Movetolitchfieldcounty.com Search Results

$433,000

Tucked away in a peaceful country setting just minutes from Winchester Center, this well-maintained 4-bedroom Colonial offers space, comfort, and timeless charm. Proudly owned by just one owner, this home reflects true pride of ownership throughout, with thoughtfully updated mechanicals and the added peace of mind of a whole-house generator. The inviting main level features a spacious family room with a cozy fireplace and slider leading to the outdoors-perfect for relaxing or entertaining. A warm and welcoming den showcases natural wood paneling and hardwood flooring, while the formal dining room is accented by classic pegged wood floors, adding character and elegance. The large eat-in kitchen offers ample space for gatherings and includes a convenient pantry. Upstairs, you'll find a generous primary suite complete with a private full bath, along with three additional bedrooms and another full bath, providing plenty of room for family and guests. Set on 2.76 lightly wooded acres, this property offers both privacy and a beautiful natural backdrop, making it the perfect place to call home. FINAL AND BEST IS DUE ON SUNDAY AT 3:00 PM

4 Beds ⋅ 3 Baths ⋅ 24167287 MLS

Tucked away in a peaceful country setting just minutes from Winchester Center, this well-maintained 4-bedroom Colonial offers space, comfort, and timeless charm. Proudly owned by just one owner, this home reflects true pride of ownership throughout, with thoughtfully updated mechanicals and the added peace of mind of a whole-house generator. The inviting main level features a spacious family room with a cozy fireplace and slider leading to the outdoors-perfect for relaxing or entertaining. A warm and welcoming den showcases natural wood paneling and hardwood flooring, while the formal dining room is accented by classic pegged wood floors, adding character and elegance. The large eat-in kitchen offers ample space for gatherings and includes a convenient pantry. Upstairs, you'll find a generous primary suite complete with a private full bath, along with three additional bedrooms and another full bath, providing plenty of room for family and guests. Set on 2.76 lightly wooded acres, this property offers both privacy and a beautiful natural backdrop, making it the perfect place to call home. FINAL AND BEST IS DUE ON SUNDAY AT 3:00 PM

118 South Rd, Winchester

$430,000

Open 10:30-12:30 Sunday 11/9/25. Motivated Seller! Seller financing available. A wonderful opportunity to own a mixed use property in the town center of Winsted. Currently used as a cleaner and tailoring shop on the first floor with an apartment on the second floor. Opportunity exists for the new owner to take over a turn key business with a strong existing client base and several commercial clients. The second floor offers the opportunity for a live in space, rental residential space with 3 bedrooms, a kitchen, living room and bathroom or the opportunity for office space. This building is located on a main road with great road frontage and a brand new freshly paved parking lot and some new siding on the building. The location offers an opportunity for a new owner to take over the existing business or completely start a new one in this prime location. Book your showing today.

1 Baths ⋅ 24112471 MLS

Open 10:30-12:30 Sunday 11/9/25. Motivated Seller! Seller financing available. A wonderful opportunity to own a mixed use property in the town center of Winsted. Currently used as a cleaner and tailoring shop on the first floor with an apartment on the second floor. Opportunity exists for the new owner to take over a turn key business with a strong existing client base and several commercial clients. The second floor offers the opportunity for a live in space, rental residential space with 3 bedrooms, a kitchen, living room and bathroom or the opportunity for office space. This building is located on a main road with great road frontage and a brand new freshly paved parking lot and some new siding on the building. The location offers an opportunity for a new owner to take over the existing business or completely start a new one in this prime location. Book your showing today.

57 Main St, Winchester

$425,000

Start your lakeside legacy at this rare waterfront cottage on Highland Lake. With stunning westerly views and a private dock, this is the perfect New England retreat for daily sunsets over the water. This intimate 512-square-foot home offers two bedrooms, a sunroom, Modern Eat-in Kitchen and a versatile loft space. with a newer roof, plumbing, electrical, and blown-in insulation, providing a low-maintenance opportunity to be ready QUICKLY for the next boating season! Highland Lake is a 445-acre reservoir in the Mountains, known for its recreational appeal. The lake is stocked annually, and it is designated a Trophy Trout and Bass Management Lake, making it an outstanding destination for anglers. Boating, swimming, and water skiing are among the many activities available, all within a community that values both recreation and tranquility. Don't miss the chance to own a piece of this serene, active, and beautiful lakeside community. Schedule a private tour today.

2 Beds ⋅ 1 Baths ⋅ 24121868 MLS

Start your lakeside legacy at this rare waterfront cottage on Highland Lake. With stunning westerly views and a private dock, this is the perfect New England retreat for daily sunsets over the water. This intimate 512-square-foot home offers two bedrooms, a sunroom, Modern Eat-in Kitchen and a versatile loft space. with a newer roof, plumbing, electrical, and blown-in insulation, providing a low-maintenance opportunity to be ready QUICKLY for the next boating season! Highland Lake is a 445-acre reservoir in the Mountains, known for its recreational appeal. The lake is stocked annually, and it is designated a Trophy Trout and Bass Management Lake, making it an outstanding destination for anglers. Boating, swimming, and water skiing are among the many activities available, all within a community that values both recreation and tranquility. Don't miss the chance to own a piece of this serene, active, and beautiful lakeside community. Schedule a private tour today.

548 E Wakefield Blvd, Winchester

$420,000

Welcome to 26 Elm Street, a newly renovated and legally converted three-family property in the heart of Winsted. This is a rare opportunity for investors or owner-occupants seeking a move-in-ready, income-producing asset with strong upside potential. Two of the units have been completely renovated, featuring updated interiors that appeal to today's tenants, while the exterior has also been recently improved, enhancing curb appeal and reducing near-term maintenance costs. The third unit provides additional income potential, making this a well-balanced investment with multiple revenue streams. The property has been legally converted to a 3-family, offering peace of mind and compliance for financing and long-term ownership. Prime Location & Rental Appeal Situated on Elm Street in Winsted, the property benefits from a convenient location close to downtown amenities, shopping, and dining. Easy access to commuter routes and nearby employment hubs helps drive consistent tenant demand. The area's small-town charm combined with accessibility makes it attractive for a wide range of renters. Strong Income Potential with two newly renovated units ready to command market rents and a third unit adding additional cash flow, this property is positioned for immediate income generation. Whether you're looking to expand your portfolio or live in one unit while renting the others, 26 Elm Street offers flexibility and solid returns.

