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  1. Michelle Hill, ABR,AHWD,PA,PSA,REALTOR ®,SFR
  2. Tropic Shores Realty
  3. Mobile: 352.247.2177
  4. 229.834.4988
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  1. Subdivision Like Southbay Yacht
  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: 2
  4. Bedrooms: 4
  5. Baths: 5
  6. Garage / Parking Spaces: 6
  7. Bldg sqft: 6896
  8. Acreage: 0.41 acres
  9. Pool: Yes
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: IntracoastalAccess
  13. 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. Provided through
  10. DMCA Notice
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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313 Lookout Point Drive
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Active
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: 2
  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
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: 145
  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
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: 188
  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
  10. DMCA Notice
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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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: 44
  4. Bedrooms: 4
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3728
  8. Acreage: 0.43 acres
  9. Pool: Yes
  10. Community Pool: 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
  9. Provided through
  10. DMCA Notice
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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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: 1
  4. Bedrooms: 3
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3685
  8. Acreage: 0.27 acres
  9. Pool: Yes
  10. Community Pool: 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. Provided through
  10. DMCA Notice
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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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: 205
  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
  6. mfrmls
  7. DMCA Notice
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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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: 147
  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
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: 03/17/26
  5. Days On Market: 148
  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
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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: 03/24/26
  5. Days On Market: 141
  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
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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