Location: Sarasota
Keyword(s): Booker High
Keyword(s) High School: Booker High
Do Not Show Listings
3350 W CHELMSFORD CT #13, SARASOTA, FL 34235
$363,00088 Days on yellowkey MLS ID: TB8466391
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1513 Built: 1990 Tax: $2,699 (2025)Community: Chelmsford CloseVilla
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,699
Elementary School: Gocio Elementary
High School: Booker High
Tax Year: 2025
Middle School: Booker Middle
Remarks: Located in the desirable Chelmsford Close enclave of The Meadows, this well-maintained and freshly painted 2 bedroom, 2 bathroom villa with a 2-car garage offers over 1,500 square feet of comfortable living space and golf course frontage with peaceful fairway views. Built in 1990 and carefully cared for by the original owners, the home enjoys a prime setting close to the community pool and is surrounded by mature landscaping and manicured grounds. Chelmsford Close is known as one of the newer villa communities in The Meadows, featuring solid construction, attractive architecture and a quiet, private feel. Residents enjoy a park-like setting within a 1,600-acre master-planned community offering 14+ miles of walking and biking trails, lakes, green spaces, fitness facilities, pickleball and optional golf and tennis memberships. Ideally situated near Nathan Benderson Park, University Town Center shopping and dining, and just minutes to downtown Sarasota, cultural attractions and world-class Gulf beaches. Competitively priced, this villa presents an excellent opportunity to enjoy the Sarasota lifestyle—schedule your private showing today before it’s gone!
Listing is courtesy of: SMITH & ASSOCIATES REAL ESTATE (813-839-3800)
Listing Agent: Tyler Gilley (847-347-4734)
3410 CHELMSFORD CT #3, SARASOTA, FL 34235
$417,50030 Days on yellowkey MLS ID: A4686671
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1649 Built: 1991 Tax: $2,746 (2025)Community: Chelmsford CloseVilla
Taxes:$2,746
Remarks: Enjoy sweeping golf course and lake views from this inviting 2BR/2BA + den villa with a 2-car garage and charming courtyard entry. The open living area flows seamlessly to an air-conditioned enclosed lanai, creating an airy, expanded space ideal for both relaxing and entertaining. A light-filled kitchen features a breakfast nook, solid- surface counters, stainless appliances, soft-close drawers, and convenient pull-out shelving. The primary suite is a peaceful retreat with scenic views, a spacious walk-in closet, and a tiled walk-in shower with a separate dressing area. A split-bedroom layout provides privacy for guests. Neutral tile flooring and classic plantation shutters add style and continuity throughout the home. A community pool is just steps away. Located within The Meadows, tropical resort-style setting, where residents enjoy miles of scenic trails, a fitness center, a Junior Olympic pool, pickleball, dining, golf, and a premier tennis complex with Har-Tru courts. Just minutes to UTC, Whole Foods, Fresh Market, Nathan Benderson Park, and a short drive to Sarasota’s award-winning beaches, arts, and culture—offering the very best of the Florida lifestyle.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Marci Mcfarland (941-961-3390)
3856 27TH PKWY, SARASOTA, FL 34235
$339,00063 Days on yellowkey MLS ID: A4682653
1 Days Off yellowkey (back on 3/30/2026)
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 1014 Built: 1960 Tax: $1,218 (2025)Community: Kensington ParkSingle Family
Taxes:$1,218
Remarks: Under contract-accepting backup offers. Wonderful opportunity to live in Kensington Park. This 2 bedroom 1.5 bath block home is nicely situated on a well established lot with mature Oak trees and Mature fruit trees. The kitchen has been completely redone with quartz counters, luxury vinyl flooring and solid wood cabinets. New Roof in 2020, new hot water heater 2022, updated kitchen and bath 2022, New Hvac 2023. House has been repiped in 2014 and cast iron replaced in 2023. Nice 8'x12' shed in the back.Easy access to the beach and shops.
