Location: Sarasota
Keyword(s): Sarasota High
Keyword(s) High School: Sarasota High
Do Not Show Listings
259 ROBIN DR, SARASOTA, FL 34236
$7,900,000114 Days on yellowkey MLS ID: A4675575
Bed: 3 Bath: 4.0 Liv Area Sq Ft: 4078 Built: 1996Monthly Fee: $110 Tax: $31,490 (2024)Community: Bird Key SubSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$31,490
Elementary School: Southside Elementary
High School: Sarasota High
Tax Year: 2024
Middle School: Booker Middle
Remarks: An exceptional opportunity on coveted Robin Drive in Bird Key, this fully reimagined bayfront home captures Sarasota’s waterfront lifestyle at its finest. Recently transformed through a meticulous, top-tier renovation, the residence showcases impeccable craftsmanship, elevated finishes, and a seamless blend of sophistication and comfort—where every detail and major system has been thoughtfully curated for effortless, modern coastal living. Elevated above the floodplain with a ground level over 10 feet, sweeping panoramic views span Sarasota Bay, the downtown skyline, and the iconic Ringling Bridge—creating a breathtaking backdrop from sunrise to sunset, with city lights shimmering across the water in the evening. Inside, more than 4,000 square feet of light-filled living space unfolds across two thoughtfully designed levels. Soaring ceilings up to 14 feet and expansive walls of glass bathe the interiors with natural light while framing unobstructed bay views throughout. The main living areas flow seamlessly from the inviting sitting room with a statement fireplace to the dining area and custom-designed kitchen, opening to the family room with a built-in bar—a wonderful gathering area to enjoy the gorgeous backdrop of the bay and downtown lights. The kitchen is anchored by a striking waterfall island and features designer-appointed custom cabinetry, premium Sub-Zero, Wolf, Bosch, and Miele appliances, and refined integrated details throughout. A fully equipped back kitchen and pantry, complete with an additional sink, appliances, and generous prep space, enhances functionality while maintaining a clean, polished aesthetic. The primary suite, privately positioned on the main level, offers direct access to the pool, dual walk-in closets, and a spa-inspired bath with a soaking tub, dual vanities, and elegant finishes. A dedicated office and two powder baths complete the main level. Upstairs, two en-suite bedrooms with bay views, a versatile bonus room, and an additional office space provide comfortable accommodations for family and guests. Outdoor living is equally compelling, featuring an expansive paver terrace, heated pool and spa, and unobstructed views of Sarasota Bay, downtown, and the Ringling Bridge—creating a serene waterfront retreat designed for everyday enjoyment. Set on protected waters, the property offers 120 feet of deep-water frontage along Bird Key’s Pompano Pass, with direct access to Sarasota Bay, Big Pass, and the Gulf. A newly constructed seawall and Trex dock feature fish and dock lighting, a 24,000-pound boat lift, and dedicated kayak and jet ski lifts—perfectly suited for an exceptional boating lifestyle. Additional highlights include a circular driveway, three-car garage with Tesla charger, and irrigation well. Bird Key offers an exceptional coastal lifestyle in one of Sarasota’s most coveted neighborhoods, just moments from downtown’s restaurants, shopping, and cultural venues, as well as the boutiques and dining of St. Armands Circle and the shoreline of Lido Beach. The Bird Key Yacht Club is currently undergoing a full redevelopment and is expected to reopen as a premier destination for boating, tennis, dining, and an active social scene.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Courtney Tarantino (941-893-7203)
5723 EASTWIND DR, SARASOTA, FL 34233
$655,900120 Days on yellowkey MLS ID: A4675503
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 2206 Built: 2004Monthly Fee: $46 Tax: $6,761 (2024)Community: Three OaksSingle Family
Taxes:$6,761
Elementary School: Ashton Elementary
Middle School: Sarasota Middle
Remarks: Welcome to this well-loved 3-bedroom, 2-bath home located in a quiet, beautifully maintained community that offers a blend of comfort, care, and easy Florida living. Every space has been thoughtfully maintained, creating a truly move-in-ready home. Inside, you'll find a bright and inviting layout with comfortable living areas, a functional kitchen ideal for everyday use, and bedrooms that each provide a cozy retreat, and a generous office space. Step outside to a peaceful backyard—perfect for morning coffee, evening sunsets, or simply enjoying the Florida outdoors. Big-ticket updates are already done, including a NEW roof 25', NEW pool heater, and a NEW HVAC 25', offering added peace of mind. Conveniently located near shopping and dining, just 8 miles from the world-famous Siesta Key Beach, and with easy access to I-75. This charming property is ready for its next chapter—schedule your showing today.
