Chaplin CT Real Estate

287 South Bear Hill Road Chaplin CT 06235

Chaplin, CT287 South Bear Hill Road

Price$789,000

Est. Mortgage: $/month

MLS Number 24175652

  • Single Family
  • Square Feet 2,900
  • Bedrooms 4
  • Bathroom 3
  • Year Built 1997

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.

Listed by Amy P. Rio of Better Homes and Gardens Real Estate Executive Real Estate

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$/month over payments
Federal 30-year interest rate: 6.49% last updated on Jun 25, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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21 Linkkila Lane Chaplin CT 06235

Chaplin, CT21 Linkkila Lane

Price$599,000

Est. Mortgage: $/month

MLS Number 24187395

  • Multi Family Multi-Family For Sale
  • Square Feet 2,220
  • Acreage 3.78
  • Bedrooms 5
  • Bathroom 4

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

Listed by Derek Greene of Derek Greene

$
$
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$/month over payments
Federal 30-year interest rate: 6.49% last updated on Jun 25, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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203 Willimantic Road Chaplin CT 06235

Chaplin, CT203 Willimantic Road

Price$495,000

Est. Mortgage: $/month

MLS Number 24168086

  • Single Family
  • Square Feet 1,504
  • Bedrooms 3
  • Bathroom 2
  • Year Built 1935

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

Listed by Sherry Borgeson of Berkshire Hathaway NE Prop.

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$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Jun 25, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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7-9 Bates Road Chaplin CT 06235

Chaplin, CT7-9 Bates Road

Price$434,000

Est. Mortgage: $/month

MLS Number 24171082

  • Single Family
  • Square Feet 3,522
  • Bedrooms 4
  • Bathroom 4
  • Year Built 1800

Step back in time while enjoying modern comforts in this charming 1800s Colonial offering 10 spacious rooms filled with character and natural light. The eat-in kitchen features an original butler's pantry, while the formal dining room and inviting living room each showcase stunning stone fireplaces-both complete with rare beehive ovens. French doors lead from the living room to a beautiful three-season porch, perfect for relaxing or entertaining. Generously sized rooms and abundant windows create a bright, airy feel throughout, complemented by hardwood floors in every room. Updated bathrooms blend seamlessly with the home's historic charm.A standout feature of this property is the separate guest house, offering incredible flexibility. It includes 2 bedrooms, a full bath with washer and dryer, a kitchen, and a living room that opens to its own three-season porch-ideal for rental income, in-law living, or private guest accommodations.Additional highlights include a 2-car garage with extra space above, double oil tanks, generator hookup, and separate electrical services and septic systems for each dwelling.Situated on nearly a level acre, this property offers both space and convenience-just 2 miles from Windham Center, 3 miles from Mansfield Hollow, 7 miles to UConn, and 4.4 miles to Eastern Connecticut State University.A rare opportunity to own a piece of history with income potential in a prime location.

Listed by Emily A. Turker of Berkshire Hathaway NE Prop.

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$
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$/month over payments
Federal 30-year interest rate: 6.49% last updated on Jun 25, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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222 Tower Hill Road Chaplin CT 06235

Chaplin, CT222 Tower Hill Road

Price$389,900

Est. Mortgage: $/month

MLS Number 24178626

  • Single Family
  • Square Feet 1,610
  • Bedrooms 3
  • Bathroom 2
  • Year Built 1994

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.

Listed by Lisa M. Therecka of Therecka & Associates LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Jun 25, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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288 Bedlam Road Chaplin CT 06235

MLS Number 24183986

  • Single Family
  • Square Feet 1,710
  • Bedrooms 3
  • Bathroom 1
  • Year Built 1830

Step into timeless charm with modern peace of mind in this beautifully restored 1830 home, set on a serene 1 acre country lot. This thoughtfully renovated 3 bedroom, 1 bath home blends historic character with today's most important updates. The flexible layout offers a first floor primary bedroom and full bath for easy living. Inside, enjoy a fully refreshed interior featuring a complete bathroom gut renovation with new framing and subfloor, a fully remodeled second floor, new carpeting, and all new lighting throughout. Major systems were extensively upgraded in 2024, including nearly all updated electrical, all new plumbing, a mini-split ductless system, and a new well system with pump, piping, wiring, and tank. The septic top was also replaced for added peace of mind. Cozy up with the new wood stove and Class A chimney system, professionally serviced annually. The home also includes new appliances and a recently serviced HVAC system. Exterior updates shine with a new roof on the home (2025) and garage, rebuilt primary bedroom deck, brick mailbox, updated well surround and cover, and landscape lighting, all completed in 2026. Blink security cameras add convenience and security. A rare opportunity to own a piece of history with modern upgrades, and virtually no maintenance for years to come. Don't miss your chance to call this one of a kind property your new home!

Listed by Natascia Klimas of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Jun 25, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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60 Chaplin Street Chaplin CT 06235

Chaplin, CT60 Chaplin Street

Price$350,000

Est. Mortgage: $/month

MLS Number 24160862

  • Single Family
  • Square Feet 2,438
  • Bedrooms 3
  • Bathroom 2
  • Year Built 1837

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

Listed by Stephen Daly of KW Legacy Partners

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Jun 25, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Scotland Road Chaplin CT 06235

Chaplin, CTScotland Road

Price$335,000

Est. Mortgage: $/month

MLS Number 24160798

  • Land
  • Acreage 62.27
  • MLS Status Active
  • Other Amenities Waterfront
  • Zoning RA

**Builders Take Notice** This is a beautiful 62.273 acres with subdivision opportunities. A-2 Survey is available. Owner financing is available.

Listed by Sherry Borgeson of Berkshire Hathaway NE Prop.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Jun 25, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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