2 Bedroom Apartments for Rent in Chester, NY (63 Rentals)

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18 Main St
2 Bedroom Apartments

18 Main St

18 Main StChester, NY 10918
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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

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Meadow Hills
2 Bedroom Apartments

Meadow Hills

44 High StChester, NY 10918
  • Utilities Included

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

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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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property at 26 E Main St

26 E Main St

WaldenNY12586

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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Chester, NY Local Guide

Largest Available Chester 2 Bedroom Apartments

The largest available 2 Bedroom apartment unit in Chester, NY is found at The 211 Luxury Lofts in the Downtown Middletown neighborhood and is 1,500 square feet priced from $2,300. The Regency Club in the Presidential Heights neighborhood has the second largest 2 Bedroom, which is sized at 1,172 square feet and currently listed start at $2,500. Here is today’s list of the largest available 2 Bedroom units in Chester:

Apartment ListingModel NameSquare FootagePriced From
The 211 Luxury Lofts2 Bed 1 Bath1,500 Sq Ft$2,300
The Regency Club2BR/2BA1,172 Sq Ft$2,500
Kensington ManorOriginal Construction1,150 Sq Ft$1,895
The Park At MainC1,076 Sq Ft$2,425
Idlewild Creek Apartments2 Bedroom 1 Bathroom1,063 Sq Ft$1,907
Carriage Hill Apartments2 BR1,025 Sq Ft$2,200
Imperial Gardens Apartment HomesTwo Bedroom 1.5 Bath-990 sqft990 Sq Ft$2,040
Woodbury GardensTwo Bedroom920 Sq Ft$2,200
Knox Village2 Bedroom900 Sq Ft$1,810

Cheapest Available Chester 2 Bedroom Apartments

As of September 16, 2025 the lowest priced 2 Bedroom apartment unit in Chester, NY is the 2 Bedroom Model starting from $1,810 at Knox Village . The second most affordable Chester 2 Bedroom is the 2 Bedroom 1 Bathroom Model at Idlewild Creek Apartments starting at $1,882 . The average price for all 2 Bedroom apartments in Chester is currently $2,099. Here is today’s list of the cheapest available 2 Bedroom options in Chester:

Apartment ListingModel NamePriced From
Knox Village2 Bedroom$1,810
Idlewild Creek Apartments2 Bedroom 1 Bathroom$1,882
Kensington ManorOriginal Construction$1,895
Crestwood Apartments2-Bedroom$1,950
Imperial Gardens Apartment HomesTwo Bedroom-916 sqft$1,980
Stoneridge Manor Apartments2 Beds, 2 baths$2,000
Stevens Manor Apartments2 Bedroom$2,150
Carriage Hill Apartments2 BR$2,200
Rockwood Gardens Apartments2 Beds, 1 bath$2,200
Woodbury GardensTwo Bedroom$2,200

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

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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 $2,099.

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

Today's apartment with the most square footage in Chester is a 1,500 square feet unit starting from $2,300 at The 211 Luxury Lofts.

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

The average size for a 2 Bedroom rental in Chester is currently 970 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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The Rental Move-In Inspection Checklist: A Guide for Renters

Written by: Trey Huguley

The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.

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Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between

Written by: Christine Leonard, Esq.

For many people, obstacles can arise during the rental application process for a variety of issues.

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

Written by: Christine Leonard, Esq.

Hard truth. Moving is never easy. I’ve done it all – from local moves to cross-country relocations From packing to unpacking the last box, I have found moving to be an exhausting, expensive and stressful experience every time.

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

Written by: Christine Leonard, Esq.

Throughout the day, think about all the times that you have to pay for something. So many of us reach automatically for a credit card or even our phone for a quick payment.