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  1. City = Osprey
1216 Casey Key Road
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Details for 1216 Casey Key Road, OSPREY, FL 34229
Single Family
  1. Price: $11,750,000.00
  2. Price sqft: $756.99 / sqft
  3. Days On Market: 20
  4. Bedrooms: 5
  5. Baths: 8
  6. Garage / Parking Spaces: 4
  7. Bldg sqft: 15522
  8. Acreage: 1.10 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Bay/Harbor,Beach Front,Gulf/Ocean,Gulf/Ocean to Bay,Intracoastal Waterway
  14. Year Built: 1999
MLS#: A4643654
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Casey Key
  5. Elementary School: Laurel Nokomis Elementary
  6. Middle School: Laurel Nokomis Middle
  7. High School: Venice Senior High
  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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144 Casey Key Road
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Details for 144 Casey Key Road, OSPREY, FL 34229
Single Family
  1. Price: $6,950,000.00
  2. Price sqft: $648.20 / sqft
  3. Previous Price: $7,095,000
  4. Last Price Change: 03/20/25
  5. Days On Market: 69
  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#: A4636387
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Casey Key
  5. Elementary School: Laurel Nokomis Elementary
  6. Middle School: Laurel Nokomis Middle
  7. High School: Venice Senior High
  8. Provided by: EXP REALTY LLC
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Priced reduced! Welcome to this extraordinary waterfront estate on exclusive Casey Key, showcasing panoramic views of Little Sarasota Bay and vistas of the Gulf of Mexico. Built to the latest hurrican
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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: $5,300,000.00
  2. Price sqft: $774.74 / sqft
  3. Days On Market: 4
  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#: A4639897
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: The Oaks
  5. Elementary School: Laurel Nokomis Elementary
  6. Middle School: Sarasota Middle
  7. High School: Venice Senior High
  8. Provided by: COLDWELL BANKER REALTY
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One or more photo(s) has been virtually staged. Indulge in the epitome of sophistication and timeless elegance with this magnificent luxury home with 4 bedrooms, 5 full and 1 half bath. Meticulously c
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1049 Casey Key Road
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Details for 1049 Casey Key Road, OSPREY, FL 34229
Single Family
  1. Price: $4,750,000.00
  2. Price sqft: $1,408.24 / sqft
  3. Days On Market: 16
  4. Bedrooms: 3
  5. Baths: 3
  6. Garage / Parking Spaces: 5
  7. Bldg sqft: 3373
  8. Acreage: 1.06 acres
  9. Pool: No
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: Bay/Harbor,Gulf/Ocean,Gulf/Ocean to Bay,Intracoastal Waterway
  13. Year Built: 1990
MLS#: N6137711
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Casey Key
  5. Elementary School: Laurel Nokomis Elementary
  6. Middle School: Laurel Nokomis Middle
  7. High School: Venice Senior High
  8. Provided by: PREMIER SOTHEBYS INTL REALTY
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Seize the opportunity to own a piece of paradise on the exclusive North Casey Key. This sprawling one plus acre estate, with 107 feet of pristine gulf frontage, a walkable sandy beach, on a private ro
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426 Casey Key Road
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Details for 426 Casey Key Road, OSPREY, FL 34229
Single Family
  1. Price: $4,500,000.00
  2. Price sqft: $1,445.09 / sqft
  3. Previous Price: $4,700,000
  4. Last Price Change: 09/23/24
  5. Days On Market: 552
  6. Bedrooms: 3
  7. Baths: 2
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 3114
  10. Acreage: 0.94 acres
  11. Pool: Yes
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: Bay/Harbor,Beach Front,Gulf/Ocean to Bay,Intracoastal Waterway
  15. Year Built: 1992
MLS#: A4583445
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Casey Key
  5. Elementary School: Laurel Nokomis Elementary
  6. Middle School: Laurel Nokomis Middle
  7. High School: Venice Senior High
  8. Provided by: PREMIER SOTHEBYS INTL REALTY
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Gulf to Bay on North Casey Key the perfect location! Panoramic views of Little Sarasota Bay to the east and a beachfront lot on the west. Original cypress tongue and groove ceilings and beautiful oak
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275 Lookout Point Drive
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Details for 275 Lookout Point Drive, OSPREY, FL 34229
Single Family
  1. Price: $4,250,000.00
  2. Price sqft: $546.20 / sqft
  3. Days On Market: 90
  4. Bedrooms: 5
