Lista (941-544-6255)
225 HOURGLASS WAY #202, SARASOTA, FL 34242
$510,00063 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!
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Harriet Stopher (404-316-8944)
4034 ROBERTS POINT RD, SARASOTA, FL 34242
$8,500,00030 Days on yellowkey MLS ID: A4693305
Bed: 5 Bath: 4.5 Gar: 6 Liv Area Sq Ft: 5458 Built: 1990 Tax: $52,899 (2025)Community: Elliot M Prop Siesta KeySpa: YesSingle Family
Taxes:$52,899
Remarks: A rare offering on the exclusive enclave of Roberts Point Road, this fully remodeled in 2023 waterfront estate embodies refined coastal luxury, encompassing 5,458 square feet with 5 bedrooms, 4 full bathrooms, and 1 half bath. Showcasing water frontage on both the front and rear with direct, no-bridge access to Sarasota Bay, the home is set on a private 0.64-acre homesite. The property features a brand-new seawall and two exclusive dock settings, including a 16,000 lb boat lift and jet ski lift, along with a private waterfront seating area designed for effortless enjoyment of the serene surroundings. Underground utilities preserve uninterrupted water views, while soaring ceilings and a signature eagle’s nest vantage point elevate the home’s architectural presence and capture breathtaking vistas. Inside, the residence has been masterfully transformed with a refined open-concept design, anchored by a fully redesigned chef’s kitchen featuring Sub-Zero refrigeration, a gas range, new appliances and countertops, and exceptional craftsmanship throughout. Custom millwork, designer lighting, shiplap detailing, and elegant new railings define the home’s modern coastal aesthetic. The thoughtfully designed floor plan offers three distinct kitchen spaces—including a main kitchen, outdoor kitchen, and private guest suite kitchen—along with a private-entry guest residence and a versatile ground-floor loft with dual Murphy beds, providing exceptional flexibility for both everyday living and elevated entertaining. A private elevator services the home, while a new glass front entry door—currently being installed—further enhances its modern coastal presentation. Curated for both comfort and performance, the home is equipped with three new AC systems, a new well, enhanced irrigation and landscaping, a whole-home Generac generator, reverse osmosis and Kinetico water systems, and full smart home integration through Control4 automation, Sonos audio, and a high-end AV infrastructure. Outdoors, a resort-style pool and spa with both gas and electric heating and full app-based control ensure year-round enjoyment. Additional features include a six-car garage with epoxy floors, a bespoke outdoor bar and kitchen, screened enclosure, kayak storage, and a private sand area—culminating in a truly turnkey, design-forward waterfront estate in one of Sarasota’s most coveted locations.
Listing is courtesy of: PHAM REALTY GROUP LLC (941-260-0709)
Listing Agent: Faith Stutzman (941-260-0709)
420 BEACH RD #203, SARASOTA, FL 34242
$1,249,000541 Days on yellowkey MLS ID: A4631493
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1316 Built: 1980 Tax: $10,693 (2025)Community: Siesta Gulf ViewCondo
Taxes:$10,693
Remarks: Paradise Found on Siesta Key! Wake up to Gulf breezes and end each day with a sunset over the water from this direct beachfront condo at Siesta Gulf View. This 2-bedroom, 2-bath residence offers a full west-facing panorama of Siesta Beach and the Gulf from its expansive 31-foot screened and glass-enclosed balcony, accessible from the living room, kitchen, and primary suite. From here you can enjoy both the beauty of the shoreline and the natural dune vegetation that makes this second-floor perspective feel close and connected to the beach. This floor level offers an ideal balance of easy access and elevated views: take the stairs for quick trips to the beach, pool, or parking garage, or use the elevator if preferred. No long waits, no hassle, just effortless access to every amenity. The TURNKEY FURNISHED layout includes a light-filled open kitchen with eat-in nook (perfect as a dinette or office), two spacious walk-in closets, separate laundry room, and generous storage throughout. Recent community updates give peace of mind: milestone inspections complete, all cast iron plumbing replaced in 2024, and new clubhouse roof and landscaping nearing completion, with no special assessments. Siesta Gulf View is a sought-after, gated, 59-unit community offering private boardwalk access to the quartz sands of Siesta Key Beach, plus resort-style amenities: a 25’x40’ heated pool, tennis and pickleball courts, fitness room, grilling areas, and clubhouse. Assigned under-building parking, ample guest parking, first-floor storage, and an on-site management office add convenience. Pet lovers will appreciate that up to two small pets are welcome. Best of all, you’re just blocks from vibrant Siesta Key Village: restaurants, shops, and live music are a short stroll away. Whether you’re seeking a vacation retreat, investment property (one-month minimum rentals allowed up to 12 times/year), or full-time Gulf-front living, this condo delivers the ultimate island lifestyle. Don’t miss this opportunity to claim your piece of paradise.
