9 Days on Market
Townhome for Sale
$299,999
3 bd · 2 ba · 1,324 sqft
Bedrooms
Bathrooms
Winter Park Homes for Sale under $300K
73 listings
12 Days on Market
Townhome for Sale
$290,000
3 bd · 3 ba · 1,803 sqft
2487 HARBOUR WAY, WINTER PARK, FL 32792
247 Days on Market
Condo for Sale
$290,000
2 bd · 1 ba · 710 sqft
151 N ORLANDO AVENUE # #115, WINTER PARK, FL 32789
Newly Listed
Condo for Sale
$289,900
2 bd · 3 ba · 1,236 sqft
5210 LAZY OAKS DRIVE # 5210, WINTER PARK, FL 32792
49 Days on Market
Home for Sale
$289,000
2 bd · 2 ba · 1,140 sqft
5806 MARBLE COURT, WINTER PARK, FL 32792
14 Days on Market
Condo for Sale
$285,000
2 bd · 2 ba · 1,495 sqft
2372 SUN VALLEY CIRCLE # 2372, WINTER PARK, FL 32792
300 Days on Market
Condo for Sale
$285,000
2 bd · 2 ba · 1,669 sqft
2336 SUN VALLEY CIRCLE # BLDG 20, WINTER PARK, FL 32792
170 Days on Market
Condo for Sale
$284,900
1 bd · 1 ba · 482 sqft
311 E MORSE BOULEVARD # 7-19, WINTER PARK, FL 32789
Newly Listed
Condo for Sale
$280,000
2 bd · 2 ba · 1,008 sqft
5184 LAZY OAKS DRIVE, WINTER PARK, FL 32792
29 Days on Market
Condo for Sale
$279,900
2 bd · 2 ba · 1,295 sqft
2305 SUN VALLEY CIR, WINTER PARK, FL 32792, WINTER PARK, FL 32792
342 Days on Market
Condo for Sale
$279,000
1 bd · 1 ba · 570 sqft
311 E MORSE BOULEVARD # 7-11, WINTER PARK, FL 32789
8 Days on Market
Condo for Sale
$278,000
2 bd · 2 ba · 1,295 sqft
2475 TAHOE CIRCLE # 2475, WINTER PARK, FL 32792
Newly Listed
Condo for Sale
$275,000
1 bd · 1 ba · 570 sqft
311 E MORSE BOULEVARD # 6-12, WINTER PARK, FL 32789
96 Days on Market
Condo for Sale
$275,000
2 bd · 2 ba · 1,008 sqft
5143 LAZY OAKS DRIVE # 5143, WINTER PARK, FL 32792
144 Days on Market
Home for Sale
$268,950
2 bd · 2 ba · 1,036 sqft
3220 NETHERWOOD DRIVE, WINTER PARK, FL 32792
104 Days on Market
Condo for Sale
$267,000
2 bd · 2 ba · 1,295 sqft
2317 SUN VALLEY CIRCLE # 2317, WINTER PARK, FL 32792
Newly Listed
Condo for Sale
$259,000
3 bd · 3 ba · 1,720 sqft
2433 GRAND TETON CIRCLE, WINTER PARK, FL 32792
113 Days on Market
Condo for Sale
$258,000
2 bd · 2 ba · 1,026 sqft
1500 GAY ROAD # 20D, WINTER PARK, FL 32789
Newly Listed
Condo for Sale
$255,000
3 bd · 2 ba · 1,311 sqft
2450 GRAND TETON CIRCLE # 2450, WINTER PARK, FL 32792
47 Days on Market
Townhome for Sale
$255,000
2 bd · 2 ba · 1,020 sqft
2651 CAYMAN WAY, WINTER PARK, FL 32792
58 Days on Market
Condo for Sale
$249,900
2 bd · 2 ba · 956 sqft
2500 LEE ROAD # 104, WINTER PARK, FL 32789
12 Days on Market
Condo for Sale
$248,900
2 bd · 3 ba · 1,300 sqft
193 LEWFIELD CIRCLE, WINTER PARK, FL 32792
110 Days on Market
Condo for Sale
$245,000
2 bd · 2 ba · 1,295 sqft
2383 SUN VALLEY CIRCLE # 2383, WINTER PARK, FL 32792
33 Days on Market
Condo for Sale
$244,900
2 bd · 2 ba · 1,026 sqft
1500 GAY ROAD # 3C, WINTER PARK, FL 32789
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Live MLS inventory in Winter Park, updated continuously. Florida Lux Real Estate currently tracks 73 active listings here. MLS inventory updated October 17, 2026.
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