34$159,900
1 bd · 1 ba · 586 sqft
717 Pine Run Dr. #717, Osprey, FL
Pat Williams · PAT WILLIAMS REALTY, LLC
Homes Under $600K in Osprey, FL
Hide MapHomes Under $600K in Osprey, FL
24 of 33 Listings
34$159,900
1 bd · 1 ba · 586 sqft
717 Pine Run Dr. #717, Osprey, FL
Pat Williams · PAT WILLIAMS REALTY, LLC
Open house Sun, Oct 4 · 1:00 PM35$449,000
3 bd · 2 ba · 1,883 sqft
7303 Jessie Harbor Dr #7303, Osprey, FL
Mairead Smialek · COLDWELL BANKER REALTY
55$540,000
3 bd · 2 ba · 2,248 sqft
1346 Thornapple Dr, Osprey, FL
Debra Robinson · RE/MAX ALLIANCE GROUP
59$165,000
2 bd · 2 ba · 924 sqft
23 Siesta Cir W, Osprey, FL
Karen Geiger · COLDWELL BANKER SARASOTA CENT.
Open house Sat, Oct 3 · 1:00 PM44$255,000
2 bd · 2 ba · 1,223 sqft
109 Woodland Pl, Osprey, FL
Monica DeSomma · PREFERRED SHORE LLC
Price Reduced43$565,000
3 bd · 2 ba · 1,705 sqft
2046 Cordes St, Osprey, FL
Sue Mondello · MICHAEL SAUNDERS & COMPANY
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
Open house Sun, Oct 4 · 1:00 PM62$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 ReducedOpen house Sat, Oct 3 · 1:00 PM45$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$499,999
3 bd · 2 ba · 2,004 sqft
4429 Conchfish Ln, Osprey, FL
Jennifer Kenna · EXP REALTY, LLC
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
4$36,000
— bd · 0 ba · — sqft
570 Blackburn Point Rd #26, Osprey, FL
David Babel · BRIGHT REALTY
Price Reduced95$525,000
3 bd · 3 ba · 2,680 sqft
3621 N Point Rd #301, Osprey, FL
Steve Abbe · COLDWELL BANKER REALTY
Homes Under $600K in Osprey, FL: 33 active listings as of .
| Property type | Listings | Share |
|---|---|---|
| Condominium | 15 | 45.5% |
| Boat Slip | 6 | 18.2% |
| Single Family Residence | 5 | 15.2% |
























Stellar MLSSeptember 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
Source: HJN community data