Chickasaw Trails Homes Under $500K for Sale
Every home priced under $500K currently for sale in Chickasaw Trails — pulled live from the Stellar MLS and updated continuously. Pair this with the free Chickasaw Trails 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 Chickasaw Trails
$310,000
6246 Westcott Cove Blvd
Orlando, FL 32829
2 bd · 3 ba · 1,276 sqft
Vista Lakes Town Center 51 07
MLS ID #O6435329, COLDWELL BANKER REALTY.
Listing provided by Stellar MLS
$455,000
5737 Lake Champlain Dr
Orlando, FL 32829
4 bd · 2 ba · 2,102 sqft
Vista Lakes Village N-6 Champlain
MLS ID #O6444577, INTERMIX REAL ESTATE INC.
Listing provided by Stellar MLS
$299,000
10332 Manderley Way #111
Orlando, FL 32829
2 bd · 3 ba · 987 sqft
Victoria Pines Condo
MLS ID #O6432594, MAINFRAME REAL ESTATE.
Listing provided by Stellar MLS
$399,900
5264 Sapling Sprout Dr
Orlando, FL 32829
4 bd · 3 ba · 1,809 sqft
Pinewood Reserve Phase 1
MLS ID #O6444333, WEMERT GROUP REALTY LLC.
Listing provided by Stellar MLS
$429,000
8251 Newbury Sound Ln
Orlando, FL 32829
4 bd · 2 ba · 1,864 sqft
Vista Lakes Community Association Inc
MLS ID #O6436205, CARRIGAN LAND GROUP, LLC.
Listing provided by Stellar MLS
$409,999
8320 Southern Forest Dr
Orlando, FL 32829
3 bd · 2 ba · 1,324 sqft
Spring Village
MLS ID #O6431611, AVENIR REAL ESTATE BROKERS LLC.
Listing provided by Stellar MLS
$370,000
8625 Redskin Ct
Orlando, FL 32829
3 bd · 2 ba · 1,436 sqft
Chickasaw Trails Ph 01
MLS ID #O6442696, MARK SPAIN REAL ESTATE.
Listing provided by Stellar MLS
$474,990
10106 Hadley St
Orlando, FL 32829
4 bd · 3 ba · 1,847 sqft
Everbe
MLS ID #O6386860, PULTE REALTY OF NORTH FLORIDA LLC.
Listing provided by Stellar MLS
$465,000
5437 Florence Harbor Dr
Orlando, FL 32829
4 bd · 2 ba · 2,140 sqft
Vista Lakes Vlgs N-8 & N-9
MLS ID #O6418931, MARK SPAIN REAL ESTATE.
Listing provided by Stellar MLS
$346,900
9863 Tivoli Villa Dr
Orlando, FL 32829
3 bd · 3 ba · 1,809 sqft
Crowntree Lakes 02 & 03
MLS ID #S5157082, NONA LEGACY POWERED BY LA ROSA.
Listing provided by Stellar MLS
$484,900
8857 Palisades Beach Ave
Orlando, FL 32829
5 bd · 3 ba · 2,920 sqft
Vista Lakes Vlgs N-8 & N-9
MLS ID #O6409017, ENTERA REALTY LLC.
Listing provided by Stellar MLS
$424,990
7888 Emerald Palm Street
Orlando, FL 32829
3 bd · 3 ba · 1,683 sqft
Everbe
MLS ID #O6445491, PULTE REALTY OF NORTH FLORIDA LLC.
Listing provided by Stellar MLS
$349,900
9743 Biscotti Ave
Orlando, FL 32829
3 bd · 3 ba · 1,792 sqft
Crowntree Lakes
MLS ID #O6435592, AMERILEAD REALTY LLC.
Listing provided by Stellar MLS
$419,900
4768 Crossbow Ct
Orlando, FL 32829
4 bd · 2 ba · 1,510 sqft
Chickasaw Oaks Ph 03
MLS ID #O6421665, IAD REAL ESTATE.
Listing provided by Stellar MLS
$235,000
6335 Contessa Dr #301
Orlando, FL 32829
3 bd · 2 ba · 1,248 sqft
Horizons/Vista Lakes Ph 4
MLS ID #O6399107, WEMERT GROUP REALTY LLC.
Listing provided by Stellar MLS
$424,990
7876 Emerald Palm Street
Orlando, FL 32829
3 bd · 3 ba · 1,683 sqft
Everbe
MLS ID #O6445123, PULTE REALTY OF NORTH FLORIDA LLC.
Listing provided by Stellar MLS
$460,000
11139 Rising Sun St
Orlando, FL 32829
3 bd · 3 ba · 1,608 sqft
Everbe Ph 1a
MLS ID #O6443620, LIFESTYLE INTERNATIONAL REALTY.
Listing provided by Stellar MLS
$465,000
6926 Reverie Park Ave
Orlando, FL 32829
4 bd · 3 ba · 1,833 sqft
Everbe
MLS ID #O6429057, EXP REALTY LLC.
Listing provided by Stellar MLS
$460,000
3127 Birmingham Blvd
Orlando, FL 32829
4 bd · 2 ba · 1,799 sqft
Bradfordt Park Ph 02
MLS ID #O6426861, WATSON REALTY CORP.
Listing provided by Stellar MLS
$485,000
9955 Medallion Bluff Ln
Orlando, FL 32829
4 bd · 2 ba · 1,972 sqft
Tivoli Woods Village C 51 84
MLS ID #O6421360, COLDWELL BANKER REALTY.
Listing provided by Stellar MLS
$445,000
4875 Sweet Cedar Cir
Orlando, FL 32829
3 bd · 2 ba · 1,560 sqft
Tivoli Woods Village A 51 67
MLS ID #O6378847, CHARLES RUTENBERG REALTY ORLANDO.
Listing provided by Stellar MLS
$309,900
3506 Victoria Pines Dr #150
Orlando, FL 32829
3 bd · 3 ba · 1,472 sqft
Victoria Pines Condo
MLS ID #O6413197, URBAN-O REAL ESTATE SOLUTIONS.
Listing provided by Stellar MLS
$229,900
3423 Wilshire Way Rd #27
Orlando, FL 32829
2 bd · 3 ba · 1,071 sqft
Victoria Pines Condo
MLS ID #O6441767, KELLER WILLIAMS ADVANTAGE 2 REALTY.
Listing provided by Stellar MLS
$359,900
Orlando, Fl
Orlando, FL 32829
3 bd · 3 ba · 1,790 sqft
Crowntree Lakes 02 & 03
MLS ID #O6411048, URBAN CITY REALTY LLC.
Listing provided by Stellar MLS
More Chickasaw Trails 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 4:20 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