3 Bedroom Apartments for Rent in Chestertown, NY (42 Rentals)

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property at 45 Bakery Ln

45 Bakery Ln

MiddleburyVT05753
Showing Results 1-42, Page 1 of 1

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 Park Place at Wilton, LLC and is 2,289 square feet priced from $2,900. Schermerhorn - South Glens Falls has the second largest 3 Bedroom, which is sized at 1,500 square feet and currently listed start at $1,900. Here is today’s list of the largest available 3 Bedroom units in Chestertown:

Apartment ListingModel NameSquare FootagePriced From
Park Place at Wilton, LLCTH1 - 3BD/2.5BA - Den2,289 Sq Ft$2,900
Schermerhorn - South Glens FallsTownhome Three Bedroom Two Half Bath1,500 Sq Ft$1,900
Regency Park North3 Bedroom Townhouse1,496 Sq Ft$1,605
Winner's circleStreet Sense (C02)1,400 Sq Ft$2,306
The EllsworthC031,223 Sq Ft$2,120

Cheapest Available Chestertown and Nearby 3 Bedroom Apartments

As of November 01, 2025 the lowest priced 3 Bedroom apartment unit in Chestertown, NY is the 3 Bedroom Townhouse Model starting from $1,605 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 $2,315. Here is today’s list of the cheapest available 3 Bedroom options in Chestertown:

Apartment ListingModel NamePriced From
Regency Park North3 Bedroom Townhouse$1,605
Schermerhorn - South Glens FallsTownhome Three Bedroom Two Bath$1,775
The EllsworthC02$2,050
Winner's circleSea Hero (C01)$2,177
Park Place at Wilton, LLCTH1 - 3BD/2.5BA - Den$2,900

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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 $1,605.

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

The average rent for a 3 Bedroom Apartment in Chestertown is $2,315.

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

Today's apartment with the most square footage in Chestertown is a 2,289 square feet unit starting from $2,900 at Park Place at Wilton, LLC.

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

The average size for a 3 Bedroom rental in Chestertown is currently 1,436 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 Apartment Common Area Rules: What Renters Need to Know article

Apartment Common Area Rules: What Renters Need to Know

Written by: Christine Leonard, Esq.

Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.

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How to Negotiate Your Apartment Lease and Save Money

Written by: Christine Leonard, Esq.

Everything is a negotiation in real estate! 

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The Rental Move-In Inspection Checklist: A Guide for Renters

Written by: Trey Huguley

The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.

decorative image for Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between article

Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between

Written by: Christine Leonard, Esq.

For many people, obstacles can arise during the rental application process for a variety of issues.