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180 Lookout Point Drive
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Details for 180 Lookout Point Drive, OSPREY, FL 34229
Single Family
  1. Price: $2,299,900.00
  2. Price sqft: $593.22 / sqft
  3. Days On Market: 68
  4. Bedrooms: 5
  5. Baths: 4
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3877
  8. Acreage: 0.40 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 1986
MLS#: A4672222
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Southbay Yacht Racquet Club
  5. Elementary School: Laurel Nokomis Elementary
  6. Middle School: Laurel Nokomis Middle
  7. High School: Venice Senior High
  8. Provided by: PREMIER SOTHEBY'S INTERNATIONAL REALTY
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One or more photo(s) has been virtually staged. Welcome to 180 Lookout Point Drive in the sought after Southbay Yacht & Racquet Club with deep water marina and available boat slips, the opportunity to
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312 Yacht Harbor Drive
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Details for 312 Yacht Harbor Drive, OSPREY, FL 34229
Single Family
  1. Price: $2,299,000.00
  2. Price sqft: $500.22 / sqft
  3. Days On Market: 111
  4. Bedrooms: 4
  5. Baths: 4
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 4596
  8. Acreage: 0.33 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 1978
MLS#: A4667293
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Southbay Yacht Racquet Club
  5. Elementary School: Laurel Nokomis Elementary
  6. Middle School: Sarasota Middle
  7. High School: Venice Senior High
  8. Provided by: PREMIER SOTHEBY'S INTERNATIONAL REALTY
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One or more photo(s) has been virtually staged. Considered one of the finest community owned marinas on the west coast of Florida, Southbay Yacht & Racquet Club features a seven acre, deep water boat
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1218 Yacht Harbor Drive
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Details for 1218 Yacht Harbor Drive, OSPREY, FL 34229
Single Family
  1. Price: $1,125,000.00
  2. Price sqft: $264.89 / sqft
  3. Days On Market: 142
  4. Bedrooms: 3
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 4247
  8. Acreage: 0.30 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 1980
MLS#: A4663579
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Southbay Yacht Racquet Club
  5. Elementary School: Laurel Nokomis
  6. Middle School: Sarasota
  7. High School: Venice Senior
  8. Provided by: KELLER WILLIAMS ON THE WATER S
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New listing alert in the highly sought after community of Southbay Yacht & Racquet Club, where true resort style living awaits. The community offers an impressive array of amenities, including a marin
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1602 Southbay Drive
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Details for 1602 Southbay Drive, OSPREY, FL 34229
Single Family
  1. Price: $999,995.00
  2. Price sqft: $240.38 / sqft
  3. Previous Price: $995,000
  4. Last Price Change: 12/19/25
  5. Days On Market: 128
  6. Bedrooms: 4
  7. Baths: 4
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 4160
  10. Acreage: 0.31 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 1986
MLS#: A4665288
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Southbay Yacht Racquet Club
  5. Provided by: COMPASS FLORIDA LLC
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Welcome to your slice of Florida paradise! Nestled on a spacious corner lot in the highly sought after Southbay Yacht & Racquet Club, this elegant residence captures the essence of the coastal lifest
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1486 Landview Lane
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Details for 1486 Landview Lane, OSPREY, FL 34229
Single Family
  1. Price: $995,000.00
  2. Price sqft: $329.03 / sqft
  3. Days On Market: 72
  4. Bedrooms: 3
  5. Baths: 2
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3024
  8. Acreage: 0.24 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 1977
MLS#: D6144630
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Southbay Yacht Racquet Club
  5. Elementary School: Laurel Nokomis Elementary
  6. Middle School: Laurel Nokomis Middle
  7. High School: Venice Senior High
  8. Provided by: EXP REALTY LLC
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Welcome to your Boater's Paradise! This well maintained South Bay home is your key to enjoy one of the best neighborhoods in the area. This three bedroom pool home has the perfect layout with the pri
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172 Sea Anchor Drive
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Details for 172 Sea Anchor Drive, OSPREY, FL 34229
