MLS data updated Apr 10, 2026
Chickasaw Trails
Established southeast Orlando single-family homes with low HOA and quick expressway access
Orlando, FL
Chickasaw Trails is an established single-family-home subdivision in southeast Orlando (ZIP 32829), built largely in the early 1990s, known for its low monthly HOA, nature trails, and convenient access to the 408, 417, and 528 expressways and Orlando International Airport.
Median sold: $445K · Median days on market: 22 · Sold-to-list: 98.9% · Source: Stellar MLS
About 0 months of inventory — homes are selling faster than new ones come on the market, so sellers hold the leverage (under 4 months = seller's market).
Aggregate statistics from recent Stellar MLS closed sales and live MLS inventory. A market read, not an appraisal of any home or a listing of individual sales.
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Ryan's Take on Chickasaw Trails
Chickasaw Trails draws a specific buyer: the dual-income professional household that wants a cohesive, owner-occupied neighborhood with a genuine commute to downtown Orlando and no appetite for HOA fees on amenities they won't use. The low monthly dues, 1990s homes with real square footage, and non-gated character signal that value and location win over prestige branding here.
The SR-408 on-ramp is the employment anchor. Residents reach downtown Orlando in roughly 15 to 20 minutes, UCF's campus via the east corridor, and Orlando International Airport about 10 to 15 minutes south on Chickasaw Trail — three major employment nodes without surface-street gridlock. Florida Hospital of East Orlando and Valencia College add institutional employment in the same corridor.
The housing stock's defining quality is consistency: the neighborhood built out between 1990 and 1994, producing maintained streets, established tree canopy, and three-to-five-bedroom homes in the 1,400–2,500 square foot range. Chickasaw Elementary's Gifted and Talented program and the on-corridor Renaissance Charter K–8 school give families real school optionality without leaving the zip code.
Buyers cross-shopping this area look at Chickasaw Oaks to the northwest or Lee Vista communities to the east. Chickasaw Trails earns the comparison on school access, expressway proximity, and HOA cost together — a combination that is hard to replicate in southeast Orlando.
— Ryan Solberg, Broker/Owner, MaxLife Realty
Chickasaw Trails · 2nd Quarter 2026
323 sales · Stellar MLS · last 12 mo
$445K
Median Sale Price
22 days
Median Days on Market
98.9%
Sold-to-List
$248
Median $/sqft
Recent Sales Map
60 recent individual sales in and around Chickasaw Trails · FL public records · no addresses published
Approximate sale locations — dots are offset ±1 home for privacy
| Beds | Baths | Sq Ft | Listed | Sold ▼ | List Price | Sold Price | $/Sq Ft | DOM |
|---|---|---|---|---|---|---|---|---|
| — | — | 3,462 | — | 12/1/25 | — | $825,000 | $238 | — |
| — | — | 2,554 | — | 12/1/25 | — | $610,000 | $239 | — |
| — | — | 2,159 | — | 12/1/25 | — | $475,000 | $220 | — |
| — | — | 2,574 | — | 12/1/25 | — | $474,000 | $184 | — |
| — | — | 1,827 | — | 12/1/25 | — | $440,000 | $241 | — |
| — | — | 1,726 | — | 12/1/25 | — | $420,000 | $243 | — |
| — | — | 1,259 | — | 12/1/25 | — | $375,000 | $298 | — |
| — | — | 1,020 | — | 12/1/25 | — | $327,000 | $321 | — |
| — | — | 1,452 | — | 12/1/25 | — | $309,900 | $213 | — |
| — | — | 1,774 | — | 12/1/25 | — | $300,000 | $169 | — |
| — | — | 1,452 | — | 12/1/25 | — | $296,300 | $204 | — |
| — | — | 2,930 | — | 11/1/25 | — | $657,900 | $225 | — |
| — | — | 3,187 | — | 11/1/25 | — | $600,000 | $188 | — |
| — | — | 2,214 | — | 11/1/25 | — | $590,000 | $266 | — |
| — | — | 2,574 | — | 11/1/25 | — | $505,000 | $196 | — |
| — | — | 2,049 | — | 11/1/25 | — | $445,000 | $217 | — |
| — | — | 2,049 | — | 11/1/25 | — | $429,900 | $210 | — |
| — | — | 1,731 | — | 11/1/25 | — | $425,000 | $246 | — |
| — | — | 1,661 | — | 11/1/25 | — | $415,000 | $250 | — |
| — | — | 1,635 | — | 11/1/25 | — | $415,000 | $254 | — |
| — | — | 1,833 | — | 11/1/25 | — | $393,000 | $214 | — |
| — | — | 1,846 | — | 11/1/25 | — | $390,000 | $211 | — |
| — | — | 1,641 | — | 11/1/25 | — | $390,000 | $238 | — |
