Location: Sarasota
Do Not Show Listings
700 TROPICAL CIR, SARASOTA, FL 34242
$1,699,00049 Days on yellowkey MLS ID: A4684757
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 2341 Built: 1977Monthly Fee: $54 Tax: $5,315 (2025)Community: Siesta BeachSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,315
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Welcome to your private waterfront oasis, a meticulously renovated home set on a super private .41-acre lot defined by lush, mature greenery in one of Siesta Key’s most sought-after neighborhoods. The residence sits at a 9 foot elevation!! The interior features two primary bedroom suites, including a main retreat with a custom-built in closet. The open-concept layout has wide-plank light oak flooring and a kitchen with Italian cabinetry, waterfall quartz countertops, and a custom floor-to-ceiling built in cabinet pantry. Extensive structural and functional UPGRADES include a NEW ROOF, NEW STORM RATED WINDOWS AND SLIDERS, NEW DRAIN PIPES, and NEW PVC water lines. Transition through impact-rated glass sliders to a sun-drenched lanai and a new paver deck featuring a pool with all-new pool equipment. The backyard is a secluded tropical retreat bordered by a thick mangrove canopy for total privacy, offering direct water access for kayaking. Beyond the property, you are just minutes from the world-famous white sands of Siesta Key Beach, the vibrant dining and boutique shopping of Siesta Key Village, and a short drive to the cultural heart of Downtown Sarasota. From the designer finishes to the total structural renewal, this home offers security and luxury in a premier, verdant location. Call to set up a showing ~
Listing is courtesy of: CHIC PROPERTIES II LLC (941-302-0134)
Listing Agent: Ilona Davidovich (941-302-0134)
103 FILLMORE DR, SARASOTA, FL 34236
$2,499,00036 Days on yellowkey MLS ID: A4686381
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2908 Built: 1951 Tax: $20,246 (2025)Community: Saint Armands Div John Ringling EstatesSingle Family
Taxes:$20,246
Remarks: Welcome to 103 Fillmore Drive, a beautifully renovated 4-bedroom (or 3 bedroom plus den/office), 3-bath pool home located in the heart of world-famous St. Armands Circle. Just a few blocks from the white sands of Lido Beach, this exceptional property offers the perfect opportunity as a primary residence, vacation home, or income-producing investment. The home has been completely renovated and features an open, inviting layout designed for comfortable Florida living. The living area includes a cozy fireplace and flows seamlessly to the outdoor entertaining spaces. Step outside to your private backyard oasis with a sparkling pool, tropical landscaping, bar with grill,and a firepit lounge area—perfect for relaxing or entertaining under the Florida sunshine. Major improvements include a new roof installed in 2025, kitchen and baths updated and whole home beautifully remodeled. Located just moments from the renowned restaurants, boutiques, and vibrant atmosphere of St. Armands Circle and minutes to downtown Sarasota, the home offers an unbeatable island lifestyle. With estimated rental income potential of approximately $100,000 annually, this property presents a rare opportunity in one of Sarasota’s most desirable coastal communities.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Tom Cail, Pa (941-780-2245)
3360 HIGEL AVE, SARASOTA, FL 34242
$1,549,00069 Days on yellowkey MLS ID: A4682008
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2006 Built: 1960 Tax: $13,348 (2025)Community: Siesta Rev OfSingle Family
Taxes:$13,348
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Middle School: Brookside Middle
Remarks: Welcome to the home you've been waiting for! Your opportunity to own a fully updated island retreat pool home on world-famous Siesta Key. Imagine waking up minutes from powdery white quartz sand beaches, spending your afternoons poolside under the Florida sun, and ending your evenings with sunset walks along the water. This four-bedroom, three-bathroom home offers the flexibility, comfort, and lifestyle today’s buyers are looking for — whether as your primary residence, second home, or income-producing weekly rental. Inside, the home has been completely updated and thoughtfully designed for modern coastal living. With three separate living room areas, there is space for everyone to gather, relax, and spread out comfortably. Whether hosting friends, accommodating extended family, or welcoming vacation guests, the multiple living spaces provide both connection and privacy — a rare and valuable feature in Siesta Key homes. Natural light fills the interiors, creating a bright and inviting atmosphere that reflects the relaxed elegance of island life. Step outside to your new private pool and expansive outdoor living space designed for year-round enjoyment. Lounge poolside with morning coffee, host dinners, or unwind after a day at the beach. The seamless indoor-outdoor flow captures what Siesta Key living is all about. One