Winter Park Pines Homes Under $500K for Sale
Every home priced under $500K currently for sale in Winter Park Pines — pulled live from the Stellar MLS and updated continuously. Pair this with the free Winter Park Pines 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 Winter Park Pines
$299,000
170 Balfour Dr #1
Winter Park, FL 32792
2 bd · 2 ba · 1,032 sqft
Winter Park Pointe 01
MLS ID #O6446433, RE/MAX ASSURED.
Listing provided by Stellar MLS
$379,999
2017 Canny Cv
Winter Park, FL 32792
3 bd · 3 ba · 1,907 sqft
Grayson Square
MLS ID #O6430136, KELLER WILLIAMS WINTER PARK.
Listing provided by Stellar MLS
$475,000
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
$475,000
2008 Houndslake Drive, Winter Park, Fl 32792
Winter Park, FL 32792
4 bd · 2 ba · 2,250 sqft
None
MLS ID #1080063, Mark Spain Real Estate.
Listing provided by Space Coast MLS (Space Coast Association of REALTORS®)
$384,900
1840 Aster Dr
Winter Park, FL 32792
3 bd · 2 ba · 1,667 sqft
Garden Lake Estates Unit 1
MLS ID #O6412364, KONA REALTY SERVICES LLC.
Listing provided by Stellar MLS
$464,000
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
$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
$380,000
4870 Seminole Ave
Winter Park, FL 32792
3 bd · 2 ba · 1,277 sqft
Suburban Homes First Add
MLS ID #O6441887, COLDWELL BANKER REALTY.
Listing provided by Stellar MLS
$247,000
2477 Tahoe Cir #2477
Winter Park, FL 32792
2 bd · 2 ba · 1,316 sqft
Cedarwood Village
MLS ID #O6432904, RE/MAX TOWN & COUNTRY REALTY.
Listing provided by Stellar MLS
$388,000
1092 Eastbrook Blvd
Winter Park, FL 32792
3 bd · 2 ba · 1,122 sqft
Eastbrook Sub
MLS ID #O6407251, JC FLORIDA REALTY LLC.
Listing provided by Stellar MLS
$440,000
2301 Conifer Ave
Winter Park, FL 32792
4 bd · 2 ba · 2,189 sqft
Eastbrook Sub Unit 16
MLS ID #O6440609, LOKATION.
Listing provided by Stellar MLS
$439,900
3150 Shady Pine Ave
Winter Park, FL 32792
4 bd · 2 ba · 1,624 sqft
Bel Aire
MLS ID #O6445202, WATSON REALTY CORP.
Listing provided by Stellar MLS
$230,000
2712 Tortoise Cv
Winter Park, FL 32792
2 bd · 1 ba · 924 sqft
Slovak Village
MLS ID #O6419150, CHARLES RUTENBERG REALTY ORLANDO.
Listing provided by Stellar MLS
$399,999
1401 Aster Ct
Winter Park, FL 32792
4 bd · 2 ba · 1,653 sqft
Garden Lake Estates Unit 3
MLS ID #O6425103, SPARROW REALTY & RENTALS.
Listing provided by Stellar MLS
$349,000
7605 Aloma Pines Ct
Winter Park, FL 32792
3 bd · 3 ba · 1,872 sqft
Aloma Trails
MLS ID #O6435026, USCO CAPITAL GROUP.
Listing provided by Stellar MLS
$365,000
7560 Aloma Pines Ct
Winter Park, FL 32792
3 bd · 3 ba · 1,866 sqft
Aloma Trails
MLS ID #O6439431, KELLER WILLIAMS ADVANTAGE III.
Listing provided by Stellar MLS
$364,900
7498 Aloma Pines Ct
Winter Park, FL 32792
3 bd · 3 ba · 1,872 sqft
Aloma Trails
MLS ID #O6445209, KELLER WILLIAMS REALTY AT THE PARKS.
Listing provided by Stellar MLS
$170,000
7450 Wynnewood Sq #189
Winter Park, FL 32792
2 bd · 3 ba · 1,031 sqft
Hidden Oaks Condo Ph 10
MLS ID #O6425486, REAL ESTATE PROFESSIONALS SE.
Listing provided by Stellar MLS
$430,000
3740 Hawthorne Ln
Winter Park, FL 32792
3 bd · 2 ba · 1,645 sqft
Garden Lake Estates Unit 1
MLS ID #O6428202, FLORIDA REALTY INVESTMENTS.
Listing provided by Stellar MLS
$295,000
2302 Barbados Dr
Winter Park, FL 32792
2 bd · 2 ba · 1,544 sqft
Windward Square Sec 3
MLS ID #O6440892, KELLER WILLIAMS REALTY AT THE PARKS.
Listing provided by Stellar MLS
$469,900
1320 Gladiolas Dr
Winter Park, FL 32792
4 bd · 2 ba · 1,624 sqft
Garden Lake Estates Unit 3
MLS ID #O6412139, OPTIMA REAL ESTATE.
Listing provided by Stellar MLS
$159,000
200 Saint Andrews Blvd #704
Winter Park, FL 32792
1 bd · 1 ba · 793 sqft
Four Seasons Condo
MLS ID #O6445691, EXP REALTY LLC.
Listing provided by Stellar MLS
$249,000
2463 Grand Teton Cir #2463
Winter Park, FL 32792
3 bd · 3 ba · 1,720 sqft
Cedarwood Village 1
MLS ID #O6443154, MAINFRAME REAL ESTATE.
Listing provided by Stellar MLS
$410,500
7786 Fox Knoll Pl
Winter Park, FL 32792
4 bd · 2 ba · 1,301 sqft
Bridgewater
MLS ID #O6445061, NIZZ REALTY INC.
Listing provided by Stellar MLS
More Winter Park Pines 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 October 2, 2026 at 4:48 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.
© 2026Space 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