Listing is courtesy of: SHIRLEY INTERNATIONAL REALTY (941-448-4872)
Listing Agent: David Barkema (941-284-4858)
2616 WATERFRONT CIR, SARASOTA, FL 34240
$1,274,00021 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
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)
2439 FEIFFER CIR, SARASOTA, FL 34235
$350,00072 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
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)
17001 DEER PRAIRIE DR, SARASOTA, FL 34240
$2,000,00036 Days on yellowkey MLS ID: A4684995
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)
724 CROSSWIND AVE, SARASOTA, FL 34240
$1,595,000103 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.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-907-9541)
Listing Agent: Charles Totonis (941-524-8299)
3225 RAMBLEWOOD DR, SARASOTA, FL 34237
$160,00093 Days on yellowkey MLS ID: A4678479
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1343 Built: 1974Monthly Fee: $702 Tax: $2,970 (2025)Community: Ramblewood AcresTownhouse
Taxes:$2,970
Elementary School: Tuttle Elementary
Remarks: Experience the epitome of maintenance-free living in the heart of Florida at Ramblewood Acres, a fantastic, gated community offering an array of luxurious amenities. Nestled in a vibrant, friendly neighborhood, this community features beautifully designed townhouses and villas surrounded by lush landscaping and mature trees. This meticulously renovated home boasts modern elegance throughout. As you step inside the charming kitchen, it invites you in to prepare your next meal. Featuring gleaming granite countertops, neutral cabinetry, and high-end stainless steel appliances it is truly a chef's delight. The attention to detail extends to the freshly painted interiors in the open-concept living and dining area where you can gather during the holidays. The spacious layout includes three full bedrooms upstairs, providing plenty of space for family and sleepover guests. The primary bedroom serves as a serene retreat after a long day, featuring direct access to a private wood deck through sliding glass doors—an ideal spot to unwind and watch the sunset. This tranquil space also includes an attached en-suite bathroom and double closets, providing ample storage for all your needs. Additional conveniences include an in-unit laundry area, a rare outside storage room that is unique to this complex, and parking is a breeze with two dedicated spaces! Residents of Ramblewood Acres enjoy access to three sparkling swimming pools, perfect for cooling off on warm Florida days. Stay active with the on-site tennis courts and playground, or gather with friends and neighbors at the expansive clubhouse, which includes a state-of-the-art fitness center, a billiards room, a fully equipped kitchen and dining area, a well-stocked library, and a large gathering room ideal for social events. Conveniently located in the heart of Sarasota, this community is just minutes away from world-renowned beaches, the Oriole Spring Training ballpark, and popular shopping and dining activities in the vibrant downtown area. Do not miss out on this opportunity, call today to schedule a private tour before it's gone!
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Joey Lamielle (941-350-0016)
3732 SURREY LN, SARASOTA, FL 34235
$524,000108 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)
9272 MCDANIEL LN, SARASOTA, FL 34240
$1,995,00086 Days on yellowkey MLS ID: A4677312
0 Days Off yellowkey (back on 3/30/2026)
Bed: 3 Bath: 3.5 Liv Area Sq Ft: 2860 Built: 2020Monthly Fee: $499 Tax: $18,246 (2025)Community: Founders ClubSingle Family
Taxes:$18,246
Remarks: Under contract-accepting backup offers. Welcome to an exceptional turnkey furnished retreat in the exclusive Founders Club, where refined luxury meets serene Florida living. This impeccably maintained former London Bay model residence offers timeless design enhanced by contemporary upgrades. Set against a tranquil preserve backdrop the home enjoys privacy and picturesque natural views. Striking curb appeal and manicured landscaping introduce a thoughtfully designed contemporary interior with a desirable open floor plan. Elegant finishes include porcelain wood-look plank tile flooring, tall baseboards, detailed ceilings, and curated designer lighting throughout. The expansive great room is highlighted by a modern beam ceiling, custom textured feature wall, designer window treatments, and center opening impact sliding glass doors that seamlessly connect indoor and outdoor living. Entertain effortlessly on the paver lanai featuring a spacious covered area, fully equipped outdoor kitchen with grill and beverage refrigerator, and a sparkling saltwater pool and spa complete with sun shelf and mosaic tile accents. The lushly landscaped backyard, enhanced by ambient lighting, creates a stunning setting for relaxing. At the heart of the home, the contemporary kitchen offers generous gathering space around a large central island and showcases pristine model level finishes. Highlights include high end stainless steel appliance suite with gas cooktop, modern cabinetry with pot and pan drawers, quartz countertops, full height backsplash, walk in pantry, coffered ceiling detail, and designer pendant lighting. The open dining area features a statement chandelier and a stylish dry bar with glass shelving, wine refrigerator, and subway tile backsplash. The grand primary suite is a private sanctuary overlooking the lanai and preserve, offering custom dual walk-in closets. The