20

Newest Homes for Rent in Winchester, CT

Section Image Section Image
  • B 2 Nanni Dr Unit H-02, Winchester, CT 06098
    B 2 Nanni Dr Unit H-02, Winchester, CT 06098
    B 2 Nanni Dr Unit H-02, Winchester, CT 06098
    /10

    $1,550

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 1,045 Sq Ft
    • 2 Bedroom Townhouse Heat and Hot Water Included

    B 2 Nanni Dr Unit H-02, Winchester, CT 06098

    Nestled up in the hills of Litchfield our large town homes offer:• Updated eat in kitchens with dishwashers and modern flooring. • Spacious bedrooms with new six panel doors and sliders.• Private Entrances with walk out basements and washer/dryer hookups• Over 1000 square feet of living space with heat and hot water includedPlease come see why at Litchfield

    B 2 Nanni Dr Unit H-02, Winchester, CT 06098
  • 111 Rockwell St Unit A, Winchester, CT 06098
    111 Rockwell St Unit A, Winchester, CT 06098
    111 Rockwell St Unit A, Winchester, CT 06098
    /10

    $1,225 Plus Fees

    • 2 Beds
    • 1 Bath
    • 850 Sq Ft
    • Condo for Rent

    111 Rockwell St Unit A, Winchester, CT 06098

    Charming 2-bedroom, 1-bath unit located in a quiet Winsted neighborhood on a spacious corner lot. This home features a well-appointed kitchen with ample cabinet space, a cozy island, and appliances. The unit includes beautiful hardwood floors throughout the living spaces and large windows that fill the rooms with natural light. Outside, enjoy a private entrance and a shared green space.

    111 Rockwell St Unit A, Winchester, CT 06098
  • 112 Rockwell St Unit 2, Winsted, CT 06098
    112 Rockwell St Unit 2, Winsted, CT 06098
    /2

    $1,595 Per Month

    • 4 Beds
    • 1.5 Baths
    • 900 Sq Ft
    • House for Rent

    112 Rockwell St Unit 2, Winsted, CT 06098

    Large four bedroom apartment with a bath and a half. Large kitchen, light filled living room. Washer/dryer can be added for an additional $75 per month. Pets considered. Off-street parking. First month and two months security, if applicable. Credit and background check required.

    Agent Photo

    Amanda Balaski

    Northwest CT Realty

    112 Rockwell St Unit 2, Winsted, CT 06098
  • 19 Center St Unit 1, Winsted, CT 06098
    19 Center St Unit 1, Winsted, CT 06098
    19 Center St Unit 1, Winsted, CT 06098
    /8

    $1,695 Per Month

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

    19 Center St Unit 1, Winsted, CT 06098

    Three bedroom apartment on the first floor. Large kitchen, light filled living room and a recently remodeled bath. Washer/dryer can be added for an additional $75 per month. Pets considered. Off-street parking. First month and two months security, if applicable. Credit and background check required.

    Agent Photo

    Amanda Balaski

    Northwest CT Realty

    19 Center St Unit 1, Winsted, CT 06098
  • 98 Spencer St Unit 4N, Winsted, CT 06098
    98 Spencer St Unit 4N, Winsted, CT 06098
    98 Spencer St Unit 4N, Winsted, CT 06098
    /7

    $1,645 Per Month

    • 4 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • House for Rent

    98 Spencer St Unit 4N, Winsted, CT 06098

    Spacious 4 bedroom, 2nd floor apartment. Washer/dryer included. Off street parking. Pets considered. Credit and background check done by listing office. Minimum credit score required.

    Agent Photo

    Amanda Balaski

    Northwest CT Realty

    98 Spencer St Unit 4N, Winsted, CT 06098
  • 43 Wallens St Unit 1, Winsted, CT 06098
    43 Wallens St Unit 1, Winsted, CT 06098
    43 Wallens St Unit 1, Winsted, CT 06098
    /5

    $1,300 Per Month

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

    43 Wallens St Unit 1, Winsted, CT 06098

    Ranch 1 bedroom 1st fl unit, NO LAUNDRY HOOKUPS, electric heat/hot water. 1st month rent, 2 months security deposit, credit, background, renters insurance & eviction checks required. Available 8/1

    Diane Carroll The Washington Agency

    43 Wallens St Unit 1, Winsted, CT 06098
  • 88 Spencer St Unit 2, Winsted, CT 06098
    88 Spencer St Unit 2, Winsted, CT 06098
    88 Spencer St Unit 2, Winsted, CT 06098
    /3

    $1,495 Per Month

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

    88 Spencer St Unit 2, Winsted, CT 06098

    Two bedroom, 1st flr apartment close to town. Private front porch. A washer-dryer can be provided for an extra $75 per month. Pets considered, and a background and credit check are required. Minimum credit score required. Showings only in the evening or on Sundays.

