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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

$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

$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

$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

$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

Private Country Living on 16 Acres! Enjoy the peace and privacy of this charming ranch nestled on expansive acreage, offering the feel of a true country compound. Features include 2 bedrooms, a family room with fireplace, kitchen, three-season enclosed porch, heated possible office, and large deck. Plenty of cleared land surrounds the homesite while mature trees provide exceptional privacy. Possible subdivision potential adds even more opportunity. Buyer to verify with the town. A rare opportunity for those seeking space, privacy, and endless possibilities!

2 Beds ⋅ 2 Baths ⋅ 24206905 MLS

Private Country Living on 16 Acres! Enjoy the peace and privacy of this charming ranch nestled on expansive acreage, offering the feel of a true country compound. Features include 2 bedrooms, a family room with fireplace, kitchen, three-season enclosed porch, heated possible office, and large deck. Plenty of cleared land surrounds the homesite while mature trees provide exceptional privacy. Possible subdivision potential adds even more opportunity. Buyer to verify with the town. A rare opportunity for those seeking space, privacy, and endless possibilities!

320 Colebrook Rd, 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

$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

$350,000

Well-maintained two-family home offering spacious apartments, separate utilities, and a convenient location within walking distance to downtown amenities. The first-floor apartment features approximately 1,620 sq. ft. with a kitchen, living room, dining room, full bath, and 2-3 bedrooms. The second-floor apartment offers approximately 1,424 sq. ft. with a similar layout including a kitchen, living room, dining room, full bath, and 2-3 bedrooms. Each unit is serviced by its own efficient natural gas boiler and hot water and features a covered porch for additional outdoor living space. Situated on a generous .56-acre lot, the property also includes a two-story barn offering excellent storage and additional possibilities. A nicely maintained property with spacious units and a desirable location close to shopping, restaurants, and other downtown conveniences. An excellent opportunity for an owner-occupant or investor.

4 Beds ⋅ 2 Baths ⋅ 24199721 MLS

Well-maintained two-family home offering spacious apartments, separate utilities, and a convenient location within walking distance to downtown amenities. The first-floor apartment features approximately 1,620 sq. ft. with a kitchen, living room, dining room, full bath, and 2-3 bedrooms. The second-floor apartment offers approximately 1,424 sq. ft. with a similar layout including a kitchen, living room, dining room, full bath, and 2-3 bedrooms. Each unit is serviced by its own efficient natural gas boiler and hot water and features a covered porch for additional outdoor living space. Situated on a generous .56-acre lot, the property also includes a two-story barn offering excellent storage and additional possibilities. A nicely maintained property with spacious units and a desirable location close to shopping, restaurants, and other downtown conveniences. An excellent opportunity for an owner-occupant or investor.

50 High 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

$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

$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

$325,000

Excellent opportunity for both owner-occupants and investors! This well-maintained two-family home features two spacious units, each offering 5 rooms, 2 bedrooms, and 1 full bath. Both apartments showcase beautiful hardwood flooring throughout and are served by separate natural gas heating systems for efficiency and convenience. The upper-level unit includes a charming enclosed porch, providing additional seasonal living space and a perfect spot to relax. Situated on a generous .66-acre lot, the property offers seasonal views of Highland Lake and is within walking distance of two public beaches, making it an ideal location to enjoy all that the area has to offer. Additional features include a detached three-car garage, ample outdoor space, and a desirable setting close to recreation, shopping, dining, and other local amenities. Whether you're looking to generate rental income or occupy one unit while offsetting your mortgage with the other, this is an outstanding opportunity.

4 Beds ⋅ 2 Baths ⋅ 24189235 MLS

Excellent opportunity for both owner-occupants and investors! This well-maintained two-family home features two spacious units, each offering 5 rooms, 2 bedrooms, and 1 full bath. Both apartments showcase beautiful hardwood flooring throughout and are served by separate natural gas heating systems for efficiency and convenience. The upper-level unit includes a charming enclosed porch, providing additional seasonal living space and a perfect spot to relax. Situated on a generous .66-acre lot, the property offers seasonal views of Highland Lake and is within walking distance of two public beaches, making it an ideal location to enjoy all that the area has to offer. Additional features include a detached three-car garage, ample outdoor space, and a desirable setting close to recreation, shopping, dining, and other local amenities. Whether you're looking to generate rental income or occupy one unit while offsetting your mortgage with the other, this is an outstanding opportunity.

