Date
Details
Price
Change
Source
9/17/2025
Listed
$5,000,000
—
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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$5,000,000
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Property Description
A grand estate where timeless design meets lakefront tranquility, 101 Osprey Point Drive offers refined living within the private gates of The Oaks Bayside. Designed by architect Bo MacEwen, this one-of-a-kind home spans more than 5,000 square feet, all cleverly positioned on nearly an acre with 150 feet of lakefront. Situated on two of the community's most desirable lots, the residence balances architectural distinction with thoughtful updates that ensure comfort and livability. An oversized circular drive paved in granite tile leads to a stately double-door entrance. Inside, the foyer sets the tone with soaring ceilings, hand-crafted moldings, chandeliers, and a white onyx floor with marble inserts. Spaces include an oversized living room with dual fireplaces, a crystal chandelier, and multiple sets of French doors opening to the lakefront patio. The dining room, anchored by another fireplace and framed by custom casings and built-in shelving, is ideal for grand entertaining. A domed ceiling sitting room with French doors to the patio adds an intimate space for cocktails or conversation, while the custom bar and wine room, with etched glass cabinetry, stone counters, and display shelving, enhances the home's appeal for gatherings. The kitchen, completely remodeled in 2019, is a showcase of craftsmanship with UltraKraft® cabinetry, custom soffit lighting, Corian countertops, and a center island with breakfast bar. Luxury appliances include a Sub-Zero refrigerator, Wolf gas cooktop, wall oven, microwave, warming drawer, two KitchenAid dishwashers, and a Frigidaire wine fridge. A butler's pantry provides additional storage, while the sunny breakfast nook overlooks lush gardens. Family and gathering rooms carry the same sense of scale, with dramatic fireplaces, intricate moldings, and detailed ceiling treatments that flow seamlessly for everyday living or large-scale entertaining. The primary suite is a true retreat with a spacious sitting area, custom closets, and a well-appointed bathroom that was newly remodeled in 2025 with spa-inspired finishes. Three guest suites, each with updated full baths (2021 and 2025), provide privacy and comfort. One is a suite with a bathroom near the laundry room, which offers flexibility for live-in staff or extra accommodation. Outdoors, the home embraces its setting with an open pool, expansive deck, and cabana surrounded by manicured hedges and mature landscaping. The views are equally compelling, with mature gardens and community reflecting pond in the front and sweeping lake vistas in the back. Additional highlights include a three-car garage, refinished hardwood floors (2020), and a new Daikin 5-ton AC system installed in 2022. Ownership at The Oaks Club brings an unmatched lifestyle, with two championship golf courses, tennis and pickleball courts, croquet, a fitness center and spa, three on-site restaurants, and a community dock on Little Sarasota Bay. Elegant yet inviting, 101 Osprey Point Drive stands as a rare opportunity to enjoy lakefront living with resort-style amenities in one of Sarasota's most established private enclaves.
Full Property Details
Full Property Details for 101 Osprey Point Dr
General
- Price: $5,000,000
- HOA FEE: $950/month
- HOA FEE FREQ.: Semi-Annually
- Taxes: $12,940 (2025)
- Status: Active
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: A4664424
- Updated: 9/17/2025
- Added to Site: 121 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
- 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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— 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 Pitney Bowes 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# A4664424) is a Single Family property with 4 bedrooms, 5 full bathrooms and 1 partial bathroom. 101 Osprey Point Drive is currently listed for $5,000,000 and was received on September 17, 2025. 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.