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$1,649,000 - 75 Osprey Point Drive, OSPREY

4
Bedrooms
4
Baths
4,001
SQ. Feet
0.76
Acres

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.

Essential Information

  • MLS® #:
    A4695145
  • Price:
    $1,649,000
  • Bedrooms:
    4
  • Bathrooms:
    4.00
  • Full Baths:
    4
  • Square Footage:
    4,001
  • Acres:
    0.76
  • Year Built:
    1983
  • Type:
    Residential
  • Sub-Type:
    Single Family Residence
  • Style:
    Traditional
  • Status:
    Active

Community Information

  • Address:
    75 Osprey Point Drive
  • Area:
    Osprey
  • Subdivision:
    OAKS
  • City:
    OSPREY
  • County:
    Sarasota
  • State:
    FL
  • Zip Code:
    34229-9246

Amenities

  • Amenities:
    Gated, Security, Vehicle Restrictions
  • Parking:
    Circular Driveway, Garage Faces Side
  • # of Garages:
    2
  • View:
    Trees/Woods, Water
  • Waterfront:
    Waterfront
  • Has Pool:
    Yes

Interior

  • Interior Features:
    Ceiling Fan(s), Crown Molding, High Ceilings, Primary Bedroom Main Floor, Solid Wood Cabinets, Vaulted Ceiling(s), Walk-In Closet(s), Window Treatments
  • Appliances:
    Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Microwave, Range, Range Hood, Refrigerator, Washer, Wine Refrigerator
  • Heating:
    Heat Pump, Zoned
  • Cooling:
    Central Air, Zoned
  • Fireplace:
    Yes
  • Fireplaces:
    Wood Burning

Exterior

  • Exterior Features:
    Irrigation System
  • Lot Description:
    In County, Near Golf Course
  • Roof:
    Concrete, Tile
  • Foundation:
    Slab

School Information

  • Elementary:
    Laurel Nokomis Elementary
  • Middle:
    Sarasota Middle
  • High:
    Venice Senior High

Additional Information

  • Days on Market:
    56
  • Zoning:
    RE1

Listing Details

  • Listing Office:
    Coldwell Banker Realty

Listing information courtesy of Coldwell Banker Realty.

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Listing data comes from My Florida Regional MLS.

Listing information last updated on August 8th, 2026 at 3:52am EDT.