Chaplin Homes for Sale

Welcome to Chaplin, Connecticut – a hidden gem nestled in the heart of Windham County! This charming town offers a delightful blend of rural tranquility and community spirit, making it an ideal place for families, retirees, and anyone looking to embrace a slower pace of life. With its picturesque landscapes, friendly neighbors, and a rich history, Chaplin is a place where you can truly feel at home.

As you explore Chaplin, you’ll discover an array of outdoor activities that celebrate the town’s natural beauty. The area is dotted with scenic parks, hiking trails, and serene lakes, perfect for those who enjoy the great outdoors. Additionally, the town hosts a variety of local events throughout the year, fostering a strong sense of community and connection among residents.

For those considering a move, Chaplin offers a diverse selection of homes for sale. Whether you’re searching for a cozy cottage, a spacious family home, or a charming historic property, you’ll find a range of options to suit your needs. The real estate market in Chaplin is characterized by value and opportunity, making it an attractive choice for first-time homebuyers and seasoned investors alike.

With easy access to major highways, you’re never far from the amenities of larger towns while still enjoying the peace and quiet of small-town living. Explore Chaplin today, and discover the perfect place to call home in this idyllic corner of Connecticut!

Newest Chaplin Homes for Sale

$469,900

3 Beds ⋅ 2 Baths ⋅ 24214543 MLS

-Step back in time and experience the timeless charm of this distinctive antique brick Colonial, set on approximately 3 acres of beautifully cultivated grounds. Blending historic character with thoughtful modern updates, this 3-bedroom, 2-full-bath home offers inviting living spaces, multiple fireplaces, and an exceptional chef's kitchen featuring an oversized island, stone countertops, new appliances, a large basin sink, and a convenient pantry. The kitchen overlooks the spectacular outdoor setting, where nearly 1,100 square feet of newly laid bluestone patio provides the perfect backdrop for entertaining, outdoor dining, or simply enjoying the surrounding gardens. The main level also features a bedroom, full bathroom, additional sitting room or formal dining room, and a grand living room rich with character. Upstairs, two generously sized bedrooms include a walk-in closet and dressing room, with an additional full bathroom completing the second floor. Modern comforts include Mitsubishi heating and cooling splits, a main-level pellet stove, and a high-end Biasi B10 Series boiler. The grounds are equally impressive, offering a thoughtfully established homestead with seven apple trees, three plum trees, two cherry trees, two peach trees, two fig trees, established hydrangeas, perennial flower gardens, specialty ornamental trees, and three large garden areas, all enhanced by beautiful stone walls. A partially unfinished rear section currently used for storage adds a

15 Chaplin St, Chaplin

$150,000

2 Beds ⋅ 2 Baths ⋅ 24214247 MLS

Great opportunity for this 2 bedroom, 1.5 bath mobile home situated on over 3 acres. Highlights include a beautiful 3 Bay Carriage Shed with power and 2023 roof, screened rear porch, and 2021 roof on home. Secluded and set on a private road, away from traffic, yet minutes to shopping and dining. This home is being sold As Is, some TLC is needed.

32 Hall Rd, Chaplin

$450,000

3 Beds ⋅ 2 Baths ⋅ 24213283 MLS

Discover the perfect blend of comfort, style, and functionality in this beautifully updated Cape-style home! Offering three spacious bedrooms and two full bathrooms, this property features an inviting layout with thoughtful upgrades throughout. The stunning kitchen showcases granite countertops and beautiful finishes, complemented by hardwood flooring that adds warmth and character to the home. A dedicated dining room provides the perfect setting for gatherings, while the convenience of first-floor laundry makes everyday living a breeze. Additional highlights include a newer furnace, hot water tank, and central air conditioning. Outside, enjoy a welcoming front porch, a spacious, level backyard ideal for entertaining or relaxing, and an oversized detached garage equipped with electricity. With its combination of modern updates, classic charm, and versatile living spaces, this home is ready for its next chapter!

20 Park Dr, Chaplin

$525,000

5 Beds ⋅ 4 Baths ⋅ 24198620 MLS

Set on nearly 4 private acres, 21 Linkkila Lane offers the space, flexibility, and peaceful setting that make country living feel special. Start your morning with coffee on the deck while taking in the surrounding landscape and watching the horses at the neighboring horse farm. Inside, this beautifully updated log home strikes the perfect balance between cozy character and clean, modern updates. An abundance of natural light keeps the home feeling bright and airy, while wide plank floors add warmth and charm throughout. A gorgeous brick fireplace anchors the living room, creating an inviting gathering space. The main house features 3 spacious bedrooms, 3 full bathrooms, an extensively renovated kitchen, updated baths, new windows throughout, and a spacious walk-in pantry. Screened-in porches along the back offer additional space to relax and enjoy the peaceful surroundings. A separate in-law suite adds even more versatility with its own kitchen, 2 bedrooms, full bathroom, and separate utilities. Recent improvements include 2 updated kitchens, 4 renovated full bathrooms, new windows in 2025, 2 new water heaters, and refinished decks in 2026. A partially finished basement provides additional usable space and storage. Conveniently located near local schools, UConn, Eastern Connecticut State University, and surrounding towns, this home offers a unique combination of privacy, character, modern comfort, and flexible living.

21 Linkkila Ln, Chaplin

$369,900

3 Beds ⋅ 1 Baths ⋅ 24188389 MLS

Step into a beautifully restored piece of history with this enchanting 1830s home, nestled on a serene, private acre featuring a sprawling backyard complete with a tranquil babbling brook. This property captures the balance of historic character and modern ease. The main level offers a sun-drenched layout with a convenient primary bedroom featuring a brand-new floor, and a fully renovated bathroom with new framing and subfloor. A cozy wood stove serves as the heart of the home, while upstairs, a thoughtfully remodeled space adds to the bright, refreshed aesthetic. Extensively updated for worry-free living, this residence boasts updated electrical and plumbing systems, a new well system, and an efficient mini-split ductless system. As a result of a recent home inspection, the seller is upgrading the septic system by installing a brand-new septic tank and adding a UV light filtration system for the well. Modern conveniences-from new appliances and lighting to fresh carpeting-blend seamlessly with the home's original spirit. The exterior impresses with a new roof on both the home and garage, a rebuilt deck off the primary bedroom, and charming curb appeal. A rare opportunity to own a meticulously cared-for historic home in a tranquil country setting.

288 Bedlam Rd, Chaplin

$399,900

5 Beds ⋅ 3 Baths ⋅ 24179982 MLS

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 bedrooms, a home office, playroom, gym, or guest space - perfect for today's flexible lifestyle needs. Tucked away in a truly special setting, this home is surrounded by federal land, offering direct access to scenic hiking and horseback riding trails just steps from your door. Enjoy the peace and privacy of nature while still having the convenience of recent updates, including a newer boiler and porch. A seldom-available gem with room to grow both inside and out! Enjoy the space, charm, and opportunity this beautiful property provides with peaceful surroundings while still being in close proximity to Mansfield Hollow State Park, as well as nearby shopping and dining options. A rare opportunity to own acreage, space, and convenience all in one - schedule your showing today!

13 Bates Rd, Chaplin

Start Your Search

IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but is not guaranteed. © 2026 State-Wide Multiple Listing Service. All rights reserved. Data Last Updated:

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.

Chaplin Homes for Sale

Newest Chaplin Homes for Sale

How much is your home worth?

How much is your home worth?