spa-inspired primary bath features dual vanities, a freestanding soaking tub, and an expansive walk-in shower with frameless glass and custom pebble tile flooring. A versatile den with closet provides flexibility as a home office or additional bedroom, complemented by a nearby powder bath. Two guest suites are thoughtfully positioned to provide privacy, each offering a spacious closet and en-suite bathroom. Additional features include an air-conditioned three-car garage with epoxy flooring, custom cabinetry, and electric vehicle charger. The Founders Club offers an unparalleled lifestyle surrounded by 700 acres of natural Florida beauty. With just 262 homesites, this low-density enclave is designed for privacy and serenity. Residents enjoy access to a recreation center offering yoga and pilates classes, as well as Har-Tru tennis courts, pickleball, basketball, sand volleyball, and a kid's playground. Membership at the Founders Golf Club is optional offering both golf and social memberships. The renowned Robert Trent Jones Jr. golf course offers members easy tee times and is one of the only walkable courses in the region. Members enjoy a a grand Southern-style clubhouse, fine dining, a year-round social calendar, and a 24/7 fitness facility. It’s more than a home, it’s a lifestyle curated for those who appreciate understated luxury and quiet prestige. All just minutes from exquisite dining, shopping, and the vibrant art scene of downtown Sarasota, as well as Sarasota's incredible beaches.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Tricia Rudd (941-730-4042)
311 OAK HILL WAY #26, SARASOTA, FL 34232
$225,000167 Days on yellowkey MLS ID: A4669876
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1354 Built: 1985Monthly Fee: $560 Tax: $1,398 (2024)Community: Village Oaks Sec BCondo
Taxes:$1,398
Tax Year: 2024
Remarks: Under contract-accepting backup offers. Beautifully Updated End Unit Villa in Village Oaks! Welcome to this bright and spacious 2-bedroom, 2-bath end-unit villa perfectly situated in the sought-after community of Village Oaks. Featuring vaulted ceilings and an open floor plan, this home exudes warmth and comfort from the moment you enter. The living and dining area, along with both bedrooms, boast stunning engineered hardwood floors that elevate the home’s appeal. Recent upgrades include newer hurricane-impact windows on the west side (with a transferable warranty from Reece Windows) and accordion shutters on all the windows, offering peace of mind during storm season. The A/C system (8 years old) has been consistently serviced under a maintenance contract and features a UV light purification system for improved air quality. The kitchen shines with a new dishwasher (6 months old) and new disposal (1 year old), while a whole-house water filtration system ensures clean, fresh water throughout. Enjoy your morning coffee or evening breeze in the enclosed lanai, overlooking a lush, open green space. The roof was replaced in 2024—fully covered by the HOA, which also handles exterior painting and exterior maintenance. Located just steps from the heated community pool and newly resurfaced tennis courts with pickleball overlays, this villa offers a blend of relaxation and convenience. Village Oaks is beautifully landscaped and centrally located near excellent schools, shopping, restaurants, downtown Sarasota, and world-famous beaches. Come see why this end-unit gem stands out—offering comfort, care, and value in one perfect package! All information provided by the sellers is deemed reliable but is not guaranteed. Buyers are encouraged to verify all information independently.
Listing Agent: Reeny Kaney (941-954-5454)
800 N TAMIAMI TRL #1203, SARASOTA, FL 34236
$1,045,00079 Days on yellowkey MLS ID: A4680471
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1323 Built: 2007 Tax: $14,047 (2025)Community: AlinariCondo
Taxes:$14,047
Elementary School: Alta Vista Elementary
Remarks: Prepare to be wowed. This expansive water-view and renovated residence on the 12th floor delivers breathtaking Sarasota sunsets and tranquil bayfront vistas the moment you step inside. Thoughtfully designed and impeccably maintained, the home is ideally situated within Sarasota’s cultural epicenter—just steps from world-class performing arts, tranquil garden spaces, the waterfront promenade, and The Bay Park’s scenic walking and cycling paths and multitude of activities. The building itself presents a truly elevated lifestyle, featuring an exceptional array of amenities including a resort-style pool and spa, fitness center with sauna, private theater, billiard room, library, club and tea rooms, business center, wine storage, bicycle storage, private storage, and three guest suites. Residents also enjoy the convenience and security of a 24-hour doorman and two deeded parking spaces. Inside the residence, refined updates enhance both form and function. Features include fresh paint, newer interior doors with glass knobs, custom closets, and plantation shutters. The kitchen has been tastefully updated with a reconfigured island showcasing a single-level quartz countertop, new sink, and new appliances installed in December 2024. The spa-inspired primary bath and renovated second bath offer a calming, contemporary aesthetic. Major system updates include a 2019 HVAC and a 2017 water heater, ensuring peace of mind. This is elevated Sarasota living—where sweeping water views, walkable culture, and turnkey luxury come together in one exceptional home.
