12

Winchester, CT Homes for Rent under $2,000

Section Image Section Image
  • 112 Rockwell St Unit 1, Winsted, CT 06098
    112 Rockwell St Unit 1, Winsted, CT 06098
    112 Rockwell St Unit 1, Winsted, CT 06098
    /8

    $1,395 per month

    • 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
  • 79 Chestnut St, Winsted, CT 06098
    79 Chestnut St, Winsted, CT 06098
    79 Chestnut St, Winsted, CT 06098
    /10

    $1,450 per month

    • 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
  • 112 Rockwell St Unit LL, Winsted, CT 06098
    112 Rockwell St Unit LL, Winsted, CT 06098
    112 Rockwell St Unit LL, Winsted, CT 06098
    /7

    $1,150 per month

    • 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
  • 113 Elm St Unit Left, Winsted, CT 06098
    113 Elm St Unit Left, Winsted, CT 06098
    113 Elm St Unit Left, Winsted, CT 06098
    /4

    $165 per month

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

    $165 per month

    • 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
  • 244 Walnut St, Winsted, CT 06098
    244 Walnut St, Winsted, CT 06098
    /2

    $1,500 per month

    • 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
  • 102 Elm St, Winsted, CT 06098
    102 Elm St, Winsted, CT 06098
    102 Elm St, Winsted, CT 06098
    /21

    $1,550 per month

    • 3 Beds
    • 1.5 Baths
    • 1,178 Sq Ft
    • House for Rent

    102 Elm St, Winsted, CT 06098

    3 bedroom apartment close to down town. This unit has the living space on the first floor and the bedrooms and full bath on the second floor. There are hardwood floors through most of the unit. A walk-up attic and basement can be used for storage.

    Agent Photo

    Jeffrey Liskin

    Northwest CT Realty

    (860) 390-5901

    102 Elm St, Winsted, CT 06098
  • 101 Whiting St, Winsted, CT 06098
    101 Whiting St, Winsted, CT 06098
    101 Whiting St, Winsted, CT 06098
    /34

    $1,500 - $1,800 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
  • 440 Main St Unit C, Winchester, CT 06098
    440 Main St Unit C, Winchester, CT 06098
    440 Main St Unit C, Winchester, CT 06098
    /3

    $800 per month

    • 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
  • 13 Wallens St, Winsted, CT 06098
    13 Wallens St, Winsted, CT 06098
    13 Wallens St, Winsted, CT 06098
    /20

    $1,150 - $1,550 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
  • 50 Benton St, Winsted, CT 06098
    50 Benton St, Winsted, CT 06098
    50 Benton St, Winsted, CT 06098
    /30

    $1,495 per month

    • 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
  • 22 Upson Ave, Winsted, CT 06098
    22 Upson Ave, Winsted, CT 06098
    22 Upson Ave, Winsted, CT 06098
    /10

    $1,500 per month

    • 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
Connecticut Litchfield County Winchester

Homes for Rent in Winchester, CT under $2,000

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