2 Bedroom Apartments for Rent in Chestertown, NY (49 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 Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro

Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.

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Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting

Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.

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property at 130 Van Dam St

130 Van Dam St

Saratoga SpringsNY12866
property at 17 Granite St

17 Granite St

Saratoga SpringsNY12866

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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Schermerhorn - Queensbury
2 Bedroom Apartments

Schermerhorn - Queensbury

44 Willowbrook RdQueensbury, NY 12804
Senior Living
  • Utilities Included

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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35-53-79 Meadow Ln
2 Bedroom Apartments

35-53-79 Meadow Ln

35 Meadow LnCastleton, VT 05735
  • 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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Alexander House
2 Bedroom Apartments

Alexander House

72 Union AveSaratoga Springs, NY 12866
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20 Grove Ave
2 Bedroom Apartments

20 Grove Ave

20 Grove AveGlens Falls, NY 12801
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Showing Results 1-49, 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 Perennial in the Downtown Saratoga Springs neighborhood and is 1,925 square feet priced from $4,309. Winner's circle has the second largest 2 Bedroom, which is sized at 1,404 square feet and currently listed start at $2,497. Here is today’s list of the largest available 2 Bedroom units in Chestertown:

Apartment ListingModel NameSquare FootagePriced From
PerennialLoft Penthouse1,925 Sq Ft$4,309
Winner's circleChurchill Downs (B09)1,404 Sq Ft$2,497
Townhomes at Woodlands EdgeCardinal1,300 Sq Ft$2,800
The Paddocks of SaratogaThe Preakness1,300 Sq Ft$2,305
Glen Street AssociatesPark Place1,200 Sq Ft$1,350
Park Place at Wilton, LLC2BR/2.0BA1,160 Sq Ft$2,100
The EllsworthB091,142 Sq Ft$2,156
The RidgeVista Townhome1,100 Sq Ft$2,495
Schermerhorn - South Glens FallsGarden 55+1,050 Sq Ft$1,500
Regency Park North2 Bedroom975 Sq Ft$1,315

Cheapest Available Chestertown and Nearby 2 Bedroom Apartments

As of September 06, 2025 the lowest priced 2 Bedroom apartment unit in Chestertown, NY is the 2 Bedroom Model starting from $1,315 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 $2,101. Here is today’s list of the cheapest available 2 Bedroom options in Chestertown:

Apartment ListingModel NamePriced From
Regency Park North2 Bedroom$1,315
Glen Street AssociatesPark Place$1,350
Whispering Pines2 Bedroom$1,370
Schermerhorn - South Glens FallsTownhome Two Bedroom One Bath$1,410
McGregor VillageTwo Bedroom$1,575
The EllsworthB04$1,631
Bridgewater ApartmentsTwo Bedroom$1,735
80 Main St2 Beds, 1 bath$1,850
Park Place at Wilton, LLC2BR/2.0BA$2,100
Winner's circleMan O'War (B03)$2,134

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

Explore Chestertown, NY Rentals by Map

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See the most popular apartments and homes in Chestertown, NY

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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 $1,315.

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

The average rent for a 2 Bedroom Apartment in Chestertown is $2,101.

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

Today's apartment with the most square footage in Chestertown is a 1,925 square feet unit starting from $4,309 at Perennial.

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

The average size for a 2 Bedroom rental in Chestertown is currently 874 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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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.

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The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro

Written by: Christine Leonard, Esq.

Hard truth. Moving is never easy. I’ve done it all – from local moves to cross-country relocations From packing to unpacking the last box, I have found moving to be an exhausting, expensive and stressful experience every time.

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Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting

Written by: Christine Leonard, Esq.

Throughout the day, think about all the times that you have to pay for something. So many of us reach automatically for a credit card or even our phone for a quick payment.

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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.