    Agent Photo

    Amanda Balaski

    Northwest CT Realty

    88 Spencer St Unit 2, Winsted, CT 06098
  • I 9 Nanni Dr Unit F-09, Winchester, CT 06098
    I 9 Nanni Dr Unit F-09, Winchester, CT 06098
    I 9 Nanni Dr Unit F-09, Winchester, CT 06098
    /6

    $1,495

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 1,045 Sq Ft
    • 2 Bedroom Townhouse Apartment

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

    Discover the charm of Litchfield County living at Litchfield Heights. Our generously sized townhomes — over 1,000 square feet — have been thoughtfully upgraded with brand new white shaker cabinets, granite countertops, stainless steel appliances, and new vinyl plank flooring. Spacious bedrooms, remodeled bathrooms, private entrances, and backyard sliders round out everything you need to feel

    I 9 Nanni Dr Unit F-09, Winchester, CT 06098
  • 936 Main St Unit 14, Winchester, CT 06098
    936 Main St Unit 14, Winchester, CT 06098
    936 Main St Unit 14, Winchester, CT 06098
    /9

    $1,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,000 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. The property will look much nicer when completed. This is the final phase. Beautiful free standing ranch style homes, 2 bedroom, 2 baths with attached closed porch available. There are 2 houses available

    Michael Block Building Blocks LLC

    936 Main St Unit 14, Winchester, CT 06098
  • 267 Rockwell St Unit 1st fl, Winsted, CT 06098
    267 Rockwell St Unit 1st fl, Winsted, CT 06098
    267 Rockwell St Unit 1st fl, Winsted, CT 06098
    /12

    $1,300 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
  • 277 N Main St Unit 3, Winsted, CT 06098
    277 N Main St Unit 3, Winsted, CT 06098
    277 N Main St Unit 3, Winsted, CT 06098
    /14

    $900 Per Month

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

    277 N Main St Unit 3, Winsted, CT 06098

    Second-floor apartment available in a convenient Winsted location, close to local shops, dining, and everyday amenities. This freshly painted unit offers a bright, open living space with an efficient layout, along with an in-wall A/C unit for added comfort. The kitchen provides ample cabinet storage, and the unit is complemented by a clean, well-maintained bath. Enjoy the convenience of on-site

    Ryan Marconi The Washington Agency

    277 N Main St Unit 3, Winsted, CT 06098
  • 34 Rock St, Winsted, CT 06098
    34 Rock St, Winsted, CT 06098
    34 Rock St, Winsted, 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
  • 440 Main St Unit B, Winchester, CT 06098
    440 Main St Unit B, Winchester, CT 06098
    440 Main St Unit B, Winchester, CT 06098
    /5

    $1,000 Per Month

    • 2 Beds
    • 1 Bath
    • 4,668 Sq Ft
    • Apartment for Rent

    440 Main St Unit B, Winchester, CT 06098

    Second Floor two Bedroom room apartment set in town. Convenient to stores, restaurants and medical facility. Minimum credit score, credit checks are to be done by listing office.

    Linda Ganem Borla & Associates Real Estate

    440 Main St Unit B, Winchester, CT 06098
  • 880 W Wakefield Blvd, Winsted, CT 06098
    880 W Wakefield Blvd, Winsted, CT 06098
    880 W Wakefield Blvd, Winsted, 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
  • 101 Whiting St, Winsted, CT 06098
    101 Whiting St, Winsted, CT 06098
    101 Whiting 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
  • 13 Wallens St, Winsted, CT 06098
    13 Wallens St, Winsted, CT 06098
    13 Wallens St, 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
Connecticut Litchfield County Winchester

Newest Homes for Rent in Winchester, CT

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 $1,247 per month, though prices vary by neighborhood, size, and property type. As of July 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 $49,880 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 $1,247 per month in Winchester, CT, renters typically need to show $3,741 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 23.1, 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 and Federal Hill, each with its own character and price range.

Rental Trends in Winchester, CT

There are currently 16 homes available for rent in Winchester, CT. The median rent is $1,247 per month, with single-family homes renting at $1,500, townhouses at $1,648 and condos at $1,183.

Rental Home Trends

Number of Homes for Rent
16
Median Rent
$1,247
Median Single Family Home Rent
$1,500
Median Townhouse Rent
$1,648
Median Condo Rent
$1,183
How to Rent a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group