Winter Park East Homes Under $500K for Sale
Every home priced under $500K currently for sale in Winter Park East — pulled live from the Stellar MLS and updated continuously. Pair this with the free Winter Park East market report to see what's actually selling, days on market, and sold-to-list ratios before you make an offer.
24+ Homes Under $500K in the Winter Park East area
$449,000
2703 Tierra Cir
Winter Park, FL 32792
3 bd · 2 ba · 1,737 sqft
Casa Aloma
MLS ID #O6427460, EXP REALTY LLC.
Listing provided by Stellar MLS
$220,000
4786 Tangerine Ave #4786
Winter Park, FL 32792
2 bd · 2 ba · 1,281 sqft
Wrenwood Condo
MLS ID #S5159925, EXP REALTY LLC.
Listing provided by Stellar MLS
$134,998
3032 Antique Oaks Cir #145
Winter Park, FL 32792
1 bd · 1 ba · 749 sqft
Parkview Village Condominium
MLS ID #O6446981, OLDE TOWN BROKERS INC.
Listing provided by Stellar MLS
$385,000
7384 Grand Ave
Winter Park, FL 32792
3 bd · 2 ba · 1,162 sqft
Oakcrest-516
MLS ID #O6433455, KELLER WILLIAMS WINTER PARK.
Listing provided by Stellar MLS
$268,000
5184 Lazy Oaks Dr
Winter Park, FL 32792
2 bd · 2 ba · 1,008 sqft
Lazy Oaks Condo
MLS ID #O6422366, PAINE-ANDERSON PROPERTIES, INC.
Listing provided by Stellar MLS
$246,400
193 Lewfield Cir
Winter Park, FL 32792
2 bd · 3 ba · 1,300 sqft
Stratford A Winter Park Condo
MLS ID #O6409075, COLDWELL BANKER REALTY.
Listing provided by Stellar MLS
$419,000
501 Heritage Blvd
Winter Park, FL 32792
4 bd · 2 ba · 1,376 sqft
Georgetown Estates
MLS ID #S5145746, EXP REALTY LLC.
Listing provided by Stellar MLS
$374,900
1840 Aster Dr
Winter Park, FL 32792
3 bd · 2 ba · 1,666 sqft
Garden Lake Estates Unit 1
MLS ID #O6412364, KONA REALTY SERVICES LLC.
Listing provided by Stellar MLS
$279,999
2275 Island Run
Winter Park, FL 32792
3 bd · 2 ba · 1,467 sqft
Windward Square Sec 3
MLS ID #O6439848, U KEY REALTY.
Listing provided by Stellar MLS
$325,000
2535 Leeward Way
Winter Park, FL 32792
3 bd · 2 ba · 1,783 sqft
Windward Square Sec 2
MLS ID #O6454266, CHARLES RUTENBERG REALTY ORLANDO.
Listing provided by Stellar MLS
$365,000
2168 Ridge Dr
Winter Park, FL 32792
3 bd · 2 ba · 1,208 sqft
Ridge High 1st Add
MLS ID #O6453370, CHARLES RUTENBERG REALTY ORLANDO.
Listing provided by Stellar MLS
$470,000
2008 Houndslake Drive
Winter Park, FL 32792
4 bd · 2 ba · 2,250 sqft
MLS ID #1080063, Mark Spain Real Estate.
Listing provided by Space Coast MLS (Space Coast Association of REALTORS®)
$470,000
2008 Houndslake Dr
Winter Park, FL 32792
4 bd · 2 ba · 2,250 sqft
Cedar Ridge
MLS ID #O6414369, MARK SPAIN REAL ESTATE.
Listing provided by Stellar MLS
$225,000
3462 Seagrape Dr
Winter Park, FL 32792
3 bd · 1 ba · 1,227 sqft
Eastbrook Sub
MLS ID #O6453385, KELLER WILLIAMS REALTY AT THE PARKS.
Listing provided by Stellar MLS
$385,000
7361 Grand Ave
Winter Park, FL 32792
3 bd · 2 ba · 1,305 sqft
Oakcrest-516
MLS ID #O6453291, COMPASS FLORIDA LLC.
Listing provided by Stellar MLS
$450,000
1825 Chilean Ln
Winter Park, FL 32792
5 bd · 3 ba · 1,636 sqft
Eastbrook Sub Unit 05
MLS ID #O6452415, KELLER WILLIAMS WINTER PARK.
Listing provided by Stellar MLS
$410,000
1021 Princess Gate Blvd
Winter Park, FL 32792
3 bd · 2 ba · 1,318 sqft
Howell Estates Rep
MLS ID #O6451435, BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY.
Listing provided by Stellar MLS
$482,000
1407 Broad Wing Ln
Winter Park, FL 32792
3 bd · 3 ba · 2,308 sqft
Enclave At Hawks Crest
MLS ID #O6448996, R MICHAELS REALTY LLC.
Listing provided by Stellar MLS
$97,000
1000 S Semoran Blvd #302
Winter Park, FL 32792
1 bd · 1 ba · 796 sqft
Golfside Villas Condo
MLS ID #O6428713, KELLER WILLIAMS ADVANTAGE III.
Listing provided by Stellar MLS
$249,000
4940 Tangerine Ave #4940
Winter Park, FL 32792
3 bd · 2 ba · 1,345 sqft
Wrenwood Condo
MLS ID #O6450304, COLDWELL BANKER REALTY.
Listing provided by Stellar MLS
$410,000
1935 Azalea Ave
Winter Park, FL 32792
3 bd · 2 ba · 1,300 sqft
Temple Terrace Annex
MLS ID #O6453931, C BRENNER INC.
Listing provided by Stellar MLS
$469,900
1660 Gladiolas Dr
Winter Park, FL 32792
3 bd · 2 ba · 2,047 sqft
Garden Lake Estates Unit 1
MLS ID #TB8539207, FLAT FEE MLS REALTY.
Listing provided by Stellar MLS
$280,000
2352 Sun Valley Cir
Winter Park, FL 32792
2 bd · 2 ba · 1,495 sqft
Cedarwood Village 1
MLS ID #O6441394, KELLER WILLIAMS CLASSIC.
Listing provided by Stellar MLS
$175,000
200 St Andrews Blvd #906
Winter Park, FL 32792
1 bd · 1 ba · 727 sqft
Four Seasons Condo
MLS ID #O6453614, COLDWELL BANKER REALTY.
Listing provided by Stellar MLS
More Winter Park East Homes for Sale
Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Based on information submitted to the MLS GRID as of November 3, 2026 at 7:51 PM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
All or a portion of the multiple listing information is provided by Stellar MLS, from a copyrighted compilation of listings. The compilation of listings and each individual listing are © 2026 Stellar MLS. All rights reserved.
Brevard County listings courtesy of the Space Coast Association of REALTORS® (Space Coast MLS)
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed accurate by the MLS.
© 2026 Space Coast Association of REALTORS®. All information should be independently reviewed and verified for accuracy.
Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA