3 Bedroom Apartments for Rent in Chestertown, MD (51 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

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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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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Renting Smart: Lease Basics Every Renter Needs

Demystify Your Rental Lease. Learn the basics about renting, deposits, and tenant/landlord responsibilities. Rent smart and avoid surprises. | Renter University at ApartmentHomeLiving.com

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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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Stansbury Manor
3 Bedroom Apartments

Stansbury Manor

1 Alder DrMiddle River, MD 21220
  • Utilities Included

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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Showing Results 1-50, Page 1 of 2

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 Enclave at Box Hill in the Harford Green neighborhood and is 1,719 square feet priced from $3,323. Aberdeen Proving Ground on Post Housing in the Greenway Farm neighborhood has the second largest 3 Bedroom, which is sized at 1,560 square feet and currently listed start at $2,125. Here is today’s list of the largest available 3 Bedroom units in Chestertown:

Apartment ListingModel NameSquare FootagePriced From
Enclave at Box Hill3 Bed/2.5 Bath Townhome 2 Car Garage-R1,719 Sq Ft$3,323
Aberdeen Proving Ground on Post HousingPatriot Village - Falls1,560 Sq Ft$2,125
Carriage Court Apartments3 bedroom 3 bathrooms1,450 Sq Ft$1,600
RiversideThe Baysider 21,376 Sq Ft$2,199
Holly Oaks3 Bed 2 Bath1,372 Sq Ft$2,225
Kingston Townhomes3 Bedrooms 1 Bath1,100 Sq Ft$1,684
Windsor Valley ApartmentsWindsor III- 3 BR, 2 BA1,080 Sq Ft$1,050
Hopkins Point by OneWallThree Bedroom985 Sq Ft$1,780

Cheapest Available Chestertown and Nearby 3 Bedroom Apartments

As of June 14, 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 bedroom 3 bathrooms Model at Carriage Court Apartments starting at $1,600 in the Trimble Meadows neighborhood. The average price for all 3 Bedroom apartments in Chestertown is currently $2,082. 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
Carriage Court Apartments3 bedroom 3 bathrooms$1,600
Hopkins Point by OneWallThree Bedroom$1,630
Kingston Townhomes3 Bedrooms 1 Bath$1,684
Aberdeen Proving Ground on Post HousingEdgewood - Morgan$1,950
RiversideThe Baysider 2$2,199
Holly Oaks3 Bed 2 Bath$2,225
Enclave at Box Hill3 Bed/2.5 Bath Townhome 2 Car Garage-R$3,323

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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Pet Friendly Lifestyle

Ranked #

Among cities in Maryland for Apartment listings with Pet Friendly Amenities.

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

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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 $2,082.

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

Today's apartment with the most square footage in Chestertown is a 1,719 square feet unit starting from $3,323 at Enclave at Box Hill.

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

The average size for a 3 Bedroom rental in Chestertown is currently 1,742 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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How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide

Written by: Robin Stewart

Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.

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Pet-Friendly Renting: Everything You Need to Know Before You Move

Written by: Christine Leonard, Esq.

For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.

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Creative Ways Developers Reimagine Retail Spaces as Residential Units

Written by: Robin Stewart

Adaptive reuse is when a commercial property is converted and repurposed. The real estate industry has embraced a growing number of these projects.

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Neighborhood and Market Insights: How to Choose the Right Area to Rent

Written by: Robin Stewart

Apartment-hunting can be a gargantuan task. Renters have a wish list of items—some luxuries, some necessities—but finding what you seek in the right place is perhaps the most important part of the journey.