Search "Chappaqua median home price" this month and you will get at least three different numbers before you finish your coffee. One source will tell you homes are trading in the high $700,000s. Another will show a typical value north of $1.5 million. A third, pulled straight from brokerage sales data, will put the median at $1.74 million. None of these numbers are wrong. They are just measuring three different places that all happen to share the word Chappaqua.
That is the part almost no comparison guide tells a relocating buyer: Chappaqua is not a town. It is a hamlet inside the Town of New Castle, and the boundary that actually sets the price premium isn't the one on your mailing address.
A Town With No Address of Its Own
New Castle is the actual municipal government here, and it is a strange one. The town includes the hamlets of Chappaqua and Millwood, but residents scattered across New Castle can carry an Ossining, Armonk, Briarcliff Manor, Mount Kisco, or Pleasantville mailing address depending on which corner of town they live in. There is no location inside New Castle that is itself addressed as "New Castle." The name exists on your tax bill and your voter registration. It does not exist on your envelope.
That matters because when a portal reports a price for "New Castle, NY," it is quietly folding in homes that nobody who lives there would ever call Chappaqua, and excluding some that locals absolutely would.
Three Lines, Three Different Answers
Layer the ZIP code and the school district on top of the town line and the picture gets messier, not clearer.
| Boundary | What it actually covers | Why it matters to a buyer |
|---|---|---|
| ZIP code 10514 | Centered on Chappaqua but bleeding into Millwood, Mount Pleasant, North Castle, Yorktown, Mount Kisco, and Bedford | Portal medians built off this ZIP are averaging in homes outside the school district that commands the premium |
| Chappaqua Central School District | Covers most of New Castle and part of Mount Pleasant, and also reaches into the 10570 Pleasantville ZIP | This is the boundary that actually drives the price a buyer competes for, and it does not match the ZIP map |
| Town of New Castle | Includes Chappaqua and Millwood hamlets, plus pockets addressed as Ossining, Armonk, or Pleasantville | The municipal tax and governance boundary, useful for permits and assessments, not for comparing sale prices |
Three separate lines, drawn by three separate authorities, for three separate purposes. A buyer comparing "Chappaqua" to another Westchester suburb is often comparing one of these footprints to a completely different kind of boundary somewhere else, without realizing it.
A home can sit inside the 10514 ZIP and still feed into a different school district. A home can carry a Pleasantville mailing address and still feed into Chappaqua's. The ZIP code on the listing sheet tells you almost nothing about which premium you are actually paying for.
The Number That Actually Sets the Premium
Here is the boundary that moves price: the school district line, not the ZIP, not the town seal.
Houlihan Lawrence's own market report for the Chappaqua school district puts the single-family median sale price at $1,740,000 as of the end of June 2026, up 15.8 percent from June 2025. The average sale price for the same month came in at $1,938,859. Homes that closed in June sold at 118.2 percent of list price on average, meaning the typical seller received nearly a fifth more than they asked. Inventory sat at just 1.0 months' supply, and only 14 homes were on the market at month's end, down 62.2 percent from a year earlier.
Put plainly: this is a market where there is barely one month of homes to buy at any given moment, and the ones that do come up are frequently bid past their asking price. That is not a description of Chappaqua the ZIP code. It is a description of Chappaqua the school district, because that is the boundary buyers are actually fighting over.
Why Your Zillow Number and Your Agent's Number Disagree
The gap between the district figure and the broader portal figures comes from more than geography alone. Two other things are stacked on top of the boundary mismatch.
The first is what's being measured. A district-level median sale price counts only homes that actually closed. A home value index, the kind Zillow publishes, is an estimate of typical value across an entire area, whether or not anything sold there recently. Zillow's figure for "Chappaqua, NY," last updated May 31, 2026, put the average home value at $1,505,914, up 10.1 percent over the prior year. That is a reasonable estimate for a wider footprint, but it is not the same measurement as an actual closed sale price inside the school district.
The second is home type. Broader ZIP-level figures typically blend single-family homes with condos, co-ops, and smaller starter properties, all of which pull the median down. One such snapshot, dated to November 2025, showed a ZIP-based median sale price of $802,000 for the area, a figure that reflects a mix of property types across a wider boundary rather than the single-family district data above.
Layer all three differences together, the geography, the metric, and the home type, and a three-fold gap between reported medians stops looking like a contradiction. It looks like three different questions being asked and answered correctly.
Before You Compare Chappaqua to Anywhere Else
A buyer weighing Chappaqua against another Westchester or Rivertowns community should confirm a few things before treating any number as comparable.
- Ask which boundary the number is built from. A ZIP-level figure and a school-district figure are not interchangeable, even when both are labeled "Chappaqua."
- Check the specific parcel's district assignment rather than assuming the mailing address settles it. A 10570 Pleasantville address can still sit inside the Chappaqua Central School District.
- Separate a home value estimate from an actual closed sale price. One is a model. The other is what someone paid.
- Note whether the figure includes condos and co-ops or only single-family homes, since blending property types changes the median significantly.
What This Means If You're Comparing Neighborhoods
For a buyer who has already toured a few towns and is weighing Chappaqua against something else on the list, the practical takeaway is this: the number worth trusting is the one built from the school district boundary, because that is the boundary the market is actually pricing. A ZIP-level average is a reasonable starting point for a first pass, but it will consistently understate what a genuinely comparable home inside the district costs right now.
It also means the search doesn't have to stop at the most obvious streets. Because the district reaches into the edge of the 10570 ZIP and touches parts of Mount Pleasant, there can be homes that carry the same school-district premium without sitting in the highest-competition pocket of the hamlet center. For a buyer comfortable evaluating condition and layout rather than chasing the most visible listings, that is where a little patience and a willingness to look past the ZIP code can pay off.
A Short FAQ
Is Chappaqua its own incorporated village? No. Chappaqua is an unincorporated hamlet inside the Town of New Castle. There is no separate village government to search for permits or zoning, since those functions run through New Castle.
If a listing has a 10514 address, is it automatically in the Chappaqua school district? Not necessarily. The ZIP code and the school district boundary overlap heavily but are not identical. Confirming district assignment for a specific parcel is worth doing before assuming a listing carries the premium associated with the district.
Why did the median jump so much this year? The Chappaqua school district's single-family median rose 15.8 percent year over year through June 2026, driven in large part by inventory sitting at just 1.0 months of supply, meaning very few homes for a steady pool of buyers, which pushed the average sale price to 118.2 percent of list.
Numbers like these are exactly why a boundary-blind comparison can mislead a buyer who is trying to make a fair, apples-to-apples decision. If you're weighing Chappaqua against another Westchester or Rivertowns community and want the district-verified picture rather than the ZIP-level average, Roseanna Tedone can walk you through what a specific address actually carries before you write an offer. Let's Connect.
