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

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 Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro

Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.

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Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting

Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.

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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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Stansbury Manor
2 Bedroom Apartments

Stansbury Manor

1 Alder DrMiddle River, MD 21220
  • Utilities Included

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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Chestertown, MD Local Guide

Chestertown 2 Bedroom Apartment Units with Current Availability by Neighborhood

Availability Confirmed As of: September 15, 2025

There are currently 2 available 2 Bedroom apartment units in Chestertown, MD neighborhoods that range in price from $1,600 to $2,500. Heres is today's list of the top neighborhoods in Chestertown with the most available 2 Bedroom apartments:

NeighborhoodAvailable UnitsMedian PriceMin Price
Coventry Farms2$1,675$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. Arbors Greenleigh in the Miramar Landing - Gibson/Taylor neighborhood has the second largest 2 Bedroom, which is sized at 1,277 square feet and currently listed start at $2,400. 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
Arbors Greenleigh2 Bed/2 Bath Loft-B2L-Levere1,277 Sq Ft$2,400
The Enclave at Box Hill2 Bed/2 Bath Den-N1,245 Sq Ft$2,570
ReNew BelcampCamden1,200 Sq Ft$1,875
Holly Oaks2 Bed 2 Bath1,128 Sq Ft$1,785
Kent Crossing ApartmentsMingles 2 Bedroom1,065 Sq Ft$1,600
Aberdeen Proving Ground on Post HousingPatriot Village - Stream1,060 Sq Ft$1,895
Harborside Village Apartments2 bedroom, 2 baths- waterfront/view (unit C)1,000 Sq Ft$1,625
Perkins PlaceThe Calvert1,000 Sq Ft$1,760
The Willows at Cecilton2 BEDROOM935 Sq Ft$1,156

Cheapest Available Chestertown and Nearby 2 Bedroom Apartments

As of September 15, 2025 the lowest priced 2 Bedroom apartment unit in Chestertown, MD is the B1 - Two Bedroom Townhome Model starting from $699 at The Village at Slippery Hill II . The second most affordable Chestertown 2 Bedroom is the Two Bedroom - 806 sqft Model at Seneca Bay Apartment Homes starting at $1,140 in the Miramar Landing - Gibson/Taylor 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
The Village at Slippery Hill IIB1 - Two Bedroom Townhome$699
Seneca Bay Apartment HomesTwo Bedroom - 806 sqft$1,140
Kings Mill Apartments and TownhomesTwo Bedroom Apartment$1,140
The Willows at Cecilton2 BEDROOM$1,156
The Greens Apartments and Townhomes2 Bedroom$1,208
Hartland Village ApartmentsTwo bedroom$1,231
Hopkins Point by OneWallTwo Bedroom$1,250
Perryman Station Senior Apartments, 62+2 bedroom$1,297
Verona at Middle RiverSicily$1,324
Woodsdale Apartments2 Bedrooms 1.5 Bath$1,372

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

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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 The Village at Slippery Hill II listed at $699.

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 1,313 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 749 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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The Rental Move-In Inspection Checklist: A Guide for Renters

Written by: Trey Huguley

The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.

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Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between

Written by: Christine Leonard, Esq.

For many people, obstacles can arise during the rental application process for a variety of issues.

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The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro

Written by: Christine Leonard, Esq.

Hard truth. Moving is never easy. I’ve done it all – from local moves to cross-country relocations From packing to unpacking the last box, I have found moving to be an exhausting, expensive and stressful experience every time.

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Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting

Written by: Christine Leonard, Esq.

Throughout the day, think about all the times that you have to pay for something. So many of us reach automatically for a credit card or even our phone for a quick payment.