13

Chester, MD Homes for Rent

Section Image
  • 226 Bentons Pleasure Rd, Chester, MD 21619
    226 Bentons Pleasure Rd, Chester, MD 21619
    226 Bentons Pleasure Rd, Chester, MD 21619
    /49

    $4,500 Per Month

    • 4 Beds
    • 3 Baths
    • 2,876 Sq Ft
    • House for Rent

    226 Bentons Pleasure Rd, Chester, MD 21619

    Awesome water front living on Cox Creek! This wonderful, spacious Home is a must see on Kent Islands in popular Bentons Pleasure Neighborhood! HUGE GREAT ROOM AND PRIMARY BEDROOM/BATH ADDITION! Wonderful open concept kitchen/ dining room & great room combo w/stone fireplace, handsome built-in book cases, Brazilian cherry hardwood floors, recessed lighting, custom wet bar, wine cooler and water

    Michael Roenigk Chaney Homes, LLC

    226 Bentons Pleasure Rd, Chester, MD 21619
  • 800 Abruzzi Dr, Chester, MD 21619
    800 Abruzzi Dr, Chester, MD 21619
    800 Abruzzi Dr, Chester, MD 21619
    /18

    Starting at $1,949 Per Month

    • 1 - 3 Beds

    800 Abruzzi Dr, Chester, MD 21619

    Make your new home on Kent Island at The Promenade Apartments and you will have found the ideal setting that combines the best of city and beach living. With easy access to Route 50 and just a short drive from Annapolis, Easton, and Centreville, adventure is always right around the corner.When you’re not exploring the surrounding area, at home you’ll enjoy premium interior finishes in

    The Promenade at Red Apple Town Center

    (443) 963-3568

    800 Abruzzi Dr, Chester, MD 21619
  • 6002 Bridgepointe Dr, Chester, MD 21619
    6002 Bridgepointe Dr, Chester, MD 21619
    6002 Bridgepointe Dr, Chester, MD 21619
    /6

    $2,500 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,586 Sq Ft
    • Townhouse for Rent

    6002 Bridgepointe Dr, Chester, MD 21619

    Coming soon. spacious 3 bedroom, 2 bath townhouse located in Bridge Pointe Townhouse subdivision. Convenient to Rt 50. Credit check and references required. Minimum credit score of 600. Pets case by case. Available June 16. Will be active Saturday, June 13th.

    Eddie Matthews Benson & Mangold, LLC

    6002 Bridgepointe Dr, Chester, MD 21619
  • 230 Switchgrass Way Unit 21, Chester, MD 21619
    230 Switchgrass Way Unit 21, Chester, MD 21619
    230 Switchgrass Way Unit 21, Chester, MD 21619
    /46

    $4,300 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft
    • Condo for Rent

    230 Switchgrass Way Unit 21, Chester, MD 21619

    As Summer 2026 arrives, there's no better time to enjoy everything this vibrant waterfront 55+ community has to offer—from mornings spent walking along the Chester River to afternoons at the infinity pool and evenings filled with live music, social events, and sunsets over the water. This like-new Severn model is one of the community's most desirable floorplans, offering more than 2,600 square

    Jennifer Thomas RE/MAX Executive

    230 Switchgrass Way Unit 21, Chester, MD 21619
  • 101 Dundee Ave Unit 202, Chester, MD 21619
    101 Dundee Ave Unit 202, Chester, MD 21619
    101 Dundee Ave Unit 202, Chester, MD 21619
    /12

    $1,400 Per Month

    • 1 Bed
    • 1 Bath
    • 3,596 Sq Ft
    • Condo for Rent

    101 Dundee Ave Unit 202, Chester, MD 21619

    1 bedroom 1 bath apartment, second floor with balcony. Freshley painted, new LVP flooring. Reserved parking for 1 vehicle, overflow parking for one other vehicle. Water & sewer, trash removal and parking included. Small pets under 35lbs welcomed on a case-by-case basis. Secure building.

    Cindy Jacobs Maryland Residential Management Co

    101 Dundee Ave Unit 202, Chester, MD 21619
  • 2201 Main St Unit 105, Chester, MD 21619
    2201 Main St Unit 105, Chester, MD 21619
    /2

    $1,950 Per Month

    • 2 Beds
    • 1.5 Baths
    • 1,200 Sq Ft
    • Townhouse for Rent

    2201 Main St Unit 105, Chester, MD 21619

    Spacious well maintained unit. Security entrance, close to shopping with easy access to Rt. 50 and easy distance to Easton or Annapolis. Large living area, large bedrooms, large kitchen. Use owner lease.

