Location: Sarasota
Do Not Show Listings
3225 GULF WATCH CT, SARASOTA, FL 34231
$415,00081 Days on yellowkey MLS ID: TB8483842
REDUCED by $5,000 (1.2%) on 04/07/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1216 Built: 1990Monthly Fee: $125 Tax: $3,345 (2025)Community: Gulf Gate GlenSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,345
Elementary School: Gulf Gate Elementary
High School: Riverview High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: Experience effortless coastal living in this light-filled 2BR/2BA villa, located in the peaceful community of Gulf Gate Glen just three miles from the iconic quartz sands of Siesta Key. Nestled on a tranquil, tree-canopied street, this home offers a rare "lock-and-leave" lifestyle where the HOA manages all landscaping and irrigation—leaving your weekends free for the beach. The interior features an inviting open-concept design with soaring vaulted ceilings and a private covered lanai perfect for your morning coffee. Perfectly situated for convenience, just minutes from Trader Joe’s, Walmart, and local favorites like Walt’s Fish Market and Phillippi Creek Oyster Bar. Modern, maintenance-free, and move-in ready.
Listing is courtesy of: REDFIN CORPORATION (617-458-2883)
Listing Agent: Lynn Lynch Magaro (267-621-1323)
156 TALL TREES CT, SARASOTA, FL 34232
$510,00090 Days on yellowkey MLS ID: TB8482194
REDUCED by $15,000 (2.9%) on 04/12/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1990 Built: 1998Monthly Fee: $199 Tax: $5,036 (2025)Community: Oak Court Ph 1-BSpa: NoSingle Family
Taxes:$5,036
Elementary School: None
High School: None
Middle School: None
Remarks: PRICE ADJUSTMENT! Nestled in an enclave of 62 homes just off of Fruitville Road, tucked back behind gates, this charming home features three bedrooms, two bathrooms in an impeccably cared for setting. The home has a large living dining area, a separate family room, kitchen with island and granite countertops and a breakfast nook adjacent to the kitchen. The primary bedroom suite features a large walk in closet, dual sinks with granite countertops, huge garden bath and walk in shower. There is also a large walk in closet, just off the primary bedroom. The other two bedrooms are separated from the primary and feature large spaces and built in closets. Outside, the home has a huge screened garden just outside the sliding doors and a large outdoor garden with ample trees and landscaping. The community features a pool and cabana on a lake with a fountain. This home is located just a couple miles to downtown Sarasota and easy access to I-75.
Listing is courtesy of: LOKATION (954-545-5583)
Listing Agent: Rick Waid (941-735-4207)
5334 CALLE FLORIDA, SARASOTA, FL 34242
$1,870,000156 Days on yellowkey MLS ID: A4676260
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2838 Built: 1998 Tax: $5,619 (2025)Community: Sarasota BeachSpa: YesSingle Family
Taxes:$5,619
Remarks: Fantastic opportunity to own a unique home on Palm Island, in this exceptional Siesta Key residence, ideally located at 5334 Calle Florida. Situated on a large lot and elevated approximately 10 feet above sea level, the main home has never flooded during any storms, offering peace of mind along with island luxury. This 4-bedroom, 3-bathroom home features 2,838 square feet of thoughtfully designed living space highlighted by a dramatic great room with soaring 20-foot ceilings, creating an open and airy coastal feel. The large primary suite has a custom built window seat, 2 walk in closets and an oversized primary bathroom. The entire home features built in speakers, including the back porch. Designed for comfort and efficiency, the home is equipped with a three-zone air conditioning system and hurricane-rated Kevlar screens, hurricane rated garage and front door for added protection. The spacious two-car garage provides ample storage, perfect for island living. The exterior is landscaped with outdoor lights and power in soffits for seasonal or all year round lighting. Outdoor living is elevated—literally—with an elevated, heated pool and hot tub, an outdoor shower, and plenty of space to relax or entertain in true Florida style. Located on Palm Island, just moments from the world-renowned Siesta Key Beach, this property offers the perfect blend of privacy, elevation, and coastal charm. Whether as a primary residence or luxury retreat, this home is a rare opportunity to own a high-and-dry island property in one of Sarasota’s most sought-after neighborhoods. Roof replaced 2021, Pool resurfaced 2024, Pool cage repainted and rescreened 2025, Water heater 2025. Unique Architectural Details *** Custom Built *** Oversized Primary Suite *** Soaring Ceilings *** Open Concept *** Elevated Key West Style *** Screened Lanai
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Niall Phelan (941-914-8589)
4672 ALEXANDER POPE LN, SARASOTA, FL 34241
$899,000194 Days on yellowkey MLS ID: A4672673
REDUCED by $50,000 (5.3%) on 05/01/2026
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3838 Built: 1978 Tax: $8,264 (2024)Community: Bent Tree VillageSpa: NoSingle Family
Taxes:$8,264
Elementary School: Lakeview Elementary
High School: Sarasota High
Tax Year: 2024
Middle School: Sarasota Middle
Remarks: Welcome to this exceptional 5 bedroom, 3.5 bath home perfectly positioned at the end of a peaceful cul-de-sac on Bent Tree Golf Club. Designed for both upscale entertaining and comfortable everyday living, this residence offers a rare combination of privacy, elegance, and modern upgrades. Step inside to find formal living and dining rooms, crown molding throughout, and two charming wood-burning fireplaces that add warmth and character. The large designer kitchen features premium finishes, generous counter space, and seamless flow to the main living areas—ideal for gatherings of any size, a full wet bar elevates your hosting experience. The home features a NEW ROOF, NEW POOL CAGE and FULLY PAID SOLAR SYSTEM which provide unmatched efficiency and value for years to come. This smart home also includes a home gym, comprehensive security system, water softener/filtration, and thoughtful upgrades throughout. Outside, enjoy breathtaking sunset views from your private screened lanai and sparkling pool—your own serene retreat overlooking a manicured golf course. A rare opportunity to own a beautifully upgraded, move-in ready home in one of the area’s most sought-after neighborhoods.
