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You are here: Home / Southbay Homes for Sale | Osprey Florida

Southbay Homes for Sale | Osprey Florida

Southbay is a well-established waterfront community located in Osprey, just south of Sarasota. Inspired by the early vision of circus magnate John Ringling, this neighborhood reflects the concept of resort-style Florida living with boating access, beautiful natural surroundings, and spacious residential properties.

Originally developed in the mid-1970s as the Southbay Yacht and Racquet Club, the community occupies the former site of Floridaland, a once-popular amusement park that closed after Walt Disney World opened in Orlando. Today, the area has transformed into a scenic waterfront neighborhood offering elegant homes, marina access, and a relaxed coastal lifestyle.

Southbay Homes in Osprey

Southbay is located west of the Tamiami Trail and south of Blackburn Point Road in the southwestern section of Osprey. The neighborhood sits along Dryman Bay with views toward Casey Key, creating a beautiful waterfront setting surrounded by nature.

The community is buffered by nearby parks such as Shoreland Park and Blackburn Point Park, which help maintain a peaceful atmosphere. Homes in Southbay were primarily built as Florida ranch-style residences, though many have been renovated or expanded to incorporate Mediterranean and Caribbean-inspired architectural elements.

  • Established waterfront community in Osprey
  • Originally developed in the mid-1970s
  • Large homesites with mature landscaping
  • Architectural styles include Florida ranch, Mediterranean, and Caribbean
  • Many homes renovated with modern upgrades
  • Water views toward Dryman Bay and Casey Key

Southbay Yacht and Racquet Club Amenities

Southbay offers an impressive collection of amenities designed for an active coastal lifestyle. As a yacht club community, boating and waterfront recreation are central to life in the neighborhood.

  • Private marina with boat slips
  • Clubhouse with ballroom and catering kitchen
  • Fitness center and sauna
  • Resort-style swimming pool
  • Tennis courts and shuffleboard
  • Playground and community gathering areas
  • Private waterfront park and walking trails
Southbay Yacht & Racquet Club in Osprey Homes for Sale 2
Southbay Yacht and Racquet Club Osprey Homes for Sale
Southbay Yacht & Racquet Club in Osprey Entrance Sign
Southbay Yacht and Racquet Club Osprey Homes for Sale
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

Lookout Point, the neighborhood’s private waterfront park, offers scenic walking and biking paths that stretch for miles along the bay, making it a favorite gathering spot for residents.

Living in Osprey, Florida

Southbay offers residents the convenience of a central location between Sarasota and Venice. Everyday shopping and dining options are nearby, including the Publix supermarket just a short distance from the neighborhood entrance.

Beach lovers can reach the beautiful Gulf shoreline quickly thanks to the nearby Blackburn Point Bridge, which connects Osprey to the beaches of Casey Key. The arts, dining, and entertainment options of Downtown Sarasota are also a short drive to the north.

Southbay Homes for Sale in Osprey

With its waterfront setting, marina amenities, and spacious homes, Southbay remains one of the most desirable neighborhoods in Osprey. View current Southbay homes for sale below if inventory is available.