Listing is courtesy of: MARCUS & COMPANY REALTY (941-932-8550)
Listing Agent: Marina Paige (941-263-9545)
6285 MIDNIGHT PASS RD #406, SARASOTA, FL 34242
$799,000167 Days on yellowkey MLS ID: A4670228
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1456 Built: 1981 Tax: $3,221 (2024)Community: Excelsior Beach To Bay 5Condo
Taxes:$3,221
Elementary School: Phillippi Shores Elementary
Middle School: Brookside Middle
Remarks: Welcome to this beautiful Penthouse end unit at the highly desirable Excelsior Beach to Bay community. Perfectly positioned on the Bay side, this 2 bedroom, 2.5 bath condo offers an open, airy layout enhanced by vaulted ceilings, abundant natural light, and impact windows throughout for peace of mind and energy efficiency. The living and dining areas flow seamlessly together, creating an ideal setting for entertaining or relaxing. The dining area features a mirrored accent wall, a built-in cabinet under the stairs, and another built-in at the end of the room for elegant storage and display. A wood staircase leads to the loft, a rare feature in this complex. The spacious loft includes a half bath, and 2 generous closets, offering flexibility as a guest retreat, office, or media room. The loft expands your living options beautifully. The kitchen is both functional and stylish, featuring wood cabinetry, Cambria quartz countertops, marble floors, a tray ceiling and a built-in eat-in area/desk. A window over the sink provides a charming peek of the Bay. The Primary Bedroom impresses with soaring vaulted ceilings, custom built-in furniture, and a bright, open feel, while the Primary Bath offers two separate sink areas with granite counters, built-in cabinetry, and a wall of closets-providing abundant storage and space. Pella sliding glass doors lead to the Florida room/lanai, enclosed in glass and framed by vaulted ceilings invites you to relax and enjoy tranquil views year-round. Residents of Excelsior enjoy private beach access, along with two heated pools, fitness center, tennis and pickleball courts, and clubhouse. Whether you’re seeking a full-time residence, vacation getaway, or investment opportunity, this Penthouse condo offers a rare blend of comfort, style, and location.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Stacy Liljeberg (941-544-6103)
2135 DATURA ST, SARASOTA, FL 34239
$1,800,00032 Days on yellowkey MLS ID: A4685791
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 2539 Built: 2021 Tax: $7,357 (2025)Community: Grove Lawn RepSingle Family
Taxes:$7,357
Tax Year: 2025
Remarks: This beautifully crafted custom home blends modern farmhouse design with thoughtful details and quality finishes throughout. Offering 3 bedrooms, 2.5 baths, and an open floor plan, the home is designed for comfortable living and effortless entertaining. From the moment you arrive, the exterior showcases distinctive character with a cypress wood garage door, cypress porch accents, and a striking glass entryway. Inside, the two-story layout is filled with natural light, European oak flooring, and recessed lighting throughout, creating a warm and inviting atmosphere. The main living space features a dramatic 12-foot vaulted ceiling highlighted by a decorative cypress beam and an electric fireplace, making the great room a welcoming focal point of the home. The open-concept design flows seamlessly into the chef’s kitchen, which is both stylish and functional. It features a Fulgor Milano dual-fuel range, Silestone quartz countertops, custom wood cabinetry with soft-close drawers, and a large waterfall-edge island. Floating cypress wood shelves, brass light fixtures, and a spacious walk-in pantry add both character and practicality. The primary suite provides a relaxing retreat with a spacious bedroom, walk-in closet with custom shelving, and a thoughtfully designed bathroom featuring dual showers, double vanities, and cypress shelving. Additional highlights include beautiful wood stairs with a wrought iron railing leading to a second-story bonus room, along with a large laundry and mudroom combination offering abundant storage and counter space. Outside, the spacious backyard offers ample room for a future pool and is enclosed by a six-foot cypress shadowbox fence, creating a private setting ideal for pets, gatherings, and outdoor enjoyment. Ideally located east of the Trail in Sarasota, the home is just a few blocks from Sarasota Memorial Hospital, Southside Village, and Southside Elementary School. Downtown Sarasota’s vibrant dining, arts, and cultural scene — along with the area’s world-renowned Gulf beaches — are only a short drive away.
Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: Jennifer Thompson, Pa (941-928-0790)
5569 CAPE LEYTE DR, SARASOTA, FL 34242
$4,495,00034 Days on yellowkey MLS ID: A4685577
Bed: 5 Bath: 4.0 Liv Area Sq Ft: 3654 Built: 2016 Tax: $32,419 (2025)Community: Siesta IslesSingle Family
Taxes:$32,419
Remarks: LOCATION, LOCATION, LOCATION !!! One Block to the Crystal Sands of Siesta Key Beach the #1 Beach in the USA! Or spend the day on the Aqua waters with two boats on lifts out back, and 119' of frontage on the Grand Canal leading to the ICW (only one bridge with about 15’ clearance to the Gulf). Oversized 16,163 sf Lot, elevated concrete block home and spectacular pool in your view from most every room! Not just the best location, but this custom-built in 2016 West Indies style home is a fortress all on one level, including the pool, and is well above the FEMA flood zone. High and dry through the "storms of the century" in 2024. Beautiful, engineered hardwood floors, custom cabinetry throughout by Elite Woodworking in the Kitchen, all Bathrooms and Great Room. The entire house has been freshly painted inside & out. Three large en-suite bedrooms. Additional rooms currently utilized as office with Murphy Bed as well as very large Bonus Room could be utilized as additional bedrooms #4 & 5, if desired. Even the powder bath has a shower for guest convenience. Large walls of sliding glass doors in all waterfront rooms extend living spaces to a huge, screened Lanai which adds over 500 sf to living space under roof, and much more in the screened Lanai area.. All hurricane rated extra heavy duty PGT doors and windows. The total A/C space is 3,654 sf, with a overall total of 5,075 under roof. The oversized 3-car garage with an Epoxy floor has a very high ceiling which allows 2 more cars to be added on lifts for a total of 5 vehicles for the enthusiast. Isonene insulated and floored attic storage space is available above the garage. New in the past year: A/C Condenser & Air Handler system in 1 (of 2) zones, water heater, refrigerator, ice maker, boat lift control boxes on both Lifts. The large free form pool and spa have new (wifi) Pentair pool pump & heater & auto chlorinator. Both boats as well as professional decorator staged furniture, decor and pictures may be available for separate purchase for "Turn-Key" possession. DEFINITELY check out the Virtual Tour, since it provides “3D walk through any direction” photos which can really give you the flow of the house as you manipulate your way around.