5 Beds ⋅ 3 Baths ⋅ 24182777 MLS

Welcome to 26 Elm Street, a newly renovated and legally converted three-family property in the heart of Winsted. This is a rare opportunity for investors or owner-occupants seeking a move-in-ready, income-producing asset with strong upside potential. Two of the units have been completely renovated, featuring updated interiors that appeal to today's tenants, while the exterior has also been recently improved, enhancing curb appeal and reducing near-term maintenance costs. The third unit provides additional income potential, making this a well-balanced investment with multiple revenue streams. The property has been legally converted to a 3-family, offering peace of mind and compliance for financing and long-term ownership. Prime Location & Rental Appeal Situated on Elm Street in Winsted, the property benefits from a convenient location close to downtown amenities, shopping, and dining. Easy access to commuter routes and nearby employment hubs helps drive consistent tenant demand. The area's small-town charm combined with accessibility makes it attractive for a wide range of renters. Strong Income Potential with two newly renovated units ready to command market rents and a third unit adding additional cash flow, this property is positioned for immediate income generation. Whether you're looking to expand your portfolio or live in one unit while renting the others, 26 Elm Street offers flexibility and solid returns.

26 Elm St, Winchester

$420,000

In-Town Victorian 2-Family - Exceptional Condition & Versatility Rare opportunity to own a beautifully maintained, vinyl-sided Victorian-style side-by-side two-family home in a prime in-town location! This unique property offers incredible flexibility for investors, owner-occupants, or multi-generational living. Each unit features its own private entrance and spacious layout-one side offering a 2-bedroom apartment, the other a 3-bedroom apartment. Both units include 1.5 baths, updated kitchens with appliances, and tastefully renovated bathrooms. Gleaming hardwood floors run throughout, adding warmth and timeless character. Enjoy the charm of a classic wrap-around covered porch-perfect for relaxing or entertaining. The property also includes a detached 2-car garage and an additional shed for storage. Centrally located close to shopping, dining, schools, and major routes, this home is ideal as a strong rental investment or an in-law setup. Meticulously cared for and in extraordinary condition-this is a must-see property!

5 Beds ⋅ 4 Baths ⋅ 24168016 MLS

In-Town Victorian 2-Family - Exceptional Condition & Versatility Rare opportunity to own a beautifully maintained, vinyl-sided Victorian-style side-by-side two-family home in a prime in-town location! This unique property offers incredible flexibility for investors, owner-occupants, or multi-generational living. Each unit features its own private entrance and spacious layout-one side offering a 2-bedroom apartment, the other a 3-bedroom apartment. Both units include 1.5 baths, updated kitchens with appliances, and tastefully renovated bathrooms. Gleaming hardwood floors run throughout, adding warmth and timeless character. Enjoy the charm of a classic wrap-around covered porch-perfect for relaxing or entertaining. The property also includes a detached 2-car garage and an additional shed for storage. Centrally located close to shopping, dining, schools, and major routes, this home is ideal as a strong rental investment or an in-law setup. Meticulously cared for and in extraordinary condition-this is a must-see property!

217 Walnut St, Winchester

$410,000

Welcome to this spacious and well-maintained 2,196 sq. ft. one-owner home offering comfortable living in a convenient in-town location. This 3-bedroom, 2-bath residence features an open floor plan on the main living level, highlighted by a large formal living room with fireplace, dining room, expansive family room, and an updated kitchen-perfect for both everyday living and entertaining. Beautiful hardwood floors run throughout much of the home, adding warmth and character. The property sits on a generous level lot totaling approximately .70 acres, which includes an additional .04-acre garden lot. Updated windows throughout the home provide efficiency and natural light. Step outside to enjoy the covered patio overlooking the level and private rear yard-an ideal space for relaxing or hosting gatherings. Additional features include an attached two-car garage and a standby generator for added peace of mind. Conveniently located close to Routes 8 and 44 and just minutes from downtown shopping, dining, and everyday conveniences.

3 Beds ⋅ 2 Baths ⋅ 24157783 MLS

Welcome to this spacious and well-maintained 2,196 sq. ft. one-owner home offering comfortable living in a convenient in-town location. This 3-bedroom, 2-bath residence features an open floor plan on the main living level, highlighted by a large formal living room with fireplace, dining room, expansive family room, and an updated kitchen-perfect for both everyday living and entertaining. Beautiful hardwood floors run throughout much of the home, adding warmth and character. The property sits on a generous level lot totaling approximately .70 acres, which includes an additional .04-acre garden lot. Updated windows throughout the home provide efficiency and natural light. Step outside to enjoy the covered patio overlooking the level and private rear yard-an ideal space for relaxing or hosting gatherings. Additional features include an attached two-car garage and a standby generator for added peace of mind. Conveniently located close to Routes 8 and 44 and just minutes from downtown shopping, dining, and everyday conveniences.

35 Glendale Ave, Winchester

$400,000

Please submit your client's highest and best offer by Sunday 07/19 at 3:00 PM. Beautifully remodeled and move-in ready, 195 Reaching Hill Rd in Winsted, CT features modern updates, comfort, and functionality throughout. This 3-bedroom, 2-bath conventional-style home sits on nearly one acre of land and showcases a bright open-concept layout with beautiful hardwood floors, a spacious living area, and a dedicated dining space with large sliding glass doors overlooking the backyard. The main floor includes a bedroom and full bathroom, providing flexibility for a variety of uses such as a guest room, home office, or convenient one-level living arrangement. The finished lower level with a walk-out entrance and full basement adds valuable additional space with endless possibilities for a recreation room, home gym, playroom, workshop, or additional storage. Enjoy the comfort of central air conditioning, along with a relaxing porch, outdoor shed, and a private backyard with plenty of space to relax, garden, or entertain. Located near Highland Lake, this property provides convenient access to outdoor recreation throughout the seasons. With thoughtful renovations, spacious rooms, and a great indoor-outdoor connection, this home is ready for its next owner. Schedule your private showing today and see everything this beautifully updated Winsted property has to provide.

