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: 6.51% last updated on May 21, 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$595,000

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: 6.51% last updated on May 21, 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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13 Bates Road Chaplin CT 06235

Chaplin, CT13 Bates Road

Price$499,900

Est. Mortgage: $/month

MLS Number 24155072

  • Single Family
  • Square Feet 2,887
  • Bedrooms 5
  • Bathroom 3
  • Year Built 1840

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!

Listed by Kristen E. Merrill of Countryside Realty

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$
%
$/month over payments
Federal 30-year interest rate: 6.51% last updated on May 21, 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$444,000

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.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.51% last updated on May 21, 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: 6.51% last updated on May 21, 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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Chaplin CT 06235

Chaplin, CT

Price$299,000

Est. Mortgage: $/month

Coming Soon

Listing Number X14852091

  • Exclusive Residential
  • Sale or Lease for sale

Coming Soon!  An expansive Antique cape with 2423 square feet. First floor bedroom and Full bath. Many recent Updates including the kitchen and detached work shop.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.51% last updated on May 21, 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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Hampton Road Chaplin CT 06235

Chaplin, CTHampton Road

Price$139,000

Est. Mortgage: $/month

MLS Number 170523717

  • Land
  • Acreage 12.1
  • MLS Status Active
  • Other Amenities Waterfront
  • Zoning RA

12.1 acre lot with frontage on Route 6 and Cross Road. Button Ball Brook runs through property. Could be a great home site, or potential commercial development with zone change. Rolling hills of gravel, mostly wooded.

Listed by David Mieczynski of National Realty Advisors LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.51% last updated on May 21, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

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