of the most compelling features of this property is the one-week minimum rental allowance — a highly sought-after benefit on Siesta Key. Weekly rental flexibility allows you to generate strong short-term rental income while still enjoying personal time in your island home. With Siesta Key consistently ranked among the top beaches in the world, demand for updated weekly rental properties remains strong throughout the year. Residents of this neighborhood also enjoy private access to a beach area on the Pass — a peaceful waterfront setting perfect for sunset strolls, kayaking, paddle boarding, fishing, or simply relaxing away from the main beach crowds. Located just minutes from Siesta Key Village, you are close to dining, boutique shopping, live music, and vibrant island culture. Downtown Sarasota, marinas, golf courses, and Sarasota-Bradenton International Airport are all within easy reach. Whether you are searching for your own Siesta Key escape, a turnkey beach home with a pool, or a high-performing weekly rental investment in Sarasota, 3360 Higel Avenue offers the rare combination of lifestyle, flexibility, and location in one of Florida’s most coveted coastal communities.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Natalie Gutwein (941-993-2660)
2616 WATERFRONT CIR, SARASOTA, FL 34240
$1,274,00024 Days on yellowkey MLS ID: A4687928
Bed: 5 Bath: 4.5 Liv Area Sq Ft: 3416 Built: 2026Monthly Fee: $353 Tax: $2,479 (2025)Community: Monterey At Lakewood RanchSingle Family
Taxes:$2,479
Elementary School: Tatum Ridge Elementary
High School: Booker High
Middle School: McIntosh Middle
Remarks: Under Construction. The Bearadise’s expansive open floor plan offers an exceptional blend of spaces for gathering and quiet retreats. An elegant foyer flows past a secondary bedroom with a walk-in closet and a shared full hall bath. The impressive great room is enhanced by a tray ceiling and access to the expansive covered lanai—perfect for entertaining or relaxing. Overlooking the casual dining area and great room, a well-equipped kitchen features a large center island with breakfast bar, ample counter and cabinet space, and a walk-in pantry. Highlighting the primary bedroom suite is a tray ceiling, a generous walk-in closet, and a luxurious primary bath showcasing a dual-sink vanity, a luxe shower, linen storage, and a private water closet. Adjacent to a versatile loft on the second floor are three secondary bedrooms featuring walk-in closets. Two of the bedrooms share a full hall bath, and one features a private bath. Future water views and a pool, spa, and convenient cabana bath complete this home. The kitchen layout is reimagined with an extended center island and additional storage. Modern open rail detail at the loft creates an airy second-level connection. Your upgraded primary bath features a luxe shower, freestanding tub, and dual-sink vanity. Schedule a visit today!
Listing is courtesy of: TAMPA TBI REALTY LLC (941-279-4055)
Listing Agent: Jordan Kosobucki (941-313-7373)
8534 HERON LAGOON CIR, SARASOTA, FL 34242
$1,299,00026 Days on yellowkey MLS ID: A4687653
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1153 Built: 1949Monthly Fee: $75 Tax: $5,695 (2025)Community: Heron Lagoon LodgesSingle Family
Taxes:$5,695
Remarks: A 2-minute walk across your private footbridge to secluded beach access, this 12,684-square-foot property in Heron Lagoon presents a rare opportunity to own in one of Siesta Key’s most intimate waterfront communities. The existing residence offers the potential to renovate or personalize, all while enjoying a tranquil lagoon setting. The property features a resort-style pool already in place which will need rehabbed, creating a strong foundation for an upgraded outdoor living space. With thoughtful improvements, this home can be transformed into a private coastal retreat that embraces indoor-outdoor living. Set within an exclusive enclave of just 13 homes — while this is 1 of 6 located on the water — residents enjoy a quiet, low-HOA community with direct access to kayaking, paddleboarding, fishing, and birdwatching. Private bridge access leads to a short stroll to Siesta Key’s world-renowned quartz-crystal beaches. Conveniently located just minutes from Siesta Key Village’s shops and dining, this property offers a unique opportunity to create your own island getaway. 3D renderings are available upon request for those seeking design inspiration.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Karlenn Peluso (941-356-5345)
1264 18TH ST, SARASOTA, FL 34234
$745,00025 Days on yellowkey MLS ID: A4687775
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 1921 Built: 1947 Tax: $5,774 (2025)Community: EdgewaterSingle Family
Taxes:$5,774