3 Beds ⋅ 2 Baths ⋅ 24190790 MLS

Please submit your client's highest and best offer by Sunday 07/19 at 3:00 PM. Beautifully remodeled and move-in ready, 195 Reaching Hill Rd in Winsted, CT features modern updates, comfort, and functionality throughout. This 3-bedroom, 2-bath conventional-style home sits on nearly one acre of land and showcases a bright open-concept layout with beautiful hardwood floors, a spacious living area, and a dedicated dining space with large sliding glass doors overlooking the backyard. The main floor includes a bedroom and full bathroom, providing flexibility for a variety of uses such as a guest room, home office, or convenient one-level living arrangement. The finished lower level with a walk-out entrance and full basement adds valuable additional space with endless possibilities for a recreation room, home gym, playroom, workshop, or additional storage. Enjoy the comfort of central air conditioning, along with a relaxing porch, outdoor shed, and a private backyard with plenty of space to relax, garden, or entertain. Located near Highland Lake, this property provides convenient access to outdoor recreation throughout the seasons. With thoughtful renovations, spacious rooms, and a great indoor-outdoor connection, this home is ready for its next owner. Schedule your private showing today and see everything this beautifully updated Winsted property has to provide.

195 Reaching Hill Rd, Winchester

$389,900

Here is your perfect chance to build your investment portfolio! 2 houses and a vacant lot create the perfect investment opportunity! Comprised of a 4 unit apartment building and a single unit house with a 4 car garage under and an adjacent vacant lot. The vacant lot is perfect for additional parking and or play area! All tenants have been there long term and pay regularly. Buyer and buyer agent to do own due diligence.

8 Beds ⋅ 5 Baths ⋅ 24121899 MLS

Here is your perfect chance to build your investment portfolio! 2 houses and a vacant lot create the perfect investment opportunity! Comprised of a 4 unit apartment building and a single unit house with a 4 car garage under and an adjacent vacant lot. The vacant lot is perfect for additional parking and or play area! All tenants have been there long term and pay regularly. Buyer and buyer agent to do own due diligence.

27 Thibault Ave, Winchester

$388,750

Two parcels for the price of one! Discover this beautifully maintained split-level ranch at 111 Old North Road in Winchester, offered together with the adjoining already-subdivided 2.5-acre buildable lot at 113 Old North Road. Enjoy the home as-is or explore the endless possibilities-build an in-law house, sell the lot, or develop it as an investment. Inside, the home features a unique layout with soaring vaulted ceilings, a dual-sided fireplace, and an interior balcony overlooking the formal dining room. The full walkout basement, complete with a half bath, offers incredible potential to finish for additional living space, a guest suite, or a home office. Additional highlights include central air, a stone patio perfect for entertaining, a covered breezeway with scenic views, and a paved driveway. All set on a private, secluded lot, this property combines comfort, versatility, and opportunity rarely found on the market.

3 Beds ⋅ 3 Baths ⋅ 24120714 MLS

Two parcels for the price of one! Discover this beautifully maintained split-level ranch at 111 Old North Road in Winchester, offered together with the adjoining already-subdivided 2.5-acre buildable lot at 113 Old North Road. Enjoy the home as-is or explore the endless possibilities-build an in-law house, sell the lot, or develop it as an investment. Inside, the home features a unique layout with soaring vaulted ceilings, a dual-sided fireplace, and an interior balcony overlooking the formal dining room. The full walkout basement, complete with a half bath, offers incredible potential to finish for additional living space, a guest suite, or a home office. Additional highlights include central air, a stone patio perfect for entertaining, a covered breezeway with scenic views, and a paved driveway. All set on a private, secluded lot, this property combines comfort, versatility, and opportunity rarely found on the market.

111 Old North Rd, Winchester

$387,500

Extremely well-cared-for two-family home located on a desirable street! This property offers plenty of off-street parking, a rear lot, a 3-car garage with basement adds potential for additional income. Large back yard with gazebo.The first floor is unoccupied, while the second floor is tenant-occupied, making this a great opportunity for an owner-occupant or investor. Come take a look while it lasts!

6 Beds ⋅ 3 Baths ⋅ 24177338 MLS

Extremely well-cared-for two-family home located on a desirable street! This property offers plenty of off-street parking, a rear lot, a 3-car garage with basement adds potential for additional income. Large back yard with gazebo.The first floor is unoccupied, while the second floor is tenant-occupied, making this a great opportunity for an owner-occupant or investor. Come take a look while it lasts!

68 Wetmore Ave, Winchester

$385,000

Discover this beautifully maintained 3-bedroom, 1.5-bath Colonial set on a level one-acre lot less than two miles from town. This home has been thoughtfully updated over the years and is truly move-in ready. Enjoy a spacious living room and family room, each featuring a cozy fireplace-perfect for New England seasons. The updated kitchen offers modern appliances and a bright, comfortable workspace. Gleaming hardwood floors run throughout the home, adding warmth and character to every room. Step outside to the attractive fieldstone patio complete with a built-in barbecue, an ideal setting for outdoor dining and entertaining. This property has an impressive list of improvements, including a new boiler and hot water heater (2016), well pump and tank (2014), updated siding, roof, gutters with guards, and garage doors (2022), and Pella windows installed in 2025. In excellent condition and offering tremendous value, this charming home is ready for its next owner to enjoy all it has to offer.

3 Beds ⋅ 2 Baths ⋅ 24142296 MLS

Discover this beautifully maintained 3-bedroom, 1.5-bath Colonial set on a level one-acre lot less than two miles from town. This home has been thoughtfully updated over the years and is truly move-in ready. Enjoy a spacious living room and family room, each featuring a cozy fireplace-perfect for New England seasons. The updated kitchen offers modern appliances and a bright, comfortable workspace. Gleaming hardwood floors run throughout the home, adding warmth and character to every room. Step outside to the attractive fieldstone patio complete with a built-in barbecue, an ideal setting for outdoor dining and entertaining. This property has an impressive list of improvements, including a new boiler and hot water heater (2016), well pump and tank (2014), updated siding, roof, gutters with guards, and garage doors (2022), and Pella windows installed in 2025. In excellent condition and offering tremendous value, this charming home is ready for its next owner to enjoy all it has to offer.

