78$1,100,000
4 bd · 3 ba · 2,770 sqft
403 Longbow Trl, Osprey, FL
Carlos Santos · PREMIER SOTHEBY'S INTERNATIONAL REALTY
Homes with a Pool in Osprey, FL
Show MapHomes with a Pool in Osprey, FL
24 of 38 Listings
78$1,100,000
4 bd · 3 ba · 2,770 sqft
403 Longbow Trl, Osprey, FL
Carlos Santos · PREMIER SOTHEBY'S INTERNATIONAL REALTY
67$3,190,000
5 bd · 6 ba · 5,218 sqft
871 Macewen Dr, Osprey, FL
Katy McBrayer · PREMIER SOTHEBY'S INTERNATIONAL REALTY
89$600,000
4 bd · 3 ba · 3,192 sqft
455 Oak Point Rd, Osprey, FL
Todd Currey · PREMIER SOTHEBY'S INTERNATIONAL REALTY
51$799,000
4 bd · 3 ba · 2,474 sqft
819 Golden Pond Ct, Osprey, FL
Dana Cook Westmark · MICHAEL SAUNDERS & COMPANY
59$1,900,000
3 bd · 4 ba · 3,924 sqft
168 Coastal Hammock Ct, Osprey, FL
Lenore Treiman · MICHAEL SAUNDERS & COMPANY
79$1,485,999
4 bd · 3 ba · 3,246 sqft
1474 Landview Ln, Osprey, FL
Angela Fowler · ANGELA FOWLER REAL ESTATE, LLC
95$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
56$1,049,000
4 bd · 3 ba · 2,775 sqft
366 S Creek Ct, Osprey, FL
EJ Stukenborg · KELLER WILLIAMS ON THE WATER S
95$1,445,000
3 bd · 4 ba · 3,872 sqft
422 Blue Garden Ln, Osprey, FL
Steve Abbe · 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$3,700,000
4 bd · 4 ba · 4,314 sqft
650 Oaks Creek Ct, Osprey, FL
Steve Abbe · COLDWELL BANKER REALTY
59$1,399,000
3 bd · 3 ba · 2,695 sqft
256 Sugar Mill, Osprey, FL
Ivan Bovkun · KIMBERLITE WEST REALTY LLC
100$3,700,000
5 bd · 5 ba · 6,234 sqft
324 Osprey Point Dr, Osprey, FL
Steve Abbe · COLDWELL BANKER REALTY
Price Reduced82$1,349,999
4 bd · 4 ba · 3,255 sqft
1417 Landview Ln, Osprey, FL
Pat Williams · PAT WILLIAMS REALTY, LLC
Price Reduced46$719,900
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
Price Reduced50$2,095,000
4 bd · 4 ba · 4,578 sqft
154 Lookout Point Dr, Osprey, FL
Stephen Hachey · FLAT FEE MLS REALTY
100$1,100,000
5 bd · 4 ba · 3,354 sqft
296 Pine Ranch Trl, Osprey, FL
Darren Dowling · BEYOND REALTY LLC
Price Reduced79$699,000
3 bd · 2 ba · 2,328 sqft
299 Turquoise Ln, Osprey, FL
Mickey Jordan · BRIGHT REALTY
Price Reduced70$1,595,000
4 bd · 4 ba · 4,001 sqft
75 Osprey Point Dr, Osprey, FL
Steve Abbe · COLDWELL BANKER REALTY
65$4,790,000
4 bd · 6 ba · 5,087 sqft
101 Osprey Point Dr, Osprey, FL
Joel Schemmel · DOUGLAS ELLIMAN
Price Reduced39$745,000
3 bd · 2 ba · 1,937 sqft
280 Hidden Bay Dr #302, Osprey, FL
Jim Xarras, Jr · BERKSHIRE HATHAWAY HOMESERVICE
Stellar MLSSource: HJN community data
September 2026
Selling at 96.2% of asking price
Buyers here are paying below asking. MLS · 16 sales · as of Sep 30, 2026