Waterfront - Golf Course - Primary on Main
Address
101 Osprey Point Drive, OSPREY, FL
Price
$ 4,790,000
Property Attributes
- MLS#A4694716
- TypeSingle Family
- Listing Status Active
- CountySarasota
- CityOSPREY
- AreaOsprey
- NeighborhoodOAKS
- Zip34229
- StyleCustom Traditional
- Year Built1985
- Taxes$ 12940
- Price$ 4,790,000
- Bedrooms4
- Full Bathrooms5
- Half Bathrooms1
- Sqr Footage5087
- Lot Size0.93 Acres
Data Source:
Stellar MLS
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.
| Elementary School | Middle School | High School |
|---|---|---|
| Laurel Nokomis Elementary Elementary School | Sarasota Middle Middle School | Venice Senior High High School |
| Price History | |
|---|---|
| 5/26/2026 | Listed $4,790,000 |
General Features
| Sewer | Public Sewer |
|---|---|
| Heating | Central,Electric,Zoned |
| Cooling | Central Air,Zoned |
| Utilities | BB/HS Internet Available,Cable Available,Electricity Connected,Phone Available,Propane,Public,Sewer Connected,Sprinkler Well,Street Lights,Water Connected |
| Roof | Tile |
| 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 |
| Zoning | RSF1 |
| HOA Fee | 5700 |
| Garage Spaces | 3 |
| Association Fee Includes | 24-Hour Guard,Community Pool,Manager,Private Road,Security |
| Patio/Porch Features | Front Porch,Rear Porch |
| Architectural Style | Custom,Traditional |
| Pool Features | Gunite,In Ground |
| Security Features | Gated Community,Security System Owned,Smoke Detector(s) |
| Construction Materials | Block,Stucco |
| Pets Allowed | Yes |
| Year Built | 1985 |
| View | Water |
| Levels | One |
| Property Subtype | Single Family Residence |
| Tax Year | 2025 |
| Ownership | Fee Simple |
| Waterfront Features | Lake Front |
| Community Features | Buyer Approval Required,Clubhouse,Deed Restrictions,Fitness Center,Gated Community - Guard,Golf,Pool,Special Community Restrictions,Tennis Court(s) |
| Assoc Fee Paid Per | Semi-Annually |
| County | Sarasota |
| New Construction | false |
| Property Type | Residential |
| Association Amenities | Clubhouse,Fitness Center,Gated,Handicap Modified,Pool,Recreation Facilities,Security,Tennis Court(s) |
| Attached Garage | true |
| Subdivision Name | OAKS |
| Facing Direction | West |
| Garage Y/N | true |
| Total Rooms | 10 |
| Full Baths | 5 |
| Status | Active |
| Directions | US 41 to west into Oaks Bayside - Osprey Point Drive. Follow to 101 on the right. |
| High School | Venice Senior High |
| City | OSPREY |
| Association Name | Asset Management/ Hope Root |
| Senior Community Y/N | false |
| MLS Area | 34229 - Osprey |
| Lot Size Units | Square Feet |
| Lot Size Square Feet | 40593 |
| Carport Y/N | false |
| Listing Terms | Cash,Conventional |
| Spa Features | In Ground |
| Elementary School | Laurel Nokomis Elementary |
| Land Lease Y/N | false |
| Tax Annual Amount | 12940.05 |
| Middle/Junior High School | Sarasota Middle |
| Additional Parcels Y/N | false |
| Lease Considered Y/N | true |
| Virtual Tour | https://listings.threesixtyviews.net/videos/019953f8-eec5-710f-bd80-86bf091497ce |
| Building Area Units | Square Feet |
| Living Area Units | Square Feet |
| Standard Status | Active |
| Occupancy Type | Owner |
| Tax Lot | 147 |
| 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 |
| Water View | Lake |
| Pet Size Limit | Extra Large (101+ Lbs.) |
| Minimum Lease | 1-2 Years |
| Water Access Y/N | false |
| Monthly HOA Amount | 950 |
| Additional Rooms | Breakfast Room Separate,Den/Library/Office,Family Room,Formal Dining Room Separate,Formal Living Room Separate |
| Water View Y/N | true |
| Flood Zone Code | AE X |
| In Law Suite YN | false |
| Flood Zone Code X | Yes |
Interior Features
| Interior Amenities | 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 |
|---|---|
| Flooring | Brick/Stone,Ceramic Tile,Parquet |
| Furnished Y/N | Unfurnished |
| Fireplace Features | Family Room,Living Room,Other Room,Master Bedroom,Wood Burning |
| Air Conditioning Y/N | true |
| Heating Y/N | true |
| Window Features | Blinds,Drapes,Window Treatments |
| Fireplace Y/N | true |
| Half Baths | 1 |
| Laundry Features | Inside,Laundry Room |
| Total Bedrooms | 4 |
| LivingAreaSource | Public Records |
| Total Baths | 6 |
Exterior Features
| Exterior Amenities | French Doors,Hurricane Shutters,Irrigation System,Lighting,Private Mailbox |
|---|---|
| Vegetation | Mature Landscaping,Trees/Landscaped |
| Parking Features | Circular Driveway,Driveway,Garage Door Opener,Garage Faces Side,Off Street |
| Lot Features | Cul-De-Sac,In County,Landscaped |
| Water Source | Public,Well |
| Lot Size Area | 40593 |
| Foundation Details | Slab |
| Spa | true |
| Building Area Total | 6841 |
| Lot Size Acres | 0.93 |
| Road Surface Type | Paved,Asphalt |
| Private Pool | true |
| Waterfront Y/N | true |
| Covered Spaces | 3 |
| Road Frontage Type | Street Paved |
Amenities
- Foreclosure
- Views
- Short Sale
- New Construction
- Adult 55+
- Lease To Own
- No HOA Fees
- Furnished
- Primary On Main
- Air Conditioning
- Seller Finance
- Green
- Fixer Upper
- Horse
- Golf
- Fireplace
- Deck
- Garage
- Basement
- Pool
Property vs Single Family Average in 34229
Price
Taxes
Year Built
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All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Updated on August 21, 2026 8:58 PM UTC