Listing Agent: Mackenzie Longueuil (941-961-4023)
5667 SHEFFIELD GREENE CIR #59, SARASOTA, FL 34235
$270,000191 Days on yellowkey MLS ID: A4667845
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1099 Built: 1993 Tax: $2,098 (2024)Community: Sheffield GreeneCondo
Taxes:$2,098
Remarks: Welcome to Sheffield Greene in The Meadows! This sought after community is also highlighted by its location and it's close proximity to the University Town Center, a great place to live, play and relax. Sheffield Greene offers resort style living in a community with so much to do. This condo is a ground floor end unit with a living room, dining room, kitchen, kitchen dinette, laundry room, two bedrooms, two bathrooms, an outside storage space and two screened in covered lanais. Also included is a custom designed wall unit in the living room and custom designed unit and desk in the second bedroom, plus hurricane windows, and your own attached single car garage with garage door opener. To cool off on those hot sunny Florida days- enjoy a brief walk to the community pool and lounge area. New Roof 2025, New A/C 2025, New Washer/Dryer 2024, New Dishwasher 2024 and New Water Heater 2022. The Meadows is a large mature resort-style community with numerous lakes, approximately 14 miles of walking and biking trails and so much more. Beyond this lovely home, you'll find premier shopping at The University Town Center Mall (UTC) which has 100+ retailers. You'll also find a variety of events and activities at Nathan Benderson Park (NBP) or perhaps plan to visit the brand new Mote Marine Laboratory & Aquarium. There's a plethora of restaurants for any palette such as, Capital Grille, Seasons 52, Brio, Cheesecake Factory, Yard House, Ford's Garage, Jpan Sushi and other stores like Whole Foods and Trader Joes! Explore Legacy Trail, local beaches like Siesta Key and downtown Sarasota on Main Street. Drive north on IH 75 for Anna Maria Island in Bradenton, Ellenton for the Outlet shopping mall and the Ice and Sports Complex, or St Pete & Tampa. Drive east for Orlando, or head south for Naples, Miami and the Florida Keys. Book your Showing today!
Listing is courtesy of: MEDWAY REALTY (941-375-2456)
Listing Agent: Christine Glassburn (941-545-5658)
2288 MIDNIGHT PEARL DR, SARASOTA, FL 34240
$500,00035 Days on yellowkey MLS ID: A4686184
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1845 Built: 2019Monthly Fee: $147 Tax: $3,659 (2025)Community: Landing Ph 1Single Family
Taxes:$3,659
Remarks: Welcome to this beautifully upgraded 3-bedroom, 2-bathroom home in the highly desirable Bay Landings community of Lakewood Ranch. Thoughtfully designed and meticulously maintained, this residence showcases a variety of custom touches and high-end upgrades throughout. A spacious and welcoming front porch creates a charming first impression and offers the perfect place to relax and enjoy the peaceful neighborhood setting. Inside, the open-concept layout creates a bright and inviting living space that flows effortlessly from the kitchen to the dining and living areas—ideal for both everyday living and entertaining. Positioned on a generous pie-shaped lot, the home enjoys peaceful conservation views that provide privacy and a beautiful natural backdrop. The home has also been freshly painted on both the interior and exterior, giving it a crisp, updated feel from the moment you arrive. Natural light fills the main living space thanks to two skylights installed just two years ago, enhancing the bright and airy atmosphere. The kitchen is a true centerpiece, featuring custom cabinetry, quartz countertops, and a stunning custom double-fan range hood that blends style with functionality. Unique hardware sourced and shipped directly from Morocco adds a distinctive touch that sets this kitchen apart. Both bathrooms continue the theme of quality finishes with granite countertops and upgraded hardware. All three bedrooms feature engineered hardwood flooring for warmth and durability, and each bedroom is equipped with ethernet wiring for reliable connectivity. The spacious primary suite offers a beautiful trey ceiling that adds architectural character, along with a customized walk-in closet system designed with extensive storage and organization in mind. The primary bathroom provides a relaxing retreat with a walk-in shower as well as a separate stand-alone soaking tub. One of the only homes in the neighborhood featuring French doors (from Anderson Windows & Doors), adding both quality craftsmanship and style. The garage has also been upgraded with a sleek epoxy floor that is less than a year old. Step outside to enjoy the expansive backyard, where clusia plants line the perimeter and can grow up to 30 feet tall, creating a natural privacy wall over time. This home offers the perfect blend of thoughtful upgrades, comfort, and location. Just minutes from Waterside, incredible restaurants, the shops at UTC, and some of America’s most beautiful Gulf Coast beaches, you’ll enjoy convenient access to everything that makes the Lakewood Ranch lifestyle so desirable.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Spencer Robinson (941-702-0365)
