30

Winchester, CT Houses for Sale

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  • /30

    $394,900

    • 2 Beds
    • 1 Bath
    • 512 Sq Ft

    548 E Wakefield Blvd, Winsted, CT 06098

    Start your lakeside legacy at this rare waterfront cottage on Highland Lake. With stunning westerly views and a private dock, this is the perfect New England retreat for daily sunsets over the water. This intimate 512-square-foot home offers two bedrooms, a sunroom, Modern Eat-in Kitchen and a versatile loft space. with a newer roof, plumbing, electrical, and blown-in insulation, providing a

    Agent Photo

    Amy Rio

    Executive Real Estate Inc.

    (860) 777-1120

    548 E Wakefield Blvd, Winsted, CT 06098
  • /38

    $1,295,000

    • 3 Beds
    • 3 Baths
    • 2,420 Sq Ft

    722 Lake Dr, Winsted, CT 06098

    Welcome to lake living at its finest! Built in 2014 and first time on the market. Impeccably maintained, this stunning three bedroom, 3 bath home on Highland Lake, Winchester offers the perfect blend of comfort, style, and breathtaking VIEWS! From the moment you enter you will be captivated by the open-concept design, high-end finishes and panoramic lake views from both inside and out. Enjoy

    Joanne Donne The Washington Agency

    722 Lake Dr, Winsted, CT 06098
  • /40

    $799,000

    • 5 Beds
    • 2.5 Baths
    • 2,950 Sq Ft

    151 Losaw Rd, Winsted, CT 06098

    Feel worlds away while being less than 2 miles to town amenities in this like-new retreat nestled on an expansive 11.59-acre lot. This property is your personal sanctuary, complete with private trails for hiking your own land. The eat-in-kitchen is well-equipped with ample cooking space, seamlessly connected to the formal dining room and open to living space, and leads out to the large deck with

    Breanna Goebel Compass Connecticut, LLC

    151 Losaw Rd, Winsted, CT 06098
  • /37

    $495,000

    • 4 Beds
    • 1.5 Baths
    • 1,940 Sq Ft

    159 Sandy Brook Rd, Colebrook, CT 06021

    Introducing Sandy Brook Cottage. Perched gently near the banks of the meandering Sandy Brook, this c.1800 home exudes quiet charm and understated elegance. Set on over 3 picturesque acres in the hidden gem of Colebrook. It is a true country escape. One that offers privacy, character, and an effortless connection to nature. Winding stone walls trace the contours of the rolling landscape, creating

    Lenore Mallett William Pitt Sotheby's Int'l

    159 Sandy Brook Rd, Colebrook, CT 06021
  • /34

    $625,000

    • 5 Beds
    • 3 Baths
    • 3,404 Sq Ft

    441 Platt Hill Rd, Winsted, CT 06098

    Welcome to 441 Platt Hill Road - a home that offers warmth, charm, and plenty of space to make memories. This inviting residence features an open and airy layout filled with natural light thanks to large windows and multiple skylights. Solid hardwood floors and tile run throughout the main level, creating a timeless foundation for your personal touch. The spacious eat-in kitchen, while vintage in

    David Sartirana Northwest CT Realty

    441 Platt Hill Rd, Winsted, CT 06098
  • /27

    $449,900

    • 4 Beds
    • 1.5 Baths
    • 2,239 Sq Ft

    51 Pratt St, Winsted, CT 06098

    This stunning Renovated home is perfectly situated in the beautiful town of Winsted could be yours! Just a leisurely walk from the beautiful Highland Lake. Offering more than 2,200 square feet of thoughtfully designed living space, this home blends timeless charm with modern updates. The bright and spacious kitchen opens effortlessly into a welcoming dining area and a cozy yet expansive living

    Arlene Gonzalez The Gonzalez Property Group

    51 Pratt St, Winsted, CT 06098
  • /39

    $779,900

    • 3 Beds
    • 3.5 Baths
    • 4,953 Sq Ft

    111 South Rd, Winsted, CT 06098

    Perched up higher than the rest with sweeping views up a private driveway in beautiful Winchester Center you'll find this custom built 4,953 sq ft Colonial nestled in on 3.97 serene & bucolic acres. For the car enthusiasts, you'll see a 3 bay garage that can fit up to at least 7 cars if lifts are installed including a bonus 2 car tandem garage within the 3 bays. Plenty of room for oversized

    Dawn Rousseau Showcase Realty, Inc.

