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Chaplin, CT Homes for Sale

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  • /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,

    Agent Photo

    Amy Rio

    Better Homes and Gardens Real Estate Executive Real Estate

    (860) 374-6602

    287 S Bear Hill Rd, Chaplin, CT 06235
  • /36

    $449,900

    • 5 Beds
    • 2.5 Baths
    • 2,887 Sq Ft

    13 Bates Rd, Chaplin, CT 06235

    Spacious farmhouse living at its best! This charming 5-bedroom, 2 full bath, and 1 half bath home sits on an expansive 11 acres, offering endless possibilities for privacy, recreation, or hobby farming. Inside, you'll find hardwood flooring throughout and two cozy fireplaces that add warmth and character. The versatile layout includes two additional family rooms that could easily serve as extra

    Kristen Merrill Countryside Realty

    13 Bates Rd, Chaplin, CT 06235
  • /2

    $335,000

    • Land
    • 62.27 Acres
    • $5,380 per Acre

    0 Scotland Rd Unit 24160798, Chaplin, CT 06235

    **Builders Take Notice** This is a beautiful 62.273 acres with subdivision opportunities. A-2 Survey is available. Owner financing is available.

    Sherry Borgeson Berkshire Hathaway NE Prop.

    0 Scotland Rd Unit 24160798, 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
  • /15

    $149,999

    • 3 Beds
    • 1 Bath
    • 1,204 Sq Ft

    137 Boulevard Rd, North Windham, CT 06256

    Tucked away on .63 private acres, this unique property offers endless possibilities for those seeking peace, privacy, and room to roam. The two-bedroom mobile home sits on its own land surrounded by nature. Enjoy open space conveniently located while still offering a secluded feel, this property is ideal for outdoor enthusiasts, investors, or anyone looking to escape the hustle and bustle.

    Antonio Incontro Countryside Realty

    137 Boulevard Rd, North Windham, CT 06256
  • /29

    $449,900

    Open Sat 12PM - 2PM
    • 3 Beds
    • 1.5 Baths
    • 1,596 Sq Ft

    36 Mount Hope Rd, Mansfield Center, CT 06250

    Beautifully remodeled ranch offering desirable one-floor living on a scenic road in Mansfield. This impressive home features an open floor plan, a gourmet kitchen with high-end upgrades, hardwood floors, modern lighting, stunning trim work, and large windows that bring in abundant natural light. Offering 3 bedrooms plus an office/guest room, this home combines comfort and functionality

    Blanca Vasallo eXp Realty

    36 Mount Hope Rd, Mansfield Center, CT 06250

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.

Frequently Asked Questions

What is the average home price in Chaplin, CT?
Homes for sale in Chaplin, CT have an average home price of $397,120.
How many homes have sold over the last 12 months in Chaplin, CT?
29 homes have sold in Chaplin, CT over the last 12 months.
What are the most popular zip codes in Chaplin, CT?
The most popular zip codes in Chaplin, CT include 06235, 06250, 06247, 06256 and 06268.
How much do you need to make to afford a house in Chaplin?
The median home price in Chaplin is $364,900. If you put a 20% down payment of $73,000 and had a 30-year fixed mortgage with an interest rate of 6.48%, your estimated principal and interest payment would be $1,840 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $79K a year to afford the median home price in Chaplin. Learn how much home you can afford with our Home Affordability Calculator.
How are the schools in Chaplin, CT?
Chaplin, CT has highly rated public and private schools. Some of the best schools in Chaplin based on Niche Grades are E.O. Smith High School, Ashford School and Chaplin Elementary School. Browse all the schools in Chaplin, CT to learn more.

Home Prices in Chaplin, CT

Home Price Trends

Median Sale Price
$357,500
Median Single Family Sale Price
$365,000
Median Townhouse Sale Price
$442,000
Median 2 Bedroom Sale Price
$310,000
Average Price Per Sq Ft
$242
Number of Homes for Sale
5
Last 12 months Home Sales
29
Months of Supply
2.10
Median List Price
$364,900
Median Change From 1st List Price
-2%
Median Home Sale Price YoY Change
4%
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