2 Bedroom Apartments for Rent in Chester, NY (52 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

Renting with Roommates: Realistic Expectations for Shared Lease

Sharing a lease? Learn how to set clear expectations with your roommates on routines, bills, and cleaning to ensure a successful and peaceful shared living arrangement.

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Stevens Manor Apartments
Rent Specials
$2,300
Total Monthly Price

Total Monthly Price

Base Rent
$1,900 - $2,300
Total Monthly Price
$1,900 - $2,300
2 Bedroom Apartments Available Now

Stevens Manor Apartments

644 Silver Lake Scotchtown RdMiddletown, NY 10941
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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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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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Renting Smart: Lease Basics Every Renter Needs

Demystify Your Rental Lease. Learn the basics about renting, deposits, and tenant/landlord responsibilities. Rent smart and avoid surprises. | Renter University at ApartmentHomeLiving.com

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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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Knox Village
2 Bedroom Apartments

Knox Village

835 Blooming Grove TpkeNew Windsor, NY 12553
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Crestwood Apartments
2 Bedroom Apartments

Crestwood Apartments

92 Fitzgerald DrMiddletown, NY 10940
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Golf Links Apartments
2 Bedroom Apartments

Golf Links Apartments

206 Golf Links RdMiddletown, NY 10940
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Kensington Manor
2 Bedroom Apartments

Kensington Manor

1 Kensington MnrMiddletown, NY 10941
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How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide

Finding the right apartment starts with three things: location, cost, and amenities. Get the insider perspective from a real estate professional on how to nail all three.

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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 $3,000. Sterling Parc at Middletown has the second largest 2 Bedroom, which is sized at 1,231 square feet and currently listed start at $2,788. Here is today’s list of the largest available 2 Bedroom units in Chester:

Apartment ListingModel NameSquare FootagePriced From
Southgate MiddletownB-2B3 3rd Floor1,302 Sq Ft$3,000
Sterling Parc at MiddletownRidgebury1,231 Sq Ft$2,788
The Point at Sutton HillThe Point Type B1,111 Sq Ft$2,480
The Park At MainC1,076 Sq Ft$2,650
Northwoods ApartmentsNW Unit Type A1,056 Sq Ft$2,420
Carriage Hill Apartments2 BR1,025 Sq Ft$2,225
Briarwood House Apartments2 BRM1,000 Sq Ft$2,320
Imperial Gardens Apartment HomesTwo Bedroom 1.5 Bath-990 sqft990 Sq Ft$2,165
Lamplight Village Apartments2 Bedroom 1.5 Bath Townhouse980 Sq Ft$2,400
Rockwood Gardens Apartments2 Beds, 1 bath934 Sq Ft$2,200

Cheapest Available Chester 2 Bedroom Apartments

As of June 20, 2026 the lowest priced 2 Bedroom apartment unit in Chester, NY is the 2 Beds, 2 baths Model starting from $2,000 at Stoneridge Manor Apartments in the Middletown Goshen neighborhood. The second most affordable Chester 2 Bedroom is the Two Bedroom 1.5 Bath-916 sqft Model at Imperial Gardens Apartment Homes starting at $2,110 . The average price for all 2 Bedroom apartments in Chester is currently $2,392. Here is today’s list of the cheapest available 2 Bedroom options in Chester:

Apartment ListingModel NamePriced From
Stoneridge Manor Apartments2 Beds, 2 baths$2,000
Imperial Gardens Apartment HomesTwo Bedroom 1.5 Bath-916 sqft$2,110
Rockwood Gardens Apartments2 Beds, 1 bath$2,200
Carriage Hill Apartments2 BR$2,225
Stevens Manor Apartments2BR/1.0BA$2,300
Country Manor Apartments2BR/1.5BA$2,300
Briarwood House Apartments2 BRM$2,320
Lamplight Village Apartments2 Bedroom 1.5 Bath Townhouse$2,400
Northwoods ApartmentsNW Unit Type A$2,420
The Point at Sutton HillThe Point Type A$2,420

Real Estate and Rental Term Glossary | ApartmentHomeLiving.com Renter University

From the letter A all the way to the letter Z, the Real Estate and Rental Term Glossary from the content team at ApartmentHomeLiving.com provides our visitors and shoppers with a little clarity and helpful guidance in navigating the real estate world through definitions and explainers for the top subjects and terms that someone may come across during the leasing, buying, or selling process.

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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 $2,392.

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 $3,000 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.

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