Winter Springs Homes Under $500K for Sale
Every home priced under $500K currently for sale in Winter Springs — pulled live from the Stellar MLS and updated continuously. Pair this with the free Winter Springs 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 Springs area
$361,000
733 Lakeview Dr
Winter Springs, FL 32708
3 bd · 2 ba · 1,597 sqft
Wildwood
MLS ID #O6450539, OPENDOOR BROKERAGE LLC.
Listing provided by Stellar MLS
$130,000
220 Moree Loop #1
Winter Springs, FL 32708
1 bd · 1 ba · 710 sqft
Baytree Village
MLS ID #O6438570, COLDWELL BANKER REALTY.
Listing provided by Stellar MLS
$499,999
1010 W Pebble Beach Cir
Winter Springs, FL 32708
3 bd · 3 ba · 1,732 sqft
Country Club Village Unit 1
MLS ID #O6442178, EXP REALTY LLC.
Listing provided by Stellar MLS
$234,900
611 Casa Park A Ct
Winter Springs, FL 32708
2 bd · 3 ba · 1,156 sqft
Casa Park Villas Ph 1
MLS ID #O6431044, BALDWIN PARK REALTY LLC.
Listing provided by Stellar MLS
$350,000
615 Pearl Rd
Winter Springs, FL 32708
3 bd · 2 ba · 1,784 sqft
North Orlando Ranches Sec 08
MLS ID #O6445919, RE/MAX TOWN & COUNTRY REALTY.
Listing provided by Stellar MLS
$350,000
113 Lido Rd
Winter Springs, FL 32708
4 bd · 2 ba · 1,312 sqft
North Orlando Ranches Sec 09
MLS ID #O6447866, REDFIN CORPORATION.
Listing provided by Stellar MLS
$234,000
1481 Casa Park Cir
Winter Springs, FL 32708
2 bd · 3 ba · 1,088 sqft
Casa Park Villas Ph 2
MLS ID #O6453524, CHARLES RUTENBERG REALTY ORLANDO.
Listing provided by Stellar MLS
$97,999
613 Sailfish Rd
Winter Springs, FL 32708
0.31 acres
North Orlando Ranches Sec 02a
MLS ID #A4710399, NEW ALLIANCE GROUP REALTY.
Listing provided by Stellar MLS
$500,000
161 Bear Springs Dr
Winter Springs, FL 32708
3 bd · 3 ba · 1,704 sqft
Hickory Grove Twnhms
MLS ID #O6450193, SHAHRAM SONDI + CO..
Listing provided by Stellar MLS
$259,000
122 Burgos Rd
Winter Springs, FL 32708
3 bd · 2 ba · 1,178 sqft
North Orlando 2nd Add
MLS ID #G5119422, OLYMPUS EXECUTIVE REALTY INC.
Listing provided by Stellar MLS
$420,000
963 Sequoia Dr
Winter Springs, FL 32708
3 bd · 2 ba · 1,831 sqft
Oak Forest Unit 2b
MLS ID #O6424067, OPENDOOR BROKERAGE LLC.
Listing provided by Stellar MLS
$344,000
830 Dunbar Ter
Winter Springs, FL 32708
3 bd · 3 ba · 1,792 sqft
Highlands Sec 1
MLS ID #O6418603, OPENDOOR BROKERAGE LLC.
Listing provided by Stellar MLS
$279,999
432 Tradition Ln
Winter Springs, FL 32708
2 bd · 3 ba · 1,275 sqft
Heritage Park Twnhms
MLS ID #O6453934, BEYCOME OF FLORIDA LLC.
Listing provided by Stellar MLS
$244,999
1453 Casa Park Cir
Winter Springs, FL 32708
2 bd · 2 ba · 1,156 sqft
Casa Park Villas Ph 2
MLS ID #S5153753, KELLER WILLIAMS LEGACY REALTY.
Listing provided by Stellar MLS
$412,000
1000 Troon Trce
Winter Springs, FL 32708
3 bd · 3 ba · 1,703 sqft
Greenbriar Sub Ph 1
MLS ID #O6440283, BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY.
Listing provided by Stellar MLS
$439,900
288 Ringwood Dr
Winter Springs, FL 32708
3 bd · 2 ba · 1,700 sqft
Deer Run Unit 23a
MLS ID #O6440707, KELLER WILLIAMS ADVANTAGE REALTY.
Listing provided by Stellar MLS
$459,900
1304 Ortega St
Winter Springs, FL 32708
4 bd · 3 ba · 2,152 sqft
Sunrise Estates Unit 1
MLS ID #TB8504998, HOME PRIME REALTY LLC.
Listing provided by Stellar MLS
$199,000
506 Club Dr
Winter Springs, FL 32708
2 bd · 2 ba · 1,002 sqft
Cypress Club
MLS ID #O6362326, CALL IT CLOSED INTL REALTY.
Listing provided by Stellar MLS
$445,000
1354 Tarflower Dr
Winter Springs, FL 32708
4 bd · 3 ba · 1,643 sqft
Hickory Grove Twnhms
MLS ID #O6451380, KELLER WILLIAMS ADVANTAGE III.
Listing provided by Stellar MLS
$299,990
702 Glasgow Ct
Winter Springs, FL 32708
4 bd · 3 ba · 1,878 sqft
Highland Patio Homes
MLS ID #O6451663, KELLER WILLIAMS HERITAGE REALTY.
Listing provided by Stellar MLS
$360,000
923 Torrey Pine Dr
Winter Springs, FL 32708
2 bd · 2 ba · 1,193 sqft
Greenbriar Sub Ph 2
MLS ID #O6431747, KELLER WILLIAMS ADVANTAGE REALTY.
Listing provided by Stellar MLS
$345,000
140 Bombay Ave
Winter Springs, FL 32708
3 bd · 2 ba · 1,373 sqft
North Orlando 5th Add
MLS ID #O6448262, FLORIDA REALTY OF MIAMI CORP.
Listing provided by Stellar MLS
$399,000
1436 Winter Wharf Ln
Winter Springs, FL 32708
3 bd · 4 ba · 1,932 sqft
Jesups Landing
MLS ID #O6446719, COLDWELL BANKER REALTY.
Listing provided by Stellar MLS
$235,000
604 Casa Park Court G
Winter Springs, FL 32708
2 bd · 2 ba · 1,088 sqft
Casa Park Villas Ph 1
MLS ID #O6453699, RE/MAX TOWN & COUNTRY REALTY.
Listing provided by Stellar MLS
More Winter Springs 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 4, 2026 at 10:50 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