2 Bedroom Apartments for Rent in Chester, NY (50 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

Renters Insurance 101: What It Is, What It Covers, and Why You Need It

From theft to fire to water damage, the unexpected can happen to any renter. Discover why renters insurance is one of the smartest and most affordable investments you can make as a tenant.

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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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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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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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29 N Main St
2 Bedroom Apartments

29 N Main St

29 N Main StFlorida, NY 10921
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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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140 Highland Ave
2 Bedroom Apartments

140 Highland Ave

140 Highland AveMiddletown, NY 10940
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Cottage Suites
2 Bedroom Apartments

Cottage Suites

52-89 Cottage StMiddletown, NY 10940

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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Showing Results 1-50, Page 1 of 1

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 1,254 square feet priced from $2,900. Summit Terrace Luxury Apartments in the Brighton Green neighborhood has the second largest 2 Bedroom, which is sized at 1,179 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
Southgate MiddletownB-2B2 3rd Floor1,254 Sq Ft$2,900
Summit Terrace Luxury ApartmentsWestchester1,179 Sq Ft$2,500
Sterling Parc at MiddletownHampton1,125 Sq Ft$2,621
The Point at Sutton HillThe Point Type A1,088 Sq Ft$2,420
The Park At MainC1,076 Sq Ft$2,650
Crestwood Apartments2-Bedroom950 Sq Ft$2,100
Rockwood Gardens Apartments2 Beds, 1 bath934 Sq Ft$2,200
Imperial Gardens Apartment HomesTwo Bedroom-933 sqft933 Sq Ft$2,215
The North Court Apartments.Two Bed 2 Bath924 Sq Ft$3,025
Knox Village2 Bedroom900 Sq Ft$2,100

Cheapest Available Chester 2 Bedroom Apartments

As of August 05, 2026 the lowest priced 2 Bedroom apartment unit in Chester, NY is the Sutton Hill Type 4 Model starting from $1,850 at Sutton Hill Apartments in the Middletown Goshen neighborhood. The second most affordable Chester 2 Bedroom is the 1 bedroom plus den 2nd floor Model at Lamplight Village Apartments starting at $2,000 in the Estates of Briarcliff neighborhood. The average price for all 2 Bedroom apartments in Chester is currently $2,422. Here is today’s list of the cheapest available 2 Bedroom options in Chester:

Apartment ListingModel NamePriced From
Sutton Hill ApartmentsSutton Hill Type 4$1,850
Lamplight Village Apartments1 bedroom plus den 2nd floor$2,000
Stoneridge Manor Apartments2 Beds, 2 baths$2,000
Woodbury GardensTwo Bedroom$2,100
Knox Village2 Bedroom$2,100
Crestwood Apartments2-Bedroom$2,100
Rockwood Gardens Apartments2 Beds, 1 bath$2,200
Summit Terrace Luxury ApartmentsDutchess$2,200
Imperial Gardens Apartment HomesTwo Bedroom-933 sqft$2,215
Country Manor Apartments2BR/1.5BA$2,300

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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Remember the 3 Rules of Real Estate:
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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 $2,422.

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

Today's apartment with the most square footage in Chester is a 1,254 square feet unit starting from $2,900 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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First Apartment Regrets: Real Renters Share What They'd Do Differently

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How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide

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