Chappaqua, NY Housing Market Update 2026: Prices, Inventory & DOM

“Chappaqua” on a market report is a brokerage reporting area, not the Town of New Castle line. The town takes in the Chappaqua and Millwood hamlets. Brokerage “Chappaqua” cuts mostly overlap with it, but they do not follow the town boundary exactly. Inside that area, in-hamlet Colonials on smaller lots, larger-acreage contemporaries on private roads, and newer townhouse and condo product all trade in different competitive sets. A Chappaqua median is a useful temperature check. It is not a value opinion for any one house. An appraisal still has to match the subject’s location, product type, condition, lot size and utility, and the effective date.

This November 2026 Insights post reads the latest closed-sale statistics the way an appraiser does: price level, inventory, days on market (DOM), sale-to-list, and closed volume, with no lifestyle framing. It complements the methodology piece Appraising Homes in Chappaqua, NY and does not replace a property-specific assignment. Local residential coverage is described on the firm’s Chappaqua appraisal page and the Westchester County appraiser hub.

Sources: Three public series are used below. The primary is the Houlihan Lawrence Chappaqua Single Family Monthly Market Report for October 2026 (OneKey MLS). The second is the William Pitt Sotheby’s Chappaqua Market Tracker for October 2026. The third is the Homix OneKey-based Chappaqua report for September 2026 (data as of October 8, 2026), used here for its trailing 12-month series. Different filters produce different counts. That is expected. Appraisers reconcile competing series by reading the filter first, then the number, and by verifying current MLS closed sales for the assignment’s effective date.

October 2026: Chappaqua Single-Family Snapshot

Houlihan Lawrence’s Chappaqua single-family table for October 2026 shows:

• Median sale price: $1,820,000 (+42.7% versus September 2026; +30.8% versus October 2025)
• Average sale price: $1,950,444 (+36.9% MoM; +30.2% YoY)
• Units sold: 9 (−40.0% MoM; −47.1% YoY)
• Average DOM: 38 days (+40.7% MoM; −11.6% YoY)
• Sale-to-list (% of sales price): 104.86% (+2.8% MoM; −0.5% YoY)
• Units for sale: 16 (−20.0% MoM; 0.0% YoY)
• Months of inventory: 1.80 (+38.5% MoM; +100.0% YoY)

Year-to-date context from the same report’s ten-year table (through October 31, 2026): the 2026 YTD median sold price is listed as $1,630,000, about 8.5% above the 2025 full-year median of $1,501,750 on that table. For scale, the same table shows full-year medians of $857,000 in 2017 and $1,502,500 in 2024, so the 2026 YTD median is roughly 90% above the 2017 figure. The prior month’s HL report (September 2026) showed a $1,275,000 median on 15 closings, which is why October’s +42.7% month-over-month jump should be read as a small-sample swing rather than a price trend.

Source: Houlihan Lawrence Chappaqua Single Family Monthly Market Report, October 2026 (OneKey MLS). Figures deemed reliable but not guaranteed; not a value opinion for any subject property.

In Chappaqua, October was a low-volume, high-price month. There were nine single-family closings, about half of October 2025’s count, at a $1.82 million median, sale-to-list near 105%, and a 38-day average DOM. With 16 homes for sale, supply rose to about 1.8 months. That is double a year ago, but it is still well inside seller’s-market territory. Those facts describe market conditions. They do not price any one house.

