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$330,000
3 Beds 1 Baths 24095586 MLS
Charming Country Cape with Cottagecore appeal on just over an acre of land and situated on a culd-de-sac. Located off the beaten path in the quiet hills of Winchester, this storybook Cape-style home offers the perfect blend of rustic charm and modern comfort. Convenient to Route 8 and just minutes to town amenities. Enjoy the natural beauty surrounding the property while relaxing on the deck and patio - plenty of yard space for play, gardening and more. Inside, you will fall in love with the cozy cottagecore decor and large windows that flood the home with natural light - hardwood flooring throughout. The spacious family room invites gatherings year-round, with a wood stove providing warmth and ambiance during New England's cooler months. Spacious eat-in kitchen makes meal preparation a breeze. Another room on the main level being used as an office with door can easily be transformed to a Formal Dining Room. The upper level offers 3 bedrooms and a full-bath, and the walk-out basement offers finished space perfect for your recreational activities; ideal hobby space or home gym. The home is equipped with a tankless propane hot-water heater and it is generator ready. Whether you're enjoying the quiet from the back deck, soaking in the sunlit interiors, or exploring the surrounding nature, this home is a rare find in a serene setting!

50 Manchester Hts, 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

$324,900
4 Beds 2 Baths 24134631 MLS
Welcome to 135-137 Elm Street! This well-maintained two-family home offers an excellent opportunity for owner-occupants or investors alike. The main level unit features 5 rooms, including 2 bedrooms and 1 full bath, and is in excellent condition. It's equipped with a natural gas warm-air furnace that also provides central air for year-round comfort. The second-floor unit mirrors the first-floor layout with 5 rooms, 2 bedrooms, and 1 full bath, but includes additional finished space on the third level, offering several more rooms and a second full bath-the perfect setup for a 4-bedroom, 2-bath unit or flexible living arrangements. A detached two-car garage adds convenience and storage space, and the property's location offers easy access to downtown amenities, shopping, restaurants, and area schools. Whether you're looking to live in one unit and rent the other or add to your investment portfolio, this versatile property is a great find in a convenient location.

135 Elm St, 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

$320,000
4 Beds 2 Baths 24138604 MLS
Welcome to this Wonderful Historic Colonial Farmhouse.. This home has been lovingly remodeled with many of the original features still intact. This home offers a large kitchen with newer counters open to the dining area and is complete with a fireplace. Living room is generous sized, it's filled with light, exposed beams and hardwood floor. On this level you'll also find 2 bedrooms and a fully remodeled bath. As well as a extra large Mudroom with laundry hookups and wide boards floors...You'll gain access to the upper floor VIA a gorgeous open staircase, and there you'll find the Large primary bedroom with walkin closet and sitting area. On this level you'll find another bedroom and a full bathroom which also has been remodeled with walkin shower and a beautiful claw foot tub. There is second staircase also... Throughout this home you'll find gleaming hardwood floors, original hand hewn beams, newer windows, vinyl siding, generator ready, well pump, and newer hot water heaters (one gas, one electric) There's a 2 car detached garage with electric, outdoor shower, above ground pool (needs liner) and 2 sheds and the sweetest little porch to enjoy your free time.. All set on 1.85acreas. This is truly a country setting with easy access to highways, to get you to any major city you may need including Hartford, Boston, or NYC..Come see it now.. Being Sold As-IS .. Subject to probate approval.

148 Danbury Quarter Rd, Winchester

$315,000
3 Beds 2 Baths 24106598 MLS
Nestled in the charming New England town of Winsted, this classic three-bedroom, two-bathroom home at 17 Adams Street offers a blend of traditional charm and comfortable living. The property boasts a welcoming exterior with a distinguished facade, a covered front porch, and a well-maintained lawn, all framed by mature trees that provide a sense of privacy and tranquility. A convenient driveway leads to a detached garage, offering ample parking and storage. Step inside to discover a thoughtfully laid out interior. The living spaces are adorned with light-colored walls and beautiful hardwood flooring, creating an inviting and airy atmosphere. The spacious living room, featuring multiple windows that bathe the room in natural light, is an ideal spot for relaxation and entertaining, and is large enough to accommodate a substantial sectional sofa. The adjacent dining room, equally bright and inviting, provides a generous space for family meals and gatherings. It boasts hardwood floors, a classic chandelier, and is conveniently located with easy access to other areas of the home, including what appears to be a well-appointed kitchen. The dining room also opens onto a fantastic rear deck, perfect for al fresco dining and enjoying the lush, treed surroundings under the shade of an awning. One of the bedrooms, currently set up as a home office, offers versatility and function with its warm yellow walls, hardwood flooring, and ample natural light from two windows

