Windsor Hills Homes Under $500K for Sale
Every home priced under $500K currently for sale in Windsor Hills — pulled live from the Stellar MLS and updated continuously. Pair this with the free Windsor Hills market report to see what's actually selling, days on market, and sold-to-list ratios before you make an offer.
13 Homes Under $500K in Windsor Hills
$470,000
2579 Maneshaw Ln
Kissimmee, FL 34747
3 bd · 3 ba · 1,440 sqft
Windsor Hills Ph 4
MLS ID #S5160651, REAL BROKER, LLC.
Listing provided by Stellar MLS
$395,000
7683 Fitzclarence St
Kissimmee, FL 34747
3 bd · 3 ba · 1,440 sqft
Windsor Hills Ph 02
MLS ID #O6421663, KRESSLER REAL ESTATE.
Listing provided by Stellar MLS
$409,000
2545 Renshaw St
Kissimmee, FL 34747
3 bd · 3 ba · 1,440 sqft
Windsor Hills Ph 2
MLS ID #O6404535, EXP REALTY LLC.
Listing provided by Stellar MLS
$270,000
2788 Almaton Loop #102
Kissimmee, FL 34747
2 bd · 2 ba · 1,081 sqft
Windsor Hills
MLS ID #G5119347, LPT REALTY, LLC.
Listing provided by Stellar MLS
$399,000
7681 Sir Kaufmann Ct
Kissimmee, FL 34747
3 bd · 3 ba · 1,440 sqft
Windsor Hills Ph 4
MLS ID #O6371332, STOCKWORTH REALTY GROUP.
Listing provided by Stellar MLS
$389,999
7650 Comrow St #105
Kissimmee, FL 34747
3 bd · 2 ba · 1,410 sqft
Windsor Hills, Ventura At Windsor Hills
MLS ID #S5157519, TEAM DONOVAN.
Listing provided by Stellar MLS
$339,950
2821 Almaton Loop #203
Kissimmee, FL 34747
3 bd · 2 ba · 1,246 sqft
Windsor Hills, Ventura At Windsor Hills
MLS ID #S5147977, TEAM DONOVAN.
Listing provided by Stellar MLS
$380,000
7663 Sir Kaufmann Ct
Kissimmee, FL 34747
3 bd · 3 ba · 1,440 sqft
Windsor Hills Ph 4
MLS ID #O6353629, BLUE LIGHTHOUSE REALTY INC.
Listing provided by Stellar MLS
$419,000
2592 Maneshaw Ln
Kissimmee, FL 34747
3 bd · 3 ba · 1,440 sqft
Windsor Hills Ph 2
MLS ID #O6442328, LA ROSA REALTY LLC.
Listing provided by Stellar MLS
$394,000
7654 Otterspool St
Kissimmee, FL 34747
3 bd · 3 ba · 1,440 sqft
Windsor Hills Ph 2
MLS ID #O6417354, LA ROSA REALTY LLC.
Listing provided by Stellar MLS
$425,000
7674 Otterspool St
Kissimmee, FL 34747
3 bd · 3 ba · 1,440 sqft
Windsor Hills Ph 2
MLS ID #O6413246, LA ROSA REALTY LLC.
Listing provided by Stellar MLS
$289,950
7671 Comrow St #202
Kissimmee, FL 34747
2 bd · 2 ba · 1,081 sqft
Windsor Hills, Ventura At Windsor Hills
MLS ID #S5111171, TEAM DONOVAN.
Listing provided by Stellar MLS
$275,000
2788 Almaton Loop #202
Kissimmee, FL 34747
2 bd · 2 ba · 1,081 sqft
Windsor Hills P1
MLS ID #S5151029, IMAGINATION REALTY, INC.
Listing provided by Stellar MLS
More Windsor Hills 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 6:48 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