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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.

4 Beds ⋅ 3 Baths ⋅ 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

$580,000

Step into history with this beautifully updated antique Colonial, originally built in 1785, offering timeless charm with modern updates throughout. A standout feature is the fully equipped in-law suite, complete with its own kitchen, living room, bedroom, full bathroom, and washer/dryer- perfect for multigenerational living, guests, or potential rental income. The property also features a new detached 2 car garage, an insulated barn with electricity, and an additional large barn with newer roof ready for your finishing touches. Enjoy the peaceful setting surrounded by non-buildable land and scenic river views from your back porch.

5 Beds ⋅ 4 Baths ⋅ 24161631 MLS

Step into history with this beautifully updated antique Colonial, originally built in 1785, offering timeless charm with modern updates throughout. A standout feature is the fully equipped in-law suite, complete with its own kitchen, living room, bedroom, full bathroom, and washer/dryer- perfect for multigenerational living, guests, or potential rental income. The property also features a new detached 2 car garage, an insulated barn with electricity, and an additional large barn with newer roof ready for your finishing touches. Enjoy the peaceful setting surrounded by non-buildable land and scenic river views from your back porch.

18 Bates Rd, Chaplin

$470,000

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.

4 Beds ⋅ 4 Baths ⋅ 24171082 MLS

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.

7-9 Bates Rd, Chaplin

$420,000

Welcome to 34 Cross Road, a beautifully maintained home offering the perfect blend of comfort, privacy, and timeless New England appeal. Set on over 2 acres in a serene, wooded setting, this 3-bedroom, 2.5-bath residence offers an inviting layout designed for both everyday living and entertaining. The main level welcomes you with a charming front porch entry and features a spacious living room, eat-in kitchen, formal dining room, and convenient half bath. Just off the main living spaces, the screened-in porch creates a peaceful retreat for morning coffee, summer evenings, or entertaining guests while enjoying the privacy of the surrounding landscape. Upstairs, the private primary suite offers its own full bath & walk in closet, complemented by two additional bedrooms and a second full bath providing flexibility for family, guests or a home office. An attached two-car garage adds everyday convenience and valuable storage. Outside, the expansive 2+ acre parcel provides plenty of space to enjoy nature and the tranquility of a private, wooded setting. Thoughtfully maintained and ideally suited for those seeking space, privacy, and classic Connecticut charm, 34 Cross Road is a special opportunity to make Chaplin home. (Home will be professionally cleaned this weekend. Carpets are dusty - not stained)

3 Beds ⋅ 3 Baths ⋅ 24198054 MLS

Welcome to 34 Cross Road, a beautifully maintained home offering the perfect blend of comfort, privacy, and timeless New England appeal. Set on over 2 acres in a serene, wooded setting, this 3-bedroom, 2.5-bath residence offers an inviting layout designed for both everyday living and entertaining. The main level welcomes you with a charming front porch entry and features a spacious living room, eat-in kitchen, formal dining room, and convenient half bath. Just off the main living spaces, the screened-in porch creates a peaceful retreat for morning coffee, summer evenings, or entertaining guests while enjoying the privacy of the surrounding landscape. Upstairs, the private primary suite offers its own full bath & walk in closet, complemented by two additional bedrooms and a second full bath providing flexibility for family, guests or a home office. An attached two-car garage adds everyday convenience and valuable storage. Outside, the expansive 2+ acre parcel provides plenty of space to enjoy nature and the tranquility of a private, wooded setting. Thoughtfully maintained and ideally suited for those seeking space, privacy, and classic Connecticut charm, 34 Cross Road is a special opportunity to make Chaplin home. (Home will be professionally cleaned this weekend. Carpets are dusty - not stained)

34 Cross Rd, Chaplin

$420,000

Country Roads, Take Me Home! Tucked away in a peaceful setting just a short walk to downtown Chaplin Village, this unique and charming antique home blends historic character with surprisingly spacious, light-filled living. Oversized rooms, hardwood floors, and abundant built-ins showcase the home's timeless appeal, while the flexible layout offers endless possibilities. The inviting country-style eat-in kitchen is the heart of the home, complemented by a large den/sitting room or possible dining room, perfect for gatherings, along with a warm and welcoming living room filled with antique charm. A first-floor primary bedroom adds convenience, while the expansive rear addition offers incredible versatility - ideal for a luxurious primary suite, in-law setup, or an impressive great room. Outside, enjoy 2.9 acres of peaceful Chaplin charm featuring beautiful stone walls, a relaxing back patio, and a workshop with 50-amp service. Full of warmth, history, and opportunity, this special property is ready to welcome you home.

