3 Bedroom Apartments for Rent in Chestertown, MD (51 Rentals)

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property at 351 Calvert St

$2,000

Total Monthly Price

Total Monthly Price

Base Rent
$2,000
Total Monthly Price
$2,000

3 Bedroom, 1 Bath Townhome for Rent

Available Now

351 Calvert St

ChestertownMD21620
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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

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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Enclave at Box Hill
Rent Specials
$3,521 - $3,779
Total Monthly Price

Total Monthly Price

Base Rent
$1,839 - $6,023
Total Monthly Price
Varies
3 Bedroom Apartments Available Now

Enclave at Box Hill

3405 McCurley DrAbingdon, MD 21009
Corporate Housing
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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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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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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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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 $1,723. 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 $3,553. 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$1,723
Enclave at Box Hill3 Bed/2.5 Bath Townhome 2 Car Garage-R1,719 Sq Ft$3,553
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 Baysider1,376 Sq Ft$2,179
Holly Oaks3 Bed 2 Bath1,372 Sq Ft$2,225
Seven Oaks Townhomes3 Bedrooms 1.5 Bath1,209 Sq FtCall for Rates
Eagle Rock Apartments at BelcampC1-3x21,208 Sq Ft$2,210
Kingston Townhomes3 Bedrooms 1 Bath1,100 Sq Ft$1,666
Hopkins Point by OneWallThree Bedroom/Two Bath TH1,097 Sq Ft$1,822

Cheapest Available Chestertown and Nearby 3 Bedroom Apartments

As of July 30, 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 $2,005. 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
Kingston Townhomes3 Bedrooms 1 Bath$1,666
Foxridge Townhomes3 Bedrooms 1 Bath$1,723
Seven Oaks Townhomes3 Bedrooms 1.5 Bath$1,740
Aberdeen Proving Ground on Post HousingEdgewood - Morgan$1,950
RiversideThe Baysider$2,179
Holly Oaks3 Bed 2 Bath$2,225
Eagle Rock Apartments at BelcampC1-3x2$2,280
Enclave at Box Hill3 Bed/2.5 Bath Townhome 2 Car Garage-R$3,553

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

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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!

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 $2,005.

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 $1,723 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 988 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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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.

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Apartment Occupancy Rates: Renter Attraction vs Renter Retention

Written by: Robin Stewart

There’s a tenet in marketing about client or customer attraction and retention. Studies and data have consistently shown it costs less to keep a current customer than to attract a new one.

decorative image for How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide article

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.