2 Bedroom Apartments for Rent in Chestertown, MD (55 Rentals)

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121 Washington Ave
2 Bedroom Apartments

121 Washington Ave

121 Washington AveChestertown, MD 21620
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425 High St
2 Bedroom Apartments

425 High St

425 High StChestertown, MD 21620
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Baywood Village
2 Bedroom Apartments

Baywood Village

23160-23165 Baywood CtChestertown, MD 21620

Renting with Roommates: Realistic Expectations for Shared Lease

Sharing a lease? Learn how to set clear expectations with your roommates on routines, bills, and cleaning to ensure a successful and peaceful shared living arrangement.

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Roommate Matching: Finding the Right Fit and Avoiding Pitfalls

When searching for a roommate, follow this list of essential steps and set clear expectations to create a solid foundation for a harmonious living situation.

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The Berkleigh
$2,575 - $2,950
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$1,946 - $2,956
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2 Bedroom Apartments Available Now

The Berkleigh

6221 Greenleigh AveBaltimore, MD 21220
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Arbors Greenleigh
$2,395 - $2,775
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$1,623 - $2,973
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2 Bedroom Apartments Available Now

Arbors Greenleigh

11550 Crossroads CirBaltimore, MD 21220
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  • 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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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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Chestertown, MD Local Guide

Largest Available Chestertown and Nearby 2 Bedroom Apartments

The largest available 2 Bedroom apartment unit in Chestertown, MD is found at Enclave at Box Hill in the Harford Green neighborhood and is 1,571 square feet priced from $2,200. Harborside Village Apartments in the Goose Pond Estates neighborhood has the second largest 2 Bedroom, which is sized at 1,301 square feet and currently listed start at $2,045. Here is today’s list of the largest available 2 Bedroom units in Chestertown:

Apartment ListingModel NameSquare FootagePriced From
Enclave at Box Hill2 Bed/2 Bath Den Loft-U1,571 Sq Ft$2,200
Harborside Village ApartmentsA2 w/ Den Phase III1,301 Sq Ft$2,045
Arbors Greenleigh2 Bed/2 Bath-B3-Hayfield1,218 Sq Ft$2,573
RiversideThe Wayfarer 21,202 Sq Ft$2,099
Eagle Rock Apartments at BelcampB4-2x2D1,200 Sq Ft$1,960
Holly Oaks2 Bed 2 Bath1,128 Sq Ft$1,785
Stansbury Manor2 Bedroom Townhome1,100 Sq Ft$1,734
Aberdeen Proving Ground on Post HousingPatriot Village - Stream1,060 Sq Ft$1,795
The Berkleigh2 Bed/2 Bath-B1-Bohemia1,046 Sq Ft$2,581
Perkins PlaceThe Calvert1,000 Sq Ft$1,712

Cheapest Available Chestertown and Nearby 2 Bedroom Apartments

As of June 14, 2026 the lowest priced 2 Bedroom apartment unit in Chestertown, MD is the Windsor III- 2 BR, 1 BA Model starting from $950 at Windsor Valley Apartments in the Goose Pond Estates neighborhood. The second most affordable Chestertown 2 Bedroom is the Two bedroom Model at Hartland Village Apartments starting at $1,030 in the Hopewell Point neighborhood. The average price for all 2 Bedroom apartments in Chestertown is currently $1,759. Here is today’s list of the cheapest available 2 Bedroom options in Chestertown:

Apartment ListingModel NamePriced From
Windsor Valley ApartmentsWindsor III- 2 BR, 1 BA$950
Hartland Village ApartmentsTwo bedroom$1,030
The Greens Apartments and Townhomes2 Bedroom$1,032
Hopkins Point by OneWallTwo Bedroom$1,075
Seneca Bay Apartment HomesTwo Bedroom - 853 sqft$1,135
Magnolia Farms2 Bedroom Apt$1,190
Hyde Park ApartmentsTwo Bedroom One Bath$1,195
Middle River Overlook2BD/1BA$1,199
Kings Mill Apartments and TownhomesTwo Bedroom Apartment$1,232

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

Ranked #

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!

Explore Chestertown, MD Rentals by Map

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Frequently Asked Questions about 2 Bedroom Chestertown Apartments

What is the Cheapest apartment in Chestertown with 2 Bedroom?

Currently the most affordable 2 Bedroom in Chestertown is at Windsor Valley Apartments listed at $950.

How much is the average rent for a 2 Bedroom Chestertown Apartment?

The average rent for a 2 Bedroom Apartment in Chestertown is $1,759.

What is the largest available 2 Bedroom Chestertown Apartment for rent?

Today's apartment with the most square footage in Chestertown is a 1,571 square feet unit starting from $2,200 at Enclave at Box Hill.

What is the average size for Chestertown 2 Bedroom Apartments for rent?

The average size for a 2 Bedroom rental in Chestertown is currently 1,050 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

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.

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Neighborhood and Market Insights: How to Choose the Right Area to Rent

Written by: Robin Stewart

Apartment-hunting can be a gargantuan task. Renters have a wish list of items—some luxuries, some necessities—but finding what you seek in the right place is perhaps the most important part of the journey.