120 E Lake St, Winchester

$325,000

Turnkey Winsted gem completely renovated inside & out! Get ready to just move and and not worry. Here is a beautifully reimagined 3-bedroom, 1-bathroom property in Winsted, offering the perfect blend of modern luxury and ultimate peace of mind. Every detail has been thoughtfully updated to create a true turnkey experience. Step inside to a bright, inviting space where the wall between the recently completely renovated kitchen and the living room has been removed to create a seamless, modern open floor plan. The living area features a newly installed mini-split for efficient climate control and a brand-new picture window to let the natural light pour in. The heart of the home is the spectacular, completely renovated kitchen, boasting brand-new cabinetry, elegant tile flooring, and a suite of high-end Samsung Bespoke appliances. The luxury continues into the fully remodeled bathroom, which features crisp new tile floors, sleek glass doors, a new window, and modern cabinetry. Even laundry day is an upgrade with the inclusion of new, extra-large Samsung washer and dryer units. The home boasts striking curb appeal with a brand-new roof, a newly constructed retaining wall, and two sets of new front stairs. The driveway leads to a fantastic, level backyard that is fully enclosed with new perimeter dog fencing. Accessibility is a breeze with a newly built handicap-accessible ramp leading right to the back door.

3 Beds ⋅ 1 Baths ⋅ 24164163 MLS

Turnkey Winsted gem completely renovated inside & out! Get ready to just move and and not worry. Here is a beautifully reimagined 3-bedroom, 1-bathroom property in Winsted, offering the perfect blend of modern luxury and ultimate peace of mind. Every detail has been thoughtfully updated to create a true turnkey experience. Step inside to a bright, inviting space where the wall between the recently completely renovated kitchen and the living room has been removed to create a seamless, modern open floor plan. The living area features a newly installed mini-split for efficient climate control and a brand-new picture window to let the natural light pour in. The heart of the home is the spectacular, completely renovated kitchen, boasting brand-new cabinetry, elegant tile flooring, and a suite of high-end Samsung Bespoke appliances. The luxury continues into the fully remodeled bathroom, which features crisp new tile floors, sleek glass doors, a new window, and modern cabinetry. Even laundry day is an upgrade with the inclusion of new, extra-large Samsung washer and dryer units. The home boasts striking curb appeal with a brand-new roof, a newly constructed retaining wall, and two sets of new front stairs. The driveway leads to a fantastic, level backyard that is fully enclosed with new perimeter dog fencing. Accessibility is a breeze with a newly built handicap-accessible ramp leading right to the back door.

90 Colony Dr, Winchester

$320,000

Lake views that will knock your socks off! Welcome to your own slice of paradise on the shores of Highland Lake, where every day feels like a vacation. Perfectly positioned on one of Connecticut's most sought-after lakes. This home needs some love, but has great bones! Bring your vision and create your dream home!

2 Beds ⋅ 1 Baths ⋅ 24190178 MLS

Lake views that will knock your socks off! Welcome to your own slice of paradise on the shores of Highland Lake, where every day feels like a vacation. Perfectly positioned on one of Connecticut's most sought-after lakes. This home needs some love, but has great bones! Bring your vision and create your dream home!

729 W Wakefield Blvd, Winchester

$320,000

Tucked away on a private road in the sought-after Highland Lake district, this impeccably maintained Ranch offers the perfect blend of privacy, simplicity, and natural beauty. Built in 1995 and set on a .59-acre lot, the home is surrounded by over 500 acres of preserved land, creating a peaceful, nature-filled setting that is increasingly hard to find. Inside, the home features 975 square feet of thoughtfully designed living space, including two bedrooms and one full bath, all in pristine condition. The dining area opens to the outdoors through sliding doors, leading to a rear deck that directly abuts the preserved land-an ideal spot to relax, entertain, or simply take in the quiet surroundings.Enjoy a coveted location near Highland Lake, offering boating, fishing, and year-round recreation, with seasonal lake views that add a subtle yet distinctive layer of charm and serenity. Whether you're looking for a year-round residence or a weekend retreat, this move-in ready home offers a rare opportunity to enjoy low-maintenance living in a truly special location.

