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4431 Camino Real, Sarasota
$4,225,000
4 Beds ⋅ 5 Baths ⋅ Oyster Bay Estates SubDv. ⋅ 34231 Zip Code
Move in Ready New Construction on Prime Lakefront Lot in exclusive Oyster Bay Estates. Welcome to modern luxury living, safely outside the flood zone and offering a refined alternative to barrier island life. This brand-new contemporary masterpiece combines striking architectural design with uncompromising quality construction. Built with solid block construction, impact windows, and dramatic 10-foot impact sliders throughout, this home delivers both beauty and peace of mind. Step inside through the beautiful Mahogany front door to soaring ceilings up to 21 feet and wide-plank French oak flooring that flows throughout the light-filled living spaces. The gourmet kitchen is a chef’s dream, featuring a Thermador Professional Series appliance package with a dual-fuel gas range, plus an oversized island perfect for entertaining and everyday gathering. The thoughtful split floor plan offers 4 bedrooms, 4.5 bathrooms, and a versatile den — ideal for privacy and flexible living. From the moment you walk in, the sparkling lake and resort-style pool take center stage, setting the tone for effortless Florida living. Enjoy alfresco dining and relaxing evenings in the covered outdoor kitchen and seating area overlooking the water. Additional highlights include an oversized 3-car side-load garage, full irrigation system, and a whole-house generator for added convenience and security. Energy-efficient features include Icynene spray foam insulation and a multi-zone HVAC system with advanced filtration — smart, sustainable comfort year-round. Ideally situated in a top-rated school district, this exceptional home offers the perfect blend of luxury, convenience, and safety. Close to the award winning beaches of Siesta Key without all the day to day traffic and also easy access to downtown. Come experience Sarasota living at its finest.

4431 Camino Real, Sarasota
1815 S Lake Shore Drive, Sarasota
$4,100,000
5 Beds ⋅ 5 Baths ⋅ Oyster Bay Estates SubDv. ⋅ 34231 Zip Code
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.

1815 S Lake Shore Drive, Sarasota
4439 Westwood Lane, Sarasota
$2,768,500
4 Beds ⋅ 4 Baths ⋅ Oyster Bay Estates SubDv. ⋅ 34231 Zip Code
**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**

4439 Westwood Lane, Sarasota
1801 Field Road, Sarasota
$2,550,000
3 Beds ⋅ 5 Baths ⋅ Oyster Bay Estates SubDv. ⋅ 34231 Zip Code
Construction now complete! Prepare to be impressed with artful expressions of design, beautifully tailored interiors and an open brightness filling the home and welcoming you to further explore the many subtle nuances and brilliant examples of excellence in craftsmanship. The talented team at Allegra Homes are experts at designing and building quality state-of-the-art homes with the best of family living in mind. Founder Rob Allegra brings over three decades of experience and skill in building hundreds of incredible residences in some of Sarasota’s most elite locations. 1801 Field Road is no exception. This new construction move in ready beauty is located on over 1/3-acre in prestigious Oyster Bay Estates and just a short distance from the iconic Field Club, one of Sarasota’s oldest by-invitation-only social clubs. This coveted location near the exciting downtown scene gives you easy access to just about anything you could desire. With open living spaces, contemporary architecture and designer touches, the 3,035-square-foot “Kristi Ann” with its extended outdoor living area is destined to become another top choice among today’s buyer who wants it all. Desirable highlights include a generous family room with entertainment/fireplace wall and triple sliders opening wide to the pool area, a dazzling island kitchen with premium amenities second to none, a dining room with built-in buffet and private patio, a deluxe primary suite with an exquisite jewel-like bath and enormous walk-in closet, 2 additional en suite bedrooms, a study with wall of built-ins, a large covered lanai, bonus room with bath opens on 2 sides to the covered poolside living area with full kitchen, 3-car garage with epoxy floor, and a wonderful heated pool/spa with screen enclosure in a gorgeous tropical setting conducive to precious moments with those you love. Other honorable mentions: 10-foot ceilings throughout, tray ceilings in great room/primary suite/study, professionally landscaped with irrigation well, brick paver walk and driveway, impact windows and sliding glass doors, cove or crown molding, concrete tile roof, tankless gas water heater, recessed lighting, pool and house alarm, and 4 natural gas drops (cooktop, grill, water heater, pool heater). Discover a new standard in luxury living. Relax knowing your most important asset is a well-deserved investment and a place to raise a family, pursue your passions and live life to the fullest.

1801 Field Road, Sarasota
1705 Field Road, Sarasota
$2,125,000
4 Beds ⋅ 5 Baths ⋅ Oyster Bay Estates SubDv. ⋅ 34231 Zip Code
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.

