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Winchester, CT Homes for Rent

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  • /4

    $165 total monthly price

    • 200 Sq Ft
    • House for Rent

    113 Elm St Unit Left, Winsted, CT 06098

    One of two available storage units. Each unit is 200 square feet and can be used as extra storage or as a garage.

    Agent Photo

    Jeffrey Liskin

    Northwest CT Realty

    (860) 735-3947

    113 Elm St Unit Left, Winsted, CT 06098
  • /2

    $165 total monthly price

    • 200 Sq Ft
    • House for Rent

    113 Elm St Unit Right, Winsted, CT 06098

    One of two available storage units. Each unit is 200 square feet and can be used as extra storage or as a garage.

    Agent Photo

    Jeffrey Liskin

    Northwest CT Realty

    (860) 809-5763

    113 Elm St Unit Right, Winsted, CT 06098
  • /8

    $1,695 total monthly price

    • 3 Beds
    • 1 Bath
    • 1,080 Sq Ft
    • Townhouse for Rent

    131-133 Willow St, Winchester, CT 06098

    Bright and sunny 3-bedroom duplex, ideally located close to town. This spacious home features a large eat-in kitchen, a separate dining room, and a cozy living room. Enjoy the convenience of gas heat, with washer/dryer hook-up available in the basement, or can be provided for an extra $75 per month. Minimum credit score of 700. Pets considered, and a background and credit check are required.

    Agent Photo

    Amanda Balaski

    Northwest CT Realty

    (860) 981-0563

    131-133 Willow St, Winchester, CT 06098
  • /2

    $1,500 total monthly price

    • 2 Beds
    • 1 Bath
    • 800 Sq Ft
    • House for Rent

    244 Walnut St, Winsted, CT 06098

    Bright first-floor 2-bedroom, 1-bath apartment available at 244 Walnut St in Winsted, CT. This well-maintained unit features all new windows that provide plenty of natural light and improved energy efficiency, along with natural gas heat for affordable utilities. Conveniently located in a quiet residential area close to downtown Winsted, shopping, and local amenities. Comfortable first-floor

    Agent Photo

    William Kallberg

    Berkshire Hathaway NE Prop.

    (860) 730-1457

    244 Walnut St, Winsted, CT 06098
  • /8

    $1,495 total monthly price

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft
    • House for Rent

    112 Rockwell St Unit 1, Winsted, CT 06098

    Bright and sunny, first floor, 2 bedroom apartment. Washer/dryer in the unit. Large, private porch. Pets considered. Off street parking. Minimum credit score required. Credit and background check done by listing office. required. Two months security, if applicable.

    Agent Photo

    Amanda Balaski

    Northwest CT Realty

    (860) 609-3853

    112 Rockwell St Unit 1, Winsted, CT 06098
  • /10

    $1,450 total monthly price

    • 2 Beds
    • 1 Bath
    • 800 Sq Ft
    • House for Rent

    79 Chestnut St, Winsted, CT 06098

    Located at 79 Chestnut Street, this third-floor apartment offers 2 bedrooms and 1 full bathroom with approximately 750 sq ft of living space in a multi-family building built in 1915. The unit features a comfortable layout with a living room, kitchen, and two bedrooms, along with thermopane windows and natural gas baseboard heating. A washer/dryer hookup is conveniently located inside the unit,

    Agent Photo

    William Kallberg

    Berkshire Hathaway NE Prop.

    (860) 981-0377

    79 Chestnut St, Winsted, CT 06098
  • /7

    $1,150 total monthly price

    • 1 Bed
    • 1 Bath
    • 1,400 Sq Ft
    • House for Rent

    112 Rockwell St Unit LL, Winsted, CT 06098

    Private 1bedroom apartment with its own porch and yard, plus in-unit washer/dryer. Pets considered. Conveniently located near the center of town and Highland Lake. First month's rent plus two months' security deposit required. Credit and background check performed by the listing office.

    Agent Photo

    Amanda Balaski

    Northwest CT Realty

    (860) 321-4592

    112 Rockwell St Unit LL, Winsted, CT 06098
  • /12

    $2,400 total monthly price

    • 3 Beds
    • 1 Bath
    • 1,860 Sq Ft
    • House for Rent

    101 Norfolk Rd, Winsted, CT 06098

    Raised Ranch rental close to town on 1.33 wooded acres. The lower level features two large rooms with new vinyl plank flooring, fresh paint, and a spacious storage/utility room with laundry. The main floor includes a living room and an updated kitchen with quartz countertops and stainless steel appliances. Sliders lead to a large deck overlooking the private wooded yard. There is a large primary

    Agent Photo

    Amanda Balaski

    Northwest CT Realty

    (860) 845-0664

    101 Norfolk Rd, Winsted, CT 06098
  • /34

    $1,500 - $1,800 per month plus fees

    Mill at Still River

    1 - 2 Beds

    101 Whiting St, Winsted, CT 06098

    By far the best place to live in Winsted, Connecticut. Turn of the century construction, every unit overlooks the beautiful Still River, our 700-1000 square-foot one and two bedroom interiors are bright and charming and feature exposed wood beams, 10-foot ceilings, oversized industrial windows, and exposed brick walls. We deliver nature at your door. Our community amenities include same-floor

    101 Whiting St, Winsted, CT 06098
  • /3

    $800 total monthly price

    • 1 Bath
    • 4,668 Sq Ft
    • House for Rent

    440 Main St Unit C, Winchester, CT 06098

    Two room Studio apartment set in town. Convenient to stores, restaurants and medical facility.

