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Winchester, CT Homes for Rent

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  • /17

    $1,400 Per Month

    • 2 Beds
    • 1.5 Baths
    • 1,100 Sq Ft
    • House for Rent

    104 Elm St, Winsted, CT 06098

    Spacious two-bedroom, 1.5-bath apartment conveniently located close to downtown. The kitchen features a convenient pantry for additional storage and offers direct access to a covered rear porch-perfect for enjoying your morning coffee or relaxing outdoors. The apartment also offers plenty of storage, including dedicated basement storage space and a walk-up attic with additional room for your

    Agent Photo

    Jeffrey Liskin

    Northwest CT Realty

    104 Elm St, Winsted, CT 06098
  • /34

    Starting at $1,500 Plus Fees

    • 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

    Mill at Still River

    101 Whiting St, Winsted, CT 06098
  • /4

    $1,095 Per Month

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

    139 N Main St Unit LL, Winsted, CT 06098

    Cozy one-bedroom apartment with a practical layout. Features a living room, kitchen, bedroom, and in-unit washer and dryer. Pets considered. First month and 2 months security, if applicable. Credit and background check through Rentspree.

    Agent Photo

    Amanda Balaski

    Northwest CT Realty

    139 N Main St Unit LL, Winsted, CT 06098
  • /20

    Starting at $1,150 Plus Fees

    • 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

    Gilbert Clock Apartments

    13 Wallens St, Winsted, CT 06098
  • /4

    $1,495 Per Month

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

    99-101 Elm St, Winsted, CT 06098

    Two bedroom, first floor apartment with laundry hook-up in the unit. Washer/dryer can be added for an additional $100 per month. Close to downtown. Off street parking, pets considered. Gas and electric heat. First month, two months security required. Background and credit check done by listing office.

    Agent Photo

    Amanda Balaski

    Northwest CT Realty

    99-101 Elm St, Winsted, CT 06098
  • /5

    $1,800 Plus Fees

    • 3 Beds
    • 1 Bath
    • 1,260 Sq Ft
    • House for Rent

    335 Taylor Brook Rd, Winchester, CT 06098

    Welcome to your new home in Winsted, Winchester, CT! This charming property offers an inviting atmosphere perfect for comfortable living. Its convenient location places you near several great restaurants, making dining out a breeze. Plus, the Community Health & Wellness Center is just a short 14-minute drive away, ensuring easy access to health services.This property features essential

    335 Taylor Brook Rd, Winchester, CT 06098
  • /20

    $2,800 Plus Fees

    • 3 Beds
    • 1.5 Baths
    • 1,510 Sq Ft
    • Condo for Rent

    506 Main St, New Hartford, CT 06057

    Historic charm meets modern convenience in this updated 3-bedroom, 1.5 bath duplex located in the heart of New Hartford, CT. Built circa 1900, this spacious 1,510 sq. ft. home offers preserved character with thoughtful updates throughout.Available for immediate occupancy, the home features a spacious kitchen with new roof, dishwasher, refrigerator, gas range, washer, and gas dryer.

    506 Main St, New Hartford, CT 06057
  • /10

    $950

    Total Monthly Price

    • 4 Beds
    • 1 Bath
    • 1,254 Sq Ft
    • House for Rent

    14 Curtice St, Winsted, CT 06098

    4-bedroom house with rooms available for rent. Each room is $950 per month. Spacious shared living areas and a full kitchen. A comfortable and peaceful place to call home.

    14 Curtice St, Winsted, CT 06098
  • /9

    $1,500 Per Month

    • 2 Beds
    • 2 Baths
    • 950 Sq Ft
    • Property for Rent

    936 Main St Unit 14, 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 worked on now with 3 new homes to be put in front. Beautiful free standing ranch style homes, 2 bedroom, 2 baths with attached closed porch available. There are 2 houses available at this time for the same price. The other is larger with 2 bedrooms and

    Michael Block Building Blocks LLC

    936 Main St Unit 14, Winchester, CT 06098
  • /6

    $1,525

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 1,045 Sq Ft
    • Condo for Rent

    I 9 Nanni Dr Unit L-09, Winchester, CT 06098

    Nestled in the Hills of Litchfield County, our Large Town Homes Offer:• Updated eat in kitchen with dishwasher and modern flooring. • Spacious bedrooms with new six panel doors and sliders.• Remodeled Bathroom.• Private Entrances with Slider to backyard • Over 1000 square feet of living space with heat and hot water included.Please come see why at Litchfield

    I 9 Nanni Dr Unit L-09, Winchester, CT 06098
  • /12

    $1,195 Per Month

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

    267 Rockwell St Unit 1st fl, Winsted, CT 06098

    Ground level 1 bedroom 1 bath unit. Walking distance to Highland Lake. Laundry hookups in the unit. No Pets No Smoking, Credit, background, eviction checks, 1st month rent, 2 months security deposit.

