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  1. Zipcode = 34229
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: 7
  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
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: 64
  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
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: 213
  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: BayAccess,BeachAccess,GulfAccess,IntracoastalAccess,OceanAccess
  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. Provided through
  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
Details for 135 Tina Island Drive, Osprey, FL 34229
Single Family
  1. Price: $3,400,000.00
  2. Price sqft: $1,321.93 / sqft
  3. Previous Price: $3,450,000
  4. Last Price Change: 09/22/25
  5. Days On Market: 23
  6. Bedrooms: 3
  7. Baths: 5
  8. Garage / Parking Spaces: 4
  9. Bldg sqft: 2572
  10. Acreage: 0.37 acres
  11. Pool: No
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: CanalFront,GulfAccess
  15. Year Built: 1965
MLS#: A4665474
  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: FLATFEE.COM
  9. Provided through
  10. DMCA Notice
Retreat to paradise in this stunning waterfront home, built new in 2011, in highly sought after Sorrento Shores, Osprey. Perfectly situated on 210 feet of wide canal frontage, this residence offers de
Details for 600 Eagle Watch Lane, Osprey, FL 34229
Single Family
  1. Price: $2,195,000.00
  2. Price sqft: $425.64 / sqft
  3. Previous Price: $1,990,000
  4. Last Price Change: 09/10/25
  5. Days On Market: 186
  6. Bedrooms: 3
  7. Baths: 3
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 5157
  10. Acreage: 0.71 acres
  11. Pool: Yes
  12. Community Pool: Yes
  13. Waterfront: No
  14. Year Built: 1992
MLS#: A4647789
  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: COLDWELL BANKER REALTY
  9. Provided through
  10. DMCA Notice
Located on one of the most desirable streets in The Oaks Clubside, this completely renovated pool home sits on a generous 0.71 acre lot with wide views of the third hole of the Heron Golf Course. Near
Details for 85 Sugar Mill Drive, Osprey, FL 34229
Single Family
  1. Price: $2,150,000.00
  2. Price sqft: $420.33 / sqft
  3. Days On Market: 2
  4. Bedrooms: 3
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 5115
  8. Acreage: 0.48 acres
  9. Pool: Yes
  10. Community Pool: Yes
  11. Waterfront: No
  12. Year Built: 1991
MLS#: A4667740
  1. County: SARASOTA
  2. City: Osprey
  3. Zipcode: 34229
  4. Subdivision: Oaks
  5. Elementary School: Laurel Nokomis
  6. Middle School: Laurel Nokomis
  7. High School: Venice Senior
  8. Provided by: GENEROUS PROPERTY
  9. Provided through
  10. DMCA Notice
**stunningly designed and updated architectural estate in the coveted oaks bayside country club neighborhood** on little sarasota bay waters features 3 beds plus den/office, 3 full baths and incred
Details for 500 Shotgun Lane, Osprey, FL 34229
Land
  1. Price: $1,600,000.00
  2. Previous Price: $1,800,000
  3. Last Price Change: 09/04/25
  4. Days On Market: 38
  5. Acreage: 11.68 acres
  6. Pool: No
  7. Waterfront: No
  8. Year Built: Not Available
MLS#: A4661966
  1. County: SARASOTA
  2. City: Osprey
  3. Zipcode: 34229
  4. Subdivision: Acreage & Unrec
  5. Provided by: CHARITY & WEISS INTERNATIONAL LLC
  6. Provided through
  7. DMCA Notice
Truly a rare piece of Florida, a Natural Beauty! More than 11 acres in the heart of it all, west of I 75; Vacant land this size in Ospreys sought after Pine Ranch area is now very rare and seldom com
Details for 156 Bishopscourt Road, Osprey, FL 34229
Single Family
  1. Price: $1,385,000.00
  2. Price sqft: $308.88 / sqft
  3. Days On Market: 32
  4. Bedrooms: 3
  5. Baths: 4
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 4484
  8. Acreage: 0.45 acres
  9. Pool: Yes
  10. Community Pool: Yes
  11. Waterfront: No
  12. Year Built: 1990
MLS#: A4663920
  1. County: SARASOTA
  2. City: Osprey
  3. Zipcode: 34229
  4. Subdivision: Bishopscourt At The Oaks Prese
  5. Elementary School: Gulf Gate
  6. Middle School: Brookside
  7. High School: Riverview
  8. Provided by: COLDWELL BANKER REALTY
  9. Provided through
  10. DMCA Notice
This stunning 3 bedroom, 3.5 bath home, designed by the renowned architect Frank Folsom Smith, stands out with its unique design. The charming Cape Cod style sets the stage for comfortable, graceful l
Details for 1218 Yacht Harbor Drive, Osprey, FL 34229
Single Family
  1. Price: $1,175,000.00
  2. Price sqft: $276.67 / sqft
  3. Previous Price: $1,200,000
  4. Last Price Change: 09/18/25
  5. Days On Market: 38
  6. Bedrooms: 3
  7. Baths: 3
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 4247
  10. Acreage: 0.30 acres
  11. Pool: Yes
  12. Community Pool: Yes
  13. Waterfront: No
  14. Year Built: 1980
MLS#: A4663579
  1. County: SARASOTA
  2. City: Osprey
  3. Zipcode: 34229
  4. Subdivision: Southbay Yacht & Racquet Club
  5. Elementary School: Laurel Nokomis
  6. Middle School: Sarasota
  7. High School: Venice Senior
  8. Provided by: KELLER WILLIAMS ON THE WATER S
  9. Provided through
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New listing alert in the highly sought after community of Southbay Yacht & Racquet Club, where true resort style living awaits. The community offers an impressive array of amenities, including a marin
Details for 701 Eaglenook Way, Osprey, FL 34229
Single Family
  1. Price: $1,150,000.00
  2. Price sqft: $178.18 / sqft
  3. Days On Market: 28
  4. Bedrooms: 4
  5. Baths: 5
  6. Garage / Parking Spaces: 4
  7. Bldg sqft: 6454
  8. Acreage: 2.20 acres
  9. Pool: Yes
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: Pond
  13. Year Built: 1978
MLS#: A4663832
  1. County: SARASOTA
  2. City: Osprey
  3. Zipcode: 34229
  4. Subdivision: Pine Ranch
  5. Elementary School: Laurel Nokomis
  6. Middle School: Laurel Nokomis
  7. High School: Venice Senior
  8. Provided by: COLDWELL BANKER SARASOTA CENT.
  9. Provided through
  10. DMCA Notice
A truly rare opportunity to own a home on over 2 acres in Osprey, FL. Pine Ranch is a charming enclave of 36 properties with low HOA fees and sensible deed restrictions that offers room for your RV, b