Refine Search
Map
Sort by
$387,500
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
$370,000
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
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
$368,500
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
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
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
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
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
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
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
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
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
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
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
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
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
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
$316,000
3 Beds ⋅ 2 Baths ⋅ 24150993 MLS
Enjoy easy one-level living in this charming 3-bedroom, 2-bath home offering an eat-in kitchen, hardwood floors throughout, a full basement, garage, and a primary bedroom with its own bath. The yard provides great outdoor space for relaxing or entertaining, all just minutes from Winsted Center, Route 8, and Route 44. View the property during open houses only Saturday 2/2/26 and Sunday 2/8/26 from 12-2 Highest and Best by Wednesday 2/11/26 at 5pm

95 Colony Dr, Winchester
$315,000
3 Beds ⋅ 3 Baths ⋅ 24131214 MLS
Don't miss this unique opportunity to own a multi family residential property and an office space! (Owner currently has permission from the town to create a 2nd residential unit on the first floor) - will have 2.5 baths when completed. Great central location close to all amenities that Winsted has to offer including restaurants, parks, college, public transportation and shopping. First floor available "as is" without being completed. Includes 2 electric meters; one up and 1 down and two 50 gallon hot water tanks. Tenants lease expires 9/2027. Also listed as Commercial MLS#24131211.

25 Center St, Winchester
$305,000
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
2 Beds ⋅ 3 Baths ⋅ 24153820 MLS ⋅ Clockmaker's Hill BLDG.
Welcome to Clockmakers Hill, a desirable and active 55+ community offering comfort, convenience, and vibrant living. This immaculately maintained 2 bedroom, 2.5 bath condo blends thoughtful updates with everyday functionality. Warm wood flooring enhances the main living areas, while the kitchen features tile flooring, granite countertops, stainless steel appliances, and a pantry customized with California Closets. Brand new appliances including the refrigerator, microwave, and dishwasher make this home truly move in ready. The inviting living room boasts a stunning fireplace with a new gas insert and elegant stone surround, creating a cozy focal point. Recent upgrades also include a new HVAC system and water heater for added efficiency and peace of mind. The spacious primary suite offers a walk in closet designed with California Closets and a private en suite bath. The second bedroom, currently used as a home office, can easily convert back to a bedroom or additional living space. A spacious lower level provides exceptional flexibility, complete with a full bath and laundry area ideal for guests, recreation, and additional living space. The garage offers generous storage and room for a home gym, and the driveway accommodates two additional vehicles. Enjoy access to the beautifully maintained clubhouse and landscaped grounds. Conveniently located near shopping, dining, and major highways, this immaculate home offers the perfect blend of comfort, upgrades, and easy living.

174 Wallens St Unit APT A5, Winchester
$300,000
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
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
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
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
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
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
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
$266,000
3 Beds ⋅ 2 Baths ⋅ 24153231 MLS
Welcome to this adorable, solidly built Cape in the heart of Winchester, Connecticut-where home is more than just a place, it's a way of life. Nestled in the scenic Litchfield Hills, Winchester is a community full of character, rich history, and strong local businesses, offering a wonderful quality of life. From excellent schools and charming downtown shops to beautiful lakes and outdoor recreation, you'll love everything this area has to offer. This inviting home features 3 bedrooms and 2 baths, blending comfort with classic New England charm. The layout offers warm, livable spaces perfect for everyday living or entertaining. A one-car garage with additional storage provides extra convenience for hobbies, seasonal gear, or workshop space. Whether you're relaxing at home or exploring the surrounding lakes, trails, and community events, this property offers the perfect balance of charm, functionality, and location. A wonderful opportunity to make Winchester your home. This home features 3 bedrooms, 2 baths, and a one-car garage with extra storage, combining comfort with classic New England charm. A perfect place to settle in and enjoy everything Winchester has to offer.

9 Central Ave, Winchester
$255,000
3 Beds ⋅ 1 Baths ⋅ 24158795 MLS
Welcome to this charming New England Colonial that blends classic character with comfortable living. Step inside to an inviting, oversized living room featuring beautiful new vinyl flooring-perfect for relaxing, entertaining guests, or gathering with family. The main living level offers two convenient bedrooms and a laundry area, making everyday living easy and practical. Upstairs, you'll find two additional bedrooms that provide flexible space for family, guests, a home office, or hobbies. Outside, the backyard truly shines through the seasons, offering a peaceful setting to enjoy spring blooms, summer gatherings, colorful fall foliage, and quiet winter views. With its warm layout, timeless Colonial style, and inviting spaces inside and out and easy heating with natural gas, this home offers the perfect blend of New England charm and everyday functionality.

94 Holabird Ave, Winchester

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.