Listing is courtesy of: ANDRE LECLAIR PROPERTIES LLC (603-234-6480)
Listing Agent: Christian Higgins (772-532-8857)
3174 PEACHTREE ST, SARASOTA, FL 34231
$468,00024 Days on yellowkey MLS ID: A4692949
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1548 Built: 1988 Tax: $4,143 (2025)Community: Flora-Villa SubSingle Family
Taxes:$4,143
Elementary School: Wilkinson Elementary
Remarks: An actual peach! This lovely sunshine-y home on Peachtree Street is ready for new memories to be made. Located right in the heart of Sarasota, the neighborhood of South Gate Ridge is 10 minutes from everything. This lofty, light filled house is one block from the locally adored Bee Ridge Park, where neighbors gather to play in local softball games; enjoy an evening walk with the puppy; push their kiddos on the swing; or tend to their vegetables in the robust community garden. Tucked back on this spacious lot, this home feels private and peaceful. Once inside, the open and airy floor plan is punctuated by an open loft that is framed by a beautiful wood bannister, adding warmth and dimension to the entire space. A LARGE Primary Suite with West facing windows, wide closets, and a newly remodeled double vanity bathroom, sits on the main level. The already sizable living room, anchored around a stone fireplace, feels even more voluminous with vaulted ceilings and large windows. A BRAND NEW kitchen has been recently completed featuring soft close cabinets and drawers with built in organizers. Coastal blue tiles add a vibrant pop of color that will be on trend for years to come. Upstairs, two large bedrooms share the cozy loft space as well as the freshly RENOVATED second bathroom. Large, New Impact Sliders open up the entire back of the home to the large private backyard with an awesome deck and room for a pool. A true two car garage has its own loft space for extra storage and the brand new washer and dryer conveys with the sale. NEW ROOF in 2023!! Fresh paint inside AND out. All this home needs is you ;) This peach of a property could not be cuter and is completely move-in ready!
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Kelly Drost (941-822-6926)
10125 CRYSTAL ISLES CIR, SARASOTA, FL 34241
$889,00049 Days on yellowkey MLS ID: A4689256
1 Days Off yellowkey (back on 5/6/2026)
Bed: 3 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 2514 Built: 2025Monthly Fee: $358 Tax: $3,595 (2025)Community: Grand Park Ph 2 RepSpa: YesSingle Family
Taxes:$3,595
Remarks: Under contract-accepting backup offers. Better than new and beautifully upgraded, this exceptional 2025-built Harvest 3 model in Grand Park delivers luxury living without the wait for new construction. Meticulously maintained, pride of ownership shines throughout every detail of this stunning residence, thoughtfully enhanced with designer finishes, custom lighting, upgraded ceiling fans, and a two-station outdoor kitchen created for effortless entertaining. Offering 3 spacious bedrooms + private den, 3 full baths, a convenient pool bath, and a tandem 3-car garage, the thoughtfully designed split-bedroom floor plan balances comfort and privacy with elegant everyday living. Soaring 10-foot coffered ceilings, abundant natural light, and architectural details create an inviting open-concept atmosphere that feels both refined and warm. At the center of the home, the chef-inspired gourmet kitchen is a true showpiece, featuring a natural gas 5-burner cooktop, built-in wall oven, oversized quartz island, upgraded gold hardware, and designer pendant lighting—perfectly designed for gathering, hosting, and making memories. Step outside to your own private resort-style retreat. The custom heated pool and spa are surrounded by an expansive brick paver lanai and complemented by a fully equipped outdoor kitchen with professional grill, exhaust hood, granite countertops, outdoor refrigerator, and generous prep space—creating the ultimate Florida outdoor living experience. The luxurious primary suite is a private sanctuary, complete with spacious walk-in closets and a spa-inspired bath designed for relaxation and indulgence. Throughout the home extensive upgrades replace original builder selections with elevated, higher-end fixtures and finishes, making this residence truly one of a kind and difficult to duplicate at this price point. Located within Grand Park’s gated, amenity-rich community, residents enjoy two resort-style pools, an elegant clubhouse, fitness center with aerobics studio, pickleball, tennis courts, sports court, walking trails, dog park, and lush green spaces—all conveniently located near I-75, providing easy access to shopping, dining, and Sarasota’s world-renowned Gulf Coast beaches. One look, and you will fall in love. Schedule your private tour today and experience luxury living not to be missed a must see.
