65$4,790,000
4 bd · 6 ba · 5,087 sqft
101 Osprey Point Dr, Osprey, FL
Joel Schemmel · DOUGLAS ELLIMAN
Homes for Sale in Osprey, FL
Hide MapHomes for Sale in Osprey, FL
24 of 95 Listings
65$4,790,000
4 bd · 6 ba · 5,087 sqft
101 Osprey Point Dr, Osprey, FL
Joel Schemmel · DOUGLAS ELLIMAN
55$749,000
3 bd · 2 ba · 2,034 sqft
103 Bishops Court Rd, Osprey, FL
Mark Lyda · GENEROUS PROPERTY
Price Reduced37$185,000
2 bd · 2 ba · 1,199 sqft
320 Tropic Dr, Osprey, FL
Susan Retzke · RE/MAX PALM
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
71$275,000
1 bd · 1 ba · 623 sqft
51 Macewen Dr #12, Osprey, FL
Steve Abbe · COLDWELL BANKER REALTY
47$3,295,000
3 bd · 5 ba · 2,572 sqft
135 Tina Island Dr, Osprey, FL
Mark Lyda · GENEROUS PROPERTY
Price Reduced83$798,000
3 bd · 4 ba · 3,771 sqft
6100 Jessie Harbor Dr #202, Osprey, FL
Angelic Tassos · CORCORAN DWELLINGS REALTY
61$1,950,000
5 bd · 6 ba · 4,885 sqft
97 Sugar Mill Dr, Osprey, FL
Maria Domenech · PALM PARADISE REALTY GROUP
Price Reduced19$499,999
3 bd · 2 ba · 2,004 sqft
4429 Conchfish Ln, Osprey, FL
Jennifer Kenna · EXP REALTY, LLC
Price Reduced70$999,900
3 bd · 3 ba · 2,187 sqft
14021 Bellagio Way #404, Osprey, FL
Megan E. George, PA · PREMIER SOTHEBYS INTL REALTY
Price Reduced90$560,000
3 bd · 3 ba · 2,594 sqft
409 North Point Rd #401, Osprey, FL
Steve Abbe · COLDWELL BANKER REALTY
Price Reduced44$235,000
1 bd · 1 ba · 595 sqft
51 Macewen Dr #5, Osprey, FL
Sabine Spycher · 342 REAL ESTATE
19$285,000
1 bd · 1 ba · 595 sqft
51 Mac Ewen Dr #14, Osprey, FL
Steve Abbe · COLDWELL BANKER REALTY
Price Reduced51$700,000
4 bd · 4 ba · 2,950 sqft
759 Fordingbridge Way, Osprey, FL
Steven Koleno · BEYCOME OF FLORIDA LLC
50$700,000
3 bd · 2 ba · 1,799 sqft
14041 Bellagio Way #214, Osprey, FL
Veronica Lee · COLDWELL BANKER REALTY
Price Reduced52$1,165,000
3 bd · 3 ba · 2,830 sqft
1527 Buoy Ln, Osprey, FL
Matthew Lewis · BRIGHT REALTY
100$5,999,999
4 bd · 5 ba · 5,337 sqft
313 Lookout Point Dr, Osprey, FL
Natalie Gutwein · MICHAEL SAUNDERS & COMPANY
4$36,000
— bd · 0 ba · — sqft
570 Blackburn Point Rd #26, Osprey, FL
David Babel · BRIGHT REALTY
Price Reduced38$879,000
3 bd · 3 ba · 2,199 sqft
14021 Bellagio Way #309, Osprey, FL
Tristin Hopler · COMPASS FLORIDA, LLC
Price Reduced95$525,000
3 bd · 3 ba · 2,680 sqft
3621 N Point Rd #301, Osprey, FL
Steve Abbe · COLDWELL BANKER REALTY
63$1,250,000
3 bd · 3 ba · 2,594 sqft
409 N Point Rd #601, Osprey, FL
Mark Lyda · GENEROUS PROPERTY
60$1,995,000
3 bd · 3 ba · 3,029 sqft
401 N Point Rd #1001, Osprey, FL
Mark Lyda · GENEROUS PROPERTY
Price Reduced36$700,000
2 bd · 2 ba · 1,932 sqft
242 Hidden Bay Dr #602, Osprey, FL
Cathy Rustin · FIRST LIGHT REAL ESTATE
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