Chickasaw Woods
Homes for Sale in Orlando, FL
All 4,060 homes for sale in Orlando, FL · median $384,945 · 83 homes for sale in 32829 · Orange County homes for sale
True comps, carrying-cost math, and listings before the portals.
Over the 12 months ending 2026-09-12, 3 recorded sales closed at a median of $332,500, $232 per square foot, a median 5 days on market, sellers accepting 102% of original asking. Homes listed or recently sold were built 1975–1977. At the median price and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $5,540 ($4,870 with the full homestead exemption).
Chickasaw Woods is a small, tightly held pocket of 167 homes built in a narrow window from 1975 to 1980, and that consistency shows up in pricing. With a median living area around 1,406 square feet and a median price of $326,250, value here is driven far less by size or vintage — everything is roughly the same era and footprint — and far more by condition and updates. Two homes of nearly identical square footage can sit well apart on price depending on kitchens, baths, roof, and systems.
The current posture favors sellers. A median of just 5 days on market against only 4 closings in the window tells you homes are moving quickly on thin supply, not that a flood of inventory is clearing. For buyers that means little room to negotiate and a need to be ready to act; for sellers it means a well-prepared, updated home can command attention fast. The high homestead share — nearly 78% — signals owners tend to stay put, which keeps turnover low and listings scarce.
Nearby homes for sale
No active listings inside Chickasaw Woods right now. These are the 6 closest homes on the market, by straight-line distance from the community's center; some may sit just outside its boundary.
Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.
The 60-Second Overview
Chickasaw Woods market snapshot (as of September 12, 2026): the median sale price is about $332K ($232 per sq ft over the trailing 12 months of closed sales), and a median 5 days on market for closed sales.
In ZIP 32829 (Orlando), 340 homes closed in the last 12 months at a median of $417K ($252/sq ft), down 8.8% year over year, with a median 29 days on market. Right now 59 active and 19 pending listings put supply at about 3.3 months — a balanced market. See the live ZIP 32829 housing market and the Orange County market.
Stellar MLS sales records identify 126 homes in Chickasaw Woods that have changed hands since 2004, built between 1975 and 1980 (median 1978), with a median living area of about 1,432 sq ft and a typical 3-bedroom, 2-bath layout; 100% are single-family homes. Source: Stellar MLS closed-sale history compiled by Momentum Research; counts reflect homes with a recorded MLS sale, not every home in the community.
Chickasaw Woods is a compact, late-1970s established neighborhood in east Orlando's Orange County where homes are similar in age and size, so the real pricing story is condition, not square footage.
Who Chickasaw Woods is best for.
Best for
- Buyers targeting a roughly $326K price point who value an established, uniform neighborhood over new construction
- Purchasers comfortable acting fast and going in pre-approved on limited inventory
- Owner-occupants planning to stay long-term who want a home they can update over time
Probably not for
- Buyers who need a large selection of listings to compare at once
- Anyone counting on negotiating leverage in a slow-moving market
- Those seeking larger, newer construction beyond a 1,406-square-foot, late-1970s footprint
Price History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending September 12 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($332K) IS the median in the snapshot above.
Windows contain 0 to 8 sales each (3 in the current window); every figure carries its sample size, and thin markets swing on single closings. Based on Stellar MLS data distributed by MLS GRID for the period 2006 through 2026. Deemed reliable but not guaranteed.
Chickasaw Woods Market Scorecard
Chickasaw Woods is currently a no active listings market. Limited supply, a median asking price of n/a.
Typical home value in the 32829 ZIP is $405,538, about 13.6% below the Florida norm (Zillow Home Value Index).
Go deeper: ZIP market scorecard · county scorecard · true cost calculator · affordability calculator.
Live data: realMLS, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.
Chickasaw Woods on the map.
Every active, pending, and recently sold home, plotted. Toggle the layers and tap a home for the details.
Listing locations from Stellar MLS. Map data © OpenStreetMap, tiles © CARTO.
The Chickasaw Woods buying strategy.
If we were buying in Chickasaw Woods today, this is the order of operations we would run for our clients.
Underwrite the condition first. Price the roof, HVAC, and systems honestly before judging any list price; condition swings value here more than square footage alone.
Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.
Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.
Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.
Keep an agent in your corner. The listing agent works for the seller; we represent you and prepare a hand-built valuation before any offer in Chickasaw Woods.
A condition-driven market on thin supply
Because the housing stock was built between 1975 and 1980 and clusters near 1,406 square feet, buyers are essentially choosing between comparable bones. The differentiator is what's been done since: updated systems, roof age, renovated kitchens and baths, and lot position. Expect a wide spread around the $326,250 median that reflects those differences rather than a formal tier of entry-level versus high-end homes.
Supply is the constraint. Only 4 closings in the tracking window and a nearly 78% homestead share point to owners who hold long-term, so listings are infrequent and tend to draw quick interest — the 5-day median time on market is the evidence. If you want in, be pre-approved and prepared to move; if you're selling, presentation and condition are what capture the speed this market is showing.
The location and the amenities are priced into every listing in Chickasaw Woods. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a neighborhood this small with this little turnover, the difference between overpaying and buying right comes down to reading condition against the median — knowing which updates justify a premium and which don't. We track Chickasaw Woods closely enough to tell you when a listing is priced for its work and when it isn't, and we help sellers position a home to earn the fast market this data shows is possible.
Chickasaw Woods in 15 seconds.
HOA, CDD & Fees
- HOA status not on record. Verify any dues before you offer
- Any club/amenity membership is billed separately
Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.
Tools for a Chickasaw Woods buy.
Free calculators to pressure-test the real cost before you tour.
Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Chickasaw Woods sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Chickasaw Woods, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Chickasaw Woods home worth?
Get a no-obligation home value based on real comparable sales in Chickasaw Woods, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.
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Frequently Asked Questions
What is the median home price in Chickasaw Woods?
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Should you buy in Chickasaw Woods?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: September 14, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending September 12, 2026 |
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2006 (32 transactions analyzed) |
Verify the primary sources yourself: Florida DOR · U.S. Census · FEMA flood maps · Citizens Property Insurance.
Momentum Research figures are our own analysis of Stellar MLS records; MLS data is deemed reliable but not guaranteed. Methodology: how Momentum market scores are computed. Market metrics describe homes for sale and recent sales, not residents.
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The numbers on this page move markets in the aggregate. The number that matters to you is what a buyer pays for your address. Momentum sells for 1.25% above the Stellar MLS member average and 8 days faster, and we’ll price yours against live local comps.
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Nearby Communities
Explore more neighborhoods near Chickasaw Woods with Momentum Realty’s local guides.