    111 South Rd, Winsted, CT 06098
  • /35

    $475,000

    • 3 Beds
    • 3 Baths
    • 2,747 Sq Ft

    117 South Rd, Winsted, CT 06098

    Nestled in a peaceful rural setting of Winchester Center, this charming home offers a perfect blend of rustic character and modern convenience. The property is located on over 3.3 acres of land and is adjacent to a scenic pond. Inside you will find a three bedroom two bath home with an additional in law apartment with one full bath and one bedroom and its own private entrance. The home also

    Christina Niziolek William Raveis Real Estate

    117 South Rd, Winsted, CT 06098
  • /35

    $849,900

    • 4 Beds
    • 2 Baths
    • 1,781 Sq Ft

    119 W Wakefield Blvd, Winsted, CT 06098

    Have you been dreaming of breathtaking lake views and a property that is truly special, unique, and turn-key? This exceptional home includes 50 feet of waterfront access with a boat dock and lift, making it a dream for lake enthusiasts! Nestled across from the tranquil First Bay, this beautifully renovated two-family home can be enjoyed as a single-family retreat or an income-generating

    Mela Veltri Case KW Legacy Partners

    119 W Wakefield Blvd, Winsted, CT 06098
  • /37

    $515,000

    • 5 Beds
    • 4 Baths
    • 5,016 Sq Ft

    55 Walnut St, Winsted, CT 06098

    Timeless Victorian with Endless Possibilities.Step into a piece of history with this stunning Victorian property, a landmark in the community and home to The Maloney Funeral Home since the early 1900's. Nestled in the TCR Zone, this versatile building offers a wealth of potential. The TCR Zone allows for accessory residential uses, community centers, family day care homes, single-family

    David Sartirana Northwest CT Realty

    55 Walnut St, Winsted, CT 06098
  • /39

    $299,999

    • 3 Beds
    • 2.5 Baths
    • 1,608 Sq Ft

    36 Whiting St, Winsted, CT 06098

    Newly updated 3 bedroom 2.5 bath colonial with large front porch overlooking the Mad River. Close to downtown and town center green. This home has an updated kitchen with new quartz counters, new furnace and hot water heater along with beautifully refinished hard wood floors through out the first floor. New carpet on second floor bedrooms and the primary bedroom has its own full bathroom. The

    Brandon Riley eXp Realty

    36 Whiting St, Winsted, CT 06098
  • /40

    $295,000

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft

    128 Danbury Quarter Rd, Winsted, CT 06098

    First-time homebuyers and downsizers take notice!. Some improvements have been done in this cozy Ranch boasting a metal roof and well-maintained mechanics. What an incredible opportunity to pick your colors and let the cosmetic upgrades take shape. A 1-car detached garage and space for a garden or outbuilding are possible on this 2.5-acre country parcel. An As-Is sale is preferred.

    Kim Trumbull William Raveis Real Estate

    128 Danbury Quarter Rd, Winsted, CT 06098
  • /38

    $375,000

    • 3 Beds
    • 2.5 Baths
    • 1,584 Sq Ft

    111 Old Rd N, Winchester, CT 06098

    Two parcels for the price of one! Discover this beautifully maintained split-level ranch at 111 Old North Road in Winchester, offered together with the adjoining already-subdivided 2.5-acre buildable lot at 113 Old North Road. Enjoy the home as-is or explore the endless possibilities-build an in-law house, sell the lot, or develop it as an investment. Inside, the home features a unique layout

    Christopher Clarke Coldwell Banker Realty

    111 Old Rd N, Winchester, CT 06098
  • /13

    $199,900

    • 3 Beds
    • 1 Bath
    • 1,248 Sq Ft

    14 Curtice St, Winsted, CT 06098

    Attention investors and buyers looking to build equity! Welcome to 14 Curtice Street, a home has incredible value and potential in the heart of Winsted. This 3-bedroom, 1-bath home features approximately 1,248 square feet of living space and is ideal for sweat-equity seekers or rehab-minded buyers. Exterior updates have already been completed, including a newer roof, siding, and windows, giving

    Michael Johnson Lock and Key Realty, Inc

    14 Curtice St, Winsted, CT 06098
  • /33

    $380,000

    • 3 Beds
    • 2 Baths
    • 2,024 Sq Ft

    166 Torringford St, Winsted, CT 06098

    Nothing to do but move right in to this meticulous colonial farmhouse nestled in the Litchfield Hills. This unique home combines a tasteful modern style mixed with rustic charm. Inside the fully renovated home offers a sprawling kitchen with ample counter and cabinet space, a breakfast bar with elegant quartz countertops and newer stainless steel appliances. The space is open to the dining area

    Lana Van Valkenburgh Vision Real Estate

    166 Torringford St, Winsted, CT 06098
  • /13

    $199,900

    • 3 Beds
    • 1.5 Baths
    • 1,340 Sq Ft

    14 Pratt St, Winsted, CT 06098

    Don't let the outside fool you! Perfect alternative to condominium living! No HOA and plenty of off street parking at this in-town location. Nice size living room; large kitchen/dining combination with access to the deck and the 1/2 bath laundry room make up the first floor of this cute home. Upstairs you will find 2 modest size bedrooms along with the large primary and the full bath which has a

