Date
Details
Price
Change
Source
5/26/2026
Listed
$4,790,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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$4,790,000
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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.
Full Property Details
Full Property Details for 101 Osprey Point Dr
General
- Price: $4,790,000
- HOA FEE: $950/month
- HOA FEE FREQ.: Semi-Annually
- Taxes: $12,940 (2025)
- Status: Active
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: A4694716
- Updated: 5/26/2026
- Added to Site: 49 day(s) ago
Rental Information
- Min. Lease: 1-2 Years
Interior
- Number of Rooms: 10
- Interior Features: Built-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
- Fireplace: Yes
- Fireplace(s): Family Room, Living Room, Other Room, Master Bedroom, Wood Burning
- Appliances: Bar Fridge, Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range Hood, Refrigerator, Washer, Water Filtration System, Water Softener, Wine Refrigerator
- Furnishings: Unfurnished
- Flooring: Brick/Stone, Ceramic Tile, Parquet
Rooms
Bathrooms
- Total Bathrooms: 6
- Full Bathrooms: 5
- Half Bathrooms: 1
Bedrooms
- Total Bedrooms: 4
Other Rooms
- Laundry: Inside, Laundry Room
Additional Information
- Shared Amenities: Clubhouse, Fitness Center, Gated, Handicap Modified, Pool, Recreation Facilities, Security, Tennis Court(s)
- Pool: Yes
- Private Pool: Yes
- Pool Description: Gunite, In Ground
- Spa: Yes
- Spa Description: In Ground
- Security/Safety: Gated Community, Security System Owned, Smoke Detector(s)
Exterior
- Exterior Features: French Doors, Hurricane Shutters, Irrigation System, Lighting, Private Mailbox
- Deck/Patio: Front Porch, Rear Porch
- Porch/Patio/Deck: Front Porch, Rear Porch
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 3
- Covered Spaces: 3
- Parking Features: Circular Driveway, Driveway, Garage Door Opener, Garage Faces Side, Off Street
Location
- Area: 34229 - Osprey
- County: Sarasota
- Development Name: 34229 - Osprey
- Subdivision: THE OAKS
- Driving Directions: US 41 to west into Oaks Bayside - Osprey Point Drive. Follow to 101 on the right.
- Direction Faces: West
School Information
- Elementary School: Laurel Nokomis Elementary
- Middle School: Sarasota Middle
- High School: Venice Senior High
Community
- Community Name: 34229 - Osprey
- Community Features: Buyer Approval Required, Clubhouse, Deed Restrictions, Fitness Center, Gated Community - Guard, Golf, Pool, Special Community Restrictions, Tennis Court(s)
- Optional Amenities: Clubhouse, Fitness Center, Gated, Handicap Modified, Pool, Recreation Facilities, Security, Tennis Court(s)
- Association: Yes
- Assoc. Name: Asset Management/ Hope Root
- Assoc. Fees Include: 24-Hour Guard, Community Pool, Manager, Private Road, Security
Heating & Cooling
- Cooling Type: Central Air, Zoned
- Heating Type: Central, Electric, Zoned
Utilities
- Sewer: Public Sewer
- Water: Public, Well
- Utility Description: BB/HS Internet Available, Cable TV Available, Electricity Connected, Phone Available, Propane, Public, Sewer Connected, Sprinkler Well, Street Lights, Water Connected
Structural Information
- Architectural Info: Custom, Traditional
- Architectural Style: Custom, Traditional
- Exterior Const.: Block, Stucco
- Roof: Tile
- Windows: Blinds, Drapes, Window Treatments
- Stories/Levels: One
- Square Feet: 5,087
- Sq. Ft. Source: Public Records
- Year Built: 1985
Lot Features
- Property View: Water
- Lot Size (Acres): 0.93
- Lot Size (Sq. Ft.): 40,593
- Lot Size: 40593
- Frontage: Street Paved
- Street/Road Desc.: Paved, Asphalt
Water Features
- Water Front: Yes
- Water View: Yes
- Water Front Desc.: Lake Front
Financial Considerations
- Association Fee: $5,700
- Assoc Fee Freq.: Semi-Annually
- Assoc Fee Desc.: Required
- Tax Amount: $12,940.05
- Tax Year: 2025
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- 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
- Flood Zone Info: AE X
- APN: 142050008
- Property ID: 142050008
Listed by Douglas Elliman
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Listing agent
— 101 Osprey Point Dr —
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Schools
Schools serving 101 Osprey Point Dr
School District:Sarasota County School District
| Name | Grades | Distance |
|---|---|---|
Laurel Nokomis School 1900 Laurel Road East, Nokomis, FL 34275 | PK-8 | 6.7 mi |
Venice Senior High School 1 Indian Avenue, Venice, FL 34285 | 9-12 | 8.6 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 101 Osprey Point Dr
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101 Osprey Point Drive, Osprey, FL 34229 (MLS# A4694716) is a Single Family property with 4 bedrooms, 5 full bathrooms and 1 partial bathroom. 101 Osprey Point Drive is currently listed for $4,790,000 and was received on May 26, 2026. Want to learn more about 101 Osprey Point Drive? Do you have questions about finding other Single Family real estate for sale in Osprey? You can browse all Osprey real estate or contact a Coldwell Banker agent to request more information.