Displaying: For Sale
Location: Sarasota
Property Type(s): Single Family
Living Area Square Feet: 3500+
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Sarasota - 312 properties found
1444 HARBOR DR, SARASOTA, FL 34239
$6,999,95081 Days on yellowkey MLS ID: O6375298
REDUCED by $500,050 (6.7%) on 04/14/2026
Bed: 5 Bath: 6.0 Gar: 3 Liv Area Sq Ft: 5001 Built: 2002 Tax: $33,037 (2025)Community: Harbor Acres Sec 2Spa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$33,037
Elementary School: Southside Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: Location, Location, Location. Welcome to an exceptional waterfront residence in the heart of Harbor Acres, where refined design meets the ultimate Florida lifestyle. This expansive 5,000+ square foot estate offers breathtaking sunset views over a private waterfront basin with direct access to Sarasota Bay—an idyllic setting for both everyday living and elegant entertaining. A private waterfront retreat, this five-bedroom, five full and two half bath home is thoughtfully designed to maximize comfort and flexibility. Enjoy a heated in-ground pool and spa, deep-water dock with boat lift, and ample space for a large vessel—perfect for boating enthusiasts seeking seamless access to Sarasota’s pristine waterways. The home features two primary suites, one on each level. The first-floor suite offers private garage access and is ideal for in-law accommodations, guests, or multigenerational living. Additional bedrooms can easily adapt to home offices, a fitness studio, or creative spaces to suit modern lifestyles. Multiple electric fireplaces enhance the ambiance in the primary suites, living room, and family room. An interior elevator provides effortless access between floors. The gourmet kitchen is designed for entertaining, showcasing granite and quartz countertops, a wet bar, a wine cooler, and a generous breakfast bar that opens seamlessly to the family room. The outdoor living spaces feature covered lanais on both levels overlooking the pool and bay, surrounded by tropical landscaping. A covered outdoor dining area includes a summer sink and dedicated pool bath, creating an ideal setting for entertaining or relaxing in total privacy. Move-in ready. This meticulously maintained home offers peace of mind and modern efficiency. Three new AC and HVAC systems (2024), two new gas water heaters, a variable-speed Jandy pool pump, new seawall cap, 22KW Generac generator, over $50,000 in recent upgrades. Prime Location, ideally located to Southside Village, residents enjoy easy access to acclaimed dining, boutique shopping, and Morton’s Gourmet Market. Hospitals, medical offices, banks, and essential services are all conveniently nearby—delivering both luxury and everyday convenience. This remarkable residence offers an unparalleled combination of waterfront luxury, thoughtful design, and walkable convenience. A rare opportunity to experience the best of Sarasota living.
Listing is courtesy of: HOUWZER INC (267-765-2080)
Listing Agent: Daniel Robinson (407-907-5501)
4439 WESTWOOD LN, SARASOTA, FL 34231
$2,995,000202 Days on yellowkey MLS ID: A4664741
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3777 Built: 1991Monthly Fee: $25 Tax: $20,186 (2024)Community: Oyster Bay EstatesSpa: YesSingle Family
Taxes:$20,186
Elementary School: Phillippi Shores Elementary
High School: Riverview High
Tax Year: 2024
Remarks: **BRILLIANTLY UPDATED and METICULOUSLY MAINTAINED ESTATE in OYSTER BAY, a Coveted, West of Trail Neighborhood** Situated on a large CORNER LOT, this 4-BED, 3 FULL and 1 HALF BATH residence is being Sold FURNISHED and offers desired privacy and extensive updates. Attention to detail is evident throughout this warm contemporary home featuring an open floorplan and unobstructed views of the Courtyard, Pool & Spa and Garden. For the culinary enthusiast, the impressive Kitchen boasts premium brand appliances including Subzero, Miele and Wolf. Enjoy the warmth of the wood-burning fireplace in the adjacent family room. Flexible Owner’s Suite with either Second or First-Floor possibilities. The second-story primary suite features a balcony overlooking the courtyard and pool, Multiple Walk-In Closets, beautifully update primary bath with dual vanities, custom-tiled shower, soaking tub, etc. In addition to the two guest bedrooms on the first floor, an additional room can also function as a spacious primary bedroom suite with an adjacent, updated Full Bath. NEW HVAC, WASHER & DRYER; WHOLE HOME GENERATOR (2021); NEWER ROOF (2017); HURRICANE IMPACT WINDOWS/DOORS (2018), ETC. Excellent location with easy access to lifestyle amenities — just a half mile to The Field Club… and in close proximity to Southside Village, Sarasota Memorial Hospital, Shopping Centers and Area Beaches including #1 Rated Siesta Key Beach. **Please Enjoy Viewing the 3D Virtual Tour and Aerial Video**
Listing is courtesy of: GENEROUS PROPERTY (941-275-9399)
Listing Agent: Mark Lyda (941-586-2670)
424 BOWDOIN CIR, SARASOTA, FL 34236
$14,750,000400 Days on yellowkey MLS ID: A4646393
1 Days Off yellowkey (back on 4/14/2026)
Bed: 5 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 5882 Built: 2023Monthly Fee: $25 Tax: $131,499 (2024)Community: Lido ShoresSpa: YesSingle Family
Taxes:$131,499
Middle School: Booker Middle