2 Beds ⋅ 1 Baths ⋅ 24161635 MLS

Tucked away on a private road in the sought-after Highland Lake district, this impeccably maintained Ranch offers the perfect blend of privacy, simplicity, and natural beauty. Built in 1995 and set on a .59-acre lot, the home is surrounded by over 500 acres of preserved land, creating a peaceful, nature-filled setting that is increasingly hard to find. Inside, the home features 975 square feet of thoughtfully designed living space, including two bedrooms and one full bath, all in pristine condition. The dining area opens to the outdoors through sliding doors, leading to a rear deck that directly abuts the preserved land-an ideal spot to relax, entertain, or simply take in the quiet surroundings.Enjoy a coveted location near Highland Lake, offering boating, fishing, and year-round recreation, with seasonal lake views that add a subtle yet distinctive layer of charm and serenity. Whether you're looking for a year-round residence or a weekend retreat, this move-in ready home offers a rare opportunity to enjoy low-maintenance living in a truly special location.

621 Wynne Rd, Winchester

$310,000

Back on the market due to buyers inability to secure financing. Well-maintained Cape in a desirable rural setting, yet just minutes from shopping, dining, schools, and other everyday conveniences. This 7-room home offers 3 bedrooms and 1.5 baths with a flexible floor plan designed for comfortable living. The main level features a formal living room, dining room, kitchen, family room, primary bedroom, and a full bath w/laundry, providing the convenience of one-level living. Upstairs you'll find two additional bedrooms and a half bath. Lovingly cared for over the years, the home features central air conditioning, a standby generator, and a security system with fire and smoke monitoring for added comfort and peace of mind. Enjoy your morning coffee or evening relaxation on the covered deck overlooking the yard. Additional amenities include a one-car garage under the home and a location that offers the perfect balance of privacy and accessibility. A wonderful opportunity to own a move-in ready home in a convenient country setting. Back on the market due to buyers inability to secure financing

3 Beds ⋅ 2 Baths ⋅ 24186089 MLS

Back on the market due to buyers inability to secure financing. Well-maintained Cape in a desirable rural setting, yet just minutes from shopping, dining, schools, and other everyday conveniences. This 7-room home offers 3 bedrooms and 1.5 baths with a flexible floor plan designed for comfortable living. The main level features a formal living room, dining room, kitchen, family room, primary bedroom, and a full bath w/laundry, providing the convenience of one-level living. Upstairs you'll find two additional bedrooms and a half bath. Lovingly cared for over the years, the home features central air conditioning, a standby generator, and a security system with fire and smoke monitoring for added comfort and peace of mind. Enjoy your morning coffee or evening relaxation on the covered deck overlooking the yard. Additional amenities include a one-car garage under the home and a location that offers the perfect balance of privacy and accessibility. A wonderful opportunity to own a move-in ready home in a convenient country setting. Back on the market due to buyers inability to secure financing

103 Cordano Rd, Winchester

$305,000

*Deadline set of Tuesday 6/30 at Noon. Seller reserves the right to take an offer at anytime.* Nestled on a well maintained lot, this charming Cape offers the perfect balance of privacy and convenience. Set just off the beaten path, the property enjoys a peaceful, rural feel while remaining close to shopping, dining, and everyday amenities. Thoughtfully updated over the years, improvements include vinyl siding, a 10-yr old roof, many newer windows, and numerous interior enhancements, creating a low-maintenance, move-in-ready home. The flexible floor plan features an open-concept kitchen, living, and dining area, a spacious first-floor primary bedroom, and two generously sized bedrooms on the upper level that can also serve as a home office, playroom, or guest space to fit your needs. Step outside to the expansive 14' x 18' deck overlooking the backyard-an ideal setting for morning coffee, summer gatherings, or simply unwinding at the end of the day. Lovingly maintained and ready for its next chapter, this home offers comfort, versatility, and lasting value.

3 Beds ⋅ 1 Baths ⋅ 24185086 MLS

*Deadline set of Tuesday 6/30 at Noon. Seller reserves the right to take an offer at anytime.* Nestled on a well maintained lot, this charming Cape offers the perfect balance of privacy and convenience. Set just off the beaten path, the property enjoys a peaceful, rural feel while remaining close to shopping, dining, and everyday amenities. Thoughtfully updated over the years, improvements include vinyl siding, a 10-yr old roof, many newer windows, and numerous interior enhancements, creating a low-maintenance, move-in-ready home. The flexible floor plan features an open-concept kitchen, living, and dining area, a spacious first-floor primary bedroom, and two generously sized bedrooms on the upper level that can also serve as a home office, playroom, or guest space to fit your needs. Step outside to the expansive 14' x 18' deck overlooking the backyard-an ideal setting for morning coffee, summer gatherings, or simply unwinding at the end of the day. Lovingly maintained and ready for its next chapter, this home offers comfort, versatility, and lasting value.

