New95$2,150,000
4 bd · 5 ba · 3,939 sqft
642 Trenton Way, Osprey, FL
Steve Abbe · COLDWELL BANKER REALTY
Homes for Sale in Osprey, FL
Hide MapHomes for Sale in Osprey, FL
24 of 97 Listings
New95$2,150,000
4 bd · 5 ba · 3,939 sqft
642 Trenton Way, Osprey, FL
Steve Abbe · COLDWELL BANKER REALTY
70$739,000
3 bd · 2 ba · 2,326 sqft
335 Park Trace Blvd, Osprey, FL
Kim Klee · COLDWELL BANKER REALTY
54$1,047,000
3 bd · 3 ba · 2,134 sqft
102 Windward Dr, Osprey, FL
Adam Leinwand · FUTURE HOME REALTY INC
7$149,900
— bd · 0 ba · — sqft
570 Blackburn Point Rd #Siesta 25, Osprey, FL
David Babel · BRIGHT REALTY
Open house Sun, Oct 18 · 12:00 PM56$1,049,000
4 bd · 3 ba · 2,775 sqft
366 S Creek Ct, Osprey, FL
EJ Stukenborg · KELLER WILLIAMS ON THE WATER S
100$1,025,000
3 bd · 3 ba · 2,778 sqft
401 N Point Rd #404, Osprey, FL
Steve Abbe · COLDWELL BANKER REALTY
36$465,000
2 bd · 2 ba · 1,404 sqft
120 Villa Dr #120, Osprey, FL
Antonio Lopez · MANGROVE REALTY ASSOCIATES
95$1,445,000
3 bd · 4 ba · 3,872 sqft
422 Blue Garden Ln, Osprey, FL
Steve Abbe · COLDWELL BANKER REALTY
31$175,000
2 bd · 2 ba · 960 sqft
145 Edgewood Dr, Osprey, FL
Mark Lyda · GENEROUS PROPERTY
34$159,900
1 bd · 1 ba · 586 sqft
717 Pine Run Dr. #717, Osprey, FL
Pat Williams · PAT WILLIAMS REALTY, LLC
56$1,200,000
3 bd · 3 ba · 2,203 sqft
401 N Point Rd #703, Osprey, FL
Mark Lyda · GENEROUS PROPERTY
Open house Sun, Oct 18 · 1:00 PM88$625,000
3 bd · 2 ba · 1,937 sqft
250 Hidden Bay Dr #302, Osprey, FL
Pan Steele · COLDWELL BANKER REALTY
96$4,590,000
5 bd · 5 ba · 5,279 sqft
275 Lookout Point Dr, Osprey, FL
Natalie Gutwein · MICHAEL SAUNDERS & COMPANY
100$1,399,000
3 bd · 3 ba · 2,594 sqft
385 North Point Rd #701, Osprey, FL
Judy Wright, PA · MICHAEL SAUNDERS & COMPANY
100$695,000
3 bd · 3 ba · 2,594 sqft
385 N Point Rd #401, Osprey, FL
Steve Abbe · COLDWELL BANKER REALTY
100$3,700,000
4 bd · 4 ba · 4,314 sqft
650 Oaks Creek Ct, Osprey, FL
Steve Abbe · COLDWELL BANKER REALTY
Open house Sun, Oct 18 · 1:00 PM35$449,000
3 bd · 2 ba · 1,883 sqft
7303 Jessie Harbor Dr #7303, Osprey, FL
Mairead Smialek · COLDWELL BANKER REALTY
50$629,400
3 bd · 3 ba · 3,147 sqft
3603 N Point Rd #202, Osprey, FL
Mark Lyda · GENEROUS PROPERTY
Open house Sun, Oct 18 · 1:00 AM55$540,000
3 bd · 2 ba · 2,248 sqft
1346 Thornapple Dr, Osprey, FL
Debra Robinson · RE/MAX ALLIANCE GROUP
69$679,000
2 bd · 3 ba · 1,890 sqft
33 Bishops Court Rd #118, Osprey, FL
Mark Lyda · GENEROUS PROPERTY
59$1,399,000
3 bd · 3 ba · 2,695 sqft
256 Sugar Mill, Osprey, FL
Ivan Bovkun · KIMBERLITE WEST REALTY LLC
59$165,000
2 bd · 2 ba · 924 sqft
23 Siesta Cir W, Osprey, FL
Karen Geiger · COLDWELL BANKER SARASOTA CENT.
100$3,700,000
5 bd · 5 ba · 6,234 sqft
324 Osprey Point Dr, Osprey, FL
Steve Abbe · COLDWELL BANKER REALTY
Price Reduced100$1,270,000
3 bd · 2 ba · 2,850 sqft
17 Bayhead Ln, Osprey, FL
Steve Abbe · COLDWELL BANKER REALTY
Stellar MLSSource: HJN community data
September 2026 · This period is still settling
Selling at 96.2% of asking price
Buyers here are paying below asking. MLS · 16 sales · as of Sep 30, 2026