208 Spencer Hill Rd, Winchester

$375,000

Nestled in a peaceful rural setting of Winchester Center, this charming home offers a perfect blend of rustic character and modern convenience. The property is located on over 3.3 acres of land and is adjacent to a scenic pond. Inside you will find a three bedroom two bath home with an additional in law apartment with one full bath and one bedroom and its own private entrance. The home also offers a Generac whole house generator for your convenience. There is also a spacious wine cellar in the basement. Outside you will find rock walls throughout the property, an inviting patio, and a large shed for your storage needs. Owner/Agent

3 Beds ⋅ 3 Baths ⋅ 24096267 MLS

Nestled in a peaceful rural setting of Winchester Center, this charming home offers a perfect blend of rustic character and modern convenience. The property is located on over 3.3 acres of land and is adjacent to a scenic pond. Inside you will find a three bedroom two bath home with an additional in law apartment with one full bath and one bedroom and its own private entrance. The home also offers a Generac whole house generator for your convenience. There is also a spacious wine cellar in the basement. Outside you will find rock walls throughout the property, an inviting patio, and a large shed for your storage needs. Owner/Agent

117 South Rd, Winchester

$375,000

Charming Cape 2 minutes to Highland Lake. Welcome to this one owner, 3 bedroom, two bath Cape Cod home offering over 1,800 sq. ft. of living space on nearly one acre of land. Owned by the original family. This property has been lovingly maintained and thoughtfully update. Step inside to find a fully appliance kitchen, fresh carpeting, and updated windows and gutters. The flexible seven- room layout provides space for comfortable living, entertaining, and home office needs. This home features a two- car under the house, plus a side carport and two driveways, making parking and storage a breeze. A full basement offers additional possibilities. Outdoors, enjoy a deep, private yard with room to relax, garden or entertain. Yard also has a peach tree, blueberry & raspberry bushes, and many strawberry plants. Best of all, you're just minutes from Highland Lake's public beach, perfect for summer fun and year round recreation. Don't miss this rare opportunity to own a one-owner home in sought- after location.

3 Beds ⋅ 2 Baths ⋅ 24115956 MLS

Charming Cape 2 minutes to Highland Lake. Welcome to this one owner, 3 bedroom, two bath Cape Cod home offering over 1,800 sq. ft. of living space on nearly one acre of land. Owned by the original family. This property has been lovingly maintained and thoughtfully update. Step inside to find a fully appliance kitchen, fresh carpeting, and updated windows and gutters. The flexible seven- room layout provides space for comfortable living, entertaining, and home office needs. This home features a two- car under the house, plus a side carport and two driveways, making parking and storage a breeze. A full basement offers additional possibilities. Outdoors, enjoy a deep, private yard with room to relax, garden or entertain. Yard also has a peach tree, blueberry & raspberry bushes, and many strawberry plants. Best of all, you're just minutes from Highland Lake's public beach, perfect for summer fun and year round recreation. Don't miss this rare opportunity to own a one-owner home in sought- after location.

126 Forest Ave, Winchester

$370,000

Summer is coming-be ready for it at 351 Platt Hill Road! Tucked away in a scenic setting yet only 1 mile from Highland Lake, this 3-bedroom, 2-bath home is the perfect year-round retreat or weekend getaway. Leave the stairs behind and enjoy true one-level living. The floor plan is designed for easy flow, featuring a primary suite and two additional bedrooms on the main floor. The surprise factor is the lower level: a partially finished basement that effectively expands your living space, offering the perfect spot for movie nights, a playroom, or overflow guest space. Outside, enjoy the peaceful setting typical of Platt Hill. Entertain family in your large, level yard while being just minutes from boat launches, beaches, and the vibrant Winsted town center. With warm weather around the corner, this is your chance to secure a home where "Lake Life" is just a quick walk or drive away. Schedule your showing today!

3 Beds ⋅ 2 Baths ⋅ 24154916 MLS

Summer is coming-be ready for it at 351 Platt Hill Road! Tucked away in a scenic setting yet only 1 mile from Highland Lake, this 3-bedroom, 2-bath home is the perfect year-round retreat or weekend getaway. Leave the stairs behind and enjoy true one-level living. The floor plan is designed for easy flow, featuring a primary suite and two additional bedrooms on the main floor. The surprise factor is the lower level: a partially finished basement that effectively expands your living space, offering the perfect spot for movie nights, a playroom, or overflow guest space. Outside, enjoy the peaceful setting typical of Platt Hill. Entertain family in your large, level yard while being just minutes from boat launches, beaches, and the vibrant Winsted town center. With warm weather around the corner, this is your chance to secure a home where "Lake Life" is just a quick walk or drive away. Schedule your showing today!

351 Platt Hill Rd, Winchester

$370,000

This charming ranch-style home offers comfortable single-level living with thoughtful features throughout. Boasting 3 bedrooms and 2 full bathrooms, this home blends functionality with character. Beautiful hardwood floors flow through much of the living space, while vaulted ceilings create an open and airy feel. One of the bedrooms features a unique loft area, perfect for additional sleeping space, a reading nook, or creative use. The home opens to a heated enclosed porch, providing a cozy year-round retreat overlooking the backyard. Step outside onto the spacious deck, ideal for entertaining, grilling, or simply enjoying the peaceful surroundings. Set on a generous 0.35-acre lot, the property features an open, level backyard complete with a firepit - perfect for gatherings, outdoor fun, or relaxing evenings under the stars. Energy-conscious buyers will appreciate the solar panels, helping to offset utility costs. Additional highlights include a 1-car under-house garage for convenience and storage, along with a detached shed for lawn equipment, hobbies, or additional storage needs. Offering charm, efficiency, and easy living, this home is ready for its next owner to enjoy.

2 Beds ⋅ 2 Baths ⋅ 24152814 MLS

This charming ranch-style home offers comfortable single-level living with thoughtful features throughout. Boasting 3 bedrooms and 2 full bathrooms, this home blends functionality with character. Beautiful hardwood floors flow through much of the living space, while vaulted ceilings create an open and airy feel. One of the bedrooms features a unique loft area, perfect for additional sleeping space, a reading nook, or creative use. The home opens to a heated enclosed porch, providing a cozy year-round retreat overlooking the backyard. Step outside onto the spacious deck, ideal for entertaining, grilling, or simply enjoying the peaceful surroundings. Set on a generous 0.35-acre lot, the property features an open, level backyard complete with a firepit - perfect for gatherings, outdoor fun, or relaxing evenings under the stars. Energy-conscious buyers will appreciate the solar panels, helping to offset utility costs. Additional highlights include a 1-car under-house garage for convenience and storage, along with a detached shed for lawn equipment, hobbies, or additional storage needs. Offering charm, efficiency, and easy living, this home is ready for its next owner to enjoy.

