Chaplin, CT Houses for Sale

/40
$350,000

Open Sun 1PM - 3PM $15K PRICE DROP
- 3 Beds
- 2 Baths
- 2,438 Sq Ft
60 Chaplin St, Chaplin, CT 06235

Welcome to place where time truly is the most beautiful thing. There is a particular kind of feeling when you walk through a historic door like this. Maybe it's the hardwood plank floors that have held two centuries of footsteps. Maybe it's the way the morning light hits the windows on every home on Chaplin Street, a village so notable it's listed on the National Register of Historic Places.

Stephen Daly

KW Legacy Partners

60 Chaplin St, Chaplin, CT 06235
Explore Chaplin
/38
$789,000
- 4 Beds
- 2.5 Baths
- 2,900 Sq Ft
287 S Bear Hill Rd, Chaplin, CT 06235

Set on 3.39 picturesque acres, this beautifully renovated property offers the perfect blend of luxury, function, and country charm-ideal for a mini farm, homestead, or private retreat. The heated and insulated 36x48 Morton barn features front and rear sliding barn doors, 2 horse stalls with potential for 6, 5 doggy doors, water, electric, skylights, and year-round water access-perfect for horses,

Amy Rio

Better Homes and Gardens Real Estate Executive Real Estate

287 S Bear Hill Rd, Chaplin, CT 06235
/40
$434,000

$10K PRICE DROP
- 4 Beds
- 4 Baths
- 3,522 Sq Ft
7 Bates Rd, Chaplin, CT 06235

Step back in time while enjoying modern comforts in this charming 1800s Colonial offering 10 spacious rooms filled with character and natural light. The eat-in kitchen features an original butler's pantry, while the formal dining room and inviting living room each showcase stunning stone fireplaces-both complete with rare beehive ovens. French doors lead from the living room to a beautiful

Emily Turker Berkshire Hathaway NE Prop.

7 Bates Rd, Chaplin, CT 06235
/39
$495,000

$100K PRICE DROP
- 3 Beds
- 1.5 Baths
- 1,504 Sq Ft
203 Willimantic Rd, Chaplin, CT 06235

Well-maintained 3-bedroom, 1.5-bath Cape that offers unique flexibility. For more than 75 years, this property was home to a family-run monument business, seamlessly blending residential living with a working space-an ideal setup for today's live/work lifestyle or those simply seeking extra room to fit their needs. Inside, you'll find a functional and inviting layout filled with character. The

Sherry Borgeson Berkshire Hathaway NE Prop.

203 Willimantic Rd, Chaplin, CT 06235
/23
$389,900
- 3 Beds
- 2 Baths
- 1,610 Sq Ft
222 Tower Hill Rd, Chaplin, CT 06235

Beautifully set on 4.02 scenic acres in Chaplin, Connecticut, this charming 3-bedroom, 2-bath home offers the perfect blend of character, privacy, and versatility. Featuring approximately 1,600 square feet, the home showcases soaring vaulted ceilings, stunning exposed beams, and an inviting open-concept kitchen, dining, and living area filled with natural light. The finished lower level offers a

Lisa Therecka Therecka & Associates LLC

222 Tower Hill Rd, Chaplin, CT 06235

Connecticut Windham County Chaplin

Why Live in Chaplin

Chaplin, nestled in the rolling hills of northeastern Connecticut, provides a rural lifestyle with the Natchaug River running through its center. This small Windham County community, home to fewer than 2,200 residents, is surrounded by state-owned forests, offering a peaceful setting. Properties in Chaplin are spacious, often covering several acres, and feature a variety of home styles including ranch-style homes, Cape Cods, farmhouses, and historic 19th-century houses in the Chaplin Historic District. The crime risk in Chaplin is lower than the national average. For higher education, the University of Connecticut and Eastern Connecticut State University are less than 10 miles away. Outdoor activities abound with Edward Garrison Park, which includes a playground, baseball diamond, and disc golf course, as well as Hubbard Sanctuary and Agnes’ Pasture with nearly 2 miles of trails. Diana’s Pool, a popular spot along the Natchaug River, and Mansfield Hollow State Park, just over 5 miles away, offer additional recreational opportunities. Dining options in Chaplin include The Baker’s Dozen and Blondie’s Country Diner, while shopping needs are met in nearby Windham, about 7 miles away. Chaplin is accessible via State Route 198 and U.S. Route 6, with regional bus services and a park-and-ride lot available for commuters.

Learn more about living in Chaplin

Single Family Home Prices in Chaplin, CT

The median price for single family homes in Chaplin is $361,250, and there are 5 single family home listings available for sale.

Single Family Home Price Trends

Median Home Price $361,250	Median 3-Bedroom Home Price $357,500
Median 4-Bedroom Home Price $401,000	Median 5-Bedroom Home Price $480,600

How to Buy a Home How to Finance a Home How to Sell a Home

In Chaplin, there are currently 5 houses for sale, offering an array of options for potential buyers. With houses priced between $350,000 to $789,000, there's a range to accomodate every budget. As of July, 2026 the median home price in Chaplin is $359,900, while the average sale price is $373,735, offering insights into the local housing market. On average, houses spend 52 days listed before being sold. Whether you're searching for a single-family residence, exploring single-family detached houses for sale, or considering new construction houses for sale, there are options to cater to different lifestyles. Explore the listings and houses for sale in Chaplin, CT and find the perfect place to call home.

Chaplin Types of Homes for Sale

More About Living in Chaplin

Single-family Homes for Sale in Nearby Cities

Single-family Homes for Sale in Nearby Counties

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