$1,649,000
75 Osprey Point Drive
Osprey, FL 34229
Listing updated: June 12, 2026 at 8:53 PM ET
Property type
Year built
Lot size
Price / sq ft
HOA dues
Day on market
Garage spaces
Flood zone
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.
Estimated monthly payment
Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.
Price & listing history1 days on market
- Status: ActiveJun 11, 2026
- Listed$1,649,000Jun 11, 2026
- Price increased$1,649,000
Facts & features
- Property type
- Residential
- Sub type
- Single Family Residence
- Status
- Active
- Days on market
- 1
- Cumulative DOM
- 182
- Subdivision
- Oaks
- County
- Sarasota
- Year built
- 1983
- Living area
- 4,001 sq ft
- Price/sq ft
- $412
- Building area
- 5,028 sq ft (Public Records)
- Lot size
- 32,983 sq ft
- Lot category
- 1/2 to less than 1
- Flood zone
- X
- Garage
- 2 spaces
- Pool
- Private pool
- Annual taxes
- $14,636 (2025)
- Parcel #
- 0142050014
- Zoning
- RE1
- MLS #
- A4695145
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Interior Details
- Bedrooms
- 4
- Full bathrooms
- 4
- Flooring
- Carpet, Tile
- Appliances
- Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Microwave, Range, Range Hood, Refrigerator, Washer, Wine Refrigerator
- Interior features
- Ceiling Fans(s), Crown Molding, High Ceilings, Primary Bedroom Main Floor, Solid Wood Cabinets, Vaulted Ceiling(s), Walk-In Closet(s), Window Treatments
- Laundry
- Inside, Laundry Room
- Stories / Levels
- One
- Direction faces
- South
- Fireplace
- Yes
Heating & Cooling
- Heating
- Heat Pump, Zoned
- Cooling
- Central Air, Zoned
Parking
- Garage spaces
- 2
- Attached garage
- Yes
- Parking features
- Circular Driveway, Garage Faces Side
HOA & Financial
- HOA fee
- $5,700 / Semi-Annually
- Monthly HOA
- $950/mo
- Total monthly fees
- $950/mo
- Total annual fees
- $11,400
- HOA name
- Access Management/Hope Root
- CDD
- No
- Min lease term
- 1-2 Years
- Listing terms
- Cash, Conventional
- Ownership
- Fee Simple
- Available for lease
- Yes
- Lease restrictions
- Yes
- Additional lease restrictions
- See documents
- Approval process
- Submit application
Exterior & Construction
- Construction materials
- Block, Stucco
- Roof
- Concrete, Tile
- Foundation
- Slab
- Pool
- Private pool
- Water view
- Yes
- Road surface
- Paved
Utilities
- Sewer
- Public Sewer
- Water source
- Public
- Utilities
- BB/HS Internet Available, Cable Connected
Community
- Pets allowed
- Dogs OK, Yes
Schools
Letter grades: Florida DOE 2024–25 school grades (Orange, Seminole, Lake, Osceola, Brevard). Assigned schools from the listing agent — verify enrollment with the district.
Room Details
| Room | Level | Dimensions |
|---|---|---|
| Foyer | First | 12x18 |
| Great Room | First | 22x45 |
| Dining Room | First | 29x40 |
| Studio | First | 12x20 |
| Kitchen | First | 9x15 |
| Primary Bedroom | First | 14x16 |
| Bedroom 2 | First | 13x16 |
| Bedroom 3 | First | 11x11 |
| Laundry | First | 13x8 |
Listing Details
- Listing date
- 2026-06-10
- On market date
- 2026-06-11
- Original list price
- $1,649,000
- Occupant type
- Owner
- MLS area
- 34229 - Osprey
- Listing AOR
- Sarasota - Manatee
- Status changed
- 2026-06-11
- Tax legal description
- LOTS 140 & 141 OAKS
Flood risk
Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.
Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.
Location
Directions
Rte. 41/Tamiami S to The Oaks Bayside entrance. West through guard gate. Bear left to address on right.
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Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Based on information submitted to the MLS GRID as of June 12, 2026 at 8:53 PM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
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