1705 Field Road, Sarasota
1717 Field Road, Sarasota
$1,950,000
4 Beds ⋅ 4 Baths ⋅ Oyster Bay Estates SubDv. ⋅ 34231 Zip Code
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 newly-built 484 sq ft detached guest house/ADU with private entrance. Lush, mature landscaping provides privacy and curb appeal to this lovely home. Relaxing Florida living is ensured with a covered luxury outdoor living space including an outdoor kitchen with grill, cooktop, refrigerator and sink ideal for entertaining and family life. Also part of the outdoor living space is the inviting heated saltwater pool and spa with travertine tile deck and new pool cage. The new open-concept kitchen boasts Dekton countertops, a light-wood island with built-in drawers, a gas range and closet pantry. All the bedrooms include ensuite bathrooms. The primary suite offers a custom walk-in closet and spa-style bath with dual vanities, quartz countertops, large walk-in shower, and Toto water closet. The A/C system was replaced in 2025 and provides individual thermostats in each bedroom for comfort. Other new features include wood-look tile flooring throughout, impact windows and doors, new roof, replaced PVC plumbing drains, updated electrical with new panel, sprayed insulation, smooth finished walls & ceilings, tankless water heater, natural gas hookup, new well and irrigation system, and $100,000 in upgraded landscaping. The oversized 2-car garage features epoxy flooring and an impact garage door. Surveillance cameras and security lighting is included for your well-being. Set back from the road, this home offers a quiet and private ambiance. Residents in Oyster Bay enjoy walking through the lovely treed neighborhood and biking to tennis, dining & the marina at the Field Club, and to Red Rock Park and Siesta Key. The home is in an excellent location just minutes to Siesta Key beach, Southside Village and downtown Sarasota, and walking distance to schools, Trader Joe’s, Publix, restaurants, and cafes. This is a fabulous opportunity!

1717 Field Road, Sarasota
1514 S Lake Shore Drive, Sarasota
$1,800,000
3 Beds ⋅ 3 Baths ⋅ Oyster Bay Estates SubDv. ⋅ 34231 Zip Code
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.

1514 S Lake Shore Drive, Sarasota
1643 S Lakeshore Drive, Sarasota
$1,775,000
Oyster Bay Estates SubDv. ⋅ 34231 Zip Code
The property in question is a large, vacant, and meticulously landscaped lot situated on the mainland of Sarasota. This exceptional lot offers western views over a serene lake, providing an idyllic setting for luxury home development. Importantly, the property is located in "X" a non-flood zone, ensuring peace of mind and added value for future homeowners. Key features of the property include: • Location: West of the Trail, Sarasota. (Oyster Bay Estates). • Views: Western views over a beautiful lake • Condition: Vacant, Cleared and landscaped • Safety: Situated in a non-flood zone This large lot represents a rare opportunity to develop a luxury home in one of Sarasota's most desirable neighborhoods. The combination of its prime location, serene views, and secure setting makes it an ideal investment for discerning builders and developers.

1643 S Lakeshore Drive, Sarasota
2551 Wilkinson Road, Sarasota
$360,000
3 Beds ⋅ 3 Baths ⋅ Oyster Bay Estates SubDv. ⋅ 34231 Zip Code
Virtually Staged. A Piece of Sarasota History Meets Modern Opportunity: The "Siesta Key Style" Duplex with TWO separate electrical panels! Own a landmark piece of Sarasota history. Nestled on an expansive, wooded lot at the western end of Wilkinson Road, this "Siesta Key style" bungalow offers a rare blend of timeless character and modern updates. Surrounded by a lush, quarter-acre canopy of mature bamboo, majestic oaks, and tropical palms, this property is a private sanctuary just minutes from the best of the Gulf Coast. Two units, endless potential and fully remodeled between 2023 and 2024, this versatile duplex is an ideal setup for savvy investors, multi-generational families, or those looking to "house-hack". Unit 1: A spacious 2-bedroom, 2-bathroom layout. Unit 2: A charming 1-bedroom, 1-bathroom retreat. Modern Upgrades & Peace of Mind: Every major system has been addressed so you can enjoy "turn-key" living or immediate rental income. Roof: New commercial-grade TPO membrane roof (2022) with a 30-year life. Climate: Brand new, energy-efficient mini-split AC systems in both units. Infrastructure: New plumbing throughout and separate electrical panels for each side. Interior: A fresh mix of new and restored flooring, newer appliances in unit 1, and stylish finishes. Exterior: Extra storage in the outdoor shed and plenty of room to roam & garden on the oversized lot. Location is Everything!!! Whether you’re heading to the beach, to work or to the city, you are perfectly positioned: 5 Minutes to the North Siesta Key Bridge. 12 Minutes to the vibrant culture and dining in Downtown Sarasota. 11 Minutes to the freeway for easy commuting. Don't miss this rare chance to own a functional, fully updated landmark in one of Sarasota’s most convenient locations. Some photos are visually staged. Schedule your private tour today!

2551 Wilkinson Road, Sarasota