75 OSPREY POINT DRIVE, Osprey, FL 34229

• 4 beds |
• 4 baths |
• 4,001 sqft

Property Description

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.

Listing Status:

Active

Date Added:

June 11, 2026

Data Last Updated:

June 28, 2026 at 7:23AM

Listing Office:

COLDWELL BANKER REALTY : 941-383-6411

Listing Agent:

Steve Abbe : 941-400-3969

MLS ID:

A4695145

Interior

• General: Ceiling Fans(s)Crown MoldingHigh CeilingsPrimary Bedroom Main FloorSolid Wood CabinetsVaulted Ceiling(s)Walk-In Closet(s)Window Treatments
• Rooms: Breakfast Room SeparateDen/Library/OfficeFamily RoomFormal Dining Room SeparateFormal Living Room SeparateGreat Room
• Appliances: DishwasherDisposalDryerElectric Water HeaterExhaust FanMicrowaveRangeRange HoodRefrigeratorWasherWine Refrigerator
• Laundry: InsideLaundry Room
• Flooring: CarpetTile
• A/C: Central AirZoned
• Heating: Heat PumpZoned
• Fireplace: GasFireplace

Exterior

• Style: Traditional
• Other Structures: Guest HousePatio
• Pool: In Ground
• Parking: Circular DrivewayGarage Faces Side

Construction

• Roofing: ConcreteTile
• Windows: BlindsDrapesInsulated WindowsRodsWindow Treatments
• General: BlockStuccoOneSlab

Location

• Road/Access: Paved
• HOA Amenities: GatedSecurityVehicle RestrictionsGuard - 24 HourCommon Area TaxesEscrow Reserves FundFidelity BondManagementPrivate RoadSecurity5700.0Semi-Annually
• Originating MLS: Stellar MLS
• County: Sarasota

Lot

• Zoning: RE1LOTS 140 & 141 OAKS0142050014
• View: Trees/WoodsWater

Utilities

• Utilities: BB/HS Internet AvailableCable Connected
• Water: Public
• Sewer: Public Sewer

Financial

• Source: Stellar MLS
• Ownership: Fee Simple