Listing Agent: Steve Hagan (941-900-4126)
101 S GULFSTREAM AVE #9A, SARASOTA, FL 34236
$490,00092 Days on yellowkey MLS ID: A4678189
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1200 Built: 1974 Tax: $4,539 (2025)Community: Dolphin TowerCondo
Taxes:$4,539
Remarks: Live the Florida lifestyle where every day feels like a getaway in this well-maintained 9th-floor, 2-bedroom, 2-bath condo ideally located in the heart of downtown Sarasota. Just steps from Sarasota Bay, Bayfront Park, O'Leary's Tiki Bar & Grill, and Marina Jack, this move-in-ready residence offers the best of walkable coastal city living. Enjoy Palm Avenue views from your private balcony or step out the rear entrance for immediate access to the weekly farmers market, art festivals, dining, galleries, and shopping. The 101 Condominium features resort-style amenities including a renovated lobby, fitness center, heated pool with expansive deck and ambient evening lighting overlooking the bay and park, grilling area, pergola, and resident club space. Additional highlights include gated under-building reserved parking, storage unit, bike storage, and guest parking, all just minutes from St. Armands Circle, beautiful beaches, boating, and performances at Van Wezel Performing Arts Hall.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Susan Katanic (941-400-0601)
3664 TIN CUP BLVD, SARASOTA, FL 34232
$469,00084 Days on yellowkey MLS ID: A4679323
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1578 Built: 2016Monthly Fee: $345 Tax: $3,201 (2024)Community: Enclave/Frst LakesVilla
Taxes:$3,201
Elementary School: Wilkinson Elementary
Remarks: ***STUNNING END UNIT IN A PREMIER ENCLAVE AT FOREST LAKES LOCATION*** Experience exceptional Sarasota living in this highly sought-after 2-bedroom, 2-bath end unit, ideally positioned on the largest and most desirable lot in The Enclave at Forest Lakes. Set directly across from the community pool and dog park, this residence offers a rare combination of privacy, convenience, and lifestyle—arguably the best location within the subdivision. The home is filled with natural light and enhanced by its end-unit setting. Recent updates include fresh interior paint throughout and tasteful upgrades in the primary bathroom, creating a clean, modern, and truly move-in-ready feel. The kitchen showcases modern elegance with stainless steel appliances, quartz countertops, and solid wood cabinetry, ideal for everyday living and entertaining. The primary suite serves as a private retreat, featuring updated finishes, dual sinks, a spacious walk-in shower, and a generous walk-in closet, blending comfort with refined style. Roof is only 3 years old! Located within a gated community with no CDD fees, the HOA includes access to the resort-style pool, dog park, and grilling area—all just steps from your front door. Perfectly situated in the heart of Sarasota, this home offers easy access to award-winning beaches, downtown dining and cultural attractions, and top-rated schools. This is a rare opportunity to own an end unit in the subdivision’s most coveted location, where thoughtful upgrades, convenience, and the Sarasota lifestyle come together beautifully.
Listing is courtesy of: MCGREGOR INTERNATIONAL REAL ESTATE CO (941-363-1210)
Listing Agent: Warren Mcgregor (941-447-1253)
3535 VILLAGE GREEN DR, SARASOTA, FL 34239
$490,000129 Days on yellowkey MLS ID: A4674495
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1647 Built: 1968Monthly Fee: $8 Tax: $2,805 (2024)Community: Village Green Club EstatesSingle Family
Taxes:$2,805
Remarks: BRAND NEW VINYL PRIVACY FENCE JUST INSTALLED IN BACK YARD! THIS IS THE ONE! Welcome to your Sarasota dream home in the highly sought-after Village Green Estates! This stunning, fully renovated, 3-bedroom 2-bathroom residence offers luxurious living on a premium oversized lot that sits high and dry! Step inside to discover a home where every detail has been carefully curated. The brand-new kitchen is a chef's delight, featuring sleek waterfall quartz countertops, modern soft close cabinetry, and top-of-the-line finishes. Enjoy the seamless flow of brand-new luxury vinyl plank flooring throughout the entire home, complemented by chic matte black hardware and light fixtures that add a touch of contemporary elegance. Both bathrooms have been completely transformed into spa-like retreats with exquisite tile work and designer vanities. The living space extends outdoors to a screened-in covered lanai, perfect for enjoying the Florida weather in comfort and style. The exterior is just as impressive as the interior. The property boasts new landscaping and paint that enhances its curb appeal, and significant updates ensure the home is move-in ready and low maintenance. Other key features include new impact windows/doors, newer tile roof, new HVAC duct work, and new water heater! Village Green Estates is well maintained and established community that offers the nearby golf clubhouse and no CDD fees, for only a low $100 annual fee! Join the optional golf membership at Village Green Golf Club to enjoy a day out on the course right in your back yard! This is a fabulous location close to everything - Publix Grocery Store, Walmart, Walgreens, Starbucks, Legacy Bike Trail, Downtown Sarasota, I-75, UTC Mall, and Siesta Key!
