Winter Park Homes for Sale Under $300K
Homes, condos and townhomes listed at $300,000 or less.
- For sale now
- 72
- Median list price
- $217K
- Median $ / sq ft
- $187
- Median days listed
- 93
Newest 24 of 72 homes under $300k 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
$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
$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
$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
$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
$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
$175,000
7327 Forest Hill Ct #223
Winter Park, FL 32792
2 bd · 3 ba · 1,031 sqft
Hidden Oaks Condo Ph 12
MLS ID #O6403841, M L VAZ REALTY INC.
Listing provided by Stellar MLS
$169,999
3027 Aaron Bur Ave #L1
Winter Park, FL 32792
2 bd · 3 ba · 1,090 sqft
Colonies
MLS ID #TB8562681, HOMESMART.
Listing provided by Stellar MLS
$182,900
205 Lewfield Cir #205
Winter Park, FL 32792
2 bd · 2 ba · 927 sqft
Stratford A Winter Park Condo
MLS ID #S5141588, LPT REALTY, LLC.
Listing provided by Stellar MLS
$299,000
311 E Morse Blvd #7-5
Winter Park, FL 32789
1 bd · 1 ba · 482 sqft
Phillips Circle Rep
MLS ID #O6308664, CHARLES RUTENBERG REALTY ORLANDO.
Listing provided by Stellar MLS
$129,000
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
$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
$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
$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
$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
$159,900
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
$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
$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
Search all Winter Park listings on the map →
Neighborhoods with the most homes under $300k for sale
- Cedarwood8 listed
- Hidden Oaks Condo7 listed
- Golfside Villas Condo5 listed
- Colonies4 listed
- Stratford A Winter Park Condo4 listed
- Wrenwood Condo4 listed
- Parkview3 listed
- Lakeside Manor Apts Condo3 listed
- Lake Killarney Condo3 listed
- Chateaux Du Lac2 listed
Winter Park homes under $300k: quick answers
How many homes under $300k are for sale in Winter Park?+
72 homes under $300k are listed for sale in Winter Park, FL right now, 1 of them new in the last 7 days. Homes, condos and townhomes listed at $300,000 or less.
What do homes under $300k cost in Winter Park?+
The median list price is $217K (about $187 per square foot), with listings from $90K to $300K.
How long do homes under $300k in Winter Park stay on the market?+
The listings for sale now have been on the market a median of 93 days.
Which Winter Park neighborhoods have the most homes under $300k for sale?+
Cedarwood (8), Hidden Oaks Condo (7), Golfside Villas Condo (5), Colonies (4), Stratford A Winter Park Condo (4).
More Winter Park homes for sale
Homes Under $300K 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