2 Bedroom Apartments for Rent in Chestertown, MD (44 Rentals)

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121 Washington Ave
2 Bedroom Apartments

121 Washington Ave

121 Washington AveChestertown, MD 21620
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Baywood Village
2 Bedroom Apartments

Baywood Village

23160-23165 Baywood CtChestertown, MD 21620
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425 High St
2 Bedroom Apartments

425 High St

425 High StChestertown, MD 21620
property at 74 Swan St

74 Swan St

AberdeenMD21001
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Stansbury Manor
2 Bedroom Apartments

Stansbury Manor

1 Alder DrMiddle River, MD 21220
  • Utilities Included
Showing Results 1-44, Page 1 of 1

Chestertown, MD Local Guide

Chestertown 2 Bedroom Apartment Units with Current Availability by Neighborhood

Availability Confirmed As of: March 27, 2025

There are currently 3 available 2 Bedroom apartment units in Chestertown, MD neighborhoods that range in price from $1,600 to $2,100. Heres is today's list of the top neighborhoods in Chestertown with the most available 2 Bedroom apartments:

NeighborhoodAvailable UnitsMedian PriceMin Price
Coventry Farms3$1,675$1,600

Largest Available Chestertown and Nearby 2 Bedroom Apartments

The largest available 2 Bedroom apartment unit in Chestertown, MD is found at Riverside in the Holly Woods - Woodfield/Wyngate neighborhood and is 1,313 square feet priced from $1,999. The Berkleigh in the Miramar Landing - Gibson/Taylor neighborhood has the second largest 2 Bedroom, which is sized at 1,266 square feet and currently listed start at $2,299. Here is today’s list of the largest available 2 Bedroom units in Chestertown:

Apartment ListingModel NameSquare FootagePriced From
Riverside2 Bedroom 2 Bath - D (RS2)1,313 Sq Ft$1,999
The Berkleigh2 Bed/2 Bath-B4-Dundee1,266 Sq Ft$2,299
Arbors Greenleigh2 Bed/2 Bath-B3-Hayfield1,218 Sq Ft$2,300
ReNew BelcampCamden1,200 Sq Ft$1,945
Holly Oaks2 Bed 2 Bath1,128 Sq Ft$1,795
Perkins PlaceThe Garrett1,125 Sq Ft$1,765
Stansbury Manor2 Bedroom Townhome1,100 Sq Ft$1,719
Holly Circle Townhouses2 Bedroom 1 Bath Townhouses Available Today!1,100 Sq Ft$1,300
Kent Crossing ApartmentsMingles 2 Bedroom1,065 Sq Ft$1,600
The Willows at Cecilton2 BEDROOM935 Sq Ft$1,156

Cheapest Available Chestertown and Nearby 2 Bedroom Apartments

As of March 27, 2025 the lowest priced 2 Bedroom apartment unit in Chestertown, MD is the Two Bedroom Apartment Model starting from $1,039 at Essex Park Apartments and Townhomes in the Miramar Landing - Gibson/Taylor neighborhood. The second most affordable Chestertown 2 Bedroom is the 2 Bedroom 1 Bath Model at Brookside Station Apartments starting at $1,079 in the Trimble Meadows neighborhood. The average price for all 2 Bedroom apartments in Chestertown is currently $1,845. Here is today’s list of the cheapest available 2 Bedroom options in Chestertown:

Apartment ListingModel NamePriced From
Essex Park Apartments and TownhomesTwo Bedroom Apartment$1,039
Brookside Station Apartments2 Bedroom 1 Bath$1,079
The Willows at Cecilton2 BEDROOM$1,156
Hopkins Point by OneWallTwo Bedroom$1,176
Hartland Village ApartmentsTwo bedroom$1,183
The Greens Apartments and Townhomes2 Bedroom$1,208
Seneca Bay Apartment HomesTwo Bedroom - 853 sqft$1,265
Holly Circle Townhouses2 Bedroom 1 Bath Townhouses Available Today!$1,300
Verona at Middle RiverSicily$1,324
Seven Oaks Townhomes2 Bedrooms 1.5 Bath$1,370

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Getting Around Chestertown, MD

Walk Score®

47 / 100

Car-Dependent

Most errands require a car

Bike Score®

55 / 100

Bikeable

Some bike infrastructure

What Are Walk Score®, Transit Score®, and Bike Score® Ratings?

  • Walk Score® measures the walkability of any address.
  • Transit Score® measures access to public transit.
  • Bike Score® measures the bikeability of any address.

Frequently Asked Questions about 2 Bedroom Chestertown Apartments

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

The average rent for a 2 Bedroom Apartment in Chestertown is $1,845.

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

Today's apartment with the most square footage in Chestertown is a 1,313 square feet unit starting from $1,999 at Riverside.

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

The average size for a 2 Bedroom rental in Chestertown is currently 882 sq ft.

Expert Rental Resources

Helpful Apartment Articles, How-To's and Tips

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.

decorative image for Renting Smart: Lease Basics Every Renter Needs article

Renting Smart: Lease Basics Every Renter Needs

Written by: Christine Leonard, Esq.

Often, in the excitement of finding a new place to live, there’s a rush to make it happen, and - too often - a new tenant signs a lease without reading it carefully.

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Battling the Butts: Your Guide to the Reality of Smoke-Free Renting

Written by: Andrea Lee Negroni, JD

While many apartment buildings are “no smoking” properties, it’s hard to know exactly how many. In 2017, the National Apartment Association reported more than half of rental properties had smoke free policies.

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Understanding Amenity Fees: Know Where You Might Be Able to Save Money

Written by: Amber Kanuckel

With the rising costs of housing, a lot of renters are asking this question: Is it possible to opt out of various amenities that your rental property offers so that you can avoid paying the fees.

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How Your Move-In Inspection Can Protect Your Security Deposit

Written by: Christine Leonard, Esq.

If you’re anything like most people, housing costs represent a huge chunk of your monthly budget. On top of that, moving can be both a stressful and expensive affair.