Listing Agent: Brent Martin, Llc (941-231-4662)
749 TROPICAL CIR, SARASOTA, FL 34242
$1,575,000130 Days on yellowkey MLS ID: A4673529
Bed: 4 Bath: 2.5 Liv Area Sq Ft: 2598 Built: 1984Monthly Fee: $54 Tax: $15,011 (2025)Community: Siestas Bayside Bayside Club 01Single Family
Taxes:$15,011
Remarks: A private tropical haven in the heart of Siesta Key, beautifully reimagined coastal retreat tucked away on nearly half an acre in one of Siesta Key’s most coveted neighborhoods. This stunning four-bedroom, two-and-a-half-bath pool home lives effortlessly, blending relaxed island living with thoughtful modern design, all just minutes from world-renowned Siesta Beach and the vibrant energy of Siesta Village. Completely transformed in 2023 by the former contractor-owner for his family, the residence showcases quality craftsmanship, contemporary finishes, and a warm, inviting aesthetic. Sunlight pours through impact-rated windows, highlighting open living spaces that flow seamlessly toward the outdoors. The expansive great room anchors the home and connects naturally to the newly staged interiors, creating an ideal environment for everyday living and entertaining. At the heart of the home, the chef’s kitchen is an absolute showpiece, featuring a striking reclaimed-oak island, open oak shelving, handmade tile, quartz surfaces, premium appliances, and exceptional storage including a full-height pantry wall. The design balances beauty and function with ease. The spacious primary suite offers serenity and privacy with a spa-inspired bath, while three additional bedrooms provide flexibility for guests, family, a home office, or creative space. A full interior laundry room, half-bath, and oversized two-car garage add convenience. Step outside to your own tropical oasis. A large, screened lanai opens to lush gardens, a newly renovated pool with updated equipment, and an expansive paver deck; perfect for relaxing in the sun or hosting gatherings under the palms. This exceptional property offers peace of mind with solid concrete block construction, no flood or hurricane damage, and a long list of upgrades, including new kitchen, baths, plumbing updates, air conditioning and ductwork, water heater, pool equipment, paver driveway, and more. Move-in ready, beautifully staged and ideally located, this is coastal living at its best. Enjoy quick access to Siesta Beach, the Village, boat launches, dining, and all that Sarasota offers.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Judie Berger (941-928-3424)
5273 HERON WAY #202, SARASOTA, FL 34231
$489,500162 Days on yellowkey MLS ID: A4670409
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1775 Built: 1986 Tax: $5,616 (2025)Community: Landings South 3Condo
Taxes:$5,616
Remarks: Newly installed HURRICANE IMPACT WINDOWS and a 2024 AC with transferable warranty make this second-floor coach home a low-maintenance, move-in ready choice. Enjoy expansive water views and a prime location just a short walk to the Racquet Club and pool in the highly sought-after Landings community. Inside, a bright, open layout features vaulted ceilings and consistent flooring with no step-down, creating a seamless living space. The updated kitchen offers granite countertops, a breakfast bar, and stainless steel appliances, flowing into the main living area with water views. The primary suite also overlooks the water and provides generous space for a sitting or work area, along with a large bathroom and walk-in closet. Two additional bedrooms share a full bath, while plantation shutters add a timeless finish throughout. Additional features include a separate laundry room and a newer roof and gutters installed in 2023. Residents enjoy access to the Landings Racquet Club with eight Har-Tru tennis courts, fitness center, pro shop, heated lap pool and spa, and an active year-round social calendar. A private nature trail leads to a covered dock, fishing pier, and kayak and paddleboard storage. Ideally located west of the Trail, The Landings is minutes from Siesta Key, Southside Village, and Downtown Sarasota, offering excellent dining, shopping, and convenience.
