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- Property Details
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$1,595,000
Monthly Est:$7,939
4 Beds
- 4 Baths
4 full baths
4,001sqft
75 Osprey Point Dr, Osprey, FL 34229
$1,595,000
$7,939/moEst:
Get Pre-Approved
Single Family Residence
Built in 1983
$950/mo HOA
32,983 sqft lot
$399/sq.ft
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.
- Houzeo last checked: 0 minutes ago
- Listing updated: October 7, 2026 at 1:24 pm
- Listing Provided by: Steve Abbe (941) 400-3969 , Shannon Rocha | COLDWELL BANKER REALTY (941) 383-6411
- Source: Stellar MLS-FL | MLS#: A4695145

Property Details
Status
Active
Type
Single Family Residence
No. of Stories
-
County
City
Neighborhood
--
Year Built
1983
HOA Fees
$950/mo
Finished Area
4,001 sqft
Lot Size
32,983 sqft lot
Basement Area
- sqft
MLS Name
Stellar MLS
MLS Number
A4695145
MLS Status
Active
Days on Market
121
Cumulative Days on Market
287

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Location
HOA Management
Access Management/Hope Root
HOA Fees
$5,700/ Semi-Annually
Amenities
Amenities and services may be covered by one or multiple associations and service providers.
Security Guard
Security Gate
Management
Vehicle Restrictions
Fidelity Bond
Private Road
Escrow Reserves Fund
Common Area Taxes
Disclaimer: Amenities are based on third-party information and may vary; buyers must independently verify all amenities, as information is deemed reliable but not guaranteed.
Facts & Features
Rooms
Bedrooms & bathrooms
Bedrooms: 4
Bathrooms: 4
Foyer
Level: First
Area: 216.00 Square Feet
Dimensions: 12x18
Great Room
Level: First
Area: 990.00 Square Feet
Dimensions: 22x45
Dining Room
Level: First
Area: 1160.00 Square Feet
Dimensions: 29x40
Studio
Level: First
Area: 240.00 Square Feet
Dimensions: 12x20
Kitchen
Level: First
Area: 135.00 Square Feet
Dimensions: 9x15
Primary Bedroom
Level: First
Area: 224.00 Square Feet
Dimensions: 14x16
Bedroom 2
Level: First
Area: 208.00 Square Feet
Dimensions: 13x16
Bedroom 3
Level: First
Area: 121.00 Square Feet
Dimensions: 11x11
Laundry
Level: First
Area: 104.00 Square Feet
Dimensions: 13x8
Interior
Appliances
Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Microwave, Range, Range Hood, Refrigerator, Washer, Wine Refrigerator
Heating
Heat Pump, Zoned
Window Features
Blinds, Drapes, Insulated Windows, Rods, Window Treatments
Cooling
Central Air, Zoned
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
Sewer
Public Sewer
Flooring
Carpet, Tile
Construction
Year Built
Year Built: 1983
Home type
Single Family Residence
Architectural Style
Traditional
Construction Materials
Block, Stucco
Roof
Concrete, Tile
Foundation Details
Slab
Utilities & Energy
Parking Features
Circular Driveway, Garage Faces Side
Association Amenities
Gated, Security, Vehicle Restrictions
Utilities
Bb/hs Internet Available, Cable Connected
Security Features
Security System, Security System Owned, Smoke Detector(s)
Pool Features
In Ground
Water Source
Public
Laundry Features
Inside, Laundry Room
Fireplace Features
Wood Burning
Other Features
Patio And Porch Features
Patio
Lot Features
In County, Near Golf Course, Private
Community Features
Deed Restrictions, Golf, Irrigation Reclaimed Water
Subdivision Name
Oaks
Vegetation
Bamboo, Mature Landscaping, Oak Trees, Trees/landscaped, Wooded
Price History
| Date | Event | Price |
|---|---|---|
10/07/2026 Source: | Listed for Sale | $1,595,000 $399/sqft |
08/13/2026 Source: | Pending | $1,595,000 -3.27% $399/sqft |
06/11/2026 Source: | Listed for Sale | $1,649,000 -2.71% $412/sqft |
05/20/2026 Source: | Listing Removed | $1,695,000 $424/sqft |
04/14/2026 Source: | Price Decreased | $1,695,000 -4.51% $424/sqft |
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Based on information from Stellar MLS® through Oct 11, 2026, 12:30AM as submitted to and distributed by MLS GRID. All data is obtained from various sources and may not have been verified by the 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. IDX information is provided exclusively for consumers’ personal non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. The use of the MLS GRID Data may be subject to an end-user license agreement prescribed by the Member Participant’s applicable MLS, if any, and as amended from time to time. © 2026 Stellar MLS. All Rights Reserved.
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