1 Bedroom Apartments for Rent in Chestertown, MD (38 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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321 Calvert St
1 Bedroom Apartments

321 Calvert St

321 Calvert StChestertown, 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

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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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 1-38, Page 1 of 1

Chestertown, MD Local Guide

Chestertown 1 Bedroom Apartment Units with Current Availability by Neighborhood

Availability Confirmed As of: May 06, 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 925 square feet and currently listed start at $2,049. 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 Den-A4-D-Long Point925 Sq Ft$2,049
Arbors Greenleigh1 Bed/1 Bath Den-A6-Parkton892 Sq Ft$1,925
Seven Oaks Townhomes1 Bedroom 1 Bath806 Sq Ft$1,367
Kent Crossing Apartments1 Bedroom786 Sq Ft$1,300
Hyde Park ApartmentsOne Bedroom One Bath732 Sq FtCall for Rates
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$1,075

Cheapest Available Chestertown and Nearby 1 Bedroom Apartments

As of May 06, 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 $1,551. 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
Seneca Bay Apartment HomesOne Bedroom$1,015
The Greens Apartments and Townhomes1 Bedroom$1,020
Hartland Village ApartmentsOne bedroom$1,038
Kings Mill Apartments and TownhomesOne bedroom Apartment$1,038
AnnhurstOne Bedroom One Bath$1,250
Harford Commons1 Bedroom$1,269
Kent Crossing Apartments1 Bedroom$1,300
Seven Oaks Townhomes1 Bedroom 1 Bath$1,367

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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 $1,551.

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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The Freedom of Short-Term Leases: Exploring the Advantages for Renters

Written by: Bobbi Jackson

If you’re looking to relocate right now, a popular solution that may best fit your current rental needs is a short-term lease.

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Navigating the Rental Market: Tips for First-Time Renters

Written by: Sandy Baker

Making the decision to rent is exciting and terrifying at the same time. For many people, there are a lot of unknowns.

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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.