75 OSPREY POINT DRIVE

Property Details

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.

Facts & Costs

Property type

Single Family Residence

Year built

1983

Lot size

0.76 acres

Garage

2 spaces

Price per sq ft

$399

Days on market

111

Private pool

Yes

Waterfront

No

Community

The Oaks

Subdivision

OAKS

County

Sarasota

Builder

Bo MacEwen

Flood zone

X

Monthly & yearly costs

HOA fee

$5,700 / semi-annually

Property taxes

$14,636 / year (2025)

As reported by the listing agent. Verify with the HOA and county.

Construction & systems

Heating

Heat Pump, Zoned

Cooling

Central Air, Zoned

Flooring

Carpet, Tile

Roof

Concrete, Tile

Construction

Block, Stucco

Parking

Circular Driveway, Garage Faces Side

View

Trees/Woods, Water

Payment Estimate

$10,235 / month

Principal & interest

$8,065

Property taxes

$1,220

HOA

$950

Home insurance

enter below

Estimate only, not a loan offer. Rate is a starting value; taxes and HOA are as reported by the listing agent. Florida insurance (including flood) varies widely. Ask George for a lender referral.

Location

Features & Amenities

• Dishwasher
• Disposal
• Dryer
• Electric Water Heater
• Exhaust Fan
• Microwave
• Range
• Range Hood
• Refrigerator
• Washer
• Wine Refrigerator
• Ceiling Fans(s)
• Crown Molding
• High Ceilings
• Primary Bedroom Main Floor
• Solid Wood Cabinets
• Vaulted Ceiling(s)
• Walk-In Closet(s)
• Window Treatments
• In Ground