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

$599,000

5 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24194145 MLS

Private Country Retreat with In-Law Suite on Nearly 4 Acres. Welcome to 21 Linkkila Lane in Chaplin, Windham County, Connecticut-a beautifully updated log home offering exceptional privacy, flexible living space, and modern upgrades on nearly four picturesque acres. The main residence features three spacious bedrooms and three full bathrooms, highlighted by an extensively renovated kitchen, updated bathrooms, and new windows throughout the home. Warm wood finishes, abundant natural light, and a propane stove create a welcoming atmosphere, while a fuel oil boiler provides efficient baseboard and radiant heat throughout much of the home. Perfect for multi-generational living or extended guests, the property also includes a fully equipped in-law suite complete with its own kitchen, full-bathroom, and two bedrooms. Includes separate utilities. Recent improvements include:* 2 beautifully updated kitchens* 4 renovated full bathrooms* New windows throughout the entire home (2025)* 2 new water heaters* Refinished decks (2026)* Partially finished basement* Nearly 4 private acres* Peaceful country setting on a quiet dead-end lane. Local Schools Chaplin Elementary: ~7 mins Parish Hill Middle/High: ~6 mins Mansfield Elementary: ~5 mins University of Connecticut (UConn), Storrs: ~12minEastern Connecticut State University (ECSU): ~13minAirports and Travel Bradley Intl Airport (BDL): ~50 mins Rhode Island T.F. Green Intl Airport (PVD): ~1hr. See also MLS # 24187395

21 Linkkila Ln, Chaplin

$350,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24160862 MLS

Welcome to place where time truly is the most beautiful thing. There is a particular kind of feeling when you walk through a historic door like this. Maybe it's the hardwood plank floors that have held two centuries of footsteps. Maybe it's the way the morning light hits the windows on every home on Chaplin Street, a village so notable it's listed on the National Register of Historic Places. Maybe it's the quiet and peace that magically flows through a home like this. Built in 1837 as the town parsonage, this home has been part of this community's story for nearly 200 years. Now it's looking for someone ready to write the next chapter. 11 rooms await for the exciting next chapter. The big work is already done. New roof. New electrical panel. Foundation fully repointed with fresh mortar, inside and out. Chimney repointed and stuccoed, New stainless steel liner, crown, and cap installed. What's left to do is the part that lets the new owner make it their own: cosmetic updates, with flooring quotes already in hand for new carpet and refinished hardwood. Set on nearly an acre of flat, open land, this is the kind of property that rewards patience and vision. For the history lover who's been waiting for a home with a past worth preserving, the hands-on owner who sees potential where others see projects, or the investor eyeing the space and the location near UConn and ECSU, this one is worth it all. Come and see what was once part of the past and how it can be a part of your future

60 Chaplin St, Chaplin

$429,900

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

$389,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24178626 MLS

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 private in-law apartment with its own separate entrance - ideal for guests, extended family, or potential rental income. Enjoy peaceful outdoor living with a private bedroom balcony, an oversized upper deck off the kitchen, a lower-level deck, and access to the beautiful Stone House Brook. Additional highlights include a long circular driveway and Two outbuildings offering exceptional storage and endless possibilities. A truly special countryside retreat with warmth, charm, and flexibility throughout.

222 Tower Hill Rd, Chaplin

$789,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24175652 MLS

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, kennels, or hobby farming. The property also includes a chicken coop, goat building, fenced garden with 12 raised beds, pond, two running streams, and a fire pit area. Inside, the home has been extensively updated with a stunning mahogany entry, Brazilian Walnut (IPE) flooring, vaulted ceilings, fireplace, and a beautifully designed chef's kitchen with soapstone counters, custom cabinetry, and Bosch stainless appliances including an induction stove. The first-floor primary suite offers vaulted ceilings, two walk-in closets, and a renovated bath with porcelain tile and granite vanity. A sunroom with marble floors and skylights opens to the back deck, while a spacious bonus room with private entrance offers ideal in-law, office, or gym potential. Additional features include dual heat with Central Wood Boiler and oil backup, Kubota whole-house generator, underground utilities, central vac, artesian well, cedar siding, and gated driveway. A truly exceptional property with endless possibilities.

287 S Bear Hill Rd, Chaplin

$495,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24168086 MLS

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 heated sun porch, formerly used as the business office, now serves as a bright and versatile space. The first-floor primary bedroom adds convenience and features a cedar closet. The home has seen several important updates, including a new hot water heater (2023), water holding tank (2024), oil tank, and septic tank. The roof is approximately 10 years old, and double-pane replacement windows help improve overall efficiency. Enjoy a Trex deck. Adding to the appeal, the abutting land is protected by Joshua's Trust, preserving the natural surroundings and offering lasting privacy. An exceptionally deep detached garage (roof 9 yrs) provides plenty of space for storage, hobbies, or workshop use. With zoning that allows for both residential and commercial use, this property presents a rare opportunity to create the lifestyle you want-whether that's purely residential or incorporating a home-based business. Conveniently situated on Route 6 close to shopping, restaurants, and everyday conveniences, this is a truly distinctive offering with history, flexibility, and potential

203 Willimantic Rd, Chaplin

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