  5. Baths: 5
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 7781
  8. Acreage: 0.38 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Bay/Harbor,Intracoastal Waterway
  14. Year Built: 2007
MLS#: A4632453
  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 SOTHEBYS INTL REALTY
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This stunning waterfront residence in Southbay Yacht and Racquet Club is a gem on Floridas Gulf Coast where boats are accommodated in a deep water marina for low fees. Boasting over 135 feet of water
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854 Macewen Drive
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Details for 854 Macewen Drive, OSPREY, FL 34229
Single Family
  1. Price: $4,195,000.00
  2. Price sqft: $360.09 / sqft
  3. Previous Price: $4,495,000
  4. Last Price Change: 02/18/25
  5. Days On Market: 144
  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#: A4627698
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Oaks 2 Ph 2
  5. Elementary School: Laurel Nokomis Elementary
  6. Middle School: Laurel Nokomis Middle
  7. High School: Venice Senior High
  8. Provided by: GENEROUS PROPERTY
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One or more photo(s) has been virtually staged. **newly renovated, spacious, golf course estate** boasts over 9,000sf and is situated on a prominent, private cul de sac lot of over 3/4 acres. Expansiv
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412 Cezanne Drive
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Details for 412 Cezanne Drive, OSPREY, FL 34229
Single Family
  1. Price: $3,995,000.00
  2. Price sqft: $622.27 / sqft
  3. Previous Price: $4,250,000
  4. Last Price Change: 11/07/24
  5. Days On Market: 203
  6. Bedrooms: 4
  7. Baths: 5
  8. Garage / Parking Spaces: 6
  9. Bldg sqft: 6420
  10. Acreage: 1.19 acres
  11. Pool: Yes
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: Canal - Saltwater,Creek
  15. Year Built: 1975
MLS#: N6134456
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Sorrento Shores
  5. Elementary School: Laurel Nokomis Elementary
  6. Middle School: Laurel Nokomis Middle
  7. High School: Venice Senior High
  8. Provided by: CORNERSTONE R.E OF SW FL
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Nestled in the serene and highly sought after Sorrento Shores community, this exceptional and breathtaking property offers unparalleled waterfront living on over an acre of land (1.19 acres) along the
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5 Casey Key Road
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Details for 5 Casey Key Road, OSPREY, FL 34229
Single Family
  1. Price: $3,775,000.00
  2. Price sqft: $1,073.97 / sqft
  3. Previous Price: $3,875,000
  4. Last Price Change: 03/09/25
  5. Days On Market: 179
  6. Bedrooms: 4
  7. Baths: 4
  8. Garage / Parking Spaces: 1
  9. Bldg sqft: 3515
  10. Acreage: 0.57 acres
  11. Pool: No
  12. Waterfront: No
  13. Year Built: 1969
MLS#: N6134765
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Casey Key
  5. Elementary School: Laurel Nokomis Elementary
  6. Middle School: Sarasota Middle
  7. High School: Venice Senior High
  8. Provided by: AYERS AND ASSOCIATES REAL ESTATE
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REDUCED! Iconic Gulf front Mid Century Modern gated residence on Casey Key embodies the true essence of casual coastal living, offering an unparalleled retreat for the soul. The moment you step throug
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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: $3,275,000.00
  2. Price sqft: $523.41 / sqft
  3. Previous Price: $2,375,000
  4. Last Price Change: 11/22/24
  5. Days On Market: 126
  6. Bedrooms: 3
  7. Baths: 5
  8. Garage / Parking Spaces: 4
  9. Bldg sqft: 6257
  10. Acreage: 0.37 acres
  11. Pool: No
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: Canal - Saltwater
  15. Year Built: 2011
MLS#: N6135539
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Sorrento Shores
  5. Elementary School: Laurel Nokomis Elementary
  6. Middle School: Sarasota Middle
  7. High School: Venice Senior High
  8. Provided by: RE/MAX PALM REALTY OF VENICE
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If you are ready to retreat to paradise, look no more. This home is amazing. Located in a very desirable area in Sorrento Shores, Osprey is on a 200 foot, wide canal frontage. You can enjoy the scenic
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Tropic Shores Realty - Crystal River
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Listings provided courtesy of The Hernando County Association of Realtors MLS.
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Listing Data ©2025 Royal Palm Coast Realtor® Association
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