Apartments for Rent in Chester, CT Under $2,000 (49 Rentals)

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property at 159 Main St

$1,950

Total Monthly Price

Total Monthly Price

Base Rent
$1,950

Total Monthly Price
$1,950

2 Bedroom Rentals

Available Now

159 Main St

ChesterCT06412
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Springside Middletown
Rent Specials
$1,955 - $3,895
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$1,800 - $3,740
Required Monthly Fees
$155

Total Monthly Price
$1,955 - $3,895
1 to 3 Bedroom Apartments Available Now

Springside Middletown

1100 Springside LnMiddletown, CT 06457
Outdoors
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  • Customer Reviewed
  • 3D Tour
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Knoll Crest Apartments
Rent Specials
$1,906 - $5,010
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$1,796 - $4,900
Required Monthly Fees
$110

Total Monthly Price
$1,906 - $5,010
1 to 2 Bedroom Apartments Available Now

Knoll Crest Apartments

207 George StMiddletown, CT 06457
Furnished
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  • Customer Reviewed
  • 3D Tour
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The Sound at Gateway Commons
Rent Specials
$1,815 - $3,065
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$1,800 - $3,050
Required Monthly Fees
$15

Total Monthly Price
$1,815 - $3,065
Studio to 3 Bedroom Apartments Available Now

The Sound at Gateway Commons

1 Maple Tree LnEast Lyme, CT 06333
Affordability
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  • Customer Reviewed
  • Utilities Included
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Colchester Estates
$1,800 - $1,830
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$1,800 - $1,830

Total Monthly Price
$1,800 - $1,830
2 Bedroom Apartments Available Now

Colchester Estates

12 Balaban RdColchester, CT 06415
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  • Customer Reviewed

The Art of the Rental Viewing: What to look for during a property tour

Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.

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Four Seasons of Colchester
Rent Specials
$1,700 - $2,100
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$1,700 - $2,100

Total Monthly Price
$1,700 - $2,100
1 to 2 Bedroom Apartments Available Now

Four Seasons of Colchester

343 Lebanon AveColchester, CT 06415
Luxury
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  • Customer Reviewed
  • Utilities Included
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Marshfield Apartments
Rent Specials
$1,650 - $2,180
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$1,635 - $2,165
Required Monthly Fees
$15

Total Monthly Price
$1,650 - $2,180
1 to 2 Bedroom Apartments Available Now

Marshfield Apartments

1739 Foxon RdNorth Branford, CT 06471
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  • Customer Reviewed
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Middletown Brooke Apartments
Rent Specials
$1,628 - $2,995
Total Monthly Price

Total Monthly Price

Base Rent
$1,628 - $2,995

Total Monthly Price
$1,628 - $2,995
1 to 2 Bedroom Apartments Available Now

Middletown Brooke Apartments

100 Town BrookeMiddletown, CT 06457
Furnished
  • Verified
  • Customer Reviewed
  • 3D Tour

Smart Renter's Guide: Calculating Affordable Rent & Housing Costs

Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.

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Sagamore Hills
$1,588 - $1,950
Total Monthly Price

Total Monthly Price

Base Rent
$1,536 - $1,898
Required Monthly Fees
$52

Total Monthly Price
$1,588 - $1,950
1 to 2 Bedroom Apartments Available Now

Sagamore Hills

1151-1189 Washington StMiddletown, CT 06457
Corporate Housing
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  • Customer Reviewed
  • Utilities Included
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Meadoway Gardens
Rent Specials
$1,400 - $2,200
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$1,400 - $2,200

Total Monthly Price
$1,400 - $2,200
1 to 3 Bedroom Apartments Available Now

Meadoway Gardens

121-122 Rose CirMiddletown, CT 06457
Family Friendly
  • Verified
  • Utilities Included
  • Low Income

Navigating the Rental Market: Tips for First-Time Renters

Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.

