53$529,000
4 bd · 2 ba · 2,203 sqft
583 Pine Ranch East Rd, Osprey, FL
William Fortner · GALLERY PROPERTIES INTERNATIONAL
Homes for Sale in Osprey, FL
Hide MapHomes for Sale in Osprey, FL
22 of 94 Listings
53$529,000
4 bd · 2 ba · 2,203 sqft
583 Pine Ranch East Rd, Osprey, FL
William Fortner · GALLERY PROPERTIES INTERNATIONAL
89$1,495,000
3 bd · 3 ba · 2,591 sqft
226 Saint James Park, Osprey, FL
Justin Brunswick · KELLER WILLIAMS ON THE WATER S
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
57$319,000
2 bd · 3 ba · 1,240 sqft
1819 Highland Rd, Osprey, FL
Jennifer Linehan · MICHAEL SAUNDERS & COMPANY
85$1,100,000
4 bd · 3 ba · 3,984 sqft
907 Eagle Isle Ct, Osprey, FL
Becky Culp · CENTURY 21 ROSEBAY
11$540,000
3 bd · 3 ba · 2,040 sqft
1140 Beachcomber Ct #11, Osprey, FL
Ralph Harvey · LISTWITHFREEDOM.COM
62$599,000
2 bd · 2 ba · 2,143 sqft
5100 Jessie Harbor Dr #404, Osprey, FL
Stuart Lawrence · MICHAEL SAUNDERS & COMPANY
60$985,000
3 bd · 3 ba · 2,203 sqft
409 N Point Rd #803, Osprey, FL
Mark Lyda · GENEROUS PROPERTY
Price Reduced16$299,950
2 bd · 2 ba · 1,593 sqft
108 Villa Dr #108, Osprey, FL
Richard Gaspar · LOKATION
58$775,000
3 bd · 3 ba · 1,950 sqft
260 Hidden Bay Dr #402, Osprey, FL
Thomas Netzel · PREMIER SOTHEBY'S INTERNATIONAL REALTY
Price Reduced79$719,000
3 bd · 2 ba · 2,328 sqft
299 Turquoise Ln, Osprey, FL
Mickey Jordan · BRIGHT REALTY
4$99,500
— bd · 0 ba · — sqft
570 Blackburn Point Rd #36, Osprey, FL
David Babel · BRIGHT REALTY
45$824,900
4 bd · 3 ba · 2,607 sqft
Address withheld · Osprey, FL
Claudia Dybala · DALTON WADE INC
Price Reduced85$480,000
3 bd · 3 ba · 2,006 sqft
2309 Jessie Harbor Dr #2402, Osprey, FL
Christine Pope · MICHAEL SAUNDERS & COMPANY
Price Reduced3$89,000
— bd · 0 ba · — sqft
570 Blackburn Point Rd #23, Osprey, FL
Daniel Treiman · MICHAEL SAUNDERS & COMPANY
Price Reduced50$1,690,000
3 bd · 2 ba · 2,411 sqft
206 Four Knot Ln, Osprey, FL
43$395,000
2 bd · 2 ba · 1,255 sqft
7204 Jessie Harbor Dr #7204, Osprey, FL
Mark Lyda · GENEROUS PROPERTY
Price Reduced45$249,900
2 bd · 2 ba · 1,325 sqft
116 Woodland Pl #116, Osprey, FL
Pat Williams · PAT WILLIAMS REALTY, LLC
49$1,495,000
3 bd · 4 ba · 2,913 sqft
360 N Point Rd, Osprey, FL
Steve Abbe · COLDWELL BANKER REALTY
Price Reduced49$289,000
2 bd · 2 ba · 1,135 sqft
4296 Expedition Way #104, Osprey, FL
Pamela Kurpiewski · EXP REALTY LLC
65$4,790,000
4 bd · 6 ba · 5,087 sqft
101 Osprey Point Dr, Osprey, FL
Joel Schemmel · DOUGLAS ELLIMAN
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