Remarks: Discover a rare multifamily investment opportunity on the near north side of Sarasota, located in the heart of the highly sought-after Central Cocoanut Historic District. This unique offering includes two adjacent parcels, providing exceptional flexibility for investors, developers or someone interested in a large single-family home with room to expand. One parcel features a solid masonry three-bedroom, two-bathroom home complete with a one bed, one bath, 566 square foot in-law suite created from a garage conversion. The home is a split plan and two of the bedrooms are “en-suite”. All three bedrooms have exterior access. The kitchen is bright and updated and opens to the shared lanai and utility room. In addition to the “in law” suite there is an attached 220 square foot studio, offering creative or rental potential. The neighboring parcel is a vacant lot, also zoned for multifamily use—giving you the freedom to design and build to suit your vision. Together, the properties allow for up to five total units, making this an ideal opportunity to expand your rental portfolio or develop a custom income-producing property in a prime location. Situated in a vibrant, walkable neighborhood with bike lanes, you’ll enjoy easy access to downtown Sarasota, along with its renowned dining, shopping, arts, and cultural amenities. The Ringling College of Art and design is just a few blocks away and the adjacent North Trail Corridor is experiencing some of Sarasota’s most dynamic development. A short 10-minute drive over the Ringling bridge lands you in St. Armands Circle and the beaches of Lido and Longboat Key.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: David Jennings (941-650-7354)
2439 FEIFFER CIR, SARASOTA, FL 34235
$350,00075 Days on yellowkey MLS ID: A4681217
1 Days Off yellowkey (back on 2/9/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1745 Built: 1986Monthly Fee: $36 Tax: $4,661 (2025)Community: Kensington WoodsSingle Family
Taxes:$4,661
Elementary School: Gocio Elementary
Middle School: Booker Middle
Remarks: Under contract-accepting backup offers. Located in the established community of Kensington Woods in Sarasota, this 3-bedroom, 2-bath home presents a rare opportunity to create something truly special. With a well-designed floor plan, a two-car garage, and a private pool, the foundation is in place for a thoughtful renovation tailored to your vision. The home offers generous living spaces and a layout that lends itself well to modern updates, while the outdoor area provides the perfect starting point for a reimagined Florida lifestyle—ideal for relaxing, entertaining, or enhancing the existing pool retreat. Set in a desirable neighborhood known for its convenience and charm, this property is well-suited for buyers or investors looking to add value and personalize a home in a sought-after Sarasota location. With the right updates, this residence has the potential to shine and become a standout within Kensington Woods. An exciting opportunity for those who see the possibilities and appreciate the reward of transformation. Is this home your perfect match? Book a private showing today!
Listing is courtesy of: HOUSE MATCH (941-213-7028)
Listing Agent: Rachel Woodruff, Pa (941-705-8686)
5116 ADMIRAL PL, SARASOTA, FL 34231
$1,100,00088 Days on yellowkey MLS ID: A4678935
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 2243 Built: 1980 Tax: $6,124 (2025)Community: Phillippi ShoresSingle Family
Taxes:$6,124
Remarks: This luxury waterfront estate on Phillippi Creek is ideal for boaters, offering direct intercostal access, four bedrooms, and the largest square footage under $1.5M among current listings. Located on a peninsula, just minutes from Sarasota Bay and Siesta Key, the home features stunning water views, a peaceful cove, and beautiful sunsets. Recent renovations include a new roof, HVAC, electric, plumbing, hurricane-impact windows, and energy-efficient spray foam insulation. The bathrooms and chef’s kitchen have been meticulously updated with high-end fixtures including Kohler rain showerheads, handheld wands and body jets, Viking appliances and KitchenAid double wall ovens and wine fridge. The living room has extensive water views, a gas log fireplace and soaring cedar-beamed ceilings creating a dramatic yet warm architectural statement, while honed marble floors extend throughout. Two bedrooms have private entrances—perfect for guests or home office. The primary suite provides serene water views without leaving the comfort of your bed. Enjoy seamless indoor-outdoor living with multiple entrances to the screened lanai and deck. Outdoor enthusiasts will appreciate the private dock, with water and electric, providing quick access for boating, kayaking, and paddleboarding to the Bay and Siesta Key beach. Ideal for fishing and daily wildlife sightings, including manatees and abundant birdlife. Centrally located, minutes to downtown (3.7 miles), Siesta Key Beach (2.1 miles) and SRQ Airport (7.7 miles), this rare offering presents an outstanding luxury waterfront residence or high-end rental investment for boaters, beach goers, and nature lovers alike. Only 15 properties are available on this peninsula, making homes in this secure, HOA-free, close-knit community rare when listed. A truly unique Sarasota waterfront opportunity.