Remarks: Under contract-accepting backup offers. Set against Sarasota’s coveted bayfront in Lido Shores, this extraordinary waterfront estate captures sweeping views of Sarasota Bay, the downtown skyline, Ringling Bridge, and City Island, offering an unparalleled luxury lifestyle with effortless access to boating, beaches, and downtown Sarasota. More than a residence, this is a statement property—an iconic example of West Indies–inspired architecture executed with exceptional craftsmanship and modern sophistication. A private gated entry introduces a home where over $1 million in enhancements and more than 2,000 hours of custom design are evident throughout. Advanced smart home automation allows seamless global control, blending innovation with refined living. The custom front door opens to a dramatic foyer and a great room defined by a coffered ceiling, media wall, linear fireplace, and expansive bay views. The dining space features a quartz-topped bar with wine storage and flows into a chef’s kitchen appointed with Thermador appliances, a large floating island with quartz waterfall edges, and a walk-in pantry with an additional Bosch refrigerator. The primary suite is a tranquil sanctuary with floor-to-ceiling glass, sliders, and breathtaking water views. Two custom walk-in closets complement a spa-inspired bath featuring floating vanities, a soaking tub, a custom multi-head shower, and sliders leading to a private Zen garden with an outdoor shower. A sculptural staircase and glass-enclosed wine wall lead to an upper-level loft with a wet bar and waterfront terrace. A refined office with custom built-ins and four en-suite guest bedrooms, each with custom closets, projector screens, and private balconies, ensure comfort and privacy throughout. Outdoors, the estate transforms into a resort-style waterfront retreat. An infinity-edge pool with sun shelf, in-pool table, and cascading spa anchors the setting, surrounded by multiple seating areas, a firepit, and an outdoor shower. The fully equipped outdoor kitchen—featuring a smoker, grill, wok, and side burner—makes alfresco entertaining effortless, while a spiral staircase leads to an upper terrace with panoramic views. The newer deepwater dock is designed for serious boating, offering a 20,000-pound boat lift, jet ski lift, water and power, ambient lighting, and a dedicated fishing area. With direct access to Sarasota Bay just steps from the backyard, this property delivers exceptional boating and waterfront living. Additional features include a three-car garage, two laundry rooms, an elevator, a garage drop zone, and a hidden utility closet. The home is fully integrated with Control4 automation, security cameras, a 48-kilowatt generator, 20-kilowatt battery backup, high-end audio-visual systems, automated shades, circadian lighting, outdoor theater, app-controlled pool and irrigation, Wi-Fi-enabled appliances, EV charger prewiring, Starlink backup internet, motion-activated lighting, and voice control via Josh AI. Lido Shores is one of Sarasota’s most sought-after and architecturally significant waterfront communities, offering residents exclusive access to the north end of Lido Beach and close proximity to St. Armands Circle, Longboat Key, City Island, and downtown Sarasota. This remarkable bayfront estate is an architectural triumph, designed for sophisticated entertaining, advanced living, and extraordinary waterfront luxury.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Joel Schemmel (941-587-4894)
1347 HARBOR DR, SARASOTA, FL 34239
$4,300,00099 Days on yellowkey MLS ID: A4679697
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 4069 Built: 2014Monthly Fee: $13 Tax: $57,247 (2025)Community: Harbor AcresSpa: YesSingle Family
Taxes:$57,247
Remarks: Exceptional Harbor Acres modern residence offering 5 bedrooms, including a sunroom converted by the owners into a true 5th bedroom (closet and A/C). Warm contemporary design with seamless indoor-outdoor living. Located in Harbor Acres, one of Sarasota’s most coveted neighborhoods, this exceptional modern residence delivers a rare blend of warm contemporary design, luxury finishes, and seamless indoor-outdoor living. Perfectly scaled for the neighborhood, the open floor plan is flooded with natural light and effortlessly blurs the line between inside and out. The great room features 8-ft pocketing sliders opening to the covered lanai, anchored by a gas fireplace with illuminated floating shelves. The chef’s kitchen is a showpiece with top-of-the-line Miele appliances, solid wood cabinetry, an expansive quartz island, LED lighting, and a butler’s pantry for effortless entertaining. A separate dining room with picturesque windows offers an inviting setting for intimate gatherings, while the adjoining family room provides a relaxed space to unwind. The first-floor primary suite is a serene retreat with walls of windows overlooking lush tropical foliage and a spa-inspired bath featuring a soaking tub and glass shower. A dedicated office/flex room is conveniently located on the main level. Owners thoughtfully converted the sunroom into a 5th bedroom, offering added flexibility for guests or multigenerational living. Sleek open-riser stairs lead upstairs to two en-suite bedrooms providing privacy and comfort.