Listing Agent: Jennifer Russo (212-683-1173)
1332 SIESTA BAYSIDE DR #1332C, SARASOTA, FL 34242
$699,90062 Days on yellowkey MLS ID: A4689488
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1280 Built: 1988 Tax: $7,606 (2025)Community: Gulf & Bay Club BaysideCondo
Taxes:$7,606
Remarks: Turnkey furnished and beautifully updated, this ground-level 2-bedroom, 2-bath residence in Gulf & Bay Club Bayside offers an exceptional blend of comfort, convenience, and Siesta Key lifestyle. Lightly lived in and meticulously maintained, the interior features a renovated kitchen with stainless steel appliances, solid stone countertops, breakfast bar seating, recessed lighting, custom tray ceiling detail, and an open connection to the main living area that enhances both everyday living and entertaining. Large-format tile flooring runs throughout the main living spaces, while both bathrooms have been tastefully updated with stone counters and tiled shower surrounds. The spacious primary suite offers a relaxing retreat with direct access to the screened lanai, and the guest bedroom is well appointed for family and visitors. Coastal furnishings and decor create a true move-in-ready presentation. The oversized screened lanai expands the living space and provides a peaceful setting surrounded by tropical landscaping, with the community walking path just outside leading to the Intracoastal fishing area, tennis and pickleball courts, and the second pool. Ideally positioned within the community, this residence is also just a short distance to the clubhouse, fitness center, BBQ area, and main pool. Owners and guests enjoy deeded beach access through Gulf & Bay Club across the street, placing world-famous Siesta Beach just a short stroll away. Siesta Beach is currently the No. 1 beach in the U.S. in TripAdvisor's 2025 Travelers' Choice Awards, and Sarasota County provides free trolley service connecting Siesta Key Village, Siesta Beach, South Village, and Turtle Beach. The location also offers convenient access on and off the island, with nearby Siesta Key Village offering shopping, dining, and the relaxed island atmosphere that makes this area so desirable. A private garage completes the package. Whether sought as a personal retreat, seasonal escape, or investment opportunity, this updated Gulf & Bay Club Bayside residence is an outstanding opportunity on Siesta Key.
Listing Agent: Shane Lewis (941-685-3252)
5855 MIDNIGHT PASS RD #333, SARASOTA, FL 34242
$499,90083 Days on yellowkey MLS ID: A4685733
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 835 Built: 1976 Tax: $4,433 (2025)Community: Harbor Towers Y & RSpa: YesCondo
Taxes:$4,433
Remarks: THE VIEW, THE VIEW, Location, Location. This is IT! RESORT LIVING UNDER $500,000! EVERY AMENITY AT YOUR FINGERTIPS! BEAUTIFULLY APPOINTED, IMPRESSIVE ENTRANCE WITH WATERFALL, WALK INTO THE LUXURY APPOINTED HUGE FOYER--TURN KEY INCOME GENERATING VACATION HOME! STUNNINGLY SELECTED AND DESIGNED UNIT OVERLOOKING THE POOL AND VIEW OF INTRACOASTAL WATERWAY---DESIRABLE 2 WEEK RENTAL WHEN YOURE NOT HERE, BLOCK IT OUT WHEN YOU COME TO ENJOY AND RELAX! ON SITE RENTAL OFFICE TAKES CARE OF IT ALL! Experience the ultimate in luxury coastal living within the waterfront resort community of Harbor Towers Yacht & Racquet Club, one of Siesta Key’s most desirable gated waterfront communities. This beautifully updated sunrise-facing 1 BR, 1 bath home offers breathtaking views of the intracoastal waterway, a completely upgraded oasis to provide modern comfort and elegant coastal style with a gorgeous view of the heated pool and outdoor awning for alfresco dining. Being sold turnkey furnished, this third-floor residence is decorated for immediate enjoyment as a full-time home, vacation getaway, or income-producing investment property. The stunningly renovated interior features hurricane-rated windows, a breathtaking quartz kitchen, vinyl plank wood floors and a stunning bathroom accented in gold. The open-concept living and dining area is filled with natural light, creating a bright and welcoming space ideal for relaxing or entertaining. Included is a washer and dryer, plenty of extra storage space directly across the hall and additional large washers and dryers located on each floor for larger items. Perfect for couples and extended stays, this retreat combines modern coastal finishes, large windows, and resort-style amenities just minutes from world-famous Siesta Key Beach and Siesta Key Village. For boating enthusiasts, you’ll find a beautiful