3 Beds ⋅ 2 Baths ⋅ 24178105 MLS

Country Roads, Take Me Home! Tucked away in a peaceful setting just a short walk to downtown Chaplin Village, this unique and charming antique home blends historic character with surprisingly spacious, light-filled living. Oversized rooms, hardwood floors, and abundant built-ins showcase the home's timeless appeal, while the flexible layout offers endless possibilities. The inviting country-style eat-in kitchen is the heart of the home, complemented by a large den/sitting room or possible dining room, perfect for gatherings, along with a warm and welcoming living room filled with antique charm. A first-floor primary bedroom adds convenience, while the expansive rear addition offers incredible versatility - ideal for a luxurious primary suite, in-law setup, or an impressive great room. Outside, enjoy 2.9 acres of peaceful Chaplin charm featuring beautiful stone walls, a relaxing back patio, and a workshop with 50-amp service. Full of warmth, history, and opportunity, this special property is ready to welcome you home.

58 Tower Hill Rd, Chaplin

$400,000

Calling all nature enthusiasts and outdoorsmen! A true "Quiet Corner" awaits on this peaceful 6.2 acre paradise. Surrounded by nature at the end of a country road. This property is adjacent to over 200 acres of preserved land. Natchaug State Forest ,"Two Sisters Preserve", "Airline Trails" all provide miles of beautiful hiking trails amongst acres of forest and streams. While very private and surrounded by nature the property is conveniently located only15 minutes from UConn, close to Rte 6 and shopping. This home is a solid built ranch. Many big ticket items have been addressed 200 amp electric, generator ready with new generator, oversized detached garage with power. New septic system. Sun-filled open layout with access to large Sunroom heated by wood stove, this room not included in the homes square footage. Kitchen with new appliances is open to a lovely living room with cozy fireplace and built-ins. Beautiful hardwood floors and freshly painted interior. Three bedrooms and a good size full bath complete this comfortable one floor living. Full walk out basement provides great potential for future additional living space. The recently reinforced and structurally sound West facing deck will be a favorite spot to relax, soak in the sites and sounds of nature during the day, watch mesmerizing evening sunsets followed by quiet star filled nights. A gardeners paradise, with unlimited potential awaits!

3 Beds ⋅ 1 Baths ⋅ 24179725 MLS

Calling all nature enthusiasts and outdoorsmen! A true "Quiet Corner" awaits on this peaceful 6.2 acre paradise. Surrounded by nature at the end of a country road. This property is adjacent to over 200 acres of preserved land. Natchaug State Forest ,"Two Sisters Preserve", "Airline Trails" all provide miles of beautiful hiking trails amongst acres of forest and streams. While very private and surrounded by nature the property is conveniently located only15 minutes from UConn, close to Rte 6 and shopping. This home is a solid built ranch. Many big ticket items have been addressed 200 amp electric, generator ready with new generator, oversized detached garage with power. New septic system. Sun-filled open layout with access to large Sunroom heated by wood stove, this room not included in the homes square footage. Kitchen with new appliances is open to a lovely living room with cozy fireplace and built-ins. Beautiful hardwood floors and freshly painted interior. Three bedrooms and a good size full bath complete this comfortable one floor living. Full walk out basement provides great potential for future additional living space. The recently reinforced and structurally sound West facing deck will be a favorite spot to relax, soak in the sites and sounds of nature during the day, watch mesmerizing evening sunsets followed by quiet star filled nights. A gardeners paradise, with unlimited potential awaits!

73 Bolduc Ln, Chaplin

$375,000

* Highest & Best Deadline Monday 7th @ 12PM * Cape charm meets country calm! This newly updated 3-bedroom, 2-full-bath Cape sits on 2 acres of flat, usable land, offering plenty of room to spread out and enjoy the peaceful setting. The main level features a bedroom and full bath, a bright living space, designated dining room, and an inviting back deck overlooking the beautiful yard. Upstairs offers two additional bedrooms and a second full bath. Major updates bring added peace of mind, with plumbing, electrical, and heat pump all approximately 5 years young. A spacious 12x40 shed provides incredible storage, workspace, or hobby potential. Updated, peaceful, and packed with possibilities-this Cape is ready to welcome you home!

3 Beds ⋅ 2 Baths ⋅ 24203541 MLS

* Highest & Best Deadline Monday 7th @ 12PM * Cape charm meets country calm! This newly updated 3-bedroom, 2-full-bath Cape sits on 2 acres of flat, usable land, offering plenty of room to spread out and enjoy the peaceful setting. The main level features a bedroom and full bath, a bright living space, designated dining room, and an inviting back deck overlooking the beautiful yard. Upstairs offers two additional bedrooms and a second full bath. Major updates bring added peace of mind, with plumbing, electrical, and heat pump all approximately 5 years young. A spacious 12x40 shed provides incredible storage, workspace, or hobby potential. Updated, peaceful, and packed with possibilities-this Cape is ready to welcome you home!