111 Moore Ave, Winchester

$300,000

This Highland Lake house is in great condition, remodeled 4 years ago. Lower level has a separate entrance and was revamped with large living room and full bathroom. Walk to the Association beach in 5 mins.

3 Beds ⋅ 2 Baths ⋅ 24150574 MLS

This Highland Lake house is in great condition, remodeled 4 years ago. Lower level has a separate entrance and was revamped with large living room and full bathroom. Walk to the Association beach in 5 mins.

230 E Wakefield Blvd, Winchester

$290,000

Welcome to this beautifully updated single-level home offering the ease of one-floor living. This charming property features two spacious bedrooms and an updated full bathroom, along with a generously sized living room perfect for relaxing or entertaining. The renovated kitchen boasts modern finishes and stainless steel appliances, providing both style and functionality. A heated sunroom adds valuable extra living space and leads directly to the backyard, ideal for enjoying the outdoors year-round. Additional highlights include gas heat, central air, and replacement windows throughout. This property is truly turn key! HIGHEST AND BEST DUE MONDAY 5/4/26 @12NOON

2 Beds ⋅ 1 Baths ⋅ 24170791 MLS

Welcome to this beautifully updated single-level home offering the ease of one-floor living. This charming property features two spacious bedrooms and an updated full bathroom, along with a generously sized living room perfect for relaxing or entertaining. The renovated kitchen boasts modern finishes and stainless steel appliances, providing both style and functionality. A heated sunroom adds valuable extra living space and leads directly to the backyard, ideal for enjoying the outdoors year-round. Additional highlights include gas heat, central air, and replacement windows throughout. This property is truly turn key! HIGHEST AND BEST DUE MONDAY 5/4/26 @12NOON

149 E Mountain Ave, Winchester

$285,000

Fully remodeled from top to bottom, 350 Walnut St offers the perfect blend of modern updates, efficient living, and outdoor space. This move-in-ready 2-bedroom, 1-bath ranch has been beautifully reimagined with a fresh, stylish feel and all the major improvements already done for you. Inside, you will find a brand-new kitchen with quartz countertops and stainless-steel appliances, a fully updated bathroom, oak floors, new windows, new roof, new mechanicals, new electrical, and new plumbing. Built in 1950, this home offers 720 square feet of thoughtfully designed living space that feels comfortable, practical, and easy to maintain. A full basement with garage access and a 1-car attached garage adds valuable storage and utility, while natural gas heat adds everyday convenience. Set on an oversized 0.56-acre lot, this property offers a rare size of land for a home of this size, giving you room to relax, garden, entertain, or simply enjoy having open space around you. Its location near Tatro Park and local recreation adds to the appeal, making it easy to enjoy the outdoors close to home. Whether you are a first-time purchaser, downsizing, or looking for a turnkey alternative to condo living, this home delivers exceptional value. Why rent or settle when you can own a fully renovated single-family home with land, a garage, and major system updates already completed? Small in size but big on quality, comfort, and lifestyle, this is a home that is easy to love.Photos enhanced

2 Beds ⋅ 1 Baths ⋅ 24170101 MLS

Fully remodeled from top to bottom, 350 Walnut St offers the perfect blend of modern updates, efficient living, and outdoor space. This move-in-ready 2-bedroom, 1-bath ranch has been beautifully reimagined with a fresh, stylish feel and all the major improvements already done for you. Inside, you will find a brand-new kitchen with quartz countertops and stainless-steel appliances, a fully updated bathroom, oak floors, new windows, new roof, new mechanicals, new electrical, and new plumbing. Built in 1950, this home offers 720 square feet of thoughtfully designed living space that feels comfortable, practical, and easy to maintain. A full basement with garage access and a 1-car attached garage adds valuable storage and utility, while natural gas heat adds everyday convenience. Set on an oversized 0.56-acre lot, this property offers a rare size of land for a home of this size, giving you room to relax, garden, entertain, or simply enjoy having open space around you. Its location near Tatro Park and local recreation adds to the appeal, making it easy to enjoy the outdoors close to home. Whether you are a first-time purchaser, downsizing, or looking for a turnkey alternative to condo living, this home delivers exceptional value. Why rent or settle when you can own a fully renovated single-family home with land, a garage, and major system updates already completed? Small in size but big on quality, comfort, and lifestyle, this is a home that is easy to love.Photos enhanced