William Pitt Tracker: Same Month, Different Filter

William Pitt Sotheby’s Chappaqua Market Tracker for October 2026 (single-family unless noted) uses its own Chappaqua boundary. It lines up closely with the HL price, volume, and DOM picture:

• Units sold (October, SF): 9 (−50.0% YoY; +0.0% versus October 2024)
• Median sold: about $1.8 million (+31.6% YoY; +45.6% versus October 2024); average: about $2 million (+33.8% YoY; +13.7% versus October 2024)
• Average DOM: 39 (−10.4% YoY; −23.1% versus October 2024); percentage of asking: 105% (+1.5% YoY)
• Average $/SF: $488 (+3.6% YoY; +11.8% versus October 2024)
• New SF listings (October): 7 (−22.2% YoY; −46.2% versus October 2024)
• YTD SF sold (January–October): 103 (−38.0% versus YTD 2025)
• Other product types: Condo/Co-op 3 sold in October (−50.0% versus October 2024); 28 condo/co-op sales YTD (−15.2% versus YTD 2025)
• Total monthly inventory (all product types): 41 units (−21.2% YoY; −25.5% versus October 2024)

Source: William Pitt Sotheby’s Chappaqua Market Tracker (October 2026). Brokerage dashboard figures are deemed reliable but not guaranteed.

The two brokerage series agree on the headline: nine closings, a median near $1.8 million, a high-30s DOM, and sale-to-list around 105%. The more useful number is price per square foot. WP’s average $/SF rose only 3.6% year over year while its median sale price rose 31.6%. That gap says most of October’s median jump came from which homes sold (larger, higher-priced houses), not from a 30% repricing of the same house. The volume story is the other half: WP counts 103 single-family sales January through October, down 38% from the same period in 2025, and new listings are running well below 2024. Fewer listings, fewer closings, and firm prices describe a supply-constrained market, not a demand collapse.

Homix 12-Month Series: The Calmer Picture

Homix’s OneKey-based Chappaqua report covers September 2026 (data as of October 8, 2026). Its single-month figures are small (seven closings), so the trailing 12-month columns are the part worth reading:

• Single-family, September 2026: median $1,250,000 versus $1,530,000 in September 2025 (−18.3%); 7 closed versus 7; homes for sale 16 versus 11; average DOM 20 versus 41; % of original list 100.3% versus 107.1%; about 1.7 months of supply
• Single-family, 12 months through 09/2026: median $1,638,250 versus $1,600,000 (+2.4%); closed 114 versus 127 (−10.2%); new listings 117 versus 161 (−27.3%); average DOM 28 versus 33; % of original list 109.8% versus 107.3%
• Condo, 12 months through 09/2026: 20 closed versus 38; median $863,000 versus $1,502,995. On this small a sample, the condo median mostly reflects which units sold.

Source: Homix Chappaqua market report. Homix notes its figures are calculated from OneKey MLS data, and small samples can make percent changes look extreme. On 114 closings, the trailing-year median is up a modest 2.4%, and sale-to-original-list near 110% says competitive bidding has persisted across the full year. Notice that Homix’s September median fell 18.3% year over year, while HL’s October median rose 30.8%. Neither single month is the trend.

Why Chappaqua Headlines Mislead

Every series above puts Chappaqua’s typical single-family price somewhere between about $1.6 and $1.8 million over the past year, and the October year-over-year jump is easy to misuse. Common failure modes when someone quotes it as “the Chappaqua market”:

• Mix shift versus price movement: HL’s median rose 30.8% year over year on nine sales, while WP’s average $/SF rose 3.6% and Homix’s 12-month median rose 2.4%. A handful of larger closings can lift the median without any change in what a typical house would bring.
• Monthly versus trailing data: HL’s YTD median is up about 8.5% over 2025. Homix’s trailing-12-month median is up 2.4%. Neither supports a 30% appreciation rate, and a time adjustment built on the October headline would overshoot.
• Thin volume: Nine closings in a month (both HL and WP) is a small sample. One or two sales at either end of the range can move the median by hundreds of thousands of dollars.
• Inventory direction depends on the filter: HL’s months of supply doubled year over year (to 1.8) because closings fell faster than listings. WP’s all-product inventory is down 21.2%. Both can be true. Read which product types and which denominator each series uses before quoting “supply.”
• Sale-to-list is not a blanket premium: About 105% (HL and WP) describes October closed outcomes in aggregate. It does not mean every listing clears above asking, and a 38-day average DOM says some listings took longer.

