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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104 Maple Ave
2 Bedroom Apartments

104 Maple Ave

104 Maple AveChestertown, MD 21620
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Baywood Village
2 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
$2,410 - $2,500
Total Monthly Price

Total Monthly Price

Base Rent
$1,623 - $2,973
Total Monthly Price
$1,623 - $2,973
2 Bedroom Apartments Available Aug 26

Arbors Greenleigh

11550 Crossroads CirBaltimore, MD 21220
Family Friendly
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The Berkleigh
$2,849
Total Monthly Price

Total Monthly Price

Base Rent
$1,921 - $2,855
Total Monthly Price
$1,921 - $2,855
2 Bedroom Apartments Available Sep 26

The Berkleigh

6221 Greenleigh AveBaltimore, MD 21220
Corporate Housing
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  • 3D Tour

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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Enclave at Box Hill
Rent Specials
$1,879 - $2,053
Total Monthly Price

Total Monthly Price

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

Enclave at Box Hill

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

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 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 1-50, Page 1 of 2

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 Harborside Village Apartments in the Goose Pond Estates neighborhood and is 1,377 square feet priced from $2,120. Riverside in the Holly Woods - Woodfield/Wyngate neighborhood has the second largest 2 Bedroom, which is sized at 1,313 square feet and currently listed start at $2,208. Here is today’s list of the largest available 2 Bedroom units in Chestertown:

Apartment ListingModel NameSquare FootagePriced From
Harborside Village ApartmentsA3 w/ Den Phase III1,377 Sq Ft$2,120
RiversideThe Driftwood 21,313 Sq Ft$2,208
Enclave at Box Hill2 Bed/2 Bath Den-N41,255 Sq Ft$2,051
Eagle Rock Apartments at BelcampB4-2x2D1,200 Sq Ft$1,975
Holly Oaks2 Bed 2 Bath1,128 Sq Ft$1,785
Aberdeen Proving Ground on Post HousingPatriot Village - Stream1,060 Sq Ft$1,895
The PromenadeSorrento1,045 Sq Ft$2,179
Perkins PlaceThe Calvert1,000 Sq Ft$1,712
Seven Oaks Townhomes2 Bedrooms 1.5 Bath968 Sq Ft$1,540
Hyde Park ApartmentsTwo Bedroom One Bath967 Sq Ft$1,184

Cheapest Available Chestertown and Nearby 2 Bedroom Apartments

As of July 30, 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 Hopkins Point by OneWall starting at $1,075 in the Middle River Baltimore Crossroads neighborhood. The average price for all 2 Bedroom apartments in Chestertown is currently $1,678. 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
Hopkins Point by OneWallTwo Bedroom$1,075
Kings Mill Apartments and TownhomesTwo Bedroom Apartment$1,132
The Greens Apartments and Townhomes2 Bedroom$1,132
Middle River Overlook2BD/1BA$1,135
Hartland Village ApartmentsTwo bedroom$1,166
Hyde Park ApartmentsTwo Bedroom One Bath$1,184
Magnolia Farms2 Bedroom Apt$1,190
Seneca Bay Apartment HomesTwo Bedroom - 806 sqft$1,230
The Village at Slippery Hill Senior Apartments- 62+B1 - Two Bedroom$1,265

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 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 $1,678.

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

Today's apartment with the most square footage in Chestertown is a 1,377 square feet unit starting from $2,120 at Harborside Village Apartments.

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

The average size for a 2 Bedroom rental in Chestertown is currently 1,164 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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