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  1. City = Osprey
  2. Listing Status = Active
1216 Casey Key Road
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Details for 1216 Casey Key Road, OSPREY, FL 34229
Single Family
  1. Price: $10,750,000.00
  2. Price sqft: $692.57 / sqft
  3. Previous Price: $11,750,000
  4. Last Price Change: 01/10/26
  5. Days On Market: 364
  6. Bedrooms: 5
  7. Baths: 8
  8. Garage / Parking Spaces: 4
  9. Bldg sqft: 15522
  10. Acreage: 1.10 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: Yes
  14. Wateraccess: Yes
  15. Waterfront Type: Bay/Harbor,Beach Front,Gulf/Ocean,Gulf/Ocean to Bay,Intracoastal Waterway
  16. Year Built: 1999
MLS#: A4643654
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Casey Key
  5. Elementary School: Laurel Nokomis
  6. Middle School: Laurel Nokomis
  7. High School: Venice Senior
  8. Provided by: PREMIER SOTHEBYS INTL REALTY
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This classically designed estate is privately positioned on north end of Casey Key, considered among the most treasured addresses in Sarasota County. The property spans from a sandy walking beach on t
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121 Casey Key Road
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Details for 121 Casey Key Road, OSPREY, FL 34229
Single Family
  1. Price: $6,800,000.00
  2. Price sqft: $984.65 / sqft
  3. Previous Price: $7,100,000
  4. Last Price Change: 01/29/26
  5. Days On Market: 154
  6. Bedrooms: 4
  7. Baths: 6
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 6906
  10. Acreage: 0.49 acres
  11. Pool: Yes
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: Beach Front,Gulf/Ocean
  15. Year Built: 1969
MLS#: A4667263
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Casey Key
  5. Elementary School: Laurel Nokomis
  6. Middle School: Laurel Nokomis
  7. High School: Venice Senior
  8. Provided by: DOUGLAS ELLIMAN
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Newly Remodeled Gulf Front Mediterranean Villa on Casey Key Framed by the pristine natural beauty of North Casey Key, this Spanish Mediterranean beachfront estate is perfectly positioned along one of
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730 Sarabay Road
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Details for 730 Sarabay Road, OSPREY, FL 34229
Single Family
  1. Price: $5,495,000.00
  2. Price sqft: $673.74 / sqft
  3. Days On Market: 108
  4. Bedrooms: 4
  5. Baths: 6
  6. Garage / Parking Spaces: 7
  7. Bldg sqft: 8156
  8. Acreage: 2.00 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Bay/Harbor,Intracoastal Waterway
  14. Year Built: 2011
MLS#: A4672618
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Sarabay Acres
  5. Provided by: ROBERT SLACK LLC
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Premier Intracoastal Estate in Osprey 4 Bedrooms | 6 Bathrooms | 6,308 Sq. Ft. | 2 Waterfront Acres A rare opportunity to own two acres of private waterfront property in Sarasota, 730 Sarabay is a
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144 Casey Key Road
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Details for 144 Casey Key Road, OSPREY, FL 34229
Single Family
  1. Price: $5,495,000.00
  2. Price sqft: $512.50 / sqft
  3. Previous Price: $5,990,000
  4. Last Price Change: 01/21/26
  5. Days On Market: 211
  6. Bedrooms: 4
  7. Baths: 6
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 10722
  10. Acreage: 0.55 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: Yes
  14. Wateraccess: Yes
  15. Waterfront Type: Bay/Harbor
  16. Year Built: 2003
MLS#: A4660004
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Casey Key
  5. Elementary School: Laurel Nokomis
  6. Middle School: Laurel Nokomis
  7. High School: Venice Senior
  8. Provided by: DOUGLAS ELLIMAN
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Located on the exclusive stretch of North Casey Key, this private waterfront estate offers a rare blend of resort style living, protected boating water, and direct Gulf beach access in one of Sarasota
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101 Osprey Point Drive
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Details for 101 Osprey Point Drive, OSPREY, FL 34229
Single Family
  1. Price: $5,000,000.00
  2. Price sqft: $730.89 / sqft
  3. Days On Market: 171
  4. Bedrooms: 4
  5. Baths: 6
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 6841
  8. Acreage: 0.93 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Lake Front
  14. Year Built: 1985
MLS#: A4664424
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: The Oaks
  5. Elementary School: Laurel Nokomis
  6. Middle School: Sarasota
  7. High School: Venice Senior
  8. Provided by: DOUGLAS ELLIMAN
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A grand estate where timeless design meets lakefront tranquility, 101 Osprey Point Drive offers refined living within the private gates of The Oaks Bayside. Designed by architect Bo MacEwen, this one
