Chaplin Homes for Sale

Welcome to Chaplin, Connecticut – a hidden gem nestled in the heart of Windham County. This charming town, steeped in rich history and surrounded by picturesque landscapes, offers a unique blend of rural tranquility and modern conveniences. With its quaint New England charm, Chaplin is the perfect place for those seeking a peaceful lifestyle without sacrificing accessibility to larger urban areas.

Chaplin boasts a vibrant community spirit, with friendly neighbors and local events that bring residents together throughout the year. Enjoy the beauty of nature with numerous parks and recreational spaces, perfect for hiking, picnicking, or simply soaking in the serene surroundings. The town is also home to several historical sites that tell the story of its early settlers, making it a delightful destination for history enthusiasts.

For those looking to make Chaplin their home, you’re in luck! The real estate market here is thriving, with a variety of homes for sale that cater to diverse tastes and budgets. Whether you’re searching for a charming colonial, a cozy cottage, or a spacious family home, Chaplin has something to offer everyone. The properties often feature beautiful yards, modern amenities, and a sense of community that makes you feel right at home.

With its ideal location, friendly atmosphere, and a range of housing options, Chaplin is more than just a place to live; it’s a place to thrive. Explore the available homes for sale and discover the enchanting lifestyle that awaits you in this delightful Connecticut town!

Newest Chaplin Homes for Sale

$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

Start Your Search

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.