2 Bedroom Apartments for Rent in Chester, MD (55 Rentals)

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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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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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property at 3 Elliott Rd

3 Elliott Rd

AnnapolisMD21403
Showing Results 1-50, Page 1 of 2

Chester, MD Local Guide

Largest Available Chester and Nearby 2 Bedroom Apartments

The largest available 2 Bedroom apartment unit in Chester, MD is found at Aventon Annapolis in the Monticello neighborhood and is 1,418 square feet . Creekstone Village Apartments in the Sloop Cove Landing neighborhood has the second largest 2 Bedroom, which is sized at 1,330 square feet and currently listed start at $2,952. Here is today’s list of the largest available 2 Bedroom units in Chester:

Apartment ListingModel NameSquare FootagePriced From
Aventon AnnapolisB11 Den1,418 Sq FtCall for Rates
Creekstone Village ApartmentsB5_DC1,330 Sq Ft$2,952
Mariner Bay at Annapolis Town Center2 bedroom/2 bath1,310 Sq Ft$3,011
MarisB71,288 Sq Ft$3,016
Gardens of AnnapolisFull Reno Van Gogh1,169 Sq Ft$3,600
Avalon AnnapolisB7 - Design Collection II1,167 Sq Ft$3,285
Annapolis Bay2 Bedroom, 2 Bathroom 1,124 SF 22B1,124 Sq Ft$2,580
The Reserve at Stoney CreekThe Sloop1,093 Sq Ft$2,270
Annapolis Roads2BR 2BA1,055 Sq Ft$2,113
Oakland Hills2 Bedroom1,037 Sq Ft$2,339

Cheapest Available Chester and Nearby 2 Bedroom Apartments

As of June 19, 2025 the lowest priced 2 Bedroom apartment unit in Chester, MD is the two bedroom Model starting from $1,054 at Mulberry Estates in the Chesapeake by Del Webb neighborhood. The second most affordable Chester 2 Bedroom is the B1-2BD/1BA Model at Beacon Pointe Apartments and Townhomes starting at $1,410 in the Edgemere neighborhood. The average price for all 2 Bedroom apartments in Chester is currently $2,685. Here is today’s list of the cheapest available 2 Bedroom options in Chester:

Apartment ListingModel NamePriced From
Mulberry Estatestwo bedroom$1,054
Beacon Pointe Apartments and TownhomesB1-2BD/1BA$1,410
The Villages at Marley Station ApartmentsB1$1,499
Americana Southdale2 Bedroom$1,719
Quiet Waters LandingB1-2BD/1BA$1,854
Nautilus PointNautilus | B1 | Reno$1,895
Annapolis Roads2BR 2BA$2,113
Bay Hills Apartments2B1B$2,233
The Reserve at Stoney CreekThe Sloop$2,270
Westwinds Apartments2 Bedroom 2 Bath Renovated$2,335

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

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Getting Around Chester, MD

Walk Score®

40 / 100

Car-Dependent

Most errands require a car

Bike Score®

65 / 100

Bikeable

Some bike infrastructure

What Are Walk Score®, Transit Score®, and Bike Score® Ratings?

  • Walk Score® measures the walkability of any address.
  • Transit Score® measures access to public transit.
  • Bike Score® measures the bikeability of any address.

Frequently Asked Questions about 2 Bedroom Chester Apartments

What is the Cheapest apartment in Chester with 2 Bedroom?

Currently the most affordable 2 Bedroom in Chester is at Mulberry Estates listed at $1,054.

How much is the average rent for a 2 Bedroom Chester Apartment?

The average rent for a 2 Bedroom Apartment in Chester is $2,685.

What is the largest available 2 Bedroom Chester Apartment for rent?

Today's apartment with the most square footage in Chester is a 1,418 square feet unit at Aventon Annapolis.

What is the average size for Chester 2 Bedroom Apartments for rent?

The average size for a 2 Bedroom rental in Chester is currently 1,029 sq ft.

Expert Rental Resources

Helpful Apartment Articles, How-To's and Tips

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.

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Roommate Matching: Finding the Right Fit and Avoiding Pitfalls

Written by: Cheryl Bowman

A fantastic way to save money and enjoy a built-in community is to share an apartment. However, a bad roommate situation can turn your dream rental into a nightmare.

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The Art of the Rental Viewing: What to look for during a property tour

Written by: Marie Brown

You’ve scrolled through countless listings, walked through a blur of rentals, and finally found what feels like the one. The pictures? Fantastic. The neighborhood seems just right.

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Know Your Budget: Calculating What You Can Realistically Afford When Renting

Written by: Lauren Harrington

Renting an apartment or house isn’t just about looking through online ads, choosing a few apartments or homes you want to tour, filling out an application, and putting down a deposit. Those things are all necessary and important.

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The Freedom of Short-Term Leases: Exploring the Advantages for Renters

Written by: Bobbi Jackson

If you’re looking to relocate right now, a popular solution that may best fit your current rental needs is a short-term lease.