marina with boat slips, as available, through the association. This property offers excellent income potential. Two-week minimum rentals are permitted, and owners may utilize the on-site property management office or manage rentals independently. Residents of Harbor Towers enjoy an exceptional collection of amenities, including: *A large marina *Gulf access (no fixed bridges) *Heated swimming pool and shallow wading pool *Three tennis courts *Fully equipped fitness center with new showers and saunas *Clubhouse with social spaces and large kitchen •Outdoor BBQ and kitchen prep area under a beautiful new awning *For boating enthusiasts, boat slips are available through the association plus an ample kayak storage area. Whether you're seeking a luxurious full-time residence, seasonal retreat, or income-generating property, Harbor Towers offers the perfect blend of resort living and coastal charm. Located near shops and restaurants and across the street from the world-famous Siesta Key Beach, don’t miss this rare opportunity to own your piece of paradise on Siesta Key.
Listing is courtesy of: JUDITH GUZZI & ASSOCIATES LLC (914-490-9032)
Listing Agent: Rosie Dipasquale (614-313-7962)
9000 MIDNIGHT PASS RD #5, SARASOTA, FL 34242
$1,350,000104 Days on yellowkey MLS ID: A4683685
REDUCED by $145,000 (9.7%) on 04/29/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1982 Built: 1982 Tax: $7,904 (2025)Community: Turtle CoveCondo
Taxes:$7,904
Remarks: Unique among others for sale on Siesta Key, this 3-bedroom waterfront condo, located on the quiet south end of the island, offers: • Full Views of the Gulf, Blind Pass Lagoon (which connects to the Intracoastal Waterway, the ICW) and Turtle Beach • Two screened porches facing the Gulf from different levels • An easy 5-minute walk through a park to Turtle Beach • A heated waterfront pool steps from the back door • The use of a boat slip and kayak launch directly behind the unit, with direct access to the ICW • A 10-minute boat ride from the slip to the Gulf via Midnight Pass • Living in a quiet area that feels more “residential”, but is within walking distance of 2 waterfront restaurants and only minutes by car or trolley to shopping, restaurants, and entertainment in Siesta Key Village • A back yard lawn and patio • Kayaking in the lagoon and ICW • Fishing in the lagoon from the backyard or community piers directly behind the unit • A pet-friendly environment • A wood-burning fireplace • An oversized 2-car garage with inside access to the unit • A soundproof townhome with no neighbors above or below You will be mesmerized by water views and sunsets from every level of the home and from almost every room in the home. Enjoy spotting pelicans, herons, ibis, jumping fish, and an occasional dolphin or manatee. This 7-unit community, “Turtle Cove”, features the use of 7 equal boat slips, to which lifts could be added. Mature foliage blocks the eastward views of neighboring buildings. The expansive windows and sliding doors are impact-resistant throughout. There is a large, screened, covered porch on the main floor with wall-to-wall windows and sliding doors. The eat-in kitchen is large, bright, and equipped with stainless steel appliances and a convenient pass-through to the dining room. The bedrooms are graced with cork flooring, which is beautiful, quiet, and comfortable. The primary suite faces west with a private, screened porch where you will enjoy sunsets over the Gulf and beautiful reflections on the lagoon. The primary en-suite bathroom features twin sinks, a walk-in shower, and a garden tub. All 3 bathrooms have granite countertops. The primary bedroom and second bedroom have walk-in closets. All bedroom closets are fitted with Closet-Tec fixtures. The third bedroom features 2 single Murphy beds, each complete when opened with dimmable overhead lighting and a power outlet perfect for charging devices while you sleep. The laundry closet is conveniently located near the 3 bedrooms. The downstairs is stunning, with bright light and wall-to-wall impact glass windows and sliding doors to the patio. The 2-car garage is larger than most at 22’ x 24’. A lift (elevator) could be installed in this unit. The location is ideal: a quiet, residential area just 10 minutes from the Stickney Point bridge to the mainland, within walking distance of restaurants, and adjacent to the final, southbound stop of the Siesta Key trolley, a free ride from your home to Siesta Key Village and its shopping, dining, and entertainment venues.
