New35$449,000
3 bd · 2 ba · 1,883 sqft
7303 Jessie Harbor Dr #7303, Osprey, FL
Mairead Smialek · COLDWELL BANKER REALTY
Homes for Sale in Osprey, FL
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24 of 43 Listings
New35$449,000
3 bd · 2 ba · 1,883 sqft
7303 Jessie Harbor Dr #7303, Osprey, FL
Mairead Smialek · COLDWELL BANKER REALTY
New100$695,000
3 bd · 3 ba · 2,594 sqft
385 N Point Rd #401, Osprey, FL
Steve Abbe · COLDWELL BANKER REALTY
New50$629,400
3 bd · 3 ba · 3,147 sqft
3603 N Point Rd #202, Osprey, FL
Mark Lyda · GENEROUS PROPERTY
55$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
59$165,000
2 bd · 2 ba · 924 sqft
23 Siesta Cir W, Osprey, FL
Karen Geiger · COLDWELL BANKER SARASOTA CENT.
100$700,000
3 bd · 3 ba · 2,680 sqft
3621 North Point Rd #403, 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
44$255,000
2 bd · 2 ba · 1,223 sqft
109 Woodland Pl, Osprey, FL
Monica DeSomma · PREFERRED SHORE LLC
43$585,000
3 bd · 2 ba · 1,705 sqft
2046 Cordes St, Osprey, FL
Sue Mondello · MICHAEL SAUNDERS & COMPANY
53$529,000
4 bd · 2 ba · 2,203 sqft
583 Pine Ranch East Rd, Osprey, FL
William Fortner · GALLERY PROPERTIES INTERNATIONAL
57$319,000
2 bd · 3 ba · 1,240 sqft
1819 Highland Rd, Osprey, FL
Jennifer Linehan · MICHAEL SAUNDERS & COMPANY
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
Price Reduced16$299,950
2 bd · 2 ba · 1,593 sqft
108 Villa Dr #108, Osprey, FL
Richard Gaspar · LOKATION
4$99,500
— bd · 0 ba · — sqft
570 Blackburn Point Rd #36, Osprey, FL
David Babel · BRIGHT REALTY
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
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
Price Reduced49$289,000
2 bd · 2 ba · 1,135 sqft
4296 Expedition Way #104, Osprey, FL
Pamela Kurpiewski · EXP REALTY LLC
Price Reduced37$185,000
2 bd · 2 ba · 1,199 sqft
320 Tropic Dr, Osprey, FL
Susan Retzke · RE/MAX PALM
71$275,000
1 bd · 1 ba · 623 sqft
51 Macewen Dr #12, Osprey, FL
Steve Abbe · COLDWELL BANKER REALTY
Price Reduced19$510,000
3 bd · 2 ba · 2,004 sqft
4429 Conchfish Ln, Osprey, FL
Jennifer Kenna · EXP REALTY, LLC
Stellar MLSSource: HJN community data
August 2026
Selling at 95.2% of asking price
Buyers here are paying below asking. MLS · 25 sales · as of Aug 31, 2026