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
22 of 37 Listings
96$4,590,000
5 bd · 5 ba · 5,279 sqft
275 Lookout Point Dr, Osprey, FL
Natalie Gutwein · MICHAEL SAUNDERS & COMPANY
Open house Sun, Oct 4 · 1:00 PM59$799,000
3 bd · 3 ba · 2,678 sqft
1104 Mallard Marsh Dr, Osprey, FL
Todd Currey · PREMIER SOTHEBY'S INTERNATIONAL REALTY
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
19$655,000
3 bd · 3 ba · 2,792 sqft
700 Shadow Bay Way, Osprey, FL
Kara Money · KARA MONEY LLC
82$1,590,000
3 bd · 4 ba · 3,565 sqft
402 Macewen Dr, Osprey, FL
Steve Abbe · COLDWELL BANKER REALTY
99$2,175,000
4 bd · 4 ba · 4,117 sqft
362 Macewen Dr, Osprey, FL
Steve Abbe · COLDWELL BANKER REALTY
100$1,700,000
3 bd · 3 ba · 3,118 sqft
141 Sugar Mill Dr, Osprey, FL
Steve Abbe · COLDWELL BANKER REALTY
82$1,399,000
4 bd · 4 ba · 3,255 sqft
1417 Landview Ln, Osprey, FL
Pat Williams · PAT WILLIAMS REALTY, LLC
46$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
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
85$1,100,000
4 bd · 3 ba · 3,984 sqft
907 Eagle Isle Ct, Osprey, FL
Becky Culp · CENTURY 21 ROSEBAY
Price Reduced79$719,000
3 bd · 2 ba · 2,328 sqft
299 Turquoise Ln, Osprey, FL
Mickey Jordan · BRIGHT REALTY
45$824,900
4 bd · 3 ba · 2,607 sqft
Address withheld · Osprey, FL
Claudia Dybala · DALTON WADE INC
Price ReducedOpen house Sun, Oct 4 · 1:00 PM50$1,690,000
3 bd · 2 ba · 2,411 sqft
206 Four Knot Ln, Osprey, FL
65$4,790,000
4 bd · 6 ba · 5,087 sqft
101 Osprey Point Dr, Osprey, FL
Joel Schemmel · DOUGLAS ELLIMAN
Price Reduced39$719,000
3 bd · 2 ba · 1,937 sqft
280 Hidden Bay Dr #302, Osprey, FL
Jim Xarras, Jr · BERKSHIRE HATHAWAY HOMESERVICE
81$1,289,000
3 bd · 4 ba · 3,112 sqft
156 Bishops Court Rd, Osprey, FL
Joel Schemmel · DOUGLAS ELLIMAN
61$1,950,000
5 bd · 6 ba · 4,885 sqft
97 Sugar Mill Dr, Osprey, FL
Maria Domenech · PALM PARADISE REALTY GROUP
Homes with a Pool in Osprey, FL: 37 active listings as of .
Florida Gulf Coast MLS/Royal Palm Coast Realtor Association(SWFLMLS)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