For a deeper primer on how appraisers parse medians, months of supply, DOM, and sale-to-list, see Market Conditions and How Appraisers Analyze the Stats.

How Appraisers Read Chappaqua’s Competitive Sets

Market-conditions commentary in a Chappaqua appraisal is built from the sales that actually compete with the subject, not from the area headline alone.

• Confirm the location first: Chappaqua hamlet, Millwood, or the larger-lot sections of the Town of New Castle. Pull comps inside that set before expanding to neighboring Armonk, Mount Kisco, Pleasantville, or Bedford sales.
• Bracket size and lot utility: Use $/SF and gross living area as a check on the median. Larger-acreage parcels are bracketed against similar acreage, with attention to usable versus sloped or wetland-encumbered land.
• Time adjustments from the matched set: With the October median up about 31% but the trailing-year median up about 2%, a supported time adjustment comes from paired and repeat sales in the subject’s band, not from the monthly headline.
• Inventory as absorption context: About 1.7 to 1.8 months of single-family supply in every series is seller’s-market territory. New listings running well below prior years mean the appraiser should document active and pending competition inside the subject’s own price and quality band.
• Townhouse and condo product is separate: Condo and townhouse sales are not a basis for a detached single-family conclusion, and vice versa.
• Assessment versus market value: Assessed value is not market value. Tax-grievance work compares the assessment to a current, supportable market-value opinion. See tax grievance and Chappaqua tax grievance 2026.

Estate, Date-of-Death, and Divorce Files When the Month and the Year Disagree

When the October median says +31% and the trailing year says roughly +2%, AVM estimates and area averages are least reliable, and the effective date carries more weight. For files that must stand up for counsel or a fiduciary:

• Estate / date-of-death: A retrospective opinion for Form 706, the New York estate tax return, probate, or fiduciary accounting uses market evidence knowable as of the date of death. An executor who quotes an October 2026 median for a spring 2026 date of death is mixing effective dates, and in a nine-sale month the error can be large. See estate appraisal, date-of-death appraisal, and date of death vs current market value.
• Divorce / equitable distribution: Current or retrospective (including date-of-commencement) valuations of the marital residence. When one spouse cites the October headline and the other cites the trailing year, the effective date and the matched set decide the number, not either headline. See divorce appraisal and date-of-commencement appraisals in NY divorce.
• Attorney and fiduciary briefing: Counsel often need a plain-English read of whether a proposed buyout or listing price is consistent with recent matched sales, not with the town median or an AVM alone. Private USPAP reports differ from lender forms. See private vs lender appraisals and the firm’s attorney resources.

Final Thoughts

As of the October 2026 Houlihan Lawrence Chappaqua single-family report, Chappaqua’s market is tight on price and sale-to-list and thin on volume. The report shows a $1,820,000 median on nine closings, sale-to-list near 105%, a 38-day average DOM, and about 1.8 months of inventory, with closings down 47.1% year over year. The William Pitt tracker backs up the price, volume, and DOM figures, and its 3.6% $/SF gain plus Homix’s 2.4% trailing-12-month median are a reminder that one strong month is not a trend. Mix-driven medians mislead. Those facts describe market conditions. They do not price any one house.

A defensible Chappaqua appraisal still starts with physical evidence and matched sales from the right part of town. That set is then placed against the area statistics as context. Whether the purpose is estate settlement, divorce, tax grievance, or a private purchase opinion, Madison & Park builds the analysis that way across Westchester, Manhattan, and Greenwich CT. Dave Lister, SRA, is a New York certified residential appraiser and is Licensed in Connecticut; Court Approved status applies in New York only.

Hero photo: Greeley House, Chappaqua, NY, by ajay_suresh, via Wikimedia Commons, licensed CC BY 2.0; resized.