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Esther Farber (989-980-8231)
8340 SEA GLASS CT, SARASOTA, FL 34240
$1,960,00029 Days on yellowkey MLS ID: A4685558
Bed: 3 Bath: 3.5 Liv Area Sq Ft: 2841 Built: 2024Monthly Fee: $616 Tax: $15,478 (2025)Community: Wild Blue At WatersideSingle Family
Taxes:$15,478
Remarks: Welcome to this breathtaking, model-like residence in the sought-after community of Wild Blue in Waterside. Positioned on a premier lakefront and preserve homesite, this extraordinary property showcases serene views, and designer finishes reminiscent of the pages of Architectural Digest. With nearly $400,000 in post-closing upgrades and renovations, this home is one of a kind. A striking glass and iron front door sets the tone for the sophisticated interiors, where you’ll find exceptional craftsmanship throughout, featuring custom wood beams, shiplap accent walls, intricate millwork and thoughtfully designed ceilings. The heart of the home is the fully reimagined chef’s kitchen, outfitted with custom wood cabinetry, commercial-grade appliances, an expansive center island with breakfast bar and a concealed walk-in pantry with custom wood shelving. The kitchen flows seamlessly into the spacious great room and formal dining area, creating a setting for entertaining. The great room is highlighted by a stunning custom-built entertainment wall with wood shelving, cabinetry and integrated storage, while a wall of sliding glass doors opens to the outdoor living space. The lanai is an entertainer’s dream, complete with a stone fireplace, saltwater heated pool and spa, outdoor kitchen, stone pavers, and generous covered areas for dining and relaxation while the panoramic screen captures peaceful lake and wildlife views. The luxurious primary suite has undergone an extensive transformation, offering two walk-in closets, including a converted bedroom now serving as an impressive 13-by-11-foot custom closet with built-ins, drawers and a center island. The spa-inspired primary bath features a freestanding sculptural soaking tub, a large walk-in shower with dual shower heads, glass enclosure, tile detailing and niches, along with a dual-sink vanity. French doors provide direct access from the primary suite to the lanai. A private office with tray ceilings, floating shelving and pocket doors creates an ideal work-from-home environment. Two additional guest suites each offer en-suite baths and custom closet systems, ensuring comfort and convenience for visitors. The redesigned laundry room includes front-loading washer and dryer, along with built-in cabinetry for maximum functionality. Additional highlights include impact windows and doors, reverse osmosis and whole-home water filtration systems, porcelain tile flooring throughout, custom closet systems in every room. This exceptional three-bedroom, den and 3.5 bath property combines luxury, comfort and impeccable design in one of Waterside's desirable communities. Within the desirable enclave of Wild Blue at Waterside, this residence is complemented by an array of world-class amenities. The upcoming 25,000-square-foot resort-style clubhouse will feature private dining, a theater, fitness studio, golf simulator, workout classrooms, and indoor and outdoor dining options. Outdoors, enjoy a spectacular complex with a resort-style pool, lap pool, yoga lawn and premier putting course, curated by a dedicated lifestyle director who brings together neighbors with engaging social events. Already open, the Midway Sports Complex enhances the community experience with pickleball and tennis courts, basketball, a dog park, sports activity areas, a kayak launch and scenic lakefront viewing. Schedule your showing today!
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-907-9541)
Listing Agent: Charles Totonis (941-524-8299)
4811 79TH AVENUE PLZ E, SARASOTA, FL 34243
$435,00047 Days on yellowkey MLS ID: A4684777
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1701 Built: 1986Monthly Fee: $30 Tax: $3,023 (2025)Community: Country Oaks Sub Ph IiSingle Family
Taxes:$3,023
Remarks: Welcome to Country Oaks, a well established community in Lakewood Ranch! Close to the Palm Aire Golf & Country Club. LOW HOA at $90/Quarter with Community Pool! This well maintained 3/2 split block-built home has over $100,000 in upgrades, including: 2021 GAF Shingle ROOF with 3rd nail to reduce insurance costs. 50 year leak proof warranty and 25 years on the shingles-fully transferable. 2021 HVAC Split System with added insulation in attic, HURRICANE rated (150+) PGT Windows and Slider doors. Upgraded duct work with allergen and dual thermostats for each side of the home. 12 Year transferable warranty Rheem Hot Water heater with remote control. Absolute Aluminum gutters. Kitchen granite countertops with upgraded cabinets with soft close drawers. New irrigation system. Master bedroom has an attached den/office, walk-in closet and full bathroom with glass shower stall. Second and Third bathroom share a hallway renovated full bathroom with walk-in rain shower. Spacious outdoor paved patio for entertaining with a 12x12 Home Depot Wood Pergola. 10x10 Tuff Shed in backyard with 3 ft down anchored posts, fully fence yard, updated exterior outdoor lighting. Two car garage with storage, drop down step ladder access and laundry units. Great established community with mature landscaping and sought after location!
