New100$640,000
3 bd · 2 ba · 1,736 sqft
14041 Bellagio Way #315, Osprey, FL
Dawn Bear · WILLIAM RAVEIS - FLORIDA LLC
Waterfront Homes in Osprey, FL
Hide MapWaterfront Homes in Osprey, FL
24 of 34 Listings
New100$640,000
3 bd · 2 ba · 1,736 sqft
14041 Bellagio Way #315, Osprey, FL
Dawn Bear · WILLIAM RAVEIS - FLORIDA LLC
70$739,000
3 bd · 2 ba · 2,326 sqft
335 Park Trace Blvd, Osprey, FL
Kim Klee · COLDWELL BANKER REALTY
7$149,900
— bd · 0 ba · — sqft
570 Blackburn Point Rd #Siesta 25, Osprey, FL
David Babel · BRIGHT REALTY
36$465,000
2 bd · 2 ba · 1,404 sqft
120 Villa Dr #120, Osprey, FL
Antonio Lopez · MANGROVE REALTY ASSOCIATES
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
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
100$3,700,000
5 bd · 5 ba · 6,234 sqft
324 Osprey Point Dr, Osprey, FL
Steve Abbe · COLDWELL BANKER REALTY
Open house Sun, Oct 18 · 2:00 PM46$749,900
3 bd · 2 ba · 2,174 sqft
1328 Thornapple Dr, Osprey, FL
Heather Claridge · RIVER HILLS PROPERTIES, LLC B
Price Reduced43$565,000
3 bd · 2 ba · 1,705 sqft
2046 Cordes St, Osprey, FL
Sue Mondello · MICHAEL SAUNDERS & COMPANY
71$9,750,000
5 bd · 8 ba · 8,050 sqft
1216 N Casey Key Rd, Osprey, FL
Valerie Dall'Acqua · PREMIER SOTHEBY'S INTERNATIONAL REALTY
62$599,000
2 bd · 2 ba · 2,143 sqft
5100 Jessie Harbor Dr #404, Osprey, FL
Stuart Lawrence · MICHAEL SAUNDERS & COMPANY
58$775,000
3 bd · 3 ba · 1,950 sqft
260 Hidden Bay Dr #402, Osprey, FL
Thomas Netzel · PREMIER SOTHEBY'S INTERNATIONAL REALTY
4$99,500
— bd · 0 ba · — sqft
570 Blackburn Point Rd #36, Osprey, FL
David Babel · BRIGHT REALTY
54$425,000
2 bd · 2 ba · 1,574 sqft
780 Sarabay Rd #16, Osprey, FL
Mark Segreto · RMS ELITE PROPERTIES
43$395,000
2 bd · 2 ba · 1,255 sqft
7204 Jessie Harbor Dr #7204, Osprey, FL
Mark Lyda · GENEROUS PROPERTY
65$4,790,000
4 bd · 6 ba · 5,087 sqft
101 Osprey Point Dr, Osprey, FL
Joel Schemmel · DOUGLAS ELLIMAN
71$275,000
1 bd · 1 ba · 623 sqft
51 Macewen Dr #12, Osprey, FL
Steve Abbe · COLDWELL BANKER REALTY
47$3,295,000
3 bd · 5 ba · 2,572 sqft
135 Tina Island Dr, Osprey, FL
Mark Lyda · GENEROUS PROPERTY
Price Reduced83$798,000
3 bd · 4 ba · 3,771 sqft
6100 Jessie Harbor Dr #202, Osprey, FL
Angelic Tassos · CORCORAN DWELLINGS REALTY
Price Reduced70$999,900
3 bd · 3 ba · 2,187 sqft
14021 Bellagio Way #404, Osprey, FL
Megan E. George, PA · PREMIER SOTHEBYS INTL REALTY
Price Reduced44$235,000
1 bd · 1 ba · 595 sqft
51 Macewen Dr #5, Osprey, FL
Sabine Spycher · 342 REAL ESTATE
Waterfront Homes in Osprey, FL: 34 active listings as of .
| Property type | Listings | Share |
|---|---|---|
| Condominium | 15 | 44.1% |
| Single Family Residence | 13 | 38.2% |
























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