7$149,900
— bd · 0 ba · — sqft
570 Blackburn Point Rd #Siesta 25, Osprey, FL
David Babel · BRIGHT REALTY
Homes Under $500K in Osprey, FL
Hide MapHomes Under $500K in Osprey, FL
24 of 26 Listings
7$149,900
— bd · 0 ba · — sqft
570 Blackburn Point Rd #Siesta 25, Osprey, FL
David Babel · BRIGHT REALTY
36$465,000
2 bd · 2 ba · 1,404 sqft
120 Villa Dr #120, Osprey, FL
Antonio Lopez · MANGROVE REALTY ASSOCIATES
31$175,000
2 bd · 2 ba · 960 sqft
145 Edgewood Dr, Osprey, FL
Mark Lyda · GENEROUS PROPERTY
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 18 · 1:00 PM35$449,000
3 bd · 2 ba · 1,883 sqft
7303 Jessie Harbor Dr #7303, Osprey, FL
Mairead Smialek · COLDWELL BANKER REALTY
59$165,000
2 bd · 2 ba · 924 sqft
23 Siesta Cir W, Osprey, FL
Karen Geiger · COLDWELL BANKER SARASOTA CENT.
Price Reduced44$244,900
2 bd · 2 ba · 1,223 sqft
109 Woodland Pl, Osprey, FL
Monica DeSomma · PREFERRED SHORE LLC
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
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 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 Reduced41$419,000
3 bd · 2 ba · 1,760 sqft
524 Sarabay Rd, Osprey, FL
Ibett Giannone · SUN N SAND REAL ESTATE LLC
4$115,000
— bd · 0 ba · — sqft
570 Blackburn Point Rd #43, Osprey, FL
David Babel · BRIGHT REALTY
4$109,000
— bd · 0 ba · — sqft
570 Blackburn Point Rd #13, Osprey, FL
David Babel · BRIGHT REALTY
Price Reduced19$399,000
2 bd · 2 ba · 1,725 sqft
1811 Highland Rd, Osprey, FL
Stephen Hachey · REALTY OF RIVERVIEW LLC
Price Reduced34$104,900
2 bd · 2 ba · 864 sqft
348 Tropic Dr, Osprey, FL
John Alexander · FINE PROPERTIES
Homes Under $500K in Osprey, FL: 26 active listings as of .
| Property type | Listings | Share |
|---|---|---|
| Condominium | 11 | 42.3% |
| Boat Slip | 7 | 26.9% |
























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