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  1. Subdivision Like Southbay Yacht Racquet Club
  2. Listing Status = Active
180 Lookout Point Drive
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Details for 180 Lookout Point Drive, OSPREY, FL 34229
Single Family
  1. Price: $2,274,900.00
  2. Price sqft: $586.77 / sqft
  3. Previous Price: $2,299,900
  4. Last Price Change: 02/24/26
  5. Days On Market: 108
  6. Bedrooms: 5
  7. Baths: 4
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 3877
  10. Acreage: 0.40 acres
  11. Pool: Yes
  12. Waterfront: No
  13. 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
  6. Middle School: Laurel Nokomis
  7. High School: Venice Senior
  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: $1,995,000.00
  2. Price sqft: $434.07 / sqft
  3. Previous Price: $2,299,000
  4. Last Price Change: 02/18/26
  5. Days On Market: 151
  6. Bedrooms: 4
  7. Baths: 4
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 4596
  10. Acreage: 0.33 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: No
  14. 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
  6. Middle School: Sarasota
  7. High School: Venice Senior
  8. Provided by: PREMIER SOTHEBY'S INTERNATIONAL REALTY
  9. mfrmls
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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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1471 Shoal Way
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Details for 1471 Shoal Way, OSPREY, FL 34229
Single Family
  1. Price: $1,499,000.00
  2. Price sqft: $402.09 / sqft
  3. Days On Market: 7
  4. Bedrooms: 4
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3728
  8. Acreage: 0.43 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 1985
MLS#: A4683702
  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: DALTON WADE INC
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One or more photo(s) has been virtually staged. This exceptional residence truly checks every box. Designed by a renowned architect for his own family, 1471 Shoal Way is a masterclass in thoughtful d
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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. Previous Price: $1,150,000
  4. Last Price Change: 01/22/26
  5. Days On Market: 181
  6. Bedrooms: 3
  7. Baths: 3
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 4247
  10. Acreage: 0.30 acres
  11. Pool: Yes
  12. Waterfront: No
  13. 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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Attention water lovers... take a look at this home in the highly sought after community of Southbay Yacht & Racquet Club, where true resort style living awaits. The community offers an impressive arra
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1602 Southbay Drive
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Details for 1602 Southbay Drive, OSPREY, FL 34229
Single Family
  1. Price: $974,900.00
  2. Price sqft: $234.35 / sqft
  3. Previous Price: $999,995
  4. Last Price Change: 02/02/26
  5. Days On Market: 168
  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: $950,000.00
  2. Price sqft: $314.15 / sqft
  3. Previous Price: $995,000
  4. Last Price Change: 02/26/26
  5. Days On Market: 111
  6. Bedrooms: 3
  7. Baths: 2
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 3024
  10. Acreage: 0.24 acres
  11. Pool: Yes
  12. Waterfront: No
  13. 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
  6. Middle School: Laurel Nokomis
  7. High School: Venice Senior
  8. Provided by: EXP REALTY LLC
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Experience refined waterfront living in Southbay, one of the areas most coveted boating communities. This impeccably maintained three bedroom pool residence offers a thoughtful, split bedroom design t
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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: 110
  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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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: 01/08/26
  5. Days On Market: 160
  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
  6. Middle School: Laurel Nokomis
  7. High School: Venice Senior
  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: 01/17/26
  5. Days On Market: 104
  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
  6. Middle School: Laurel Nokomis
  7. High School: Venice Senior
  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: 53
  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
  6. Middle School: Sarasota
  7. High School: Venice Senior
  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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Listings provided courtesy of The Hernando County Association of Realtors MLS.
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Datafeed Last updated on March 3, 2026 @ 12:00 am
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