101 OSPREY POINT DRIVE, Osprey, FL 34229

• 4 beds |
• 6 baths |
• 5,087 sqft

Property Description

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.

Listing Status:

Active

Date Added:

May 26, 2026

Data Last Updated:

June 28, 2026 at 7:23AM

Listing Office:

DOUGLAS ELLIMAN : 941-867-6199

Listing Agent:

Joel Schemmel : 941-587-4894

MLS ID:

A4694716

Interior

• General: Built-in FeaturesCeiling Fans(s)Chair RailCrown MoldingEat-in KitchenHigh CeilingsPrimary Bedroom Main FloorSolid Surface CountersStone CountersThermostatWalk-In Closet(s)Wet BarWindow Treatments
• Rooms: Breakfast Room SeparateDen/Library/OfficeFamily RoomFormal Dining Room SeparateFormal Living Room Separate
• Appliances: Bar FridgeBuilt-In OvenCooktopDishwasherDisposalDryerElectric Water HeaterMicrowaveRange HoodRefrigeratorWasherWater Filtration SystemWater SoftenerWine Refrigerator
• Laundry: InsideLaundry Room
• Flooring: BrickCeramic TileParquet
• A/C: Central AirZoned
• Heating: CentralElectricZoned
• Fireplace: Family RoomLiving RoomOtherPrimary BedroomWood BurningFireplace

Exterior

• General: French DoorsHurricane ShuttersLightingPrivate MailboxIn Ground
• Style: CustomTraditional
• Other Structures: Front PorchRear Porch
• Pool: GuniteIn Ground
• Parking: Circular DrivewayDrivewayGarage Door OpenerGarage Faces SideOff Street

Construction

• Roofing: Tile
• Windows: BlindsDrapesWindow Treatments
• General: BlockStuccoOneSlab

Location

• Road/Access: AsphaltPaved
• HOA Amenities: ClubhouseFitness CenterGatedHandicap ModifiedPoolRecreation FacilitiesSecurityTennis Court(s)Guard - 24 HourPoolManagementPrivate RoadSecurity5700.0Semi-Annually
• Originating MLS: Stellar MLS
• County: Sarasota

Lot

• Zoning: RSF1LOTS 147 & 148LESS N 30 FT OF LOT 148TOGETHER WITH BEG AT SE COR OF LOT 148 TH N-6-10-38-W 96.8 FT TH N-87-22-15-E 2 FT TH S-6-10- 38-E 191.63 FT TH S-53-22-30-W 167.57 FT TH NWLY ALG CURVE TO RIGHT 31.71 FT TH N-54-13-02-E 181.65 FT TH N-6-10-38-W 62.54 FT TO POBOAKSBEING SAME LANDS AS DESC IN ORI 20221129360142050008
• View: Water

Utilities

• Utilities: BB/HS Internet AvailableCable AvailableElectricity ConnectedPhone AvailablePropanePublicSewer ConnectedSprinkler WellWater Connected
• Water: PublicWell
• Sewer: Public Sewer

Financial

• Source: Stellar MLS
• Ownership: Fee Simple