Listing is courtesy of: ZITELLI REALTY NETWORK LLC (813-399-9985)
Listing Agent: Eric Zitelli (813-444-3998)
5400 OCEAN BLVD #8-05, SARASOTA, FL 34242
$690,000218 Days on yellowkey MLS ID: A4670371
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 522 Built: 1970 Tax: $6,969 (2025)Community: Beach TerraceCondo
Taxes:$6,969
Remarks: BEACH TERRACE - STUDIO GULF-FRONT RESIDENCE: YOUR PERFECT SIESTA KEY PIED-À-TERRE Discover your ideal coastal escape at Beach Terrace, perfectly positioned at the end of Siesta Key Village with direct Gulf of Mexico frontage. This charming studio residence offers the perfect pied-à-terre for those seeking an effortless weekend getaway to paradise. Whether you call Sarasota or Lakewood Ranch home, imagine having your own Siesta Key retreat just moments away, a place to unwind, recharge, and embrace the coastal lifestyle whenever you need it. The private balcony frames stunning Gulf views, while the thoughtfully designed interior maximizes space and comfort. Covered parking provides convenient, weather-protected access to your beach escape, while the residence's prime location puts you steps from all the dining, shopping, and entertainment that Siesta Key Village has to offer. No need to drive once you arrive, everything is at your fingertips. Resort-style amenities elevate the experience: enjoy the elevated heated saltwater pool with its spectacular sunset views (truly the best amenity besides the unbeatable location), stay active in the fitness center, gather in the community room, and access the world-renowned Siesta Key Beach directly from the property. The powdery white sand and crystal-clear waters are quite literally your backyard. More than a weekend residence, this is your personal gateway to the Gulf-front lifestyle. Whether it's a spontaneous Friday escape or a planned coastal retreat, your Siesta Key sanctuary awaits. This is the effortless beach lifestyle you've been dreaming of, close to home, yet worlds away.
