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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: 252
  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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121 Casey Key Road
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Details for 121 Casey Key Road, OSPREY, FL 34229
Single Family
  1. Price: $7,100,000.00
  2. Price sqft: $1,028.09 / sqft
  3. Days On Market: 42
  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: 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 Elementary
  6. Middle School: Laurel Nokomis Middle
  7. High School: Venice Senior High
  8. Provided by: DOUGLAS ELLIMAN
  9. mfrmls
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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
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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: $7,100,000.00
  2. Price sqft: $1,028.09 / sqft
  3. Days On Market: 42
  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: BeachAccess,GulfAccess,OceanAccess
  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
  9. Provided through
  10. DMCA Notice
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
Listing Details and 76 Additional Pictures
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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: $5,990,000.00
  2. Price sqft: $558.66 / sqft
  3. Previous Price: $6,490,000
  4. Last Price Change: 10/07/25
  5. Days On Market: 99
  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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A striking coastal retreat on over half an acre along Little Sarasota Bay, this timeless residence blends architectural elegance with waterfront living. Offering private access to the Intracoastal wit
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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: $5,990,000.00
  2. Price sqft: $558.66 / sqft
  3. Previous Price: $6,490,000
  4. Last Price Change: 09/19/25
  5. Days On Market: 99
  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,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
A striking coastal retreat on over half an acre along Little Sarasota Bay, this timeless residence blends architectural elegance with waterfront living. Offering private access to the Intracoastal wit
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622 Bayshore Drive
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Details for 622 Bayshore Drive, OSPREY, FL 34229
Single Family
  1. Price: $5,700,000.00
  2. Price sqft: $977.37 / sqft
  3. Previous Price: $6,750,000
  4. Last Price Change: 09/23/25
  5. Days On Market: 134
  6. Bedrooms: 6
  7. Baths: 5
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 5832
  10. Acreage: 0.78 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: Yes
  14. Wateraccess: Yes
  15. Waterfront Type: Bay/Harbor
  16. 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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ELEVATED ABOVE FLOOD LEVEL WITH EXCEPTIONALLY LOW INSURANCE PREMIUMS ! Welcome to 622 Bayshore Drive where coastal luxury meets modern sophistication on one of the most sought after stretches of L
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614 Bayshore Drive
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New Construction
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Details for 614 Bayshore Drive, OSPREY, FL 34229
Single Family
  1. Price: $5,500,000.00
  2. Price sqft: $866.55 / sqft
  3. Days On Market: 91
  4. Bedrooms: 3
  5. Baths: 5
  6. Garage / Parking Spaces: 5
  7. Bldg sqft: 6347
  8. Acreage: 0.52 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Bay/Harbor
  14. Year Built: 2024
MLS#: A4662210
  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: DOUGLAS ELLIMAN
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New Seawall / Waterside deck, New Automated Gate, Lanai Automated Screens Commanding over half an acre with 116 feet of pristine frontage on Little Sarasota Bay, this brand new custom estate captu
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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: $5,000,000.00
  2. Price sqft: $730.89 / sqft
  3. Days On Market: 58
  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 Elementary
  6. Middle School: Sarasota Middle
  7. High School: Venice Senior High
  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
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691 Eagle Watch Lane
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Details for 691 Eagle Watch Lane, OSPREY, FL 34229
Single Family
  1. Price: $3,995,000.00
  2. Price sqft: $421.33 / sqft
  3. Days On Market: 9
  4. Bedrooms: 4
  5. Baths: 7
  6. Garage / Parking Spaces: 4
  7. Bldg sqft: 9482
  8. Acreage: 0.78 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 1993
MLS#: A4668477
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Oaks 2 Ph 2
  5. Elementary School: Laurel Nokomis
  6. Middle School: Sarasota
  7. High School: Venice Senior
  8. Provided by: SARASOTA TRUST REALTY COMPANY
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Nestled within the exclusive gated community of the Oaks Club in Osprey, Florida. This singular estate represents a masterful confluence of architectural refinement and modern luxury, encompassing nea
Listing Details and 99 Additional Pictures
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691 Eagle Watch Lane
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Details for 691 Eagle Watch Lane, Osprey, FL 34229
Single Family
  1. Price: $3,995,000.00
  2. Price sqft: $421.33 / sqft
  3. Days On Market: 10
  4. Bedrooms: 4
  5. Baths: 7
  6. Garage / Parking Spaces: 4
  7. Bldg sqft: 9482
  8. Acreage: 0.78 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 1993
MLS#: A4668477
  1. County: SARASOTA
  2. City: Osprey
  3. Zipcode: 34229
  4. Subdivision: Oaks 2 Ph 2
  5. Elementary School: Laurel Nokomis
  6. Middle School: Sarasota
  7. High School: Venice Senior
  8. Provided by: SARASOTA TRUST REALTY COMPANY
  9. Provided through
  10. DMCA Notice
Nestled within the exclusive gated community of the Oaks Club in Osprey, Florida. This singular estate represents a masterful confluence of architectural refinement and modern luxury, encompassing nea
Listing Details and 99 Additional Pictures
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