Listing is courtesy of: WEICHERT REALTORS HALLMARK PRO (941-706-2142)
Listing Agent: Georgia Sotiriou (301-346-6227)
9181 FLORIDA ROCK TRL, SARASOTA, FL 34240
$814,900171 Days on yellowkey MLS ID: A4675151
2 Days Off yellowkey (back on 5/9/2026)
Bed: 2 Bath: 2.0 Gar: 5 Liv Area Sq Ft: 2078 Built: 2025Monthly Fee: $388 Tax: $3,497 (2024)Community: Shellstone At WatersideSingle Family
Taxes:$3,497
Elementary School: Tatum Ridge Elementary
High School: Booker High
Middle School: McIntosh Middle
Remarks: A Unique Opportunity in Shellstone! The Halyard floor plan with an expanded 5-car garage, originally constructed for the Homes by Towne team. Ideal for car collectors, a workshop, or storage. This beautifully upgraded 2-bedroom + den, 2-bath home offers elegant tray ceilings in the foyer and great room, and spacious living areas perfect for entertaining. The chef's kitchen includes a large island, walk-in pantry, and abundant workspace. Community amenities include The Summit at Shellstone Amenity Center with a Social Hall, Fitness Center, Pool and Spa, Firepit, Poolside Cabanas, Poolside BBQ Grills, and Fitness Lawn. Residents also have access to Midway Park featuring a Pro Shop, Screened Pavilion, Play Areas, Dog Parks, Basketball Court, 8 Pickleball Courts, 6 Tennis Courts, Kayak Launch, Outdoor Fitness Area, and Shaded Picnic Areas. Shellstone offers convenient access to Downtown Waterside Place, Gulf Coast beaches, world-class dining and shopping, several hospitals, and is located within the Sarasota School System. Sarasota International Airport is approximately 25 minutes away, and Tampa International Airport is approximately 70 minutes away.
Listing is courtesy of: HOMES BY TOWNE REALTY INC (941-907-9799)
Listing Agent: Marissa Stephenson (941-448-1755)
4436 CALLE SERENA, SARASOTA, FL 34238
$775,00024 Days on yellowkey MLS ID: A4691149
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3037 Built: 1989Monthly Fee: $250 Tax: $4,207 (2025)Community: Prestancia/Villa Las PalmerasSingle Family
Taxes:$4,207
Remarks: A truly striking, fully remodeled golf course residence where dramatic design meets effortless, maintenance-free living. Completely reimagined and extensively remodeled within the past five years, this exceptional home offers a rare blend of modern elegance, quality craftsmanship, and breathtaking golf course views—all within a completely maintenance-free setting.From the moment you arrive, the upgraded landscaping sets the tone for what awaits inside. The main living areas are nothing short of spectacular, featuring soaring 24-foot ceilings and a dramatic 20-foot stacked stone accent wall with an electric fireplace and recessed TV—creating a true architectural centerpiece. Throughout the home, French oak luxury vinyl plank flooring, installed on the diagonal, adds warmth, texture, and a refined, contemporary feel. Designed for both everyday living and entertaining, the home offers 3 bedrooms plus a versatile bonus room/office and 3.5 bathrooms. The kitchen is equally impressive, showcasing custom cabinetry, exotic granite countertops, and newer stainless-steel appliances, blending beauty and functionality. The primary suite serves as a private retreat, highlighted by a spa-inspired bath featuring an expansive wet room with granite walls, a soaking tub, floating cabinetry, and custom lighting—delivering a true resort-style experience. Perfectly positioned to capture beautiful southern exposure, the home overlooks the 15th hole of the renowned TPC at Prestancia Stadium Course, offering picturesque views and abundant natural light throughout the day. Additional highlights include an epoxy-coated garage floor and abundant storage throughout, further enhancing the home’s functionality and appeal. This is a rare opportunity to own a fully updated, move-in-ready home in a premier golf course setting—where every detail has been thoughtfully designed and every convenience has been considered.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Steve Abbe (941-400-3969)
4068 LYNDHURST CT, SARASOTA, FL 34235
$488,00044 Days on yellowkey MLS ID: A4690209
1 Days Off yellowkey (back on 5/9/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1963 Built: 1987Monthly Fee: $567 Tax: $4,495 (2025)Community: Meadows TheSingle Family
Taxes:$4,495
Elementary School: Gocio Elementary
Middle School: Booker Middle