Listing Agent: Mickey Kiernan (941-402-9115)
625 BEACH RD #602, SARASOTA, FL 34242
$999,000233 Days on yellowkey MLS ID: A4669231
1 Days Off yellowkey (back on 5/17/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1144 Built: 1975 Tax: $8,966 (2024)Community: Tivoli By The SeaCondo
Taxes:$8,966
Remarks: Under contract-accepting backup offers. PRICE REDUCTION OF NEARLY $300,000!!! MOTIVATED SELLERS! DIRECT GULF VIEWS accompany this FULLY REMODELED two-bedroom, two-bath PENTHOUSE offering WEEKLY RENTALS AT TIVOLI BY THE SEA on SIESTA KEY. The residence is presented TURNKEY FURNISHED and ready for immediate occupancy or rental. Comparable units in Tivoli generate APPROXIMATELY $100,000 IN ANNUAL BOOKINGS providing an excellent opportunity to own a piece of Siesta Key while enjoying personal use and potential income. This BEACHFRONT CONDO boasts sophisticated modern design and a tranquil beachside ambiance in a prime, secluded yet connected location. A SPACIOUS 26' X 6' BALCONY OFFERS PANORAMIC GULF VIEWS ideal for enjoying sunrise coffee or sunset cocktails. The living areas feature sleek lines, a neutral palette, and abundant natural light to create an airy atmosphere. The STATE-OF-THE ART KITCHEN is equipped with PREMIUM FIXTURES, TOP-TIER STAINLESS STEEL APPLIANCES including a SUBZERO REFRIGERATOR, STONE COUNTERTOPS, and CUSTOM WOOD CABINETRY. Plush bedrooms provide comfort and serene views, with the master suite featuring direct Gulf views via sliding glass doors, a SPA -INSPIRED ENSUITE BATHROOM WITH HIGH-END FINISHES, and a large walk-in closet. For added assurance, this sixth-floor unit includes MAXIMUM HURRCANE PROTECTION WITH FULL ELECTRIC METAL ROLL-DOWN SHUTTERS. Residents enjoy access to a SWIMMING POOL, poolside cabana with billiard and ping pong tables, ROOFTOP CLUB ROOM WITH EXPANSIVE GULF VIEWS, private tennis and basketball courts, putting green, FITNESS CENTER, and PRIVATE GATED ACCESS to Siesta Key Beach. The community is within walking distance to Siesta Key Village’s restaurants, boutiques, bike rentals, and vibrant nightlife. This property exemplifies elegance, comfort, and the beauty of oceanfront living. It presents a unique lifestyle opportunity for discerning buyers seeking both luxury and investment potential. CALL FOR YOUR SHOWING TODAY!
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Susanne Losso (941-928-0023)
4634 HIGEL AVE, SARASOTA, FL 34242
$6,990,00026 Days on yellowkey MLS ID: A4693756
Bed: 5 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 3875 Built: 2024 Tax: $36,904 (2025)Community: Ocean Beach RepSpa: YesSingle Family
Taxes:$36,904
Remarks: Start living your dream lifestyle on world-famous Siesta Key in this Pham Development custom-built waterfront British West Indies–style home. Located on a quiet street on the north end of the key—close to the beach, Siesta Key Village and Out-of-Door Academy—and just minutes on and off the island, this residence offers island living at its best. Set on a corner canal-front lot, the two-story home features 5 bedrooms, 5 full bathrooms and 1 half bath, with 3,875 square feet under air, a great room floor plan, soaring 22-foot vaulted ceilings, and walls of windows and doors—including large pocket sliders—that bring in abundant natural light and seamlessly connect indoor and outdoor living. The adjacent dining area provides ample space for entertaining, while the stunning kitchen—completely open to the great room—serves as the heart of the home with a large 9-foot island with extended seating, professional stainless steel gas appliances and a walk-in butler’s pantry. The home also features a fully integrated security system, whole-home sound system and a complete Control4 smart home system. The first-floor owner’s suite offers a private retreat with a walk-in shower, freestanding tub, dual vanities, and a large custom walk-in closet. A laundry room, powder room and mudroom complete the first level, and a 3-car garage provides ample parking and storage. Upstairs you’ll find four en-suite guest bedrooms, an additional laundry area to service them, and an expansive second-level balcony to take in the views. Outdoor living includes approximately 1,502 square feet of covered lanai, an exterior wrap-around porch, and balcony space designed for enjoying the island lifestyle, complete with SunBrite outdoor TVs, and Brazilian hardwood ceilings. The privately gated driveway and fully fenced property are surrounded by lush landscaping, creating a secluded tropical setting with a large swimming pool, champagne spa and expansive pool deck perfect for relaxing or entertaining. A private well supports irrigation. With 31 linear feet of canal frontage, the property features a 31-by-12-foot electric boat lift rated for 6,500 pounds, two jet ski ramps and about a 4.5-foot draft—ideal for boating and enjoying the water, making this oasis the perfect place to enjoy the Siesta Key lifestyle.