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Highview Apartments
$1,395 - $1,425
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$1,395 - $1,425

Total Monthly Price
$1,395 - $1,425
1 Bedroom Apartments Available Now

Highview Apartments

121-131 Butternut StMiddletown, CT 06457
Pet Friendly
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  • Customer Reviewed
  • Utilities Included
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Country Place
$1,315 - $1,670
Total Monthly Price

Total Monthly Price

Base Rent
$1,315 - $1,670

Total Monthly Price
$1,315 - $1,670
1 to 3 Bedroom Apartments Contact Us For Availability

Country Place

1 Birch CirColchester, CT 06415
Cost Per Sq.Ft.
  • Verified
  • Low Income
property at 23 College St

$1,900

Total Monthly Price

Total Monthly Price

Base Rent
$1,900

Total Monthly Price
$1,900

2 Bedroom, 1 Bath Condo for Rent

Available Now

23 College St

ClintonCT06413
property at 144 E Main St

$1,900

Total Monthly Price

Total Monthly Price

Base Rent
$1,900

Total Monthly Price
$1,900

2 Bedroom, 1 Bath Townhome for Rent

Available Jan 1, 2026

144 E Main St

ClintonCT06413
property at 70 Pond Meadow Rd

$1,800

Total Monthly Price

Total Monthly Price

Base Rent
$1,800

Total Monthly Price
$1,800

2 Bedroom, 1 Bath Condo for Rent

Available Now

70 Pond Meadow Rd

EssexCT06442
property at 25 Park Rd

$1,795

Total Monthly Price

Total Monthly Price

Base Rent
$1,795

Total Monthly Price
$1,795

1 Bedroom, 1 Bath Home for Rent

Available Now

25 Park Rd

EssexCT06442
property at 255 Rte 80

$1,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$1,600

Total Monthly Price
$1,600

1 Bedroom, 1 Bath Home for Rent

Available Now

255 Rte 80

KillingworthCT06419
property at 119 Kelseytown Rd

$1,250

Total Monthly Price

Total Monthly Price

Base Rent
$1,250

Total Monthly Price
$1,250

1 Bedroom, 1 Bath Home for Rent

Available Now

119 Kelseytown Rd

ClintonCT06413
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The Wilcox
1 to 3 Bedroom Apartments

The Wilcox

305-309 S Main StMiddletown, CT 06457
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584 Main St
Studio Apartments

584 Main St

584 Main StMiddletown, CT 06457
  • Utilities Included
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26 Sunset Ter
1 to 2 Bedroom Apartments

26 Sunset Ter

26 Sunset TerEssex, CT 06426

Chester, CT Local Guide

Don't Settle: How to Negotiate Your Apartment Lease and Save Money

Discover the insider tips from an attorney and real estate agent on how to negotiate your next apartment lease. Find out what's on the table and what's not, so you can save money and get the best terms possible.

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The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro

Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.

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Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting

Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.

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Quick Rent Budget Calculator

How much rent can you afford?

The common "Rule of Thumb" is that rent should be no more than 30% of your income. How much is that? Enter your monthly income and click "Calculate My Budget" to find out.

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Remember the 3 Rules of Real Estate:
Location, Location, Location!

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Frequently Asked Questions about Chester

How much are Studio apartments in Chester?

There are currently 13 Studio Apartments in Chester with rent ranges from $975 to $2,071 with an average price of $1,611.

What is the current price range for One Bedroom Chester Apartments for rent?

Today's rental pricing for One Bedroom Apartments in Chester ranges from $710 to $3,517 with an average monthly rent of $1,992.

What does renting a Two Bedroom Apartment in Chester cost?

The monthly rent prices of Two Bedroom Apartments currently available in Chester range from $864 to $4,428. Today's average rental price for Two Bedrooms here is $2,495.

How expensive are Chester Three Bedroom Apartments?

There are currently 17 Three Bedroom Apartments listings available in Chester on ApartmentHomeLiving.com. The pricing ranges from $1,670 to $3,895 - averaging $2,975 for the location.

Expert Rental Resources

The rental experts at ApartmentHomeLiving.com provide you with top advice, tools, and tips for understanding the leasing process and finding the perfect rental. Here are a few helpful rental and leasing articles from our experts to guide you on your search.

Articles, How-To's, and Tips

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How to Make Your Apartment Holiday-Ready: Renter-Friendly Tips

Written by: Justin Habersaat

Getting your apartment ready for the holidays can be exciting but sometimes challenging in a smaller space. Here are some modern tips to keep things festive, safe, and inviting this season.

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Renting with Roommates: Realistic Expectations for Shared Lease

Written by: Christine Leonard, Esq.

Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.

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Apartment Common Area Rules: What Renters Need to Know

Written by: Christine Leonard, Esq.

Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.

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How to Negotiate Your Apartment Lease and Save Money

Written by: Christine Leonard, Esq.

Everything is a negotiation in real estate!