Listing is courtesy of: MICHAELA DAMM & PARTNERS (941-726-1808)
Listing Agent: Miska Damm (941-726-1808)
8008 MIDNIGHT PASS RD, SARASOTA, FL 34242
$3,750,000166 Days on yellowkey MLS ID: A4672889
Bed: 5 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 4190 Built: 2015 Tax: $25,117 (2024)Community: Mira Mar SubSpa: YesSingle Family
Taxes:$25,117
Elementary School: None
High School: None
Middle School: None
Remarks: Welcome to the side of Siesta Key most visitors never discover — and many locals refuse to leave. Located on the peaceful southern stretch of Midnight Pass Road, 8008 Midnight Pass sits far enough from the congestion of the Village and Beach Road traffic, yet only minutes from Crescent Beach and waterfront dining. Here, mornings start with bike rides under a canopy of palms, neighbors walk dogs along quiet streets, and evenings end with sunsets reflecting across Heron Lagoon. This is the residential, laid-back Siesta Key lifestyle buyers search for but rarely find available. Behind a newly installed private gate, fresh coastal landscaping and a new perimeter wall create a true sense of arrival and privacy. The 2015-built waterfront home has been extensively improved, offering the feel of a newer construction property without the wait, cost, or uncertainty of building on the island. Inside, the home has been refreshed with new flooring throughout, fresh interior paint, updated stair railings, and designer lighting. A full Sonos surround sound system, Brilliant smart switches, Philips Hue lighting, and an upgraded security system provide modern convenience, while spray-foam attic insulation improves comfort and efficiency year-round. The completely reimagined kitchen serves as the centerpiece of the home, featuring Viking appliances, quartzite countertops and backsplash, custom cabinetry with under-cabinet lighting, a custom hood, dedicated bar area, and Viking ice maker. The open living space flows directly to expansive sliders overlooking the calm waters of Heron Lagoon — a view that immediately explains why owners love this side of the island. A flexible den with a custom Murphy bed provides additional guest accommodations, and upstairs guest bedrooms have been enhanced with wainscoting and designer wallpaper. One guest bathroom has been fully remodeled and all bathrooms have been updated with new fixtures and lighting. Outdoor living is where the property truly shines. The lagoon-front setting offers a kayak and paddleboard launch from your backyard, an IPE dock for fishing or sunset watching, and a revitalized pool area with new equipment and LED lighting. A newly screened upper balcony lanai creates a peaceful retreat above the water, while the private basketball court adds a rare amenity not commonly found on Siesta Key. This is a home designed for those who want Siesta Key without the crowds — boating, biking, paddleboarding, and quiet evenings just minutes from the beach. 8008 Midnight Pass is not just a waterfront property; it’s an opportunity to experience the calmer, residential side of island living while still being close to everything that makes Siesta Key world-famous. Schedule your private showing and experience the difference in person.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Jeff Lauer (941-441-6555)
1504 S LODGE DR, SARASOTA, FL 34239
$6,990,00057 Days on yellowkey MLS ID: A4683855
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 5450 Built: 1965Monthly Fee: $25 Tax: $15,432 (2025)Community: Cherokee LodgeSpa: YesSingle Family
Taxes:$15,432
Remarks: First time available in 40 years! "Tween Bridges" is a rare bayfront property located in highly sought-after Cherokee Park, West of Trail. This 4-bedroom,3.5 bath residence offers unobstructed panoramic views of Sarasota Bay. The breathtaking sunsets and stunning vistas of Ringling Bridge, Siesta Key and downtown are truly mesmerizing. Boating enthusiasts will appreciate the brand-new dock with a 16,000lb lift and direct access to Sarasota's exceptional boating waters. Enjoy the home as it is or take advantage of this rare opportunity to build a custom waterfront estate on this magnificent property. Offered at $6,990,000, do not miss your chance to own one of Sarasota's finest waterfront locations. "Tween Bridges" is named for its location between The Ringling Bridge and The Siesta Key north bridge.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Melody Davis (908-202-4085)
7872 MAINSAIL LN, SARASOTA, FL 34240
$1,495,00036 Days on yellowkey MLS ID: A4687553
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3857 Built: 2022Monthly Fee: $500 Tax: $14,857 (2025)Community: Shoreview/Lakewood Ranch WaterSpa: NoSingle Family
Taxes:$14,857
Elementary School: Tatum Ridge Elementary
High School: Booker High
Middle School: McIntosh Middle
Remarks: Nestled in the sought-after community of Lakewood Ranch Waterside, this exceptional two-story home offers a harmonious blend of comfort and functionality in a picturesque setting. The main floor features a thoughtfully designed great room floor plan with volume ceilings showcasing custom coffered details, along with a private office ideal for working from home. The kitchen is a centerpiece of style and efficiency, boasting a large center island with seating, quartz countertops, stainless steel appliances, a gas cooktop, and a spacious walk-in pantry. The primary suite is a private retreat, complete with a walk-in shower, private water closet, and an expansive custom-organized dressing room. Two additional bedrooms and bathrooms on the main floor provide ample space for family or guests. Upstairs, a generous bonus room, along with a fourth bedroom and full bath, creates an ideal space for visitors. Enjoy a private pool and outdoor kitchen, perfectly positioned to take in serene lake views and a rare backdrop of a prestigious polo farm, where the sight of grazing horses enhances the setting. Shoreview residents enjoy a wide array of amenities, including a fitness center, resort-style pool, tennis and pickleball courts, and more. Located just minutes to Waterside Place, with convenient access to Lakewood Main Street, University Town Center, downtown Sarasota, I-75, beaches, top-rated schools, and medical facilities.
