2 Bedroom Apartments for Rent in Chester, NY (57 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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44 High St
2 Bedroom Apartments

44 High St

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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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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Showing Results 1-50, Page 1 of 2

Chester, NY Local Guide

Largest Available Chester 2 Bedroom Apartments

The largest available 2 Bedroom apartment unit in Chester, NY is found at Southgate Middletown in the Middletown Goshen neighborhood and is 1,302 square feet priced from $2,795. Pulaski in the Glenview Hills At Florida neighborhood has the second largest 2 Bedroom, which is sized at 1,300 square feet and currently listed start at $1,900. Here is today’s list of the largest available 2 Bedroom units in Chester:

Apartment ListingModel NameSquare FootagePriced From
Southgate MiddletownB - 2B3 2nd Floor1,302 Sq Ft$2,795
Pulaski1,300 Sq Ft$1,900
Kensington ManorOriginal Construction1,150 Sq Ft$1,895
The Point at Sutton HillThe Point Type B1,111 Sq Ft$2,480
Woodbury GardensTwo Bedroom1,090 Sq Ft$2,200
The Park At MainC1,076 Sq Ft$2,425
Carriage Hill Apartments2 BR1,025 Sq Ft$2,200
Hawkins Apartments2 Beds, 1.5 baths1,000 Sq Ft$1,900
Briarwood House Apartments2 BRM1,000 Sq Ft$2,520

Cheapest Available Chester 2 Bedroom Apartments

As of January 09, 2026 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 $2,229. 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
Stoneridge Manor Apartments2 Beds, 2 baths$2,000
Sutton Hill ApartmentsSutton Hill Type 4$2,010
Imperial Gardens Apartment HomesTwo Bedroom-916 sqft$2,060
Stevens Manor Apartments2BR/1.0BA$2,150
Rockwood Gardens Apartments2 Beds, 1 bath$2,200
Woodbury GardensTwo Bedroom$2,200

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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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 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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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 $2,229.

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

Today's apartment with the most square footage in Chester is a 1,302 square feet unit starting from $2,795 at Southgate Middletown.

Expert Rental Resources

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.

Articles, How-To's, and Tips

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Renting with Roommates: Realistic Expectations for Shared Lease

Written by: Christine Leonard, Esq.

Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.

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A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment

Written by: Bob Mallory

Packing up everything you own to move is so stressful for many that ending your apartment lease can feel like a small or unimportant task. Ending your lease involves more than simply turning over your keys on the last day.

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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!