Homes, values and local insight for Chilmark, Dukes County, Massachusetts. Typical home value $2,406,000.
Reviewed and updated October 3, 2026 by Ryan and Megan Winslow, Winslow Homes
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Chilmark is a residential town in Dukes County providing living with strong Martha's Vineyard and Exclusive community. The community develops civic pride and family values.
The housing market reflects regional positioning with diverse home types. Properties range from modest to premium estates. Buyer pool includes families, commuters and professionals seeking quality living.
Winslow Homes serves this town's buyers and sellers across FL, MA, CT, and RI. Ryan and Megan Winslow provide both brokerage and mortgage services (Ryan Winslow NMLS #2426605 | Megan Winslow NMLS #2692933). Get pre-approved at www.winslowloan.com or call 386-690-5858.
The typical home in Chilmark is worth $2,406,000, 54% above the Dukes County typical value of $1,558,000 and 263% above the Massachusetts typical value of $662,000.
Zillow Home Value Index for Chilmark, August 2026. The middle of the market for single family homes and condos.
Home values in Chilmark moved +18.9% over five years.
Median gross rent in Chilmark. Useful for investors running rental numbers.
Share of occupied homes in Chilmark lived in by the owner.
A newer housing stock means fewer surprises at inspection.
Median household income in Chilmark.
Ryan and Megan are mortgage bankers with The Federal Savings Bank, lending in all 50 states. You get the home and the loan from one team. On a typical Chilmark home of $2,406,000:
Ryan and Megan price Chilmark homes from recent sales, not guesses. Send your address and you get a free market analysis, with no obligation.
Typical value $1,809,000 · 451 residents
Area guide →Typical value $1,664,000 · 3,637 residents
Area guide →Typical value $1,313,000 · 62 residents
Area guide →Typical value $1,348,000 · 4,927 residents
Area guide →Typical value $1,264,000 · 5,407 residents
Area guide →Typical value $1,869,000 · 5,328 residents
Area guide →See the full Dukes County real estate guide or the Massachusetts real estate guide.
The Zillow Home Value Index for Chilmark was $2,406,000 in August 2026, +2.0% over the past year.
Chilmark is in Dukes County, Massachusetts.
About 1,249 people as of the 2024 Census Bureau estimate, up from 1,214 in 2020.
Ryan and Megan Winslow of Winslow Homes have sold over 3,000 homes since 2009 and are licensed in Florida, Massachusetts, Connecticut and Rhode Island. Call or text 386-690-5858.
Apply at www.winslowloan.com. Ryan and Megan are mortgage bankers with The Federal Savings Bank and lend in all 50 states, including FHA, VA and conventional loans.
88% of occupied homes in Chilmark are owner occupied, based on the 2019 to 2023 American Community Survey.
17 years, over 3,000 homes sold, and one team for the home and the loan. Call or text 386-690-5858.
Sources: U.S. Census Bureau 2024 population estimates and 2019 to 2023 American Community Survey; Zillow Home Value Index, August 2026. Numbers update as new data is released. Talk to Ryan and Megan for current sold prices on your street.
No in-person meeting or phone call needed for most addresses. See your estimated value, price range and value trend in seconds.
Get coming-soon homes, pocket listings and price drops in Chilmark, MA before they hit the big home search sites.
The typical home in Chilmark is worth $2,202,450 as of August 2026 in ZIP code 02535. Values moved +2.6% over the last 12 months at the middle ZIP code.
| ZIP | Typical value | 12 months | 5 years | Median sale, Mar to May 2026 | Days on market |
|---|---|---|---|---|---|
| 02535 | $2,202,450 | +2.6% | +19.4% | $3,710,000 | 219 |
Sources: Zillow Home Value Index through August 2026 and the Redfin Data Center ZIP code tracker, March to May 2026. Ask Ryan and Megan for a value for your own home.