Listing Agent: Yvette Sellyn (941-730-7756)
4822 OCEAN BLVD #2A, SARASOTA, FL 34242
$839,000181 Days on yellowkey MLS ID: A4668724
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1435 Built: 1973 Tax: $7,588 (2023)Community: Siesta TowersCondo
Taxes:$7,588
Tax Year: 2023
Remarks: Price Improvement! Your Coastal Paradise Awaits! Step into a world of elegance and tranquility in this stunning condominium, perfectly situated along the breathtaking coastline of Siesta Key. Featuring two lavish ensuite bedrooms, this residence offers you the ultimate in coastal living. The primary bedroom boasts full panoramic views of the crystal blue waters of the Gulf, complete with a beautifully remodeled bathroom and an expansive walk-in closet designed for the modern lifestyle. Embrace a split floor plan that promotes privacy and relaxation, all within a breezy coastal open-concept design that floods the space with an abundance of natural light. Indulge in the outdoors from two covered balconies, ideal for outdoor dining or savoring a glass of rosé as you watch the sun dip below the horizon in a stunning display of colors. Enter the building through a well-appointed lobby that exudes sophistication and class. Residents enjoy a host of resort-style amenities that include a beautifully remodeled community center for exclusive use, a newly refurbished workout facility, and a gulf-front pool to soak in the sun. The outdoor BBQ area is perfect for gathering with friends and family, while storage for beach accessories and bikes adds to the convenience of a coastal lifestyle. Enjoy the peace of mind that comes with covered parking. Perfectly located, this luxury community allows you to walk, bike, or cruise your golf cart to local restaurants, boutique shopping, live music venues, and the vibrant farmers market, all within minutes from your doorstep. Of course, the soft, white sands of Siesta Key Beach are just a short stroll away, ready to fulfill your beach daydreams. Don't miss your chance to experience luxury coastal living at its finest. Schedule your private tour today and discover your new home in paradise!
Listing is courtesy of: ASCENDIA REAL ESTATE (941-306-4242)
Listing Agent: Beth Dilley (941-400-1322)
9011 MIDNIGHT PASS RD #426, SARASOTA, FL 34242
$569,000181 Days on yellowkey MLS ID: A4668084
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1093 Built: 1974 Tax: $5,686 (2024)Community: Sunrise Cove Sec 4Condo
Taxes:$5,686
Remarks: Location! Location! Location! Great Investment Property, Rent 12 times a year with a 30 day minimum and an onsite management company! Experience true waterfront living with spectacular views all day long of the Intracoastal Waterway from your Condo and breathtaking sunrises every morning! The grounds are absolutely Stunning! This TURNKEY furnished 2-bedroom, 2-bath condo on the 4th floor of Sunrise Cove offers comfort, style, and convenience. The spacious living room features beautiful Hard wood floors and sliding glass doors that open to a screened-in lanai with remote-controlled blinds, and a spectacular views of the Intercoastal Waterway perfect for relaxing and enjoying the panoramic views. The primary bedroom included Hardwood flooring a walk-in closet, and an en-suite bath with a large walk-in shower. The second bedroom also features wood floors, a walk-in closet, and views of the Gulf of Mexico and beach across the street. The hall bath offers a walk-in shower and tile flooring. The kitchen opens to the dining and living areas, creating an inviting open-concept layout ideal for entertaining. Additional updates include a brand-new air conditioning unit (2025) and new water heater (2025) and Brand new Roof (2025) Community Highlights: Two heated swimming pools, including an Olympic-size pool with restrooms and a covered lounge area Pickleball and tennis courts State-of-the-art fitness center and game room On-site management with 30-day minimum rentals, offering great income potential Turtle Beach is just across the street, and the free Siesta Key Breeze trolley stops nearby every 15 minutes Two popular waterfront restaurants, Turtles on the Bay and Ophelia’s on the Bay, are right next door Extra storage closet conveniently located near the elevators in the laundry room Recent community updates: new roofs, new docks, and nearly completed new carports Enjoy the best of Siesta Key living—whether as a vacation home, income-producing property, or full-time residence, this fabulous waterfront condo offers it all!
Listing is courtesy of: MEDWAY REALTY (941-375-2456)
Listing Agent: Sheryl O'Keefe (941-376-2112)
5432 CAPE LEYTE DR, SARASOTA, FL 34242
$1,125,000357 Days on yellowkey MLS ID: A4649500
1 Days Off yellowkey (back on 3/26/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1659 Built: 1974Monthly Fee: $21 Tax: $10,946 (2025)Community: Siesta Isles Unit 2Single Family
Taxes:$10,946
Remarks: Under contract-accepting backup offers. Newly adjusted price - an exceptional opportunity to own a charming beach retreat on Siesta Key minutes from world-famous Siesta Beach—consistently ranked among the best beaches in the U.S. With powdery white sands, crystal-clear turquoise waters, and unforgettable Gulf sunsets close by, this home captures the essence of relaxed island living. Located in the desirable, deed-restricted community of Siesta Isles, this three-bedroom, two-bath residence is set on a lushly landscaped, nearly 15,000-square-foot lot adorned with more than 40 mature palm trees, bromeliads, and a rare, show-stopping staghorn fern. The expansive property offers exceptional outdoor privacy, ample room for entertaining or recreation, and space to add a pool. Inside, the open-concept floor plan features generously sized rooms filled with natural light. A wraparound wall of windows in the living and breakfast areas frames serene views of the tropical backyard, creating a seamless indoor-outdoor connection. The renovated kitchen is thoughtfully designed with white quartz countertops, glass tile backsplash, and newer appliances, while a separate dining room provides comfortable space for gatherings. The primary suite includes an en-suite bath and a tranquil retreat feel. Two additional bedrooms offer flexibility, including a third bedroom with contemporary barn doors—ideal for a home office, den, or guest space. With a base flood elevation of 8'8" the home remained high and dry with no water intrusion during the storms; the elevation certificate and inspection certification are available. Additional highlights include a private, low-maintenance, six-foot fenced backyard, an oversized circular paver driveway with generous parking, and a two-car garage for storage and convenience. The home may be purchased turnkey furnished (with a few exclusions), making it well-suited as a beach getaway, seasonal residence, or income-producing property. Recent improvements totaling over $100,000 add peace of mind and value, including a metal roof (2022), HVAC system (2023), paver driveway (2022), six-foot PVC fencing (2020), and re-piped sewer and water lines. Just one mile from Siesta Village’s boutiques, dining, and live music—and a short drive to downtown Sarasota’s cultural attractions, farmers markets, and waterfront destinations—this property also offers long-term potential as a future residential building site due to its prime island location. With a voluntary HOA of only $200 annually and a newly improved price, this is a compelling opportunity to secure your place on Siesta Key. Schedule your private showing today and experience the island lifestyle you’ve been waiting for.