Listing is courtesy of: THE STUTZMAN REALTY GROUP, LLC (941-260-0709)
539 AVENIDA DEL NORTE, SARASOTA, FL 34242
$5,499,000142 Days on yellowkey MLS ID: A4679096
Bed: 5 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 4195 Built: 2026 Tax: $7,935 (2025)Community: Archibald ResubSpa: YesSingle Family
Taxes:$7,935
Remarks: One or more photo(s) has been virtually staged. Pre-Construction. To be built. EXQUISITE NEW CONSTRUCTION ON SIESTA KEY: ISLAND LUXURY REDEFINED | Substantial progress has taken place to complete this home. | A rare opportunity to own a meticulously designed custom residence on a prime corner parcel of approximately one-quarter acre, just blocks from world-renowned Siesta Key Beach. Easily accessible from both the north and south bridges, this exceptional new build delivers the ultimate coastal lifestyle where refined interiors meet effortless outdoor living. | SIESTA Key Beach is frequently recognized as one of the best beaches in the U.S. and worldwide, celebrated for its powder quartz sand and crystal-clear waters. Its global reputation has been affirmed by TripAdvisor’s Travelers’ Choice Best of the Best Beaches and Dr. Beach’s annual rankings, making this location as iconic as it is desirable. | MOMENTS from Siesta Key Village, enjoy efficient access to boutique shopping, coffee shops, and acclaimed dining while still benefiting from an extraordinary amenity, your own private boat dock access on the canal just across the street. Spend the day boating and return home with ease, parking your vessel at your own dock, a true island luxury. | THIS thoughtfully curated residence reflects the vision of a hands-on developer deeply involved in every aspect of design, from interior finish selections to landscaping and amenities. Created for buyers who appreciate craftsmanship and fine detail, the home offers 4,195 sq ft of interior living space and an additional 3,756 sq ft of outdoor living, seamlessly blending indoor and outdoor environments. | THE chef’s kitchen is designed for both entertaining and everyday ease, complete with a “dirty kitchen” for behind-the-scenes preparation. The light-filled great room opens to a nearly 50-foot wraparound terrace, creating a spectacular setting for hosting family and friends. | TWO bedrooms are located on the main living level, ideal for guest suites or a secondary primary. Take the stairs or elevator one level up to access the private primary suite featuring a truly custom bath with bespoke tile, finishes, soaking tub and spacious shower that creates a spa-like retreat. Two additional bedrooms with a shared bath complete the upper-level.| FLEXIBLE, elegant, and intelligently executed, the suite of spaces within this home allows effortless tailoring to any family’s lifestyle from multi-generational living to a dynamic entertainer’s paradise. | IMAGINE a home where the luxuries of island beach life blend with a private, resort-style retreat: *Inground pool & spa for cooling off or casual lounging*Rooftop deck for sunset cocktails and starlit conversation*Private boating access just steps from your front door. | AND, when you’re ready for a taste of city life, Downtown Sarasota’s rich cultural tapestry with its farmers markets, arts, galleries, festivals, waterfront parks, and world-class dining is only a short drive away. |THIS is more than a home, it’s an invitation to own your piece of the new Siesta Key lifestyle: elevated, effortless, and extraordinary.
Listing Agent: Lisa Otte (941-281-5472)
5920 MIDNIGHT PASS RD #1003, SARASOTA, FL 34242
$1,350,00097 Days on yellowkey MLS ID: A4683544
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1334 Built: 1971 Tax: $10,983 (2025)Community: Sarasota Surf & RacquetSpa: NoCondo
Taxes:$10,983
Remarks: Great Opportunity at Sarasota Surf & Racquet Club!! Beautifully turn-key furnished 2BR/2BA condo with a split bedroom floorplan for privacy in Tower 10 Unit 3 right on the beach with a gorgeous view of the Gulf and the beautiful quartz sand beach and shoreline. The onsite rental management team takes care of your investment. You use it when you want and enjoy the great revenue stream coming your way with a rare and great opportunity to take advantage of their 3 night rental minimum policy and managing all the reservations and taking care of the upkeep and cleaning of your unit. This is really exceptional beachfront living on Siesta Key with so many resort style amenities. You have direct access to private Crescent Beach, two heated swimming pools, rental options for tents, cabanas and umbrellas, beachside and poolside BBQ grills, four pickleball courts, three tennis courts (one hard court and two Har-Tru clay) – the only clay courts for a resort community on Siesta Key. There is a fitness center on the property and a recreation room where owners can come together for fun. The interior of this unit has been re-modeled with a lovely coastal look. Both bathrooms have been beautifully re-modeled. The primary bedroom features a king size bed, large walk-in closet and has its own private vanity area and a stunning tiled walk-in shower with a seat and gorgeous glass block. The second bedroom features two queen size beds and large walk-in closet. There is a lanai/room looking out to the beach and Gulf that is perfect for a quiet space for reading or computer work. Washer and Dryer located in laundry room just steps from the unit. This resort style property has it all! Catch the trolley or walk into the Siesta Key village for great shops and lots of great casual dining or more polished dining experiences. Coastal music flows out from the open air fun places for entertainment. Come enjoy Paradise!!!
