2 Bedroom Apartments for Rent in Chester, NY (52 Rentals)

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property at 82 High St
$2,300

Total Monthly Price

Base Rent$2,300
Total Monthly Price$2,300
2 Bedroom, 1 Bath Condo for Rent
Available Now

82 High St, Unit 5

82 High St
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
  • Utilities Included
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Country Manor Apartments
Rent Specials
$2,200 - $2,300

Total Monthly Price

Base Rent$1,875 - $2,300
Total Monthly Price$1,875 - $2,300
2 Bedroom Apartments Available Now

Country Manor Apartments

700 Stratford LnMiddletown, NY 10940
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  • Utilities Included

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property at 315 Bellvale Lakes Rd
$2,400

Total Monthly Price

Base Rent$2,400
Total Monthly Price$2,400
2 Bedroom, 1 Bath Home for Rent
Available Oct 15
Cost Per Sq.Ft.

315 Bellvale Lakes Rd

WarwickNY10990

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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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
  • Utilities Included
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Kensington Manor
2 Bedroom Apartments

Kensington Manor

1 Kensington MnrMiddletown, NY 10941
  • Utilities Included

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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 1,254 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 2nd Floor1,254 Sq Ft$2,900
Summit Terrace Luxury ApartmentsWestchester1,179 Sq Ft$2,500
Residences at West Hills Country Club2 Bedroom E11,134 Sq Ft$3,453
Sterling Parc at MiddletownHampton1,125 Sq Ft$2,473
The Park At MainC1,076 Sq Ft$2,650
Sherwood Forest Garden Apartments2x11,010 Sq Ft$2,250
Boulder Pointe Apartments2 Bedrooms | 2 Bathrooms954 Sq Ft$2,482
Crestwood Apartments2-Bedroom950 Sq Ft$2,100
Rockwood Gardens Apartments2 Beds, 1 bath934 Sq Ft$2,200
Knox Village2 Bedroom900 Sq Ft$2,100

Cheapest Available Chester 2 Bedroom Apartments

As of September 21, 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 Sutton Hill Type 5 Model at Sutton Hill Apartments starting at $2,015 . The average price for all 2 Bedroom apartments in Chester is currently $2,371. 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
Sutton Hill ApartmentsSutton Hill Type 5$2,015
Crestwood Apartments2-Bedroom$2,100
Knox Village2 Bedroom$2,100
Harriman Woods Apartments2 bedroom 1st floor$2,150
Imperial Gardens Apartment HomesTwo Bedroom 1.5 Bath-916 sqft$2,165
Summit Terrace Luxury ApartmentsDutchess$2,200
Rockwood Gardens Apartments2 Beds, 1 bath$2,200
Country Manor Apartments2BR/1.5BA$2,200
Sherwood Forest Garden Apartments2x1$2,250

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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 $2,371.

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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