96$4,590,000
5 bd · 5 ba · 5,279 sqft
275 Lookout Point Dr, Osprey, FL
Natalie Gutwein · MICHAEL SAUNDERS & COMPANY
Homes with a Pool in Osprey, FL
Hide MapHomes with a Pool in Osprey, FL
9 Listings
96$4,590,000
5 bd · 5 ba · 5,279 sqft
275 Lookout Point Dr, Osprey, FL
Natalie Gutwein · MICHAEL SAUNDERS & COMPANY
100$3,700,000
5 bd · 5 ba · 6,234 sqft
324 Osprey Point Dr, Osprey, FL
Steve Abbe · COLDWELL BANKER REALTY
Open house Sat, Oct 3 · 1:00 PM46$749,900
3 bd · 2 ba · 2,174 sqft
1328 Thornapple Dr, Osprey, FL
Heather Claridge · RIVER HILLS PROPERTIES, LLC B
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
65$4,790,000
4 bd · 6 ba · 5,087 sqft
101 Osprey Point Dr, Osprey, FL
Joel Schemmel · DOUGLAS ELLIMAN
100$5,999,999
4 bd · 5 ba · 5,337 sqft
313 Lookout Point Dr, Osprey, FL
Natalie Gutwein · MICHAEL SAUNDERS & COMPANY
Price Reduced96$2,399,000
4 bd · 4 ba · 3,953 sqft
49 Osprey Point Dr, Osprey, FL
Jonathan Abrams, PLLC · MICHAEL SAUNDERS & COMPANY
Price Reduced49$1,750,000
3 bd · 2 ba · 1,977 sqft
18 N Casey Key Rd, Osprey, FL
Valerie Dall'Acqua · PREMIER SOTHEBY'S INTERNATIONAL REALTY
Price Reduced66$6,475,000
4 bd · 6 ba · 4,096 sqft
121 N Casey Key Rd, Osprey, FL
Lisa Napolitano · DOUGLAS ELLIMAN









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 · 13 sales · as of Sep 29, 2026