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94 Holabird 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

111 Riverton Road Unit 79, Winchester
$222,000
2 Beds ⋅ 2 Baths ⋅ 24209492 MLS ⋅ Riverwalk BLDG.
A Stylish two-bedroom one and half bath condo featuring numerous updates that makes this an inviting comfortable home. The remodeled kitchen offers a fresh, modern space for cooking, newer flooring adds style though out the main living area. Additional updates are the three energy saving split units for A/C and heating plus an additional source of heat is the pellet stove. Two new sliders open out to private deck, wonderful for enjoying a beverage or just the outdoors. A well maintained move in ready condo offering comfortable low-maintenance living with many of the update already completed. There is always something for you to do in the area, entertainment, restaurants and an easy distance to RT 8. FINAL & BEST BY 5:30 10/5/26

111 Riverton Road Unit 79, Winchester

111 Torringford St Unit 7, 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

111 Torringford St Unit 33, 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

30 Upland Rd, 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

21 Riveredge Dr Unit 21, Winchester
$172,500
2 Beds ⋅ 2 Baths ⋅ 24201953 MLS ⋅ Stillriver Commons BLDG.
Move right into this beautifully updated 2-bedroom, 1.5-bath townhouse tucked away in a small, quiet community with a peaceful setting overlooking the Still River. The thoughtfully updated interior features a renovated kitchen with newer appliances, smart thermostats, fresh paint, and newer flooring throughout. The full bath has also been refreshed with a newly updated shower and new plumbing. The spacious living room offers oversized sliders that open to a paved, private patio-an ideal spot to relax and enjoy the tranquil river views. Additional features include a private garage with a storage room and an assigned parking space. Conveniently located with easy access to Route 8, grocery stores, and downtown Winsted, while also putting you close to Highland Lake, West Hill Lake, the Farmington River, and numerous hiking trails. A wonderful opportunity to enjoy low-maintenance living in a peaceful setting while staying close to everything you need!

21 Riveredge Dr Unit 21, Winchester

34 Hannifin Rd, Winchester
$110,000
3 Beds ⋅ 1 Baths ⋅ 24171237 MLS
Set on 1.8 private acres amid the scenic rolling hills of Winsted, this circa-1850 home offers a rare opportunity to restore and reimagine a property rich with character. A compelling value with exceptional upside, this property invites buyers, investors, or renovators to unlock its full potential. Inside, you'll find timeless details including wide plank flooring and a fireplaced living room, creating a warm and inviting focal point. An enclosed front porch provides a peaceful retreat, perfect for enjoying the natural surroundings, from the gentle sounds of a nearby stream to quiet evenings under the stars. The flexible dining room can easily serve as a home office, den, or creative space. Additional features include a detached two-car garage with a deck and upper-level area, offering excellent storage or the possibility for future expansion. While the home requires significant renovation, the setting, acreage, and historic charm make this a truly special offering. Bring your vision and transform this property into something extraordinary.

34 Hannifin Rd, Winchester

624 Wynne Rd, Winchester
$75,000
24175027 MLS
Exceptional opportunity to build near one of Northwest Connecticut's most desirable lake communities. Just steps from beautiful Highland Lake, this water-view parcel offers the chance to create your dream home in a setting that combines lake lifestyle, natural beauty, and convenient access to some of Litchfield County's most sought-after destinations. Highland Lake is a true Connecticut gem-a picturesque, natural lake in historic Winchester, spanning approximately 444-445 acres, about three miles long, with three distinct bays and depths reaching approximately 63 feet. Known for boating, fishing, swimming, and year-round enjoyment, Highland Lake has long been treasured for its scenic shoreline, established lake community, and recreational appeal. The lake is also recognized by Connecticut DEEP with a public boat launch and boating regulations, further supporting its active recreational use. The location is equally compelling: enjoy the peaceful feel of a classic Litchfield County lake setting while remaining convenient to Salisbury, Lakeville, Norfolk, Torrington, and downtown Winsted. Hartford is roughly 40 minutes away by car, making this an ideal retreat without sacrificing accessibility.

624 Wynne Rd, Winchester

132 Florence St, Winchester
$60,000
24179755 MLS
Rare opportunity to build your dream home on this 1.07-acre vacant lot conveniently located close to downtown shopping, dining, and everyday amenities. Situated in an established neighborhood, this property offers season-long westerly views and spectacular sunset vistas, creating the perfect backdrop for your future home. Public water and public sewer are available in the street (buyer to verify availability and connection requirements). Buyers are encouraged to discuss their building plans with the Town's Land Use and Development Department to determine potential uses and requirements. Whether you're planning a year-round residence or a custom-designed retreat, this property offers an excellent combination of location, views, and potential.

132 Florence St, Winchester

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