1 Bedroom Apartments for Rent in Chestertown, MD (42 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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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
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Baywood Village
1 Bedroom Apartments

Baywood Village

23160-23165 Baywood CtChestertown, 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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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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Showing Results 1-42, Page 1 of 1

Chestertown, MD Local Guide

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 $1,849. Harborside Village Apartments in the Goose Pond Estates neighborhood has the second largest 1 Bedroom, which is sized at 995 square feet and currently listed start at $1,715. 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$1,849
Harborside Village ApartmentsF3 w/ Sunroom - Phase III995 Sq Ft$1,715
Arbors Greenleigh1 Bed/1 Bath Loft-A5L-Cromwell892 Sq Ft$1,776
The Berkleigh1 Bed/1 Bath-A3-Magothy815 Sq Ft$1,811
Fox Run Apartments1 Bedroom 1 Bath Den813 Sq Ft$1,423
Seven Oaks Townhomes1 Bedroom 1 Bath806 Sq Ft$1,358
The Enclave at Box Hill1 Bed/1 Bath-B801 Sq Ft$1,967
ReNew BelcampAthens740 Sq Ft$1,609
The Greens Apartments and Townhomes1 Bedroom with den704 Sq Ft$1,148
Seneca Bay Apartment HomesOne Bedroom690 Sq Ft$1,245

Cheapest Available Chestertown and Nearby 1 Bedroom Apartments

As of December 22, 2025 the lowest priced 1 Bedroom apartment unit in Chestertown, MD is the Windsor III- 1 BR, 1 BA Model starting from $765 at Windsor Valley Apartments in the Goose Pond Estates neighborhood. The second most affordable Chestertown 1 Bedroom is the One bedroom Model at Hartland Village Apartments starting at $905 in the Hopewell Point neighborhood. The average price for all 1 Bedroom apartments in Chestertown is currently $1,552. Here is today’s list of the cheapest available 1 Bedroom options in Chestertown:

Apartment ListingModel NamePriced From
Windsor Valley ApartmentsWindsor III- 1 BR, 1 BA$765
Hartland Village ApartmentsOne bedroom$905
Kings Mill Apartments and TownhomesOne bedroom Apartment$1,004
The Greens Apartments and Townhomes1 Bedroom$1,020
The Village at Slippery Hill Senior Apartments- 62+A5 - One Bedroom$1,080
Seneca Bay Apartment HomesOne Bedroom$1,245
Annhurst (MD)One Bed One Bath S$1,270
Woodsdale Apartments1 Bedrooms 1 Bath$1,297
The WaldonMyrtle$1,350
Seven Oaks Townhomes1 Bedroom 1 Bath$1,375

Don't Settle: How to Negotiate Your Apartment Lease and Save Money

Discover the insider tips from an attorney and real estate agent on how to negotiate your next apartment lease. Find out what's on the table and what's not, so you can save money and get the best terms possible.

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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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The common "Rule of Thumb" is that rent should be no more than 30% of your income. How much is that? Enter your monthly income and click "Calculate My Budget" to find out.

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Remember the 3 Rules of Real Estate:
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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 Windsor Valley Apartments listed at $765.

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

The average rent for a 1 Bedroom Apartment in Chestertown is $1,552.

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 $1,849 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 392 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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Renting with Roommates: Realistic Expectations for Shared Lease

Written by: Christine Leonard, Esq.

Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.

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Apartment Common Area Rules: What Renters Need to Know

Written by: Christine Leonard, Esq.

Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.

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How to Negotiate Your Apartment Lease and Save Money

Written by: Christine Leonard, Esq.

Everything is a negotiation in real estate! 

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The Rental Move-In Inspection Checklist: A Guide for Renters

Written by: Trey Huguley

The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.