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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: 106
  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
  9. mfrmls
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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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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: 102
  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
  9. mfrmls
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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: 03/31/25
  5. Days On Market: 638
  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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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: 06/14/25
  5. Days On Market: 230
  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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112 Osprey Point Drive
Foreclosure
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Details for 112 Osprey Point Drive, OSPREY, FL 34229
Single Family
  1. Price: $3,900,000.00
  2. Price sqft: $352.11 / sqft
  3. Days On Market: 48
  4. Bedrooms: 4
  5. Baths: 6
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 11076
  8. Acreage: 0.60 acres
  9. Pool: Yes
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: Bay/Harbor,Intracoastal Waterway
  13. Year Built: 1989
MLS#: O6305818
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Oaks
  5. Elementary School: Laurel Nokomis Elementary
  6. Middle School: Venice Area Middle
  7. High School: Venice Senior High
  8. Provided by: KARA MONEY LLC
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Premier Waterfront Opportunity in The Oaks Bayside This grand estate home, perfectly positioned on a rarely available direct waterfront lot in the exclusive, gated Oaks Bayside community, offers swee
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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: 47
  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#: A4650216
  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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EXCEPTIONAL WATERFRONT RESIDENCE on the exclusive island of North Casey Key is a rare opportunity to own a piece of coastal Florida. Nestled in the sought after Palmer neighborhood, this home has been
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550 Dove Pointe
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Details for 550 Dove Pointe, OSPREY, FL 34229
Single Family
  1. Price: $3,300,000.00
  2. Price sqft: $357.76 / sqft
  3. Days On Market: 2
  4. Bedrooms: 4
  5. Baths: 6
  6. Garage / Parking Spaces: 4
  7. Bldg sqft: 9224
  8. Acreage: 0.83 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 2006
MLS#: A4656464
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Oaks
  5. Provided by: MICHAEL SAUNDERS & COMPANY
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Sited at the end of a quiet cul de sac behind the gates of the prestigious Oaks Clubside in Osprey, Florida, this stately traditional custom estate offers refined living in one of Sarasota Countys mos
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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: $3,250,000.00
  2. Price sqft: $924.61 / sqft
  3. Previous Price: $3,375,000
  4. Last Price Change: 06/16/25
  5. Days On Market: 265
  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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Home run deal you can't afford to miss! Casey key gulf front move in ready for unbelievable price! Reduced 900k! Iconic gulf front mid century modern gated residence on casey key embodies the true ess
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662 Fernwalk Lane
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Details for 662 Fernwalk Lane, OSPREY, FL 34229
Single Family
  1. Price: $2,995,000.00
  2. Price sqft: $475.40 / sqft
  3. Previous Price: $3,150,000
  4. Last Price Change: 04/08/25
  5. Days On Market: 142
  6. Bedrooms: 4
  7. Baths: 4
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 6300
  10. Acreage: 0.44 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: No
  14. Year Built: 1989
MLS#: A4635707
  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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**fantastic, fully renovated estate with lake / garden view is situated on a serene, interior, cul de sac lot with no flood concern (zone x) behind the secure gates of the highly sought after bayside
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236 Saint James Park
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Details for 236 Saint James Park, OSPREY, FL 34229
Single Family
  1. Price: $2,900,000.00
  2. Price sqft: $302.43 / sqft
  3. Days On Market: 86
  4. Bedrooms: 6
  5. Baths: 7
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 9589
  8. Acreage: 0.56 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 1986
MLS#: A4644125
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Oaks 2 Ph 1
  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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Tucked away in a quiet cul de sac on a double lot beneath majestic oaks, this almost 5,000 sq ft, timeless 2 story home blends sophistication with modern comfort. Situated on the first hole of Heron G
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