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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6 Glenmere Ave

FloridaNY10921
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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 $2,500. 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$2,500
Kensington ManorOriginal Construction1,150 Sq Ft$1,895
Golf Links Apartments2 Beds, 2 baths1,142 Sq Ft$2,350
The Park At MainC1,076 Sq Ft$2,425
Northwoods ApartmentsNW Unit Type B1,050 Sq Ft$2,320
Carriage Hill Apartments2 BR1,025 Sq Ft$2,200
Idlewild Creek Apartments2 Bedroom 2 Bathroom993 Sq Ft$2,015
Imperial Gardens Apartment HomesTwo Bedroom 1.5 Bath-990 sqft990 Sq Ft$2,175
Boulder Pointe Apartments2 Bedrooms | 2 Bathrooms954 Sq Ft$2,276
Knox Village2 Bedroom900 Sq Ft$1,810

Cheapest Available Chester 2 Bedroom Apartments

As of April 27, 2025 the lowest priced 2 Bedroom apartment unit in Chester, NY is the 2 Bedroom Model starting from $1,810 at Knox Village in the Grove at New Windsor neighborhood. The second most affordable Chester 2 Bedroom is the Original Construction Model at Kensington Manor starting at $1,895 in the Downtown Middletown neighborhood. The average price for all 2 Bedroom apartments in Chester is currently $2,446. Here is today’s list of the cheapest available 2 Bedroom options in Chester:

Apartment ListingModel NamePriced From
Knox Village2 Bedroom$1,810
Kensington ManorOriginal Construction$1,895
Idlewild Creek Apartments2 Bedroom 1 Bathroom$1,938
Sutton Hill ApartmentsSutton Hill Type 5$1,950
Crestwood Apartments2-Bedroom$1,950
Country Manor ApartmentsTwo Bedroom$2,000
Stoneridge Manor Apartments2 Beds, 2 baths$2,000
Imperial Gardens Apartment HomesTwo Bedroom-933 sqft$2,140
Carriage Hill Apartments2 BR$2,200
Stevens Manor Apartments2 Bedroom$2,200

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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

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

The average rent for a 2 Bedroom Apartment in Chester is $2,446.

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 $2,500 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 1,004 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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Written by: Brandie Parton

As a digital nomad, you no longer call a set address or office building your home for eight hours of the day or more.

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Know Your Rights - How Discrimination Laws Impact Landlords and Tenants

Written by: Christine Leonard, Esq.

Everyone needs a place to live and to call home. For decades, the federal government has established protections to ensure that individuals and families can find housing free from discriminatory barriers.

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Renting Smart: Lease Basics Every Renter Needs

Written by: Christine Leonard, Esq.

Often, in the excitement of finding a new place to live, there’s a rush to make it happen, and - too often - a new tenant signs a lease without reading it carefully.

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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.