443 BIRD KEY DR, SARASOTA, FL 34236
$2,275,00037 Days on yellowkey MLS ID: A4686032
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 2676 Built: 1966Monthly Fee: $100 Tax: $23,842 (2025)Community: Bird Key SubSingle Family
Taxes:$23,842
Elementary School: Southside Elementary
Remarks: Poised on the coveted island of Bird Key, just across the graceful span of the John Ringling Causeway Bridge from downtown Sarasota, this striking Mid-Century modern garden home captures the timeless ease of coastal living. This beautifully designed one-level residence offers three bedrooms, three baths, and 2,676 square feet of thoughtfully arranged living space, where clean architectural lines meet warm, inviting finishes. A neutral palette, 18-inch porcelain tile flooring, and dramatic stone accent walls create a sophisticated yet relaxed atmosphere throughout the open floor plan. Multiple seating areas flow naturally from one space to the next, anchored by a charming wood-burning fireplace—perfect for intimate evenings or lively gatherings. A wall of sliding glass doors dissolves the boundary between indoors and out, opening to a private tropical retreat. The heated pool and expansive screened patio are framed by lush landscaping and a comfortable outdoor seating area designed for effortless entertaining, sunset cocktails, and relaxed Florida afternoons. At the heart of the home, the spacious kitchen invites both conversation and culinary creativity. A large island with granite countertops, elegant pendant lighting, stainless steel appliances, and a stylish backsplash makes it equally suited for casual breakfasts or hosting memorable dinners with friends and family. Peace of mind meets modern convenience with hurricane-impact windows and doors throughout the home. Arrival is equally impressive. A circular paver driveway welcomes guests, complemented by beautiful outdoor lighting and a charming courtyard that leads to the front entrance—an inviting prelude to the warmth within. This home is also pet friendly with a fenced back yard area to keep your pooches secure. The neighborhood offers many walking areas and the Bird Key Park, directly across from the Bird Key Guard House entrance, is a wonderful place to enjoy sunset views over Sarasota Bay. Perfectly positioned just moments from the new Bird Key Yacht Club under construction, the boutiques and dining of St. Armands Circle, and the pristine sands of Lido Beach, this residence offers the rare combination of island serenity and vibrant coastal lifestyle. A timeless retreat in one of Sarasota’s most desirable communities—where elegance, comfort, and the gentle Gulf breeze come together beautifully.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Julie Klick (941-780-6001)
5515 DOWNHAM MDWS, SARASOTA, FL 34235
$725,00053 Days on yellowkey MLS ID: A4681324
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 2640 Built: 1992Monthly Fee: $193 Tax: $4,691 (2025)Community: Devonshire PlaceSingle Family
Taxes:$4,691
Remarks: Curb appeal begins at the street with beautifully selected driveway pavers that create an inviting approach and set the stage for what awaits inside. Step through the double-door entry and you are immediately drawn to sweeping views—across the expansive lanai and solar-heated pool and spa, over the tranquil lake that winds through The Meadows, and onward to the lush fairways of the golf course. * * * Offering 3 bedrooms, 2.5 baths, and 2,640 square feet under air, this thoughtfully designed residence provides a comfortable and highly functional layout ideal for both everyday living and entertaining. The primary suite is privately situated apart from the secondary bedrooms, creating a peaceful retreat, while the guest bedrooms at the opposite end of the home offer flexibility and privacy for family or visitors. * * * Multiple living spaces enhance the home’s versatility, including formal living and dining rooms, as well as a spacious great-room style family room that includes a casual dining area just off the kitchen. A striking coral stone fireplace serves as a beautiful focal point in the family room, adding warmth, character, and architectural interest to the space. * * * The kitchen is light and bright, featuring white cabinetry and light gray countertops that create a fresh, timeless feel. Abundant, well-designed cabinetry surrounds the cook, offering exceptional storage and an efficient layout that makes meal preparation both comfortable and convenient. * * * Outdoor living is equally impressive. The large screened lanai, solar-heated pool, and spa provide the perfect backdrop for relaxing afternoons, evening swims, or entertaining friends while taking in picturesque water and golf course views. The seamless indoor-outdoor flow embodies the very best of the Florida lifestyle. * * * Residents of The Meadows enjoy one of Sarasota’s most established and amenity-rich communities, known for its scenic lakes, miles of walking and biking trails, golf and social opportunities, and convenient proximity to University Town Center, I-75, downtown Sarasota, and renowned Gulf Coast beaches. * * * A home that combines generous living spaces, exceptional views, and an outstanding location—an opportunity not to be missed.