1 Bedroom Apartments for Rent in Chestertown, MD (48 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

Exploring Rental Options: Apartments, Townhomes, and Lofts—Oh My!

Looking for the perfect rental? From apartments and condos to lofts and single family rentals, explore the unique pros and cons of each rental type to help you land in your perfect new place.

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Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags

Looking for the perfect new rental? Learn great ways to spot the perfect apartment for you, identify common red flags, and avoid rental issues and scams with these expert provided actionable tips.

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Renters Insurance 101: What It Is, What It Covers, and Why You Need It

From theft to fire to water damage, the unexpected can happen to any renter. Discover why renters insurance is one of the smartest and most affordable investments you can make as a tenant.

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The Berkleigh
$1,910 - $2,350

Total Monthly Price

Base Rent$1,916 - $2,956
Total Monthly PriceVaries
1 Bedroom Apartments Available Now

The Berkleigh

6221 Greenleigh AveBaltimore, MD 21220
Corporate Housing
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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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Stansbury Manor
1 Bedroom Apartments

Stansbury Manor

1 Alder DrMiddle River, MD 21220
  • Utilities Included

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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Magnolia Farms
1 Bedroom Apartments

Magnolia Farms

28 E Bel Air AveAberdeen, MD 21001
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Merion Village
1 Bedroom Apartments

Merion Village

904 Edgewood RdEdgewood, MD 21040
Senior Living
Showing Results 1-48, 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 $1,819. Aberdeen Proving Ground on Post Housing in the Greenway Farm neighborhood has the second largest 1 Bedroom, which is sized at 1,060 square feet and currently listed start at $1,795. 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$1,819
Aberdeen Proving Ground on Post HousingPatriot Villiage - Den1,060 Sq Ft$1,795
Harborside Village ApartmentsF3 w/ Sunroom - Phase III995 Sq Ft$1,715
Eagle Rock Apartments at BelcampA3-1x1828 Sq Ft$1,475
Arbors Greenleigh1 Bed/1 Bath-A3-Emory821 Sq Ft$1,773
The Berkleigh1 Bed/1 Bath-A3-Magothy815 Sq Ft$1,916
Enclave at Box Hill1 Bed/1 Bath-B801 Sq Ft$1,790
The PromenadeCapri785 Sq Ft$1,904
Woodsdale Apartments1 Bedroom 1 Bath with Den770 Sq Ft$1,435
The Greens Apartments and Townhomes1 Bedroom with den704 Sq Ft$1,217

Cheapest Available Chestertown and Nearby 1 Bedroom Apartments

As of September 13, 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 Model at Essex Park Apartments and Townhomes starting at $996 in the Miramar Landing - Gibson/Taylor neighborhood. The average price for all 1 Bedroom apartments in Chestertown is currently $1,585. 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
Essex Park Apartments and TownhomesOne Bedroom$996
The Greens Apartments and Townhomes1 Bedroom$1,015
Hartland Village ApartmentsOne bedroom$1,015
Kings Mill Apartments and TownhomesOne bedroom Apartment$1,065
Hyde Park ApartmentsOne Bedroom One Bath$1,112
Seneca Bay Apartment HomesOne Bedroom$1,205
Middle River Overlook1BD/1BA$1,254
Aberdeen Parke ApartmentsOne Bedroom$1,275

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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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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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 $1,585.

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 $1,819 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 0 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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Exploring Rental Options: Apartments, Townhomes, and Lofts - Oh My!

Written by: Robin Stewart

Where do you see yourself? When you think of home, sweet home, are you in a 3/2 apartment? Dreaming of a tall townhome? Maybe an industrial loft heavy on cool vibes is on your visioning board.

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Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags

Written by: Robin Stewart

Renters want to find a great apartment, the right place for them, one that checks all the boxes of location, rental cost, amenities, safety, and more.

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First Apartment Regrets: Real Renters Share What They'd Do Differently

Written by: Robin Stewart

Hindsight is 20/20. Live and Learn. With age comes wisdom. We’re familiar with all those expressions, and all of them apply to lessons first-time renters learn.

decorative image for Renters Insurance 101: What It Is, What It Covers, and Why You Need It article

Renters Insurance 101: What It Is, What It Covers, and Why You Need It

Written by: Robin Stewart

Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.