    Amy Sartirana Northwest CT Realty

    14 Pratt St, Winsted, CT 06098
  • /7

    $265,000

    • 3 Beds
    • 1 Bath
    • 1,488 Sq Ft

    312 Colebrook River Rd, Colebrook, CT 06021

    Charming Colonial on a 2-acre lot. Inside, you'll find an updated kitchen featuring granite countertops and newer appliances. The large, sunny family room on the first floor is filled with natural light, creating a warm and inviting atmosphere. A combined living and dining room with a cozy wood stove adds charm and functionality to the main level. Recent upgrades to the home include a new roof in

    Amanda Balaski Northwest CT Realty

    312 Colebrook River Rd, Colebrook, CT 06021
  • /40

    $2,200,000

    • 4 Beds
    • 3.5 Baths
    • 4,327 Sq Ft

    381 Smith Hill Rd, Colebrook, CT 06021

    Welcome to Stones Throw Farm. A rare and magical estate tucked on over 23 rolling, pastoral acres in the heart of Colebrook, a true New England country retreat where timeless beauty and refined simplicity come together in perfect harmony. Set along a quiet country road, this idyllic sanctuary offers an extraordinary lifestyle steeped in elegance, comfort, and the gentle rhythms of nature. At the

    Elvia Gignoux William Pitt Sotheby's Int'l

    381 Smith Hill Rd, Colebrook, CT 06021
  • /40

    $1,149,000

    • 3 Beds
    • 3 Baths
    • 2,097 Sq Ft

    674 E Wakefield Blvd, Winsted, CT 06098

    Experience premier waterfront living on Highland Lake in this beautifully maintained 3-bedroom, 3-bath home offering stunning panoramic lake views and direct water access. Situated in the desirable 3rd Bay, this property boasts a private dock-perfect for boating, swimming, and enjoying all the lake lifestyle has to offer. Inside, you'll find an open and inviting layout with a spacious living

    Patrick Smith Smith & DeGroat Real Estate

    674 E Wakefield Blvd, Winsted, CT 06098
  • /20

    $255,000 Open Sun 11AM - 12PM

    • 3 Beds
    • 1 Bath
    • 1,334 Sq Ft

    22 Curtice St, Winsted, CT 06098

    Step into timeless elegance with this beautifully updated colonial-style home, where classic charm meets modern convenience. Gleaming hardwood floors flow seamlessly throughout the main living areas, creating a warm and inviting atmosphere. The fully renovated kitchen is a chef's dream, featuring premium finishes, sleek countertops, and top-of-the-line appliances. Upstairs, you'll find spacious

    Terence Dominick Complete Real Estate

    22 Curtice St, Winsted, CT 06098
  • /10

    $225,000

    • 2 Beds
    • 1 Bath
    • 768 Sq Ft

    130 Stanton Ave, Winsted, CT 06098

    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

    David D'Amore Northwest CT Realty

    130 Stanton Ave, Winsted, CT 06098
  • /14

    $214,900

    • 3 Beds
    • 1 Bath
    • 980 Sq Ft

    99 Norfolk Rd, Winsted, CT 06098

    99 Norfolk Rd, Winsted CT - Opportunity Knocks! This cute 3-bedroom Cape sits proudly on 1.3 acres and is ready for its next chapter! With vinyl siding, replacement windows, and a lovely setting perched high up from the road, the bones are here-now it just needs your vision. For those seeking an investment opportunity or ready to roll up their sleeves and bring this gem back to life, this could

    Lisa McCarthy Coldwell Banker Realty

    99 Norfolk Rd, Winsted, CT 06098
  • /27

    $355,000

    • 3 Beds
    • 1.5 Baths
    • 2,160 Sq Ft

    181 Torringford St, Winsted, CT 06098

    Motivated seller! Charming Colonial on Nearly an Acre! Discover the perfect blend of comfort and space in this 3-bedroom, 1.5-bathroom Colonial home. Situated on almost an acre of flat, usable land, the property features a brand new grand circular driveway and a detached two-car garage. The inviting exterior, with its covered front porch, welcomes you into a home ready for its next chapter.

    Michelle Grant Coldwell Banker Premier Real Estate

    181 Torringford St, Winsted, CT 06098
  • /36

    $299,000

    • 3 Beds
    • 1.5 Baths
    • 1,736 Sq Ft

    38 Upland Rd, Winsted, CT 06098

    Estate Owned 3 to 4 Bedroom Colonial in Immaculate Move In Condition! Tucked away on a quiet street but within walking distance of Schools, Medical Facilities and Shopping. Special features include a huge cedar closet, Hardwood floors throughout the entire house, bay windows, 24' x 14' Family Room with Propane Gas Stove and an Oversized Full Bath The Master Bedroom features its own office.