Listing is courtesy of: PREMIER SOTHEBYS INTL REALTY (941-364-4000)
5560 SHADOW LAWN DR, SARASOTA, FL 34242
$1,549,000448 Days on yellowkey MLS ID: A4636955
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2124 Built: 1970Monthly Fee: $17 Tax: $8,052 (2025)Community: Siesta IslesSingle Family
Taxes:$8,052
Remarks: Siesta Key Waterfront Living—Priced to Embrace the Island Lifestyle An inviting opportunity to enjoy relaxed waterfront living on Siesta Key, this beautifully maintained residence is ideally positioned just moments from the powdery white sands of Siesta Beach and the turquoise waters of the Gulf. Set on an oversized 14,000-square-foot corner lot, this four-bedroom, three-bath home blends comfortable coastal living with everyday functionality in a highly desirable island setting. Designed for effortless entertaining and easy living, the open-concept floor plan centers around a spacious island kitchen with generous seating, breakfast bar, and abundant workspace—flowing seamlessly into the dining and living areas for gatherings both large and small. A thoughtful split-bedroom layout offers privacy for owners and guests alike. The primary suite enjoys peaceful views of the pool and canal, while a secondary bath doubles conveniently as a pool bath—ideal for indoor-outdoor living. Step outside to the covered, screened lanai and unwind beside the sparkling pool, framed by tranquil water views and gentle coastal breezes. Tucked along a quiet harbor just off the Grand Canal, the setting is ideal for kayaking, paddleboarding, or boating, with frequent sightings of manatees and coastal birds adding to the natural charm. Evenings bring glowing “mango sunsets” nearby, while mornings begin with soft sunrises reflected on the water. Additional highlights include an oversized two-car garage and a durable concrete tile roof. Ideally located near the shops, dining, and energy of Siesta Village—and just 15 minutes from downtown Sarasota’s vibrant arts and cultural scene—this home presents a compelling opportunity to enjoy the best of island living, whether as a full-time residence or a serene coastal retreat.
3300 S BENEVA RD #224, SARASOTA, FL 34232
$215,000456 Days on yellowkey MLS ID: A4634478
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1084 Built: 1980 Tax: $2,437 (2023)Community: Fairways & GreensCondo
Taxes:$2,437
Remarks: 0.2 mi to Publix • 3 mi to Sarasota Memorial Hospital • 5.5 mi to Siesta Key Beach • Includes Zillow 3D Tour & Matterport Tour Move-in-ready and fully furnished 2-bedroom, 2-bath condominium in a secured elevator building close to Sarasota’s key amenities. This second-floor residence offers approximately 1,084 sq ft of single-level living with a spacious 9' × 14' screened lanai overlooking the community pool. Recent improvements include hurricane-impact windows and a new roof completed last year, providing peace of mind and energy efficiency. The interior features an updated kitchen and bathrooms, wood-style flooring, and an in-unit laundry room for added convenience. The floor plan includes an open living and dining area with direct access to the pool-facing lanai, creating an ideal indoor-outdoor extension of the living space. The primary suite offers ample storage and an updated bath, while the guest bedroom and additional full bath provide flexibility for visitors or home workspace needs. This condo also includes one assigned covered parking space plus abundant guest parking throughout the community. From this central Sarasota location, reach Arlington Park (2.5 mi) for aquatic facilities, fitness center, tennis, pickleball, basketball, and walking paths. Explore Downtown Sarasota (4 mi) for dining, shops, and Bayfront Park, or head to Siesta Key Beach (5.5 mi) for world-famous coastline. Additional anchors include Legacy Trail access (2.2 mi), Walmart Neighborhood Market (0.9 mi), Starbucks (1.2 mi), Westfield Siesta Key (2.5 mi), and direct routes via US-41 (2 mi) and I-75 (3.8 mi). This furnished condominium combines an updated interior, secured lobby access, an elevator, pool views, and proximity to Sarasota’s beaches, parks, shopping, and medical services. Be sure to view the Zillow 3D Tour and Matterport walk-through for a complete look at the layout and features of Unit 224.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Jill French (941-600-8281)
4819 HIGEL AVE, SARASOTA, FL 34242
$5,392,000606 Days on yellowkey MLS ID: A4620571
Bed: 4 Bath: 5.0 Liv Area Sq Ft: 4220 Built: 2024Community: Siesta BeachSingle Family
Taxes:$0
Remarks: One or more photo(s) has been virtually staged. New Construction. Come see this coastal Siesta Key home located on the Grand Canal. The home is located on prime waterfront property with the best views of the Grand Canal, which provides easy access to the bay. A boater's dream! This three-level waterfront property offers the best in luxurious living, with four spacious bedrooms and four full baths and two half baths. Step inside the impressive front doors into the bright foyer which leads to the spacious great room, well-planned kitchen and bonus and/or dining room. Take in the beautiful wide views of the Grand Canal from your gorgeous pool, spa and travertine deck or while cooking from your outdoor kitchen. The first floor also features the primary bedroom, powder bath, and laundry room. The beauty of the home is the open concept living area which allows for natural light to flow from large windows and slider throughout the space. Located on the second floor are the second and third bedrooms each with their en suite bathroom. On the third floor, you will find another master suite where you can enjoy more waterfront views from its balcony. Enjoy your private den or office with walk in closet and mechanical storage closet. This home is situated in a prime location, just moments away from the world-famous Siesta Key Beach, known for its pristine beaches and clear waters. Close enough to famous Siesta Key Village but still out of the hustle and bustle. Also this home is in walking distance to The Out of Door Academy. Explore local dining and shopping or enjoy all the activities that Siesta Key living provides, fishing, boating, kayaking, walking, biking. You can even golf cart to the Siesta Key Village. Come see for yourself, this brand new residence and feel the Siesta Key life style. This is an exceptional custom home with well appointed extra features that will give you the best, easiest coastal living in Sarasota. Don't miss out on this home! Some photos virtually staged.
