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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: 34
    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
    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: 176
    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
    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
    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: 04/19/26
    5. Days On Market: 219
    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
    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
    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: 33
    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
    9. mfrmls
    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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    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: 179
    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
    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
    Listing Details and 47 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: $599,900.00
    2. Price sqft: $181.90 / sqft
    3. Previous Price: $649,500
    4. Last Price Change: 05/07/26
    5. Days On Market: 122
    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 Elementary
    6. Middle School: Sarasota Middle
    7. High School: Venice Senior High
    8. Provided by: KELLER WILLIAMS ON THE WATER S
    9. mfrmls
    10. DMCA Notice
    Price was dropped $50,000 on 5/7! Survey and pool quote are available! Located in the desirable Southbay Yacht & Racquet Club, this 3 bedroom, 2 bath residence offers a split bedroom layout, unique co
    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: 115
    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
    9. mfrmls
    10. DMCA Notice
    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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    Listings provided courtesy of The Hernando County Association of Realtors MLS.
    Listing Data ©2026 REALTOR® Association of Citrus County
    The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
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    Datafeed Last updated on May 11, 2026 @ 12:00 am
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