When helping upscale clientele in Southwest Florida, real estate professionals make it a point to mention The Gated Oaks Bayside neighborhood in Sarasota County. The Oaks Bayside Osprey Florida boasts a special historical distinction: this is the residential community that real estate magnate and socialite Bertha Palmer once called home.
Bertha Palmer is the visionary after whom the Palmer Ranch master-planned development of Sarasota County is named. In the first quarter of the 20th century, Ms. Palmer decided to build an opulent mansion right on this site; although her lavish estate is no longer around, the Oaks Bayside retains Ms. Palmer’s refined taste in suburban development.
The Oaks Bayside Osprey, Florida, is a distinguished community comprising approximately 133 estates, each offering unique views of Little Sarasota Bay, serene lakes, or lush nature preserves. The neighborhood showcases a diverse array of architectural styles, including Mediterranean, Southern Plantation, Spanish Colonial, and English Chateau, reflecting a timeless elegance that defines one of Southwest Florida’s most prestigious enclaves.
As of March 2025, the real estate market in The Oaks Bayside remains dynamic, with property prices ranging from around $299,000 to over $4 million. The median listing price is approximately $1,275,000, with homes typically spending an average of 95 days on the market. Prospective buyers can expect to find spacious residences, often featuring at least three bedrooms and encompassing over 4,000 square feet of living space. The community’s active real estate landscape ensures that a variety of listings are available at any given time, catering to discerning homebuyers seeking luxury and comfort in a serene setting.
The Oaks Bayside continues to attract buyers with its unique blend of architectural beauty, natural surroundings, and upscale amenities. Latest pricing at the Oaks Bayside Osprey Florida will be found below if there is inventory.
The Oaks Bayside is part of an exclusive country club that features two championship gold courses and a palatial clubhouse. Besides golf, club members and their guests can also enjoy tennis, croquet, fitness center and swimming; children have their own playground in the club grounds to enjoy. Residents here live very close to the Sarasota Mall Warehouse Costco and to major shopping districts.
Neighborhood Slideshow of the Oaks Golf & Country Club in Osprey
Oaks Bayside Osprey Florida Homes for Sale
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(all data current as of
3/25/2025)
Listing information deemed reliable but not guaranteed. Read full disclaimer.
