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.
24+ Homes Under $500K in Windsor Hills
$325,000
2817 Almaton Loop #304
Kissimmee, FL 34747
3 bd · 2 ba · 1,450 sqft
Ventura At Windsor Hills Condo Ph 6
MLS ID #A4708153, SAVVY AVENUE, LLC.
Listing provided by Stellar MLS
$275,000
8809 Dunes Ct #202
Kissimmee, FL 34747
4 bd · 2 ba · 1,377 sqft
Legacy Dunes Condo
MLS ID #O6440262, HOMEVEST REALTY.
Listing provided by Stellar MLS
$475,000
7593 Gathering Dr #707
Reunion, FL 34747
2 bd · 2 ba · 1,430 sqft
Reunion Grande Condo
MLS ID #O6432930, REAL BROKER, LLC.
Listing provided by Stellar MLS
$479,000
7593 Gathering Dr #803
Reunion, FL 34747
2 bd · 2 ba · 1,646 sqft
Reunion Grande Condo
MLS ID #O6445478, REAL BROKER, LLC.
Listing provided by Stellar MLS
$419,900
414 Water St #414
Celebration, FL 34747
2 bd · 2 ba · 1,211 sqft
Water Street Condo Ph 3
MLS ID #S5157464, FLORIDA IN MOTION REALTY INC.
Listing provided by Stellar MLS
$430,000
8907 Sydney Ave
Kissimmee, FL 34747
5 bd · 5 ba · 2,263 sqft
Windsor At Westside Ph 3
MLS ID #O6434299, C23 REALTY LLC.
Listing provided by Stellar MLS
$340,000
2813 Almaton Loop #301
Kissimmee, FL 34747
3 bd · 2 ba · 1,246 sqft
Ventura At Windsor Hills Condo Ph 4
MLS ID #O6404870, C23 REALTY LLC.
Listing provided by Stellar MLS
$199,000
8810 Grand Palms Cir #B
Kissimmee, FL 34747
3 bd · 2 ba · 1,245 sqft
Grand Palms Condo 4 Ph 1
MLS ID #O6446760, HOMEVEST REALTY.
Listing provided by Stellar MLS
$454,000
8515 Palm Harbor Dr
Kissimmee, FL 34747
5 bd · 4 ba · 2,317 sqft
Emerald Island Resort Ph 5a
MLS ID #S5149105, AMERICAN IDEAL HOMES, LLC.
Listing provided by Stellar MLS
$324,990
239 Longview Ave #311
Celebration, FL 34747
1 bd · 1 ba · 952 sqft
Celebration
MLS ID #O6436720, DENIZ REALTY PARTNERS LLC.
Listing provided by Stellar MLS
$370,000
7740 Sandy Ridge Dr #215
Kissimmee, FL 34747
5 bd · 5 ba · 2,630 sqft
Spectrum At Reunion
MLS ID #TB8543178, LOKATION.
Listing provided by Stellar MLS
$499,000
2462 Dubai St
Kissimmee, FL 34747
5 bd · 4 ba · 2,492 sqft
Windsor At Westside Ph 3a
MLS ID #P4939824, KELLER WILLIAMS REALTY SMART 1.
Listing provided by Stellar MLS
$311,950
8981 Shine Dr
Kissimmee, FL 34747
4 bd · 3 ba · 1,694 sqft
West Lucaya Village
MLS ID #S5124447, LOKATION.
Listing provided by Stellar MLS
$215,000
3012 Parkway Blvd #203
Kissimmee, FL 34747
2 bd · 2 ba · 937 sqft
Blossom Park Villas A Condo
MLS ID #O6437164, CREEGAN GROUP.
Listing provided by Stellar MLS
$208,999
8815 Grand Palms Cir #B
Kissimmee, FL 34747
3 bd · 2 ba · 1,222 sqft
Grand Palms Condo 4 Ph 2
MLS ID #S5141452, PROPERTY OUTLET INTERNATIONAL.
Listing provided by Stellar MLS
$325,000
2382 Silver Palm Dr E
Kissimmee, FL 34747
3 bd · 3 ba · 1,440 sqft
Windsor Palms P3apb14pgs105-106blk10lot2
MLS ID #O6422661, REDFIN CORPORATION.
Listing provided by Stellar MLS
$415,000
1035 Jason Ridge Ct
Kissimmee, FL 34747
4 bd · 2 ba · 1,727 sqft
Indian Ridge Unit 2
MLS ID #G5118262, MOBED REALTY, P.A..
Listing provided by Stellar MLS
$318,900
3145 Caribbean Soul Dr
Kissimmee, FL 34747
2 bd · 3 ba · 1,380 sqft
Rolling Oaks Ph 7
MLS ID #O6413644, MORGAN PROPERTY SOLUTIONS INC.
Listing provided by Stellar MLS
$249,900
8424 Crystal Cove Loop
Kissimmee, FL 34747
3 bd · 3 ba · 1,291 sqft
Emerald Island Resort Ph 2
MLS ID #O6404613, COMPASS FLORIDA LLC.
Listing provided by Stellar MLS
$459,000
2147 Cooper Bell Pl
Kissimmee, FL 34747
5 bd · 5 ba · 2,294 sqft
Solara Resort Vacation Villas
MLS ID #O6436144, KRESSLER REAL ESTATE.
Listing provided by Stellar MLS
$399,000
792 Driving Range Ct
Reunion, FL 34747
3 bd · 3 ba · 1,659 sqft
Reunion Fairways
MLS ID #O6418913, KRESSLER REAL ESTATE.
Listing provided by Stellar MLS
$455,000
2166 Fleming Mist Pl
Kissimmee, FL 34747
5 bd · 5 ba · 2,294 sqft
Solara Resort Vacation Villas Rep
MLS ID #O6446661, AVANTI WAY REALTY LLC.
Listing provided by Stellar MLS
$416,000
2404 Tanger Dr
Kissimmee, FL 34747
5 bd · 5 ba · 2,263 sqft
Windsor At Westside Ph 3
MLS ID #O6442227, LPT REALTY, LLC.
Listing provided by Stellar MLS
$249,000
9055 Treasure Trove Ln #204
Kissimmee, FL 34747
3 bd · 2 ba · 1,700 sqft
Caribe Cove Condo Ph 4
MLS ID #O6446389, EPIQUE 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 October 2, 2026 at 4:48 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