171 Wallens St, Winchester

$370,000

Nothing to do but move right in to this meticulous colonial farmhouse nestled in the Litchfield Hills. This unique home combines a tasteful modern style mixed with rustic charm. Inside the fully renovated home offers a sprawling kitchen with ample counter and cabinet space, a breakfast bar with elegant quartz countertops and newer stainless steel appliances. The space is open to the dining area to make entertaining easy! The living room area is nestled at the end of the house with custom built in book shelves and a french door to close off if you want to enjoy some quiet time! Upstairs you will find the the primary bedroom with a large, walk in closet and two additional bedrooms and a full bath. Outside you can enjoy the view of the yard from a spacious deck. Don't worry about the dogs or littles, they have plenty of space to roam safely in the fenced in area.

3 Beds ⋅ 2 Baths ⋅ 24120271 MLS

Nothing to do but move right in to this meticulous colonial farmhouse nestled in the Litchfield Hills. This unique home combines a tasteful modern style mixed with rustic charm. Inside the fully renovated home offers a sprawling kitchen with ample counter and cabinet space, a breakfast bar with elegant quartz countertops and newer stainless steel appliances. The space is open to the dining area to make entertaining easy! The living room area is nestled at the end of the house with custom built in book shelves and a french door to close off if you want to enjoy some quiet time! Upstairs you will find the the primary bedroom with a large, walk in closet and two additional bedrooms and a full bath. Outside you can enjoy the view of the yard from a spacious deck. Don't worry about the dogs or littles, they have plenty of space to roam safely in the fenced in area.

166 Torringford St, Winchester

$368,500

This move-in-ready Colonial-style home blends classic charm with modern updates. Featuring a remodeled kitchen with a large center island, cherry cabinets, granite countertops, stainless steel appliances, and a wine fridge. The main level also offers a dining room with refinished hardwood floors, a living room, and a flexible family room. Upstairs includes three bedrooms and a full bath, with a spacious primary bedroom and a custom walk-in closet. Outside, enjoy a patio, pool, and fully fenced yard. Additional highlights include updated siding, roof, and driveway, a heated one-bay garage/workshop and plenty of parking with two driveways.

3 Beds ⋅ 2 Baths ⋅ 24168531 MLS

This move-in-ready Colonial-style home blends classic charm with modern updates. Featuring a remodeled kitchen with a large center island, cherry cabinets, granite countertops, stainless steel appliances, and a wine fridge. The main level also offers a dining room with refinished hardwood floors, a living room, and a flexible family room. Upstairs includes three bedrooms and a full bath, with a spacious primary bedroom and a custom walk-in closet. Outside, enjoy a patio, pool, and fully fenced yard. Additional highlights include updated siding, roof, and driveway, a heated one-bay garage/workshop and plenty of parking with two driveways.

102 Wallens St, Winchester

$365,000

Discover the perfect blend of small time charm with many conveniences close at hand! This well maintained, warm and inviting, 1 owner home offers it all! Having beautiful Highland Lake in this community is certainly one of many pluses! The renovated eat in kitchen offers granite counter tops, stainless steel appliances and access to a beautiful new Trex deck! Along with new decking, new windows have been installed. A more formal dining area flows from the kitchen, making entertaining convenient. The bedrooms, full bathroom and laundry nook are all found on the main floor. The tastefully finished basement with half bath leads directly to the one car garage. There is ample backyard space for playscapes and so much more! Don't wait! This home will not last long!

3 Beds ⋅ 2 Baths ⋅ 24162992 MLS

Discover the perfect blend of small time charm with many conveniences close at hand! This well maintained, warm and inviting, 1 owner home offers it all! Having beautiful Highland Lake in this community is certainly one of many pluses! The renovated eat in kitchen offers granite counter tops, stainless steel appliances and access to a beautiful new Trex deck! Along with new decking, new windows have been installed. A more formal dining area flows from the kitchen, making entertaining convenient. The bedrooms, full bathroom and laundry nook are all found on the main floor. The tastefully finished basement with half bath leads directly to the one car garage. There is ample backyard space for playscapes and so much more! Don't wait! This home will not last long!

262 Holabird Ave, Winchester

$362,000

HUGE PRICE REDUCTION!! Make this beautiful Cape your home! Features 4 spacious bedrooms and a full bathroom on each floor. Enjoy watching the birds & other wildlife on the huge rear deck or enjoy the peaceful setting on the enclosed porch. The grounds have been lovingly maintained.

4 Beds ⋅ 2 Baths ⋅ 24111148 MLS

HUGE PRICE REDUCTION!! Make this beautiful Cape your home! Features 4 spacious bedrooms and a full bathroom on each floor. Enjoy watching the birds & other wildlife on the huge rear deck or enjoy the peaceful setting on the enclosed porch. The grounds have been lovingly maintained.

147 Smith Hill Rd, Winchester

$360,000

Nestled on a private lot in scenic Winchester, this beautifully maintained home offers a wonderful blend of comfort, character, and natural surroundings. Hardwood floors welcome you into the bright and inviting interior, where the custom kitchen serves as the heart of the home with hickory cabinetry, granite countertops, tile backsplash, and stainless-steel appliances. The second floor features attractive oak flooring, while thoughtful upgrades throughout the home provide comfort and convenience. Step outside to enjoy your own backyard retreat, complete with a tranquil pond, spacious deck, granite walkway, and storage shed. Additional features include central air conditioning, stand-by generator , replacement windows, a whole-house humidifier, updated hot water system, and more. The property offers a peaceful setting ideal for relaxing, entertaining, or simply enjoying nature. If you've been searching for privacy, quality improvements, and a move-in ready home in a picturesque Northwest Connecticut setting, this is one you won't want to miss.

2 Beds ⋅ 2 Baths ⋅ 24180470 MLS

Nestled on a private lot in scenic Winchester, this beautifully maintained home offers a wonderful blend of comfort, character, and natural surroundings. Hardwood floors welcome you into the bright and inviting interior, where the custom kitchen serves as the heart of the home with hickory cabinetry, granite countertops, tile backsplash, and stainless-steel appliances. The second floor features attractive oak flooring, while thoughtful upgrades throughout the home provide comfort and convenience. Step outside to enjoy your own backyard retreat, complete with a tranquil pond, spacious deck, granite walkway, and storage shed. Additional features include central air conditioning, stand-by generator , replacement windows, a whole-house humidifier, updated hot water system, and more. The property offers a peaceful setting ideal for relaxing, entertaining, or simply enjoying nature. If you've been searching for privacy, quality improvements, and a move-in ready home in a picturesque Northwest Connecticut setting, this is one you won't want to miss.

