2 Bedroom Apartments for Rent in Chester, NY (46 Rentals)

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78 High St
2 Bedroom Apartments

78 High St

78 High StChester, NY 10918
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Green Meadows
2 Bedroom Apartments

Green Meadows

313 Green Meadows WayChester, NY 10918
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29 N Main St
2 Bedroom Apartments

29 N Main St

29 N Main StFlorida, NY 10921
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Chester, NY Local Guide

Largest Available Chester 2 Bedroom Apartments

The largest available 2 Bedroom apartment unit in Chester, NY is found at The Regency Club in the Downtown Middletown neighborhood and is 1,172 square feet priced from $1,795. Kensington Manor has the second largest 2 Bedroom, which is sized at 1,150 square feet and currently listed start at $1,895. Here is today’s list of the largest available 2 Bedroom units in Chester:

Apartment ListingModel NameSquare FootagePriced From
The Regency Club2BR/2BA1,172 Sq Ft$1,795
Kensington ManorOriginal Construction1,150 Sq Ft$1,895
Golf Links Apartments2 Beds, 2 baths1,142 Sq Ft$2,350
Sterling Parc at MiddletownHampton1,125 Sq Ft$2,406
The Point at Sutton HillThe Point Type B1,111 Sq Ft$2,420
The Park At MainC1,076 Sq Ft$2,425
Residences at West Hills Country Club2 Bedroom B1,071 Sq Ft$3,041
Sherwood Forest Garden Apartments2x11,010 Sq Ft$2,150

Cheapest Available Chester 2 Bedroom Apartments

As of March 05, 2025 the lowest priced 2 Bedroom apartment unit in Chester, NY is the 2BR/2BA Model starting from $1,795 at The Regency Club in the Downtown Middletown neighborhood. The second most affordable Chester 2 Bedroom is the 2 Bedroom Model at Knox Village starting at $1,810 in the Grove at New Windsor neighborhood. The average price for all 2 Bedroom apartments in Chester is currently $2,385. Here is today’s list of the cheapest available 2 Bedroom options in Chester:

Apartment ListingModel NamePriced From
The Regency Club2BR/2BA$1,795
Knox Village2 Bedroom$1,810
Kensington ManorOriginal Construction$1,895
Sutton Hill ApartmentsSutton Hill Type 5$1,950
Crestwood Apartments2-Bedroom$1,950
Stevens Manor Apartments2 Bedroom$1,975
Idlewild Creek Apartments2 Bedroom 1 Bathroom$1,997
Stoneridge Manor Apartments2 Beds, 2 baths$2,000
Country Manor ApartmentsTwo Bedroom$2,000
Boulder Pointe Apartments2 Bedrooms | 2 Bathrooms$2,038

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Getting Around Chester, NY

Walk Score®

29 / 100

Car-Dependent

Most errands require a car

Bike Score®

23 / 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 Regency Club listed at $1,795.

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

The average rent for a 2 Bedroom Apartment in Chester is $2,385.

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

Today's apartment with the most square footage in Chester is a 1,172 square feet unit starting from $1,795 at The Regency Club.

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

The average size for a 2 Bedroom rental in Chester is currently 1,526 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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Battling the Butts: Your Guide to the Reality of Smoke-Free Renting

Written by: Andrea Lee Negroni, JD

While many apartment buildings are “no smoking” properties, it’s hard to know exactly how many. In 2017, the National Apartment Association reported more than half of rental properties had smoke free policies.

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Understanding Amenity Fees: Know Where You Might Be Able to Save Money

Written by: Amber Kanuckel

With the rising costs of housing, a lot of renters are asking this question: Is it possible to opt out of various amenities that your rental property offers so that you can avoid paying the fees.

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How Your Move-In Inspection Can Protect Your Security Deposit

Written by: Christine Leonard, Esq.

If you’re anything like most people, housing costs represent a huge chunk of your monthly budget. On top of that, moving can be both a stressful and expensive affair.

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Signing Your Apartment Lease: The Basics

Written by: Trey Huguley

When you're about to sign a lease for the first time, it can feel a bit overwhelming. You don’t want to miss any important details hidden in the fine print.