MLS data updated Jul 18, 2026
Chickasaw Oaks
Established single-family living off S. Chickasaw Trail in Southeast Orlando
Orlando, FL
Chickasaw Oaks is an established single-family residential subdivision in Southeast Orlando along S. Chickasaw Trail, known for tree-lined streets and mature landscaping, low HOA dues, and quick access to the 408 Expressway and Orlando International Airport.
Median sold: $443K · Median days on market: 22 · Sold-to-list: 98.9% · Source: Stellar MLS
About 0.2 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 Oaks
Chickasaw Oaks draws a very specific buyer — someone who wants a detached home with a real yard, mature trees, and a quiet street, without giving up any of Southeast Orlando's highway connectivity. That combination is harder to find than people expect, and it's why this neighborhood consistently attracts working families and dual-income households.
The employment anchor here is the SR-408 and FL-417 interchange just minutes away, which puts downtown Orlando, Orlando International Airport, AdventHealth East Orlando, and the University of Central Florida all within a practical daily commute. For professionals who fly frequently, being under ten minutes from MCO is a genuine quality-of-life advantage that compounds over time.
The housing stock is Traditional and Ranch-style homes built across the 1980s and 1990s — larger lots than anything built after 2000 in this price range, with mature landscaping and the kind of established neighborhood character that newer communities spend decades trying to replicate. Several homes feature screened pools and covered patios, which aligns well with the Florida outdoor lifestyle buyers in this corridor are after.
Buyers cross-shopping Chickasaw Oaks typically look at nearby Chickasaw Trails for similar vintage and access, or at newer product in the Lake Nona corridor for more amenities and a longer commute. Most who prioritize the airport corridor and established lot sizes end up back here.
— Ryan Solberg, Broker/Owner, MaxLife Realty
Under Contract
1 home pending in Chickasaw Oaks · Avg. $420K
Chickasaw Oaks · 3rd Quarter 2026
327 sales · Stellar MLS · last 12 mo
$443K
Median Sale Price
22 days
Median Days on Market
98.9%
Sold-to-List
$247
Median $/sqft
Recent Sales Map
60 recent individual sales in and around Chickasaw Oaks · 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 | — |
| — | — | 1,641 | — | 11/1/25 | — | $390,000 | $238 | — |
| — | — | 1,846 | — | 11/1/25 | — | $390,000 | $211 | — |
| — | — | 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 | — |
| — | — | 2,048 | — | 9/1/25 | — | $405,000 | $198 | — |
| — | — | 1,419 | — | 9/1/25 | — | $405,000 | $285 | — |
| — | — | 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 | — |
| — | — | 1,538 | — | 9/1/25 | — | $235,000 | $153 | — |
| — | — | 1,248 | — | 9/1/25 | — | $225,000 | $180 | — |
| — | — | 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 | — |
Currently For Sale
5 active listings in Chickasaw Oaks
$290/sqft
View details
$240/sqft
View details
View details
$291/sqft
View details
$265/sqft
View details
| Beds | Baths | Sq Ft | List Price | $/Sq Ft | DOM | Pool | View |
|---|---|---|---|---|---|---|---|
| 4 | 2 | 1,510 | $438,000 | $290 | 17 | ✓ | — |
| 4 | 2 | 1,704 | $409,000 | $240 | 121 | — | — |
| — | 0 | — | $289,000 | — | 468 | — | Water |
| 4 | 2 | 1,510 | $439,900 | $291 | 20 | ✓ | — |
| 3 | 3 | 1,580 | $419,000 | $265 | 132 | — | — |
Chickasaw Oaks Market — Common Questions
Is Chickasaw Oaks a buyer's or seller's market in 2026?+
Chickasaw Oaks is currently a seller's market with about 0.2 months of inventory. About 0.2 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 Oaks?+
Based on Florida Department of Revenue public records over the last 6 months, the median sale price in Chickasaw Oaks is approximately $443K, down about 5.6% from a year earlier.
How many homes are for sale in Chickasaw Oaks?+
There are currently 5 active listings in Chickasaw Oaks, with homes selling at roughly 27.3 per month. That works out to about 0.2 months of inventory.
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Ryan Solberg
MaxLife Realty
321.373.3536
Report generated July 19, 2026 at 3:28 PM 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 Oaksor 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 July 18, 2026 at 5:06 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 July 18, 2026 at 5:06 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