    Rodger Weese Weese Properties, LLC

    2201 Main St Unit 105, Chester, MD 21619
  • 137 Warbler Way, Chester, MD 21619
    137 Warbler Way, Chester, MD 21619
    137 Warbler Way, Chester, MD 21619
    /81

    $4,300 Per Month

    • 2 Beds
    • 2 Baths
    • 2,147 Sq Ft
    • House for Rent

    137 Warbler Way, Chester, MD 21619

    RARE RENTAL in sought- after water-oriented Four Seasons- Ready to "try-on" coveted 'Four Seasons'? Treat yourself to this STUNNING beauty- Boasting soaring ceilings, flooded with natural light, spacious, open-floor plan nearly 2200 SF, with generously-sized primary suite & spa-like bath with walk-in-closet, double sinks & walk-in-shower. 2nd bedroom & bath across home offers privacy for guests.

    Jennifer Chaney Chaney Homes, LLC

    137 Warbler Way, Chester, MD 21619
  • 2006 Stevens Dr, Chester, MD 21619
    2006 Stevens Dr, Chester, MD 21619
    2006 Stevens Dr, Chester, MD 21619
    /13

    $2,500 Per Month

    • 3 Beds
    • 1.5 Baths
    • 1,120 Sq Ft
    • House for Rent

    2006 Stevens Dr, Chester, MD 21619

    Fully renovated 3-bedroom, 1.5-bath home in a prime location just minutes from the Bay Bridge, perfect for enjoying spring and summer on the island. This home features a completely updated interior with a new kitchen, appliances, bathrooms, flooring, paint, and fixtures, offering a fresh, modern feel throughout. The open and airy layout is filled with natural light, creating a bright and inviting

    Jennifer Thomas RE/MAX Executive

    2006 Stevens Dr, Chester, MD 21619
Maryland Queen Anne's County Chester

Homes for Rent in Chester, MD

Why Live in Chester

Chester, MD, located on Kent Island between the Chester River and Chesapeake Bay, offers a blend of coastal charm and modern convenience. The area is known for its maritime atmosphere, with numerous marinas and waterfront views. Chester is 17 miles from Annapolis, home to the United States Naval Academy. Outdoor enthusiasts can enjoy Terrapin Nature Park's walking paths and tidal marshes, or the Cross Island Trail for hiking and cycling. Castle Marina provides opportunities for boating and fishing. Indoor fitness options include Club One Fitness and Aerobics. Housing in Chester ranges from ranch-style homes and colonials to New Traditional builds, with properties south of Highway 50 dating back to the mid-20th century and newer developments in the north. The area features a mix of single-family homes, condos, and townhouses, with some waterfront estates requiring additional flood insurance. Annual events like the Kent Island Crab Feast and the Annapolis Baygrass Music Festival foster community spirit. Shopping and dining are centered around Highway 50, with big-box stores like Safeway and Target, and bayside dining options in nearby Kent Narrows, including The Jetty and Bridges. Chester's schools are highly rated, with Bayside Elementary, Stevensville Middle, and Kent Island High all receiving commendable scores. Highway 50 is the main transportation route, connecting Chester to Annapolis, Baltimore, and Washington, D.C., while BWI International Airport is about 30 miles away.

Learn more about living in Chester

Frequently Asked Questions

How much does it cost to rent a home in Chester, MD?
The median rent for a home in Chester, MD is $2,225 per month, though prices vary by neighborhood, size, and property type. As of June 2026, condos tend to be the most affordable option while townhouses and single-family homes are currently more expensive.
How much do you need to make to afford rent in Chester, MD?
To comfortably afford the median rent in Chester, MD, a household needs to earn roughly $89,000 per year. This is based on the common guideline that households should spend no more than 30% of gross income on housing. Most landlords require monthly household income of at least 3x the monthly rent, and with a median rent of $2,225 per month in Chester, MD, renters typically need to show $6,675 per month in gross income to qualify. Actual affordability will vary depending on household debts, other living expenses, and overall budget.
Is it more affordable to rent or buy in Chester, MD?
In Chester, MD, the price-to-rent ratio is 24.4, which generally favors renting. This ratio divides the median home price by the annual median rent: below 15 typically favors buying, 15 to 20 is balanced, and above 20 typically favors renting. Your finances, how long you plan to stay, and costs like mortgage rates, taxes, and maintenance all factor into the decision.
What neighborhoods in Chester, MD are best for renting a home?
The best neighborhood for renting in Chester, MD depends on your priorities: commute, walkability, budget, and lifestyle all play a role. Popular areas for renting a home include Pendennis Mount, Cape Saint Claire, Victor Haven, Downtown Annapolis and Eastport, each with its own character and price range.

Rental Trends in Chester, MD

There are currently 8 homes available for rent in Chester, MD. The median rent is $2,225 per month, with single-family homes renting at $2,750, townhouses at $2,550 and condos at $1,950.

Rental Home Trends

Number of Homes for Rent
8
Median Rent
$2,225
Median Single Family Home Rent
$2,750
Median Townhouse Rent
$2,550
Median Condo Rent
$1,950
How to Rent a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group