Listing is courtesy of: BRIGHT REALTY (941-552-6036)
Listing Agent: Cassie Meyer (941-650-4935)
858 HUDSON AVE #858, SARASOTA, FL 34236
$920,000258 Days on yellowkey MLS ID: A4659647
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1533 Built: 1989 Tax: $11,352 (2024)Community: Hudson LandingsCondo
Taxes:$11,352
Remarks: Live the Downtown Waterfront Lifestyle – Deeded Dock Included! Brand new exterior paint! This beautifully renovated 2-bed, 2-bath condo with a den (optional 3rd bedroom) is a rare find in Sarasota’s desirable West of the Trail neighborhood. Located in Hudson Landings, a quiet 12-residence community just minutes from downtown and the bay, this light-filled second-floor corner unit offers modern updates and an unbeatable lifestyle. The list price includes a deeded dock and a 10,000-lb boat lift—brand new with updated pilings and cradle—providing quick, direct access to Sarasota Bay and the Gulf of Mexico. Bring your boat and enjoy the ultimate Florida living experience! Inside, you'll find a vaulted exposed-beam ceilings and abundant natural light with a sleek contemporary kitchen with custom cabinetry, newer granite countertops, glass tile backsplash, and top-of-the-line stainless steel appliances, including a built-in double oven and glass cooktop, and a spacious Italian-style shower in the updated bathrooms. Plus a cozy wood-burning fireplace for cool evenings and an enclosed patio with large hurricane-rated sliding windows, creating a bright and inviting dining area Step outside and you’re just a short walk to Marie Selby Botanical Gardens, the Sarasota Bayfront, and vibrant downtown Sarasota. This peaceful community also features a heated pool, lush landscaping, and a truly secluded atmosphere—no damage from recent storms Helene or Milton; docks and boats remained intact.
Listing is courtesy of: YORKSHIRE INTERNATIONAL R.E. (941-366-0000)
Listing Agent: Jules Roman (941-366-0000)
1021 CRESCENT ST, SARASOTA, FL 34242
$1,745,00065 Days on yellowkey MLS ID: A4681826
Bed: 3 Bath: 0.0 Liv Area Sq Ft: 2780 Built: 2015 Tax: $17,389 (2025)Community: Siesta/RocksMulti-Family 5+
Taxes:$17,389
Remarks: ***Potential for $150k+ gross income. Zoned for weekly rentals. ONE UNIT IN CONDO COMMUNITY*** Escape to the ultimate Siesta Key lifestyle with this rarely available, coastal contemporary condo—offering the perfect blend of luxury, privacy, and convenience with direct access to the sugar-white sands of world-renowned Siesta Key Beach and Crescent Beach. Known for its quartz-crystal sand and turquoise waters, this top-rated beach offers stunning sunsets, gentle waves, and vibrant coastal charm, all just a short stroll from your door. Nestled in a boutique enclave of only five residences, this exclusive unit has fresh interior paint, lives like a single-family home and is one of only two in its building. This unit encompasses the entire floor and shares no walls with other units. With five private patios, a built-in outdoor grill, tall ceilings and windows, and plantation shutters throughout, the light-filled layout offers an open flow between living, dining, and kitchen spaces—accented by custom cabinetry, upscale finishes throughout. The spacious primary suite provides a private retreat, while the entire home is thoughtfully designed on one level for effortless living. A private elevator offers direct access from your oversized ground-level garage, which is nearly 1,000 square feet and accommodates three vehicles plus storage, along with a private driveway for guest parking — a rare find on the Key. This property is zoned for short-term, weekly rentals and boasts a strong rental history, making it an exceptional opportunity for both personal enjoyment and possibility to earn over $150,000 in investment income. Enjoy walkable access to beachside boutiques, island restaurants, and boat rentals, plus quick and easy access on and off the island, making it ideal for both full-time living and a low-maintenance vacation home. Shared amenities include a serene pool, private owner's clubhouse, and common area used by only five residences, ensuring a peaceful and private setting. Whether you're searching for a serene retreat or a stylish beach escape with income potential, this home offers a unique opportunity to live in the heart of Siesta Key’s coastal paradise. Furnishings optional - not included in list price.
