73 Days on Market
House for Sale
$4,790,000
4 bd · 6 ba · 5,087 sqft
Bedrooms
Bathrooms
Osprey Homes for Sale under $5M
92 listings
252 Days on Market
House for Sale
$3,640,000
4 bd · 6 ba · 9,081 sqft
854 MACEWEN DRIVE, OSPREY, FL 34229
50 Days on Market
House for Sale
$3,295,000
3 bd · 5 ba · 2,572 sqft
135 TINA ISLAND DRIVE, OSPREY, FL 34229
95 Days on Market
House for Sale
$2,995,000
3 bd · 4 ba · 2,665 sqft
14401 MASTHEAD DRIVE, OSPREY, FL 34229
405 Days on Market
House for Sale
$2,700,000
6 bd · 7 ba · 6,246 sqft
236 SAINT JAMES PARK, OSPREY, FL 34229
187 Days on Market
House for Sale
$2,399,000
4 bd · 4 ba · 3,953 sqft
49 OSPREY POINT DRIVE, OSPREY, FL 34229
298 Days on Market
House for Sale
$2,395,000
3 bd · 4 ba · 4,519 sqft
852 MACEWEN DRIVE, OSPREY, FL 34229
259 Days on Market
House for Sale
$2,199,900
5 bd · 4 ba · 3,236 sqft
180 LOOKOUT POINT DRIVE, OSPREY, FL 34229
176 Days on Market
Condo for Sale
$1,995,000
3 bd · 3 ba · 3,029 sqft
401 N POINT ROAD # 1001, OSPREY, FL 34229
180 Days on Market
House for Sale
$1,950,000
4 bd · 6 ba · 4,346 sqft
538 DOVE POINTE DRIVE, OSPREY, FL 34229
95 Days on Market
House for Sale
$1,950,000
5 bd · 6 ba · 4,885 sqft
97 SUGAR MILL DRIVE, OSPREY, FL 34229
Newly Listed
House for Sale
$1,900,000
5 bd · 8 ba · 5,986 sqft
916 MACEWEN DRIVE, OSPREY, FL 34229
44 Days on Market
House for Sale
$1,790,000
3 bd · 2 ba · 2,411 sqft
206 FOUR KNOT LANE, OSPREY, FL 34229
48 Days on Market
House for Sale
$1,649,000
4 bd · 4 ba · 4,001 sqft
75 OSPREY POINT DRIVE, OSPREY, FL 34229
592 Days on Market
House for Sale
$1,595,000
3 bd · 4 ba · 4,241 sqft
909 MACEWEN DRIVE, OSPREY, FL 34229
150 Days on Market
House for Sale
$1,500,000
3 bd · 4 ba · 3,208 sqft
480 ORISKANY COURT, OSPREY, FL 34229
Newly Listed
House for Sale
$1,495,000
3 bd · 4 ba · 2,913 sqft
360 N POINT ROAD, OSPREY, FL 34229
486 Days on Market
Condo for Sale
$1,395,000
3 bd · 3 ba · 2,545 sqft
3603 N POINT ROAD # 702, OSPREY, FL 34229
91 Days on Market
House for Sale
$1,289,000
3 bd · 4 ba · 3,112 sqft
156 BISHOPS COURT ROAD, OSPREY, FL 34229
180 Days on Market
Condo for Sale
$1,250,000
3 bd · 3 ba · 2,594 sqft
409 N POINT ROAD # 601, OSPREY, FL 34229
258 Days on Market
House for Sale
$1,200,000
4 bd · 3 ba · 2,474 sqft
700 FAITH AVENUE, OSPREY, FL 34229
77 Days on Market
House for Sale
$1,165,000
3 bd · 3 ba · 2,830 sqft
1527 BUOY LANE, OSPREY, FL 34229
179 Days on Market
Condo for Sale
$1,100,000
3 bd · 3 ba · 2,778 sqft
385 N POINT ROAD # 304, OSPREY, FL 34229
71 Days on Market
Condo for Sale
$1,100,000
3 bd · 3 ba · 2,187 sqft
14021 BELLAGIO WAY # 404, OSPREY, FL 34229
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Live MLS inventory in Osprey, updated continuously. Florida Lux Real Estate currently tracks 92 active listings here. MLS inventory updated October 11, 2026.
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