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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: 01/12/26
  5. Days On Market: 412
  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 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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121 Casey Key Road
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Details for 121 Casey Key Road, OSPREY, FL 34229
Single Family
  1. Price: $6,475,000.00
  2. Price sqft: $937.59 / sqft
  3. Previous Price: $6,800,000
  4. Last Price Change: 04/13/26
  5. Days On Market: 201
  6. Bedrooms: 5
  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 Elementary
  6. Middle School: Laurel Nokomis Middle
  7. High School: Venice Senior High
  8. Provided by: DOUGLAS ELLIMAN
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Gulf Front, private beach. This sun drenched Florida villa captures the character of a Mexican hacienda with the ease of tropical coastal living. Smooth stucco exteriors, clay tile roofing, and vibra
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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: 16
  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
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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
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730 Sarabay Road
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Details for 730 Sarabay Road, OSPREY, FL 34229
Single Family
  1. Price: $4,995,000.00
  2. Price sqft: $612.43 / sqft
  3. Previous Price: $5,495,000
  4. Last Price Change: 04/18/26
  5. Days On Market: 155
  6. Bedrooms: 4
  7. Baths: 6
  8. Garage / Parking Spaces: 7
  9. Bldg sqft: 8156
  10. Acreage: 2.00 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: Yes
  14. Wateraccess: Yes
  15. Waterfront Type: Bay/Harbor,Intracoastal Waterway
  16. 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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One or more photo(s) has been virtually staged. PREMIER HIGH ELEVATION BAYFRONT ESTATE ON 2 PRIVATE ACRES 4 Bedrooms | 5.5 Bathrooms | 6,308 Sq. Ft. | 730 Sarabay Road is a rare opportunity to own two
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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: 58
  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 Elementary
  6. Middle School: Laurel Nokomis Middle
  7. High School: Venice Senior High
  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: $3,790,000.00
  2. Price sqft: $325.32 / sqft
  3. Previous Price: $3,890,000
  4. Last Price Change: 04/12/26
  5. Days On Market: 186
  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 Elementary
  6. Middle School: Laurel Nokomis 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. 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: 132
  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 School
  6. Middle School: Pine View School
  7. High School: Pine View School
  8. Provided by: COLDWELL BANKER REALTY
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One or more photo(s) has been virtually staged. Exceptional Waterfront Estate on North Casey Key. Set along the coveted shores of North Casey Key, this exceptional waterfront residence presents a rare
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14401 Masthead Drive
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Details for 14401 Masthead Drive, OSPREY, FL 34229
Single Family
  1. Price: $3,250,000.00
  2. Price sqft: $815.76 / sqft
  3. Days On Market: 49
  4. Bedrooms: 3
  5. Baths: 4
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3984
  8. Acreage: 0.44 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Bay/Harbor
  14. Year Built: 2017
MLS#: A4684834
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Bayside
  5. Elementary School: Laurel Nokomis Elementary
  6. Middle School: Sarasota Middle
  7. High School: Venice Senior High
  8. Provided by: MICHAEL SAUNDERS & COMPANY
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Unobstructed bayfront views and refined coastal luxury define this exceptional waterfront residence in the gated Bayside community. Custom built in 2017 by Rob Allegra and ideally positioned on a priv
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662 Fernwalk Lane
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Details for 662 Fernwalk Lane, OSPREY, FL 34229
Single Family
  1. Price: $2,850,000.00
  2. Price sqft: $452.38 / sqft
  3. Days On Market: 84
  4. Bedrooms: 4
  5. Baths: 4
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 6300
  8. Acreage: 0.44 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 1989
MLS#: A4679996
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Oaks
  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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**exceptional, fully renovated, country club estate home offering tranquil lake and garden views** ideally positioned on a serene interior cul de sac lot in flood zone x (no flood insurance required).
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141 Casey Key Road
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Details for 141 Casey Key Road, OSPREY, FL 34229
Land
  1. Price: $2,850,000.00
  2. Previous Price: $3,200,000
  3. Last Price Change: 04/08/26
  4. Days On Market: 175
  5. Acreage: 0.39 acres
  6. Pool: No
  7. Waterfront: Yes
  8. Wateraccess: Yes
  9. Waterfront Type: Gulf/Ocean
  10. Year Built: Not Available
MLS#: A4669513
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Elementary School: Laurel Nokomis Elementary
  5. Middle School: Laurel Nokomis Middle
  6. High School: Venice Senior High
  7. Provided by: WHITE SANDS REALTY GROUP FL
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Gulf front vacant lot on Casey Key in Osprey. Buildable lot with County guidance. 107' Gulf frontage, cleared site ready for new construction. For buyers seeking to build a custom waterfront home,
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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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