1 Bedroom Apartments for Rent in Chestertown, NY (47 Rentals)

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Exploring Rental Options: Apartments, Townhomes, and Lofts—Oh My!

Looking for the perfect rental? From apartments and condos to lofts and single family rentals, explore the unique pros and cons of each rental type to help you land in your perfect new place.

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Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags

Looking for the perfect new rental? Learn great ways to spot the perfect apartment for you, identify common red flags, and avoid rental issues and scams with these expert provided actionable tips.

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Renters Insurance 101: What It Is, What It Covers, and Why You Need It

From theft to fire to water damage, the unexpected can happen to any renter. Discover why renters insurance is one of the smartest and most affordable investments you can make as a tenant.

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property at 20.5 Lexington Ave
$850
1 Bedroom, 1 Bath Home for Rent
Available Now

20.5 Lexington Ave

GloversvilleNY12078
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Williamsburg Court
1 Bedroom Apartments

Williamsburg Court

150 Lincoln AveSaratoga Springs, NY 12866
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80 Main St
1 Bedroom Apartments

80 Main St

80 Main StQueensbury, NY 12804
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13 Church St
1 Bedroom Apartments

13 Church St

13 Church StRutland, VT 05701
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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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20 Grove Ave
1 Bedroom Apartments

20 Grove Ave

20 Grove AveGlens Falls, NY 12801
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14 Bowman St
1 Bedroom Apartments

14 Bowman St

14 Bowman StSaratoga Springs, NY 12866
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23 Washington St
1 Bedroom Apartments

23 Washington St

23 Washington StRutland, VT 05701
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Schermerhorn - Queensbury
1 Bedroom Apartments

Schermerhorn - Queensbury

44 Willowbrook RdQueensbury, NY 12804
Corporate Housing
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Alexander House
1 Bedroom Apartments

Alexander House

72 Union AveSaratoga Springs, NY 12866
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246 West Ave
1 Bedroom Apartments

246 West Ave

246 West AveSaratoga Springs, NY 12866
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8 Phila St
1 Bedroom Apartments

8 Phila St

8 Phila StSaratoga Springs, NY 12866
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464 Maple Ave
1 Bedroom Apartments

464 Maple Ave

464 Maple AveSaratoga Springs, NY 12866
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Otterside Apartments
1 Bedroom Apartments

Otterside Apartments

39 Otterside Ct NMiddlebury, VT 05753
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Genius Ideas and Studio Layout Tips That Maximize Every Square Inch

Transform your studio apartment layout and maximize storage. Get proven ideas from a 20-year property expert to make any small space stylish and functional.

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Showing Results 1-47, Page 1 of 1

Chestertown, NY Local Guide

Largest Available Chestertown and Nearby 1 Bedroom Apartments

The largest available 1 Bedroom apartment unit in Chestertown, NY is found at The Landings at Kingsbury in the Washington County neighborhood and is 1,199 square feet priced from $1,300. The Hamlet at Saratoga Springs in the Saratoga Springs neighborhood has the second largest 1 Bedroom, which is sized at 1,010 square feet and currently listed start at $2,543. Here is today’s list of the largest available 1 Bedroom units in Chestertown:

Apartment ListingModel NameSquare FootagePriced From
The Landings at KingsburyF1,199 Sq Ft$1,300
The Hamlet at Saratoga SpringsForego1,010 Sq Ft$2,543
Carlton Hollow Senior ApartmentsOne Bedroom990 Sq Ft$2,205
The Paddocks of SaratogaThe Whitney895 Sq Ft$1,930
The GroveA1-5 | 1 Bed/ 1 Bath860 Sq Ft$2,302
14 Hudson Apartments1BR/1.0BA845 Sq Ft$1,575
The Springs1 Bedroom | NA3 | Corner825 Sq Ft$1,900
Bridgewater ApartmentsOne Bedroom825 Sq Ft$1,675
Winner's circleBirdstone (A06)821 Sq Ft$1,871
Whispering Pines1 Bedroom with Den644 Sq Ft$1,310

Cheapest Available Chestertown and Nearby 1 Bedroom Apartments

As of September 18, 2026 the lowest priced 1 Bedroom apartment unit in Chestertown, NY is the A1 Model starting from $1,004 at Reserve at Saratoga Springs in the Saratoga Springs neighborhood. The second most affordable Chestertown 1 Bedroom is the B1 Model at The Landings at Kingsbury starting at $1,050 in the Washington County neighborhood. The average price for all 1 Bedroom apartments in Chestertown is currently $1,821. Here is today’s list of the cheapest available 1 Bedroom options in Chestertown:

Apartment ListingModel NamePriced From
Reserve at Saratoga SpringsA1$1,004
The Landings at KingsburyB1$1,050
Whispering Pines1 Bedroom (Section B)$1,230
Skidmore Apartments1 Bedroom$1,560
14 Hudson Apartments1BR/1.0BA$1,575
Winner's circleAlydar (A01)$1,637
Bridgewater ApartmentsOne Bedroom$1,675
The EllsworthA01$1,744
Saratoga Garden Apartments1 Bedroom$1,780
The Springs1 Bedroom | NA1$1,815

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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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!

Explore Chestertown, NY Rentals by Map

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See the most popular apartments and homes in Chestertown, NY

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Frequently Asked Questions about 1 Bedroom Chestertown Apartments

How much is the average rent for a 1 Bedroom Chestertown Apartment?

The average rent for a 1 Bedroom Apartment in Chestertown is $1,821.

What is the largest available 1 Bedroom Chestertown Apartment for rent?

Today's apartment with the most square footage in Chestertown is a 1,199 square feet unit starting from $1,300 at The Landings at Kingsbury.

What is the average size for Chestertown 1 Bedroom Apartments for rent?

The average size for a 1 Bedroom rental in Chestertown is currently 0 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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Exploring Rental Options: Apartments, Townhomes, and Lofts - Oh My!

Written by: Robin Stewart

Where do you see yourself? When you think of home, sweet home, are you in a 3/2 apartment? Dreaming of a tall townhome? Maybe an industrial loft heavy on cool vibes is on your visioning board.

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How Commercial-to-Residential Property Conversions Help the Housing Crisis

Written by: Robin Stewart

Many housing markets throughout America share a common complaint: a lack of affordable rental properties.

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Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags

Written by: Robin Stewart

Renters want to find a great apartment, the right place for them, one that checks all the boxes of location, rental cost, amenities, safety, and more.

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First Apartment Regrets: Real Renters Share What They'd Do Differently

Written by: Robin Stewart

Hindsight is 20/20. Live and Learn. With age comes wisdom. We’re familiar with all those expressions, and all of them apply to lessons first-time renters learn.