Active
101 Osprey Point Dr, Osprey, FL 34229
MLS A4694716
$4,790,000
Est. $26,219/mo principal and interest at 7.28% with 20% down
4 bd · 5.5 ba · 5,087 sqft · Single Family Residence
About this home
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 ass
Key facts
- Type
- Single Family Residence
- Size
- 5,087 sqft
- Bedrooms
- 4
- Bathrooms
- 5.5
- Avg. price per sqft
- $942
- County
- Sarasota
- MLS number
- A4694716
- Status
- Active
- Property address
- 101 Osprey Point Dr, Osprey, FL 34229
Where is this home?
Common questions
How much is 101 Osprey Point Dr, Osprey, FL 34229 listed for?
101 Osprey Point Dr, Osprey, FL 34229 in Osprey, FL is listed at $4,790,000 (about $26,219/mo principal and interest at 7.28% with 20% down).
How many bedrooms and bathrooms does 101 Osprey Point Dr, Osprey, FL 34229 have?
101 Osprey Point Dr, Osprey, FL 34229 has 4 bedrooms, 5.5 bathrooms, and 5,087 square feet.
Who can show 101 Osprey Point Dr, Osprey, FL 34229 in Osprey?
Jonathan Loescher is a Tampa Bay Realtor and Loan Originator. He can tour this home, compare nearby listings, and work the financing with you.
Is there down payment assistance in Tampa Bay?
Some buyers qualify for down payment help. We check income, the house, and the first mortgage at consult. Homes for Heroes and the Buyer Credit are separate benefits, so we pick the one that actually helps your file.
What does the program savings comparison show?
It estimates cash to close or net proceeds under a typical split team, a portal-style path, and working with Jonathan as Realtor and Loan Originator. Figures are educational estimates, not a loan quote.
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