1 Bedroom Apartments for Rent in Chestertown, MD (39 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

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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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

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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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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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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Stansbury Manor
1 Bedroom Apartments

Stansbury Manor

1 Alder DrMiddle River, MD 21220
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Showing Results 1-39, Page 1 of 1

Chestertown, MD Local Guide

Chestertown 1 Bedroom Apartment Units with Current Availability by Neighborhood

Availability Confirmed As of: July 31, 2025

There are currently 1 available 1 Bedroom apartment units in Chestertown, MD neighborhoods that range in price from $1,300 to $1,300. 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 $1,898. Arbors Greenleigh in the Miramar Landing - Gibson/Taylor neighborhood has the second largest 1 Bedroom, which is sized at 920 square feet and currently listed start at $2,100. Here is today’s list of the largest available 1 Bedroom units in Chestertown:

Apartment ListingModel NameSquare FootagePriced From
Riverside1 Bedroom - C (RS2)1,098 Sq Ft$1,898
Arbors Greenleigh1 Bed/1 Bath Den-A2-Shipley920 Sq Ft$2,100
The Berkleigh1 Bed/1 Bath-A3-Magothy815 Sq Ft$1,999
Woodsdale Apartments1 Bedroom 1 Bath with Den770 Sq Ft$1,390
Fox Run Apartments1 Bedroom 1 Bath705 Sq Ft$1,377
The Greens Apartments and Townhomes1 Bedroom with den704 Sq Ft$1,148
Stansbury Manor1 Bedroom Deluxe700 Sq Ft$1,699
Seneca Bay Apartment HomesOne Bedroom690 Sq Ft$1,100
Perryman Station Senior Apartments, 62+1 bedroom657 Sq Ft$1,085
Harford Commons1 Bedroom650 Sq Ft$1,299

Cheapest Available Chestertown and Nearby 1 Bedroom Apartments

As of July 31, 2025 the lowest priced 1 Bedroom apartment unit in Chestertown, MD is the 1 Bedroom Model starting from $1,020 at The Greens Apartments and Townhomes in the Hopewell Point neighborhood. The second most affordable Chestertown 1 Bedroom is the One bedroom Apartment Model at Kings Mill Apartments and Townhomes starting at $1,038 in the Miramar Landing - Gibson/Taylor neighborhood. The average price for all 1 Bedroom apartments in Chestertown is currently $1,529. Here is today’s list of the cheapest available 1 Bedroom options in Chestertown:

Apartment ListingModel NamePriced From
The Greens Apartments and Townhomes1 Bedroom$1,020
Kings Mill Apartments and TownhomesOne bedroom Apartment$1,038
Perryman Station Senior Apartments, 62+1 bedroom$1,085
Seneca Bay Apartment HomesOne Bedroom$1,100
AnnhurstOne Bedroom One Bath$1,215
Woodsdale Apartments1 Bedrooms 1 Bath$1,309
Beacon Pointe Apartments and TownhomesA1-1BD/1BA$1,317
The WaldonMyrtle$1,350
Fox Run Apartments1 Bedroom 1 Bath$1,377

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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 Greens Apartments and Townhomes listed at $1,020.

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

The average rent for a 1 Bedroom Apartment in Chestertown is $1,529.

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 $1,898 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 560 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 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.

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The Art of the Rental Viewing: What to look for during a property tour

Written by: Marie Brown

You’ve scrolled through countless listings, walked through a blur of rentals, and finally found what feels like the one. The pictures? Fantastic. The neighborhood seems just right.