Apartments for Rent in Chester, CT under $2000
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Studio $1,1452 bd $1,595+Base rent4.5 (3)28 High Street, Chester, CT 06412 -
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Studio $1,250+1 bd $1,195Base rent3.5 (1)30 High Street, Chester, CT 06412 -
More Rentals Near Chester, CT
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Only 1 unit left3 bd $1,800Base rent26-28 High Street, Clinton, CT 6413Apply online • Pet friendly -
Only 1 unit leftStudio $1,2881 bd $1,165Base rent61 Cedar Street, Rockfall, CT 06481Pet friendly -
Only 3 units left1 bd $1,3192 bd $9003 bd $1,000Base rent1 Birch Circle, Colchester, CT 06415Pet friendly
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Only 1 unit left1 bd $1,3192 bd $1,5073 bd $1,679Base rent1 Birch Circle, Colchester, CT 06415Pet friendly
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2 bd $1,7003 bd $2,000Base rent Income restricted3.5 (20)63 Stoneycrest Drive, Middletown, CT 06457Apply online • Pet friendly • In unit laundry
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Studio $1,1331 bd $1,4002 bd $1,730Base rent4.0 (7)352 Newfield Street, Middletown, CT 06457Apply online • Pet friendly • In unit laundry
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Studio $9501 bd $925+2 bd $1,366Base rent3.0 (2)1005 Saybrook Rd, Haddam, CT 06438 -
1 bd $1,4002 bd $1,710Base rent4.0 (19)288 Woodbury Circle, Middletown, CT 06457Pet friendly • In unit laundry • Dishwasher
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1 bd $1,4002 bd $1,710Base rent3.5 (29)288 Woodbury Circle, Middletown, CT 6457Pet friendly • In unit laundry • Dishwasher
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1 bd $1,4002 bd $1,710Base rent4.5 (6)15 Summer Hill Road, Middletown, CT 06457Pet friendly • In unit laundry • Dishwasher
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Ask for Pricing770 Boston Post Road, Guilford, CT 06437Cat friendly • Parking • High Speed Internet
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Ask for Pricing1250,1300 And 1310 Boston Post Road, Guilford, CT 06437Cat friendly • Air conditioner • Hardwood Floors
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Ask for pricingIncome restricted5.0 (1)251 Court St, Middletown, CT 06459Pet friendly • In unit laundry • Air conditioner
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3 bd $2,000Base rent3.5 (34)20 Plaza Drive, Middletown, CT 06457Pet friendly • In unit laundry • Dishwasher
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Studio $1,1331 bd $1,4002 bd $1,730Base rent3.5 (4)220 Newfield Street, Middletown, CT 06457Pet friendly • In unit laundry • Dishwasher
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1 bd $1,4002 bd $1,7003 bd $2,000Base rent3.5 (16)121 Rose Circle, Middletown, CT 06457Pet friendly • In unit laundry • Dishwasher
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Ask for pricing4.0 (10)656 E Center Street, Wallingford, CT 06492Pet friendly • Fitness center • In unit laundry
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Studio $1,2001 bd $1,4472 bd $1,767Base rent3.5 (13)410 East Main Street, Meriden, CT 06450Pet friendly • Pool • In unit laundry
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Ask for pricing181 Knollwood Drive, Wallingford, CT 06492Pet friendly • Fitness center • Pool
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1 bd $1,529Base rent4.5 (3)300 Britannia Street, Meriden, CT 06450Pet friendly • In unit laundry • Dishwasher
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1 bd $1,4442 bd $1,760Base rent4.0 (9)98 Hall Avenue, Meriden, CT 06450Pet friendly • Parking • In unit laundry
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Ask for pricing5.0 (2)175 Brushy Plain Road, Branford, CT 06405Cat friendly • Parking • In unit laundry
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1 bd $1,5292 bd $1,767Base rent3.5 (6)51 Park Street, Meriden, CT 06450Pet friendly • In unit laundry • Dishwasher
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Frequently asked questions
When were prices and availability in Chester, CT last updated?
Prices and availability in Chester, CT were last updated on 8 Jul 2026.
What are the best apartments in Chester, CT?
The best apartments in Chester, CT are: 28 High Street and 30 High Street.
What type of rental buildings are in Chester, CT?
In Chester 27% of the housing is rented out compared to 73% of homes are owned, according to the most recent Census Bureau estimates. 7% of Chester's apartments are found in large buildings of 50 units or more, 67% are located in smaller apartment complexes with less than 50 units, and 26% are single-family rentals.
Apartments in Chester, CT under $2,000
Balancing snug and cheap is no joke when it comes to renting a place to live. “Are there any apartments near me under $2,000?” is a great question to start from. Knowing your budget means you’re one step ahead and on the right track. We’ve taken care of the rest and found 38 apartments for rent in Chester, CT on which you’ll spend less than $2,000. A small, cheap rental means you’ll have to budget your living space as well. The great news is that keeping it simple pays off in more than one way. The cost of utilities is likely to run low, and you get the added benefit of not having to spend too much time cleaning up the whole place. Smaller apartments are more likely to be closer to the city center, so there are potential cuts to your transportation costs too. And here’s one more very special secret to add to your book-of-perks: you’re less likely to overshop when you know your space is limited.
Rentals near you under $2,000
Our goal is to help you find cheap apartments that live up to your dreams without crushing your budget. It may be a long shot to go looking for 3 bedroom apartments or even 2 bedroom for less than $2,000. The average rental size in Chester, CT is 874 Sqft, but the $2,000 limit will probably narrow your search to places with a smaller square footage. Go through our listings and be on the look-out for a hassle-free studio or a 1 bedroom apartment. We trust you’ll turn it into a cozy home which is also budget-friendly to the core.