Listing Agent: Jay Mitchell Jr., Pllc (941-586-1754)
527 BEACH RD, SARASOTA, FL 34242
$3,195,000111 Days on yellowkey MLS ID: O6384340
INCREASED by $220,000 (7.4%) on 05/15/2026
Bed: 4 Bath: 0.0 Liv Area Sq Ft: 1803 Built: 1985 Tax: $18,981 (2025)Community: Sarasota BeachApartment
Taxes:$18,981
Remarks: Discover an exceptional income-generating property in the heart of coveted Siesta Key right on Beach Road! This fully renovated raised multi-unit compound features a spacious 2-bedroom, 2-bathroom unit and a 2-bedroom, 1-bathrooom unit (side by side). An impressive gross income in 2023 and n 2024 (despite hurricane-related downtime), this turnkey investment provides immediate cash flow. Note: This property is zoned an RMF (Residential Multifamily) and is legally able to accept nightly rentals. The property boasts recent upgrades including new AC (2022), updated flooring (2025), modernized plumbing (2022), electrical (2022), and hot tubs (2022). This amazing opportunity is the best cap rate on any house on Siesta Key. Whether you're seeking a high-performing Airbnb rental portfolio or a strategic redevelopment opportunity in one of Florida's most desirable beach destinations, this property delivers both immediate income and long-term appreciation potential. Absentee owner managed; turnkey operation available at on a management fee with all staff staying in place. This house already has engineering drawings to enclose the bottom area adding 2,000 additonal square foot, that would increase rent by or more. This property could be purchased as a portfolio with 5228 Calle Menorca and 6550 Sabal Road.
Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)
Listing Agent: Steven Koleno (804-656-5007)
19 WHISPERING SANDS DR #201, SARASOTA, FL 34242
$899,000138 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!
6300 MIDNIGHT PASS RD #702, SARASOTA, FL 34242
$1,749,00041 Days on yellowkey MLS ID: A4692155
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1240 Built: 1970 Tax: $9,386 (2025)Community: Crystal Sands 2Condo
Taxes:$9,386
Remarks: Set on the 7th floor of Crystal Sands, this fully updated residence offers a front-row position to the Gulf, with sweeping views stretching south along Crescent Beach toward Point of Rocks. Located in the sought-after “2” stack, the building sits just steps from the sand, creating a rare level of proximity to the shoreline with water views from every room. The 2-bedroom, 2-bath split floor plan is both functional and well-balanced, offering privacy between suites while keeping the main living space open and connected. Wide-plank flooring runs throughout, leading into a light-filled living and dining area that opens seamlessly to the Gulf beyond. A 30+ foot lanai spans the width of the residence and is accessible from both bedrooms and the main living area, creating an easy indoor-outdoor flow and a natural extension of the living space for everyday use. The kitchen is finished with shaker-style cabinetry, quartz countertops, a center island with bar seating, and stainless appliances, designed to feel clean, current, and easy to live in. Both bedrooms are well-proportioned with direct lanai access and calming water views, while the bathrooms have been thoughtfully updated with refined finishes, frameless glass showers, and cohesive tilework that carries the modern coastal aesthetic throughout the home. Residents of Crystal Sands enjoy direct beach access, a Gulf-front pool, and a prime location just minutes from Siesta Key Village’s dining and shops. With its combination of view, proximity to the sand, and updated interiors, this is one of those residences that simply works the moment you walk in.
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Curt Ware (941-587-9122)
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