Remarks: Under contract-accepting backup offers. Tucked within the desirable Lyndhurst enclave of The Meadows, this beautifully maintained 3-bedroom, 2-bath single-family residence offers a blend of privacy, character, and effortless Florida living. A pavered driveway and tropically landscaped, gated walkway welcome you to a charming side-entry front door. Step into a light-filled interior featuring porcelain tile flooring and ceiling fans throughout, complemented by neutral tones, unique architectural angles, and subtle accent lighting that create a bright, airy ambiance with a relaxed, beach-inspired feel. The living and dining areas are the heart of the home, enhanced by a skylight, a cozy wood-burning fireplace, and a wet bar with built-in cabinetry—perfect for entertaining. The eat-in kitchen is both stylish and functional, showcasing light soft-close cabinetry, quartz countertops, and abundant windows that invite in natural light. A door leads to a private, walled privacy garden complete with a pergola—an ideal spot for morning coffee or quiet evenings. Just off the kitchen, the inside laundry room offers added convenience with upper cabinetry for storage. An enclosed all-weather bonus room, lined with windows, seamlessly connects the living room to the lanai, expanding your living space year-round. The spacious primary suite features sliding glass doors to this bonus area, transom windows, and a large walk-in closet with built-ins. The ensuite bath is thoughtfully designed with quartz countertops, dual sinks with a makeup area, a sunken tub beneath a skylight, and a separate shower, toilet, and additional sink with direct access to the lanai - making it an ideal future pool bath should new owners choose to add a pool. Two guest bedrooms provide flexibility and comfort—one generously sized with a walk-in closet, and the other featuring built-in cabinetry, currently utilized as a den or office. The guest bath includes a separate sink area with quartz countertops and a beautifully updated tiled shower with glass doors. Outdoors, the pebbled and recently rescreened lanai offers tranquil tropical views of the 11th fairway and green, creating a serene backdrop for relaxation or entertaining. The attached two-car garage is equally impressive, featuring an epoxy floor, storage cabinets, pegboard, new pull-down attic stairs, and direct access to the private courtyard. Recent upgrades include NEW HVAC in 2023, refrigerator, dishwasher and disposal in 2022, and washer and dryer in 2021. Enjoy low-maintenance living with an HOA that covers landscaping outside the lanai, roof maintenance and replacement (roof replaced in 2012), exterior home care and painting, irrigation, and exterior pest control—allowing you to fully embrace the Florida lifestyle in one of Sarasota’s most sought-after communities. Lyndhurst also offers a screened community pool and walking trails. Just a 15-minute drive outside this peaceful enclave is downtown Sarasota, with shopping, arts & theatres, museums, dining and entertainment, top-ranked healthcare, beaches and SRQ International Airport. One mile east is the convenience of I-75, University Town Center with over 300 nationally known and homegrown shops, restaurants, fitness studios, services and attractions, the Nate Benderson Park, home of world-class rowing events and the Mote Marine Aquarium. Please note: three exterior SimpliSafe cameras are in place on the property and may be recording.
Listing is courtesy of: FINE PROPERTIES (941-782-0000)
Listing Agent: Daniela Soiman (941-779-4797)
6642 41ST STREET CIR E, SARASOTA, FL 34243
$458,00024 Days on yellowkey MLS ID: TB8506610
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1642 Built: 2007Monthly Fee: $577 Tax: $4,359 (2025)Community: Cascades At Sarasota Ph VSingle Family
Taxes:$4,359
Remarks: Location, Location, Location! Move in ready 2-bedroom, 2-bathroom home with a den in the highly desirable 55+ gated community, Cascades of Sarasota! As you walk through the front door you will notice an open floorplan with vaulted ceilings. The kitchen overlooks the living room and dining room and has been tastefully updated with new granite and new stainless appliances! The spacious master suite has two walk-in closets and a large en-suite making it the perfect private retreat after a long day. Enjoy Florida living on the screened in lanai overlooking the back yard. The Cascades of Sarasota is an active 55+ community and has a resort style indoor/outdoor swimming pool, tennis and pickleball courts, and bocce ball. A state-of-the-Art gym. It also has a variety of social events and functions throughout the year. The 25,000SF Clubhouse includes craft, card and game rooms. A large ballroom with kitchen facilities, billiards and a library. Come see why this community is in such high demand! Read Less
Listing is courtesy of: JACK KELLER INC (727-586-1497)
Listing Agent: John Keller (727-586-1497)
1837 WORRINGTON ST, SARASOTA, FL 34231
$619,00024 Days on yellowkey MLS ID: TB8504626
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1008 Built: 1952 Tax: $4,056 (2025)Community: South Highland Amd OfSingle Family
Taxes:$4,056
Remarks: Renovated 1150 sq. ft. beach cottage west of trail with open floorplan. Updated plumbing, new electric, new metal roof, AC 2020. Golf cart to all your favorite spots, Mortons, Libby's, Publix, EOS, Trader Joes, Walts Fish Market. 3 minute drive to Siesta Key bridge. Separate studio that can be used for office or in-law bedroom is not included in the listed square footage.
