75 OSPREY POINT DRIVE
OSPREY, FL 34229
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.
Facts & features
Interior
- Bedrooms
- 4
- Bathrooms
- 4
- Living area
- 4,001 sqft
- Heating
- Heat Pump, Zoned
- Cooling
- Central Air, Zoned
- Flooring
- Carpet, Tile
- Fireplace
- Yes
- Features
- Ceiling Fans(s), Crown Molding, High Ceilings, Primary Bedroom Main Floor, Solid Wood Cabinets, Vaulted Ceiling(s)…
- Appliances
- Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Microwave…
Exterior & lot
- Lot size
- 32,983 sqft (0.76 ac)
- Pool
- Yes
- Roof
- Concrete, Tile
- Construction
- Block, Stucco
Parking
- Garage
- 2 spaces
Financial
- HOA dues
- $5,700 / semi-annually
- Annual tax
- $14,636 (2025)
- Price / sqft
- $399/sqft
Utilities
- Water
- Public
- Sewer
- Public Sewer
- Utilities
- BB/HS Internet Available, Cable Connected
Property
- Property type
- Single Family
- Year built
- 1983
- Subdivision
- OAKS
- County
- Sarasota
Assigned schools
- Elementary
- Laurel Nokomis Elementary
- Middle
- Sarasota Middle
- High
- Venice Senior High
Listing
- Status
- Active
- Days on market
- 65 days
- MLS #
- MFR791813243
- Source
- Stellar MLS
Listed by Steve Abbe · COLDWELL BANKER REALTY
Listing data provided by Stellar MLS. Information deemed reliable but not guaranteed.
Sample estimate — not an appraisal
Based on 20 comparable sales within 4 miles of OSPREY, FL, this home is priced over RENA ValiQ.
Reference only. Estimates blend public sale comps, neighbourhood trend and the listing’s own metrics. Final price moves on diligence, terms and timing — RENA is your second read, not your agent.
Estimate your monthly cost
PITI + HOA- Principal & interest
- $8,065/mo
- Property tax
- $1,220/mo
- Home insurance
- $200/mo
- HOA dues
- $950/mo
Opens at 20% down over 30 years at 6.5%, the same assumptions as the answers below. Property tax is this listing's own bill; insurance is left out until you enter a quote, because Florida premiums turn on roof age, elevation and carrier. Every field is editable.
Ask about this property
Answered from this listing’s own figures and the sales around it.
Price history
From the property’s MLS record.
| Date | Event | Price | Change |
|---|---|---|---|
| Aug 15, 2026 | Price reduced | $1,595,000 | −$54,000 |
| Jun 10, 2026 | Listed | $1,649,000 | — |
NeighbourhoodSample data
Reference scores for OSPREY, FL. Schools, mobility and amenities feed live data once the dedicated provider connection lands.