101 Osprey Point Drive, OSPREY, FL 34229-9248
- $4,790,000MLS® # A4694716
- 4 Bedrooms
- 6 Bathrooms
- 5,087 SQ. Feet
- 1985 Year Built
Lakefront living and elevated architecture come together at 101 Osprey Point Drive, a Bo MacEwen-designed estate privately positioned on nearly an acre within the gates of Sarasota’s prestigious Oaks Bayside community. Spanning more than 5,000 square feet across two of the community’s most desirable homesites with 150 feet of water frontage, the residence blends timeless architecture, exceptional entertaining spaces, and a tranquil resort-style setting surrounded by lush landscaping and sweeping water views. An oversized granite-tiled circular drive and stately double-door entrance create a memorable arrival, leading into interiors defined by soaring ceilings, white onyx flooring with marble inlays, handcrafted millwork, dramatic fireplaces, crystal chandeliers, and walls of French doors opening to the lakefront terrace and pool. Designed for both elegant entertaining and everyday comfort, the home offers a series of richly detailed gathering spaces including a formal living room with dual fireplaces, a lakefront dining room with custom built-ins, a domed-ceiling sitting room ideal for cocktails or conversation, and a custom bar and wine room with etched-glass cabinetry, stone countertops, and display shelving. The remodeled chef’s kitchen combines classic design with modern functionality, featuring UltraKraft cabinetry, custom soffit lighting, Corian countertops, a center island with breakfast bar, and premium appliances including a Sub-Zero refrigerator, Wolf gas cooktop, wall oven, warming drawer, microwave, dual KitchenAid dishwashers, and wine refrigerator. A butler’s pantry and sunlit breakfast nook overlooking the gardens further enhance the home’s livability. The primary suite serves as a private retreat with a spacious sitting area, custom closets, and a spa-inspired bathroom renovated in 2025. Three additional guest suites with updated baths provide comfort and flexibility, including a separate suite ideally positioned for extended-stay guests, live-in assistance, or multigenerational living. Outdoor living is centered around an open-air pool, expansive entertaining deck, and cabana framed by mature landscaping and manicured hedges, creating a private oasis with peaceful lake views. Additional updates include refinished hardwood flooring, updated guest baths, and a Daikin 5-ton HVAC system installed in 2022. Located within The Oaks Club, residents enjoy access to one of Sarasota’s premier private club communities, offering two championship golf courses, tennis and pickleball courts, croquet, a state-of-the-art fitness center and spa, multiple dining venues, and a private community dock on Little Sarasota Bay. Just moments from Sarasota waterfront dining, Siesta Key beaches, and Sarasota/Venice cultural attractions, this distinguished lakefront estate presents an exceptional opportunity within one of the Gulf Coast’s most established luxury communities.
Property
Location
- NeighborhoodAshley Oaks
- Address101 Osprey Point Drive
- CityOSPREY
- StateFL
Size And Restrictions
- Acres0.93
- Lot DescriptionCul-De-Sac, In County, Landscaped
Improvements
- FenceNo
- SprinklerNo
Features
- ViewWater
Market
- Date ListedMay 26th, 2026
- Days On Market84
- Estimated Payment
Interior
Bedrooms And Bathrooms
- Bedrooms4
- Bathrooms6.00
Heating And Cooling
- HeatingCentral, Electric, Zoned
- Air ConditioningCentral Air, Zoned
- FireplaceYes
Interior Features
- AppliancesBar Fridge, Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range Hood, Refrigerator, Washer, Water Filtration System, Water Softener, Wine Refrigerator
- FeaturesBuilt-in Features, Ceiling Fan(s), Chair Rail, Crown Molding, Eating Space In Kitchen, High Ceilings, Primary Bedroom Main Floor, Solid Surface Counters, Stone Counters, Thermostat, Walk-In Closet(s), Wet Bar, Window Treatments
Building
Building Information
- Year Built1985
- RoofTile
Property Features
- Exterior FeaturesFrench Doors, Hurricane Shutters, Irrigation System, Lighting, Private Mailbox
Garage And Parking
- GarageCircular Driveway, Driveway, Garage Door Opener, Garage Faces Side, Off Street
Community
Amenities
- Area AmenitiesClubhouse, Fitness Center, Gated, Handicap Modified, Pool, Recreation Facilities, Security, Tennis Court(s)
Schools
- ElementaryLaurel Nokomis Elementary
- MiddleSarasota Middle
- HighVenice Senior High
Info
- OfficeDOUGLAS ELLIMAN
Map & Directions
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Listing information last updated on August 19th, 2026 at 8:52pm EDT.