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  1. Zipcode = 34229
  2. Listing Status = Active
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: 328
  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
Details for 121 Casey Key Road, OSPREY, FL 34229
Single Family
  1. Price: $6,800,000.00
  2. Price sqft: $984.65 / sqft
  3. Days On Market: 117
  4. Bedrooms: 4
  5. Baths: 6
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 6906
  8. Acreage: 0.49 acres
  9. Pool: Yes
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: Beach Front,Gulf/Ocean
  13. 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
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: 71
  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
Details for 144 Casey Key Road, Osprey, FL 34229
Single Family
  1. Price: $5,495,000.00
  2. Price sqft: $512.50 / sqft
  3. Days On Market: 3
  4. Bedrooms: 4
  5. Baths: 6
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 10722
  8. Acreage: 0.55 acres
  9. Pool: Yes
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: BayAccess,BeachAccess,GulfAccess
  13. Year Built: 2003
MLS#: A4679060
  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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  10. DMCA Notice
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
Details for 144 Casey Key Road, OSPREY, FL 34229
Single Family
  1. Price: $5,495,000.00
  2. Price sqft: $512.50 / sqft
  3. Days On Market: 3
  4. Bedrooms: 4
  5. Baths: 6
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 10722
  8. Acreage: 0.55 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Bay/Harbor
  14. Year Built: 2003
MLS#: A4679060
  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
  9. mfrmls
  10. DMCA Notice
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
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: 11/19/25
  5. Days On Market: 174
  6. Bedrooms: 4
  7. Baths: 6
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 10722
  10. Acreage: 0.55 acres
  11. Pool: Yes
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: BayAccess,BeachAccess,GulfAccess
  15. 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
  9. Provided through
  10. DMCA Notice
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
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: 174
  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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  10. DMCA Notice
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
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: 134
  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
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: 102
  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
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: 48
  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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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. Set on 0.68 acres with 131 feet of Sarasota Bay f