212 Spencer Hill Rd, Winchester

$360,000

Welcome to 187 Torringford Rd! Set on a beautiful 4-acre lot, this spacious 4-bedroom home offers the perfect blend of natural light, character, and country living. Step inside through the mudroom, also serving as a convenient laundry area, and head up to a charming loft that overlooks the bright, window filled kitchen. The kitchen features an abundance of natural light and provides a warm, inviting space for cooking and gathering. Adjacent to the kitchen is a cozy breakfast nook with a bay window, opening seamlessly into the living room for easy everyday living. Across the hall, you'll find a generous family room and a separate dining room, offering plenty of room for entertaining and hosting holidays. A half bath completes the main level. Upstairs are four bedrooms, creating flexible options for family, guests, or office space. Outside, the property truly shines with a two-story garage/barn featuring a loft, perfect for storage, a workshop, or hobby space. Enjoy summer days in the above-ground pool. Appreciate new 5 year old roof. The 4-acre lot provides both open, usable yard space and lightly wooded areas, ideal for gardens, animals, recreation, or simply soaking in the peaceful surroundings. This charming property offers privacy, potential, and the opportunity to make it your own. Schedule your showing today!

4 Beds ⋅ 2 Baths ⋅ 24138466 MLS

Welcome to 187 Torringford Rd! Set on a beautiful 4-acre lot, this spacious 4-bedroom home offers the perfect blend of natural light, character, and country living. Step inside through the mudroom, also serving as a convenient laundry area, and head up to a charming loft that overlooks the bright, window filled kitchen. The kitchen features an abundance of natural light and provides a warm, inviting space for cooking and gathering. Adjacent to the kitchen is a cozy breakfast nook with a bay window, opening seamlessly into the living room for easy everyday living. Across the hall, you'll find a generous family room and a separate dining room, offering plenty of room for entertaining and hosting holidays. A half bath completes the main level. Upstairs are four bedrooms, creating flexible options for family, guests, or office space. Outside, the property truly shines with a two-story garage/barn featuring a loft, perfect for storage, a workshop, or hobby space. Enjoy summer days in the above-ground pool. Appreciate new 5 year old roof. The 4-acre lot provides both open, usable yard space and lightly wooded areas, ideal for gardens, animals, recreation, or simply soaking in the peaceful surroundings. This charming property offers privacy, potential, and the opportunity to make it your own. Schedule your showing today!

187 Torringford St, Winchester

$350,000

Peaceful country living with unlimited potential! Nestled on a quiet Winsted street, this three bedroom, two bathroom ranch sits on nearly 2 acres of private, setback land. It offers excellant structural bones and a functonal layout, making it an ideal candidate for a rewarding renovation project. The large living and dining space features high cathedral ceilings and exposed wood beams with the focal point of the living room being a floor to ceiling fireplace equipped with a wood stove insert. Convenient one-level living at it's best! A two car attached garage leads to a breezeway room, ideal for a home office or studio. The home requires updates throughout and is being sold strictly "as is." The price of this property reflects its current condition, offering a solid foundation to buyers looking to customize a home.

3 Beds ⋅ 2 Baths ⋅ 24177410 MLS

Peaceful country living with unlimited potential! Nestled on a quiet Winsted street, this three bedroom, two bathroom ranch sits on nearly 2 acres of private, setback land. It offers excellant structural bones and a functonal layout, making it an ideal candidate for a rewarding renovation project. The large living and dining space features high cathedral ceilings and exposed wood beams with the focal point of the living room being a floor to ceiling fireplace equipped with a wood stove insert. Convenient one-level living at it's best! A two car attached garage leads to a breezeway room, ideal for a home office or studio. The home requires updates throughout and is being sold strictly "as is." The price of this property reflects its current condition, offering a solid foundation to buyers looking to customize a home.

107 Roberts Ave, Winchester

$350,000

Welcome to 9 Colony Dr, a charming 3-bedroom, 2 full bath Cape offering a versatile and comfortable layout suited for today's lifestyle. The main level features a bright living room, a convenient first-floor bedroom, a full bath, and a modern kitchen with dining area perfect for everyday living and entertaining. The upper level offers two modestly sized bedrooms along with an additional full bath, providing ample space for family or guests. The lower level adds approximately 400 square feet of finished living space ideal for a family room, home office, or flexible use to fit your needs, and includes a walkout to the rear fenced yard complete with a paver patio for outdoor enjoyment. Mechanically, the home is equipped with a natural gas boiler and hot water heater, offering efficiency and reliability. This well-rounded home is poised to attract strong interest and is truly destined to sell quickly. Easy access to Rte's 8 and 44 and a short drive to Farmington Valley.

3 Beds ⋅ 2 Baths ⋅ 24168127 MLS

Welcome to 9 Colony Dr, a charming 3-bedroom, 2 full bath Cape offering a versatile and comfortable layout suited for today's lifestyle. The main level features a bright living room, a convenient first-floor bedroom, a full bath, and a modern kitchen with dining area perfect for everyday living and entertaining. The upper level offers two modestly sized bedrooms along with an additional full bath, providing ample space for family or guests. The lower level adds approximately 400 square feet of finished living space ideal for a family room, home office, or flexible use to fit your needs, and includes a walkout to the rear fenced yard complete with a paver patio for outdoor enjoyment. Mechanically, the home is equipped with a natural gas boiler and hot water heater, offering efficiency and reliability. This well-rounded home is poised to attract strong interest and is truly destined to sell quickly. Easy access to Rte's 8 and 44 and a short drive to Farmington Valley.

9 Colony Dr, Winchester

$345,000

Coming Soon! Spacious Cape-style home offering over 2,000 sq. ft. with 4 bedrooms and 2 full baths. This solid home sits on a beautiful lot and is ready for your personal finishing touches. Features include a 2-car garage, 2 fireplaces, and a large, beamed family room just off the kitchen. Recent updates include a new furnace and hot water heater, plus a newer roof for peace of mind. With hardwood floors likely under the carpeting, this home offers excellent potential to make it your own. Don't wait because this one will not last.

