2 Bedroom Apartments for Rent in Chestertown, NY (67 Rentals)

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Renting with Roommates: Realistic Expectations for Shared Lease

Sharing a lease? Learn how to set clear expectations with your roommates on routines, bills, and cleaning to ensure a successful and peaceful shared living arrangement.

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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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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 93 Curtis Ln

$2,100

2 Bedroom, 2 Bath Home for Rent

Available Now

93 Curtis Ln

Fort EdwardNY12828

Renting Smart: Lease Basics Every Renter Needs

Demystify Your Rental Lease. Learn the basics about renting, deposits, and tenant/landlord responsibilities. Rent smart and avoid surprises. | Renter University at ApartmentHomeLiving.com

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38 West St
2 Bedroom Apartments

38 West St

38 West StFair Haven, VT 05743

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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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 The Paddocks of Saratoga and is 1,454 square feet priced from $2,505. Park Place Wilton has the second largest 2 Bedroom, which is sized at 1,447 square feet and currently listed start at $2,250. Here is today’s list of the largest available 2 Bedroom units in Chestertown:

Apartment ListingModel NameSquare FootagePriced From
The Paddocks of SaratogaThe Travers1,454 Sq Ft$2,505
Park Place Wilton2BD/2BA - Den1,447 Sq Ft$2,250
Townhomes at Woodlands EdgeCardinal1,300 Sq Ft$2,900
Carlton Hollow Senior ApartmentsTwo Bedroom Two Bath1,241 Sq Ft$2,485
The Landings at KingsburyE1,228 Sq Ft$1,300
Perennial2 Bedroom1,226 Sq Ft$3,075
Steeplechase At MaltaB6 Renovated -- Attached Garage1,201 Sq Ft$2,550
The RidgeVista Townhome1,100 Sq Ft$2,625
The Springs2 Bedroom | BT3-Renovated | 1st Floor Townhouse1,072 Sq Ft$3,051
South Glens FallsGarden 55+1,050 Sq Ft$1,500

Cheapest Available Chestertown and Nearby 2 Bedroom Apartments

As of June 11, 2026 the lowest priced 2 Bedroom apartment unit in Chestertown, NY is the E Model starting from $1,300 at The Landings at Kingsbury . The second most affordable Chestertown 2 Bedroom is the Townhome Two Bedroom One Bath Model at South Glens Falls starting at $1,410 . The average price for all 2 Bedroom apartments in Chestertown is currently $2,351. Here is today’s list of the cheapest available 2 Bedroom options in Chestertown:

Apartment ListingModel NamePriced From
The Landings at KingsburyE$1,300
South Glens FallsTownhome Two Bedroom One Bath$1,410
Whispering Pines2 Bedroom$1,430
McGregor Village2 Beds/1 Bath + Balcony & W/D$1,595
Park Place Wilton2BD/2BA - Den$2,250
Springwood Meadows Townhome Apartments2 Bedroom Townhome with Basement$2,300
The Paddocks of SaratogaThe Preakness$2,355
Carlton Hollow Senior ApartmentsTwo Bedroom One Bath$2,355
Steeplechase At MaltaB6 Renovated -- Attached Garage$2,550
The RidgeVista Townhome$2,625

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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Pet Friendly Lifestyle

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Among cities in New York for Apartment listings with Pet Friendly Amenities.

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

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Frequently Asked Questions about 2 Bedroom Chestertown Apartments

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

The average rent for a 2 Bedroom Apartment in Chestertown is $2,351.

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

Today's apartment with the most square footage in Chestertown is a 1,454 square feet unit starting from $2,505 at The Paddocks of Saratoga.

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

The average size for a 2 Bedroom rental in Chestertown is currently 1,214 sq ft.

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.

Articles, How-To's, and Tips

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How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide

Written by: Robin Stewart

Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.

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Pet-Friendly Renting: Everything You Need to Know Before You Move

Written by: Christine Leonard, Esq.

For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.

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Creative Ways Developers Reimagine Retail Spaces as Residential Units

Written by: Robin Stewart

Adaptive reuse is when a commercial property is converted and repurposed. The real estate industry has embraced a growing number of these projects.

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Neighborhood and Market Insights: How to Choose the Right Area to Rent

Written by: Robin Stewart

Apartment-hunting can be a gargantuan task. Renters have a wish list of items—some luxuries, some necessities—but finding what you seek in the right place is perhaps the most important part of the journey.