Beds
4
Baths
4
Sq Ft
4,001 sq ft
Year Built
1983
Lot Size
0.76 acres
Garage
2
About This Property
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.
Property Overview
Interior Features
Exterior & Lot
Pool & Spa
Utilities
Parking
HOA & Community
Financial Details
Schools
Directions
Rte. 41/Tamiami S to The Oaks Bayside entrance. West through guard gate. Bear left to address on right.
Location
75 OSPREY POINT DRIVE, OSPREY, FL 34229
Listing Information
Schedule a Showing
How to Buy This Home
Multiple financing options available for this $1,649,000 home in OSPREY.
🏛️
FHA Loan
$57,715 Down
Government-backed, low down payment. Credit scores as low as 580.
🎖️
VA Loan
$0 Down
Zero down for eligible veterans, active duty, and military families.
🏦
Conventional
$82,450 Down
Traditional financing. As low as 3-5% down with good credit.
🌾
USDA Loan
$0 Down
Zero down for eligible rural areas. Income limits apply.
Florida Down Payment Assistance Programs
You may qualify for up to $35,000 in assistance to cover your down payment and closing costs.
Florida Hometown Heroes
Up to $35,000
First-time buyers working in FL
FL Assist
Up to $10,000
FHA, VA, or USDA borrowers
FL HLP Second Mortgage
Up to $10,000
First-time buyers, 0% deferred
Sarasota County SHIP
Varies
Income-qualifying Sarasota residents
Can You Afford This Home?
Quick check based on the 28% debt-to-income rule. Not a guarantee — just a starting point.
Listing information is deemed reliable but not guaranteed. All measurements and data should be independently verified. This information is provided by the Stellar MLS. The listing broker's offer of compensation is made only to participants of the MLS where the listing is filed. 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. Data last updated: June 13, 2026.