Osprey Condos for Sale under $500K

15 listings
2309 JESSIE HARBOR DRIVE # 2402, 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

401 N POINT ROAD # 301, 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

7204 JESSIE HARBOR DRIVE # 7204, 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

89 NAVIGATION CIRCLE, 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

173 NAVIGATION CIRCLE # 107, 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

4213 EXPEDITION WAY # 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

4226 FRONTIER LANE # 103, 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

108 WOODLAND PLACE # 108, 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

51 MAC EWEN DRIVE # 14, 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

51 MACEWEN DRIVE # 12, OSPREY, FL 34229
Newly Listed

Condo for Sale

$275,000

1 bd · 1 ba · 623 sqft

51 MACEWEN DRIVE # 12, OSPREY, FL 34229

4271 EXPEDITION WAY # 103, 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

116 WOODLAND PLACE # 116, 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

51 MACEWEN DRIVE # 5, OSPREY, FL 34229
21 Days on Market

Condo for Sale

$235,000

1 bd · 1 ba · 595 sqft

51 MACEWEN DRIVE # 5, OSPREY, FL 34229

110 WOODLAND PLACE # 110, OSPREY, FL 34229
18 Days on Market

Condo for Sale

$215,000

2 bd · 2 ba · 1,325 sqft

110 WOODLAND PLACE # 110, OSPREY, FL 34229

701 PINE RUN DRIVE # 701, OSPREY, FL 34229
Newly Listed

Condo for Sale

$172,000

1 bd · 1 ba · 586 sqft

701 PINE RUN DRIVE # 701, OSPREY, FL 34229

Talk to a local agent

Looking at Osprey Condos for Sale under $500K?

Tell us what you're after — we'll send matching homes, off-market options and recent sales, and set up private showings.

Matthew Gromadzki, Real Estate Broker
Matthew Gromadzki
Real Estate Broker
(786) 370-8570
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Live MLS inventory in Osprey, updated continuously. Florida Lux Real Estate currently tracks 15 active listings here. MLS inventory updated October 12, 2026.

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