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You are here: Home / Osprey / Southbay in Osprey : Yacht & Racquet Club w Homes for Sale & Amenities

Southbay in Osprey : Yacht & Racquet Club w Homes for Sale & Amenities

by Josh Lynn

One of the most famous real estate landmarks of southern Sarasota County was once a popular amusement park. Located near the entrance of Oscar Scherer State Park in Osprey, Southbay is an established community that combines a marina with other amenities plus great real estate to deliver a resort-like experience.

Southbay is often mentioned as being one of the most attractive neighborhoods for boaters in Southwest Florida. Whether you are into motor or sailing vessels, you will find the community marina to be a prime docking space with easy access to the Intracoastal Waterway. Even if you are not into boating or fishing, Southbay provides quite a few other amenities that you will certainly enjoy: as tennis courts, a fitness center, a grand clubhouse with lounge spaces that can be reserved for social events, a playground for children, shuffleboard courts, a swimming pool, five miles of walking trails, a library, and even a community park where you can watch the sunset over the Gulf of Mexico.

Architectural styles at Southbay range from Florida ranch-style homes from the early 1980s to Caribbean and from Mediterranean revival to Modern Coastal. Floor plans tend to be larger than 1,800 square feet and have at least three bedrooms, two bathrooms, and two-car garages. Pricing largely depends on the location of the property; some of them are waterfront mansions that offer gorgeous views of Casey Key.

Southbay is a neighborhood where you will never have to worry about depreciation. From time to time, a bargain listing may be closed by a seller in a rush, but value appreciation is constant. Even though this is a fairly large community with more than 350 dwellings, only a handful of them come on the market each month, and they do not take long to get to the closing table. As of May 2020, the lower price range for a three-bedroom Florida ranch was $425K, but more attractive offers are known to become available.

Nokomis Beach is close enough for a bike ride from the Southbay entrance, which happens to be right next to a shopping center where you will find stores such as Publix and Dollar Tree. As previously mentioned, the main entrance to Oscar Scherer State Park is just down the road.

Slideshow of Southbay in Osprey Yacht & Racquet Club

Southbay Yacht & Racquet Club in Osprey Homes for Sale 2
Southbay Yacht & Racquet Club in Osprey Homes for Sale
Southbay Yacht & Racquet Club in Osprey Entrance Sign
Southbay Yacht & Racquet Club in Osprey Pool
Southbay Yacht & Racquet Club in Osprey Spa 2
Southbay Yacht & Racquet Club in Osprey Marina
Southbay Yacht & Racquet Club in Osprey Marina 3
Southbay Yacht & Racquet Club in Osprey Tennis Courts

Homes for Sale at Southbay Yacht & Racquet Club in Osprey

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  • 180 Lookout Point Drive, Osprey, FL
    180 Lookout Point Drive
    Osprey, FL
    Photo of 180 Lookout Point Drive, Osprey, FL 34229 (MLS # A4653130)
    $2,299,900
    • Lot Size
      17,424 sqft

    • Home Size
      3,236 sqft

    • Beds
      5 Beds

    • Baths
      4 Baths

    • Year Built
      1986

    • Days on Market
      4

    View Virtual Tour
  • 1527 Buoy Lane, Osprey, FL
    1527 Buoy Lane
    Osprey, FL
    Photo of 1527 Buoy Lane, Osprey, FL 34229 (MLS # A4654172)
    $1,339,000
    • Lot Size
      11,762 sqft

    • Home Size
      2,830 sqft

    • Beds
      3 Beds

    • Baths
      3 Baths

    • Year Built
      1989

    • Days on Market
      18

    View Virtual Tour
  • 238 Lookout Point Drive, Osprey, FL
    238 Lookout Point Drive
    Osprey, FL
    Photo of 238 Lookout Point Drive, Osprey, FL 34229 (MLS # A4650720)
    $979,000
    • Lot Size
      12,197 sqft

    • Home Size
      2,676 sqft

    • Beds
      3 Beds

    • Baths
      3 Baths

    • Year Built
      1981

    • Days on Market
      42

  • 172 Sea Anchor Drive, Osprey, FL
    172 Sea Anchor Drive
    Osprey, FL
    Photo of 172 Sea Anchor Drive, Osprey, FL 34229 (MLS # A4650577)
    $997,000
    • Lot Size
      11,762 sqft

    • Home Size
      2,283 sqft

    • Beds
      3 Beds

    • Baths
      3 Baths

    • Year Built
      1977

    • Days on Market
      47

  • 1212 Windward Drive, Osprey, FL
    1212 Windward Drive
    Osprey, FL
    Photo of 1212 Windward Drive, Osprey, FL 34229 (MLS # A4637262)
    $679,900
    • Lot Size
      13,068 sqft

    • Home Size
      1,994 sqft

    • Beds
      3 Beds

    • Baths
      2 Baths

    • Year Built
      1982

    • Days on Market
      143

    View Virtual Tour
  • 312 Yacht Harbor Drive, Osprey, FL
    312 Yacht Harbor Drive
    Osprey, FL
    Photo of 312 Yacht Harbor Drive, Osprey, FL 34229 (MLS # A4631221)
    $2,495,000
    • Lot Size
      14,375 sqft

    • Home Size
      2,572 sqft

    • Beds
      4 Beds

    • Baths
      4 Baths

    • Year Built
      1978

    • Days on Market
      198

    View Virtual Tour
  • 120 Lookout Point Drive, Osprey, FL
    120 Lookout Point Drive
    Osprey, FL
    Photo of 120 Lookout Point Drive, Osprey, FL 34229 (MLS # A4630315)
    $1,199,000
    • Lot Size
      15,682 sqft

    • Home Size
      2,925 sqft

    • Beds
      4 Beds

    • Baths
      3 Baths

    • Year Built
      1985

    • Days on Market
      209

See all Southbay Osprey FL Homes for Sale.
(all data current as of 6/15/2025)

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

 
 

Filed Under: Osprey

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    Photo of 4426 Useppa Drive, Bradenton, FL 34203 (MLS # A4655631)
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    Photo of 4637 Willow Wood Circle #44, Sarasota, FL 34241 (MLS # A4655394)
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    Photo of 520 27th Street W, Bradenton, FL 34205 (MLS # A4655855)
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