2 Bedroom Apartments for Rent in Chestertown, MD (53 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

Exploring Rental Options: Apartments, Townhomes, and Lofts—Oh My!

Looking for the perfect rental? From apartments and condos to lofts and single family rentals, explore the unique pros and cons of each rental type to help you land in your perfect new place.

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Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags

Looking for the perfect new rental? Learn great ways to spot the perfect apartment for you, identify common red flags, and avoid rental issues and scams with these expert provided actionable tips.

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The Berkleigh
$2,475 - $2,950

Total Monthly Price

Base Rent$1,916 - $2,956
Total Monthly PriceVaries
2 Bedroom Apartments Available Now

The Berkleigh

6221 Greenleigh AveBaltimore, MD 21220
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Arbors Greenleigh
$2,325 - $2,525

Total Monthly Price

Base Rent$1,623 - $3,073
Total Monthly PriceVaries
2 Bedroom Apartments Available Sep 18

Arbors Greenleigh

11550 Crossroads CirBaltimore, MD 21220
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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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Magnolia Farms
2 Bedroom Apartments

Magnolia Farms

28 E Bel Air AveAberdeen, MD 21001
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Merion Village
2 Bedroom Apartments

Merion Village

904 Edgewood RdEdgewood, MD 21040
Senior Living

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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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 $2,153. 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$2,153
The Berkleigh2 Bed/2 Bath Loft-B2-L-Rock Hall1,307 Sq Ft$2,956
Holly Oaks2 Bed 2 Bath w/ Den1,272 Sq Ft$2,050
Enclave at Box Hill2 Bed 2 Bath Den-N1,245 Sq Ft$2,937
Eagle Rock Apartments at BelcampB4-2x2D1,200 Sq Ft$1,510
Stansbury Manor2 Bedroom Townhome1,100 Sq Ft$1,649
Aberdeen Proving Ground on Post HousingPatriot Village - Stream1,060 Sq Ft$1,895
Perkins PlaceThe Calvert1,000 Sq Ft$1,762
Seven Oaks Townhomes2 Bedrooms 1.5 Bath968 Sq Ft$1,591

Cheapest Available Chestertown and Nearby 2 Bedroom Apartments

As of September 13, 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 Apartment Model at Essex Park Apartments and Townhomes starting at $1,039 in the Miramar Landing - Gibson/Taylor neighborhood. The average price for all 2 Bedroom apartments in Chestertown is currently $1,758. 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
Essex Park Apartments and TownhomesTwo Bedroom Apartment$1,039
Hopkins Point by OneWallTwo Bedroom$1,075
Kings Mill Apartments and TownhomesTwo Bedroom Apartment$1,170
The Greens Apartments and Townhomes2 Bedroom$1,170
Hyde Park ApartmentsTwo Bedroom One Bath$1,176
Hartland Village ApartmentsTwo bedroom$1,181
Middle River Overlook2BD/1BA$1,256
The Village at Slippery Hill Senior Apartments- 62+B1 - Two Bedroom$1,265
Seneca Bay Apartment HomesTwo Bedroom - 806 sqft$1,295

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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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 $1,758.

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 998 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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Exploring Rental Options: Apartments, Townhomes, and Lofts - Oh My!

Written by: Robin Stewart

Where do you see yourself? When you think of home, sweet home, are you in a 3/2 apartment? Dreaming of a tall townhome? Maybe an industrial loft heavy on cool vibes is on your visioning board.

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Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags

Written by: Robin Stewart

Renters want to find a great apartment, the right place for them, one that checks all the boxes of location, rental cost, amenities, safety, and more.

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First Apartment Regrets: Real Renters Share What They'd Do Differently

Written by: Robin Stewart

Hindsight is 20/20. Live and Learn. With age comes wisdom. We’re familiar with all those expressions, and all of them apply to lessons first-time renters learn.

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Renters Insurance 101: What It Is, What It Covers, and Why You Need It

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Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.