Listing Agent: Monica Desomma (202-427-4328)
1894 LOMA LINDA ST, SARASOTA, FL 34239
$2,500,00036 Days on yellowkey MLS ID: A4685717
Bed: 3 Bath: 3.5 Liv Area Sq Ft: 1867 Built: 1954 Tax: $11,627 (2025)Community: Floyd & Cameron SubSingle Family
Taxes:$11,627
Elementary School: Southside Elementary
Remarks: Discover this UNIQUELY RARE OPPORTUNITY in the Coveted West of the Trail Neighborhood, amongst other very beautiful multi-million-dollar homes (two back-to-back lots, 1894 Loma Linda with frontage of 78’ and 1891 Prospect with frontage of 88’ with depth of 296’ for a total of both properties). The property on Loma Linda side is located on a quiet cul de sac at the end of the street. The two properties situated over half an acre have sewer and electric ready at the property and mature grand palms. Explore the potential opportunities this unique property offers! In combining these two lots you will have endless opportunities to customize the property to your vision. Whether you're seeking a family compound, multi-family development, or a dream home with additional income potential, this property delivers unmatched flexibility. Generate immediate income with existing rentals—Loma Linda is currently rented at $5,500 annually, and the adjacent lot is listed at $2,600 for annual rental—or live in one home while you plan and build on the other. With no flood zone concerns and established electrical and sewer connections, the property is ready to bring your vision to life. Location is exceptional with “A” rated Southside Elementary School, minutes to Southside Village shops and dining options, minutes to Sarasota Memorial Hospital, Downtown Sarasota and all the cultural amenities, Siesta Key beach and St. Armand’s Circle. Don’t miss this rare opportunity to create your perfect Sarasota retreat! Sold "as is."
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Beth Harris (941-321-7148)
1891 PROSPECT ST, SARASOTA, FL 34239
$2,500,00036 Days on yellowkey MLS ID: A4685965
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 1091 Built: 1950 Tax: $10,285 (2025)Community: Floyd & Cameron SubSingle Family
Taxes:$10,285
3549 65TH AVENUE CIR E, SARASOTA, FL 34243
$295,26088 Days on yellowkey MLS ID: A4679531
0 Days Off yellowkey (back on 3/30/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1036 Built: 1987Monthly Fee: $29 Tax: $1,836 (2024)Community: Centre LakeSingle Family
Taxes:$1,836
Tax Year: 2024
Remarks: Charming Sarasota Gem with Lake View — Under $300K! Discover affordable Florida living at its finest in this beautifully maintained 2-bedroom, 2-bath home with a versatile bonus room, perfect for a home office, guest space, or hobby area. Nestled in a well-established neighborhood, this property offers the perfect combination of privacy, comfort, and convenience. Step inside to find a bright, open layout featuring spacious living areas, a well-equipped kitchen, and large windows showcasing tranquil lake views. The private fenced yard provides plenty of room for outdoor entertaining, gardening, or simply enjoying the Florida sunshine. Located just 20 minutes from Sarasota’s best beaches, and close proximity shopping, dining, and cultural attractions UTC mall, this home offers incredible value in a sought-after area — all for under $300,000! Close to all but yet tucked away on a quiet cul-de-sac street. Don’t miss this rare opportunity to own a lake-view home in a desired Sarasota community. Schedule your private showing today!
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Cg Wolynski (860-671-0026)
17001 DEER PRAIRIE DR, SARASOTA, FL 34240
$2,000,00039 Days on yellowkey MLS ID: A4684995
1 Days Off yellowkey (back on 3/30/2026)
Bed: 5 Bath: 4.0 Liv Area Sq Ft: 3687 Built: 2008Monthly Fee: $83 Tax: $13,656 (2025)Community: Deer HammockSingle Family
Taxes:$13,656
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to an extraordinary, gated estate in Sarasota, FL, where nearly 5 private acres create the perfect backdrop for luxury living. This one-of-a-kind property boasts 3 gates for security & convenience. Behind board fencing, the estate ensures privacy, a long paver-brick drive, & curated landscaping. A serene pond enhances the beauty, making this an ideal retreat for those seeking space & premier amenities. A standout is the expansive detached bldg (approx. 2,100 sq. ft.), perfect for RVs, car collectors, or boaters. It offers parking for up to potentially 8 cars via tandem bays, an RV-height bay, & space for a boat or rec vehicles, accommodating up to a 34-ft boat or RV. There's a reinforced attic for storage, plus a beautifully finished guest studio apt. Ideal for multigenerational living or as an income-producing rental, this space features tile floors, crown molding, barn door, kitchenette w/ pantry, white cabinets, full bath, & independent climate control. The main residence presents a Mediterranean-style tile roof, welcoming porch w/ custom tile inset, arched dbl doors, & side-entry 2-car garage w/ resurfaced floor. Inside are 4 BRs, 3 baths, & a versatile den/study—providing flexible space for work or relaxation. Detailed ceilings, textured walls, designer/recessed lighting, ceramic tile, & wood floors add sophistication & warmth. A grand foyer w/ illuminated art niches, elegant columns, & a coffered ceiling welcomes you. Entertain in a formal dining/living area w/ stately columns, fireplace, & direct lanai access. The gourmet kitchen features white cabinets, subway-tile backsplash, lighted display cabs, premium appliances, breakfast bar, walk-in pantry, coffee bar, quartz counters, & butler’s pantry upgrade. Enjoy a breakfast nook w/ aquarium glass windows overlooking the pool, lanai, & acreage. Retreat to a warm family rm w/ coffered ceiling & fireplace or unwind in a luxurious primary suite w/ dbl doors, wood floors, triple sliders to the pool, dual walk-in closets, & spa-like bath. One add'l BR has walk-in closet, all have crown molding, & access to a beautiful guest bath w/ quartz. The separate studio apt provides a 4th bath, affording privacy & convenience for guests or extended stays. Functional spaces include laundry/craft rm (safe rm). Experience the FL lifestyle w/ an expansive covered lanai featuring a summer kitchen, granite bar, & a heated saltwater pool & spa w/ Pebble Tec finish and a new micro-mesh pool cage—ideal for entertaining or relaxing in total privacy. This outdoor oasis also grants convenient access to a pool bath w/ quartz. Deer Hammock luxury estate offers an exceptional blend of space, elegance, & security, conveniently located just east of I-75 in Sarasota County near local amenities. For added peace of mind, the estate has impact windows, hurricane shutters, a whole-house generator & 30 days propane storage, ensuring continuous comfort regardless of weather or outages. Picture cozy evenings by the fire pit under a starlit sky, w/ the excitement of bringing your horses to explore this beautiful setting. It's the perfect canvas for a dream equestrian estate! This home provides an impressive range of amenities that can't all be detailed here, making it ideal for those seeking a spacious country getaway and representing a remarkable opportunity, enhanced by deed restrictions that ensure the neighborhood’s visual appeal & protect property values.
