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    1. Zipcode = 34229
    2. Listing Status = Active
    Details for 1216 Casey Key Road, OSPREY, FL 34229
    Single Family
    1. Price: $10,750,000.00
    2. Price sqft: $692.57 / sqft
    3. Previous Price: $11,750,000
    4. Last Price Change: 01/10/26
    5. Days On Market: 427
    6. Bedrooms: 5
    7. Baths: 8
    8. Garage / Parking Spaces: 4
    9. Bldg sqft: 15522
    10. Acreage: 1.10 acres
    11. Pool: Yes
    12. Spa/HotTub: Yes
    13. Waterfront: Yes
    14. Wateraccess: Yes
    15. Waterfront Type: Bay/Harbor,Beach Front,Gulf/Ocean,Gulf/Ocean to Bay,Intracoastal Waterway
    16. 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
    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: 667
    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
    Property Type: Commercial Land with Existing Office Building Property Size: 10 Acres Discover this exceptional opportunity with over 900 feet of frontage on Tamiami Trail/US41 in Osprey, FL! This
    Details for 121 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: 216
    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
    9. mfrmls
    10. DMCA Notice
    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 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: 31
    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
    9. mfrmls
    10. DMCA Notice
    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 730 Sarabay Road, OSPREY, FL 34229
    Single Family
    1. Price: $4,995,000.00
    2. Price sqft: $612.43 / sqft
    3. Previous Price: $5,495,000
    4. Last Price Change: 03/28/26
    5. Days On Market: 170
    6. Bedrooms: 4
    7. Baths: 6
    8. Garage / Parking Spaces: 7
    9. Bldg sqft: 8156
    10. Acreage: 2.00 acres
    11. Pool: Yes
    12. Spa/HotTub: Yes
    13. Waterfront: Yes
    14. Wateraccess: Yes
    15. Waterfront Type: Bay/Harbor,Intracoastal Waterway
    16. Year Built: 2011
    MLS#: A4672618
    1. County: SARASOTA
    2. City: OSPREY
    3. Zipcode: 34229
    4. Subdivision: Sarabay Acres
    5. Provided by: ROBERT SLACK LLC
    6. mfrmls
    7. DMCA Notice
    One or more photo(s) has been virtually staged. PREMIER HIGH ELEVATION BAYFRONT ESTATE ON 2 PRIVATE ACRES 4 Bedrooms | 5.5 Bathrooms | 6,308 Sq. Ft. | 730 Sarabay Road is a rare opportunity to own two
    Details for 324 Bayshore Drive, OSPREY, FL 34229
    Single Family
    1. Price: $3,995,000.00
    2. Price sqft: $501.19 / sqft
    3. Previous Price: $4,250,000
    4. Last Price Change: 04/30/26
    5. Days On Market: 73
    6. Bedrooms: 4
    7. Baths: 5
    8. Garage / Parking Spaces: 2
    9. Bldg sqft: 7971
    10. Acreage: 0.47 acres
    11. Pool: Yes
    12. Spa/HotTub: Yes
    13. Waterfront: Yes
    14. Wateraccess: Yes
    15. Waterfront Type: Bay/Harbor
    16. Year Built: 2000
    MLS#: A4683138
    1. County: SARASOTA
    2. City: OSPREY
    3. Zipcode: 34229
    4. Subdivision: Bay Acres Resub
    5. Elementary School: Laurel Nokomis
    6. Middle School: Laurel Nokomis
    7. High School: Venice Senior
    8. Provided by: MICHAEL SAUNDERS & COMPANY
    9. mfrmls
    10. DMCA Notice
    Big bay views surround you from this exquisitely updated waterfront estate. Welcome to 324 Bayshore Drive, a property of nearly half an acre set on a large, open stretch of the bay with easy access to
    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: 147
    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#: A4674771
    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
    10. DMCA Notice
    One or more photo(s) has been virtually staged. Exceptional Waterfront Estate on North Casey Key. Set along the coveted shores of North Casey Key, this exceptional waterfront residence presents a rare
    Details for 854 Macewen Drive, OSPREY, FL 34229
    Single Family
    1. Price: $3,690,000.00
    2. Price sqft: $316.74 / sqft
    3. Previous Price: $3,790,000
    4. Last Price Change: 05/01/26
    5. Days On Market: 201
    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#: A4668918
    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: COLDWELL BANKER REALTY
    9. mfrmls
    10. DMCA Notice
    One or more photo(s) has been virtually staged. Set on a private cul de sac within The Oaks, this revitalized estate captures the essence of elegant Florida living. From the moment you enter, the home
    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: 3
    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: 1965
    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
    9. mfrmls
    10. DMCA Notice
    **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: $3,150,000.00
    2. Price sqft: $790.66 / sqft
    3. Previous Price: $3,250,000
    4. Last Price Change: 05/01/26
    5. Days On Market: 64
    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
    9. mfrmls
    10. DMCA Notice
    Unobstructed bayfront views and refined coastal luxury define this exceptional waterfront residence in the gated Bayside community. Custom built in 2017 by Rob Allegra and ideally positioned on a priv
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