Listing is courtesy of: HOMECOIN.COM (888-400-2513)
Listing Agent: Jonathan Minerick (888-400-2513)
4300 EASTERN PKWY, SARASOTA, FL 34233
$549,00024 Days on yellowkey MLS ID: N6144098
Bed: 2 Bath: 1.0 Gar: 3 Liv Area Sq Ft: 1284 Built: 1956 Tax: $3,231 (2025)Community: Shady OaksSingle Family
Taxes:$3,231
Remarks: Rare opportunity to own a private retreat with space, flexibility, and an unbeatable location—all set on nearly an acre (.80 acres) in Sarasota. Properties like this are incredibly hard to find, offering no HOA, no CDD fees, and no deed restrictions. This well-maintained 2-bedroom, 1-bath home has been thoughtfully updated and offers excellent potential for expansion. Recent improvements include a new HVAC system, water heater, washer and dryer (2021), new kitchen appliances (2024), and a new shingle roof on the home along with a metal roof on the detached garage (2023). Set back from the road for added privacy, the property features a spacious open floor plan with flexible living options to suit a variety of lifestyles. The large lanai just off the kitchen and living area creates a perfect indoor-outdoor flow for relaxing or entertaining. One of the standout features is the impressive 30’ x 30’ detached garage, complete with two garage doors, an attached shed for additional storage, and its own electrical panel with a 220-amp receptacle—ideal for a workshop, business use, or hobbyist needs. With ample space for storage, recreation, or future customization, this property offers endless possibilities. Enjoy the privacy of a large homesite while being just minutes (approximately 5 minutes) from schools, shopping, dining, and Sarasota’s beautiful beaches. Move-in ready and full of potential—this is a truly unique opportunity you don’t want to miss.
Listing is courtesy of: KELLER WILLIAMS ISLAND LIFE REAL ESTATE (941-254-6467)
Listing Agent: Allison Bollero (941-451-7411)
10214 CRYSTAL ISLES CIR, SARASOTA, FL 34241
$739,90024 Days on yellowkey MLS ID: A4691742
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3028 Built: 2024Monthly Fee: $336 Tax: $9,557 (2025)Community: Grand Park Ph 2 RepSingle Family
Taxes:$9,557
Remarks: Welcome to the epitome of modern luxury in Grand Park with this stunning, newer construction home by Neal Communities. Situated on a preserve lot, this thoughtfully crafted home boasts 4 bedrooms, + den/office, 4 baths, and a massive second-floor bonus room, all backing onto serene, private conservation views. The open-concept floor plan is flooded with natural light, highlighting the chef’s kitchen equipped with quartz countertops, a gas range, a farmhouse sink, and a walk-in pantry. Designed for entertaining, the kitchen flows seamlessly into the living, dining, and outdoor patio spaces. The peaceful first-floor primary suite features conservation views, dual vanities, and his-and-her closets. The main floor is completed by two additional bedrooms, a den,/office, 2 storage rooms, and a dedicated laundry room. Upstairs, the expansive bonus room and fourth bedroom with an en-suite bath present unparalleled flexibility—ideal for a theater, game room, or private guest suite. Luxury upgrades abound, including 8' doors, wood-look ceramic tile, brand new carpet in rooms, and quartz countertops throughout. The exterior offers peace of mind with impact-rated windows/doors, a tile roof, and pre-wiring/plumbing for a custom outdoor kitchen and pool. Grand Park offers resort-style living with two pools, a splash pad, fitness center, dog park, and tennis/pickleball courts. Located just a few miles away from Sarasota's famous Siesta Key Beach, local parks, shopping, dining and more.