Listing is courtesy of: COLDWELL BANKER REALTY (941-907-1033)
Listing Agent: Katina Shanahan (941-702-0437)
3548 FOUNDERS CLUB DR, SARASOTA, FL 34240
$2,395,000287 Days on yellowkey MLS ID: A4658917
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 5426 Built: 2006Monthly Fee: $499 Tax: $10,982 (2024)Community: Founders ClubSpa: YesSingle Family
Taxes:$10,982
Remarks: This is the one * WELCOME TO THE FOUNDERS CLUB, ONE OF THE MOST COVETED COUNTRY CLUB COMMUNITIES IN SARASOTA * This Quality Built Lee Wetherington Executive Home features a VERY PRIVATE SETTING ON OVER 1/2 ACRE * PANORAMIC VIEWS OF A TRANQUIL LAKE IN YOUR BACKYARD WITH SERENE GREENBELT VIEWS FROM YOUR FRONT YARD - THIS IS A PREMIER LOCATION * RARELY AVAILABLE in this sought after neighborhood, this BEAUTIFUL HOME has been LOVINGLY RENOVATED * Step into the Grand Foyer and be amazed * Architectural details are at every turn * The current homeowners painstakingly oversaw every step of the NEW CHEF'S KITCHEN WITH A COASTAL CONTEMPORARY DESIGN BOASTING NEW Custom Wood Cabinets, NEW Quartz Countertops, a Waterfall Island, NATURAL GAS COOK-TOP and a Walk-in Pantry * The Kitchen is open to the SPACIOUS Family Room AND an expansive Glass-enclosed A/C Cabana-style Room with three walls of glass sliders (open the doors in the winter time!), screen windows, a natural gas fireplace, plus a wet bar - this is the perfect space for relaxing, entertaining, and it can even be used as a playroom * This FAMILY ESTATE is remarkable with 5,426+/- A/C SQFT * 4 Bedrooms & 4.5 Baths * Den/Office * Bonus Room * A Multi-use 15x13 Safe Room could be used as a Home Gym or Flex-space * Your Primary Suite features #2 Custom California style Walk-in Closet's and a NEW LOVINGLY RENOVATED Spa-style Bath with custom Cabinets, NEW Garden Tub, and a SPACIOUS Walk-in shower * This THOUGHTFULLY CURATED BATH is a TRUE OWNERS' RETREAT * Formal Living Room * Formal Dining Room * UPSTAIRS FEATURES A BONUS ROOM AND A SEPARATE GUEST BEDROOM + BATH with a Screened Lanai featuring Lake Views * Just a few of the additional features include: Volume ceilings * IMPACT GLASS WINDOWS + STORM SHUTTERS * SOLID CORE DOOR & CUSTOM WOOD TRIM * NEW Exterior Paint 2021 * NEW Interior Paint 2022 * Whole House Water Softener and Reverse Osmosis System * A 40-kilowatt OLYMPIAN NATURAL GAS WHOLE HOUSE GENERATOR * All of this wraps the PRIVATE HEATED POOL & SPA RECENTLY UPDATED with a NEW HEATER IN 2022 AND RESURFACING WAS DONE IN 2021 * The Founders Club is a beautiful low-density 24/7 guard-gated community with over 700 acres of wetlands and preserve and only 262 homes. The renowned Robert Trent Jones Jr. golf course offers members easy tee times and is one of the only walkable courses in the region. Har-Tru tennis courts & pickle ball courts and a picnic pavilion, and playground, basketball court, and fitness center are also on site. Residents enjoy easy access to the cultural venues of downtown Sarasota and attractions of Lakewood Ranch. Optional golf/social memberships. Members enjoy a 24/7 fitness facility, stately clubhouse, community events, and a restaurant with picturesque veranda. Come see this exceptional home and discover an extraordinary lifestyle. ONE LOOK & YOU'LL FALL IN LOVE *
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Glenn Brown (941-342-6464)
5023 ASHLEY PKWY, SARASOTA, FL 34241
$1,595,00047 Days on yellowkey MLS ID: A4686640
2 Days Off yellowkey (back on 4/13/2026)
Bed: 6 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 5154 Built: 1993Monthly Fee: $150 Tax: $9,623 (2025)Community: AshleySpa: YesSingle Family
Taxes:$9,623
Elementary School: Lakeview Elementary
Middle School: Sarasota Middle
Remarks: Under contract-accepting backup offers. This expansive 6BR, 5.5-bath estate offers 5,154 sq. ft. of luxurious living on nearly an acre, set back from the road with a circular paver driveway, lush landscaping, and a side-entry, climate-controlled three-car garage. The driveway provides ample parking for guests, and a pathway to the private entrance to the 2BR, 2-bath suite—ideal for multigenerational living. Step through one-of-a-kind custom art leaded glass doors, into a dramatic open entertaining space, with soaring ceilings that continue throughout the home. Sliding doors across the living room, connecting the indoors to the expansive 2,650sqft lanai and pool (45x17). The formal dining area is highlighted by a stunning Murano glass chandelier. The home’s sophisticated finishes reflect a thoughtful collaboration with interior designer Anne Folsom Smith. The kitchen and family room flow seamlessly together, with matching custom cabinetry. Premium stainless steel appliances, including a double oven, warming drawer, Miele dishwasher, and Sub-Zero refrigerator. second prep sink with instant hot water, conveniently located in the spacious stone-top center island alongside a second dishwasher. Custom designer cabinetry includes a large pantry and a built-in bar. Privately located on the far left wing of the home, the primary suite is a true retreat. The bedroom features built-in furnishings, expansive windows, elevated ceilings, and direct private access to the lanai and pool. A hallway with dual walk-in closets leads to a spa-inspired bathroom with oversized jetted tub, dual vanities, multi-head shower with bench, linen closet, private water closet, and a dedicated tankless hot water system. The secondary bedrooms are generously sized, including a flexible room currently set up as an office on the primary wing. A full bathroom provides convenient lanai and pool access. Enhancing the home’s versatility is a private two-bedroom, two-bath suite designed as a fully independent living space. Thoughtfully set apart yet seamlessly connected to the main residence by a light-filled vestibule off the family room, this exceptional retreat offers both privacy and ease. The vestibule features dual glass doors—one opening to a private rear entrance with its own patio, the other providing direct access to the screened pool—creating an ideal setting for guests or multigenerational living. Inside, a central living area unites the bedrooms and showcases custom built-ins alongside a well-appointed kitchenette with sink, disposal, generous counter space, and a full-size side-by-side refrigerator. A dedicated laundry and utility closet with washer and dryer, storage, and a separate hot water heater enhances convenience, while an independent HVAC system ensures year-round comfort with complete autonomy. The screened pool area offers a private, resort-style setting with expansive lanai. Sliding glass doors from the living, dining, kitchen, family rooms, and primary suite create seamless indoor-outdoor flow, ideal for both everyday living & large-scale entertaining. The layout easily accommodates sizable seated gatherings, with a natural transition between the home’s interior spaces and the lanai. Additional highlights include impact windows in the guest suite, whole-house water filtration and softening, central vacuum, four HVAC systems (including garage), irrigation system with new tank, electric pool heater, propane generator, three garbage disposals, two dishwashers, and a roof replaced in 2020.