4 Beds ⋅ 2 Baths ⋅ 24130055 MLS

Coming Soon! Spacious Cape-style home offering over 2,000 sq. ft. with 4 bedrooms and 2 full baths. This solid home sits on a beautiful lot and is ready for your personal finishing touches. Features include a 2-car garage, 2 fireplaces, and a large, beamed family room just off the kitchen. Recent updates include a new furnace and hot water heater, plus a newer roof for peace of mind. With hardwood floors likely under the carpeting, this home offers excellent potential to make it your own. Don't wait because this one will not last.

115 Wallens St, Winchester

$341,000

Welcome to 188 Glendale Avenue! This charming 3-4 bedroom ranch sits on a quiet cul-de-sac. This home boasts of beautiful evening sunsets and quiet mornings sipping coffee on a secluded backyard patio. There have been many updates added, including vinyl windows, a new circuit panel and a new walk-in shower. Entering the home, you find a cozy living room with a working fireplace. The kitchen/dining area looks out at the park-like, wooded back yard with flowering bushes. On this level hardwood floors can be found throughtout, presently covered by carpeting. You will also find three bedrooms with one full bath and one half bath. In the lower level of the home, an additional 500 Square Feet can be found in the well-kept finished basement, allowing for what could be a fourth separate bedroom and an additional den. This area leads to the one car garage. This home is a must see and will not be on the market long!

3 Beds ⋅ 2 Baths ⋅ 24179585 MLS

Welcome to 188 Glendale Avenue! This charming 3-4 bedroom ranch sits on a quiet cul-de-sac. This home boasts of beautiful evening sunsets and quiet mornings sipping coffee on a secluded backyard patio. There have been many updates added, including vinyl windows, a new circuit panel and a new walk-in shower. Entering the home, you find a cozy living room with a working fireplace. The kitchen/dining area looks out at the park-like, wooded back yard with flowering bushes. On this level hardwood floors can be found throughtout, presently covered by carpeting. You will also find three bedrooms with one full bath and one half bath. In the lower level of the home, an additional 500 Square Feet can be found in the well-kept finished basement, allowing for what could be a fourth separate bedroom and an additional den. This area leads to the one car garage. This home is a must see and will not be on the market long!

188 Glendale Ave, Winchester

$340,000

Step into luxury in this nicely updated 3-bedroom raised ranch, perfectly positioned on a quiet cul-de-sac. The interior shines with hardwood floors and a designer kitchen boasting new custom cabinetry, quartz countertops and stainless-steel appliances. Lower level is completely finished featuring a large family room with natural gas stove. Enjoy maintenance-free living with a newer roof (less than 5 years old) and new gas boiler and electric water heater. Located in the heart of the Litchfield Hills, you're just moments from Highland Lake, local parks, and the top-rated Gilbert School. Includes a shed for more storage. Agent/owner. Move-in ready and priced to sell-schedule your showing today! "Lower lot area is part of the property, which can be cleared and used as new owners envision.

3 Beds ⋅ 2 Baths ⋅ 24164318 MLS

Step into luxury in this nicely updated 3-bedroom raised ranch, perfectly positioned on a quiet cul-de-sac. The interior shines with hardwood floors and a designer kitchen boasting new custom cabinetry, quartz countertops and stainless-steel appliances. Lower level is completely finished featuring a large family room with natural gas stove. Enjoy maintenance-free living with a newer roof (less than 5 years old) and new gas boiler and electric water heater. Located in the heart of the Litchfield Hills, you're just moments from Highland Lake, local parks, and the top-rated Gilbert School. Includes a shed for more storage. Agent/owner. Move-in ready and priced to sell-schedule your showing today! "Lower lot area is part of the property, which can be cleared and used as new owners envision.

1 Hamill Dr, Winchester

$335,000

Move right into this absolutely charming Colonial with incredible curb appeal & pride of ownership throughout! Lovingly maintained & impeccably clean, this true dollhouse is set on .31 acres in the scenic, beautiful Litchfield Hills & just minutes to Northwestern Community College, the town green, shopping, restaurants, walking trails, biking, & endless outdoor recreation. From the moment you arrive, you'll appreciate the inviting new walkway leading to the covered front porch-perfect for morning coffee or relaxing evenings. Step inside & fall in love with the warm and welcoming interior featuring hardwood floors and timeless character throughout. The spacious living room offers a comfortable gathering space, while the sunny eat-in kitchen boasts abundant granite counter space, ample cabinetry, & room for everyday dining. The formal dining room adds charm with beadboard detail and crown molding-ideal for entertaining. A convenient first-floor half bath with laundry completes the main level. Upstairs, the second floor offers a huge primary bedroom with generous closet space plus another spacious bedroom, both featuring hardwood floors and oversized closets. The third floor hosts an impressive third bedroom with built-ins & exceptional storage options. Outside, enjoy the freshly painted deck, sweet patio surrounded by beautiful perennial gardens and a nice backyard setting. Car enthusiasts, hobbyists, or anyone needing extra space will appreciate the rare detached 3 car garage

3 Beds ⋅ 2 Baths ⋅ 24178756 MLS

Move right into this absolutely charming Colonial with incredible curb appeal & pride of ownership throughout! Lovingly maintained & impeccably clean, this true dollhouse is set on .31 acres in the scenic, beautiful Litchfield Hills & just minutes to Northwestern Community College, the town green, shopping, restaurants, walking trails, biking, & endless outdoor recreation. From the moment you arrive, you'll appreciate the inviting new walkway leading to the covered front porch-perfect for morning coffee or relaxing evenings. Step inside & fall in love with the warm and welcoming interior featuring hardwood floors and timeless character throughout. The spacious living room offers a comfortable gathering space, while the sunny eat-in kitchen boasts abundant granite counter space, ample cabinetry, & room for everyday dining. The formal dining room adds charm with beadboard detail and crown molding-ideal for entertaining. A convenient first-floor half bath with laundry completes the main level. Upstairs, the second floor offers a huge primary bedroom with generous closet space plus another spacious bedroom, both featuring hardwood floors and oversized closets. The third floor hosts an impressive third bedroom with built-ins & exceptional storage options. Outside, enjoy the freshly painted deck, sweet patio surrounded by beautiful perennial gardens and a nice backyard setting. Car enthusiasts, hobbyists, or anyone needing extra space will appreciate the rare detached 3 car garage

405 N Main St, Winchester

$335,000

Enjoy years of maintenance-free living in this beautifully maintained 3-bedroom, 2-bath home, ideally situated on a quiet side street just minutes from the beach at Highland Lake and the shops, restaurants, and conveniences of downtown Winsted. Completely remodeled in 2017, this home offers a long list of updates at that time including a new roof, updated baths, remodeled kitchen, all new flooring, new deck, newer heating system, and freshly painted interior and exterior. The current owner has meticulously maintained the home, preserving its like-new condition. The lower level provides excellent flexibility and offers the potential for an in-law suite, home office, or additional living space. Whether you're looking for comfort, convenience, or versatility, this home delivers it all. Don't wait-this one is here today and gone tomorrow.

