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Apartments for Rent in Winchester, CT under $2000

Apartments for Rent in Winchester, CT under $2000. 11 Rentals Available
11 Rentals Available
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  • A kitchen with wooden cabinets and a white countertop.
    1 bd $875
    Base rent
    Verified Listing

    279 N Main St, Winchester, CT 06098
  • A kitchen with wooden cabinets and a white stove top oven.
    3 bd $1,700
    Base rent
    Verified Listing

    17 Union Street, Winsted, CT 06098
    Dog friendly

  • More Rentals Near Winchester, CT

  • a living room with a white couch and a table
    Only 2 units left
    1 bd $1,950+
    Base rent
    Verified Listing

    3.0 (2)
    33 Woodruff Lane, Litchfield, CT 06759
    Apply online • Pet friendly
  • a kitchen with a sliding glass door and a stove
    Ask for pricing
    Verified Listing

    5.0 (5)
    4 Terrace Drive, Torrington, CT 06790
    Pet friendly
  • a living room filled with furniture and a bed
    Ask for Pricing
    Income restricted
    Verified Listing

    356 Torringford West Street, Torrington, CT 06790
    Pet friendly
  • a living room with a couch and a tv
    Ask for pricing
    Verified Listing

    3.5 (5)
    23-24 Holly House Court, Litchfield, CT 06759
    Pet friendly
  • a small living room with a chair and a table
    Ask for pricing
    Verified Listing

    4.0 (56)
    200 Hopmeadow Street, Simsbury, CT 06089
    Pet friendly
  • a kitchen with stainless steel appliances and white cabinets
    Ask for pricing
    Verified Listing

    4.0 (23)
    1175 Farmington Ave, Bristol, CT 06010
    Pet friendly
  • A kitchen with wooden cabinets and a stainless steel refrigerator.
    3 bd $1,550
    Base rent
    Verified Listing

    58 Pulaski St, Torrington, CT 06790
  • A living room with a red couch and a coffee table.
    2 bd $1,550
    Base rent
    Verified Listing

    24 Dewey St, Torrington, CT 06790
2-8-town

Frequently asked questions

When were prices and availability in Winchester, CT last updated?

Prices and availability in Winchester, CT were last updated on 27 May 2026.

What are the best apartments in Winchester, CT?

The best apartments in Winchester, CT are: 279 N Main St, Unit 5 and 17 Union Street, Unit Second Floor.

What type of rental buildings are in Winchester, CT?

In Winchester 34% of the housing is rented out compared to 66% of homes are owned, according to the most recent Census Bureau estimates. 8% of Winchester's apartments are found in large buildings of 50 units or more, 88% are located in smaller apartment complexes with less than 50 units, and 4% are single-family rentals.