    Linda Ganem Borla & Associates Real Estate

    440 Main St Unit C, Winchester, CT 06098
  • /20

    $1,150 - $1,550 per month plus fees

    Gilbert Clock Apartments

    Studio - 2 Beds

    13 Wallens St, Winsted, CT 06098

    At Gilbert Clock Apartments , our designer-inspired amenities set us apart from the competition. We pride ourselves on providing top-quality apartments outfitted with the everyday amenities you expect as well as luxury amenities to delight your senses and enhance your modern life. Indulge your culinary instincts in your state-of-the-art kitchen, furnished with Beautiful and energy-efficient

    13 Wallens St, Winsted, CT 06098
  • /3

    $1,495 total monthly price

    • 2 Beds
    • 1 Bath
    • 1,100 Sq Ft
    • House for Rent

    50 Benton St, Winsted, CT 06098

    5 room, 1st floor apartment in well established neighborhood. Ranch style. Large eat-in kitchen, 2 bedrooms, den/office. 1 full bath. Ample closets, additional light storage is available in basement. Appliances include, gas range, refrigerator, washer & dryer (in basement). off street parking. Private rear yard.

    JULIE FEDOROVICH Dave Jones Realty, LLC

    50 Benton St, Winsted, CT 06098
  • /37

    $2,450 total monthly price

    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft
    • House for Rent

    91 Williams Ave, Winsted, CT 06098

    Welcome to this beautifully remodeled and spacious 3-bedroom, 2 full bathroom home in the heart of Winchester. Featuring hardwood floors throughout both the first and second levels, this home offers a warm and inviting layout with an eat-in kitchen that has a center island perfect for everyday living. Enjoy the convenience of a separate laundry room-washer and dryer included, high-efficiency gas

    Suzie Larson Turning Point Realty, LLC

    91 Williams Ave, Winsted, CT 06098
  • /12

    $2,500 total monthly price

    • 2 Beds
    • 1 Bath
    • 1,100 Sq Ft
    • House for Rent

    188 E Lake St, Winsted, CT 06098

    Welcome to our beautiful lakeside apartment, perfect for professionals seeking a home away from home for long or short term rentals. Situated on the picturesque shores of Highland Lake, this fully renovated and furnished apartment offers stunning views and serenity that will make you never want to leave. The modern design and elegant decor create a welcoming and comfortable environment for our

    Annie Simard LPT Realty

    188 E Lake St, Winsted, CT 06098
  • /10

    $1,500 total monthly price

    • 2 Beds
    • 1 Bath
    • 1,199 Sq Ft
    • House for Rent

    22 Upson Ave, Winsted, CT 06098

    Beautiful First-Floor Apartment with Classic Charm and Modern Updates! This spacious first-floor apartment features gleaming hardwood floors, fresh paint, and an updated kitchen. Enjoy the high ceilings and beautiful woodwork that add character and warmth throughout. Conveniently located close to downtown, offering easy access to shopping, dining, and commuting routes.

    Kelly Sullivan Sullivan Real Estate Inc

    22 Upson Ave, Winsted, CT 06098
  • /37

    $4,000 total monthly price

    • 3 Beds
    • 2 Baths
    • 1,356 Sq Ft
    • House for Rent

    880 W Wakefield Blvd, Winsted, CT 06098

    Discover lakeside living at its finest with this fully renovated, fully furnished 3 bedroom, sleeps 10, 2 full-baths, family estate set on a half acre of professionally landscaped grounds overlooking picturesque Highland Lake. Located just 0.6 miles from Main Street Winsted and Red Barn Brewing, this property combines serene lakefront living with convenient access to local amenities. Enjoy use of

    Matt Crossen Coldwell Banker Realty

    880 W Wakefield Blvd, Winsted, CT 06098

Why Live in Winchester

Winchester, located in the Litchfield Hills of Connecticut, is known for its rural charm and scenic mountain views. This town, often referred to as the Gateway to the Berkshire Mountains, offers a variety of outdoor recreational activities. Highland Lake, a popular attraction, features two public beaches, a boat launch, and a marina with boat rentals and seasonal slips. Winchester Lake and Park Pond provide quieter spots for boating and freshwater fishing. Platt Hill State Park offers unmarked nature trails for hikers and birdwatchers, while nearby Burr Pond, Sunnybrook, and Stillwater Pond State Parks are within 5 miles. The Sue Grossmann Still River Greenway provides a paved path for walking, running, and biking. Green Woods Country Club boasts one of the only three 10-hole golf courses in the United States. Winsted, the downtown area of Winchester, has a walkable Main Street with shops, eateries, and creative spaces like Whiting Mills and the American Mural Project. The Gilbert School, a private secondary school functioning as the public middle and high school, is highly rated and offers various sports programs. Housing options in Winchester range from historic New England-style farmhouses and saltbox homes to Cape Cod and raised ranch-style homes in Winsted, with lakefront properties being more expensive. Winchester is car-dependent, with limited public transportation, but U.S. Route 44 and state Route 8 provide access to Torrington, Hartford, and Bradley International Airport, which is 29 miles away.

Frequently Asked Questions

What are the most popular neighborhoods in Winchester, CT for renters?
The most popular neighborhoods in Winchester, CT for renters are North Bristol, Downtown Bristol and Federal Hill.
What are the most popular zip codes in Winchester, CT for renters?
The most popular zip codes in Winchester, CT for renters include 06098, 06790, 06057, 06058 and 06756.
How to Rent a Home