Southbay Yacht & Racquet Club in Osprey : Homes for Sale

When American circus magnate John Ringling set out to develop real estate in Sarasota, he envisioned neighborhoods that took full advantage of the year-round sunny climate and the natural beauty of Florida. The current trend of building resort-style communities is owed to the Ringling’s vision, and this was the blueprint for the development of Southbay in Osprey in the mid-1970s.

Formally known as the Southbay Yacht and Racquet Club, this neighborhood is located in the southwest section of Osprey. Southbay sits on the spot once occupied by Floridaland, an amusement park that folded when Disney World opened in Orlando. The former park is now a waterfront neighborhood that offers a marina along with many other amenities as well as gorgeous real estate.

Southbay is a fairly large community that faces Dryman Bay and Casey Key; it is located south of Blackburn Point Road and west of the Tamiami Trail, right in between Shoreland Park and Blackburn Point Park, two green spaces that buffer out traffic noise. Many of the homes in Southbay are Florida ranches that have been upgraded and remodeled over the years; some feature touches of Mediterranean revival style while others have splashes of Caribbean design.

If you are interested in spacious homes built on large lots, you can certainly find such listings in Southbay. In September 2020, a four-bedroom home offered for $775 featured 3,479 square feet of interior built on a lot measuring nearly 10,600 square feet. Pricing starts under $600K for three-bedroom homes with at least two full bathrooms and a two-car garage.

Since Southbay is a yacht club, the main amenities are the marina and its elegant clubhouse complete with catering kitchen, lounge, and ballroom. The fitness center connects to a sauna, and the swimming pool is right outside. Southbay residents have their own private park; Lookout Point offers five miles of trails perfect for strolling, jogging, or biking along the waterfront. Last but not least, Southbay also offers tennis courts, a shuffleboard court, and a playground.

You don’t have to drive far to get to the beaches of Casey Key because the Blackburn Point Bridge is just five minutes away; moreover, you can get virtually all your shopping done at the Casey Key Publix supermarket, which is just a block from Southbay’s entrance.

Amenities of Southbay Yacht & Racquet Club in Osprey

Homes for Sale at Southbay Yacht & Racquet Club in Osprey

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(all data current as of 9/17/2025)

Listing information deemed reliable but not guaranteed. Read full disclaimer.