South Sarasota, FL Homes for Sale

**BRILLIANTLY UPDATED and METICULOUSLY MAINTAINED ESTATE in OYSTER BAY, a Coveted, West of Trail Neighborhood** Situated on a large CORNER LOT, this 4-BED, 3 FULL and 1 HALF BATH residence is being Sold FURNISHED and offers desired privacy and extensive updates. Attention to detail is evident throughout this warm contemporary home featuring an open floorplan and unobstructed views of the

Mark Lyda GENEROUS PROPERTY

One or more photo(s) has been virtually staged. Located West-of-Trail in one of Sarasota’s sought-after neighborhoods, Oyster Bay Estates, this stunning waterfront home is designed for those who appreciate breathtaking views and effortless entertaining. With a prime position on Sarasota Bay, this gated estate captures panoramic vistas of the city skyline, preserve and mangrove islands, and

Joel Schemmel DOUGLAS ELLIMAN

Under Construction. Estimated Completion July 2026. Step into the pinnacle of modern luxury with this stunning home located in the prestigious Oyster Bay Estates built by The Holliday Group. Nestled on a generous 18,991 sq ft lot with 71 feet of serene lake frontage, this modern oasis offers a blend of style, comfort, and sophistication. This home is not located in a flood zone and everything is

Ryan Carson RE/MAX ALLIANCE GROUP

A residence of sophistication and luxury, this exceptional home was thoughtfully designed to bring family and friends together—sharing good food, meaningful connection, and the enjoyment of elevated everyday living. Ideally located just 8 miles from Sarasota-Bradenton International Airport, 12 minutes to Siesta Key Beach, and 10 minutes to downtown Sarasota, the property is in close proximity to

Bridget Spiess PREFERRED SHORE LLC

Located in the sought-after West of Trail neighborhood of Oyster Bay Estates, this beautifully updated residence sits on nearly one-third of an acre just around the corner from the historic Field Club. The home blends timeless architectural character with extensive recent improvements, creating a refined yet relaxed retreat close to Sarasota’s most desirable destinations.A beautifully

Michael Hays MICHAEL SAUNDERS & COMPANY

Perched on a remarkable one-acre waterfront parcel along South Lake Shore Drive, this architecturally distinctive residence—designed by Twitchell & Associates—offers a rare opportunity to own a modern Sarasota home with an extraordinary 231 feet of Intracoastal Waterway frontage. The property presents a compelling blend of architectural character, generous scale, and sweeping water views, all

Nikki Taylor DOUGLAS ELLIMAN

OWNER MOTIVATED LOOKING FOR OFFERS! Positioned in highly desirable Oyster Bay Estates in the West of Trail area, this beautifully rebuilt 4-bedroom, 3.5-bath home sits on a high-and-dry spacious 1/3-acre lot in flood zone X where no flood insurance is required. Completely gutted and reconstructed to the highest standards in 2021 this residence is like new. This remarkable property includes a

Carolyn Donnelly COLDWELL BANKER REALTY

Perfectly positioned on a spacious, private lot in the prestigious and highly sought-after Oyster Bay Estates community, the residence embodies exceptional design, architectural intention, and refined livability. Custom designed and built by distinguished, award-winning Platinum Coast Construction and completed in 2021, this 4-bedroom / 4 full & 2 half bath modern masterpiece was crafted with

Ryan Ackerman COLDWELL BANKER REALTY

This Oyster Bay residence with well known address of “North Lakeshore Dr.”....West of trail perfect location.....close to Siesta Key and the activities and also near the renowned “Field Club”. The grand entrance is deserving of the compliments you will receive from friends and family. This 4 bed 3.5 bath with 3613 square foot of living area is perfect with all the amenities. This residence is

Keith Groesbeck MS REALTY MICKEY SCHWEITZER & ASSOCIATES LLC

Welcome to Villa Meraviglia - A Home Beyond Imagination. An extraordinary Neo-Classical Italian Renaissance Estate set on 1.22 bayfront acres in Sarasota’s exclusive Oyster Bay Estates. Featuring 146 feet of pristine, direct frontage along the sparkling waters of Little Sarasota Bay, where sweeping panoramic views unfold, this walled and gated estate feels like a grand villa on the shores of Lake

Dianne Anderson COMPASS FLORIDA LLC

Welcome to this stunning, fully reimagined residence in one of Sarasota’s most sought-after neighborhoods West of the Trail. Comprehensive back to studs renovation with an effective build date to Florida building codes of 2020. No detail has been overlooked in this comprehensive luxury renovation, offering the perfect blend of timeless coastal elegance and modern sophistication. This home is

Albert Joerger KW COASTAL LIVING III

One or more photo(s) has been virtually staged. Experience luxury West-of-Trail living in Sarasota’s coveted Oyster Bay neighborhood. This newly built 2026 custom residence offers 5 bedrooms, 5 full and 2 half baths—all on one thoughtfully designed living level—featuring 4,545 sq. ft. under air and 5,689 sq. ft. total. Set on an impressive 130' x 150' corner lot (0.45 acres), the home is

Ryan Ackerman COLDWELL BANKER REALTY

The Windemere II is an extraordinary luxury custom home meticulously crafted by Heritage Builders. This coastal contemporary residence with clean lines is situated on a very rare West-of-Trail lakefront estate home site. The exquisite two-level residence redefines custom home living, flawlessly blending elegance, sophistication and comfort. As you step in the grand foyer, you are greeted by an

Sara Boudarga HB REALTY GROUP INC.