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Apartments for Rent in Winchester, CT under $2000

Apartments for Rent in Winchester, CT under $2000. 9 Rentals Available
9 Rentals Available
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  • 1 bd $800
    Base rent
    Verified Listing

    279 N Main St, Winchester, CT 06098
  • 3 bd $1,800
    Base rent
    Verified Listing

    335 Taylor Brook Road, Winchester, CT 06098
    Dishwasher

  • More Rentals Near Winchester, CT

  • Only 2 units left
    1 bd $1,895
    Base rent
    Verified Listing

    3.5 (5)
    23-24 Holly House Court, Litchfield, CT 06759
    Apply online • Pet friendly • In unit laundry
  • Ask for pricing
    Verified Listing

    5.0 (5)
    4 Terrace Drive, Torrington, CT 06790
    Pet friendly • Parking • In unit laundry
  • Ask for Pricing
    Income restricted
    Verified Listing

    356 Torringford West Street, Torrington, CT 06790
    Pet friendly • In unit laundry • High Speed Internet
  • Ask for pricing
    Verified Listing

    4.0 (23)
    1175 Farmington Ave, Bristol, CT 06010
    Pet friendly • Fitness center • In unit laundry
  • 3 bd $1,550
    Base rent
    Verified Listing

    58 Pulaski St, Torrington, CT 06790
    Dishwasher • Patio/Balcony
  • 3 bd $2,000
    Base rent
    Verified Listing

    252 Funston Avenue, Torrington, CT 06790
    Dishwasher
2-6-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 Jul 2026.

What are the best apartments in Winchester, CT?

The best apartments in Winchester, CT are: 279 N Main St, Unit 8 and 335 Taylor Brook Road.

What type of rental buildings are in Winchester, CT?

In Winchester, 34% of the residents are renting compared to 66% owning a home, according to data from the U.S. Census Bureau. Large-scale apartment buildings with more than 50 units represent 8% of Winchester's rentals, 88% are small-scale complexes with under 50 units, and 4% are single-family rentals.

Search for apartments in Winchester, CT under $2,000

There’s more than one way to spend $2,000 on rent in Winchester, CT, so the first step is to start thinking about what you really want from your new home. Be mindful of what makes you tick. Look for 2 bedroom apartments for rent for less than $2,000 if you want to share your living space and don’t mind being further away from the city center. Search for 3 bedroom apartments if you’re moving in with family or planning to share part of your life and living expenses with more friends. If city bustle is what you live for, you might want to search for a studio or 1 bedroom apartment closer to the city center.

The perfect $2,000 rental near you

Don’t dismiss the idea of a studio just because it sounds small and featureless: studios come in many shapes and sizes, and it only takes a few strikes of creativity to go from drab to lively. If an all-in-one-room apartment spells total lack of privacy for you, have a look at the 1 bedroom apartments for rent in Winchester, CT. Customize your search by using more RentCafe filters. Decide what amenities you can’t live without and focus your search on the apartments that offer them. Are you bringing in a pet? Narrow your options to pet-friendly apartments for rent. Want more windows so that natural light floods your home? Hardwood floors or plush carpet in the living area? There are 8 apartments for rent below $2,000 in Winchester, CT for every taste. Decide what you need, stay focused, and you’re bound to find your perfect apartment in no time.