| — | — | 1,484 | — | 11/1/25 | — | $371,000 | $250 | — |
| — | — | 1,659 | — | 11/1/25 | — | $350,000 | $211 | — |
| — | — | 1,404 | — | 11/1/25 | — | $310,000 | $221 | — |
| — | — | 1,071 | — | 11/1/25 | — | $268,000 | $250 | — |
| — | — | 1,744 | — | 10/1/25 | — | $464,700 | $266 | — |
| — | — | 2,558 | — | 10/1/25 | — | $450,000 | $176 | — |
| — | — | 1,399 | — | 10/1/25 | — | $449,000 | $321 | — |
| — | — | 1,985 | — | 10/1/25 | — | $448,000 | $226 | — |
| — | — | 1,796 | — | 10/1/25 | — | $425,000 | $237 | — |
| — | — | 1,788 | — | 10/1/25 | — | $415,000 | $232 | — |
| — | — | 1,225 | — | 10/1/25 | — | $357,500 | $292 | — |
| — | — | 1,570 | — | 10/1/25 | — | $345,000 | $220 | — |
| — | — | 1,452 | — | 10/1/25 | — | $315,000 | $217 | — |
| — | — | 3,230 | — | 9/1/25 | — | $660,000 | $204 | — |
| — | — | 2,435 | — | 9/1/25 | — | $575,000 | $236 | — |
| — | — | 2,129 | — | 9/1/25 | — | $490,000 | $230 | — |
| — | — | 1,718 | — | 9/1/25 | — | $450,000 | $262 | — |
| — | — | 1,419 | — | 9/1/25 | — | $405,000 | $285 | — |
| — | — | 2,048 | — | 9/1/25 | — | $405,000 | $198 | — |
| — | — | 1,620 | — | 9/1/25 | — | $394,900 | $244 | — |
| — | — | 1,470 | — | 9/1/25 | — | $365,000 | $248 | — |
| — | — | 1,465 | — | 9/1/25 | — | $340,000 | $232 | — |
| — | — | 1,452 | — | 9/1/25 | — | $335,000 | $231 | — |
| — | — | 1,273 | — | 9/1/25 | — | $309,000 | $243 | — |
| — | — | 3,234 | — | 8/1/25 | — | $650,000 | $201 | — |
| — | — | 3,038 | — | 8/1/25 | — | $575,000 | $189 | — |
| — | — | 1,995 | — | 8/1/25 | — | $460,000 | $231 | — |
| — | — | 1,968 | — | 8/1/25 | — | $455,000 | $231 | — |
| — | — | 1,812 | — | 8/1/25 | — | $433,500 | $239 | — |
| — | — | 2,051 | — | 8/1/25 | — | $410,000 | $200 | — |
| — | — | 1,449 | — | 8/1/25 | — | $408,000 | $282 | — |
| — | — | 1,528 | — | 8/1/25 | — | $400,000 | $262 | — |
| — | — | 1,461 | — | 8/1/25 | — | $395,000 | $270 | — |
| — | — | 1,264 | — | 8/1/25 | — | $390,000 | $309 | — |
| — | — | 1,615 | — | 8/1/25 | — | $390,000 | $241 | — |
| — | — | 1,268 | — | 8/1/25 | — | $388,000 | $306 | — |
| — | — | 1,712 | — | 8/1/25 | — | $355,000 | $207 | — |
Currently For Sale
1 active listing in Chickasaw Trails
| Beds | Baths | Sq Ft | List Price | $/Sq Ft | DOM |
|---|---|---|---|---|---|
| 3 | 2 | 1,547 | $385,000 | $249 | 47 |
Chickasaw Trails Market — Common Questions
Is Chickasaw Trails a buyer's or seller's market in 2026?+
Chickasaw Trails is currently a seller's market with about 0 months of inventory. About 0 months of inventory — homes are selling faster than new ones come on the market, so sellers hold the leverage (under 4 months = seller's market).
What is the median home sale price in Chickasaw Trails?+
Based on Florida Department of Revenue public records over the last 6 months, the median sale price in Chickasaw Trails is approximately $445K, down about 7.3% from a year earlier.
How many homes are for sale in Chickasaw Trails?+
There is currently 1 active listing in Chickasaw Trails, with homes selling at roughly 26.9 per month. That works out to about 0 months of inventory.
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Ryan Solberg
MaxLife Realty
321.373.3536
Report generated June 29, 2026 at 9:43 AM ET· Powered by Stellar MLS
MLS Data:Active and pending listing data is sourced from the Stellar MLS as distributed by MLS GRID. 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. The MLS GRID does not guarantee the accuracy of this data, which may not reflect all real estate activity in the area.
Sold Data: Sales analysis is derived from Florida Department of Revenue public property records(arm's-length transactions). Ryan Solberg and MaxLife Realty LLC are not affiliated with Chickasaw Trailsor its HOA. This report is not intended to solicit properties already listed for sale nor to cause a breach of an existing agency relationship. Data should be independently verified. E&OE.
Based on information submitted to the MLS GRID as of April 10, 2026 at 5:16 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.
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 April 10, 2026 at 5:16 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