Winter Park Condos for Sale under $500K

72 listings
1500 GAY ROAD # 17D, WINTER PARK, FL 32789
80 Days on Market

Condo for Sale

$239,500

2 bd · 2 ba · 1,026 sqft

1500 GAY ROAD # 17D, WINTER PARK, FL 32789

200 SAINT ANDREWS BOULEVARD # 2904, WINTER PARK, FL 32792
14 Days on Market

Condo for Sale

$230,000

2 bd · 2 ba · 1,219 sqft

200 SAINT ANDREWS BOULEVARD # 2904, WINTER PARK, FL 32792

7413 BELLE RIVER COURT # 3, WINTER PARK, FL 32792
Newly Listed

Condo for Sale

$229,900

3 bd · 3 ba · 1,151 sqft

7413 BELLE RIVER COURT # 3, WINTER PARK, FL 32792

7454 WYNNEWOOD SQUARE # 188, WINTER PARK, FL 32792
Newly Listed

Condo for Sale

$229,000

3 bd · 3 ba · 1,151 sqft

7454 WYNNEWOOD SQUARE # 188, WINTER PARK, FL 32792

2503 TAHOE CIRCLE # 2503, WINTER PARK, FL 32792
69 Days on Market

Condo for Sale

$225,000

2 bd · 2 ba · 1,173 sqft

2503 TAHOE CIRCLE # 2503, WINTER PARK, FL 32792

7488 WHISPERWOOD DRIVE # 28, WINTER PARK, FL 32792
38 Days on Market

Condo for Sale

$210,000

2 bd · 3 ba · 1,578 sqft

7488 WHISPERWOOD DRIVE # 28, WINTER PARK, FL 32792

1695 LEE ROAD # C202, WINTER PARK, FL 32789
415 Days on Market

Condo for Sale

$205,000

3 bd · 2 ba · 1,149 sqft

1695 LEE ROAD # C202, WINTER PARK, FL 32789

151 NORTH ORLANDO AVENUE # 142, WINTER PARK, FL 32789
49 Days on Market

Condo for Sale

$199,900

1 bd · 1 ba · 582 sqft

151 NORTH ORLANDO AVENUE # 142, WINTER PARK, FL 32789

2500 LEE ROAD # 220, WINTER PARK, FL 32789
Newly Listed

Condo for Sale

$199,900

2 bd · 1 ba · 851 sqft

2500 LEE ROAD # 220, WINTER PARK, FL 32789

7471 CANFORD COURT # 19, WINTER PARK, FL 32792
215 Days on Market

Condo for Sale

$199,000

2 bd · 2 ba · 1,393 sqft

7471 CANFORD COURT # 19, WINTER PARK, FL 32792

1250 S DENNING DRIVE # 109, WINTER PARK, FL 32789
27 Days on Market

Condo for Sale

$190,000

1 bd · 1 ba · 658 sqft

1250 S DENNING DRIVE # 109, WINTER PARK, FL 32789

7450 WYNNEWOOD SQUARE # 189, WINTER PARK, FL 32792
12 Days on Market

Condo for Sale

$185,000

2 bd · 3 ba · 1,031 sqft

7450 WYNNEWOOD SQUARE # 189, WINTER PARK, FL 32792

4756 TANGERINE AVENUE # 4756, WINTER PARK, FL 32792
32 Days on Market

Condo for Sale

$185,000

2 bd · 2 ba · 1,058 sqft

4756 TANGERINE AVENUE # 4756, WINTER PARK, FL 32792

2500 LEE RD. # 222, WINTER PARK, FL 32789
181 Days on Market

Condo for Sale

$184,900

1 bd · 1 ba · 645 sqft

2500 LEE RD. # 222, WINTER PARK, FL 32789

205 LEWFIELD CIRCLE # 205, WINTER PARK, FL 32792
207 Days on Market

Condo for Sale

$182,900

2 bd · 2 ba · 927 sqft

205 LEWFIELD CIRCLE # 205, WINTER PARK, FL 32792

2923 ANTIQUE OAKS CIRCLE # 34, WINTER PARK, FL 32792
54 Days on Market

Condo for Sale

$180,000

2 bd · 2 ba · 1,105 sqft

2923 ANTIQUE OAKS CIRCLE # 34, WINTER PARK, FL 32792

1695 LEE ROAD # D107, WINTER PARK, FL 32789
Newly Listed

Condo for Sale

$180,000

1 bd · 1 ba · 638 sqft

1695 LEE ROAD # D107, WINTER PARK, FL 32789

7327 FOREST HILL COURT # 223, WINTER PARK, FL 32792
85 Days on Market

Condo for Sale

$175,000

2 bd · 3 ba · 1,031 sqft

7327 FOREST HILL COURT # 223, WINTER PARK, FL 32792

4768 TANGERINE AVENUE # 4768, WINTER PARK, FL 32792
133 Days on Market

Condo for Sale

$174,900

1 bd · 1 ba · 753 sqft

4768 TANGERINE AVENUE # 4768, WINTER PARK, FL 32792

3243 FOREST OAKS COURT # 117, WINTER PARK, FL 32792
41 Days on Market

Condo for Sale

$172,000

2 bd · 2 ba · 990 sqft

3243 FOREST OAKS COURT # 117, WINTER PARK, FL 32792

1500 GAY ROAD # 4D, WINTER PARK, FL 32789
25 Days on Market

Condo for Sale

$169,900

1 bd · 1 ba · 732 sqft

1500 GAY ROAD # 4D, WINTER PARK, FL 32789

200 SAINT ANDREWS BOULEVARD # 704, WINTER PARK, FL 32792
Newly Listed

Condo for Sale

$164,999

1 bd · 1 ba · 793 sqft

200 SAINT ANDREWS BOULEVARD # 704, WINTER PARK, FL 32792

7300 DANIEL WEBSTER DRIVE # M7, WINTER PARK, FL 32792
74 Days on Market

Condo for Sale

$159,000

2 bd · 3 ba · 1,108 sqft

7300 DANIEL WEBSTER DRIVE # M7, WINTER PARK, FL 32792

3027 AARON BURR AVENUE # L1, WINTER PARK, FL 32792
74 Days on Market

Condo for Sale

$159,000

2 bd · 3 ba · 1,090 sqft

3027 AARON BURR AVENUE # L1, WINTER PARK, FL 32792

Talk to a local agent

Looking at Winter Park 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 Winter Park, updated continuously. Florida Lux Real Estate currently tracks 72 active listings here. MLS inventory updated October 28, 2026.

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