2 Bedroom Apartments for Rent in Chester, CT (47 Rentals)

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Roommate Matching: Finding the Right Fit and Avoiding Pitfalls

When searching for a roommate, follow this list of essential steps and set clear expectations to create a solid foundation for a harmonious living situation.

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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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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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562 Main St
2 Bedroom Apartments

562 Main St

562 Main StMiddletown, CT 06457
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The Wilcox
2 Bedroom Apartments

The Wilcox

305-309 S Main StMiddletown, CT 06457

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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StoneGate Apartments
2 Bedroom Apartments

StoneGate Apartments

1150-1160 S Main StMiddletown, CT 06457
  • Utilities Included
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Blueway Commons
2 Bedroom Apartments

Blueway Commons

3 Brookes CtHaddam, CT 06438
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The Grand
2 Bedroom Apartments

The Grand

9-15 John StClinton, CT 06413
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113 Union St
2 Bedroom Apartments

113 Union St

113 Union StDeep River, CT 06417
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93 Main St
2 Bedroom Apartments

93 Main St

93 Main StDeep River, CT 06417
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Chester, CT Local Guide

Largest Available Chester and Nearby 2 Bedroom Apartments

The largest available 2 Bedroom apartment unit in Chester, CT is found at The Cove at Gateway Commons in the Southwest New London Lyme neighborhood and is 1,523 square feet priced from $3,325. Springside Middletown in the Cromwell Middletown neighborhood has the second largest 2 Bedroom, which is sized at 1,461 square feet and currently listed start at $3,140. Here is today’s list of the largest available 2 Bedroom units in Chester:

Apartment ListingModel NameSquare FootagePriced From
The Cove at Gateway CommonsCape Townhouse1,523 Sq Ft$3,325
Springside MiddletownTB1 | 2 Bed | 2.5 Bath1,461 Sq Ft$3,140
Brainerd PlaceB21,373 Sq Ft$3,120
The ArloFarmington1,188 Sq Ft$2,788
Blueway CommonsColumbia1,180 Sq Ft$2,279
Northwoods EastB1E1,129 Sq Ft$2,254
Knoll Crest ApartmentsMaplewood1,120 Sq Ft$2,547
The Sound at Gateway CommonsThe Waterford1,115 Sq Ft$2,525
Middletown Brooke ApartmentsThe Westlake1,052 Sq Ft$2,306
Colchester EstatesBeautiful Remodeled and Upgraded Townhouse in C...1,000 Sq Ft$1,800

Cheapest Available Chester and Nearby 2 Bedroom Apartments

As of June 20, 2025 the lowest priced 2 Bedroom apartment unit in Chester, CT is the 2B/1B Medium Model starting from $1,550 at The Wilcox in the East Hampton Portland neighborhood. The second most affordable Chester 2 Bedroom is the Two Bedroom Townhouse Model at Meadoway Gardens starting at $1,700 in the Cromwell Middletown neighborhood. The average price for all 2 Bedroom apartments in Chester is currently $2,594. Here is today’s list of the cheapest available 2 Bedroom options in Chester:

Apartment ListingModel NamePriced From
The Wilcox2B/1B Medium$1,550
Meadoway GardensTwo Bedroom Townhouse$1,700
The Village at 82 Main2 Beds, 1 Baths$1,700
Fernwood Apartments2 Bedroom$1,750
Colchester EstatesBeautiful Remodeled and Upgraded Townhouse in C...$1,800
South Green ApartmentsTwo Bedroom$1,893
Marshfield ApartmentsTwo Bedroom$2,050
Middletown Brooke ApartmentsThe Mattabeseck$2,241
Northwoods EastB1E$2,254
Southwind ApartmentsTwo Bedroom$2,275

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

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See the most popular apartments and homes in Chester, CT

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Getting Around Chester, CT

Walk Score®

29 / 100

Car-Dependent

Most errands require a car

Bike Score®

17 / 100

Somewhat Bikeable

Minimal bike infrastructure

What Are Walk Score®, Transit Score®, and Bike Score® Ratings?

  • Walk Score® measures the walkability of any address.
  • Transit Score® measures access to public transit.
  • Bike Score® measures the bikeability of any address.

Frequently Asked Questions about 2 Bedroom Chester Apartments

What is the Cheapest apartment in Chester with 2 Bedroom?

Currently the most affordable 2 Bedroom in Chester is at The Wilcox listed at $1,550.

How much is the average rent for a 2 Bedroom Chester Apartment?

The average rent for a 2 Bedroom Apartment in Chester is $2,594.

What is the largest available 2 Bedroom Chester Apartment for rent?

Today's apartment with the most square footage in Chester is a 1,523 square feet unit starting from $3,325 at The Cove at Gateway Commons.

What is the average size for Chester 2 Bedroom Apartments for rent?

The average size for a 2 Bedroom rental in Chester is currently 1,479 sq ft.

Expert Rental Resources

Helpful Apartment Articles, How-To's and Tips

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.

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Roommate Matching: Finding the Right Fit and Avoiding Pitfalls

Written by: Cheryl Bowman

A fantastic way to save money and enjoy a built-in community is to share an apartment. However, a bad roommate situation can turn your dream rental into a nightmare.

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

Written by: Marie Brown

You’ve scrolled through countless listings, walked through a blur of rentals, and finally found what feels like the one. The pictures? Fantastic. The neighborhood seems just right.

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Know Your Budget: Calculating What You Can Realistically Afford When Renting

Written by: Lauren Harrington

Renting an apartment or house isn’t just about looking through online ads, choosing a few apartments or homes you want to tour, filling out an application, and putting down a deposit. Those things are all necessary and important.

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The Freedom of Short-Term Leases: Exploring the Advantages for Renters

Written by: Bobbi Jackson

If you’re looking to relocate right now, a popular solution that may best fit your current rental needs is a short-term lease.