2 Bedroom Apartments for Rent in Chestertown, MD (51 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

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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425 High St
2 Bedroom Apartments

425 High St

425 High StChestertown, MD 21620

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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Smart Renter's Guide: Calculating Affordable Rent & Housing Costs

Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.

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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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Stansbury Manor
2 Bedroom Apartments

Stansbury Manor

1 Alder DrMiddle River, MD 21220
  • Utilities Included
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Chestertown, MD Local Guide

Chestertown 2 Bedroom Apartment Units with Current Availability by Neighborhood

Availability Confirmed As of: June 21, 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 Riverside in the Holly Woods - Woodfield/Wyngate neighborhood and is 1,313 square feet priced from $2,183. Arbors Greenleigh in the Miramar Landing - Gibson/Taylor neighborhood has the second largest 2 Bedroom, which is sized at 1,218 square feet and currently listed start at $2,350. 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$2,183
Arbors Greenleigh2 Bed/2 Bath-B3-Hayfield1,218 Sq Ft$2,350
ReNew BelcampCamden1,200 Sq Ft$1,850
Holly Oaks2 Bed 2 Bath1,128 Sq Ft$1,785
Holly Circle Townhouses2 Bedroom 1.5 Bath End Unit Townhouse1,100 Sq Ft$1,375
Kent Crossing ApartmentsMingles 2 Bedroom1,065 Sq Ft$1,600
The Berkleigh2 Bed/2 Bath-B1-Bohemia1,046 Sq Ft$2,499
Harborside Village Apartments2 bedroom, 2 baths- waterfront/view (unit C)1,000 Sq Ft$1,625
Seven Oaks Townhomes2 Bedrooms 1.5 Bath968 Sq Ft$1,480
The Willows at Cecilton2 BEDROOM935 Sq Ft$1,156

Cheapest Available Chestertown and Nearby 2 Bedroom Apartments

As of June 21, 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 2 BEDROOM Model at The Willows at Cecilton starting at $1,156 . The average price for all 2 Bedroom apartments in Chestertown is currently $1,753. 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
The Willows at Cecilton2 BEDROOM$1,156
Seneca Bay Apartment HomesTwo Bedroom - 806 sqft$1,160
Hartland Village ApartmentsTwo bedroom$1,183
The Greens Apartments and Townhomes2 Bedroom$1,208
Hopkins Point by OneWallTwo Bedroom$1,250
Verona at Middle RiverSicily$1,324
Holly Circle Townhouses2 Bedroom 1.5 Bath End Unit Townhouse$1,375
Harford Commons2 Bedroom$1,389
Beacon Pointe Apartments and TownhomesB1-2BD/1BA$1,410

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Remember the 3 Rules of Real Estate:
Location, Location, Location!

Explore Chestertown, MD Rentals by Map

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See the most popular apartments and homes in Chestertown, MD

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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 $1,753.

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 $2,183 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 1,787 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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Roommate Matching: Finding the Right Fit and Avoiding Pitfalls

Written by: Cheryl Bowman

A fantastic way to save money and enjoy a built-in community is to share an apartment. However, a bad roommate situation can turn your dream rental into a nightmare.

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The Art of the Rental Viewing: What to look for during a property tour

Written by: Marie Brown

You’ve scrolled through countless listings, walked through a blur of rentals, and finally found what feels like the one. The pictures? Fantastic. The neighborhood seems just right.

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Know Your Budget: Calculating What You Can Realistically Afford When Renting

Written by: Lauren Harrington

Renting an apartment or house isn’t just about looking through online ads, choosing a few apartments or homes you want to tour, filling out an application, and putting down a deposit. Those things are all necessary and important.

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The Freedom of Short-Term Leases: Exploring the Advantages for Renters

Written by: Bobbi Jackson

If you’re looking to relocate right now, a popular solution that may best fit your current rental needs is a short-term lease.