Kenilworth Shores Homes Under $500K for Sale
Every home priced under $500K currently for sale in Kenilworth Shores — pulled live from the Stellar MLS and updated continuously. Pair this with the free Kenilworth Shores 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 Kenilworth Shores
$359,000
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
$285,000
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
$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
$475,000
1211 Schultz Ave
Winter Park, FL 32789
3 bd · 2 ba · 1,085 sqft
Metzingers Add
MLS ID #O6442460, KELLER WILLIAMS WINTER PARK.
Listing provided by Stellar MLS
$130,000
2500 Lee Rd #143
Winter Park, FL 32789
1 bd · 1 ba · 645 sqft
Lakeside Manor Apts Condo
MLS ID #O6438724, PALMANO GROUP RE BROKERAGE LLC.
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
$279,000
311 E Morse Blvd #7-11
Winter Park, FL 32789
1 bd · 1 ba · 570 sqft
Phillips Circle Rep
MLS ID #O6337061, FANNIE HILLMAN & ASSOCIATES.
Listing provided by Stellar MLS
$329,000
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
$448,000
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
$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
$102,500
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
$164,500
1500 Gay Rd #4d
Winter Park, FL 32789
1 bd · 1 ba · 732 sqft
Chateaux Du Lac
MLS ID #O6425078, REALCOM REAL ESTATE SERVICES INC.
Listing provided by Stellar MLS
$439,000
950 Hanover Ave
Winter Park, FL 32789
3 bd · 2 ba · 1,606 sqft
Albert Lee Ridge 1st Add
MLS ID #O6398273, 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
$269,000
151 N Orlando Ave #242
Winter Park, FL 32789
2 bd · 1 ba · 710 sqft
Lake Killarney Condo
MLS ID #O6437574, COLONIALTOWN REALTY.
Listing provided by Stellar MLS
$140,000
1695 Lee Rd #C206
Winter Park, FL 32789
2 bd · 1 ba · 881 sqft
Waterfall Cove
MLS ID #TB8551269, INVESTMENT 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
$350,000
700 Melrose Ave #J24
Winter Park, FL 32789
1 bd · 1 ba · 987 sqft
Winter Park Gardens Condo
MLS ID #R4911307, KIMBRIDGE REALTY, LLC.
Listing provided by Stellar MLS
$242,400
2500 Lee Rd #104
Winter Park, FL 32789
2 bd · 2 ba · 956 sqft
Lakeside Manor Apts Condo
MLS ID #TB8517242, FLAT FEE MLS REALTY.
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
$210,000
669 W Comstock Ave
Winter Park, FL 32789
0.05 acres
Winter Park
MLS ID #TB8535201, HOMECOIN.COM.
Listing provided by Stellar MLS
$449,900
259 Orange Terrace Drive
Winter Park, FL 32789
3 bd · 2 ba · 1,248 sqft
Orange Terrace
MLS ID #O6419225, PREMIER SOTHEBY'S INTL. REALTY.
Listing provided by Stellar MLS
$489,000
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
$450,000
786 W Canton Ave
Winter Park, FL 32789
0.11 acres
Capens Add
MLS ID #O6441522, CHARLES RUTENBERG REALTY ORLANDO.
Listing provided by Stellar MLS
More Kenilworth Shores 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 10:55 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