2 Bedroom Apartments for Rent in Chester, NY (48 Rentals)

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Green Meadows
2 Bedroom Apartments

Green Meadows

313 Green Meadows WayChester, NY 10918
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78 High St
2 Bedroom Apartments

78 High St

78 High StChester, NY 10918

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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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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Golf Links Apartments
2 Bedroom Apartments

Golf Links Apartments

206 Golf Links RdMiddletown, NY 10940
  • Utilities Included
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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 Presidential Heights 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
The Point at Sutton HillThe Point Type B1,111 Sq Ft$2,420
The Park At MainC1,076 Sq Ft$2,425
Idlewild Creek Apartments2 Bedroom 1 Bathroom1,063 Sq Ft$1,968
Carriage Hill Apartments2 BR1,025 Sq Ft$2,200
Rockwood Gardens Apartments2 Beds, 1 bath934 Sq Ft$2,200
Woodbury GardensTwo Bedroom920 Sq Ft$2,200
Knox Village2 Bedroom900 Sq Ft$1,810

Cheapest Available Chester 2 Bedroom Apartments

As of June 20, 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 Presidential Heights neighborhood. The average price for all 2 Bedroom apartments in Chester is currently $2,356. 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
Crestwood Apartments2-Bedroom$1,950
Sutton Hill ApartmentsSutton Hill Type 5$1,950
Idlewild Creek Apartments2 Bedroom 2 Bathroom$1,968
Country Manor ApartmentsTwo Bedroom$2,000
Stoneridge Manor Apartments2 Beds, 2 baths$2,000
Imperial Gardens Apartment HomesTwo Bedroom-933 sqft$2,070
Carriage Hill Apartments2 BR$2,200
Rockwood Gardens Apartments2 Beds, 1 bath$2,200

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Location, Location, Location!

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See the most popular apartments and homes in Chester, NY

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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 Knox Village listed at $1,810.

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

The average rent for a 2 Bedroom Apartment in Chester is $2,356.

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 1,110 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.