62$599,000
2 bd · 2 ba · 2,143 sqft
5100 Jessie Harbor Dr #404, Osprey, FL
Stuart Lawrence · MICHAEL SAUNDERS & COMPANY
Homes Under $1.25M in Osprey, FL
Hide MapHomes Under $1.25M in Osprey, FL
24 of 67 Listings
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 Reduced79$699,000
3 bd · 2 ba · 2,328 sqft
299 Turquoise Ln, Osprey, FL
Mickey Jordan · BRIGHT REALTY
58$775,000
3 bd · 3 ba · 1,950 sqft
260 Hidden Bay Dr #402, Osprey, FL
Thomas Netzel · PREMIER SOTHEBY'S INTERNATIONAL REALTY
Open house Sun, Oct 18 · 12:00 PM54$630,000
4 bd · 2 ba · 2,186 sqft
1036 Oak Meadow Ln, Osprey, FL
Curtis Andrews · BETTER HOMES AND GARDENS REAL ESTATE ATCHLEY PROPE
4$99,500
— bd · 0 ba · — sqft
570 Blackburn Point Rd #36, Osprey, FL
David Babel · BRIGHT REALTY
54$425,000
2 bd · 2 ba · 1,574 sqft
780 Sarabay Rd #16, Osprey, FL
Mark Segreto · RMS ELITE PROPERTIES
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 Reduced55$699,000
3 bd · 2 ba · 2,034 sqft
103 Bishops Court Rd, Osprey, FL
Mark Lyda · GENEROUS PROPERTY
Price Reduced39$745,000
3 bd · 2 ba · 1,937 sqft
280 Hidden Bay Dr #302, Osprey, FL
Jim Xarras, Jr · BERKSHIRE HATHAWAY HOMESERVICE
71$275,000
1 bd · 1 ba · 623 sqft
51 Macewen Dr #12, Osprey, FL
Steve Abbe · COLDWELL BANKER REALTY
Price Reduced83$798,000
3 bd · 4 ba · 3,771 sqft
6100 Jessie Harbor Dr #202, Osprey, FL
Angelic Tassos · CORCORAN DWELLINGS REALTY
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$1,100,000
3 bd · 3 ba · 2,830 sqft
1527 Buoy Ln, Osprey, FL
Matthew Lewis · BRIGHT REALTY
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 · 16 sales · as of Sep 30, 2026