Listing is courtesy of: ASCENDIA REAL ESTATE (941-306-4242)
Listing Agent: Kim Gregory (941-716-2368)
7815 GENEVA LN, SARASOTA, FL 34243
$375,000111 Days on yellowkey MLS ID: W7882865
1 Days Off yellowkey (back on 5/8/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1533 Built: 1990Monthly Fee: $200 Tax: $5,093 (2024)Community: Treetops At North 40 - St CharlesSingle Family
Taxes:$5,093
Elementary School: Kinnan Elementary
High School: Southeast High
Middle School: Braden River Middle
Remarks: Under contract-accepting backup offers. Short Sale. FULLY LOADED—and FLAWLESSLY DONE! Tucked inside the boutique, tree-canopied ENCLAVE of Treetops at North Forty, this 3-bedroom, 2-bath single-family home delivers the rare combination of refined upgrades, peaceful surroundings, and an unbeatable central Sarasota location. Homes in this intimate community don’t come along often—especially not ones that have been this thoughtfully and thoroughly improved. Every inch of this home has been elevated with intention. Starting at the top, a BRAND-NEW ROOF and BRAND-NEW WATER HEATER take care of the big-ticket items buyers value most, while fresh interior and exterior paint create a crisp, cohesive look that feels both modern and timeless. The FULLY REMODELED KITCHEN is a true showpiece, featuring STONE countertops, all-new custom-style cabinetry, and a complete suite of BRAND-NEW APPLIANCES, designed to be as functional as it is beautiful. Whether you’re hosting friends or enjoying a quiet morning coffee, this space simply works. Step outside the breezeway, or plant an herb garden here, with tons of square footage for all of your plants. Both bathrooms have been COMPLETELY RENNOVATED with updated finishes, fixtures, showers and tubs, and a spa-inspired feel that turns everyday routines into small luxuries. Plush new carpet in the bedrooms creates a soft, comfortable retreat at the end of the day! A brand-new washer and dryer adds convenience, while the WHOLE HOME WATER PURIFICATION system quietly enhances daily living with cleaner, better-tasting water throughout the house. This home truly stands apart when it comes to storm preparedness. With a new roof already in place and a MANUAL-CAPABLE ELECTRIC AWNING that remains functional even during power outages, the home is thoughtfully equipped for Florida’s weather realities. Adding to its appeal, the property sits above the flood plain, offering increased confidence, reduced flood risk, and potentially lower insurance considerations—an increasingly important factor for today’s buyers. It’s a home designed not just to look good, but to perform well when it matters most. Outside, the lifestyle upgrades continue. The property is positioned on one of the largest lots in the community, backing up to protected CONSERVATION LAND for rare privacy and peaceful views with no rear neighbors. The brand-new electric awning with integrated lighting creates a shaded, flexible outdoor living space—perfect for relaxed evenings, weekend gatherings, or quiet moments surrounded by nature. Treetops at North Forty is a boutique community prized for its quiet charm, mature landscaping, and sense of retreat—yet it offers a COMMUNITY POOL, no age restrictions, no CDD fees, and a welcoming, neighborly atmosphere. All of this is just minutes from UTC Mall, SRQ Airport, New College, and the endless dining, shopping, and cultural experiences that make Sarasota so desirable. This home isn’t just updated—it’s curated, offering a polished, low-maintenance lifestyle in a community that feels private, established, and special! Opportunities like this don’t linger, so schedule your showing and experience it for yourself.
Listing is courtesy of: THE WILKINS WAY LLC (407-874-0230)
Listing Agent: Brooke Overton (315-439-3013)
1655 SOUTH DR, SARASOTA, FL 34239
$5,900,00092 Days on yellowkey MLS ID: A4684423
Bed: 5 Bath: 7.0 Gar: 3 Liv Area Sq Ft: 6355 Built: 2011Monthly Fee: $27 Tax: $34,625 (2025)Community: Cherokee ParkSpa: YesSingle Family
Taxes:$34,625
Elementary School: Southside Elementary
Remarks: One or more photo(s) has been virtually staged. In Sarasota's desired West of Trail enclave of Cherokee Park, 1655 South Drive, masterfully designed three-story estate where thoughtful architecture meets effortless luxury. Positioned on a homesite that is not in a Special Flood Hazard Area and enhanced with full home hurricane-impact glass and a whole-home generator, this residence offers the rare combination of refinement and peace of mind. Spanning 6,355+ square feet, the home features five bedrooms, five full baths and four half baths, with a layout tailored for grand entertaining and everyday ease. A rear three-car garage, accessed discreetly from South Lodge Drive, preserves the home's striking street presence. Inside, the main level unfolds into a wide-open living experience with a great room with wet bar, formal dining, and a showpiece chef's kitchen outfitted with Wolf dual-oven six-burner range, dual side by side 36” Sub-Zero Over-and-Under Refrigerator/Freezers, a Wolf microwave drawer, a Wolf warming drawer, and built-in Miele espresso machine. The first-floor primary suite is a private retreat, complete with an in-home gym, a spa-inspired bath and dual custom-fitted closets. A beautifully appointed guest suite (fifth bedroom) with en-suite bath also anchors the main level. Access to the upper floors is seamless via a dramatic staircase with custom wrought-iron railings or the private elevator. Upstairs, three additional en-suite bedrooms include custom walk-in closets, one thoughtfully designed with built-in bunk beds, plus a bonus club room with built-in desks and additional laundry for added convenience. Outdoors, the