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$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

$270,000
3 Beds 1 Baths 24116065 MLS
Welcome to this well-maintained 3-bedroom, 1-bathroom home located on a quiet street in the heart of Winsted. Offering 1,058 square feet of comfortable living space, this home features beautiful hardwood floors throughout and a practical layout ideal for everyday living. The kitchen includes a gas range, and the home is equipped with efficient natural gas heating and hot water, helping to keep utility costs low year-round. An extra refrigerator with freezer in the basement adds convenience and storage flexibility. Step outside to a spacious backyard perfect for entertaining, complete with a private patio area and a quality wood storage shed for your tools or seasonal items. The large, level yard offers plenty of room for gatherings, gardening, or play. The roof is only 5 years old, offering peace of mind and reduced maintenance. Whether you're enjoying a quiet evening on the patio or hosting for entertainment, this home has everything you need in a convenient and welcoming location.

22 Stanton Ave, Winchester

$270,000
2 Beds 1 Baths 24126092 MLS
Beautifully updated Raised- Ranch retreat on 1.33 wooded acres! Nestled in a serene, natural setting yet conveniently close to local amenities. When you enter the home you will find two generous sized rooms with new vinyl plank flooring, fresh paint & a mini split as well as a spacious storage/utility room with laundry. The main floor includes the living room with a stone accent wall & great views out the front window! There is a large, updated eat-in kitchen with quartz counters, stainless steel appliances, with a gas stove to impress the cook! Sliders give you access to the large deck & privacy! There is a large primary bedroom with fresh paint & a new mini split.(Primary was 2 rooms) A 2nd bedroom with a beautiful accent wall & new mini split. The full bath has been painted & a new vanity installed.

101 Norfolk Rd, 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

$261,000
1 Beds 1 Baths 24119905 MLS
Welcome to 115 Laurel Way! Tucked away in a peaceful neighborhood surrounded by nature, this charming well maintained 1-bedroom, 1-bathroom home offers the perfect blend of comfort and serenity. Set on just over half an acre, the property provides ample space for outdoor living. Imagine relaxing by a cozy fire pit, enjoying warm evenings under the stars, or simply soaking in the natural beauty all around. Inside, you'll find beautiful hardwood floors throughout, complementing the cozy layout. With central air and natural gas for heating, comfort is guaranteed year-round. The shed is a standout feature, offering electricity and a mini-split unit for cooling. This versatile space can serve as a workshop, storage area, or even a guest suite-the possibilities are endless. Located just minutes from Highland Lake, shopping, dining, and entertainment, this home offers a perfect balance of tranquility and convenience. Don't miss the opportunity to experience this hidden gem-schedule your showing today!

115 Laurel Way, Winchester

$260,000
3 Beds 3 Baths 24133158 MLS
New to the market! Check out this upgraded colonial home with 3 bedrooms and 2.5 baths located on a 2.6-acre wooded lot with a patio, shed and paths for walking and quadding. Enjoy entertaining in the open layout with an eat in kitchen and new cabinets. Relax in the cozy living room with hard wood floors, a fireplace and a sliding glass door to the back deck. Keep in mind the formal dining room can also be used as a playroom or home office. Let's move to the upstairs master bedroom which has a fully renovated bathroom including a jetted tub. A combined half bath/laundry room adds functionality to the main level. A convenient walkout basement is equipped with a workbench and plenty of shelves for storage. Don't miss out on this one!

73 Norfolk Rd, 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

$250,000
4 Beds 2 Baths 24146596 MLS
Highest and best 1/4/26 by 5pm Welcome to 43 Wallens Street in the heart of Winsted - a versatile two-family property ideal for owner-occupants, investors or an in law. The first-floor unit offers a one-bedroom layout with recessed lighting, while the spacious second unit features three bedrooms, including one on the main level and two on the upper floor, plus an additional room on the main level perfect for a home office or flex space. An inviting all-season porch with a wood stove welcomes you upon entry. Interior features include a combination of hardwood flooring and carpeting, and the property has been freshly painted throughout. Outside, enjoy a two-car garage, along with a shed providing excellent storage and utility. Conveniently located near Northwestern Connecticut Community College, medical facilities, and Highland Lake, with easy access to shopping, parks, and commuter routes. A great opportunity to own a well-located multi-family home in Winchester.

43 Wallens St, Winchester

$250,000
2 Beds 2 Baths 24144757 MLS Clockmakers Hill BLDG.
Discover effortless, low-maintenance living in this inviting home located in the highly sought-after Clockmaker's Hill 55+ community. The thoughtfully designed open floor plan features 2 bedrooms and 2 full bathrooms, offering seamless flow from the spacious living room-anchored by a cozy gas fireplace-to the dedicated dining area, ideal for hosting friends and family. The sun-filled kitchen boasts granite countertops and plenty of workspace, making meal prep a pleasure. The versatile second bedroom, with an adjacent full bathroom and generous closet space, is perfect for guests or can easily serve as a home office or hobby room. Unwind in the spacious primary suite complete with its own private full bath. Additional conveniences include an in-unit laundry closet and an attached one-car garage for year-round comfort. Enjoy your morning coffee or unwind in the evening on the welcoming front porch. Residents of Clockmaker's Hill also enjoy access to a beautifully maintained clubhouse for private gatherings and community events, along with meticulously landscaped grounds. With shopping, dining, and major commuter routes just minutes away, this move-in-ready home offers the perfect blend of comfort, convenience, and community. Embrace the active 55+ lifestyle you've been waiting for!

