Homes, values and local insight for Chaplin, Windham County, Connecticut. Typical home value $371,000.
Reviewed and updated October 3, 2026 by Ryan and Megan Winslow, Winslow Homes
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Chaplin is a vibrant Connecticut community in Windham County with 2,100 residents. Properties feature classic New England character with modern amenities. The town provides excellent schools, recreation, and convenient access to major employment centers. Chaplin combines suburban living with strong community bonds and outdoor opportunities.
The Chaplin housing market reflects Connecticut's steady real estate demand. Neighborhoods feature established charm alongside contemporary updates. Properties range from historic homes to modern renovations, offering options across budgets. Parks, trails, and community spaces support active lifestyles. Local schools attract families seeking quality education. The market supports both owner-occupants and investment strategies.
Winslow Homes serves Connecticut 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.
Original town center with character and community.
Price Range: $230K-$380K
Quiet streets with solid family homes.
Price Range: $230K-$380K
Larger properties on spacious land.
Price Range: $230K-$380K
Close to shops and services.
Price Range: $230K-$380K
Wooded, spacious settings.
Price Range: $230K-$380K
Schools, parks, and activities make the town family-friendly.
Local and regional options serve daily needs.
Trails, parks, and outdoor spaces year-round.
Strong local events and connections.
Seasonal events and community gathering.
Shops, cafes, local businesses.
Recreation and family activities.
Books, programs, and community hub.
The typical home in Chaplin is worth $371,000, 2% below the Windham County typical value of $377,000 and 18% below the Connecticut typical value of $451,000.
Zillow Home Value Index for Chaplin, August 2026. The middle of the market for single family homes and condos.
Home values in Chaplin moved +41.2% over five years and +101.6% over ten.
Median gross rent in Chaplin. Useful for investors running rental numbers.
Share of occupied homes in Chaplin lived in by the owner.
A newer housing stock means fewer surprises at inspection.
Median household income in Chaplin.
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 Chaplin home of $371,000:
Ryan and Megan price Chaplin homes from recent sales, not guesses. Send your address and you get a free market analysis, with no obligation.
Typical value $404,000 · 1,759 residents
Area guide →Typical value $406,000 · 27,996 residents
Area guide →Typical value $333,000 · 24,105 residents
Area guide →Typical value $382,000 · 1,598 residents
Area guide →Typical value $416,000 · 1,706 residents
Area guide →Typical value $399,000 · 4,263 residents
Area guide →See the full Windham County real estate guide or the Connecticut real estate guide.
The Zillow Home Value Index for Chaplin was $371,000 in August 2026, +7.8% over the past year.
Chaplin is in Windham County, Connecticut.
About 2,179 people as of the 2024 Census Bureau estimate, up from 2,152 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.
83% of occupied homes in Chaplin 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 Chaplin, CT before they hit the big home search sites.
The typical home in Chaplin is worth $370,682 as of August 2026 in ZIP code 06235. Values moved +8.0% 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 |
|---|---|---|---|---|---|
| 06235 | $370,682 | +8.0% | +41.5% | $450,000 | 23 |
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.
