Oyster Bay Estates Single Family Homes For Sale in Sarasota - 11 homes

Remarks: 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 expansive, open concept living space that seamlessly integrates the living, dining and kitchen areas. The gourmet kitchen is a chef’s dream, featuring top-of-the-line appliances, custom cabinetry and vast walk-in working pantry. This stunning home boasts four bedrooms, five luxurious baths and two convenient half baths. The primary suite, located on the first level overlooks the sparkling lake and features a designer bathroom private outdoor shower. For those who love to entertain, the Windemere II does not disappoint. Enjoy movie nights in the dedicated media room or host family gatherings in the versatile bonus room. A private study provides tranquil workspace. Ascend via the elegant custom staircase or convenient elevator to the upper level, where you will find two additional en-suite bedrooms, a large bonus room with wet bar and fitness room. Enjoy leisurely moments on the balcony overlooking the serene lake. Step through the massive pocketing sliding glass doors to discover your personal lakefront oasis – a breathtaking outdoor living retreat with a custom pool and spa and a fully equipped outdoor kitchen. Gather around the fire pit, perfect for cozy evenings under the stars. The Windemere II is not just a custom residence; it is a lifestyle. Experience the epitome of high-end-living and schedule a tour today! Floor plan located in attachments.

Listing is courtesy of: HB REALTY GROUP INC. (941-378-3983)

Listing Agent: Sara Boudarga (941-321-6352)

Remarks: 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 The Ringling, Van Wezel, Selby Gardens, Asolo, premier dining and shopping, The Field Club, and the Sarasota Yacht Club—creating a seamless blend of culture, convenience, and coastal lifestyle. Elegant yet warm and approachable, the home blends refined architecture with tropical elements, including stone columns, metal pergolas, concrete textures, and lush landscaping, creating a relaxed oasis unlike any other. A surrounding stucco wall enhances privacy, allowing you to unwind to the soothing sound of a tranquil fountain within a peaceful, secluded setting. The main living spaces were intentionally designed for gathering, featuring bead-board stained ceilings in the family room, formal living room, and dining area. The cook’s kitchen is both striking and highly functional, highlighted by a glazed pressed-tin ceiling, unpolished concrete floors, and views into the kitchen garden through multiple French doors and expansive windows—perfectly suited for both everyday living and entertaining.

Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)

Listing Agent: Bridget Spiess (941-720-6304)

Remarks: One or more photo(s) has been virtually staged. Panoramic Sarasota Bay views, a gated West of Trail setting in Oyster Bay Estates and an exceptional boating lifestyle define this remarkable waterfront residence overlooking the downtown Sarasota skyline and open waters. Blending timeless architectural details with expansive entertaining spaces and resort-inspired living, the home presents a rare opportunity to experience one of Sarasota’s most sought-after waterfront addresses. Brand-new impact-rated windows and doors are scheduled for installation in August/September 2026, further enhancing the property’s long-term value and storm readiness. A grand arrival sets the tone with travertine stairs leading to stately double entry doors framed by an arched transom window. Inside, expansive living and dining spaces are highlighted by intricate coffered ceilings, artisanal millwork, wainscoting-lined hallways and walls of sliding glass doors designed to maximize natural light while showcasing breathtaking water views. A carved stone gas fireplace anchors the main living area, while seamless indoor-outdoor flow enhances the home’s elevated waterfront atmosphere. Designed for both entertaining and everyday living, the chef’s kitchen features an oversized center island with prep sink, granite countertops, custom wood cabinetry and premium Viking® appliances paired with a Sub-Zero® professional refrigerator. A walk-in pantry with custom organization and an adjoining butler’s pantry with beverage cooler, dishwasher drawers and glass-front cabinetry create exceptional functionality for hosting. Breakfast and casual dining spaces are positioned to capture spectacular waterfront and skyline views from nearly every angle. The great room is surrounded by windows framing Sarasota Bay, lush tropical scenery and the downtown Sarasota skyline, while multiple entertaining bars with beverage coolers, prep sinks, dishwasher drawers and granite countertops provide ideal gathering spaces for family and guests. The primary suite serves as a luxurious private retreat featuring windows overlooking the water, a custom sitting area and a spa-inspired bath with travertine finishes, dual vanities, jetted soaking tub, oversized walk-in shower and custom-designed walk-in closet. A dramatic wood staircase leads to four additional en-suite guest bedrooms, each with access to an enormous balcony showcasing stunning downtown and water views. A three-stop elevator provides convenient access throughout all levels of the residence. The ground-level bonus area seamlessly connects to the resort-style pool deck, creating exceptional flexibility for indoor-outdoor waterfront living. Above the garage, a private guest apartment with separate staircase access offers a living area, kitchenette, spacious bedroom, full bath and private balcony, ideal for extended guests or multigenerational living. Additional highlights include hardwood flooring, plantation shutters, crown molding, custom tray and coffered ceilings, a central vacuum system and extensive architectural detailing throughout. Located minutes from Siesta Key, Southside Village and vibrant downtown Sarasota, this extraordinary Sarasota waterfront estate offers a rare combination of luxury bayfront living, boating access, panoramic sunset views and timeless coastal elegance in one of Sarasota’s premier West of Trail neighborhoods.

Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)

Listing Agent: Joel Schemmel (941-587-4894)

Remarks: Under contract-accepting backup offers. Experience refined modern living in this Oyster Bay Estates, stunning five-bedroom, four-and-a-half-bath residence thoughtfully designed and custom built with exceptional craftsmanship, elevated finishes, and sophisticated smart-home technology. Every detail of this home reflects a commitment to quality, comfort, and luxury. The heart of the home is an extraordinary chef's kitchen appointed with top-of-the-line Thermador appliances, custom cabinetry, an expansive island ideal for entertaining, and a striking custom hood. Elegant designer lighting and Emtek hardware compliment the home's extensive custom woodwork, including solid interior doors, crown molding, baseboards, and detailed window casings. Rich hardwood flooring flows throughout the living spaces, enhancing the home's warm yet refined aesthetic. Designed for both entertaining and everyday enjoyment, the home features a temperature-controlled 120-bottle wine cellar with WhisperKool system, a dedicated golf simulator room with Foresight simulator, and multiple thoughtfully designed living spaces. Smart-home technology is seamlessly integrated through a Wicked Smart system, controlling lighting, sound, security, shades, and WiFi, along with a Lutron automated lighting system throughout. The large and private outdoor living spaces are equally impressive, featuring a custom outdoor kitchen with integrated sound system, a resort-style pool and spa with sun shelf, and elegant travertine pool decking, creating the perfect setting for relaxing or entertaining under the Florida sun. Additional highlights include a striking custom solid oak entry door, designer-selected tile throughout, a built-in Elkay water dispenser, two laundry rooms for added convenience, landscape lighting and a spacious three-car garage. A rare opportunity to own a meticulously designed luxury residence where timeless craftsmanship, cutting-edge technology, and exceptional amenities come together in one remarkable Sarasota home.

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)

Listing Agent: Mary Pat Phillips Radford (941-587-9905)

Remarks: 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 landscaped yard and newly added covered front porch with brick pavers create inviting curb appeal and lead to a charming courtyard entry. Inside, the home showcases distinctive craftsmanship and warm architectural details, including Mexican tile floors, natural wood cabinetry and baseboards, exposed ceiling beams, plantation shutters, and hand-crafted clay sconces and pendant lighting. Fresh interior and exterior paint, updated trim, solid-core doors, and impact-rated windows and doors complement the home’s original character while adding modern comfort. The main living spaces flow naturally together, with the kitchen, dining area, and living room opening through walls of glass to the expansive screened lanai. A wood-burning fireplace with carved stone mantel anchors the living room, while a newly detailed tray ceiling adds architectural interest. The kitchen combines artisanal style with high-end functionality, offering custom wood cabinetry, updated countertops, an intricate ceiling detail, and premium appliances including a Sub-Zero refrigerator and Fisher & Paykel dual-fuel range with side-by-side ovens. Privately positioned, the primary suite features vaulted ceilings with exposed wood beams and sliding glass pocket doors that open directly to the pool terrace. Two walk-in closets with newly designed systems lead to the renovated primary bath, which offers dual vanities, private water closets, and a spacious walk-in shower. Two generously sized guest bedrooms provide comfortable accommodations, each with built-in closet systems and beautifully renovated en-suite baths, creating privacy for family and guests within the home’s traditional split floor plan. Outdoor living is designed for both relaxation and entertaining. The screened lanai surrounds a 40-by-14 heated pool framed by stone columns and generous covered seating areas with wood ceilings, while an Ipe wood open deck, fire pit, and lush tropical landscaping create a private backyard sanctuary. Additional improvements include updated plumbing and HVAC throughout, new ductwork and attic insulation, LED lighting, a Sonos sound system in the main living area and covered porch, renovated laundry room with new cabinetry and appliances, epoxy garage flooring, and a propane tankless water heater with gas supplied to the kitchen range and outdoor grill. Ideally located close to shopping, dining, and just minutes from world-renowned Siesta Beach and downtown Sarasota, this Oyster Bay Estates home offers a rare blend of character, privacy, and thoughtful updates in one of Sarasota’s most established neighborhoods.