    Diane Carroll The Washington Agency

    267 Rockwell St Unit 1st fl, Winsted, CT 06098
  • /6

    $1,525

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 1,045 Sq Ft
    • Condo for Rent

    I 9 Nanni Dr Unit L-09, Winchester, CT 06098

    Nestled in the Hills of Litchfield County, our Large Town Homes Offer:• Updated eat in kitchen with dishwasher and modern flooring. • Spacious bedrooms with new six panel doors and sliders.• Remodeled Bathroom.• Private Entrances with Slider to backyard • Over 1000 square feet of living space with heat and hot water included.Please come see why at Litchfield

    I 9 Nanni Dr Unit L-09, Winchester, CT 06098
  • /37

    $5,000 Per Month

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

    880 W Wakefield Blvd, Winsted, CT 06098

    Available Seasonal 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.

    Matt Crossen Coldwell Banker Realty

    880 W Wakefield Blvd, Winsted, CT 06098
  • /8

    $1,500 Per Month

    • 2 Beds
    • 1.5 Baths
    • 950 Sq Ft
    • Property for Rent

    936 Main St Unit 12, Winchester, CT 06098

    Recently purchased and re-built manufactured home community in Winsted in final stages of being completed. Beautiful free standing ranch style homes, 2 bedroom with 1 bath and 2 baths available as well as an attached entrance enclosed porch. This is a small manufactured home community. Come see these homes. You can't rent a single-family house as nice as these for the price. As each house has

    Michael Block Building Blocks LLC

    936 Main St Unit 12, Winchester, CT 06098
  • /22

    $2,100 Per Month

    • 3 Beds
    • 1 Bath
    • 1,042 Sq Ft
    • House for Rent

    34 Rock St, Winsted, CT 06098

    Lovely Colonial home for rent recently remodeled, with large sun filled open concept living room, and separate dining area off of the beautiful fully equipped kitchen. Spacious carpeted mud room with ample room for coats, boots, and backpacks. Wood floors throughout home. Three bedrooms on second floor with nice views. Energy efficient gas heat. Large deck in rear overlooking back yard for

    Terry Cubeddu Ameristar Royal Realty LLC

    34 Rock St, Winsted, CT 06098
  • /28

    $1,950 Per Month

    • 2 Beds
    • 2 Baths
    • 1,289 Sq Ft
    • Townhouse for Rent

    59 Cook St Unit 7, Winsted, CT 06098

    Rarely available 2-story townhouse condo for rent! Start your mornings with coffee on the rear deck with a lake view in the distance. This condo features 2 spacious bedrooms and 2 full bathrooms, including a primary suite with a full bath and shower stall. Enjoy easy-to-maintain laminate flooring throughout. The property offers a private 1-car garage plus 2 additional off-street parking spaces in

    Debra Jablonski Berkshire Hathaway NE Prop.

    59 Cook St Unit 7, 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

How much does it cost to rent a home in Winchester, CT?
The median rent for a home in Winchester, CT is $1,525 per month, though prices vary by neighborhood, size, and property type. As of August 2026, condos tend to be the most affordable option while single-family homes and townhouses are currently more expensive.
How much do you need to make to afford rent in Winchester, CT?
To comfortably afford the median rent in Winchester, CT, a household needs to earn roughly $61,000 per year. This is based on the common guideline that households should spend no more than 30% of gross income on housing. Most landlords require monthly household income of at least 3x the monthly rent, and with a median rent of $1,525 per month in Winchester, CT, renters typically need to show $4,575 per month in gross income to qualify. Actual affordability will vary depending on household debts, other living expenses, and overall budget.
Is it more affordable to rent or buy in Winchester, CT?
In Winchester, CT, the price-to-rent ratio is 18.9, which generally favors renting. This ratio divides the median home price by the annual median rent: below 15 typically favors buying, 15 to 20 is balanced, and above 20 typically favors renting. Your finances, how long you plan to stay, and costs like mortgage rates, taxes, and maintenance all factor into the decision.
What neighborhoods in Winchester, CT are best for renting a home?
The best neighborhood for renting in Winchester, CT depends on your priorities: commute, walkability, budget, and lifestyle all play a role. Popular areas for renting a home include North Bristol, Downtown Bristol, Federal Hill and Forestville, each with its own character and price range.

Rental Home Trends

Number of Homes for Rent
16
Median Rent
$1,525
Median Single Family Home Rent
$1,500
Median Townhouse Rent
$1,648
Median Condo Rent
$1,365
How to Rent a Home