Listing Agent: Scott Rickards, Pa (941-356-7040)
7796 ALISTER MACKENZIE DR, SARASOTA, FL 34240
$2,695,00075 Days on yellowkey MLS ID: A4682766
REDUCED by $90,000 (3.2%) on 04/12/2026
Bed: 5 Bath: 6.5 Gar: 4 Liv Area Sq Ft: 7639 Built: 1991Monthly Fee: $345 Tax: $18,579 (2025)Community: Laurel Oak Estates Sec 02Single Family
Taxes:$18,579
Remarks: With a level of scale and versatility rarely available in Laurel Oak Estates today, this residence is set on an oversized lakefront corner lot just under three-quarters of an acre, offering exceptional privacy, long water views, and a true legacy opportunity within the community. Designed for both gracious entertaining and everyday living, the home unfolds through expansive yet inviting spaces filled with natural light and framed by soaring ceilings and tranquil lake views. Multiple living and gathering areas create an effortless flow, allowing the home to feel equally comfortable hosting large celebrations or quiet evenings at home. At the heart of the residence, the chef’s kitchen anchors the main living areas with custom cabinetry, stone surfaces, a generous center island, and a built-in wine bar, ideal for connection, conversation, and entertaining. Architectural details such as eight-foot solid doors, crown molding, and thoughtfully scaled rooms add warmth and timeless character throughout. Five private en-suite bedrooms provide comfort and flexibility, including a spacious primary suite with spa-like bath and generous closet space. A separate lakefront guest residence offers exceptional versatility and privacy, featuring northern exposure, soaring ceilings, loft space, and a private balcony, ideal as an in-law suite, art studio, private office, or retreat. Outdoor living is calm and expansive. A screened pool and spa, newly updated with new tile and resurfacing, along with a paver lanai, outdoor shower, and courtyard with fountain create a peaceful setting for relaxation and entertaining, all overlooking the lake. The .6896 acre lot provides a rare sense of openness and privacy within the community. Additional features include a circular drive, multiple garages including a separate garage for the guest residence, multiple zoned air-conditioning systems, and a newer tile roof supporting comfort, efficiency, and ease of living. Experience the best of Laurel Oak, one of Sarasota’s most sought-after gated communities, featuring a 24-hour secure guard gate, beautifully maintained grounds, and a true sense of privacy and prestige. Residents also have the option to join the renowned Laurel Oak Country Club, home to two championship golf courses, tennis, dining, and an active social calendar that makes it easy to enjoy the very best of Florida club living. This is an estate designed not just to impress, but to be lived in, shared, and remembered.
Listing Agent: Jessica Stiegel (703-898-8465)
2519 SESAME ST, SARASOTA, FL 34231
$1,670,00077 Days on yellowkey MLS ID: A4682791
REDUCED by $25,000 (1.5%) on 04/12/2026
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3715 Built: 1975 Tax: $14,989 (2025)Community: Sesame Acres A RepSingle Family
Taxes:$14,989
Remarks: Motivated seller and welcomes serious offers! This 5-bedroom single-family home on just under an acre in the heart of Sarasota is a rare find. The residence has been beautifully updated featuring a stunning, newly renovated kitchen with modern finishes, quality cabinetry, and generous space for cooking, gathering, and entertaining. The thoughtfully designed layout flows seamlessly, offering both comfortable everyday living and an ideal setting for hosting family and friends. Set on an incredibly hard-to-find .93 acres, the property provides exceptional privacy and outdoor enjoyment. The fully fenced yard offers security and peace of mind, while the heated pool creates the perfect space for year-round relaxation and entertaining. Located within an excellent school district and close to everything Sarasota has to offer, this home delivers the perfect blend of space, style, privacy, and location.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Amber Lynch (941-556-9680)
1838 ALTA VISTA ST, SARASOTA, FL 34236
$3,495,000302 Days on yellowkey MLS ID: A4657794
Bed: 5 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 4452 Built: 2022 Tax: $17,607 (2024)Community: Avondale RepSpa: YesSingle Family
Taxes:$17,607
Remarks: Ensconced in the heart of the highly esteemed West-of-Trail Avondale neighborhood, this stunning 5-bedroom, 4.5-bath, 4400 square foot residence seamlessly blends timeless charm with modern luxury. Situated on a rare 14,750 sq ft oversized lot, the original 1952 home was extensively renovated and thoughtfully expanded in 2022, more than doubling its original square footage—all on a single level. Step inside to discover an open-concept layout designed for both comfort and entertaining, featuring a state-of-the-art kitchen with custom cabinetry, high-end appliances, a spacious eating area, and an impressive full butler’s pantry. The kitchen flows effortlessly into the elegant dining room and the great room, all bathed in natural light and finished with premium materials throughout. The home offers a separate formal living room and a versatile bonus room overlooking the pool—ideal for a home office, library, or sunlit sitting room. The owner's suite features sliding glass doors to access the pool, transom windows that filter in natural light, two walk-in closets, and top of the line finishes in the spa-like bath. The guest wing offers an over-sized bedroom, perfect for a home gym or private in-law suite, and provides privacy and flexibility for guests or multigenerational living. Every detail has been meticulously curated, from designer finishes to thoughtful storage solutions. Outside, enjoy lush landscaping, generous green space, and the perfect setting for outdoor entertaining. The lap pool and spa offer privacy and access to indoor-outdoor living spaces. All of this is located in the highly sought after Southside Elementary School district, and within walking distance to downtown Sarasota and Southside Village, placing dining, shopping, and cultural attractions just steps from your door.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Jennifer Linehan (941-266-7555)
