Chickasaw Trails Homes $500K–$750K for Sale
Every home priced $500K–$750K 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 $500K–$750K in Chickasaw Trails
$554,900
7438 Chelsea Harbour Dr
Orlando, FL 32829
4 bd · 3 ba · 2,629 sqft
Vista Lakes Vlgs N-16 & N-17 Win
MLS ID #S5158515, PARTNERSHIP REALTY INC..
Listing provided by Stellar MLS
$565,000
9808 Bennington Chase Dr
Orlando, FL 32829
5 bd · 4 ba · 3,389 sqft
Tivoli Woods Village C 51 84
MLS ID #O6405715, REALTY OF AMERICA.
Listing provided by Stellar MLS
$699,000
6930 Remington View Ct
Orlando, FL 32829
5 bd · 4 ba · 3,185 sqft
Vista Lakes Village N-15 Carlisle
MLS ID #O6443869, FLORIDA ONE REAL ESTATE LLC.
Listing provided by Stellar MLS
$599,990
10704 Leafy Laurel Street
Orlando, FL 32829
4 bd · 3 ba · 2,341 sqft
Everbe
MLS ID #O6423507, PULTE REALTY OF NORTH FLORIDA LLC.
Listing provided by Stellar MLS
$669,500
6738 Vista Park Blvd
Orlando, FL 32829
4 bd · 3 ba · 3,055 sqft
Vista Lakes Village N-15 Carlisle
MLS ID #O6440029, COLDWELL BANKER REALTY.
Listing provided by Stellar MLS
$649,000
5879 Lake Melrose Dr
Orlando, FL 32829
5 bd · 3 ba · 3,314 sqft
Vista Lakes Village N-7 Melrose
MLS ID #TB8505480, FLAT FEE MLS REALTY.
Listing provided by Stellar MLS
$629,990
7239 Ivy Tendril Ave
Orlando, FL 32829
4 bd · 2 ba · 1,850 sqft
Everbe
MLS ID #O6411160, EXP REALTY LLC.
Listing provided by Stellar MLS
$524,990
10710 Leafy Laurel Street
Orlando, FL 32829
3 bd · 2 ba · 1,715 sqft
Everbe
MLS ID #O6435782, PULTE REALTY OF NORTH FLORIDA LLC.
Listing provided by Stellar MLS
$599,990
10764 Leafy Laurel Street
Orlando, FL 32829
4 bd · 3 ba · 2,341 sqft
Everbe
MLS ID #O6435767, PULTE REALTY OF NORTH FLORIDA LLC.
Listing provided by Stellar MLS
$584,990
10734 Leafy Laurel Street
Orlando, FL 32829
4 bd · 3 ba · 2,341 sqft
Everbe
MLS ID #O6435762, PULTE REALTY OF NORTH FLORIDA LLC.
Listing provided by Stellar MLS
$539,990
10740 Leafy Laurel Street
Orlando, FL 32829
3 bd · 2 ba · 1,715 sqft
Everbe
MLS ID #O6423393, PULTE REALTY OF NORTH FLORIDA LLC.
Listing provided by Stellar MLS
$620,000
5729 Wooden Pine Dr
Orlando, FL 32829
4 bd · 3 ba · 2,397 sqft
Pinewood Reserve Ph 1
MLS ID #O6427530, EXP REALTY LLC.
Listing provided by Stellar MLS
$664,000
6030 Arbor Watch Loop
Orlando, FL 32829
4 bd · 4 ba · 2,860 sqft
Pinewood Reserve
MLS ID #O6434426, MAXLIFE REALTY LLC.
Listing provided by Stellar MLS
$629,900
4317 Hickory Stone Cir
Orlando, FL 32829
5 bd · 3 ba · 4,066 sqft
Tivoli Woods Village B 51 74
MLS ID #O6430981, MAINSTAY BROKERAGE LLC.
Listing provided by Stellar MLS
$738,000
6527 Bayboro Ct
Orlando, FL 32829
4 bd · 3 ba · 2,782 sqft
Vista Lakes Village N-1 Pembroke
MLS ID #O6428049, KELLER WILLIAMS ADVANTAGE III.
Listing provided by Stellar MLS
$632,000
8552 Keswick Pointe Dr
Orlando, FL 32829
5 bd · 4 ba · 3,393 sqft
Vista Lakes Village N-15 Carlisle
MLS ID #O6410733, PREMIUM PROPERTIES R.E SERVICE.
Listing provided by Stellar MLS
$547,900
3632 Creswick Cir
Orlando, FL 32829
4 bd · 3 ba · 2,712 sqft
Victoria Lndgs
MLS ID #O6404682, CHARLES RUTENBERG REALTY ORLANDO.
Listing provided by Stellar MLS
$580,000
10876 Waterwood Aly
Orlando, FL 32829
4 bd · 3 ba · 2,341 sqft
Everbe 1st Amendment
MLS ID #O6434331, KELLER WILLIAMS WINTER PARK.
Listing provided by Stellar MLS
$649,000
6952 Rosy Sky Ave
Orlando, FL 32829
3 bd · 2 ba · 1,655 sqft
Everbe Ph 1c
MLS ID #TB8501192, EXP REALTY LLC.
Listing provided by Stellar MLS
$650,000
10049 Savannah Bluff Ln
Orlando, FL 32829
5 bd · 4 ba · 3,439 sqft
Tivoli Woods Village C
MLS ID #O6394108, RE/MAX TOWN CENTRE.
Listing provided by Stellar MLS
$665,000
6711 Willow View Ave
Orlando, FL 32829
5 bd · 4 ba · 2,635 sqft
Everbe Ph 1c
MLS ID #O6396924, LPT REALTY, LLC.
Listing provided by Stellar MLS
$585,000
10114 Oak Crest Rd
Orlando, FL 32829
3 bd · 3 ba · 2,695 sqft
Tivoli Woods Village B
MLS ID #O6426803, FLORIDA REALTY INVESTMENTS.
Listing provided by Stellar MLS
$669,900
5047 Adair Oak Dr
Orlando, FL 32829
5 bd · 4 ba · 3,439 sqft
Tivoli Woods Village C 51 84
MLS ID #O6423228, CROWN LEGACY REALTY LLC.
Listing provided by Stellar MLS
$550,000
4984 Birch Stone Ln
Orlando, FL 32829
5 bd · 3 ba · 2,844 sqft
Tivoli Woods Vlg B
MLS ID #O6420594, VELEZ COURTESY MANAGEMENT.
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 6:49 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