Cheap Apartments for Rent in Chestertown, MD from $500 (54 Rentals)

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Search the lowest-cost Apartments available for rent right now in Chestertown.

What Does “Rent Burdened” Mean? How Much Rent Is Too Much

Learn the official definition (spending 30% or more of your gross income on housing) and how to calculate your exact rent-to-income ratio. This guide offers expert tips on factoring in total housing costs (including utilities and fees) and budgeting accurately to avoid unnecessary financial strain.

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Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between

Thinking about getting a co-signer for your rental application? We break down what a co-signer is, the potential benefits, and the serious risks for both parties. Find out if it's the right choice for you.

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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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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
1 to 3 Bedroom Apartments

Stansbury Manor

1 Alder DrMiddle River, MD 21220
  • Utilities Included

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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Chestertown, MD Local Guide

Cheapest Available Chestertown Apartments for Rent and Nearby

 

The cheapest available apartment rental in Chestertown, MD is a Studio unit found at The Greens Apartments and Townhomes in the Hopewell Point neighborhood priced from $687. Windsor Valley Apartments in the Goose Pond Estates neighborhood has the second lowest priced unit, which is a 1 Bed apartment currently listed from $765. Here is today’s list of the most affordable Chestertown apartments for rent:

Apartment ListingModel NameBed/BathPriced From
The Greens Apartments and TownhomesStudioStudio,1BA$687
Windsor Valley ApartmentsWindsor III- 1 BR, 1 BA1BR,1BA$765
Kings Mill Apartments and TownhomesOne bedroom Apartment1BR,1BA$785
Hartland Village ApartmentsStudioStudio,1BA$852
Hyde Park ApartmentsStudio 1 BathroomStudio,1BA$988
Seneca Bay Apartment HomesOne Bedroom1BR,1BA$1,040
Hopkins Point by OneWallTwo Bedroom2BR,1BA$1,075
Middle River Overlook2BD/1BA2BR,1BA$1,119
Magnolia Farms2 Bedroom Apt2BR,1BA$1,190

Best Value Apartments for Rent in Chestertown, MD and Nearby

As of June 21, 2026 the best value apartment in the Chestertown area is the $1.00 price per square foot 3 Bedrooms 1 Bath Model at Foxridge Townhomes in the in the Hopewell Point neighborhood starting from $1,723. The second greatest value Chestertown apartment is the 3 bedroom 3 bathrooms Model at Carriage Court Apartments starting at $1,600 with a $1.10 price per square foot in the Trimble Meadows neighborhood. Here is today’s list of the best values for Chestertown apartments based on price per square foot:

Apartment ListingModel NameBed/BathPrice Per Sq.Ft.
Foxridge Townhomes3 Bedrooms 1 Bath3BR,1BA$1.00
Carriage Court Apartments3 bedroom 3 bathrooms3BR,2BA$1.10
Kingston Townhomes3 Bedrooms 1 Bath3BR,1BA$1.53
The Village at Slippery Hill Senior Apartments- 62+B1 - Two Bedroom2BR,1BA$1.48
Magnolia Farms2 Bedroom Apt2BR,1BA$1.40
7019 Church Hill Rd, Unit B7019 Church Hill Rd2BR,1BA$1.41
Middle River Overlook2BD/1BA2BR,1BA$1.55
Seneca Bay Apartment HomesOne Bedroom1BR,1BA$1.45
Hyde Park ApartmentsStudio 1 BathroomStudio ,1BA$1.58
Windsor Valley ApartmentsWindsor I & II- 1 BR, 1 BA1BR,1BA$1.36

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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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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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.

Pet Friendliness Lifestyle Score

Pet Friendly

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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 Cheap Chestertown Apartments

What is the Cheapest Studio apartment in Chestertown?

Currently the most affordable Cheap Studio Apartment in Chestertown is at The Greens Apartments and Townhomes listed at $687.

How much is rent for a Cheap One Bedroom Chestertown Apartment?

The lowest price for a Cheap One Bedroom Chestertown Apartment is $765 at Windsor Valley Apartments.

What is the lowest price for a Cheap Two Bedroom Chestertown Apartment for rent?

Today's best deal for a Cheap Two Bedroom Apartment in Chestertown is starting from $950 at Windsor Valley Apartments.

What is the most affordable Chestertown Three Bedroom Apartment?

The best deal on a cheap Chestertown Three Bedroom Apartment rental is at Windsor Valley Apartments and starts from $1,050.

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

decorative image for Apartment Occupancy Rates: Renter Attraction vs Renter Retention article

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.

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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.