174 Wallens St Unit APT B6, Winchester

$231,000
2 Beds 1 Baths 24143747 MLS
Perched atop a scenic hill overlooking picturesque Highland Lake, this charming ranch offers 1,051+/- square feet of inviting living space with two bedrooms and two full bathrooms. The galley-style kitchen features Thomasville cabinetry and Corian countertops, opening to an intimate dining room with tranquil lake views. Take your pick of relaxing spaces-whether it's the cozy living room with an exposed beam, the airy sunroom overlooking the water, or the expansive 12x17 Trex deck. You can also unwind in the outdoor hot tub beneath the cabana for year-round enjoyment. Adding to its appeal, this property includes a private boat dock and picnic area, offering direct access to all the recreation Highland Lake provides. Whether you're seeking a vacation getaway or a forever home, this lakeside retreat is truly a must-see.

817 E Wakefield Blvd, Winchester

$230,000
6 Beds 3 Baths 24139930 MLS
Looking to expand your investment portfolio-or live nearly rent-free while building one? This rare 3-family opportunity checks all the boxes! Hard to come by, this multi-family property features long-term, reliable tenants plus a vacant unit ready for an owner-occupant or a new rental. The lower level offers a comfortable 1-bedroom unit with walk-out patio. The main (2nd) level features 2 spacious bedrooms, a large living room, an eat-in kitchen and a 3rd bedroom currently being used as a dining room. The 3rd-floor unit includes 1 bedroom plus a tandem bedroom/dressing room/nursery, a generous living room, and a charming balcony off the kitchen, along with direct access to the walk-up attic for additional storage potential. Tenants share the basement, and off-street parking adds convenience. Located just moments from the hub of Winsted, this property provides easy access to shopping, dining, and local amenities. Tenants are dependable, pay on time, and would love to stay! You will need some sweat equity to bring this multi-family back to its glory days! Being sold "As-Is". Follow this home on finaloffer.com for instant updates and offer alerts. Don't miss this rare chance to secure a strong income-producing asset-or move in and let the rent pay the mortgage!

106 Rockwell St, Winchester

$229,000
2 Beds 2 Baths 24145729 MLS
Move-in ready and thoughtfully updated, this inviting home at 18 Curtice Street offers peace of mind and modern comfort. In 2005, the property was completely stripped to the studs and renovated, including updated plumbing and electrical, roof, kitchen, and baths. The heating system, along with the oil tank, was replaced in 2019. The main living level features a spacious front living room, a large eat-in kitchen with sliders leading to a covered deck overlooking a private rear yard, and a convenient half bath-ideal for everyday living and entertaining. Upstairs, you'll find a generously sized primary bedroom with a walk-in closet, a second bedroom, a full bath, and laundry. Ideally located with easy access to schools, recreation, and all that the downtown area has to offer, this home combines quality updates with a desirable setting.

18 Curtice St, Winchester

$227,500
1 Beds 2 Baths 24119179 MLS Clockmaker's Hill BLDG.
Discover effortless living in this inviting home at the sought-after Clockmaker's Hill community. The thoughtfully designed open floor plan creates seamless flow from the spacious living room-anchored by a cozy gas fireplace-to the dedicated dining room, perfect for hosting friends and family. The sun-drenched kitchen features a convenient breakfast bar for casual dining and morning coffee. The versatile den with adjacent full bathroom and generous closet storage offers flexibility as a home office, hobby room, or guest space. Retreat to the spacious primary bedroom suite with its spacious full bathroom. Practical conveniences include an in-unit laundry closet and attached one-car garage for year-round comfort. Step onto your welcoming front porch to enjoy morning coffee or evening relaxation. As a Clockmaker's Hill resident, you'll have access to the elegant clubhouse for private gatherings and community events, plus beautifully maintained landscaped grounds. This prime location puts shopping, dining, and major commuting routes just minutes from your door. Ready to embrace the active 55+ lifestyle? This move-in-ready home offers the perfect blend of comfort, convenience, and community.

174 Wallens St Unit APT H1, Winchester

$225,000
2 Beds 2 Baths 24154885 MLS
Fully renovated 1870 Colonial offering 1,172 sq. ft. of thoughtfully updated living space that blends historic character with modern comfort. Hardwood floors run through the living room and both bedrooms, creating a warm and inviting feel. The flexible layout includes a convenient first-floor bedroom and a spacious primary bedroom on the second level. The bright, refreshed kitchen features new flooring, skylights that fill the eat-in area with natural light, and all-new stainless steel appliances. A first-floor laundry room adds everyday convenience and includes a remodeled half bath, while the full bathroom has also been completely updated with clean, modern finishes, with the antique, refinished tub. Fresh interior paint and all-new lighting throughout provide a crisp, move-in-ready atmosphere. Extensive improvements offer lasting value and peace of mind, including a new gas furnace, new vinyl siding, new roof on the addition, new wood front porch, new deck, and new lighting throughout the home-enhancing both efficiency and outdoor enjoyment. Ideally located close to shopping, restaurants, and major highway access, this home delivers updated living in a convenient setting. A great opportunity for buyers seeking a fully renovated home and low maintenance yard, with nothing left to do but move in.