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Marilyn Kneafsey (941-373-0999)
2170 ROBINHOOD ST #C1406, SARASOTA, FL 34231
$1,095,00068 Days on yellowkey MLS ID: A4681719
0 Days Off yellowkey (back on 2/9/2026)
Bed: 3 Bath: 3.5 Liv Area Sq Ft: 1465 Built: 2026 Tax: $46,289 (2025)Community: Sarasota Bath And Racquet Club, A CondominiumCondo
Taxes:$46,289
Elementary School: Phillippi Shores Elementary
Middle School: Brookside Middle
Remarks: Under Construction. Pre-construction. Experience refined luxury living at Bath & Racquet Residences, where modern elegance meets Sarasota’s storied legacy. This spacious three-bedroom, 2.5-bath residence features floor-to-ceiling windows, custom Italian cabinetry, quartz countertops, premium Bosch appliances, and serene views overlooking the beautifully landscaped courtyard. A separate laundry room is one of the many thoughtful design elements enhancing everyday comfort. Beyond your doorstep, enjoy an unparalleled collection of resort-style amenities. The community and club feature a private pool, expansive two-acre park, dog park, playground, and a scenic 1-kilometer walking trail—perfect for an active outdoor lifestyle. Sports and wellness enthusiasts will appreciate 13 tennis courts, 2 pickleball courts, 4 panel courts, a resort-style club pool, on-site restaurant, state-of-the-art fitness center, and a full-service wellness spa. Located just 4 miles from the world-famous Siesta Key beaches and 3 miles from vibrant Downtown Sarasota, this address offers the perfect blend of luxury, convenience, and coastal sophistication. Bath & Racquet Residences presents a unique opportunity for both full-time residents and investors, with short-term rentals permitted (7-night minimum), offering flexibility and income potential. Under the guidance of Tommy Haas, former World No. 2 and official club ambassador, this iconic redevelopment reimagines the historic Bath & Racquet Club, originally founded in 1969. Once the home court of tennis legends such as Chris Evert and Martina Navratilova, the property now enters a new era—honoring its rich heritage while embracing modern elegance, wellness, and active living. Designed by the acclaimed Halflants + Pichette Architects, Bath & Racquet Residences and Club presents 256 luxury condominiums with low HOA fees.
Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: Cari Miller (203-722-4509)
1275 42ND ST, SARASOTA, FL 34234
$445,000165 Days on yellowkey MLS ID: A4670391
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1328 Built: 1992 Tax: $4,532 (2024)Community: SunnybrookSingle Family
Taxes:$4,532
Remarks: Beautiful Sarasota Home Near Beaches, Shopping & Nightlife. Discover this meticulously maintained 3-bedroom, 2-bath, 2-car garage home ideally located in sunny Sarasota, just minutes from renowned beaches, shopping, dining, and vibrant nightlife. Designed with a desirable split-bedroom floor plan, the home offers a spacious open-concept great room perfect for everyday living and entertaining. Off the kitchen features a generous 5x7 storage closet and a convenient indoor laundry area, providing excellent functionality. Step outside to a large screened-in patio, ideal for relaxing or grilling while enjoying Florida living year-round—without the pests. An air-conditioned work shed offers additional space for storage, hobbies, or projects. Notable upgrades and features include an expanded driveway, attractive low maintenance yard scaping, new plank flooring in the bedrooms (2025), fresh interior paint (2025), hurricane-rated windows and doors, AC serviced in 2025, hot water heater (2019), and new blackout blinds. The roof was replaced in 2014. For added peace of mind, the home also includes an exterior generator plug-in and a Gemma’s GM I 2000ED dual-fuel generator (gas/propane). Conveniently located near Ringling College of Art and Design and New College of Florida, this property offers excellent investment and rental potential. Furniture conveys—home is offered completely furnished. A fantastic rental opportunity is available with this property. It is located in City of Sarasota which has 7 days minimum for rentals. Don’t miss out on this move-in-ready Sarasota home in a prime location!