Listing is courtesy of: HARTMAN REAL ESTATE & COMPANY (941-500-4547)
Listing Agent: Zain Hartman (941-735-6415)
1021 CRESCENT ST #1, SARASOTA, FL 34242
$1,745,000110 Days on yellowkey MLS ID: A4676253
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 2780 Built: 2015 Tax: $17,389 (2025)Community: Siesta/RocksCondo
Remarks: Escape to the ultimate Siesta Key lifestyle with this rarely available, coastal contemporary condo—offering the perfect blend of luxury, privacy, and convenience with direct access to the sugar-white sands of world-renowned Siesta Key Beach and Crescent Beach. Known for its quartz-crystal sand and turquoise waters, this top-rated beach offers stunning sunsets, gentle waves, and vibrant coastal charm, all just a short stroll from your door. Nestled in a boutique enclave of only five residences, this exclusive unit has fresh interior paint, lives like a single-family home and is one of only two in its building. this unit encompasses the entire floor and shares no walls with other units. With five private patios, a built-in outdoor grill, tall ceilings and windows, and plantation shutters throughout, the light-filled layout offers an open flow between living, dining, and kitchen spaces—accented by custom cabinetry, upscale finishes throughout. The spacious primary suite provides a private retreat, while the entire home is thoughtfully designed on one level for effortless living. A private elevator offers direct access from your oversized ground-level garage, which is nearly 1,000 square feet and accommodates three vehicles plus storage, along with a private driveway for guest parking — a rare find on the Key. This property is zoned for short-term, weekly rentals and boasts a strong rental history, making it an exceptional opportunity for both personal enjoyment and possibility to earn over $120,000 in investment income. Enjoy walkable access to beachside boutiques, island restaurants, and boat rentals, plus quick and easy access on and off the island, making it ideal for both full-time living and a low-maintenance vacation home. Shared amenities include a serene pool, private owner's clubhouse, and common area used by only five residences, ensuring a peaceful and private setting. Whether you're searching for a serene retreat or a stylish beach escape with income potential, this home offers a unique opportunity to live in the heart of Siesta Key’s coastal paradise. Furnishings optional - not included in list price.
2308 SHADOW OAKS RD, SARASOTA, FL 34240
$1,135,00089 Days on yellowkey MLS ID: A4678649
3 Days Off yellowkey (back on 3/24/2026)
Bed: 4 Bath: 4.0 Liv Area Sq Ft: 4452 Built: 1980 Tax: $5,364 (2025)Community: Shadow OaksSingle Family
Taxes:$5,364
Elementary School: Tatum Ridge Elementary
Middle School: McIntosh Middle
Remarks: Under contract-accepting backup offers. Your private oasis close to everything awaits! Welcome home to this beautiful extensively upgraded 4 bed, 4 bath, 4452 square foot home on over an acre complementing contemporary expectations with timeless country charm. Within you’ll discover a truly flexible living space for modern families & everyone’s hobbies with a master suite option on both floors, spacious living areas, dedicated office & an extra flex room, game room, playroom, gym or guest suite. Or the south wing could simply be a generous multi-generational retreat…. The 2020 renovations enlightened & streamlined the interior with a huge chef’s kitchen & dining room combo, all new bathrooms, updated bedrooms with walk-in closets & flooring too–all while maintaining the home’s warm & inviting character. Two wood-burning fireplaces add a cozy ambiance to both living rooms, upstairs & down. Outside, enjoy true Florida living with a screened-in heated saltwater pool, outdoor kitchen with built-in grill & large covered patio–perfect for entertaining or quiet relaxation. Warblers, sandhill cranes & a little family of deer will bring joy to your days as will stunning sunsets by the pool at night. With 200 feet along peaceful Philippi Creek, this private lot features outdoor lighting, irrigation, mature oaks, bamboo, banana trees, rows of foxtail palms & ample room for all the big & little kid toys you’ve been wishing for! The oversized two-car garage features EV charging, rear garage door, additional storage & extra room. Additional energy & cost-savings bonuses include a 3-zoned HVAC system & other mechanical updates throughout. No HOA or CDD fees. Flood zone X for extra savings & peace of mind. Perfect for nature lovers & exercise enthusiasts, the world-famous Celery Fields bird & nature refuge is 0.4 miles away for you to hike, bike, paddle, fish & birdwatch as a daily routine. When you must run errands, this generous retreat is also only minutes from many shopping/dining choices at Bee Ridge, Fruitville, UTC, Lakewood Ranch & Costco along nearby Interstate exits & is within thirty minutes of the airport, St Armands Circle, Lido & Siesta Key beaches & downtown Sarasota too. Then come home again & disappear into the rare rustic charm of this tropical sanctuary estate.
Listing is courtesy of: SUNCOAST HOMES & DREAMS (941-350-4411)
Listing Agent: Christina Pitchford, Pa (941-350-4411)
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