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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: 145
  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
  6. Middle School: Laurel Nokomis
  7. High School: Venice Senior
  8. Provided by: PREMIER SOTHEBYS INTL REALTY
  9. mfrmls
  10. DMCA Notice
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: 385
  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
  5. mfrmls
  6. DMCA Notice
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: 27
  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
  6. Provided by: MICHAEL SAUNDERS & COMPANY
  7. mfrmls
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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: 141
  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
  6. Middle School: Laurel Nokomis
  7. High School: Venice Senior
  8. Provided by: PREMIER SOTHEBYS INTL REALTY
  9. mfrmls
  10. DMCA Notice
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. Days On Market: 270
  4. Bedrooms: 4
  5. Baths: 6
  6. Garage / Parking Spaces: 4
  7. Bldg sqft: 11650
  8. Acreage: 0.78 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. 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
  6. Middle School: Laurel Nokomis
  7. High School: Venice Senior
  8. Provided by: GENEROUS PROPERTY
  9. mfrmls
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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: 87
  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: BayAccess
  13. Year Built: 1995
MLS#: A4650216
  1. County: SARASOTA
  2. City: Osprey
  3. Zipcode: 34229
  4. Subdivision: Palmer
  5. Elementary School: Pine View
  6. Middle School: Pine View
  7. High School: Pine View
  8. Provided by: COLDWELL BANKER REALTY
  9. Provided through
  10. DMCA Notice
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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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: 86
  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
  6. Middle School: Pine View
  7. High School: Pine View
  8. Provided by: COLDWELL BANKER REALTY
  9. mfrmls
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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: $3,705,000.00
  2. Price sqft: $334.51 / sqft
  3. Previous Price: $3,900,000
  4. Last Price Change: 06/06/25
  5. Days On Market: 88
  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
  9. Provided through
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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: $3,705,000.00
  2. Price sqft: $334.51 / sqft
  3. Previous Price: $3,900,000
  4. Last Price Change: 07/07/25
  5. Days On Market: 87
  6. Bedrooms: 4
  7. Baths: 6
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 11076
  10. Acreage: 0.60 acres
  11. Pool: Yes
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: Bay/Harbor,Intracoastal Waterway
  15. 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
  9. mfrmls
  10. DMCA Notice
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: 41
  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
  6. mfrmls
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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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