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

$279,900

3 Beds ⋅ 2 Baths ⋅ 24201681 MLS

Welcome to this 7 room, 2 bath, ranch style home, with a detached garage, located on 2 Acres. set back off the road. If you have been looking for country living, this may be your home. Fully applianced kitchen (laundry set-up conveniently located), Kitchen eating nook, plus a formal dining room. All located on one floor living. Bring your ideas. lots of potential to make it your own.

337 Hampton Rd, Chaplin

$345,000

3 Beds ⋅ 2 Baths ⋅ 24203541 MLS

* Highest & Best Deadline Monday 7th @ 12PM * Cape charm meets country calm! This newly updated 3-bedroom, 2-full-bath Cape sits on 2 acres of flat, usable land, offering plenty of room to spread out and enjoy the peaceful setting. The main level features a bedroom and full bath, a bright living space, designated dining room, and an inviting back deck overlooking the beautiful yard. Upstairs offers two additional bedrooms and a second full bath. Major updates bring added peace of mind, with plumbing, electrical, and heat pump all approximately 5 years young. A spacious 12x40 shed provides incredible storage, workspace, or hobby potential. Updated, peaceful, and packed with possibilities-this Cape is ready to welcome you home!

254 Lynch Rd, Chaplin

$399,900

3 Beds ⋅ 2 Baths ⋅ 24202915 MLS

Love Country Living? This is the one for you! Sit out on your porch or deck at night and listen to the wildlife around you. Peaceful doesn't even begin to describe this home. Gather everyone for the holidays in this generous open floor plan complete with a floor to ceiling fireplace. Your main bedroom has its own full bath and laundry area. Home also features all new carpet, paint and a very new metal roof with a transferrable warranty. Basement is a walk out to the quiet backyard as well as through the garage. Don't miss this one! Call now to make an appointment for a private showing. Showings start Sept 3rd

407 N Bear Hill Rd, Chaplin

$550,000

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

$425,000

3 Beds ⋅ 3 Baths ⋅ 24198054 MLS

Welcome to 34 Cross Road, a beautifully maintained home offering the perfect blend of comfort, privacy, and timeless New England appeal. Set on over 2 acres in a serene, wooded setting, this 3-bedroom, 2.5-bath residence offers an inviting layout designed for both everyday living and entertaining. The main level welcomes you with a charming front porch entry and features a spacious living room, eat-in kitchen, formal dining room, and convenient half bath. Just off the main living spaces, the screened-in porch creates a peaceful retreat for morning coffee, summer evenings, or entertaining guests while enjoying the privacy of the surrounding landscape. Upstairs, the private primary suite offers its own full bath & walk in closet, complemented by two additional bedrooms and a second full bath providing flexibility for family, guests or a home office. An attached two-car garage adds everyday convenience and valuable storage. Outside, the expansive 2+ acre parcel provides plenty of space to enjoy nature and the tranquility of a private, wooded setting. Thoughtfully maintained and ideally suited for those seeking space, privacy, and classic Connecticut charm, 34 Cross Road is a special opportunity to make Chaplin home. (Home will be professionally cleaned this weekend. Carpets are dusty - not stained)

34 Cross Rd, 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. This property perfectly captures the balance of historic character and modern ease, offering a warm, welcoming retreat from the everyday. The main level features a flexible, sun-drenched layout highlighted by a convenient primary bedroom and a fully renovated bathroom with new framing and subfloor for peace of mind. A cozy wood stove serves as the heart of the home, creating an inviting atmosphere for both relaxed evenings and intimate gatherings. Upstairs, you will find a thoughtfully remodeled space that adds to the home's bright, refreshed aesthetic. Extensively updated for worry-free living, this residence boasts significant mechanical improvements, including updated electrical and plumbing systems, a new well system, and an efficient mini-split ductless system. Modern conveniences-from new appliances and lighting to fresh carpeting-blend seamlessly with the home's original spirit. The exterior is equally impressive, featuring a new roof on both the home and garage, a rebuilt deck off the primary bedroom, and charming curb appeal with a brick mailbox and landscape lighting. This is a rare opportunity to own a meticulously cared-for home that offers the best of both worlds: the soul of a historic property and the comfort of modern upgrades, all in a tranquil country setting.

288 Bedlam Rd, Chaplin

$419,900

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

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