Listing is courtesy of: CANDY SWICK & COMPANY (941-954-9000)
Listing Agent: Candy Swick (941-376-9000)
1368 21ST ST, SARASOTA, FL 34234
$339,000209 Days on yellowkey MLS ID: A4666082
2 Days Off yellowkey (back on 3/30/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1286 Built: 2008 Tax: $1,128 (2024)Community: Hillcrest 3Rd Add ToSingle Family
Taxes:$1,128
Remarks: Back on market through no fault of seller/property—buyer financing fell through. Inspection was completed. Looking for a fully remodeled home just minutes from Downtown Sarasota and some of the most beautiful beaches in the country? Look no further! This stunning 3-bedroom, 2-bathroom home offers 1,286 sq ft of stylish and modern living space, situated in a prime location with no rental restrictions – making it a fantastic investment property or a perfect winter getaway. Recent 2025 Renovations Include: -Fresh interior and exterior paint -New kitchen with quartz countertops and brand-new appliances -Remodeled bathrooms featuring elegant porcelain tile -All-new interior & exterior doors -Luxury vinyl plank flooring throughout -Updated plumbing and electrical fixtures -New light fixtures, outlets, and switches -HVAC system serviced with new grilles installed -New backyard fencing for added privacy Whether you're looking for a turnkey home, a vacation retreat, or a high-demand rental, this property checks every box. Located in a thriving area just a short drive to Lido Beach, Siesta Key, St. Armands Circle, shopping, dining, arts, and culture — this home blends lifestyle, comfort, and opportunity. Highlights: -No HOA or deed restrictions -Short-term & long-term rental friendly -Minutes to Downtown Sarasota & beaches -Move-in ready with high-end finishes Schedule your private showing today and make this beautiful Sarasota home yours before it's gone!
Listing is courtesy of: RAYNARD REALTY GROUP LLC (786-201-8463)
Listing Agent: Julien Raynard (786-201-8463)
724 CROSSWIND AVE, SARASOTA, FL 34240
$1,595,000106 Days on yellowkey MLS ID: A4673669
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 2688 Built: 2021Monthly Fee: $419 Tax: $20,062 (2025)Community: Lakehouse Cove At WatersideSingle Family
Taxes:$20,062
Remarks: MAJOR PRICE IMPROVEMENT - Welcome to 724 Crosswind Avenue, an elegant custom-built Lee Wetherington home that reflects timeless craftsmanship and thoughtful design. In a quiet, private enclave surrounded by lush preserves and vibrant wetlands, this 2,688-square-foot, single-story residence offers breathtaking views of abundant wildlife, including waterfowl, birds, deer and majestic eagles, creating a serene setting. Designed for relaxation and entertaining, the home features three spacious bedrooms, a private den and three full baths. From the moment you enter through the double glass doors, you’re greeted by a seamless, open flow and refined details throughout. The gourmet kitchen is a chef’s dream, showcasing top-of-the-line Monogram appliances, a gas cooktop, built-in ovens, custom wood cabinetry with deep drawers, quartz countertops and backsplash walls, a large walk-in pantry, and an oversized island with breakfast bar seating, ideal for casual dining and gatherings. The great room serves as the heart of the home, highlighted by soaring ceilings, built-in display shelving, and a dramatic wall of sliding glass doors that flood the space with natural light while opening to the lanai and preserving panoramic views of the surrounding landscape. The open-concept coastal design flows effortlessly into the dining area and kitchen, creating a warm, inviting atmosphere ideal for entertaining. A formal dining room is conveniently off the kitchen and features glass doors that lead to an outdoor dining area. The private den or office provides a peaceful retreat, complete with French doors for added privacy. The primary suite is a luxurious sanctuary featuring two custom-designed walk-in closets and a spa-inspired en-suite bath with dual vanities, a soaking tub and a floor-to-ceiling tiled walk-in shower. Two additional guest suites, each with its bath and generous closet space, ensure comfort and privacy for family and visitors alike. Step outside to your resort-style outdoor oasis designed for