15

Winchester, CT Homes for Sale with Garage

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  • /34

    $599,900

    • 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

    Agent Photo

    David Sartirana

    Northwest CT Realty

    (860) 773-4065

    441 Platt Hill Rd, Winsted, CT 06098
  • /37

    $499,999

    • 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

    Agent Photo

    David Sartirana

    Northwest CT Realty

    (860) 390-5071

    55 Walnut St, Winsted, CT 06098
  • /36

    $499,000

    • 3 Beds
    • 2 Baths
    • 2,167 Sq Ft

    197 Spencer Hill Rd, Winsted, CT 06098

    Discover the charm of this spacious contemporary Cape, set on a peaceful one-acre lot in a desirable rural neighborhood. Offering over 3,000 square feet of living space, this well-maintained home provides a flexible layout ideal for today's lifestyle. The main level features a formal living room, dining room, updated kitchen, den, sunroom with fireplace and hot tub, full bath, and convenient

    Agent Photo

    David Sartirana

    Northwest CT Realty

    (860) 419-0914

    197 Spencer Hill Rd, Winsted, CT 06098
  • /27

    $394,900

    • 2 Beds
    • 1.5 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

    Agent Photo

    Tammy Powling

    Coldwell Banker Realty

    (860) 743-1453

    212 Spencer Hill Rd, Winsted, CT 06098
  • /38

    $1,270,000

    • 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

    $749,999

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

    151 Losaw Rd, Winsted, CT 06098

    This property is your personal sanctuary, complete with private trails for hiking your own land. 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. 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
  • /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
  • /35

    $339,900 Open Sun 12PM - 2PM

    • 4 Beds
    • 2 Baths
    • 1,999 Sq Ft

    148 Danbury Quarter Rd, Winchester, CT 06098

    Welcome to this Wonderful Historic Colonial Farmhouse, built in 1800. This home has been lovingly remodeled with many of the original features still intact. This home offers a large kitchen with granite 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

    Susan MCGHEE The Washington Agency

    148 Danbury Quarter Rd, Winchester, CT 06098
  • /40

    $549,000

    • 3 Beds
    • 2 Baths
    • 1,745 Sq Ft

    106A Pinney St, Colebrook, CT 06021

    Nature Lover's Retreat on 26 Acres!!! Tucked away on 26.12 private acres, this contemporary Cape offers peace, privacy, and a deep connection to nature. A long, winding driveway leads to this stunning home featuring soaring ceilings and dramatic two-story windows that fill the living room with natural light. The open layout includes a warm wood stove, first-floor laundry, and two comfortable

    Kelly Sullivan Sullivan Real Estate Inc

    106A Pinney St, Colebrook, CT 06021
  • /37

    $500,000

    • 4 Beds
    • 2.5 Baths
    • 3,416 Sq Ft

    440 Platt Hill Rd, Winsted, CT 06098

    Distinctive Country Estate with Two Homes on 9.6 Rolling Acres Set amid 9.6 picturesque country acres, this unique property offers two homes and endless potential. The stone and stucco main residence features eight spacious rooms, including four bedrooms and four fireplaces, blending classic character with old-world charm. Rolling open land and mature trees surround the home, providing an ideal

    David D'Amore Northwest CT Realty

    440 Platt Hill Rd, Winsted, CT 06098
  • /22

    $499,000

    • 3 Beds
    • 2 Baths
    • 2,186 Sq Ft

    11 Old Creamery Rd, Colebrook, CT 06021

    FULLY RENOVATED! In addition this home is fully insulated, energy-efficient, and enhanced with solar panels for low utility costs. The open floor plan and cozy fireplace create the perfect space for gatherings, while multiple decks, an above-ground pool, and serene natural surroundings provide a tranquil retreat-ideal for year-round living or a weekend getaway. Located perfectly on a beautiful

    Dani Dorman Real Broker CT, LLC

    11 Old Creamery 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
  • /34

    $749,900

    • 7 Beds
    • 3 Baths
    • 3,486 Sq Ft

    39 S Main St, Winsted, CT 06098

    THREE PROPERTIES ONE PRICE!!! Includes single family, multi family & additional lot totaling 4.36 acres. 1. 3500 sq ft 2 family home featuring 1800's architecture including massive period correct windows, wrap around porch, beautiful stone foundation, and detached 2 car garage. 5 bed, 2 1/2 bath main house with 2 bed, 1 bath attic apartment, freshly updated. Brand new whole house natural gas

    RYAN HORVAY Smith & DeGroat Real Estate

    39 S Main St, Winsted, CT 06098
  • /36

    $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
  • /40

    $2,199,000

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

    431 W Wakefield Blvd, Winsted, CT 06098

    LOCAL NEWS JUST ANNOUNCED THAT WINSTED WAS 1 OF THE MOST DESIRABLE TOWNS TO LIVE WITH EMPHASIS ON BEAUTIFUL HIGHLAND LAKE. 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

    Lisa Ogren Berkshire Hathaway NE Prop.

    431 W Wakefield Blvd, Winsted, CT 06098

Home Trends in Winchester, CT

Housing Trends

Median Sale Price
$385,000
Median Single Family Sale Price
$362,450
Average Price Per Sq Ft
$259
Number of Homes for Sale
1
Last 12 months Home Sales
3
Months of Supply
4.00
Median List Price
$344,900
Median Change From 1st List Price
-4%
Median Home Sale Price YoY Change
5%
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