1 Bedroom Apartments for Rent in Chestertown, MD (46 Rentals)

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425 High St
1 Bedroom Apartments

425 High St

425 High StChestertown, MD 21620
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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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Baywood Village
1 Bedroom Apartments

Baywood Village

23160-23165 Baywood CtChestertown, MD 21620

Genius Ideas and Studio Layout Tips That Maximize Every Square Inch

Transform your studio apartment layout and maximize storage. Get proven ideas from a 20-year property expert to make any small space stylish and functional.

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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 Berkleigh
$1,940 - $2,103
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Total Monthly Price

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$1,946 - $2,956
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1 Bedroom Apartments Available Now

The Berkleigh

6221 Greenleigh AveBaltimore, MD 21220
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  • Utilities Included
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Arbors Greenleigh
$1,700 - $1,930
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$1,623 - $2,973
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1 Bedroom Apartments Available Now

Arbors Greenleigh

11550 Crossroads CirBaltimore, MD 21220
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  • Customer Reviewed
  • Utilities Included

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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Renting Smart: Lease Basics Every Renter Needs

Demystify Your Rental Lease. Learn the basics about renting, deposits, and tenant/landlord responsibilities. Rent smart and avoid surprises. | Renter University at ApartmentHomeLiving.com

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Stansbury Manor
1 Bedroom Apartments

Stansbury Manor

1 Alder DrMiddle River, MD 21220
  • Utilities Included

How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide

Finding the right apartment starts with three things: location, cost, and amenities. Get the insider perspective from a real estate professional on how to nail all three.

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Showing Results 1-46, 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 $1,839. 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
RiversideThe Chesapeake 21,098 Sq Ft$1,839
Harborside Village ApartmentsF3 w/ Sunroom - Phase III995 Sq Ft$1,715
Enclave at Box Hill1 Bed/1 Bath Loft-E935 Sq Ft$1,976
The Berkleigh1 Bed/1 Bath-A3-Magothy815 Sq Ft$1,946
Seven Oaks Townhomes1 Bedroom 1 Bath806 Sq Ft$1,436
The Promenade at Red Apple Town CenterPhase II- The Capri785 Sq Ft$2,009
Arbors Greenleigh1 Bed/1 Bath-A5-Rockland755 Sq Ft$1,723
Eagle Rock Apartments at BelcampA2-1x1751 Sq Ft$1,665
The Greens Apartments and Townhomes1 Bedroom with den704 Sq Ft$1,300
Seneca Bay Apartment HomesOne Bedroom690 Sq Ft$1,005

Cheapest Available Chestertown and Nearby 1 Bedroom Apartments

As of June 14, 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 $785 in the Miramar Landing - Gibson/Taylor neighborhood. The average price for all 1 Bedroom apartments in Chestertown is currently $1,524. 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$785
Hartland Village ApartmentsOne bedroom$885
The Greens Apartments and Townhomes1 Bedroom$925
Seneca Bay Apartment HomesOne Bedroom$1,005
Annhurst (MD)One Bed One Bath Standard$1,200
Aberdeen Parke ApartmentsOne Bedroom$1,275
Beacon Pointe Apartments and TownhomesA1-1BD/1BA$1,292
Woodsdale Apartments1 Bedrooms 1 Bath$1,303
Harford Commons1 Bedroom$1,354

Real Estate and Rental Term Glossary | ApartmentHomeLiving.com Renter University

From the letter A all the way to the letter Z, the Real Estate and Rental Term Glossary from the content team at ApartmentHomeLiving.com provides our visitors and shoppers with a little clarity and helpful guidance in navigating the real estate world through definitions and explainers for the top subjects and terms that someone may come across during the leasing, buying, or selling process.

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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:
Location, Location, Location!

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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 $1,524.

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 $1,839 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 700 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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Genius Ideas and Studio Layout Tips That Maximize Every Square Inch

Written by: Lauren Harrington

This article was written based on first-hand renter experiences and common layout challenges identified after move-in.

decorative image for How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide article

How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide

Written by: Robin Stewart

Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.

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Pet-Friendly Renting: Everything You Need to Know Before You Move

Written by: Christine Leonard, Esq.

For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.

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Creative Ways Developers Reimagine Retail Spaces as Residential Units

Written by: Robin Stewart

Adaptive reuse is when a commercial property is converted and repurposed. The real estate industry has embraced a growing number of these projects.