1 Bedroom Apartments for Rent in Chestertown, MD (44 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

Expert Solutions for Creating the Perfect Work-From-Home Apartment Layouts

Create a productive work-from-home apartment setup, even in a small space or studio. Discover layout ideas, desk solutions, and organization tips that actually work.

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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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The Berkleigh
$1,950 - $2,264
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Total Monthly Price

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$1,656 - $3,106
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1 Bedroom Apartments Available Now

The Berkleigh

6221 Greenleigh AveBaltimore, MD 21220
Corporate Housing
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  • Customer Reviewed
  • Utilities Included
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Arbors Greenleigh
$1,700 - $1,945
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Total Monthly Price

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$1,623 - $3,128
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1 Bedroom Apartments Available May 22

Arbors Greenleigh

11550 Crossroads CirBaltimore, MD 21220
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  • Utilities Included

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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Enclave at Box Hill
Rent Specials
$1,766 - $1,981
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Total Monthly Price

Base Rent
$1,710 - $4,287
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1 Bedroom Apartments Available Now

Enclave at Box Hill

3405 McCurley DrAbingdon, MD 21009
Corporate Housing
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  • Customer Reviewed
  • 3D Tour

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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Stansbury Manor
1 Bedroom Apartments

Stansbury Manor

1 Alder DrMiddle River, MD 21220
  • Utilities Included
Showing Results 1-44, 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 $1,809. Harborside Village Apartments in the Goose Pond Estates neighborhood has the second largest 1 Bedroom, which is sized at 1,081 square feet and currently listed start at $1,815. Here is today’s list of the largest available 1 Bedroom units in Chestertown:

Apartment ListingModel NameSquare FootagePriced From
RiversideThe Chesapeake 21,098 Sq Ft$1,809
Harborside Village ApartmentsE1 w/ Garage Phase III1,081 Sq Ft$1,815
The Berkleigh1 Bed/1 Bath-A3-Magothy815 Sq Ft$1,956
Enclave at Box Hill1 Bed 1 Bath-B1801 Sq Ft$1,740
Chesapeake Village Apartments1 Bedroom, 1 Bath, Den750 Sq Ft$1,297
Harford Commons1 Bedroom Townhome750 Sq Ft$1,429
ReNew BelcampAthens740 Sq Ft$1,589
Hyde Park ApartmentsOne Bedroom One Bath732 Sq Ft$1,109
The Greens Apartments and Townhomes1 Bedroom with den704 Sq Ft$1,171
Seneca Bay Apartment HomesOne Bedroom690 Sq Ft$1,055

Cheapest Available Chestertown and Nearby 1 Bedroom Apartments

As of April 28, 2026 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 Apartment Model at Kings Mill Apartments and Townhomes starting at $835 in the Miramar Landing - Gibson/Taylor neighborhood. The average price for all 1 Bedroom apartments in Chestertown is currently $1,491. 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
Kings Mill Apartments and TownhomesOne bedroom Apartment$835
The Greens Apartments and Townhomes1 Bedroom$868
The Village at Slippery Hill Senior Apartments- 62+A3 - One Bedroom$975
Hartland Village ApartmentsOne bedroom$985
Seneca Bay Apartment HomesOne Bedroom$1,055
Hyde Park ApartmentsOne Bedroom One Bath$1,109
Chesapeake Village Apartments1 Bedroom, 1 Bath$1,247
Aberdeen Parke ApartmentsOne Bedroom$1,275
Woodsdale Apartments1 Bedrooms 1 Bath$1,295

10 Hidden Costs of Renting You Should Budget for Before Signing a Lease

Avoid financial stress when renting. Learn about the 10 most common hidden costs—from pet fees to utilities—you must budget for before you sign a lease.

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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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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 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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Pet Friendly Lifestyle

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Among cities in Maryland for Apartment listings with Pet Friendly Amenities.

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Remember the 3 Rules of Real Estate:
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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 $1,491.

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 $1,809 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 775 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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Expert Solutions for Creating the Perfect Work-From-Home Apartment Layouts

Written by: Lauren Harrington

This article is based on first-hand experience managing apartment communities and helping renters adapt to their spaces after moving in.

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What Does “Rent Burdened” Mean? How Much Rent Is Too Much

Written by: Lauren Harrington

This article draws from first-hand renter experiences and recurring financial challenges reported after moving in.

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Maximizing Your Refund: Essential Tax Tips for Renters

Written by: Christine Leonard, Esq.

Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.

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18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property

Written by: Lauren Harrington

Renting your next home can feel thrilling and overwhelming at the same time.