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.
Property Details
- Interior
- Built-in Features, Ceiling Fans(s), Chair Rail, Crown Molding, Eat-in Kitchen, High Ceilings, Primary Bedroom Main Floor, Solid
- Heating
- Central, Electric, Zoned
- Cooling Features
- Central Air, Zoned
- Bedrooms
- 4
- Bathrooms
- 5.5
- Full Baths
- 5
- Half Baths
- 1
- View
- Water
- Lot Features
- Cul-De-Sac, In County, Landscaped, Paved
- Lot Description
- Cul-De-Sac, In County, Landscaped, Paved
- Pool
- 1
- Pool Description
- Gunite, In Ground
- Pool Features
- Gunite, In Ground
- Exterior Materials
- Hurricane Shutters, Lighting, Private Mailbox
- Pool Shared
- 1
- Acres
- 0.93
- Square Feet
- 6841.0
- Parking Features
- Circular Driveway, Driveway, Garage Door Opener, Garage Faces Side, Off Street
- Parking
- 1
- Parking Spaces
- 3
- Parking Type
- Driveway
- Parking Garage Spaces
- 3.0
- Property Type
- Purchase
- Year Built
- 1985
- Foundation
- Slab
- Roof
- Tile
- Sewer Information
- Public Sewer
- Utility Source
- Public, Well
- Utility Features
- BB/HS Internet Available, Cable Available, Electricity Connected, Phone Available, Propane, Public, Sewer Connected, Sprinkler W
- Appliances
- Bar Fridge, Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range Hood, Refrigerator, Was
- Subdivision
- OAKS
- Community Features
- Buyer Approval Required, Clubhouse, Deed Restrictions, Fitness Center, Gated Community - Guard, Golf, Pool, Special Community Re
- Elementary School
- Laurel Nokomis Elementary
- Middle School
- Sarasota Middle
- High School
- Venice Senior High
- County
- Sarasota
- Region
- OSPREY
- Zoning
- RSF1
- Original List Price
- $4,790,000
- Days on Market (Cumulative)
- 110
- Taxes Annual
- $12,940
- HOA
- 1
- HOA Fees
- 5700.0
- Ownership
- Fee Simple
- MLS #
- A4694716
Location
Legal
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Some IDX listings have been excluded from this website. Listing Information presented by local MLS brokerage: Del Amo Realty
Provided By
Listed by Joel Schemmel (#MFR281504356)
Listing Office: DOUGLAS ELLIMAN (#MFR281542877)