5012 HIGEL AVE, SARASOTA, FL 34242
$2,249,000284 Days on yellowkey MLS ID: A4658844
REDUCED by $200,000 (8.2%) on 04/08/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3541 Built: 1959 Tax: $16,035 (2024)Community: Harmony SubSpa: NoSingle Family
Taxes:$16,035
Remarks: One or more photo(s) has been virtually staged. Discover this FULLY RENOVATED four-bedroom, three-bathroom sanctuary spanning 3,541 square feet, where luxury living meets WATERFRONT tranquility. Situated on almost a half acre lot, with rear views facing west for colorful sunsets, this meticulously crafted residence boasts a heated pool, a floating dock and long seawall inviting water enthusiasts to enjoy exploring the canals which lead out to the open waters of Sarasota Bay. The heart of this distinguished home features an expansive open-concept main living area, chef's kitchen and spacious dining space, thoughtfully designed to accommodate family and guests while offering sweeping views of the sparkling pool and canal. The seamless flow of the layout and blending of the outdoor and indoor space creates an entertainer's paradise, perfect for culinary adventures and memorable gatherings. Retreat to the luxurious primary bedroom, where panoramic canal vistas provide a serene backdrop for morning coffee or evening reflection. Unwind in the spa-like bathroom featuring a soaking tub, walk-in shower, dual vanities and frosted sliding glass doors to the outdoor shower. The SPLIT FLOORPLAN ensures ease and privacy for all. Bedroom 2 features an en-suite bathroom and long water views! Bedroom 3 has double doors and can be utilized as a den or office space if desired. Bedroom 4 has a private entrance with sliding glass doors overlooking the sunny front courtyard. This thoughtful layout offers many options for use of the generous space. The coral stone tiled pool and lanai area transforms into your personal oasis, where gentle breezes dance across the water's surface, creating an atmosphere of pure indulgence after sun-soaked beach days. The fully fenced yard, greenspace, winding walkways, outdoor shower, 2 car garage with extended driveway and parking space complete this comfortable retreat. The property's exceptional LOCATION places you moments (just .6mi) to the vibrant Siesta Village, where boutiques and acclaimed dining establishments await your discovery. (Just .7mi) to the nearest beach access! The main entrance to World-renowned Siesta Beach, celebrated for its powdery white sands and crystal-clear waters, beckons just over a mile away. This remarkable residence represents more than mere accommodation; it embodies a lifestyle where every detail has been carefully considered. From the quality construction evident throughout to the thoughtful integration of indoor and outdoor living spaces, this home promises years of comfort in one of Sarasota's most coveted waterfront communities.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Rachelle Tirey (941-301-9187)
7647 SANDERLING RD, SARASOTA, FL 34242
$3,300,00050 Days on yellowkey MLS ID: TB8486392
REDUCED by $699,000 (17.5%) on 04/12/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 4006 Built: 1961Monthly Fee: $450 Tax: $23,004 (2025)Community: Sanderling ClubSpa: YesSingle Family
Taxes:$23,004
Remarks: The Ness House | A rare architectural opportunity in Sanderling A rare opportunity has emerged on Siesta Key. The Ness House, masterfully designed by renowned architect Tim Seibert, is a timeless expression of the Sarasota School of Architecture where clean lines, natural light, and a seamless connection to the outdoors define every moment. Privately set within the gated enclave of Sanderling, this residence embodies understated luxury and architectural significance. Expansive walls of glass blur the line between inside and out, inviting sunlight to fill the interiors while framing tranquil natural surroundings. The thoughtful design captures coastal breezes and creates a living experience that is both serene and effortlessly curated. Just moments away, the powder-soft quartz sands and turquoise waters of Siesta Key entry point of the most celebrated beach experiences in the world perfect for morning walks, sunset evenings, and the kind of lifestyle most only dream of. Now compellingly re-positioned, the offering presents exceptional value for a home of this pedigree, location, and design significance. Opportunities like this—where architecture, privacy, and proximity to the beach align are increasingly rare. For the buyer who understands design and recognizes true value, this is the moment to step in. Private showings are now available experience The Ness House firsthand.