the ultimate Florida lifestyle. This exceptional space includes a heated saltwater pool and spa, a fully equipped outdoor kitchen, two covered loggias offering multiple entertaining areas and a panoramic screen enclosure with uninterrupted preserve views. Enjoy peaceful mornings on the lanai as you take in breathtaking sunrises and tranquil surroundings. Additional features include impact-resistant windows and doors, high and tray ceilings, crown molding, engineered hardwood and tile flooring throughout with no carpet, a spacious laundry room with ample storage, a separate climate-controlled storage room, and a three-car side-load garage with epoxy flooring. Plantation shutters, custom window treatments, built-in speakers, lush tropical landscaping, and accent lighting further enhance the home’s elegance and curb appeal. This custom Lee Wetherington home exemplifies a fusion of design and functionality, promising a life of unparalleled luxury and comfort all in Lakehouse Cove at Waterside. Lakehouse Cove community at Waterside boasts 20 serene shorelines, nature preserves and trails. Residents of Lakehouse Cove enjoy a richly appointed amenity center featuring a resort-style pool, spa, clubhouse with kitchen and scenic outdoor verandas, fire pits, pickleball courts, meeting and game room, and state-of-the-art fitness facility. Catch the Lakehouse Cove water taxi to Waterside Place Marina every Sunday for the farmers market.
3732 SURREY LN, SARASOTA, FL 34235
$524,000111 Days on yellowkey MLS ID: A4676503
3 Days Off yellowkey (back on 3/30/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 2267 Built: 1989Monthly Fee: $127 Tax: $3,483 (2025)Community: The MeadowsSingle Family
Taxes:$3,483
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Price Reduced $125,000 from original list price and is priced to sell! BRING ALL OFFERS! Seller’s are willing to negotiate! This home is looking for its forever family! Don’t pass this up. Welcome to The Meadows! Where lifestyle and leisure meet. In a lush, vibrant community just minutes from downtown Sarasota, the UTC Mall and Interstate 75, The Meadows is home to three distinctive golf courses, The Meadows Golf Course, The Groves and The Highlands. Whether you're looking to stay active, socialize or simply unwind, The Meadows offers something for everyone, from engaging social events and educational programs to recreational activities. Enjoy 14 acres of oak-canopied walking, biking and nature trails that weave throughout the community, ideal for peaceful strolls or invigorating outdoor adventures. This three-bedroom home, in the heart of The Meadows, has a large family room attached to the kitchen with a wood-burning fireplace for those chilly nights when you need some extra warmth. The kitchen has stainless steel appliances with a new Bosch dishwasher and a breakfast nook and eat-in counter. The formal living and dining rooms are open for entertaining. The sliding glass doors open to a large lanai with an inviting pool for cooling off on those extra-hot Florida days. The garage has a workbench for all the tools and water heater is new.
Listing Agent: Alfredda Smith Hurst, Pa (941-504-5758)
5311 CREEK DR, SARASOTA, FL 34231
$590,000474 Days on yellowkey MLS ID: A4633792
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1816 Built: 1978 Tax: $5,683 (2024)Community: Phillippi CrestSingle Family
Taxes:$5,683
Remarks: This 3-bedroom, 2.5-bathroom home is just 15 minutes from one of the best beaches in the USA. With a custom-made playhouse, heated pool, and custom outdoor shower, this home is perfect for families. The kitchen features granite countertops, and there are two AC units. The one-car garage can be converted into a two-car garage, and there are two hidden storage areas in the master suite. Recent updates include a new roof(2022), laminate flooring(2023), fresh interior paint(2022), a new water heater in 2022, a new dishwasher(2025)New disposal(2024), and a new fence installed(2024). This home was also converted from a well setup for water to a city water hookup in 2024. Located in one of the best school districts in Sarasota County, this home offers comfort and luxury in a prime location. Schedule your showing today.
