To schedule a showing of 101 Osprey Point Drive, Osprey, Florida, Call David Shippey at 863-521-4517 TODAY!
$4,790,000 | 4 beds | 5 full baths | 1 half baths | 5,087 sqft
Osprey, FL 34229
- 4Beds
- 6.00Total Baths
- 5 Full, 1 HalfBaths
- 5,087SqFt
- 1985Year Built
- 0.93Acres
- MLS# A4694716
- Residential
- SingleFamilyResidence
- Active
- Approx Time on Market11 days
- Area34229 - Osprey
- CountySarasota
- Subdivision The Oaks
Overview
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 Sarasotas prestigious Oaks Bayside community. Spanning more than 5,000 square feet across two of the communitys 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 chefs 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 butlers pantry and sunlit breakfast nook overlooking the gardens further enhance the homes 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 Sarasotas 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 Coasts most established luxury communities.
Agriculture / Farm
Association Fees / Info
Community Features: Clubhouse, Fitness, Golf, Pool, TennisCourts, Gated, StreetLights
Pets Allowed: Yes
Hoa Frequency Rate: 5700
Association: Yes
Association Amenities: Clubhouse, FitnessCenter, Gated, Pool, RecreationFacilities, Security, TennisCourts
Hoa Fees Frequency: SemiAnnually
Association Fee Includes: AssociationManagement, Pools, RoadMaintenance, Security
Bathroom Info
Total Baths: 6.00
Fullbaths: 5
Building Info
Window Features: Blinds, Drapes, WindowTreatments
Roof: Tile
Building Area Source: PublicRecords
Buyer Compensation
Exterior Features
Style: Custom, Traditional
Pool Features: Gunite, InGround, Association, Community
Patio: RearPorch, FrontPorch
Pool Private: Yes
Exterior Features: FrenchPatioDoors, SprinklerIrrigation, Lighting, StormSecurityShutters
Fees / Restrictions
Financial
Original Price: $4,790,000
Disclosures: CovenantsRestrictionsDisclosure
Garage / Parking
Parking Features: CircularDriveway, Driveway, Garage, GarageDoorOpener, OffStreet, GarageFacesSide
Attached Garage: Yes
Garage: Yes
Green / Env Info
Interior Features
Fireplace Desc: FamilyRoom, LivingRoom, PrimaryBedroom, Other, WoodBurning
Fireplace: Yes
Floors: Brick, CeramicTile, Parquet
Levels: One
Spa: Yes
Laundry Features: Inside, LaundryRoom
Interior Features: WetBar, BuiltInFeatures, ChairRail, CeilingFans, CrownMolding, EatInKitchen, HighCeilings, MainLevelPrimary, StoneCounters, SolidSurfaceCounters, WalkInClosets, WindowTreatments, SeparateFormalDiningRoom, SeparateFormalLivingRoom
Appliances: BarFridge, BuiltInOven, Cooktop, Dryer, Dishwasher, ElectricWaterHeater, Disposal, Microwave, Refrigerator, RangeHood, WaterSoftener, WaterPurifier, WineRefrigerator, Washer
Spa Features: InGround
Lot Info
Direction Remarks: US 41 to west into Oaks Bayside - Osprey Point Drive. Follow to 101 on the right.
Lot Size Units: Acres
Lot Size Acres: 0.93
Lot Sqft: 40,593
Vegetation: PartiallyWooded
Lot Desc: CulDeSac, OutsideCityLimits, BuyerApprovalRequired, Landscaped
Misc
Other
Special Conditions: None
Security Features: SecuritySystemOwned, SmokeDetectors, GatedWithGuard, GatedCommunity
Other Rooms Info
Property Info
Section: 03
Class Type: SingleFamilyResidence
Property Sub Type: SingleFamilyResidence
Construction Materials: Block, Stucco
Stories: 1
Foundation: Slab
Human Modified: Yes
Room Info
Total Rooms: 10
Sqft Info
Sqft: 5,087
Bulding Area Sqft: 6,841
Living Area Units: SquareFeet
Living Area Source: PublicRecords
Tax Info
Tax Year: 2,025
Tax Lot: 147
Tax Legal Description: LOTS 147 & 148, LESS N 30 FT OF LOT 148, TOGETHER 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 POB, OAKS, BEING SAME LANDS AS DESC IN ORI 2022112936
Tax Annual Amount: 12940.05
Tax Book Number: 2111-2937
Unit Info
Utilities / Hvac
Heating: Central, Electric, Zoned
Water Source: Public, Well
Sewer: PublicSewer
Cool System: CentralAir, Zoned, CeilingFans
Cooling: Yes
Heating: Yes
Utilities: CableAvailable, ElectricityConnected, HighSpeedInternetAvailable, Propane, MunicipalUtilities, PhoneAvailable, SewerConnected, WaterConnected
Waterfront / Water
Waterfront: Yes
Waterfront Features: LakeFront
View: Yes
View: Lake, Water
Directions
US 41 to west into Oaks Bayside - Osprey Point Drive. Follow to 101 on the right.This listing courtesy of Douglas Elliman
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MLS IDX data last updated on 06-06-2026 7:56 PM EST.
If you have any questions on 101 Osprey Point Drive, Osprey, Florida, please call David Shippey at 863-521-4517.
MLS# A4694716 located at 101 Osprey Point Drive, Osprey, Florida is brought to you by David Shippey REALTOR®
101 Osprey Point Drive, Osprey, Florida has 4 Beds, 5 Full Bath, and 1 Half Bath.
The MLS Number for 101 Osprey Point Drive, Osprey, Florida is A4694716.
The price for 101 Osprey Point Drive, Osprey, Florida is $4,790,000.
The status of 101 Osprey Point Drive, Osprey, Florida is Active.
The subdivision of 101 Osprey Point Drive, Osprey, Florida is The Oaks.
The home located at 101 Osprey Point Drive, Osprey, Florida was built in 2026.