property transforms into a walled and gated resort-style oasis featuring a gas-heated saltwater pool with sun shelf and spa, and an artificial turf lounge/play area. A screened entertainment lounge with a convenient half pool bath connects to a full outdoor kitchen with sink, TV and gas grill, all complemented by a pergola and a mosquito misting system, ideal for Sarasota's seasons. Above the garage, a spectacular casita-style retreat, accessible by the home’s second private interior elevator or exterior spiral staircase, elevates entertaining to an entirely new level with a 2,000-bottle refrigerated wine room, a fully equipped wet bar, mini- fridge, clear ice maker, and dishwasher. Go onto the covered terrace with a gas fireplace, then unwind on the third floor in the private, pool-like infinity-edge spa, an experience that feels equal parts boutique resort and private club. Ideally in walking distance to A-rated Southside Elementary School, Southside Village, Sarasota Memorial Hospital, downtown Sarasota and short drive to the world-famous sands of Siesta Key Beach, this is a rare opportunity to own a bespoke residence in one of Sarasota's treasured neighborhoods.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Katy Mcbrayer (941-400-2406)
8267 SHADOW PINE WAY, SARASOTA, FL 34238
$637,500143 Days on yellowkey MLS ID: A4674924
0 Days Off yellowkey (back on 5/8/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2371 Built: 1990Monthly Fee: $186 Tax: $6,031 (2024)Community: Deer CreekSpa: NoSingle Family
Taxes:$6,031
Remarks: Under contract-accepting backup offers. Welcome to Florida living at its finest. Deer Creek 3-bedroom, 2-bath home with pond views and side-entry garage in a prime Sarasota location. Nestled in a peaceful and well-maintained community, this residence offers a rare combination of privacy, efficiency, and picturesque water views. Situated on a tranquil pond-front lot, the home features a 2-car side-entry garage, beautifully updated kitchens and baths, indoor laundry room, lush landscaping, and a irrigated yard. Inside, the thoughtfully designed split-bedroom floor plan includes spacious living areas, abundant natural light, and a charming wood-burning fireplace that creates a warm focal point for the family room. The kitchen and dining areas flow seamlessly for comfortable everyday living and entertaining. The home offers generously sized bedrooms, including a relaxing primary suite that provides a private retreat after a long day. Thoughtful design touches, ample storage, and natural light throughout enhance the sense of space and comfort. Major upgrades provide peace of mind and long-term value, including a brand-new roof (2025), newer A/C system (2019), and added blown-in insulation, enhancing both comfort and energy efficiency. NEW carpet in bedrooms! This residence offers a rare combination of privacy, efficiency, and picturesque water views situated on a tranquil pond-front lot, the home features a 2-car side-entry garage, lush landscaping, and a fully irrigated yard for easy, low-cost maintenance. The primary suite offers a relaxing retreat with serene pond views, while the additional bedrooms provide flexibility for family, guests, or a home office. Enjoy the beautiful pond views from several rooms — the perfect setting for morning coffee, sunset dinners, or simply unwinding. Ideally located just minutes from top-rated schools, shopping, dining, medical facilities, and Sarasota’s world-famous beaches, this home delivers the lifestyle today’s buyers are seeking. Whether you’re looking for a primary residence, seasonal escape, or investment opportunity, 8267 Shadow Pine Way offers exceptional value in one of Sarasota’s most desirable areas. Schedule your private showing today and discover why this home is the one you’ve been waiting for. Owner shared this home has a VA Assumable Loan at low 2.625 rate.
Listing is courtesy of: KATHLEEN GOFF LICENSE R.E. BROKER (941-350-3902)
Listing Agent: Kathleen Goff (941-350-3902)
16409 WINBURN PL, SARASOTA, FL 34240
$599,00031 Days on yellowkey MLS ID: A4691548
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1020 Built: 1985Monthly Fee: $63 Tax: $5,501 (2025)Community: Rainbow Ranch AcresSingle Family
Taxes:$5,501
Remarks: Under contract-accepting backup offers. A rare opportunity to own a unique 5-acre “Old Florida” property bordering the Myakka Preserve! This cedar house is totally private among native woods, palms and bamboo. Inside, you will find 2 bedrooms and 2 baths, plus a fully equipped, updated kitchen with modern appliances for comfortable living. This unique home features a solid black walnut floor and a wood-burning fireplace. Up the spiral staircase, you’ll find a loft bedroom with a newly updated bathroom. In the main floor bathroom, there’s a 102-year-old clawfoot tub with black walnut surround, and a washer/dryer hookup in place. The kitchen features solid countertops and solid beech wood cabinets. Watch the deer and other wildlife from the large porch and rear deck. Roof is new! AC is 5 years old. Irrigation available in multiple locations on the property. The Large pole barn allows for covered parking for equipment, tools, vehicles, & boats. Raise your animals, plant your garden, bring your toys! Plenty of room on the East side of the property to build a larger home with its own gate and driveway already in place. Only 5 miles to the North Entrance to Myakka State Park, 13 miles to I-75, Shopping & Restaurants, 16 miles to Waterside at Lakewood Ranch, 19 miles to Downtown Sarasota, 22 miles to Lido Beach and 25 miles to the famous Siesta Key! Schedule your showing today and come see this cabin in the midst of raw beauty of wild and rare acreage.
