1 Bedroom Apartments for Rent in Chestertown, MD (37 Rentals)

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121 Washington Ave
1 Bedroom Apartments

121 Washington Ave

121 Washington AveChestertown, MD 21620
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200 N Queen St
1 Bedroom Apartments

200 N Queen St

200 N Queen StChestertown, MD 21620
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Baywood Village
1 Bedroom Apartments

Baywood Village

23160-23165 Baywood CtChestertown, MD 21620
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187 Flatland Rd
1 Bedroom Apartments

187 Flatland Rd

187 Flatland RdChestertown, MD 21620
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425 High St
1 Bedroom Apartments

425 High St

425 High StChestertown, MD 21620
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321 Calvert St
1 Bedroom Apartments

321 Calvert St

321 Calvert StChestertown, MD 21620

Know Your Rights - How Discrimination Laws Impact Landlords and Tenants

Read our practical guide to landlord and tenant rights. Understand protected classes, reasonable accommodations, and legal exceptions to prevent housing discrimination.

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Stansbury Manor
1 Bedroom Apartments

Stansbury Manor

1 Alder DrMiddle River, MD 21220
  • Utilities Included
Showing Results 1-37, Page 1 of 1

Chestertown, MD Local Guide

Chestertown 1 Bedroom Apartment Units with Current Availability by Neighborhood

Availability Confirmed As of: April 27, 2025

There are currently 1 available 1 Bedroom apartment units in Chestertown, MD neighborhoods that range in price from $1,300 to $1,400. Heres is today's list of the top neighborhoods in Chestertown with the most available 1 Bedroom apartments:

NeighborhoodAvailable UnitsMedian PriceMin Price
Coventry Farms1$1,300$1,300

Largest Available Chestertown and Nearby 1 Bedroom Apartments

The largest available 1 Bedroom apartment unit in Chestertown, MD is found at Riverside in the Holly Woods - Woodfield/Wyngate neighborhood and is 1,098 square feet priced from $1,779. The Berkleigh in the Miramar Landing - Gibson/Taylor neighborhood has the second largest 1 Bedroom, which is sized at 815 square feet and currently listed start at $1,899. Here is today’s list of the largest available 1 Bedroom units in Chestertown:

Apartment ListingModel NameSquare FootagePriced From
Riverside1 Bedroom - C1,098 Sq Ft$1,779
The Berkleigh1 Bed/1 Bath-A3-Magothy815 Sq Ft$1,899
Seven Oaks Townhomes1 Bedroom 1 Bath806 Sq Ft$1,356
Kent Crossing Apartments1 Bedroom786 Sq Ft$1,300
Arbors Greenleigh1 Bed/1 Bath-A5-Rockland755 Sq Ft$1,650
ReNew BelcampAlexandria751 Sq Ft$1,545
The Village at Slippery Hill IIA1 - One Bedroom Apartment723 Sq Ft$585
Fox Run Apartments1 Bedroom 1 Bath705 Sq Ft$1,377
The Greens Apartments and Townhomes1 Bedroom with den704 Sq Ft$1,148
Seneca Bay Apartment HomesOne Bedroom690 Sq Ft$1,070

Cheapest Available Chestertown and Nearby 1 Bedroom Apartments

As of April 27, 2025 the lowest priced 1 Bedroom apartment unit in Chestertown, MD is the A1 - One Bedroom Apartment Model starting from $585 at The Village at Slippery Hill II . The second most affordable Chestertown 1 Bedroom is the 1 Bed, 1 bath Model at Center Park Apartments starting at $770 in the North Brook neighborhood. The average price for all 1 Bedroom apartments in Chestertown is currently $1,548. Here is today’s list of the cheapest available 1 Bedroom options in Chestertown:

Apartment ListingModel NamePriced From
The Village at Slippery Hill IIA1 - One Bedroom Apartment$585
Center Park Apartments1 Bed, 1 bath$770
Hartland Village ApartmentsOne bedroom$939
Seneca Bay Apartment HomesOne Bedroom$1,010
The Greens Apartments and Townhomes1 Bedroom$1,020
Kings Mill Apartments and TownhomesOne bedroom Apartment$1,038
Harford Commons1 Bedroom$1,284
Kent Crossing Apartments1 Bedroom$1,300
The WaldonMyrtle$1,350
Seven Oaks Townhomes1 Bedroom 1 Bath$1,356

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Getting Around Chestertown, MD

Walk Score®

47 / 100

Car-Dependent

Most errands require a car

Bike Score®

55 / 100

Bikeable

Some 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 1 Bedroom Chestertown Apartments

What is the Cheapest apartment in Chestertown with 1 Bedroom?

Currently the most affordable 1 Bedroom in Chestertown is at The Village at Slippery Hill II listed at $585.

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

The average rent for a 1 Bedroom Apartment in Chestertown is $1,548.

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

Today's apartment with the most square footage in Chestertown is a 1,098 square feet unit starting from $1,779 at Riverside.

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

The average size for a 1 Bedroom rental in Chestertown is currently 1,000 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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Rise of Digital Nomads: Remote Work Tips for Apartment Renters

Written by: Brandie Parton

As a digital nomad, you no longer call a set address or office building your home for eight hours of the day or more.

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Know Your Rights - How Discrimination Laws Impact Landlords and Tenants

Written by: Christine Leonard, Esq.

Everyone needs a place to live and to call home. For decades, the federal government has established protections to ensure that individuals and families can find housing free from discriminatory barriers.

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Renting Smart: Lease Basics Every Renter Needs

Written by: Christine Leonard, Esq.

Often, in the excitement of finding a new place to live, there’s a rush to make it happen, and - too often - a new tenant signs a lease without reading it carefully.

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Battling the Butts: Your Guide to the Reality of Smoke-Free Renting

Written by: Andrea Lee Negroni, JD

While many apartment buildings are “no smoking” properties, it’s hard to know exactly how many. In 2017, the National Apartment Association reported more than half of rental properties had smoke free policies.