2 Bedroom Apartments for Rent in Chester, NY (57 Rentals)

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property at 3917 Whispering Hills Dr

$2,400

Total Monthly Price

Total Monthly Price

Base Rent
$2,400
Total Monthly Price
$2,400

2 Bedroom, 2 Bath Condo for Rent

Available Now

3917 Whispering Hills Dr

ChesterNY10918
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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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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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29 N Main St
2 Bedroom Apartments

29 N Main St

29 N Main StFlorida, NY 10921
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 $2,800. Summit Terrace Luxury Apartments in the Brighton Green neighborhood has the second largest 2 Bedroom, which is sized at 1,297 square feet and currently listed start at $2,600. 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$2,800
Summit Terrace Luxury Apartmentsorange1,297 Sq Ft$2,600
Sterling Parc at MiddletownRidgebury1,231 Sq Ft$2,646
Kensington ManorOriginal Construction1,150 Sq Ft$1,950
Residences at West Hills Country Club2 Bedroom E1,134 Sq Ft$3,544
The Park At MainC1,076 Sq Ft$2,650
Carriage Hill Apartments2 BR1,025 Sq Ft$2,200
Briarwood House Apartments2 BRM1,000 Sq Ft$2,320
Idlewild Creek Apartments2 Bedroom 2 Bathroom993 Sq Ft$2,252
Imperial Gardens Apartment HomesTwo Bedroom 1.5 Bath-990 sqft990 Sq Ft$2,170

Cheapest Available Chester 2 Bedroom Apartments

As of March 14, 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 $1,950 in the Presidential Heights neighborhood. The average price for all 2 Bedroom apartments in Chester is currently $2,343. 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$1,950
Stoneridge Manor Apartments2 Beds, 2 baths$2,000
Sutton Hill ApartmentsSutton Hill Type 7$2,015
Crestwood Apartments2-Bedroom$2,025
Imperial Gardens Apartment HomesTwo Bedroom-933 sqft$2,125
Idlewild Creek Apartments2 Bedroom 1 Bathroom$2,141
Rockwood Gardens Apartments2 Beds, 1 bath$2,200
Carriage Hill Apartments2 BR$2,200
Country Manor Apartments2BR/1.5BA$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

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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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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 $2,343.

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 $2,800 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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Maximizing Your Refund: Essential Tax Tips for Renters

Written by: Christine Leonard, Esq.

Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.

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18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property

Written by: Lauren Harrington

Renting your next home can feel thrilling and overwhelming at the same time.

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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.