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)

Listing Agent: Michael Hays (941-376-1826)

Remarks: Under contract-accepting backup offers. Welcome to this stunning, fully reimagined residence in Oyster Bay Estates, one of Sarasota’s most coveted West of the Trail neighborhoods. Renovated down to the studs with an effective build date of 2020, this exceptional home blends timeless coastal elegance with modern sophistication, showcasing the level of craftsmanship and finish quality typically found in five million dollar plus luxury properties. Thoughtfully designed throughout, the home features wide-plank wood flooring, custom millwork, and an open-concept floor plan designed for both everyday living and effortless entertaining. The gourmet kitchen serves as the centerpiece of the home, offering designer cabinetry, quartz countertops, an oversized island, Sub-Zero and Wolf appliances, and luxury Perrin & Rowe fixtures. The residence includes four spacious bedrooms, three full bathrooms, and two half baths, each beautifully finished with premium materials and spa-inspired details. The beachy character continues with an outdoor shower. Major systems and components have all been replaced, including the electrical, plumbing, HVAC systems, roof, siding, and hurricane-impact windows and doors, including the garage door, providing both comfort and peace of mind. Located in Flood Zone X, flood insurance is not required. Privately set back from the street, the property offers a quiet, resort-like setting with lush new tropical landscaping featuring coconut palms, cabbage palms, orchid trees, pitch apple hedges, and bougainvillea to name a few. The outdoor spaces have been completely transformed with shell-finished hardscape, new patios, elegant walkways, and a private irrigation well. Offered fully furnished, this move-in-ready home is ideally located just moments from downtown Sarasota, St. Armands Circle, world-renowned beaches, shopping, dining, top-rated schools, and less than a block from the historic The Field Club. Buyer and Buyer’s Agent to verify all room dimensions.

Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)

Listing Agent: Albert Joerger (941-685-6145)

Remarks: 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 sitting on .46 acre allowing room for activities. The three car climate controlled garage is large enough for some toys. This is a must see to appreciate this fine residence and its many upgrades. Not in a flood zone, top of the line metal roof with additional tie downs for extra strength, generator, well for sprinkling all new impact windows and doors, home was totally rebuilt ground up in 1997. Gas appliances, fireplace and generator.

Listing is courtesy of: MS REALTY MICKEY SCHWEITZER & ASSOCIATES LLC (941-914-2460)

Listing Agent: Keith Groesbeck (941-266-7601)

Remarks: 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 uncompromising detail and a focus on seamless indoor–outdoor living. Inside, a host of elevated finishes creates a sophisticated yet welcoming atmosphere. Level 5 flat-smooth walls, engineered oak hardwood flooring, 8' solid-core and obscure glass interior doors, 10" baseboards, floating vanities in all baths, and Quartz surfaces throughout promote a clean, modern aesthetic. A dramatic 72" glass fireplace anchors the living area, while the gourmet kitchen boasts high-performance appliances including a Thermador push-to-open column refrigerator, column freezer, 24" wine preserver, Bosch dishwasher, Bosch combo oven/microwave, and 36” induction cooktop. The striking 175-bottle wine room with stone wall adds a stunning design focal point for entertainers and collectors alike. The primary suite offers a spa-like retreat with marble finishes, a Wetstyle soaking tub, and an enclosed outdoor garden area with tropical landscaping, wood decking, and a private outdoor shower. Guest suites each feature en-suite baths and access to a serene outdoor spa-like space with lush plantings, decking, and an outdoor tub and shower—creating peaceful, private escapes separate from the main living areas. Designed for true resort-style living, the exterior features a spectacular 18' x 30' pool and spa with a custom waterfall wall, surrounded by tropical landscaping. The fully equipped outdoor kitchen includes a 42” Blaze gas grill, under-counter refrigerator, outdoor sink, and storage drawers. Additional features include hurricane-impact windows, an advanced security system, irrigation system, and a distinctive 2-car garage with wood-look paneling and a stunning mahogany double-door entry with obscure glass. Situated just moments from Siesta Key, downtown Sarasota, and within walking distance of the prestigious Field Club, Oyster Bay Estates is celebrated for its beautiful streetscapes, active social atmosphere, and proximity to the water and premier amenities. This exceptional residence offers luxurious contemporary living in one of Sarasota’s most desirable neighborhoods.

Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)

Listing Agent: Ryan Ackerman, Pa (305-205-7700)

Remarks: 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 surrounded by a lush tropical oasis that provides exceptional privacy. A dramatic two-story foyer with 21’ ceilings and a steel-and-impact-glass entry door welcomes you inside. Engineered oak hardwood flooring, 10” baseboards, and sleek horizontal receptacles enhance the home’s modern architectural aesthetic. The expansive open-concept kitchen and great room are flooded with natural light from ten windows and four 20’ hurricane-impact glass sliders that open to the outdoor living space. The gourmet kitchen is a chef’s dream, offering an 8-seat center island, large walk-in pantry, quartz countertops, and premium appliances including a Bosch 36” natural gas/induction cooktop, 36” Thermador refrigerator column, 24” Thermador freezer column, 24” full-height Thermador wine cooler, Bosch dishwasher, and 30” Bosch oven/microwave combo. Retreat to the luxurious main suite featuring a Wetstyle tub with wood surround, marble accents, and slate and porcelain flooring. Additional highlights include level-5 smooth interior walls, 8’ solid-core and obscure-glass interior doors, a stunning 175-bottle wine room with marble wall and glass enclosure, Samsung pedestal washer & dryer, and an advanced alarm and exterior security lighting system. The outdoor living area is designed for year-round enjoyment with a summer kitchen equipped with a Blaze 42” gas grill, sink, and under-counter refrigerator. A 15’ x 28’ pool and spa with a custom waterfall feature, plus an outdoor shower, complete this private retreat. The property also offers an irrigation system and a spacious 3-car garage. An exceptional opportunity to own a brand-new, luxury single-level home in one of Sarasota’s most desirable West-of-Trail communities.

Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)

Listing Agent: Ryan Ackerman, Pa (305-205-7700)

Remarks: Under Construction. Estimated Completion July 2026. You have to see this one in person to understand. Prestigious Oyster Bay Estates Modern design 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 on one level (no walking up or down stairs). This residence offers a fantastic alternative to barrier island living, with close proximity to award-winning beaches without the hustle and bustle of island traffic. Designed with durability and safety in mind, this home is built to today's hurricane codes, featuring concrete block construction, impact-rated windows and doors and a 26KW LP gas generator to ensure comfort and piece of mind during any power outages. KEY FEATURES • Open-concept floor plan, featuring a state-of-the-art kitchen with Professional Grade Appliances, quartz countertops, custom cabinetry, Super Vaulted ceilings, oversized windows and sliders and a large kitchen island * This space flows seamlessly into the great room and dining area. The generous primary suite is split from the 2 additional en suite bedrooms and a flex room that can also serve as a 4th bedroom suite • Wide Plank Oak flooring through out the home except for the bathrooms *Attached side entry 3-car garage• Incredible outdoor living area includes a saltwater swimming pool and spa, paver decking, and lush landscaping – perfect for entertaining or relaxing by the water. Green Features: • Icynene open spray foam insulation • 16 SEER multi-zone HVAC system with advanced filtration • Energy-efficient gas grill, cooktop, and fireplace. Located in an excellent school district, this home offers the perfect combination of luxury, convenience, safety and Florida living at its finest. Incredible property and neighborhood on a prime oversized lot.

Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)

Listing Agent: Ryan Carson (941-685-2879)

Remarks: **BRILLIANTLY UPDATED and METICULOUSLY MAINTAINED ESTATE in OYSTER BAY, a Coveted, West of Trail Neighborhood** Situated on a large CORNER LOT, this 4-BED, 3 FULL and 1 HALF BATH residence is being Sold FURNISHED and offers desired privacy and extensive updates. Attention to detail is evident throughout this warm contemporary home featuring an open floorplan and unobstructed views of the Courtyard, Pool & Spa and Garden. For the culinary enthusiast, the impressive Kitchen boasts premium brand appliances including Subzero, Miele and Wolf. Enjoy the warmth of the wood-burning fireplace in the adjacent family room. Flexible Owner’s Suite with either Second or First-Floor possibilities. The second-story primary suite features a balcony overlooking the courtyard and pool, Multiple Walk-In Closets, beautifully update primary bath with dual vanities, custom-tiled shower, soaking tub, etc. In addition to the two guest bedrooms on the first floor, an additional room can also function as a spacious primary bedroom suite with an adjacent, updated Full Bath. NEW HVAC, WASHER & DRYER; WHOLE HOME GENERATOR (2021); NEWER ROOF (2017); HURRICANE IMPACT WINDOWS/DOORS (2018), ETC. Excellent location with easy access to lifestyle amenities — just a half mile to The Field Club… and in close proximity to Southside Village, Sarasota Memorial Hospital, Shopping Centers and Area Beaches including #1 Rated Siesta Key Beach. **Please Enjoy Viewing the 3D Virtual Tour and Aerial Video**

Listing is courtesy of: GENEROUS PROPERTY (941-275-9399)

Listing Agent: Mark Lyda (941-586-2670)