350 Walnut St, Winchester

$280,000

Well-maintained and move-in ready, this charming one-level ranch offers 912 square feet of comfortable living space with 2 bedrooms and 1 full bath. Features include a one-car garage and convenient main-level laundry. The functional layout offers easy one-level living. Conveniently located close to town and local amenities. A great opportunity for buyers looking for a manageable home in a convenient location.

2 Beds ⋅ 1 Baths ⋅ 24202478 MLS

Well-maintained and move-in ready, this charming one-level ranch offers 912 square feet of comfortable living space with 2 bedrooms and 1 full bath. Features include a one-car garage and convenient main-level laundry. The functional layout offers easy one-level living. Conveniently located close to town and local amenities. A great opportunity for buyers looking for a manageable home in a convenient location.

1 Division St, Winchester

$280,000

Excellent opportunity for investors! This well-maintained Victorian-style two-family home offers the perfect blend of character, functionality, and income potential. Each spacious unit features 5 rooms, 2 bedrooms, and 1 full bath, with beautiful hardwood flooring throughout and separate, efficient natural gas heating systems. The upper-level apartment also includes a charming enclosed porch, providing additional seasonal living space and a relaxing retreat. Outside, you'll find a level lot and a unique two-story barn with a full basement, offering exceptional storage, workshop space, or endless possibilities for hobbyists and contractors alike. Conveniently located just minutes from downtown, schools, shopping, dining, and everyday conveniences, this property is ideal whether you're looking to build your investment portfolio or live in one unit while generating rental income from the other. A rare opportunity to own a versatile multi-family property with timeless Victorian charm!

4 Beds ⋅ 2 Baths ⋅ 24194728 MLS

Excellent opportunity for investors! This well-maintained Victorian-style two-family home offers the perfect blend of character, functionality, and income potential. Each spacious unit features 5 rooms, 2 bedrooms, and 1 full bath, with beautiful hardwood flooring throughout and separate, efficient natural gas heating systems. The upper-level apartment also includes a charming enclosed porch, providing additional seasonal living space and a relaxing retreat. Outside, you'll find a level lot and a unique two-story barn with a full basement, offering exceptional storage, workshop space, or endless possibilities for hobbyists and contractors alike. Conveniently located just minutes from downtown, schools, shopping, dining, and everyday conveniences, this property is ideal whether you're looking to build your investment portfolio or live in one unit while generating rental income from the other. A rare opportunity to own a versatile multi-family property with timeless Victorian charm!

64 Wheeler St, Winchester

$276,000

Step into the charm of this 1880 Colonial, featuring 4 bedrooms and 1.5 baths, just a short walk to the shops, dining, and conveniences of downtown. The main level offers a spacious eat-in kitchen, inviting living room, and a versatile bonus room that could serve as a home office or, with a little creativity, an additional bedroom, along with a half bath for added convenience. Upstairs includes four comfortable bedrooms, a full bath, and a walk-up attic offering great storage or future potential. Outside, enjoy an open lot with plenty of off-street parking, a ground-level deck/patio for entertaining, and a brick fire pit-perfect for relaxing evenings. A covered front porch and classic details add to the home's timeless appeal.

4 Beds ⋅ 2 Baths ⋅ 24167580 MLS

Step into the charm of this 1880 Colonial, featuring 4 bedrooms and 1.5 baths, just a short walk to the shops, dining, and conveniences of downtown. The main level offers a spacious eat-in kitchen, inviting living room, and a versatile bonus room that could serve as a home office or, with a little creativity, an additional bedroom, along with a half bath for added convenience. Upstairs includes four comfortable bedrooms, a full bath, and a walk-up attic offering great storage or future potential. Outside, enjoy an open lot with plenty of off-street parking, a ground-level deck/patio for entertaining, and a brick fire pit-perfect for relaxing evenings. A covered front porch and classic details add to the home's timeless appeal.