Single Family
  1. Price: $936,000.00
  2. Price sqft: $312.73 / sqft
  3. Days On Market: 71
  4. Bedrooms: 3
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 2993
  8. Acreage: 0.27 acres
  9. Pool: Yes
  10. Community Pool: Yes
  11. Waterfront: No
  12. Year Built: 1977
MLS#: A4671745
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Southbay Yacht Racquet Club
  5. Elementary School: Laurel Nokomis
  6. Middle School: Laurel Nokomis
  7. High School: Venice Senior
  8. Provided by: GOLF & BAY PROPERTIES LLC
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Amazing home with many improvements ideally located in a sought after marina community. This beautifully updated 3 bedroom 3 bath residence has been thoughtfully enhanced for comfort, style and easy l
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238 Lookout Point Drive
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Details for 238 Lookout Point Drive, OSPREY, FL 34229
Single Family
  1. Price: $895,000.00
  2. Price sqft: $244.54 / sqft
  3. Days On Market: 73
  4. Bedrooms: 3
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3660
  8. Acreage: 0.28 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 1981
MLS#: A4671468
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Southbay Yacht Racquet Club
  5. Elementary School: Laurel Nokomis Elementary
  6. Middle School: Venice Area Middle
  7. High School: Venice Senior High
  8. Provided by: COLDWELL BANKER REALTY
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This is an outstanding Southbay residence and a fantastic opportunity to live in one of the best boating communities on the Southwest coast of Florida. This home has been updated with a gourmet custo
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123 Windward Drive
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Details for 123 Windward Drive, OSPREY, FL 34229
Single Family
  1. Price: $820,000.00
  2. Price sqft: $308.16 / sqft
  3. Previous Price: $850,000
  4. Last Price Change: 01/18/26
  5. Days On Market: 120
  6. Bedrooms: 3
  7. Baths: 2
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 2661
  10. Acreage: 0.25 acres
  11. Pool: No
  12. Waterfront: No
  13. Year Built: 1979
MLS#: A4656319
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Southbay Yacht Racquet Club
  5. Elementary School: Laurel Nokomis Elementary
  6. Middle School: Laurel Nokomis Middle
  7. High School: Venice Senior High
  8. Provided by: WILLIAM RAVEIS REAL ESTATE
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PRICE IMPROVEMENT! This immaculate and meticulously maintained 3 bedroom, 2 bath home in the sought after Southbay Yacht & Racquet community is move in ready and packed with beautiful updates. The ope
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102 Windward Drive
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Details for 102 Windward Drive, OSPREY, FL 34229
Single Family
  1. Price: $750,000.00
  2. Price sqft: $250.00 / sqft
  3. Previous Price: $800,000
  4. Last Price Change: 01/18/26
  5. Days On Market: 64
  6. Bedrooms: 3
  7. Baths: 3
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 3000
  10. Acreage: 0.36 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 1986
MLS#: A4671793
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Southbay Yacht Racquet Club
  5. Elementary School: Laurel Nokomis Elementary
  6. Middle School: Laurel Nokomis Middle
  7. High School: Venice Senior High
  8. Provided by: WILLIAM RAVEIS REAL ESTATE
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NEW PRICE! Located in the desirable Southbay Yacht & Racquet Club, this 3 bedroom, 2.5 bath pool home with mature landscaping offers a functional layout and excellent community amenities. The home fea
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186 Windward Drive
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Details for 186 Windward Drive, OSPREY, FL 34229
Single Family
  1. Price: $749,900.00
  2. Price sqft: $227.38 / sqft
  3. Days On Market: 14
  4. Bedrooms: 3
  5. Baths: 2
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3298
  8. Acreage: 0.30 acres
  9. Pool: No
  10. Community Pool: Yes
  11. Waterfront: No
  12. Year Built: 1983
MLS#: N6142087
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Southbay Yacht Racquet Club
  5. Elementary School: Laurel Nokomis Elementary
  6. Middle School: Sarasota Middle
  7. High School: Venice Senior High
  8. Provided by: KELLER WILLIAMS ON THE WATER S
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Located in the desirable Southbay Yacht & Racquet Club, this 3 bedroom, 2 bath residence offers a split bedroom layout, unique community amenities, NEW ROOF in 2022, and plenty of room for a private p
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