9 John St, Winchester

$225,000
2 Beds 1 Baths 24110201 MLS
Step right into effortless living with this charming 2bedroom ranch-style home, nestled right in town and wrapped in durable, lowmaintenance vinyl siding. As you approach, you'll appreciate the tidy curb appeal and generous driveway-perfect for guests or extra vehicles. Inside, an open concept living and dining area welcomes you with abundant natural light and easy flow, ideal for both everyday comfort and casual entertaining. The adjacent kitchen boasts ample cabinetry and counter space, ready for your personal touch. Descend to the full, partially finished walkout basement, where potential abounds: imagine a cozy media room, a home office, or a hobby workshop-and still plenty of room left for storage. Rear Deck, seamlessly extends your living space outdoors. Behind that, discover a spacious backyard oasis-ideal for summer barbecues, garden projects, or simply unwinding under the sky. Perfect for first time buyers, down sizers, or anyone seeking single level convenience with space below, this home combines in town convenience (shops, schools, and cafes just minutes away) with room to grow. Don't miss your chance to make this versatile ranch your very own-schedule a showing today!

130 Stanton Ave, Winchester

$205,000
2 Beds 2 Baths 24173166 MLS Green Ridge BLDG.
SELLER REQUESTS ALL OFFERS BY SATURDAY, MAY 9TH @ 5:00 Have I got a home for you! Unpack and relax in this rarely available condo, the perfect spot for you. With easy access to the highway and a quaint downtown area filled with restaurants and shops, this two-bedroom unit offers plenty of room to breathe. The cozy kitchen comes equipped with ample cabinetry and a brand new gas stove. You can store all your small appliances in the large pantry and interact with guests while cooking dinner through the opening that overlooks the combined dining and living room. Sunlight pours in through the sliding door, leading you to your brand new deck-perfect for enjoying your morning coffee while taking in the wooded backyard. The first-floor primary bedroom features a large closet and easy access to a completely renovated bathroom, which boasts a beautiful walk-in shower. Just up the stairs is a second bedroom and another renovated full bath with trendy fixtures. Need more space? Head up to the loft area with skylights, which makes for a great office, TV room, or yoga space to unwind. There's also a full basement that includes a new hot water heater and furnace, along with additional closet space. This area is perfect for finishing as an additional game room! This is not a drive-by and will not last long. Schedule your viewing today!

111 Torringford St Unit 7, Winchester

$204,000
2 Beds 2 Baths 24174220 MLS
Tucked within the desirable Green Ridge community, this inviting townhouse-style condo offers comfortable living with thoughtful updates and flexible space throughout. Featuring 2 bedrooms and 2 bathrooms, this home blends functionality, warmth, and opportunity for a new owner to make it their own. The updated kitchen serves as the centerpiece of the home, offering modern finishes, ample cabinet space, and an open flow into the dining and living areas, making everyday living and entertaining easy. The living room opens to a private deck overlooking a peaceful wooded backdrop, creating a quiet retreat for morning coffee or evening relaxation. Upstairs, the spacious loft provides excellent versatility for a home office, guest space, or additional lounge area. The partially finished lower level adds even more usable square footage and can easily serve as a media room, fitness area, playroom, or hobby space. While the bathrooms retain a more traditional style, they offer solid functionality and the perfect opportunity for future customization and added value. Conveniently located near shopping, restaurants, recreation, and Route 8 access, this condo combines low-maintenance living with space, privacy, and potential in one of Winchester's well-established communities.

111 Torringford St Unit 33, Winchester

$185,000
4 Beds 2 Baths 24176921 MLS
Located in the charming community of Winsted, this 4-bedroom home is tucked away in a quiet, low-traffic neighborhood while still being close to many local amenities. Hardwood floors run throughout the home, adding warmth and character, and the tree-lined backyard offers a private outdoor setting to enjoy year round. This home also features a beautiful enclosed second-floor sun porch, perfect for relaxing with morning coffee, reading, or enjoying the changing seasons. A large walk-up attic provides abundant storage space and may offer the potential to be finished for additional living area, office space, or a hobby room. Just a short distance away, you will find the local library, coffee shops, parks, restaurants, and a variety of neighborhood shops and conveniences. Outdoor enthusiasts will appreciate nearby Highland Lake, offering opportunities for boating, swimming, and recreation throughout the warmer months. This home does need some TLC and updating, but with vision and effort, it has the potential to truly shine. Whether you are looking for a primary residence or an investment opportunity, this property offers excellent potential in a desirable location. **Audio & Video surveillance present**

30 Upland Rd, Winchester

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