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4 Beds
4 Baths
4,001 sqft

$1,595,000

75 Osprey Point Drive, Osprey FL, 34229

Price per sqft$398.65
Built in1983
Property size4,001 sqft
Property typeResidential

Overview

Active

Listed Jun 11, 2026

Updated 44h ago

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.

$10,612/mo

Est. mortgage payment based on a $1,595,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
A4695145
Available since
June 11, 2026

Interior Features

Bedrooms
4
Bathrooms
4
Cooling
Yes
Heating
Yes
Basement
No

Exterior Features

Lot Size
0.76 Acres

Other Property Details

Taxes
$14,635
Tax Frequency
Annually
Garage
Yes

 

Courtesy of Steve Abbe

Based on information from DASH - Coldwell Banker (CB) as of 10/10/2026. This information is for your personal, non-commercial use and may not be used for any purpose other than to identify prospective properties you may be interested in purchasing. The display of MLS data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information should investigate the data themselves or retain appropriate professionals. Information from sources other than the Listing Agent may have been included in the MLS data. Unless otherwise specified in writing, Broker/Agent has not and will not verify any information obtained from other sources. The Broker/Agent providing the information contained herein may or may not have been the Listing and/or Selling Agent. 

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Data last updated 8:51 AM UTC, 10/10/2026

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