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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: 150
  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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505 Luminary Boulevard
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Details for 505 Luminary Boulevard, OSPREY, FL 34229
Commercial
  1. Price: $7,499,000.00
  2. Price sqft: $1,874.75 / sqft
  3. Days On Market: 390
  4. Bldg sqft: 4000
  5. Acreage: 10.01 acres
  6. Pool: No
  7. Waterfront: No
  8. Year Built: 2015
MLS#: A4616676
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Provided by: AMERICAN PROPERTY GROUP
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American Property Group of Sarasota, Inc. presents 505 Luminary Blvd, Osprey, Sarasota Property Type: Commercial Land with Existing Office Building Property Size: 10 Acres Discover this exceptional
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622 Bayshore Drive
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Details for 622 Bayshore Drive, OSPREY, FL 34229
Single Family
  1. Price: $6,750,000.00
  2. Price sqft: $1,018.56 / sqft
  3. Days On Market: 32
  4. Bedrooms: 6
  5. Baths: 5
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 6627
  8. Acreage: 0.78 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Bay/Harbor
  14. Year Built: 2022
MLS#: A4657777
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Bay Acres Resub
  5. High School: Pine View School
  6. Provided by: MICHAEL SAUNDERS & COMPANY
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Welcome to 622 Bayshore Drive where coastal luxury meets modern sophistication on one of the most sought after stretches of Little Sarasota Bay. Tucked away on a rare and expansive .78 acre gated es
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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: 146
  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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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: 07/10/25
  5. Days On Market: 275
  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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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: 91
  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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112 Osprey Point Drive
Foreclosure
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Details for 112 Osprey Point Drive, OSPREY, FL 34229
Single Family
  1. Price: $3,500,000.00
  2. Price sqft: $316.00 / sqft
  3. Days On Market: 92
  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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112 Osprey Point Drive
Foreclosure
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Details for 112 Osprey Point Drive, Osprey, FL 34229
Single Family
  1. Price: $3,500,000.00
  2. Price sqft: $316.00 / sqft
  3. Previous Price: $3,705,000
  4. Last Price Change: 07/31/25
  5. Days On Market: 92
  6. Bedrooms: 4
  7. Baths: 6
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 11076
  10. Acreage: 0.60 acres
  11. Pool: Yes
  12. Community Pool: Yes
  13. Waterfront: Yes
  14. Wateraccess: Yes
  15. Waterfront Type: BayAccess,IntracoastalAccess
  16. Year Built: 1989
MLS#: O6305818
  1. County: SARASOTA
  2. City: Osprey
  3. Zipcode: 34229
  4. Subdivision: Oaks
  5. Elementary School: Laurel Nokomis
  6. Middle School: Venice Area
  7. High School: Venice Senior
  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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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: 46
  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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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: 07/29/25
  5. Days On Market: 187
  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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