3 Bedroom Apartments for Rent in Chestertown, MD (52 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

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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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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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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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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Stansbury Manor
3 Bedroom Apartments

Stansbury Manor

1 Alder DrMiddle River, MD 21220
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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 Foxridge Townhomes in the Hopewell Point neighborhood and is 1,728 square feet priced from $1,672. Riverside in the Holly Woods - Woodfield/Wyngate neighborhood has the second largest 3 Bedroom, which is sized at 1,644 square feet and currently listed start at $2,479. 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$1,672
Riverside3 Bedroom 3 Bath Townhome (RS2)1,644 Sq Ft$2,479
Aberdeen Proving Ground on Post HousingPatriot Village - Falls1,560 Sq Ft$2,125
Arbors GreenleighGreystone1,448 Sq Ft$2,800
Winston's Choice Family TownhomesUNIT A-INTERIOR UNIT1,401 Sq Ft$1,339
Seven Oaks Townhomes3 Bedrooms 1.5 Bath1,209 Sq Ft$1,739
Kingston Townhomes3 Bedrooms 1 Bath1,100 Sq Ft$1,520
Village Of Carrollwood3BR/1.5BA Townhome Gray1,100 Sq Ft$1,970
Windsor Valley ApartmentsWindsor III- 3 BR, 2 BA1,080 Sq Ft$1,050
Hopkins Point by OneWallThree Bedroom985 Sq Ft$1,855

Cheapest Available Chestertown and Nearby 3 Bedroom Apartments

As of January 03, 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 UNIT A-INTERIOR UNIT Model at Winston's Choice Family Townhomes starting at $1,339 in the Greenway Farm neighborhood. The average price for all 3 Bedroom apartments in Chestertown is currently $1,930. 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
Winston's Choice Family TownhomesUNIT A-INTERIOR UNIT$1,339
Kingston Townhomes3 Bedrooms 1 Bath$1,524
Foxridge Townhomes3 Bedrooms 1 Bath$1,674
Seven Oaks Townhomes3 Bedrooms 1.5 Bath$1,735
Hopkins Point by OneWallThree Bedroom$1,780
Aberdeen Proving Ground on Post HousingEdgewood - Morgan$1,950
Village Of Carrollwood3BR/1.5BA Townhome Gray$1,970
Riverside3 Bedroom 2 Bath - B (RS2)$2,099
Arbors GreenleighGreystone$2,800

Don't Settle: How to Negotiate Your Apartment Lease and Save Money

Discover the insider tips from an attorney and real estate agent on how to negotiate your next apartment lease. Find out what's on the table and what's not, so you can save money and get the best terms possible.

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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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How much rent can you afford?

The common "Rule of Thumb" is that rent should be no more than 30% of your income. How much is that? Enter your monthly income and click "Calculate My Budget" to find out.

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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!

Explore Chestertown, MD Rentals by Map

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See the most popular apartments and homes in Chestertown, MD

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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 $1,930.

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 $1,672 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 1,961 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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Renting with Roommates: Realistic Expectations for Shared Lease

Written by: Christine Leonard, Esq.

Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.

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How to Make Your Apartment Holiday-Ready: Renter-Friendly Tips

Written by: Justin Habersaat

Getting your apartment ready for the holidays can be exciting but sometimes challenging in a smaller space. Here are some modern tips to keep things festive, safe, and inviting this season.

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Apartment Common Area Rules: What Renters Need to Know

Written by: Christine Leonard, Esq.

Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.

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How to Negotiate Your Apartment Lease and Save Money

Written by: Christine Leonard, Esq.

Everything is a negotiation in real estate!