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854 Casey Key Road
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Details for 854 Casey Key Road, OSPREY, FL 34229
Single Family
  1. Price: $4,750,000.00
  2. Price sqft: $830.86 / sqft
  3. Days On Market: 8
  4. Bedrooms: 4
  5. Baths: 4
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 5717
  8. Acreage: 1.49 acres
  9. Pool: No
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: Beach Front,Gulf/Ocean to Bay,Intracoastal Waterway
  13. Year Built: 1975
MLS#: N6143043
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Provided by: POTTER TRINITY
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On the quiet and coveted stretch of North Casey Key, where century old oaks meet the shoreline, and the land unfolds uninterrupted from Gulf to bay, this extraordinary 1.5 acre estate offers a rare op
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324 Bayshore Drive
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Details for 324 Bayshore Drive, OSPREY, FL 34229
Single Family
  1. Price: $4,250,000.00
  2. Price sqft: $533.18 / sqft
  3. Days On Market: 11
  4. Bedrooms: 4
  5. Baths: 5
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 7971
  8. Acreage: 0.47 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Bay/Harbor
  14. Year Built: 2000
MLS#: A4683138
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Bay Acres Resub
  5. Elementary School: Laurel Nokomis
  6. Middle School: Laurel Nokomis
  7. High School: Venice Senior
  8. Provided by: MICHAEL SAUNDERS & COMPANY
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Big bay views surround you from this exquisitely updated waterfront estate. Welcome to 324 Bayshore Drive, a property of nearly half an acre set on a large, open stretch of the bay with easy access to
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854 Macewen Drive
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Details for 854 Macewen Drive, OSPREY, FL 34229
Single Family
  1. Price: $3,890,000.00
  2. Price sqft: $333.91 / sqft
  3. Previous Price: $3,950,000
  4. Last Price Change: 01/28/26
  5. Days On Market: 139
  6. Bedrooms: 4
  7. Baths: 6
  8. Garage / Parking Spaces: 4
  9. Bldg sqft: 11650
  10. Acreage: 0.78 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: No
  14. Year Built: 2003
MLS#: A4668918
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Oaks 2 Ph 2
  5. Elementary School: Laurel Nokomis
  6. Middle School: Laurel Nokomis
  7. High School: Venice Senior
  8. Provided by: COLDWELL BANKER REALTY
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One or more photo(s) has been virtually staged. Set on a private cul de sac within The Oaks, this revitalized estate captures the essence of elegant Florida living. From the moment you enter, the home
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1042 Casey Key Road
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Details for 1042 Casey Key Road, OSPREY, FL 34229
Single Family
  1. Price: $3,750,000.00
  2. Price sqft: $572.00 / sqft
  3. Days On Market: 85
  4. Bedrooms: 4
  5. Baths: 5
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 6556
  8. Acreage: 0.68 acres
  9. Pool: Yes
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: Bay/Harbor
  13. Year Built: 1995
MLS#: A4674771
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Palmer
  5. Elementary School: Pine View
  6. Middle School: Pine View
  7. High School: Pine View
  8. Provided by: COLDWELL BANKER REALTY
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One or more photo(s) has been virtually staged. If your dream is to create a place where generations can gather, relax, and make lasting memories, this Casey Key estate is ready to welcome you home. S
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135 Tina Island Drive
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Details for 135 Tina Island Drive, OSPREY, FL 34229
Single Family
  1. Price: $3,300,000.00
  2. Price sqft: $1,283.05 / sqft
  3. Previous Price: $3,350,000
  4. Last Price Change: 01/23/26
  5. Days On Market: 170
  6. Bedrooms: 3
  7. Baths: 5
  8. Garage / Parking Spaces: 4
  9. Bldg sqft: 2572
  10. Acreage: 0.37 acres
  11. Pool: No
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: Canal Front
  15. Year Built: 1965
MLS#: A4665474
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Sorrento Shores
  5. Elementary School: Laurel Nokomis
  6. Middle School: Laurel Nokomis
  7. High School: Venice Senior
  8. Provided by: FLATFEE.COM
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Retreat to paradise in this stunning waterfront home, built new in 2011, in highly sought after Sorrento Shores, Osprey. Perfectly situated on 210 feet of wide canal frontage, this residence offers de
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Tropic Shores Realty - Crystal River
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