280 Days on Market
House for Sale
$499,900
3 bd · 2 ba · 1,293 sqft
Bedrooms
Bathrooms
Osprey Homes for Sale under $500K
35 listings
68 Days on Market
House for Sale
$499,000
3 bd · 2 ba · 1,874 sqft
447 N SHORE DRIVE, OSPREY, FL 34229
32 Days on Market
Condo for Sale
$497,000
3 bd · 3 ba · 2,006 sqft
2309 JESSIE HARBOR DRIVE # 2402, OSPREY, FL 34229
667 Days on Market
Condo for Sale
$459,900
3 bd · 3 ba · 2,594 sqft
401 N POINT ROAD # 301, OSPREY, FL 34229
Newly Listed
Home for Sale
$425,000
2 bd · 2 ba · 1,574 sqft
780 SARABAY ROAD # 16, OSPREY, FL 34229
58 Days on Market
House for Sale
$425,000
2 bd · 2 ba · 1,284 sqft
107 SORRENTO DRIVE, OSPREY, FL 34229
56 Days on Market
House for Sale
$420,000
3 bd · 2 ba · 1,478 sqft
212 WASHINGTON AVENUE, OSPREY, FL 34229
22 Days on Market
House for Sale
$419,000
2 bd · 2 ba · 1,346 sqft
329 BAY VISTA AVENUE, OSPREY, FL 34229
186 Days on Market
House for Sale
$419,000
3 bd · 2 ba · 1,760 sqft
524 SARABAY ROAD, OSPREY, FL 34229
435 Days on Market
House for Sale
$417,000
3 bd · 2 ba · 1,300 sqft
352 GLENWOOD AVE, OSPREY, FL 34229
280 Days on Market
Townhome for Sale
$417,000
2 bd · 2 ba · 1,725 sqft
1811 HIGHLAND ROAD, OSPREY, FL 34229
42 Days on Market
Condo for Sale
$395,000
2 bd · 2 ba · 1,255 sqft
7204 JESSIE HARBOR DRIVE # 7204, OSPREY, FL 34229
77 Days on Market
Condo for Sale
$320,000
2 bd · 2 ba · 1,449 sqft
89 NAVIGATION CIRCLE, OSPREY, FL 34229
28 Days on Market
Condo for Sale
$319,500
3 bd · 2 ba · 1,528 sqft
173 NAVIGATION CIRCLE # 107, OSPREY, FL 34229
37 Days on Market
Condo for Sale
$317,000
3 bd · 2 ba · 1,430 sqft
4213 EXPEDITION WAY # 107, OSPREY, FL 34229
Newly Listed
Townhome for Sale
$299,990
2 bd · 2 ba · 1,135 sqft
4296 EXPEDITION WAY # 104, OSPREY, FL 34229
112 Days on Market
Condo for Sale
$299,000
2 bd · 2 ba · 1,135 sqft
4226 FRONTIER LANE # 103, OSPREY, FL 34229
Newly Listed
Townhome for Sale
$294,900
2 bd · 2 ba · 1,244 sqft
184 EXPLORER DRIVE, OSPREY, FL 34229
314 Days on Market
Townhome for Sale
$289,900
2 bd · 2 ba · 1,165 sqft
1801 HIGHLAND ROAD, OSPREY, FL 34229
45 Days on Market
Condo for Sale
$285,000
1 bd · 1 ba · 595 sqft
51 MAC EWEN DRIVE # 14, OSPREY, FL 34229
30 Days on Market
Condo for Sale
$285,000
2 bd · 2 ba · 1,316 sqft
108 WOODLAND PLACE # 108, OSPREY, FL 34229
Newly Listed
Condo for Sale
$275,000
1 bd · 1 ba · 623 sqft
51 MACEWEN DRIVE # 12, OSPREY, FL 34229
104 Days on Market
Condo for Sale
$260,000
2 bd · 2 ba · 1,135 sqft
4271 EXPEDITION WAY # 103, OSPREY, FL 34229
54 Days on Market
Condo for Sale
$254,900
2 bd · 2 ba · 1,325 sqft
116 WOODLAND PLACE # 116, OSPREY, FL 34229
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Live MLS inventory in Osprey, updated continuously. Florida Lux Real Estate currently tracks 35 active listings here. MLS inventory updated October 12, 2026.
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