3 Bedroom Apartments for Rent in Chestertown, NY (31 Rentals)

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property at 27 Horseshoe Dr

27 Horseshoe Dr

Saratoga SpringsNY12866
property at 40 Tom Sawyer Dr

40 Tom Sawyer Dr

GansevoortNY12831
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Chestertown, NY Local Guide

Largest Available Chestertown and Nearby 3 Bedroom Apartments

The largest available 3 Bedroom apartment unit in Chestertown, NY is found at Winners Circle and is 1,746 square feet priced from $3,220. 14 Hudson has the second largest 3 Bedroom, which is sized at 1,615 square feet and currently listed start at $2,200. Here is today’s list of the largest available 3 Bedroom units in Chestertown:

Apartment ListingModel NameSquare FootagePriced From
Winners CirclePimlico L41,746 Sq Ft$3,220
14 Hudson1,615 Sq Ft$2,200
Schermerhorn - South Glens FallsTownhome Three Bedroom Two Half Bath1,500 Sq Ft$1,900
Regency Park North3 Bedroom Townhouse1,496 Sq Ft$1,580
The EllsworthC1-A1,223 Sq Ft$2,103
Whispering Pines3 Bedroom Townhouse1,145 Sq Ft$1,855

Cheapest Available Chestertown and Nearby 3 Bedroom Apartments

As of July 23, 2025 the lowest priced 3 Bedroom apartment unit in Chestertown, NY is the 3 Bedroom Townhouse Model starting from $1,580 at Regency Park North . The second most affordable Chestertown 3 Bedroom is the Townhome Three Bedroom Two Bath Model at Schermerhorn - South Glens Falls starting at $1,775 . The average price for all 3 Bedroom apartments in Chestertown is currently $2,586. Here is today’s list of the cheapest available 3 Bedroom options in Chestertown:

Apartment ListingModel NamePriced From
Regency Park North3 Bedroom Townhouse$1,580
Schermerhorn - South Glens FallsTownhome Three Bedroom Two Bath$1,775
Whispering Pines3 Bedroom Townhouse$1,855
The EllsworthC1-A$2,103
Winners CirclePimlico L4$3,220

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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 3 Bedroom Chestertown Apartments

What is the Cheapest apartment in Chestertown with 3 Bedroom?

Currently the most affordable 3 Bedroom in Chestertown is at Regency Park North listed at $1,580.

How much is the average rent for a 3 Bedroom Chestertown Apartment?

The average rent for a 3 Bedroom Apartment in Chestertown is $2,586.

What is the largest available 3 Bedroom Chestertown Apartment for rent?

Today's apartment with the most square footage in Chestertown is a 1,746 square feet unit starting from $3,220 at Winners Circle.

What is the average size for Chestertown 3 Bedroom Apartments for rent?

The average size for a 3 Bedroom rental in Chestertown is currently 1,660 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.

decorative image for Roommate Matching: Finding the Right Fit and Avoiding Pitfalls article

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.