3 Beds ⋅ 2 Baths ⋅ 24155057 MLS

Enjoy years of maintenance-free living in this beautifully maintained 3-bedroom, 2-bath home, ideally situated on a quiet side street just minutes from the beach at Highland Lake and the shops, restaurants, and conveniences of downtown Winsted. Completely remodeled in 2017, this home offers a long list of updates at that time including a new roof, updated baths, remodeled kitchen, all new flooring, new deck, newer heating system, and freshly painted interior and exterior. The current owner has meticulously maintained the home, preserving its like-new condition. The lower level provides excellent flexibility and offers the potential for an in-law suite, home office, or additional living space. Whether you're looking for comfort, convenience, or versatility, this home delivers it all. Don't wait-this one is here today and gone tomorrow.

44 Lewis St, Winchester

$330,000

Discover 63 Meadow, a turnkey 3-unit asset where thoughtful updates, strong rental performance, and a prime location come together to prove a high confidence investment opportunity. The property offers three well-proportioned units, a two-car attached garage, off-street parking spaces, and shared outdoor area that tenants appreciate. The current owner continued to elevate the building's value and safety with electrical upgrades, a new sump pump, new hot water tank, and fire marshal approved improvements throughout the walkways and stairways. Rental rates reflect market, further improving ROI. Unit 1 features two bedrooms, full bath, mudroom with laundry, enclosed front porch, side porch, with interior updated in 2024. Unit (2F) spans the footprint of the first floor and now includes in unit laundry, updated in 2024 with carpeting, fresh paint, creating a bright and functional living space with multiple rooms and a generous walk-in closet. Unit 2R is a cozy 1BR with an eat in kitchen, living room, and updated finishes including paint, countertops, flooring, and toilet (2023). All units offer two egresses, one exterior and one through the common area. Tenants enjoy quick access to Route 8, a local university, and everyday conveniences. A short walk to Dunkin', Red Barn, and only a 2 mile walk to Highland Lake. It's combination of location, upgrades and improvements, and strong rental income already in place, it's a standout addition to any portfolio! AS IS.

5 Beds ⋅ 3 Baths ⋅ 24175107 MLS

Discover 63 Meadow, a turnkey 3-unit asset where thoughtful updates, strong rental performance, and a prime location come together to prove a high confidence investment opportunity. The property offers three well-proportioned units, a two-car attached garage, off-street parking spaces, and shared outdoor area that tenants appreciate. The current owner continued to elevate the building's value and safety with electrical upgrades, a new sump pump, new hot water tank, and fire marshal approved improvements throughout the walkways and stairways. Rental rates reflect market, further improving ROI. Unit 1 features two bedrooms, full bath, mudroom with laundry, enclosed front porch, side porch, with interior updated in 2024. Unit (2F) spans the footprint of the first floor and now includes in unit laundry, updated in 2024 with carpeting, fresh paint, creating a bright and functional living space with multiple rooms and a generous walk-in closet. Unit 2R is a cozy 1BR with an eat in kitchen, living room, and updated finishes including paint, countertops, flooring, and toilet (2023). All units offer two egresses, one exterior and one through the common area. Tenants enjoy quick access to Route 8, a local university, and everyday conveniences. A short walk to Dunkin', Red Barn, and only a 2 mile walk to Highland Lake. It's combination of location, upgrades and improvements, and strong rental income already in place, it's a standout addition to any portfolio! AS IS.

63 Meadow St, Winchester

$330,000

What a wonderful Home! Walk in and be Wowed! This 4 bedroom home built in 1900 has been meticulously redone inside and out in 2020. Featuring gleaming hardwood floors on all 3 floors. Thermal paned windows through out. Spacious 12x10 foyer makes a great sitting room or office. First floor has the open floor plan with formal dining, living room and kitchen all in one. Comes with a full bath and laundry room on the first floor. New kitchen with gas stove. Second floor features 4 large bedrooms with wood floors, freshly painted and a full bath. Primary bedroom has a large walk-in closet. Walk up to the 3rd floor and enjoy a playroom with walk in closet, home office or studio. Energy efficient windows, tankless hot water heater and gas furnace. The numerous windows offer a very bright and inviting natural light source. Complete with central air and wrap around porch. Nothing to do but move on in and relax. Located within the school zone and walking distance to elementary, middle and high schools, as well as, the local playground, Main Street parades and town green with summer activities. Dont forget to get your parking pass for town residents to the well known Highland lake with 2 beaches and boating activities.

4 Beds ⋅ 2 Baths ⋅ 24150199 MLS

What a wonderful Home! Walk in and be Wowed! This 4 bedroom home built in 1900 has been meticulously redone inside and out in 2020. Featuring gleaming hardwood floors on all 3 floors. Thermal paned windows through out. Spacious 12x10 foyer makes a great sitting room or office. First floor has the open floor plan with formal dining, living room and kitchen all in one. Comes with a full bath and laundry room on the first floor. New kitchen with gas stove. Second floor features 4 large bedrooms with wood floors, freshly painted and a full bath. Primary bedroom has a large walk-in closet. Walk up to the 3rd floor and enjoy a playroom with walk in closet, home office or studio. Energy efficient windows, tankless hot water heater and gas furnace. The numerous windows offer a very bright and inviting natural light source. Complete with central air and wrap around porch. Nothing to do but move on in and relax. Located within the school zone and walking distance to elementary, middle and high schools, as well as, the local playground, Main Street parades and town green with summer activities. Dont forget to get your parking pass for town residents to the well known Highland lake with 2 beaches and boating activities.

123 Wetmore Ave, Winchester