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  1. Subdivision Like Southbay Yacht Racquet Club
  2. Listing Status = Active
313 Lookout Point Drive
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Details for 313 Lookout Point Drive, OSPREY, FL 34229
Single Family
  1. Price: $5,999,999.00
  2. Price sqft: $870.07 / sqft
  3. Days On Market: 17
  4. Bedrooms: 4
  5. Baths: 5
  6. Garage / Parking Spaces: 6
  7. Bldg sqft: 6896
  8. Acreage: 0.41 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Intracoastal Waterway,Marina in Community
  14. Year Built: 2016
MLS#: A4688995
  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: MICHAEL SAUNDERS & COMPANY
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Bring your yacht. This is Sarasota waterfront living at its most refined. First time on the market, this custom built John Cannon estate is perfectly positioned within Southbay Yacht & Racquet Clubone
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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: $2,249,900.00
  2. Price sqft: $580.32 / sqft
  3. Previous Price: $2,274,900
  4. Last Price Change: 03/27/26
  5. Days On Market: 160
  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 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: $1,995,000.00
  2. Price sqft: $434.07 / sqft
  3. Previous Price: $2,299,000
  4. Last Price Change: 04/19/26
  5. Days On Market: 203
  6. Bedrooms: 3
  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 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. Directly across the street from one of the most exceptional community owned marinas on Floridas west coast, this beautifully renovated waterfront reside
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1527 Buoy Lane
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Details for 1527 Buoy Lane, OSPREY, FL 34229
Single Family
  1. Price: $1,199,000.00
  2. Price sqft: $325.37 / sqft
  3. Days On Market: 17
  4. Bedrooms: 3
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3685
  8. Acreage: 0.27 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 1989
MLS#: A4688266
  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: BRIGHT REALTY
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Beautifully and thoroughly recently updated beach style home in Southbay Yacht and Racquet club featuring 10 foot ceilings. 2026 AC unit, 2024 tile roof, 2023 driveway, cabinets, lighting, appliances,
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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: $895,000.00
  2. Price sqft: $299.03 / sqft
  3. Previous Price: $936,000
  4. Last Price Change: 04/17/26
  5. Days On Market: 163
  6. Bedrooms: 3
  7. Baths: 3
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 2993
  10. Acreage: 0.27 acres
  11. Pool: Yes
  12. Community Pool: Yes
  13. Waterfront: No
  14. 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 Elementary
  6. Middle School: Laurel Nokomis Middle
  7. High School: Venice Senior High
  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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1486 Landview Lane
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Details for 1486 Landview Lane, OSPREY, FL 34229
Single Family
  1. Price: $850,000.00
  2. Price sqft: $281.09 / sqft
  3. Previous Price: $950,000
  4. Last Price Change: 04/12/26
  5. Days On Market: 164
  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 Elementary
  6. Middle School: Laurel Nokomis Middle
  7. High School: Venice Senior High
  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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102 Windward Drive
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Details for 102 Windward Drive, OSPREY, FL 34229
Single Family
  1. Price: $690,000.00
  2. Price sqft: $230.00 / sqft
  3. Previous Price: $750,000
  4. Last Price Change: 04/19/26
  5. Days On Market: 156
  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: $649,500.00
  2. Price sqft: $196.94 / sqft
  3. Previous Price: $749,900
  4. Last Price Change: 03/07/26
  5. Days On Market: 106
  6. Bedrooms: 3
  7. Baths: 2
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 3298
  10. Acreage: 0.30 acres
  11. Pool: No
  12. Community Pool: Yes
  13. Waterfront: No
  14. 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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Price was reduced over $100,000!!! Went pending immediately and then the buyers couldn't secure financing. It is now BACK ON MARKET as of 3/19 and NO INSPECTIONS HAVE BEEN DONE! Located in the desirab
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1355 Southbay Drive
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Details for 1355 Southbay Drive, OSPREY, FL 34229
Rental
  1. Price: $4,500.00
  2. Price sqft: $1.53 / sqft
  3. Days On Market: 99
  4. Bedrooms: 3
  5. Baths: 2
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 2941
  8. Acreage: 0.29 acres
  9. Pool: Yes
  10. Community Pool: Yes
  11. Waterfront: No
  12. Year Built: 1978
MLS#: A4677804
  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: GOLF & BAY PROPERTIES LLC
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Southbay Yacht & Racquet Club where the true Florida lifestyle is alive and well! This three bedroom two bath pool home is located in an active community with unmatched amenities such as an active soc
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