Listing is courtesy of: PREMIER SOTHEBY'S INTL REALTY (727-595-1604)
Listing Agent: Janet Moore (813-892-0998)
44 ROCKWELL LN, SARASOTA, FL 34242
$6,800,00058 Days on yellowkey MLS ID: A4685222
Bed: 6 Bath: 6.5 Gar: 9 Liv Area Sq Ft: 5400 Built: 2025Monthly Fee: $125 Tax: $12,651 (2024)Community: Sandy HookSpa: YesSingle Family
Taxes:$12,651
Remarks: Pre-Construction. To be built. Call for all details and plans. All info coming soon!
Listing is courtesy of: JOSEPH RUSSO, LICENSED R.E. BROKER (941-928-1613)
Listing Agent: Joseph Russo (941-928-1613)
1726 WALDEMERE ST, SARASOTA, FL 34239
$5,750,00058 Days on yellowkey MLS ID: A4685190
REDUCED by $25,000 (0.4%) on 04/12/2026
Bed: 5 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 5250 Built: 2026 Tax: $5,943 (2026)Community: N/ASpa: YesSingle Family
Taxes:$5,943
Tax Year: 2026
Remarks: Pre-Construction. To be built. Buyer may customize plan, size, price and finishes. Call agent for all details. All info coming soon!!!
1640 WALDEMERE ST, SARASOTA, FL 34239
$6,400,00058 Days on yellowkey MLS ID: A4685215
INCREASED by $25,000 (0.4%) on 04/12/2026
Bed: 5 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 5270 Built: 2026 Tax: $8,031 (2026)Community: Lewis Combs SubSpa: YesSingle Family
Taxes:$8,031
Remarks: Coming soon! Completion 5/11/26. Modern Luxury Villa | 1640 Waldemere St Experience the pinnacle of Gulf Coast luxury in this stunning Miami-style modern villa, perfectly situated West of Trail in one of Sarasota’s most coveted neighborhoods. This architectural marvel blends high-end technology with effortless coastal living, offering a sophisticated sanctuary just minutes from the vibrant pulse of Downtown Sarasota and the world-renowned sands of Siesta Key and Lido Beach. The Residence Designed for the connoisseur of fine living, this home boasts a sleek, minimalist aesthetic defined by clean lines and expansive glass. Elevated Living: Move effortlessly between floors with your private elevator. The Great Indoors/Outdoors: Massive automated glass doors disappear to create a seamless transition to the resort-style pool deck, perfect for year-round entertaining. Privacy at Your Fingertips: Equipped with cutting-edge Smart Glass technology, windows transition from transparent to opaque instantly for ultimate privacy. Space for Everything: Featuring 5 spacious bedrooms, a dedicated executive office, and a private home gym, there is no better lifestyle or utility. Tech-Forward Luxury This is a fully realized Smart Home, designed for total control and ambiance: Integrated Smart Home System: Control lighting, climate, and security from your device. Whole-Home Audio: An immersive sound system flows through every room and out to the pool deck. Modern Finishes: Premium materials and high-end fixtures throughout reflect a commitment to quality and contemporary style. The Location Located West of 41, 1640 Waldemere St places you in the heart of Sarasota’s most desirable "West of Trail" district. You are seconds away from: Sarasota Memorial Hospital and the medical district. Downtown Sarasota’s fine dining, opera, and boutiques. St. Armands Circle and local beautiful sand beaches. Live the Future of Luxury. This villa isn't just a home; it’s a statement. Call for all details…
3597 FOUNDERS CLUB DR, SARASOTA, FL 34240
$1,950,000151 Days on yellowkey MLS ID: A4673915
Bed: 4 Bath: 3.5 Gar: 4 Liv Area Sq Ft: 3957 Built: 2006Monthly Fee: $467 Tax: $17,901 (2024)Community: Founders ClubSpa: YesSingle Family
Taxes:$17,901
Remarks: A True Gem in The Founders Club Elegance, Comfort, and An Outstanding Location Welcome to 3597 Founders Club Drive, an exquisite residence nestled within Sarasota’s premier gated golf community, The Founders Club. Built in 2006, this residence combines quality construction with modern amenities and is walking distance to the club house. The property sits on a 0.47 acre lot, offering both space and intimacy within a prestigious community known for its Robert Trent Jones jr. golf course, clubhouse, and social activities. Spanning 3,957 square feet of living space, this home features four spacious bedrooms, three full baths, and one half bath, thoughtfully designed with a split floor plan to maximize privacy and comfort. The grand foyer opens into formal living and dining areas, while the family room has pocket sliders which open onto the lanai. High ceilings, crown molding, and expansive windows create a light filled ambiance throughout the house. The gourmet kitchen is a chef’s delight, boasting a large center island, breakfast bar, walk in pantry, and custom cabinetry. Stainless steel appliances and ample counter space make entertaining effortless. Adjacent to the kitchen, the family room offers casual elegance with views of the pool and lanai. A separate breakfast nook provides the perfect spot for morning coffee in the sheltered lanai overlooking the 18th fairway. The primary suite is a private retreat, complete with dual vanities, a walk in shower and separate tub. Generous his and her closet space and direct access to the lanai enhance the sense of luxury. Additional bedrooms are well appointed, ideal for family or guests, while a bonus room and dedicated office/den provide flexibility for work or leisure. Outdoor living is at the heart of this home. The expansive screened lanai showcases a sparkling pool and spa, surrounded by ample deck space for lounging or dining al fresco. Mature landscaping ensures privacy, while the backdrop of The Founders Club’s natural beauty creates a tranquil oasis. With his and her two car garages, there is abundant space for vehicles, golf carts, and storage. Living at The Founders Club means enjoying an exclusive lifestyle. Residents benefit from a limited membership golf club, (for which a membership is available for transfer), little traffic, and a vibrant social calendar. Located east of I 75, the community provides convenient access to downtown Sarasota, world class beaches, cultural venues, and fine dining. This home is more than a residence—it is a statement of elegance and comfort. Whether hosting gatherings, enjoying quiet evenings by the pool, or taking advantage of the community’s amenities, 3597 Founders Club Drive offers the perfect blend of sophistication and Florida living. Don’t miss the opportunity to make this exceptional property your own. Schedule a private tour today and experience the unmatched charm of The Founders Club.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-907-9595)