254 Lynch Rd, Chaplin

$352,500

Built in 2000, this well-maintained single-family home offers 3 bedrooms and 2 full bathrooms on 4 ACRES in Chaplin, CT with a peaceful BROOK view. The interior has been freshly painted and features a comfortable, move-in ready feel with updated flooring and carpet throughout. The home includes a newer heating system, central air conditioning throughout including the garage, washer and dryer on the main level, and a generator backup system for added peace of mind. The oversized 2-car garage offers high ceilings and 220V outlets, making it ideal for car enthusiasts, hobbyists, or additional workspace. A spacious deck overlooks the private surroundings, enhancing outdoor living and enjoyment of the natural setting. This property combines privacy, functionality, and modern comfort in a rare 4-acre Chaplin location. SHOWINGS START MONDAY APRIL 20TH 4PM-6PM

3 Beds ⋅ 2 Baths ⋅ 24168233 MLS

Built in 2000, this well-maintained single-family home offers 3 bedrooms and 2 full bathrooms on 4 ACRES in Chaplin, CT with a peaceful BROOK view. The interior has been freshly painted and features a comfortable, move-in ready feel with updated flooring and carpet throughout. The home includes a newer heating system, central air conditioning throughout including the garage, washer and dryer on the main level, and a generator backup system for added peace of mind. The oversized 2-car garage offers high ceilings and 220V outlets, making it ideal for car enthusiasts, hobbyists, or additional workspace. A spacious deck overlooks the private surroundings, enhancing outdoor living and enjoyment of the natural setting. This property combines privacy, functionality, and modern comfort in a rare 4-acre Chaplin location. SHOWINGS START MONDAY APRIL 20TH 4PM-6PM

164 Tower Hill Rd, Chaplin

$324,000

COUNTRY LIVING AT IT'S BEST!!! Rural setting, offering peace & privacy. Come see this rustic well maintained 2 bedroom home, offering endless possibilities. 2 additional rooms in basement could be used as workshop, office, gym, craft room or guest space. Expansive open yard with the natural beauty of a peaceful stream making it ready for gardening. complete with a garage, ample yard space for RV parking and outdoor storage. Make this unique property your own, using your imagination.

2 Beds ⋅ 1 Baths ⋅ 24168977 MLS

COUNTRY LIVING AT IT'S BEST!!! Rural setting, offering peace & privacy. Come see this rustic well maintained 2 bedroom home, offering endless possibilities. 2 additional rooms in basement could be used as workshop, office, gym, craft room or guest space. Expansive open yard with the natural beauty of a peaceful stream making it ready for gardening. complete with a garage, ample yard space for RV parking and outdoor storage. Make this unique property your own, using your imagination.

4 Cross Rd, Chaplin

$300,000

What an opportunity with this home. Cape that sits on 3.85 acres sits up on a hill with great views. Great opportunity for expansion, 2nd floor is not finished so home could be 4 bedrooms with 2 full bath. Main level offers two bedrooms with a full bath. Living room with wood stove to help keep the heating costs down. Large kitchen with eat in area that can hold a large table, sliders to back yard, Breakfast bar area. Home needs some TLC. Full Bath on main level has some mold, Lower level also could be finished for more space. Newer Furnace, this home has so much to offer. Yard needs some TLC too but offers nice garden areas with stone walls. Talked to Eastern Highlands about adding the bedrooms there is a 1000-gallon septic tank now and they said you would have to ask for a public health review to make sure there is a reserve area. Manfield Hollow State Park and walking trails close by. HIGHEST AND BEST DUE BY 4-1-26 AT NOON

2 Beds ⋅ 1 Baths ⋅ 24161871 MLS

What an opportunity with this home. Cape that sits on 3.85 acres sits up on a hill with great views. Great opportunity for expansion, 2nd floor is not finished so home could be 4 bedrooms with 2 full bath. Main level offers two bedrooms with a full bath. Living room with wood stove to help keep the heating costs down. Large kitchen with eat in area that can hold a large table, sliders to back yard, Breakfast bar area. Home needs some TLC. Full Bath on main level has some mold, Lower level also could be finished for more space. Newer Furnace, this home has so much to offer. Yard needs some TLC too but offers nice garden areas with stone walls. Talked to Eastern Highlands about adding the bedrooms there is a 1000-gallon septic tank now and they said you would have to ask for a public health review to make sure there is a reserve area. Manfield Hollow State Park and walking trails close by. HIGHEST AND BEST DUE BY 4-1-26 AT NOON

11 Mountain Laurel Ln, Chaplin

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