Winter Park Homes Under $500K for Sale
Every home priced under $500K currently for sale in Winter Park — pulled live from the Stellar MLS and updated continuously. Pair this with the free Winter Park 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 area
$499,900
351 Starling Rd
Winter Park, FL 32789
3 bd · 2 ba · 1,979 sqft
Flamingo Shores
MLS ID #O6429698, HOUWZER INC.
Listing provided by Stellar MLS
$255,000
1500 Gay Rd #26-C
Winter Park, FL 32789
2 bd · 2 ba · 1,026 sqft
Chateaux Du Lac
MLS ID #O6448226, SOTERA LIVING.
Listing provided by Stellar MLS
$279,000
283 Sandlewood Trl #3
Winter Park, FL 32789
2 bd · 3 ba · 960 sqft
Sandlewood Creek Phase 2
MLS ID #O6431475, RE/MAX INNOVATION.
Listing provided by Stellar MLS
$450,000
239 Orange Terrace Dr
Winter Park, FL 32789
4 bd · 3 ba · 1,866 sqft
Orange Terrace
MLS ID #O6445496, CREEGAN GROUP.
Listing provided by Stellar MLS
$305,000
2640 Beverly Ave
Winter Park, FL 32789
3 bd · 1 ba · 1,216 sqft
Killarney Circle
MLS ID #TB8559088, REAL BROKER, LLC.
Listing provided by Stellar MLS
$245,000
1250 S Denning Dr #127
Winter Park, FL 32789
2 bd · 2 ba · 908 sqft
Mead Garden
MLS ID #O6439854, PREMIER SOTHEBY'S INTL. REALTY.
Listing provided by Stellar MLS
$490,900
525 Ololu Dr
Winter Park, FL 32789
3 bd · 3 ba · 1,786 sqft
Killarney Circle
MLS ID #S5148431, CAISSA REALTY INVESTMENT INC.
Listing provided by Stellar MLS
$494,999
981 Aragon Ave
Winter Park, FL 32789
2 bd · 1 ba · 857 sqft
Seville Park
MLS ID #O6420093, COLDWELL BANKER REALTY.
Listing provided by Stellar MLS
$320,000
148 Oak Grove Rd
Winter Park, FL 32789
3 bd · 2 ba · 1,156 sqft
Winter Park Oaks
MLS ID #O6450470, CENTRAL FLORIDA REALTY EXPERTS.
Listing provided by Stellar MLS
$99,900
1695 Lee Rd #D211
Winter Park, FL 32789
2 bd · 1 ba · 881 sqft
Waterfall Cove/Winter Park
MLS ID #O6396190, LOKATION.
Listing provided by Stellar MLS
$424,900
712 Baffie Ave
Winter Park, FL 32789
3 bd · 1 ba · 1,304 sqft
Dubsdread Heights
MLS ID #O6445837, RP INVESTMENT REALTY LLC.
Listing provided by Stellar MLS
$349,000
1306 S Pennsylvania Ave #5
Winter Park, FL 32789
2 bd · 1 ba · 830 sqft
Virginia Heights Condo
MLS ID #O6443013, KELLER WILLIAMS WINTER PARK.
Listing provided by Stellar MLS
$350,000
310 Granada Dr
Winter Park, FL 32789
3 bd · 2 ba · 1,344 sqft
Fairview Heights Rep
MLS ID #O6447315, COLDWELL BANKER REALTY.
Listing provided by Stellar MLS
$242,500
1250 S Denning Dr #Unit 233
Winter Park, FL 32789
2 bd · 2 ba · 913 sqft
Mead Garden Condominium
MLS ID #O6430611, STOCKWORTH REALTY GROUP.
Listing provided by Stellar MLS
$405,000
1955 Eland Ave
Winter Park, FL 32789
3 bd · 2 ba · 1,494 sqft
Lake Bell Terrace
MLS ID #O6433345, REAL PROPERTY MANAGEMENT AND REALTY.
Listing provided by Stellar MLS
$320,000
811 Overspin Dr
Winter Park, FL 32789
2 bd · 1 ba · 749 sqft
Dubsdread Heights
MLS ID #O6400009, RICK SINGH REAL ESTATE.
Listing provided by Stellar MLS
$290,000
188 Sandlewood #1
Winter Park, FL 32789
2 bd · 3 ba · 1,133 sqft
Sandlewood Creek Condo
MLS ID #O6445407, NOELKE REALTY.
Listing provided by Stellar MLS
$449,000
1652 Berkshire Ave
Winter Park, FL 32789
3 bd · 2 ba · 1,498 sqft
Orwin Manor Westminster Sec
MLS ID #O6432617, COLDWELL BANKER REALTY.
Listing provided by Stellar MLS
$459,900
630 Killarney Bay Ct #3
Winter Park, FL 32789
2 bd · 3 ba · 1,428 sqft
Killarney Bay Condo
MLS ID #O6375307, FLORIDA ONE REAL ESTATE LLC.
Listing provided by Stellar MLS
$469,000
2183 Crandon Ave
Winter Park, FL 32789
4 bd · 2 ba · 1,200 sqft
Olympia Heights Annex
MLS ID #O6433521, REAL PROPERTY MANAGEMENT AND REALTY.
Listing provided by Stellar MLS
$354,000
700 Melrose Ave #M23
Winter Park, FL 32789
2 bd · 2 ba · 1,074 sqft
Winter Park Gardens Condo
MLS ID #O6447242, COMPASS FLORIDA LLC.
Listing provided by Stellar MLS
$265,000
1250 S Denning Dr #119
Winter Park, FL 32789
2 bd · 2 ba · 908 sqft
Mead Garden
MLS ID #O6444618, FANNIE HILLMAN & ASSOCIATES.
Listing provided by Stellar MLS
$479,900
1660 Orange Ave
Winter Park, FL 32789
3 bd · 2 ba · 1,614 sqft
Orwin Manor Westminster Sec
MLS ID #L4965340, EXP REALTY LLC.
Listing provided by Stellar MLS
$169,900
2500 Lee Rd #123
Winter Park, FL 32789
1 bd · 1 ba · 645 sqft
Lakeside Manor Apts Condo
MLS ID #O6445068, HOME WISE REALTY GROUP, INC..
Listing provided by Stellar MLS
More Winter Park Homes for Sale
All Winter Park homes $500K and up, with the live market brief →
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 October 21, 2026 at 9:03 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.
Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA