Chaplin Real Estate

Welcome to Chaplin, Connecticut – a quaint and charming town nestled in the heart of Windham County. With its picturesque landscapes and rich history, Chaplin offers a unique blend of rural charm and modern conveniences, making it an ideal place to call home.

Founded in the early 18th century, Chaplin boasts a strong sense of community and a commitment to preserving its historical roots. The town is characterized by its rolling hills, lush forests, and serene lakes, providing residents with ample opportunities for outdoor recreation. Whether you enjoy hiking, fishing, or simply taking in the beauty of nature, Chaplin is a haven for nature enthusiasts.

One of Chaplin’s standout features is its commitment to maintaining a family-friendly atmosphere. With highly-rated schools and a variety of local events throughout the year, families can find a welcoming environment that fosters growth and connection. The town’s close-knit community often comes together for seasonal festivals, farmers' markets, and cultural events, creating a vibrant social landscape.

Convenience is another hallmark of Chaplin living. Located just a short drive from larger towns like Willimantic and Mansfield, residents can enjoy easy access to shopping, dining, and entertainment options while still relishing the tranquility of small-town life. Commuters will appreciate the proximity to major highways, making travel to Hartford and beyond a breeze.

In Chaplin, you’ll find not just a place to live, but a community to thrive in. Discover your new home in this hidden gem of Windham County, where every day feels like a breath of fresh air.

Newest Listings in Chaplin

$279,900

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 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

$550,000

5 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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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