Listing is courtesy of: CHANNELL REAL ESTATE & INVESTMENTS (941-586-6234)
Listing Agent: Dj Morieko (941-356-4431)
550 46TH ST, SARASOTA, FL 34234
$999,000177 Days on yellowkey MLS ID: A4668768
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 2309 Built: 1940 Tax: $2,995 (2024)Community: Indian Beach Map OfSingle Family
Taxes:$2,995
Elementary School: Bay Haven Sch of Basics Plus Elementary
Remarks: SIGNIFICANT PRICE IMPROVEMENT of over $200,000!! Great opportunity to own over half an acre of land in Indian Beach Sapphire Shores - Must Be Seen in Person. Schedule a viewing today! Tucked beneath a canopy of lush, tropical greenery in iconic Indian Beach, this distinctive family compound on over half an acre captures the spirit of one of Sarasota’s most sought-after and uniquely charming neighborhoods. Blending privacy with everyday ease, the property features two separate driveways on different streets—providing rare accessibility, a true estate presence, and exceptional flexibility. The spacious split-plan residence offers inviting living and dining areas, a primary suite with an accessible en-suite bath, and timeless architectural character throughout. Perfect for multigenerational living **or income-producing opportunities**, the home includes a private mother-in-law apartment with its own entrance, bedroom, bath, walk-in closet, and kitchenette, as well as a second en-suite bedroom with its own exterior access—ideal as a guest suite or potential rental. Multiple carports, an RV port with a 220v outlet for RV or EV charging, and ample room to add a pool enhance the property’s versatility. Located moments from award-winning beaches, Sarasota Bay, Sapphire Shores Park, The Ringling Museum, Sarasota Jungle Gardens, SRQ Airport, and downtown Sarasota, this residence offers an extraordinary opportunity to create your own legacy home.
Listing Agent: Carol-Ann Warr (941-780-0665)
5150 MARSH FIELD LN #120, SARASOTA, FL 34235
$239,000207 Days on yellowkey MLS ID: O6346740
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1444 Built: 1981Monthly Fee: $465 Tax: $2,720 (2024)Community: Heronmere IiCondo
Taxes:$2,720
Remarks: Recently Reduced by $66,000.! Enjoy resort-style living in The Meadows, one of Sarasota's most sought-after communities. This beautifully remodeled 2 bedroom, 2 bath corner unit condo offers light filled livings spaces, sweeping views of lush green spaces, gardens and the pool, plus unforgettable sunsets from the large screened-in balcony framed by a mature Jacaranda tree. The residence features an oversized primary suite with walk-in shower, walk-in and linen closets, and a private split plan layout with the guest bedroom and bath. Recent updates in 2022 include: a new roof, new AC, new kitchen appliances, fresh paint, and waterproof engineered hardwood flooring. Move-in ready with lasting value. The Meadows is a nature-rich Sanctuary with over 1600 acres of mature oaks, walking and biking trails, lakes, ponds, and abundant wildlife. Residents enjoy tennis, pickleball, swimming, golf, fitness club and a welcoming, social atmosphere that feels like home from the moment you arrive. Perfectly located, you are just minutes from the University Town Center Mall's shopping, dining and entertainment, Benderson Park, Whole Foods, Trader Joe's, and Mote Marine Aquarium. I-75 is 5 minutes away for easy access to Tampa, Naples, & St Pete. Sarasota's world-famous beaches, Lido, Longboat, and Siesta Key are all within a quick drive. Sarasota Memorial Hospital’s medical offices, Imaging Services, and Urgent Care Center at University Park are 5 minutes away giving you the best medical care in town. This is your opportunity to experience a vibrant Sarasota lifestyle and own a move-in ready condo in the heart of it all. Schedule your private showing today! Call Associate/Owner Direct, Alina Ruta.
Listing is courtesy of: HOME WISE REALTY GROUP, INC. (407-712-2000)
Listing Agent: Jon Feshan (407-921-8093)
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