1527 BUOY LANE OSPREY FL 34229
New Listing - a week on site
1 / 52
$1,199,000
Single Family Residence For Sale
Active
3
BEDS
3
TOTAL BATHS
2,830
SQFT
1527 BUOY LANE
OSPREY, FL 34229
SOUTHBAY YACHT & RACQUET CLUB Subdivision
313 LOOKOUT POINT DRIVE OSPREY FL 34229
New Listing - a week on site
1 / 100
$5,999,999
Single Family Residence For Sale
Active
4
BEDS
5
TOTAL BATHS
5,337
SQFT
313 LOOKOUT POINT DRIVE
OSPREY, FL 34229
SOUTHBAY YACHT & RACQUET CLUB Subdivision
186 WINDWARD DRIVE OSPREY FL 34229
1 / 93
$649,500
Single Family Residence For Sale
Active
3
BEDS
2
TOTAL BATHS
2,505
SQFT
186 WINDWARD DRIVE
OSPREY, FL 34229
SOUTHBAY YACHT & RACQUET CLUB Subdivision
102 WINDWARD DRIVE OSPREY FL 34229
Open House Sun, Apr 19, 1 PM
1 / 78
$690,000
Single Family Residence For Sale
Active
3
BEDS
3
TOTAL BATHS
2,134
SQFT
102 WINDWARD DRIVE
OSPREY, FL 34229
SOUTHBAY YACHT & RACQUET CLUB Subdivision
180 LOOKOUT POINT DRIVE OSPREY FL 34229
Price Change - 3 weeks ago
1 / 70
$2,249,900
Single Family Residence For Sale
Active
5
BEDS
4
TOTAL BATHS
3,236
SQFT
180 LOOKOUT POINT DRIVE
OSPREY, FL 34229
SOUTHBAY YACHT & RACQUET CLUB Subdivision
172 SEA ANCHOR DRIVE OSPREY FL 34229
1 / 48
$895,000
Single Family Residence For Sale
Active
3
BEDS
3
TOTAL BATHS
2,283
SQFT
172 SEA ANCHOR DRIVE
OSPREY, FL 34229
SOUTHBAY YACHT & RACQUET CLUB Subdivision
1486 LANDVIEW LANE OSPREY FL 34229
1 / 78
$850,000
Single Family Residence For Sale
Active
3
BEDS
2
TOTAL BATHS
1,869
SQFT
1486 LANDVIEW LANE
OSPREY, FL 34229
SOUTHBAY YACHT & RACQUET CLUB Subdivision
312 YACHT HARBOR DRIVE OSPREY FL 34229
Open House Sun, Apr 19, 1 PM
1 / 69
$1,995,000
Single Family Residence For Sale
Active
3
BEDS
4
TOTAL BATHS
2,572
SQFT
312 YACHT HARBOR DRIVE
OSPREY, FL 34229
SOUTHBAY YACHT & RACQUET CLUB Subdivision

Southbay Osprey FAQ

Where is Southbay located?

Southbay is located in Osprey, Florida, just south of Blackburn Point Road and west of the Tamiami Trail.

What type of homes are in Southbay?

The neighborhood features Florida ranch homes along with Mediterranean and Caribbean-style residences, many of which have been renovated over the years.

Does Southbay have boating amenities?

Yes. Southbay includes a private marina and yacht club facilities for residents who enjoy boating and waterfront recreation.

What amenities are available in Southbay?

Residents enjoy a clubhouse, swimming pool, tennis courts, fitness center, waterfront park, walking trails, and marina access.

How close is Southbay to Casey Key beaches?

The Blackburn Point Bridge provides quick access to the beaches of Casey Key, which are only a few minutes away.

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The Wendy Lynn Group Sarasota exp Realty



  • 1300 Main Street, Sarasota, FL 34236

  • 941-421-7375

  • info@sunnysarasotahomes.com

Osprey Neighborhoods

  • Bay Street
  • Sorrento Shores
  • Southbay YRC

Areas We Serve

  • Anna Maria
  • Bird Key
  • Bradenton
  • Bradenton Beach
  • Casey Key
  • Cortez
  • Downtown Sarasota
  • Ellenton
  • Englewood
  • Golden Gate
  • Holmes Beach
  • Lakewood Ranch
  • Lido Key
  • Longboat Key
  • Myakka City
  • Nokomis
  • North Port
  • Osprey
  • Palmer Ranch
  • Palmetto
  • Parrish
  • Sarasota
  • Siesta Key
  • South Hillsborough
  • Terra Ceia
  • University Park
  • Venice
  • West of the Trail

Things to do in Osprey Florida

https://www.youtube.com/watch?v=JJT1XzDeJLU

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The Wendy Lynn Group Sarasota exp Realty

  • 1300 Main Street, Sarasota, FL 34236
  • 941-421-7375
  • info@sunnysarasotahomes.com

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