75 Osprey Point Drive, OSPREY, FL 34229-9246
- $1,595,000MLS® # A4695145
- 4 Bedrooms
- 4 Bathrooms
- 4,001 SQ. Feet
- 1983 Year Built
Offered at a price approaching the value of the two buildable lots alone, this architect-designed estate represents one of the most compelling opportunities currently available in The Oaks. Nestled beneath majestic oak trees and surrounded by exceptional privacy, this architecturally significant residence was designed by and as the personal home of renowned architect Bo MacEwen. The property encompasses two buildable lots and includes a charming guest house, creating a rare and versatile estate setting. A grand foyer measuring approximately 12 feet wide by 19 feet long welcomes guests and leads to an impressive great room featuring soaring vaulted ceilings, a gas fireplace, and a dramatic bay window with built-in seating overlooking the beautifully landscaped grounds. Architectural details abound, including 14-inch crown molding, Palladian windows, wainscoting, skylights, custom lighting, and distinctive craftsmanship throughout. The home offers four bedrooms and four full bathrooms, thoughtfully designed to blend elegance, comfort, and timeless architectural character. Throughout the residence, quality construction and meticulous attention to detail reflect the vision of its celebrated designer. Step outside to discover a tranquil, resort-inspired setting featuring a sparkling pool, lush landscaping, and a separate guest house ideal for visitors, extended family, or a private office. In the evening, landscape lighting transforms the grounds into a serene retreat unlike anything else in the community. Residents of The Bayside enjoy a 24-hour guarded entrance and a private community pier perfect for kayaking, fishing, or taking in spectacular sunsets over Casey Key. Ownership also provides access to the exceptional lifestyle of The Oaks Club, featuring two championship 18-hole golf courses, 12 Har-Tru tennis courts, four pickleball courts, the state-of-the-art WellFit Center, a Junior Olympic swimming pool, outstanding dining venues, and an active year-round social calendar. Club membership is required, and there is currently no waiting list for either Golf or Sports/Social membership.
Price Change History for 75 Osprey Point Drive, OSPREY, FL (MLS® #A4695145)
| Date | Details | Change |
|---|---|---|
| Price Reduced from $1,649,000 to $1,595,000 |
Property
Location
- NeighborhoodAshley Oaks
- Address75 Osprey Point Drive
- CityOSPREY
- StateFL
Size And Restrictions
- Acres0.76
- Lot DescriptionIn County, Near Golf Course
Improvements
- FenceNo
- SprinklerNo
Features
- ViewTrees/Woods, Water
Market
- Date ListedJune 11th, 2026
- Days On Market68
- Estimated Payment
Interior
Bedrooms And Bathrooms
- Bedrooms4
- Bathrooms4.00
Heating And Cooling
- HeatingHeat Pump, Zoned
- Air ConditioningCentral Air, Zoned
- FireplaceYes
Interior Features
- AppliancesDishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Microwave, Range, Range Hood, Refrigerator, Washer, Wine Refrigerator
- FeaturesCeiling Fan(s), Crown Molding, High Ceilings, Primary Bedroom Main Floor, Solid Wood Cabinets, Vaulted Ceiling(s), Walk-In Closet(s), Window Treatments
Building
Building Information
- Year Built1983
- RoofConcrete, Tile
Property Features
- Exterior FeaturesIrrigation System
Garage And Parking
- GarageCircular Driveway, Garage Faces Side
Community
Amenities
- Area AmenitiesGated, Security, Vehicle Restrictions
Schools
- ElementaryLaurel Nokomis Elementary
- MiddleSarasota Middle
- HighVenice Senior High
Info
- OfficeCOLDWELL BANKER REALTY
Map & Directions
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Listing data comes from My Florida Regional MLS DBA Stellar MLS.
Listing information last updated on August 19th, 2026 at 8:22pm EDT.