Winter Park Homes for Sale Under $400K
Homes, condos and townhomes listed at $400,000 or less.
- For sale now
- 106
- Median list price
- $268K
- Median $ / sq ft
- $200
- Median days listed
- 82
Newest 24 of 106 homes under $400k in Winter Park
$299,900
2821 Riddle Dr
Winter Park, FL 32789
4 bd · 4 ba · 2,445 sqft
Fairbanks Shores First Add
MLS ID #O6457113, ORLANDO REGIONAL REALTY.
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
$395,000
5409 Albert Dr
Winter Park, FL 32792
3 bd · 2 ba · 1,483 sqft
Howell Branch Woods
MLS ID #C7528794, SOVEREIGN REAL ESTATE GROUP.
Listing provided by Stellar MLS
$369,900
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
$375,000
1830 Gladiolas Dr
Winter Park, FL 32792
3 bd · 2 ba · 1,674 sqft
Garden Lake Estates Unit 1
MLS ID #O6452778, REAL PROPERTY MANAGEMENT AND REALTY.
Listing provided by Stellar MLS
$394,900
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
$310,000
700 Melrose Ave #A22
Winter Park, FL 32789
2 bd · 2 ba · 1,074 sqft
Winter Park Gardens Condo
MLS ID #S5160491, CENTURY 21 CARIOTI.
Listing provided by Stellar MLS
$235,000
1500 Gay Rd #3c
Winter Park, FL 32789
2 bd · 2 ba · 1,026 sqft
Chateaux Du Lac
MLS ID #O6417533, FANNIE HILLMAN & ASSOCIATES.
Listing provided by Stellar MLS
$369,000
2531 Passamonte Dr #4h
Winter Park, FL 32792
3 bd · 3 ba · 1,790 sqft
Via Lago/Hanging Moss Ph 09
MLS ID #O6452859, REDFIN CORPORATION.
Listing provided by Stellar MLS
$295,000
700 Melrose Ave #B23
Winter Park, FL 32789
2 bd · 2 ba · 1,074 sqft
Winter Park Gardens Condo
MLS ID #O6455185, FANNIE HILLMAN & ASSOCIATES.
Listing provided by Stellar MLS
$108,900
311 Scottsdale Sq #311
Winter Park, FL 32792
1 bd · 1 ba · 785 sqft
Winter Park Woods Condo
MLS ID #O6355536, EMPIRE NETWORK REALTY.
Listing provided by Stellar MLS
$268,000
2475 Tahoe Cir
Winter Park, FL 32792
2 bd · 2 ba · 1,295 sqft
Cedarwood Village 1
MLS ID #O6428082, COLDWELL BANKER REALTY.
Listing provided by Stellar MLS
$289,000
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
$399,500
2038 Ponderosa Ave
Winter Park, FL 32792
3 bd · 2 ba · 1,360 sqft
Eastbrook Sub Unit 8
MLS ID #O6453339, KELLER WILLIAMS REALTY AT THE PARKS.
Listing provided by Stellar MLS
$189,900
623 Grenadine Ct #623
Winter Park, FL 32792
2 bd · 2 ba · 1,037 sqft
Winter Park Villas Condo
MLS ID #O6434195, COLDWELL BANKER REALTY.
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
$365,000
7506 Cranes Creek Ct #30
Winter Park, FL 32792
3 bd · 3 ba · 1,861 sqft
Cranes Creek
MLS ID #S5156844, TRANSCONTINENTAL REALTY GROUP,.
Listing provided by Stellar MLS
$399,900
603 Carnation Dr
Winter Park, FL 32792
4 bd · 2 ba · 1,427 sqft
Eastbrook Sub
MLS ID #TB8561386, A-WARD WINNING REALTY LLC.
Listing provided by Stellar MLS
$399,900
5503 Albert Dr
Winter Park, FL 32792
3 bd · 2 ba · 1,366 sqft
Howell Branch Woods
MLS ID #S5151098, AXEN REALTY, LLC.
Listing provided by Stellar MLS
$369,999
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
$139,998
3019 Antique Oaks Cir #127
Winter Park, FL 32792
1 bd · 1 ba · 749 sqft
Parkview Village
MLS ID #O6455101, CHEVON EATON.
Listing provided by Stellar MLS
$399,000
2176 Crandon Ave
Winter Park, FL 32789
2 bd · 1 ba · 959 sqft
Olympia Heights Annex
MLS ID #O6455726, CORCORAN PREMIER REALTY.
Listing provided by Stellar MLS
$319,000
192 Balfour Dr #2
Winter Park, FL 32792
2 bd · 2 ba · 1,287 sqft
Winter Park Pointe 02 Ph 01
MLS ID #O6443731, BHHS FLORIDA REALTY.
Listing provided by Stellar MLS
$270,000
7463 Canford Ct #15
Winter Park, FL 32792
3 bd · 3 ba · 1,580 sqft
Whisperwood Condo
MLS ID #O6452947, EXP REALTY LLC.
Listing provided by Stellar MLS
Search all Winter Park listings on the map →
Winter Park homes under $400k by price
- Under $300K72
- $300K–$500K34
Neighborhoods with the most homes under $400k for sale
- Cedarwood8 listed
- Hidden Oaks Condo7 listed
- Golfside Villas Condo5 listed
- Grayson Square4 listed
- Colonies4 listed
- Stratford A Winter Park Condo4 listed
- Wrenwood Condo4 listed
- Winter Park Gardens Condo3 listed
- Eastbrook Sub3 listed
- Parkview3 listed
Winter Park homes under $400k: quick answers
How many homes under $400k are for sale in Winter Park?+
106 homes under $400k are listed for sale in Winter Park, FL right now, 2 of them new in the last 7 days. Homes, condos and townhomes listed at $400,000 or less.
What do homes under $400k cost in Winter Park?+
The median list price is $268K (about $200 per square foot), with listings from $90K to $400K.
How long do homes under $400k in Winter Park stay on the market?+
The listings for sale now have been on the market a median of 82 days.
Which Winter Park neighborhoods have the most homes under $400k for sale?+
Cedarwood (8), Hidden Oaks Condo (7), Golfside Villas Condo (5), Grayson Square (4), Colonies (4).
More Winter Park homes for sale
Homes Under $400K in other cities
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 13, 2026 at 11:51 AM 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