$1,595,000

75 Osprey Point DrOsprey, FL 34229

  • 4 beds
  • 4 baths
  • 4,001 sqft
  • 0.76 acres
  • 147 days on market

About this home

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.

Virtual tour

Facts

Property type
Single Family Residence
Year built
1983
Garage spaces
2
Lot size
0.76 acres
Pool
Yes
Waterfront
No
Water view
Pond
Subdivision
OAKS
Community
The Oaks
County
Sarasota
HOA fee
$5,700 / semi-annually
CDD
0
Annual taxes
$14,636 (2025)
Flood zone
X
Pets
Dogs OK, Yes
New construction
No
MLS #
A4695145

Features

Interior
Ceiling Fans(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
Flooring
Carpet, Tile
Heating
Heat Pump, Zoned
Cooling
Central Air, Zoned
Patio & porch
Patio
Pool features
In Ground
Parking
Circular Driveway, Garage Faces Side
Construction
Block, Stucco
Roof
Concrete, Tile
Lot
In County, Near Golf Course, Private
View
Trees/Woods, Water
Community features
Deed Restrictions, Golf, Irrigation-Reclaimed Water
Association amenities
Gated, Security, Vehicle Restrictions
HOA fee includes
Guard - 24 Hour, Common Area Taxes, Escrow Reserves Fund, Fidelity Bond, Management, Private Road, Security
Utilities
BB/HS Internet Available, Cable Connected
Water
Public
Sewer
Public Sewer
Elementary school
Laurel Nokomis Elementary
Middle school
Sarasota Middle
High school
Venice Senior High

Location

Stellar MLS Listing courtesy of COLDWELL BANKER REALTY. MLS # A4695145.

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Stellar MLS

Listing information is provided by Participants of the Stellar MLS. 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. Properties displayed may be listed or sold by various participants in the MLS Copyright 2026, Stellar MLS. Last updated: 2026-11-04 1:00 PM EST.