3 Bedroom Apartments for Rent in Chestertown, MD (48 Rentals)

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200 N Queen St
3 Bedroom Apartments

200 N Queen St

200 N Queen StChestertown, MD 21620
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Baywood Village
3 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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Arbors Greenleigh
$3,000 - $3,073

Total Monthly Price

Base Rent$1,623 - $3,073
Total Monthly PriceVaries
3 Bedroom Apartments Available Sep 16

Arbors Greenleigh

11550 Crossroads CirBaltimore, MD 21220
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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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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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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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Stansbury Manor
3 Bedroom Apartments

Stansbury Manor

1 Alder DrMiddle River, MD 21220
  • Utilities Included
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Magnolia Farms
3 Bedroom Apartments

Magnolia Farms

28 E Bel Air AveAberdeen, MD 21001
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Showing Results 1-48, Page 1 of 1

Chestertown, MD Local Guide

Largest Available Chestertown and Nearby 3 Bedroom Apartments

The largest available 3 Bedroom apartment unit in Chestertown, MD is found at Foxridge Townhomes in the Essex neighborhood and is 1,728 square feet priced from $1,781. Enclave at Box Hill in the Harford Green neighborhood has the second largest 3 Bedroom, which is sized at 1,719 square feet and currently listed start at $2,879. Here is today’s list of the largest available 3 Bedroom units in Chestertown:

Apartment ListingModel NameSquare FootagePriced From
Foxridge Townhomes3 Bedrooms 1 Bath1,728 Sq Ft$1,781
Enclave at Box Hill3 Bed/2.5 Bath Townhome 2 Car Garage-R1,719 Sq Ft$2,879
Aberdeen Proving Ground on Post HousingPatriot Village - Falls1,560 Sq Ft$2,125
RiversideThe Baysider1,376 Sq Ft$2,249
Seven Oaks Townhomes3 Bedrooms 1.5 Bath1,209 Sq FtCall for Rates
Eagle Rock Apartments at BelcampC1-3x21,208 Sq Ft$2,255
Kingston Townhomes3 Bedrooms 1 Bath1,100 Sq Ft$1,658
Windsor Valley ApartmentsWindsor III- 3 BR, 2 BA1,080 Sq Ft$1,050

Cheapest Available Chestertown and Nearby 3 Bedroom Apartments

As of September 13, 2026 the lowest priced 3 Bedroom apartment unit in Chestertown, MD is the Windsor III- 3 BR, 2 BA Model starting from $1,050 at Windsor Valley Apartments in the Goose Pond Estates neighborhood. The second most affordable Chestertown 3 Bedroom is the 3 Bedrooms 1 Bath Model at Kingston Townhomes starting at $1,658 in the Miramar Landing - Gibson/Taylor neighborhood. The average price for all 3 Bedroom apartments in Chestertown is currently $2,035. Here is today’s list of the cheapest available 3 Bedroom options in Chestertown:

Apartment ListingModel NamePriced From
Windsor Valley ApartmentsWindsor III- 3 BR, 2 BA$1,050
Kingston Townhomes3 Bedrooms 1 Bath$1,658
Foxridge Townhomes3 Bedrooms 1 Bath$1,781
Seven Oaks Townhomes3 Bedrooms 1.5 Bath$1,815
Aberdeen Proving Ground on Post HousingEdgewood - Morgan$1,950
RiversideThe Baysider$2,249
Eagle Rock Apartments at BelcampC1-3x2$2,255
Enclave at Box Hill3 Bed/2.5 Bath Townhome 2 Car Garage-R$2,879

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!

Explore Chestertown, MD Rentals by Map

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Frequently Asked Questions about 3 Bedroom Chestertown Apartments

What is the Cheapest apartment in Chestertown with 3 Bedroom?

Currently the most affordable 3 Bedroom in Chestertown is at Windsor Valley Apartments listed at $1,050.

How much is the average rent for a 3 Bedroom Chestertown Apartment?

The average rent for a 3 Bedroom Apartment in Chestertown is $2,035.

What is the largest available 3 Bedroom Chestertown Apartment for rent?

Today's apartment with the most square footage in Chestertown is a 1,728 square feet unit starting from $1,781 at Foxridge Townhomes.

What is the average size for Chestertown 3 Bedroom Apartments for rent?

The average size for a 3 Bedroom rental in Chestertown is currently 1,260 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

Written by: Robin Stewart

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.