17 Adams St, Winchester

$310,000
2 Beds 2 Baths 24126058 MLS
Well-maintained and move-in ready, this charming one-level ranch offers 900 square feet of comfortable living just steps from Highland Lake. Featuring 2 bedrooms and 2 full bathrooms, this home is perfect as a full-time residence, weekend retreat, or summer getaway. Enjoy lake living without the high taxes, with public water and sewer already in place. The property includes a private backyard perfect for entertaining, along with a separate right-of-way providing easy access and ample parking for boats, trailers, or multiple vehicles. Relax on the front porch and soak in the peaceful surroundings. Located in a quiet lakeside community on East Lake Street next just up the road from the Highland Lake Marina, with public beach access and boat launch nearby, this meticulously kept property offers an unbeatable combination of convenience, comfort, and outdoor recreation.

152 E Lake 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
2 Beds 2 Baths 24126922 MLS
Nestled in the scenic Litchfield Hills, this charming 2-bedroom, 1.5-bath Cape has been lovingly restored over the past 11 years and thoughtfully updated with room to expand. Combining modern convenience with timeless character, improvements & remodeling include electrical upgrades, replacement of the majority of the windows in the house, insulation, newer appliances, a new back door, refinished hardwood floors and fresh paint throughout, making it truly move-in ready. Cozy up by the wood-burning stove on crisp autumn nights, or enjoy sun-filled days in the bright and inviting sunroom. Sitting on a full acre, the property offers ample space for outdoor living, gardening, and entertaining. Energy-efficient upgrades such as Thermopane windows and added insulation ensure comfort in every season. Located in the welcoming community of Winsted, you'll be close to Highland Lake, Beardsley Library, local parks, the town's vibrant mural project, community events, a local brewery, restaurants, shops, and the community college. Schedule your private showing today.

331 Colebrook Rd, Winchester

$290,000
3 Beds 2 Baths 24130085 MLS
Seller is working on final details. Welcome to your dream home, 39 Orchard st ! This beautifully updated colonial offers the ideal combination of timeless architecture and contemporary comfort, all situated on a fantastic private lot. As you step inside, you are greeted by the warm glow of refinished hardwood floors, The living room is inviting and bright, leading you into a dining area perfect for family gatherings. Upstairs, you'll find three comfortable bedrooms, all serviced by a stylishly renovated full bathroom. A convenient half-bath on the main floor adds to the home's functionality. However, the true masterpiece lies outside. Step through the back door to discover your own private oasis-an oversized beautiful yard that promises endless possibilities for summer barbecues, gardening, or simply relaxing in your own serene space. It's a rare find of this size and privacy. Don't miss on this great opportunity and make this home yours.

39 Orchard St, 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

$277,000
4 Beds 1 Baths 24108213 MLS
This Home is Modern day updates Meets Old World Charm...The Updated Kitchen offers granite counter tops, custom cabinetry, tile flooring, and a pantry with Washer/ dryer hookups for convenience.. You'll find a formal dining room with hardwood floors, A main level bedroom, large living room with French doors and open stair case that leads to the upstairs.. Also on the Main level you'll find a completely remodeled Bathroom, with tile flooring, granite countertop and walk-in shower, As well as a sunroom/den for those quiet times. Upstairs you'll find 3 bedrooms all with hardwood floors, and a walk up attic . Windows have been updated..There is enough space to add a second bath if needed. This home has a enclosed back porch which would make a great mud room or whatever else you may need... The yard is completely fenced with custom gates. There is a generous 2 car Heated garage which has also been completely finished with beautiful tongue and grove paneling, recessed lighting , pull down attic space.. Best Man cave or she shed you could ask for!!! In addition to that there is a an oversize shed which is also heated for all the toys you may have. also has Hot and Cold water spigots outside, and a generator which is already installed...And all of this still leaves you plenty of room for parking.. In a matter of a few minutes you can find yourself at the Beautiful Highland Lake.. Home is part of Estate, Sold As-IS , And is subject to probate approval.

12 Cherry St, Winchester

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