Chantilly
Homes for Sale in Winter Park, FL
All 356 homes for sale in Winter Park, FL · median $697,000 · 167 homes for sale in 32789 · Orange County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of October 2026, the MLS records 5 closed sales in Chantilly Sub in Winter Park, FL since 2015, the most recent in March 2024. Across Winter Park as a whole, 494 homes closed in the last 12 months at a median of $449,000, 33 median days on market, with 128 homes for sale today. At that median and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $7,490 ($6,810 with the full homestead exemption).
Chantilly is a small, established pocket of Winter Park where the housing stock tells the story more than any single number does. With a median year built of 1959 but a range that stretches to 2024, this is a community where original mid-century homes sit alongside newer builds or substantial renovations on the same streets. That spread means condition and vintage, not location alone, will drive how a given listing is priced and how it's received.
The homestead share of 64.1% suggests a market weighted toward owner-occupants rather than transient rental turnover, which tends to support steadier upkeep and fewer distressed sales cycles. For buyers, that means less competition from bulk investors but also fewer flips hitting the market at once. For sellers, it points to a pool of buyers who are evaluating the home for long-term use, so presentation and condition disclosures carry real weight.
Nearby homes for sale
No active listings inside ChantillyHomes for Sale in Winter Park, FL 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
Chantilly is a compact, established neighborhood in Winter Park with a housing stock spanning original 1950s construction through recent builds, giving buyers a genuine mix of eras to choose from rather than a single uniform product.
Stellar MLS sales records identify 5 homes in Chantilly that have changed hands since 2012, built between 1998 and 2000 (median 1998), with a median living area of about 3,350 sq ft and a typical 4-bedroom, 4-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.
County records show 4 qualified sales in Chantilly across 2024–2025 (3 in 2024, 1 in 2025), median $1.25M — the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.
Pre-construction details are compiled from public records, builder announcements and builder listings, and are subject to change without notice; figures are deemed reliable but not guaranteed. Momentum Research figures are our own analysis. This page describes homes, pricing and community attributes, not residents.
Who Chantilly is best for.
Best for
- Buyers seeking an established Winter Park lot with flexibility to renovate or rebuild over time.
- Buyers who want a smaller, low-turnover market and are comfortable doing detailed home-by-home diligence.
- Buyers targeting a modest living-area footprint as either a starting point or a long-term home.
Probably not for
- Buyers who want a neighborhood built around shared recreational amenities.
- Buyers who need a large, high-volume inventory to compare similar homes quickly.
- Buyers uncomfortable with variation in home age and condition across a small number of listings.
The market around Chantilly
Chantilly is too small for its own price trend, so here is the market around it.
In ZIP 32789, 244 homes are on the market and 25% are under contract — a steady corner of Winter Park.
Across Orange County, 5,909 homes are active and 1,877 pending (24% under contract).
In ZIP 32789 (Winter Park), 390 homes closed in the last 12 months at a median of $635K ($396/sq ft), up 7.6% year over year, with a median 39 days on market. Right now 91 active and 26 pending listings put supply at about 5.2 months — a balanced market. See the live ZIP 32789 housing market and the Orange County market.
ZIP and county figures describe the wider market, not Chantilly specifically. Momentum Research analysis of MLS records.
The Chantilly buying strategy.
If we were buying in Chantilly 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 Chantilly.
A Small Market With a Wide Age Range
With only 61 homes, Chantilly is not a high-volume market, and that scarcity shapes how it should be shopped. A median year built of 1959 confirms the neighborhood's mid-century roots, but the range running to 2024 means some parcels have seen full rebuilds or new construction. Buyers should expect real variation in systems, layouts, and finish level from one listing to the next, and should treat each home on its own merits rather than assuming a neighborhood-wide standard.
Median living area of 1,495 square feet points to a modest-footprint market, consistent with the era of original construction, though newer or renovated homes on the same streets may deviate from that baseline. No community amenities are identified in current MLS listings, so this is a neighborhood defined by its lots and homes rather than shared recreational infrastructure. Anyone evaluating Chantilly should focus diligence on individual home condition and recent updates rather than assuming amenity-driven value.
The location and the amenities are priced into every listing in Chantilly. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a market this small, with only 61 homes and a seven-decade construction span, the difference between an original 1959 structure and a recent rebuild is not always obvious from photos or public record. We walk buyers and sellers through what condition, permitting history, and renovation scope actually mean for a given address, so pricing and offer decisions are based on the real state of the home, not assumptions about the neighborhood.
Chantilly 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 Chantilly 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 Chantilly sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Chantilly, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Chantilly home worth?
Get a no-obligation home value based on real comparable sales in Chantilly, 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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Should you buy in Chantilly?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2015 (5 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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You just read the data. Now see what your home is worth.
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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Common questions about Chantilly
Where is Chantilly?
Chantilly is a community in Winter Park, Orange County, Florida, ZIP 32789.
Are there homes for sale in Chantilly right now?
No active listings inside Chantilly at the last feed refresh. The nearest homes for sale, with distances from the community, are shown on this page and refreshed nightly.
Does Chantilly have an HOA or CDD?
No HOA is on record for Chantilly in our data. Verify dues, what they cover, and any special assessment for a specific address before you offer.
Answers are generated from county property records, MLS feeds and the figures on this page, as of the page date; deemed reliable but not guaranteed.
Nearby Communities
Explore more neighborhoods near Chantilly with Momentum Realty’s local guides.