Listing is courtesy of: ROSEBAY INTERNATIONAL REALTY, INC (941-366-7673)
Listing Agent: Tina Timmons (941-350-5030)
5883 WHISTLEWOOD CIR, SARASOTA, FL 34232
$485,000202 Days on yellowkey MLS ID: A4671389
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1530 Built: 1979 Tax: $5,067 (2024)Community: Ridgewood Estates 20Th AddSpa: NoSingle Family
Taxes:$5,067
Elementary School: Brentwood Elementary
Remarks: Welcome to 5883 Whistlewood, a centrally located Sarasota retreat, with no HOA, that blends everyday convenience with the best of Florida living. If you’ve been searching for a home that offers a relaxed, coastal lifestyle with quick access to everything Sarasota is known for, this is it. Live just 7.5 miles from downtown Sarasota, where world-class dining, shopping, and entertainment await. Enjoy easy evenings at spots like Ocean Prime, weekend strolls along the Bayfront, or spur-of-the-moment outings to the Farmers Market. When you’re craving beach time, Siesta Key, consistently ranked America’s #1 beach, is only 7 miles away, making sunrise walks, sunset sessions, and full beach days part of your weekly routine. Back at home, unwind in your private swimming pool or relax in the screened-in lanai overlooking a fully fenced backyard, perfect for pets, play, and peaceful afternoons outdoors. Inside, the home offers 4 bedrooms, giving you the flexibility to create guest space, a home office, or a hobby room. The location is ideal for those who value both privacy and connectivity. The neighborhood is quiet and established, yet you’re only 0.8 miles from I-75, making commutes smooth and travel effortless. Outdoor enthusiasts will love being just 2 miles from Urfer Family Park, with walking trails, playgrounds, and green space to enjoy year-round. Whether you’re looking for a primary residence, a seasonal escape, or a property that balances lifestyle with convenience, 5883 Whistlewood delivers a truly complete Sarasota experience, pool days, beach weekends, downtown nights, and a peaceful home base in the heart of town.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Traci Bolen (941-914-5159)
132 TALL TREES CT, SARASOTA, FL 34232
$520,00053 Days on yellowkey MLS ID: A4689367
REDUCED by $10,000 (1.9%) on 05/08/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1865 Built: 2001Monthly Fee: $199 Tax: $3,522 (2025)Community: Oak Court Ph 2-A & 2-BSpa: YesSingle Family
Taxes:$3,522
Elementary School: Fruitville Elementary
Remarks: Located in Oak Court, a gated community of approximately 60+ homes just off Fruitville Road, this updated, west-facing, single-story residence offers convenient access to downtown Sarasota, University Town Center (UTC), Gulf beaches, golf courses, parks, and I-75. Set on a private dead-end street with mature canopy trees and landscaped surroundings. Extensive upgrades include roof (2021), AC (2025), and water heater (2026). Interior features professionally curated paint selections and 24-inch tile flooring (2025) in select areas including two bedrooms and foyer. The layout offers a flexible front room off the entry, ideal for dining, sitting, or office use. The home then opens into the main living area with vaulted ceilings and an open connection to the kitchen. A separate dining area is positioned just off the kitchen, creating a natural flow for everyday living and entertaining. The living space provides direct access to the screened lanai and hot tub, which conveys with the sale. Kitchen features a Samsung appliance suite (2025), soft-close cabinetry, pull-out drawers, island workspace, and adjacent dining area. Bathrooms updated with Calcutta wall tile and energy-efficient commodes (2025). Primary suite includes dual sinks, walk-in shower, and walk-in closet. Secondary bedrooms offer built-in storage and custom paint finishes. Smart home features include Eufy video doorbell and upgraded digital AC thermostat. Additional interior improvements include plantation shutters, vertical blinds, updated lighting fixtures, and ceiling fans. Garage includes epoxy-coated floor (Galaxy Blue, 2025), custom overhead storage, and fresh interior paint. Exterior upgrades include backyard privacy landscaping with Areca palms (2025) and redesigned irrigation system. Community amenities include pool, cabana, lake with fountain, and irrigation.
Listing is courtesy of: MANGROVE REALTY ASSOCIATES (941-957-0080)
Listing Agent: Antonio Lopez (626-664-5124)
2118 DODGE AVE, SARASOTA, FL 34234
$185,000124 Days on yellowkey MLS ID: A4680017
REDUCED by $26,000 (12.3%) on 05/08/2026
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1339 Built: 1956 Tax: $2,800 (2025)Community: Leisure LakesSingle Family
Taxes:$2,800
Elementary School: Emma E. Booker Elementary
Remarks: Do you need more rooms, a fenced back yard, a screen porch and covered parking that doesn't cost a lot? This is it! Home has Living room, updated kitchen & bath, family room, Florida room, storage room. Close to baseball stadium, public park and playground. Are you handy or have contacts for fixing? Yeah, that works. Call your agent today to set up an appointment to see this diamond in the ruff. Due to condition, the property may have health/safety risk(s). Prior to entry / access, all parties must sign a Hold Harmless Form, and the property may only be shown by appointment. This property may qualify for Seller Financing (Vendee). If property was built prior to 1978, Lead Based Paint Potentially Exists.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-758-7777)
Listing Agent: Debbie Roth (941-713-0522)
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