57 Bridge St, Winchester

$274,900

Opportunity awaits with this versatile 3-family property located at 69 Prospect Street in Winchester, perfect for both investors and owner-occupants alike. Whether you're looking to expand your investment portfolio or offset your mortgage with rental income, this multi-family offers flexibility, functionality, and strong potential in a convenient location. The property features 3 separate units with spacious layouts and off-street parking made easy with two driveways. Unit 1 includes in-unit laundry hookups, adding everyday practicality and additional appeal for renters. A newer roof offers peace of mind, while the layout of the property provides opportunities for long-term rentals, owner occupancy, or future value-add potential. Located just minutes from downtown Winsted, tenants can enjoy close proximity to local restaurants, coffee shops, grocery stores, and everyday conveniences. Outdoor enthusiasts will appreciate being near Highland Lake, the Sue Grossman Still River Greenway, and scenic hiking trails throughout the Litchfield Hills region. The property also offers easy access to Route 8 for commuting to Torrington, Canton, and surrounding towns. With strong rental demand, multiple income-producing units, and a location that blends small-town charm with convenience, this is a fantastic opportunity.

7 Beds ⋅ 3 Baths ⋅ 24173658 MLS

Opportunity awaits with this versatile 3-family property located at 69 Prospect Street in Winchester, perfect for both investors and owner-occupants alike. Whether you're looking to expand your investment portfolio or offset your mortgage with rental income, this multi-family offers flexibility, functionality, and strong potential in a convenient location. The property features 3 separate units with spacious layouts and off-street parking made easy with two driveways. Unit 1 includes in-unit laundry hookups, adding everyday practicality and additional appeal for renters. A newer roof offers peace of mind, while the layout of the property provides opportunities for long-term rentals, owner occupancy, or future value-add potential. Located just minutes from downtown Winsted, tenants can enjoy close proximity to local restaurants, coffee shops, grocery stores, and everyday conveniences. Outdoor enthusiasts will appreciate being near Highland Lake, the Sue Grossman Still River Greenway, and scenic hiking trails throughout the Litchfield Hills region. The property also offers easy access to Route 8 for commuting to Torrington, Canton, and surrounding towns. With strong rental demand, multiple income-producing units, and a location that blends small-town charm with convenience, this is a fantastic opportunity.

69 Prospect St, Winchester

$270,000

Perched on desirable Wallens Hill with beautiful western sunset views, this lovingly maintained 3 bed 1957 ranch is full of warmth, charm, and pride of ownership. Bright and sunny throughout, the home offers 1,008 square feet of comfortable living space with hardwood floors, central air conditioning, and an easy-flow layout designed for everyday living. The spacious eat-in kitchen features oak cabinetry, abundant workspace, and a welcoming atmosphere perfect for gathering. A cozy three-season porch provides the ideal place to enjoy your morning coffee or unwind at the end of the day while overlooking the peaceful backyard. Outside, the gently tapered yard is a gardener's dream with mature perennial plantings, space for raised beds, and room to relax on the rear platform deck. The dry lower level includes laundry, interior access to the garage, and added convenience for bringing in groceries and storage. Clean, efficient, and beautifully cared for, this adorable ranch offers timeless character and broad appeal for buyers seeking comfort, simplicity, and a truly move-in ready home in the heart of Winchester. Don't miss this!

3 Beds ⋅ 1 Baths ⋅ 24172219 MLS

Perched on desirable Wallens Hill with beautiful western sunset views, this lovingly maintained 3 bed 1957 ranch is full of warmth, charm, and pride of ownership. Bright and sunny throughout, the home offers 1,008 square feet of comfortable living space with hardwood floors, central air conditioning, and an easy-flow layout designed for everyday living. The spacious eat-in kitchen features oak cabinetry, abundant workspace, and a welcoming atmosphere perfect for gathering. A cozy three-season porch provides the ideal place to enjoy your morning coffee or unwind at the end of the day while overlooking the peaceful backyard. Outside, the gently tapered yard is a gardener's dream with mature perennial plantings, space for raised beds, and room to relax on the rear platform deck. The dry lower level includes laundry, interior access to the garage, and added convenience for bringing in groceries and storage. Clean, efficient, and beautifully cared for, this adorable ranch offers timeless character and broad appeal for buyers seeking comfort, simplicity, and a truly move-in ready home in the heart of Winchester. Don't miss this!

104 Maloney Ct, Winchester

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