    Holly Blinkoff Cohen Agency

    38 Upland Rd, Winsted, CT 06098
  • /39

    $995,000

    • 4 Beds
    • 2 Baths
    • 3,088 Sq Ft

    469 Platt Hill Rd, Winsted, CT 06098

    HOME-LAND -BARN. A TRUE NEW ENGLAND CLASSIC PROPERTY IN A POST CARD SETTING! For the Discerning Customer, whether You're an ANTIQUARIAN, HORSE & ANIMAL LOVER, or just seeking for a PEACEFUL & TRANQUIL LOCATION, this LITCHFIELD COUNTY HOME could possibly fit your Criteria. Stately 1789 11 Room 3,088 Sq. Ft. Colonial expresses Love, Warmth & Care. From the Solid Beams, Chestnut Wide-Board Floors,

    Marshall Cohen Cohen Agency

    469 Platt Hill Rd, Winsted, CT 06098
  • /26

    $1,200,000

    • 5 Beds
    • 2.5 Baths
    • 3,307 Sq Ft

    77 Deer Hill Rd, Colebrook, CT 06021

    Enchanting Antique Dutch Colonial Estate with Carriage House and Barn. Nestled in a serene and private 51.2-acre haven, this stately home is a harmonious blend of historic charm and modern sophistication. As you traverse the meandering stone walls and explore the mix of sun-kissed meadows and whispering forests, you'll discover a world where time stands still, yet every modern convenience is at

    MICHAEL CONLOGUE William Pitt Sotheby's Int'l

    77 Deer Hill Rd, Colebrook, CT 06021
  • /40

    $2,199,000

    • 9 Beds
    • 5.5 Baths
    • 7,000 Sq Ft

    431 W Wakefield Blvd, Winsted, CT 06098

    This waterfront estate at 431 W. Wakefield Blvd in Winchester, CT, is not just a home but the ultimate Highland Lake lifestyle. Imagine waking up each day to stunning lake views, with endless seasonal activities awaiting just beyond your doorstep. In the summer, dive into boating, jet skiing, swimming, and fishing right from your private dock, or simply unwind along the shoreline. As winter

    Lisa Ogren Berkshire Hathaway NE Prop.

    431 W Wakefield Blvd, Winsted, CT 06098
  • /5

    $355,750 Coming Soon

    • 3 Beds
    • 1.5 Baths
    • 1,833 Sq Ft

    126 Forest Ave, Winsted, CT 06098

    Charming Cape 2 minutes to Highland Lake. Welcome to this one owner, 3 bedroom, two bath Cape Cod home offering over 1,800 sq. ft. of living space on nearly one acre of land. Owned by the original family. This property has been lovingly maintained and thoughtfully update. Step inside to find a fully appliance kitchen, fresh carpeting, and updated windows and gutters. The flexible seven- room

    Joanne Donne The Washington Agency

    126 Forest Ave, Winsted, CT 06098
  • /6

    $399,900 Coming Soon

    • 3 Beds
    • 2 Baths
    • 1,440 Sq Ft

    212 Spencer Hill Rd, Winsted, CT 06098

    Welcome to your peaceful retreat in the heart of Winchester - a quiet, scenic town surrounded by natural beauty. Tucked away on a private lot, this thoughtfully maintained home offers a perfect blend of rustic charm and modern comfort, with every detail designed to enhance your connection to the outdoors. Step inside to discover gleaming original hardwood floors that stretch across the sun-filled

    Tammy Powling Coldwell Banker Realty

    212 Spencer Hill Rd, Winsted, CT 06098
  • /2

    $350,000 Coming Soon

    • 5 Beds
    • 2.5 Baths
    • 2,376 Sq Ft

    157 Elm St, Winsted, CT 06098

    Victorian Charm Meets Modern Potential - 5-Bedroom Home Across from Pearson School Step into timeless elegance with this spacious 5-bedroom, 2.1-bath Victorian-style home located directly across from Pearson School in Winsted. Featuring hardwood floors throughout and a beautifully updated kitchen, this property blends classic character with modern convenience. From its distinctive architectural

    Doreen Gagnon Coldwell Banker Realty

    157 Elm St, Winsted, CT 06098

Why Live in Winchester

First settled in 1732, the rural town of Winchester retains its historic look and feel. This forested expanse at the base of the Berkshire Mountains is speckled with Colonial Revivals and Craftsman-inspired homes that range from cozy cabins to ...

Home Trends in Winchester, CT

Housing Trends

Median Sale Price
$385,000
Median Single Family Sale Price
$380,000
Average Price Per Sq Ft
$252
Number of Homes for Sale
1
Last 12 months Home Sales
3
Months of Supply
4.00
Median List Price
$362,450
Median Change From 1st List Price
-12%
Median Home Sale Price YoY Change
62%
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