2 Bedroom Apartments for Rent in Chester, NY (53 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
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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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Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting

Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.

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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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29 N Main St
2 Bedroom Apartments

29 N Main St

29 N Main StFlorida, NY 10921

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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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. Southgate Middletown in the Middletown Goshen neighborhood has the second largest 2 Bedroom, which is sized at 1,302 square feet and currently listed start at $3,000. 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
Southgate MiddletownB-2B3 3rd Floor1,302 Sq Ft$3,000
Pulaski1,300 Sq Ft$1,900
Summit Terrace Luxury ApartmentsWestchester1,179 Sq Ft$2,500
Kensington ManorOriginal Construction1,150 Sq Ft$1,895
Sterling Parc at MiddletownHampton1,125 Sq Ft$2,757
The Point at Sutton HillThe Point Type B1,111 Sq Ft$2,460
Woodbury GardensTwo Bedroom1,090 Sq Ft$2,200
Residences at West Hills Country Club2 Bedroom A1,078 Sq Ft$3,339
The Park At MainC1,076 Sq Ft$2,425

Cheapest Available Chester 2 Bedroom Apartments

As of November 15, 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 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 $2,217. 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
Hawkins Apartments2 Beds, 1.5 baths$1,900
Crestwood Apartments2-Bedroom$1,950
Idlewild Creek Apartments2 Bedroom 1 Bathroom$1,975
Sutton Hill ApartmentsSutton Hill Type 5$1,995
Stoneridge Manor Apartments2 Beds, 2 baths$2,000
Imperial Gardens Apartment HomesTwo Bedroom-933 sqft$2,010
Country Manor Apartments2BR/1.5BA$2,100
Stevens Manor Apartments2BR/1.0BA$2,150

Don't Settle: How to Negotiate Your Apartment Lease and Save Money

Discover the insider tips from an attorney and real estate agent on how to negotiate your next apartment lease. Find out what's on the table and what's not, so you can save money and get the best terms possible.

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

Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.

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Quick Rent Budget Calculator

How much rent can you afford?

The common "Rule of Thumb" is that rent should be no more than 30% of your income. How much is that? Enter your monthly income and click "Calculate My Budget" to find out.

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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 $2,217.

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 991 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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Apartment Common Area Rules: What Renters Need to Know

Written by: Christine Leonard, Esq.

Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.

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How to Negotiate Your Apartment Lease and Save Money

Written by: Christine Leonard, Esq.

Everything is a negotiation in real estate! 

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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.