Listing is courtesy of: WHITE SANDS REALTY GROUP FL (941-923-5835)
Listing Agent: Mario Petitti (941-822-6500)
7918 CYPRESS LAKE DR, SARASOTA, FL 34243
$475,00041 Days on yellowkey MLS ID: TB8485236
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 2261 Built: 1981Monthly Fee: $9 Tax: $6,482 (2025)Community: Desoto Lakes Cntry Clb Clny 5Single Family
Taxes:$6,482
Elementary School: Kinnan Elementary
High School: Braden River High
Middle School: Braden River Middle
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Experience refined Florida living in this beautifully upgraded 3-bedroom, 2.5-bath residence offering over 2,200 square feet of thoughtfully designed living space, perfectly situated on an expansive .26-acre lot in Sarasota just off University Parkway. This exceptional home blends elegant finishes, modern upgrades, and comfortable indoor-outdoor living in one of Sarasota’s most convenient locations. From the moment you arrive, the home makes a striking impression with its circular epoxy-finished driveway, brand new coach lights, and elegant travertine front entry, leading through a glass front door with sidelights into a bright and welcoming interior. Inside, sophisticated architectural details include crown molding, rounded archways, plantation shutters, chair rail accents, and ceramic tile flooring throughout the main living areas and primary suite, creating a seamless blend of style and functionality. The gourmet kitchen serves as the heart of the home and showcases custom mahogany cabinetry with decorative end panels and integrated lighting above and below, granite countertops, stainless steel appliances, a cooktop with vent hood, built-in wall oven, microwave drawer, tile backsplash, glass-front cabinetry, and a spacious island ideal for casual dining and entertaining. The kitchen flows effortlessly into the dining and living areas, enhanced by sliding glass doors that open to the expansive screened lanai, creating the perfect indoor-outdoor lifestyle. The luxurious primary suite offers private access to the lanai and features an oversized walk-in closet and a spa-inspired en-suite bathroom with a soaking tub, walk-in shower with glass enclosure, elegant vanity, and a pocket door entry for added privacy. All three bedrooms feature walk-in closets, providing exceptional storage throughout the home, along with multiple additional storage closets. Outdoor living is equally impressive with a large screened lanai overlooking the beautifully landscaped and fully vinyl-fenced backyard. The spacious yard offers plenty of room to add a swimming pool and features mature oak and palm trees along with a producing loquat tree, creating a peaceful Florida setting perfect for relaxing or entertaining. This home has been thoughtfully updated, including new interior and exterior paint, a new roof, new carpet in guest bedrooms, a recently replaced A/C system within the last three years, and a newly installed HALO whole-home air purification system. Additional highlights include a new impact-rated garage side entry door, a spacious two-car garage with built-in storage cabinets, full-size washer and dryer in the laundry room, and ceiling fans throughout. A convenient half bath with a full white vanity is ideal for guests. Located in an excellent school district with no flood insurance required, the home is just minutes from University Parkway’s premier shopping, dining, and entertainment, including University Town Center Mall, Nathan Benderson Park, and Waterside at Lakewood Ranch. Golf enthusiasts will appreciate being close to both Palm Aire Golf & Country Club and University Park Country Club, offering exceptional courses and amenities nearby. This is a rare opportunity to enjoy space, upgrades, and an unbeatable Sarasota location.
Listing is courtesy of: RE/MAX REALTY UNLIMITED (813-684-0016)
Listing Agent: Jennifer Fieo (813-494-4873)
3234 RESTFUL LN, SARASOTA, FL 34231
$399,000278 Days on yellowkey MLS ID: A4658946
0 Days Off yellowkey (back on 3/27/2026)
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 1985 Built: 1957 Tax: $3,115 (2024)Community: Restful PinesSingle Family
Taxes:$3,115
Elementary School: Gulf Gate Elementary
High School: Riverview High
Remarks: Under contract-accepting backup offers. NEW PRICE! MOTIVATED SELLER! Welcome to this beautifully remodeled 4-bedroom, 3-bath home located in the desirable Restful Pines neighborhood in South Sarasota’s 34231 zip code. Offering nearly 2,000 square feet of modern living space, this home features two spacious living areas, generously sized bedrooms, and a flexible layout perfect for families or entertaining. Enjoy peace of mind with a brand-new roof and air conditioning system, both installed in 2024. The home has been upgraded throughout with new windows and stylish modern doors that enhance both energy efficiency and curb appeal. The kitchen shines with sleek quartz countertops, stainless steel appliances, and a contemporary design that flows seamlessly into the main living spaces. All three bathrooms have been beautifully updated with new vanities, glass-enclosed showers, and modern tile finishes. Set on a quarter-acre lot in Flood Zone X, this home has never flooded and offers a large backyard with plenty of room to add a pool, detached garage, or storage building. Best of all, there are no HOA or CDD fees, giving you the freedom to enjoy your property without added restrictions or costs. Enjoy the convenience of walking to A+ rated Riverview High School and nearby Red Bug Slough Preserve with scenic trails and nature views. You're also just minutes from Siesta Key’s world-famous beaches, Detwiler’s Farm Market, and the vibrant Gulf Gate dining and shopping district. With a motivated seller, this move-in ready home is a fantastic opportunity in one of Sarasota’s most convenient and sought-after locations!
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Roni-Marie Gold, Pa (941-487-0105)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.