2 Bedroom Apartments for Rent in Chestertown, NY (48 Rentals)

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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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property at 128 Henry St

128 Henry St

Saratoga SpringsNY12866
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Schermerhorn - Queensbury
2 Bedroom Apartments

Schermerhorn - Queensbury

44 Willowbrook RdQueensbury, NY 12804
Senior Living
  • Utilities Included
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38 West
2 Bedroom Apartments

38 West

38 West StFair Haven, VT 05743
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45 State Route 9P
2 Bedroom Apartments

45 State Route 9P

45 New York 9PBallston Spa, NY 12020
  • Utilities Included
  • Smoke Free
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486 Garrett Rd
2 Bedroom Apartments

486 Garrett Rd

486 Garrett RdBallston Spa, NY 12020
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Alexander House
2 Bedroom Apartments

Alexander House

72 Union AveSaratoga Springs, NY 12866
  • Utilities Included
Showing Results 1-48, Page 1 of 1

Chestertown, NY Local Guide

Largest Available Chestertown and Nearby 2 Bedroom Apartments

The largest available 2 Bedroom apartment unit in Chestertown, NY is found at Winners Circle and is 1,404 square feet priced from $2,521. 14 Hudson has the second largest 2 Bedroom, which is sized at 1,395 square feet and currently listed start at $1,975. Here is today’s list of the largest available 2 Bedroom units in Chestertown:

Apartment ListingModel NameSquare FootagePriced From
Winners CircleChurchill Downs L41,404 Sq Ft$2,521
14 Hudson1,395 Sq Ft$1,975
Glen Street AssociatesWarren St. Square1,335 Sq Ft$1,775
The Paddocks of SaratogaThe Preakness1,300 Sq Ft$2,305
Townhomes at Woodlands EdgeCardinal1,300 Sq Ft$2,800
Carlton Hollow Senior ApartmentsTwo Bedroom Two Bath1,241 Sq Ft$2,295
Park Place at Wilton, LLC2BD/2BA - (W)1,160 Sq Ft$2,100
The EllsworthB41,089 Sq Ft$1,848
Schermerhorn - South Glens FallsGarden 55+1,050 Sq Ft$1,500
Regency Park North2 Bedroom975 Sq Ft$1,295

Cheapest Available Chestertown and Nearby 2 Bedroom Apartments

As of July 21, 2025 the lowest priced 2 Bedroom apartment unit in Chestertown, NY is the 2 Bedroom Model starting from $1,295 at Regency Park North . The second most affordable Chestertown 2 Bedroom is the Park Place Model at Glen Street Associates starting at $1,350 . The average price for all 2 Bedroom apartments in Chestertown is currently $2,169. Here is today’s list of the cheapest available 2 Bedroom options in Chestertown:

Apartment ListingModel NamePriced From
Regency Park North2 Bedroom$1,295
Glen Street AssociatesPark Place$1,350
Whispering Pines2 Bedroom$1,370
Schermerhorn - South Glens FallsTownhome Two Bedroom One Bath$1,410
Bridgewater ApartmentsTwo Bedroom$1,425
35-53-79 Meadow Ln2 br / 1 ba$1,450
The EllsworthB1$1,573
80 Main St2 Beds, 1 bath$1,850
Park Place at Wilton, LLC2BD/2BA - (W)$2,100
Winners CircleColonel John L4$2,178

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Remember the 3 Rules of Real Estate:
Location, Location, Location!

Explore Chestertown, NY Rentals by Map

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Getting Around Chestertown, NY

Walk Score®

15 / 100

Car-Dependent

Almost all errands require a car

Bike Score®

23 / 100

Somewhat Bikeable

Minimal bike infrastructure

What Are Walk Score®, Transit Score®, and Bike Score® Ratings?

  • Walk Score® measures the walkability of any address.
  • Transit Score® measures access to public transit.
  • Bike Score® measures the bikeability of any address.

Frequently Asked Questions about 2 Bedroom Chestertown Apartments

What is the Cheapest apartment in Chestertown with 2 Bedroom?

Currently the most affordable 2 Bedroom in Chestertown is at Regency Park North listed at $1,295.

How much is the average rent for a 2 Bedroom Chestertown Apartment?

The average rent for a 2 Bedroom Apartment in Chestertown is $2,169.

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

Today's apartment with the most square footage in Chestertown is a 1,404 square feet unit starting from $2,521 at Winners Circle.

What is the average size for Chestertown 2 Bedroom Apartments for rent?

The average size for a 2 Bedroom rental in Chestertown is currently 1,005 sq ft.

Expert Rental Resources

Helpful Apartment Articles, How-To's and Tips

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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Roommate Matching: Finding the Right Fit and Avoiding Pitfalls

Written by: Cheryl Bowman

A fantastic way to save money and enjoy a built-in community is to share an apartment. However, a bad roommate situation can turn your dream rental into a nightmare.

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The Art of the Rental Viewing: What to look for during a property tour

Written by: Marie Brown

You’ve scrolled through countless listings, walked through a blur of rentals, and finally found what feels like the one. The pictures? Fantastic. The neighborhood seems just right.

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Know Your Budget: Calculating What You Can Realistically Afford When Renting

Written by: Lauren Harrington

Renting an apartment or house isn’t just about looking through online ads, choosing a few apartments or homes you want to tour, filling out an application, and putting down a deposit. Those things are all necessary and important.

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The Freedom of Short-Term Leases: Exploring the Advantages for Renters

Written by: Bobbi Jackson

If you’re looking to relocate right now, a popular solution that may best fit your current rental needs is a short-term lease.