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Winchester, CT Homes for Rent

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    $1,500 - $1,800 per month

    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
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    $850 per month

    • 1 Bed
    • 1 Bath
    • 625 Sq Ft
    • Apartment for Rent

    14 Gay St, Winsted, CT 06098

    First floor one bedroom apartment with off street parking for one car. First month's rent and two month's security if applicable. One year lease required. Walk to shopping, library and restaurants. Great location!

    David Sartirana Northwest CT Realty

    14 Gay St, Winsted, CT 06098
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    $1,450 per month

    Litchfield Heights

    2 Beds

    15 Mountain View Terrace, Winsted, CT 06098

    Litchfield Heights Apartments is nestled quietly in the greenery of the Berkshires. We are situated close to the border of Massachusetts with easy access from Routes 8 & 44. We offer generously sized 1 bedroom flats, and 2 or 3 bedroom Townhouse. Enjoy the ease of maintenance free living when you make Litchfield Heights Apartments your home. Call Litchfield Heights Apartments today for further

    15 Mountain View Terrace, Winsted, CT 06098
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    $1,595 per month

    • 4 Beds
    • 1 Bath
    • 1,158 Sq Ft
    • House for Rent

    49 Wetmore Ave Unit 2nd Flr, Winsted, CT 06098

    Spacious 4 bedroom, 2nd floor apartment with a large porch. Washer/dryer hook-up in the unit. Off street parking. Pets considered. Credit and background check required.

    Amanda Balaski Northwest CT Realty

    49 Wetmore Ave Unit 2nd Flr, Winsted, CT 06098
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    $1,000 - $1,450 per month

    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
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    $1,350 per month

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

    23 Allen St, Winsted, CT 06098

    Discover your new home in this delightful 2-bedroom, 1-bathroom apartment offering 1,100 square feet of thoughtfully designed living space. Located on a peaceful dead-end road in a quiet neighborhood, this unit combines comfort, convenience, and charm in a prime location close to amenities. Step into an inviting open-concept living and dining area, accentuated by coffered ceilings that add a

    Jeffrey Liskin Northwest CT Realty

    23 Allen St, Winsted, CT 06098
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    $1,650 per month

    • 2 Beds
    • 1 Bath
    • 1,200 Sq Ft
    • House for Rent

    23 Wetmore Ave Unit 2, Winsted, CT 06098

    Available 8-1-25. Immaculate second floor unit, recently renovated, super clean and bright. Quiet second floor, spacious layout. 2 bedroom, hardwood floors and tile throughout. Pet may be considered. Washer and Dryer in unit. All newer appliances, gas range. Off street parking. Private enclosed second floor back porch and private enclosed front porch. Small water and sewer fee per person.

    Suzie Larson Turning Point Realty, LLC

    23 Wetmore Ave Unit 2, Winsted, CT 06098
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    $1,145 per month

    • 1 Bed
    • 1 Bath
    • 800 Sq Ft
    • House for Rent

    174 Main St Unit A, Winsted, CT 06098

    One bedroom apartment on the first floor. Large kitchen and a recently remodeled bath. Washer/dryer can be added in the unit for an additional $75 per month. Pets considered. First month and two months security, if applicable. Credit and background check required.

    Amanda Balaski Northwest CT Realty

    174 Main St Unit A, Winsted, CT 06098
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    $1,500 per month

    • 2 Beds
    • 1 Bath
    • 834 Sq Ft
    • Townhouse for Rent

    141 Boyd St, Winchester, CT 06098

    Stop by and check out this charming duplex style rental close to the highland beach public boat launch and Holland beach . You can buy a beach pass at Townhall for lots of summer fun . This unit features a covered front porch that enters you into a cozy living room with recessed lighting , wood floors and a fireplace mantel . The kitchen has been remodeled with stainless appliances, refrigerator,

    Mary Mary LeBlanc Realty

    141 Boyd St, Winchester, CT 06098
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    $1,400 per month

    • 2 Beds
    • 2 Baths
    • 1,000 Sq Ft
    • Property for Rent

    936 Main St Unit 7, Winchester, CT 06098

    Recently purchased and re-built manufactured home community in Winsted in final stages of being completed. The entrance to the property is being changed and will be much nicer than now. This is the final phase. Beautiful free standing ranch style homes, 2 bedroom with 2 baths available as well as an attached entrance enclosed porch. This is the only house available, all others are rented to good

    Michael Block Building Blocks LLC

    936 Main St Unit 7, Winchester, CT 06098
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    $2,200 per month

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

    188 E Lake St, Winsted, CT 06098

    Welcome to our beautiful lakeside apartment! 2 bedroom/1 Bath. Situated on the picturesque shores of Highland Lake, this fully renovated and furnished apartment offers stunning views and serenity. The apartment features a spacious living area, a fully equipped kitchen, huge primary bedroom with lake views, dedicated office space and in unit laundry. Whether you are looking for a peaceful

    Annie Simard LPT Realty

    188 E Lake St, Winsted, CT 06098
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    $6,500 per month

    • 4 Beds
    • 3 Baths
    • 3,014 Sq Ft
    • House for Rent

    255 Smith Hill Rd, Colebrook, CT 06021

    Escape to the heart of the Litchfield Hills at this inspiring private retreat set on over 31 picturesque acres! Available as a short-term summer rental from June 15 until September 15, this exceptional property borders the Berkshires and sits adjacent to a pristine state forest and river-perfect for fly fishing and outdoor exploration. Surrounded by orchards and rolling countryside, the

    Svetlana Chkolnik William Pitt Sotheby's Int'l

    255 Smith Hill Rd, Colebrook, CT 06021

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 extravagant lake houses. Some homeowners come for summer vacations, while others stay to raise their children and grandchildren. “There’s a large cross-section of people who come here, so each smaller community is like a little world unto itself,” says Tom McGowan, a realtor and historic home specialist at Elyse Harney Real Estate. The vast majority of people who live in Winchester own their homes, and those homes have continued to appreciate in value since 2019. Currently, most houses fall into the $225,000 to $750,000 range. However, a lakefront property with a private dock can sell for $900,000 or more. Architectural styles range from charming Cape Cods, cottages and bungalows to Colonial Revival and ranch-styles with second-story overhangs. Though home ages tend to skew half a century or older, most are outfitted with granite countertops and updated appliances. They are often spread acres apart along country roads and obscured by thick

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, West Granby, Downtown Bristol, Federal Hill and Forestville.
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, 06759, 06019 and 06001.
How to Rent a Home