Listing Agent: Richard Hearn (941-313-1591)
3129 FOUNDERS CLUB DR, SARASOTA, FL 34240
$2,895,00027 Days on yellowkey MLS ID: A4689202
Bed: 3 Bath: 4.5 Gar: 4 Liv Area Sq Ft: 5742 Built: 2008Monthly Fee: $655 Tax: $32,512 (2025)Community: Founders ClubSpa: YesSingle Family
Taxes:$32,512
Remarks: Set along the 11th green within the private, guard-gated Founders Club, this custom residence by John Cannon Homes captures sweeping golf course, lake, and preserve views across a beautifully positioned .69-acre homesite. Spanning over 5,700 square feet, the two-level design is both elegant and highly livable, with soaring ceilings, detailed millwork, and a natural flow that supports both everyday comfort and large-scale entertaining. A gracious foyer introduces formal living and dining spaces, while the heart of the home opens to a spacious family room and chef’s kitchen featuring premium appliances, a Wolf gas cooktop, oversized island, walk-in pantry, and a sunlit breakfast area framed by aquarium glass overlooking the water and fairways. Walls of French doors create a seamless transition to the expansive screened lanai, where the pool and spa, outdoor kitchen, and covered living areas are surrounded by tranquil views—an ideal setting for quiet mornings or evening gatherings. The primary suite is thoughtfully designed as a private retreat, complete with a sitting area, custom office, dual boutique-style closets, and a spa-inspired bath with hydrotherapy tub, oversized shower, and dual water closets. Two additional guest suites are positioned in a separate wing for privacy. Upstairs, accessible by elevator or stairs, a generous bonus room with wet bar, fireplace, and full bath opens to a terrace with long, open views across the course—easily adaptable as a fourth bedroom or private guest quarters. Additional highlights include a wine cellar, butler’s pantry, travertine and hickory flooring, coffered ceilings, impact-rated openings, and a four-car garage. The Founders Club spans 700 acres of preserved natural beauty, offering a refined yet relaxed lifestyle with optional membership to its Robert Trent Jones Jr.–designed championship golf course, clubhouse, dining, fitness center, and tennis and pickleball amenities. A home defined by scale, setting, and architectural integrity—positioned within one of Sarasota’s most established private communities.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Judie Berger (941-928-3424)
2314 PROSPECT ST, SARASOTA, FL 34239
$2,275,00061 Days on yellowkey MLS ID: A4684572
Bed: 5 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 3651 Built: 2024 Tax: $18,837 (2025)Community: Loma Linda ParkSpa: YesSingle Family
Taxes:$18,837
Elementary School: Alta Vista Elementary
Remarks: A statement of modern elegance in the heart of Sarasota, this exceptional Arlington Park residence delivers refined luxury, architectural presence, and elevated design at every turn. Offering 5 bedrooms, 5.5 bathrooms, and 3,651 square feet under air, this custom-built home was thoughtfully designed for those who appreciate both sophisticated entertaining and comfortable everyday living. From the moment you enter, soaring 12-foot ceilings and a dramatic staircase create an unforgettable first impression. The main living spaces are open, expansive, and filled with natural light. A designer kitchen anchors the home, showcasing solid wood cabinetry, quartz countertops, an oversized waterfall island, and premium Thermador appliances which are perfectly suited for culinary enthusiasts and elegant gatherings alike. A custom built-in feature wall enhances the living area with both style and function. Sliders seamlessly connect indoor and outdoor spaces, creating effortless Florida living. A private first-floor office offers a quiet retreat for work or study. Upstairs, 10-foot ceilings and rich hardwood flooring continue the home’s elevated aesthetic. The owner’s suite is a true sanctuary, complete with a private balcony overlooking the backyard, custom vanity, a soaking tub, and an oversized walk-in shower finished with striking designer tile. Each additional bedroom features its own en-suite bath and walk-in closet, ensuring comfort and privacy for family and guests. A spacious second-floor den provides flexible space for a media room, lounge, or game area. The outdoor setting rivals a private resort. The saltwater pool with waterfall and sun shelf is complemented by a spa, outdoor shower, and dedicated pool bath. A modern aluminum pergola adds architectural interest and shaded relaxation, while the lanai invites seamless entertaining year-round. No detail was overlooked: impact-rated windows and doors, epoxy-finished 2.5-car garage, irrigation system, integrated indoor/outdoor speakers, pre-wiring for security cameras, and dual A/C systems for optimal efficiency. Located in highly desirable Arlington Park, this home places you minutes from downtown Sarasota, Sarasota Memorial Hospital, and the area’s renowned dining and cultural destinations. World-class beaches including Siesta Key and Lido Key are just a short distance away. This is more than a home...it is a lifestyle defined by quality, design, and distinction. All information provided by the sellers is deemed reliable but is not guaranteed. Buyers are encouraged to verify all information independently.
Listing Agent: Lisa Kroshus (941-303-3429)
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