143 listings

Homes Under $500K for Sale in Winter Park, FL

Explore 143 homes under $500K in Winter Park, Florida. Updated every 15 minutes from Stellar MLS.

$304KAvg Price
$80KMin Price
$499KMax Price
14With Pool
3Waterfront

Browse Homes Under $500K for Sale in Winter Park, FL. 143 homes currently listed, updated daily from Stellar MLS.

2217 SUSSEX RD
$499K
2217 SUSSEX RD, Winter Park
4 bd 2 ba 2,092 sqft
228 days on market
1807 HAMMERLIN AVE #G
$499K
1807 HAMMERLIN AVE #G, Winter Park
3 bd 3 ba 1,818 sqft
131 days on market
230 STRATHY LN
$499K
230 STRATHY LN, Winter Park
0 ba 920 sqft
New listing
2231 NAIRN DR
$499K
2231 NAIRN DR, Winter Park
0 ba 1,088 sqft
New listing
525 OLOLU DR
$496K
525 OLOLU DR, Winter Park
3 bd 3 ba 1,786 sqft
73 days on market
2715 PRINCE JOHN RD
$495K
2715 PRINCE JOHN RD, Winter Park
3 bd 2 ba 1,565 sqft
43 days on market
2008 HOUNDSLAKE DR
$490K
2008 HOUNDSLAKE DR, Winter Park
4 bd 2 ba 2,250 sqft
35 days on market
630 KILLARNEY BAY CT #3
$475K
630 KILLARNEY BAY CT #3, Winter Park
2 bd 3 ba 1,428 sqft
128 days on market
346 S RANGER BLVD
$475K
346 S RANGER BLVD, Winter Park
3 bd 2 ba 1,592 sqft
296 days on market
1320 GLADIOLAS DR
$475K
1320 GLADIOLAS DR, Winter Park
4 bd 2 ba 1,624 sqft
51 days on market
3641 HAWTHORNE LN
$475K
3641 HAWTHORNE LN, Winter Park
3 bd 2 ba 1,622 sqft
23 days on market
644 N KNOWLES AVE #3
$475K
644 N KNOWLES AVE #3, Winter Park
1 bd 1 ba 767 sqft
10 days on market
2041 JEWELL AVE
$470K
2041 JEWELL AVE, Winter Park
3 bd 1 ba 1,508 sqft
9 days on market
2703 TIERRA CIR
$469K
2703 TIERRA CIR, Winter Park
3 bd 2 ba 1,737 sqft
1 days on market
1052 MANCHESTER CIR
$460K
1052 MANCHESTER CIR, Winter Park
3 bd 2 ba 1,703 sqft
134 days on market
950 HANOVER AVE
$460K
950 HANOVER AVE, Winter Park
3 bd 2 ba 1,606 sqft
106 days on market
5331 OAK CT
$460K
5331 OAK CT, Winter Park
3 bd 2 ba 1,263 sqft
139 days on market
3601 MIDIRON DR
$460K
3601 MIDIRON DR, Winter Park
0 ba
189 days on market
259 ORANGE TERRACE DRIVE
$460K
259 ORANGE TERRACE DRIVE, Winter Park
3 bd 2 ba 1,248 sqft
27 days on market
5340 N LAKE BURKETT LN
$459K
5340 N LAKE BURKETT LN, Winter Park
3 bd 2 ba 1,746 sqft
45 days on market
501 HERITAGE BLVD
$458K
501 HERITAGE BLVD, Winter Park
4 bd 2 ba 1,376 sqft
128 days on market
316 BECKETT CT
$450K
316 BECKETT CT, Winter Park
4 bd 2 ba 1,651 sqft
54 days on market
1564 LAWNDALE CIR
$450K
1564 LAWNDALE CIR, Winter Park
4 bd 3 ba 1,980 sqft
21 days on market
JESSICA CT
$449K
JESSICA CT, Winter Park
0 ba
10 days on market