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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: 10
  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
  6. Middle School: Laurel Nokomis
  7. High School: Venice Senior
  8. Provided by: MICHAEL SAUNDERS & COMPANY
  9. mfrmls
  10. DMCA Notice
Description
  1. 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
Listing Details and 99 Additional Pictures
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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: 153
  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
  9. mfrmls
  10. DMCA Notice
Description
  1. 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
Listing Details and 69 Additional Pictures
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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: 196
  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
  6. Middle School: Sarasota
  7. High School: Venice Senior
  8. Provided by: PREMIER SOTHEBY'S INTERNATIONAL REALTY
  9. mfrmls
  10. DMCA Notice
Description
  1. 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
Listing Details and 68 Additional Pictures
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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: 10
  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
  6. Middle School: Venice Area
  7. High School: Venice Senior
  8. Provided by: BRIGHT REALTY
  9. mfrmls
  10. DMCA Notice
Description
  1. 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,
Listing Details and 51 Additional Pictures
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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: 03/09/26
  5. Days On Market: 156
  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
  6. Middle School: Laurel Nokomis
  7. High School: Venice Senior
  8. Provided by: GOLF & BAY PROPERTIES LLC
  9. mfrmls
  10. DMCA Notice
Description
  1. 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
Listing Details and 47 Additional Pictures
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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: 03/17/26
  5. Days On Market: 157
  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
  9. mfrmls
  10. DMCA Notice
Description
  1. 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
Listing Details and 77 Additional Pictures
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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: 03/24/26
  5. Days On Market: 149
  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
  9. mfrmls
  10. DMCA Notice
Description
  1. 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
Listing Details and 77 Additional Pictures
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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: 99
  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
  9. mfrmls
  10. DMCA Notice
Description
  1. 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
Listing Details and 92 Additional Pictures
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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: 92
  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
  6. Middle School: Laurel Nokomis
  7. High School: Venice Senior
  8. Provided by: GOLF & BAY PROPERTIES LLC
  9. mfrmls
  10. DMCA Notice
Description
  1. 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
Listing Details and 30 Additional Pictures
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