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  1. Zipcode = 34229
  2. Listing Status = Active
Details for 1216 N Casey Key Road, OSPREY, FL 34229
Single Family
  1. Price: $9,750,000.00
  2. Price sqft: $628.14 / sqft
  3. Days On Market: 18
  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#: A4704643
  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 SOTHEBY'S INTERNATIONAL REALTY
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At the northernmost point of Casey Key, where the Gulf meets the tranquil waters of Little Sarasota and Blackburn Bay, an extraordinary private estate unfolds between two worlds of water. Beyond a sec
Details for 121 N 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: 03/10/26
  5. Days On Market: 350
  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
  6. Middle School: Laurel Nokomis
  7. High School: Venice Senior
  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
Details for 112 Osprey Point Drive, OSPREY, FL 34229
Single Family
  1. Price: $6,449,000.00
  2. Price sqft: $582.25 / sqft
  3. Days On Market: 16
  4. Bedrooms: 6
  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
  13. Year Built: 1989
MLS#: A4702047
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Oaks
  5. Elementary School: Laurel Nokomis
  6. Middle School: Sarasota
  7. High School: Venice Senior
  8. Provided by: DOUGLAS ELLIMAN
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Under contract accepting backup offers. A rare combination of timeless grandeur and effortless waterfront living, this bayfront estate in The Oaks Bayside commands approximately 150 feet of Bay fronta
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: 165
  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
Details for 101 Osprey Point Drive, OSPREY, FL 34229
Single Family
  1. Price: $4,790,000.00
  2. Price sqft: $700.19 / sqft
  3. Days On Market: 115
  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#: A4694716
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Oaks
  5. Elementary School: Laurel Nokomis
  6. Middle School: Sarasota
  7. High School: Venice Senior
  8. Provided by: DOUGLAS ELLIMAN
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Lakefront living and elevated architecture come together at 101 Osprey Point Drive, a Bo MacEwen designed estate privately positioned on nearly an acre within the gates of Sarasotas prestigious Oaks B
Details for 135 Tina Island Drive, OSPREY, FL 34229
Single Family
  1. Price: $3,295,000.00
  2. Price sqft: $526.86 / sqft
  3. Days On Market: 137
  4. Bedrooms: 3
  5. Baths: 5
  6. Garage / Parking Spaces: 4
  7. Bldg sqft: 6254
  8. Acreage: 0.37 acres
  9. Pool: No
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: Canal Front
  13. Year Built: 2011
MLS#: A4692366
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Sorrento Shores
  5. Elementary School: Laurel Nokomis
  6. Middle School: Laurel Nokomis
  7. High School: Venice Senior
  8. Provided by: GENEROUS PROPERTY
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**EXCEPTIONAL WATERFRONT RESIDENCE with 210 ft CANAL FRONTAGE** in desirable Sorrento Shores, offering Deep Water access with No Bridges to the Bay/Gulf. Privately situated on a quiet cul de sac, the
Details for 14401 Masthead Drive, OSPREY, FL 34229
Single Family
  1. Price: $2,850,000.00
  2. Price sqft: $715.36 / sqft
  3. Previous Price: $2,995,000
  4. Last Price Change: 08/11/26
  5. Days On Market: 197
  6. Bedrooms: 3
  7. Baths: 4
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 3984
  10. Acreage: 0.44 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: Yes
  14. Wateraccess: Yes
  15. Waterfront Type: Bay/Harbor
  16. Year Built: 2017
MLS#: A4684834
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Bayside
  5. Elementary School: Laurel Nokomis
  6. Middle School: Sarasota
  7. High School: Venice Senior
  8. Provided by: MICHAEL SAUNDERS & COMPANY
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Under contract accepting backup offers. Unobstructed bayfront views and refined coastal luxury define this exceptional waterfront residence in the gated Bayside community. Custom built in 2017 by Rob
Details for 2301 S Tamiami Trail, OSPREY, FL 34229
Land
  1. Price: $2,850,000.00
  2. Days On Market: 42
  3. Acreage: 4.18 acres
  4. Pool: No
  5. Waterfront: No
  6. Year Built: Not Available
MLS#: A4702316
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Springhill Park
  5. Provided by: SARABAY REAL ESTATE INC
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This listing is for 4.2 +/ acres consisting of two parcels that are rectangular in shape, cleared and level. The parcels have 700 +/ linear feet on US 41 (Tamiami Trail). The daily traffic counts th
Details for 236 Saint James Park, OSPREY, FL 34229
Single Family
  1. Price: $2,700,000.00
  2. Price sqft: $281.57 / sqft
  3. Previous Price: $2,900,000
  4. Last Price Change: 11/25/25
  5. Days On Market: 541
  6. Bedrooms: 6
  7. Baths: 7
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 9589
  10. Acreage: 0.56 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: No
  14. 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
  6. Middle School: Laurel Nokomis
  7. High School: Venice Senior
  8. Provided by: MICHAEL SAUNDERS & COMPANY
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Multigenerational living behind the gates of The Oaks Golf & Country Club. Set on a rare double lot at the end of a quiet cul de sac, this exceptional home is perfectly positioned on the 1st hole of t
Details for 49 Osprey Point Drive, OSPREY, FL 34229
Single Family
  1. Price: $2,399,000.00
  2. Price sqft: $458.96 / sqft
  3. Previous Price: $2,500,000
  4. Last Price Change: 05/04/26
  5. Days On Market: 309
  6. Bedrooms: 4
  7. Baths: 4
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 5227
  10. Acreage: 0.40 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: Yes
  14. Wateraccess: Yes
  15. Waterfront Type: Lake Front
  16. Year Built: 1989
MLS#: A4671762
  1. County: SARASOTA
  2. City: OSPREY
  3. Zipcode: 34229
  4. Subdivision: Oaks
  5. Elementary School: Laurel Nokomis
  6. Middle School: Sarasota
  7. High School: Venice Senior
  8. Provided by: MICHAEL SAUNDERS & COMPANY
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Nestled in the prestigious gated enclave of The Oaks Bayside in Sarasota, this Sedona inspired retreat was recently updated from wall to wall creating a like brand new home. The estate seamlessly blen