2 Bedroom Apartments for Rent in Chestertown, MD (52 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
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Chestertown, MD Local Guide

Chestertown 2 Bedroom Apartment Units with Current Availability by Neighborhood

Availability Confirmed As of: July 31, 2025

There are currently 2 available 2 Bedroom apartment units in Chestertown, MD neighborhoods that range in price from $1,600 to $1,675. Heres is today's list of the top neighborhoods in Chestertown with the most available 2 Bedroom apartments:

NeighborhoodAvailable UnitsMedian PriceMin Price
Coventry Farms2$1,637$1,600

Largest Available Chestertown and Nearby 2 Bedroom Apartments

The largest available 2 Bedroom apartment unit in Chestertown, MD is found at Arbors Greenleigh in the Miramar Landing - Gibson/Taylor neighborhood and is 1,277 square feet priced from $2,400. Riverside in the Holly Woods - Woodfield/Wyngate neighborhood has the second largest 2 Bedroom, which is sized at 1,202 square feet and currently listed start at $1,979. Here is today’s list of the largest available 2 Bedroom units in Chestertown:

Apartment ListingModel NameSquare FootagePriced From
Arbors Greenleigh2 Bed/2 Bath Loft-B2L-Levere1,277 Sq Ft$2,400
Riverside2 Bedroom 2 Bath - W (RS2)1,202 Sq Ft$1,979
ReNew BelcampCamden1,200 Sq Ft$1,925
Kent Crossing ApartmentsMingles 2 Bedroom1,065 Sq Ft$1,600
The Berkleigh2 Bed/2 Bath-B1-Bohemia1,046 Sq Ft$2,449
Perkins PlaceThe Calvert1,000 Sq Ft$1,890
Seven Oaks Townhomes2 Bedrooms 1.5 Bath968 Sq Ft$1,487
The Willows at Cecilton2 BEDROOM935 Sq Ft$1,156
Woodsdale Apartments2 Bedrooms 1.5 Bath844 Sq Ft$1,357
The Greens Apartments and Townhomes2 Bedroom742 Sq Ft$1,208

Cheapest Available Chestertown and Nearby 2 Bedroom Apartments

As of July 31, 2025 the lowest priced 2 Bedroom apartment unit in Chestertown, MD is the Two Bedroom Apartment Model starting from $1,143 at Kings Mill Apartments and Townhomes in the Miramar Landing - Gibson/Taylor neighborhood. The second most affordable Chestertown 2 Bedroom is the Two Bedroom - 806 sqft Model at Seneca Bay Apartment Homes starting at $1,150 . The average price for all 2 Bedroom apartments in Chestertown is currently $1,776. Here is today’s list of the cheapest available 2 Bedroom options in Chestertown:

Apartment ListingModel NamePriced From
Kings Mill Apartments and TownhomesTwo Bedroom Apartment$1,143
Seneca Bay Apartment HomesTwo Bedroom - 806 sqft$1,150
The Willows at Cecilton2 BEDROOM$1,156
Hyde Park ApartmentsTwo Bedroom One Bath$1,163
The Greens Apartments and Townhomes2 Bedroom$1,208
Hartland Village ApartmentsTwo bedroom$1,231
Essex Park Apartments and TownhomesTwo Bedroom with Den Apartment$1,239
Hopkins Point by OneWallTwo Bedroom$1,250
Perryman Station Senior Apartments, 62+2 bedroom$1,297
Verona at Middle RiverSicily$1,324

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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

What is the Cheapest apartment in Chestertown with 2 Bedroom?

Currently the most affordable 2 Bedroom in Chestertown is at Kings Mill Apartments and Townhomes listed at $1,143.

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

The average rent for a 2 Bedroom Apartment in Chestertown is $1,776.

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

Today's apartment with the most square footage in Chestertown is a 1,277 square feet unit starting from $2,400 at Arbors Greenleigh.

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

The average size for a 2 Bedroom rental in Chestertown is currently 1,253 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.

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