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

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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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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Arbors Greenleigh
$1,690 - $2,100
Total Monthly Price

Total Monthly Price

Base Rent
$1,623 - $2,973
Total Monthly Price
$1,623 - $2,973
1 Bedroom Apartments Available Now

Arbors Greenleigh

11550 Crossroads CirBaltimore, MD 21220
Family Friendly
  • Verified
  • Customer Reviewed
  • 3D Tour

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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The Berkleigh
$1,915 - $2,250
Total Monthly Price

Total Monthly Price

Base Rent
$1,921 - $2,855
Total Monthly Price
$1,921 - $2,855
1 Bedroom Apartments Available Now

The Berkleigh

6221 Greenleigh AveBaltimore, MD 21220
Corporate Housing
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  • Customer Reviewed
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Enclave at Box Hill
Rent Specials
$1,807 - $1,919
Total Monthly Price

Total Monthly Price

Base Rent
$1,839 - $6,023
Total Monthly Price
Varies
1 Bedroom Apartments Available Now

Enclave at Box Hill

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

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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Merion Village
1 Bedroom Apartments

Merion Village

904 Edgewood RdEdgewood, MD 21040
Senior Living
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Stansbury Manor
1 Bedroom Apartments

Stansbury Manor

1 Alder DrMiddle River, MD 21220
  • Utilities Included

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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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. 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$1,839
Aberdeen Proving Ground on Post HousingPatriot Villiage - Den1,060 Sq Ft$1,795
Harborside Village ApartmentsF3 w/ Sunroom - Phase III995 Sq Ft$1,715
Arbors Greenleigh1 Bed/1 Bath Den-A2-Shipley920 Sq Ft$2,173
Eagle Rock Apartments at BelcampA3-1x1828 Sq Ft$1,610
The Berkleigh1 Bed/1 Bath-A3-Magothy815 Sq Ft$1,921
Seven Oaks Townhomes1 Bedroom 1 Bath806 Sq Ft$1,390
Enclave at Box Hill1 Bed 1 Bath-B1801 Sq Ft$1,868
Merion Village1 Bedroom 1 Bath787 Sq Ft$1,135
The Greens Apartments and Townhomes1 Bedroom with den704 Sq Ft$1,218

Cheapest Available Chestertown and Nearby 1 Bedroom Apartments

As of July 30, 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 $958 in the Miramar Landing - Gibson/Taylor neighborhood. The average price for all 1 Bedroom apartments in Chestertown is currently $1,604. 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$958
The Greens Apartments and Townhomes1 Bedroom$958
The Village at Slippery Hill Senior Apartments- 62+A5 - One Bedroom$1,080
Hartland Village ApartmentsOne bedroom$1,080
Hyde Park ApartmentsOne Bedroom One Bath$1,082
Merion Village1 Bedroom 1 Bath$1,135
Aberdeen Parke ApartmentsOne Bedroom$1,275
Woodsdale Apartments1 Bedrooms 1 Bath$1,307
The WaldonMyrtle$1,385

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:
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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 $1,604.

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 1,700 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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First Apartment Regrets: Real Renters Share What They'd Do Differently

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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.

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

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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.

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Apartment Occupancy Rates: Renter Attraction vs Renter Retention

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There’s a tenet in marketing about client or customer attraction and retention. Studies and data have consistently shown it costs less to keep a current customer than to attract a new one.

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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.