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Newest Homes for Rent in Chester, MD

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  • 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
  • 111 Marshgrass Way Unit 22, Chester, MD 21619
    111 Marshgrass Way Unit 22, Chester, MD 21619
    111 Marshgrass Way Unit 22, Chester, MD 21619
    /102

    $3,600 Per Month

    • 2 Beds
    • 2.5 Baths
    • Condo for Rent

    111 Marshgrass Way Unit 22, Chester, MD 21619

    Your dream retreat awaits in this stunning luxury condo, where modern elegance meets breathtaking natural beauty. Total Turnkey! This exquisite residence features two spacious bedrooms, each with its own en-suite bath, and an additional half bath for guests. The thoughtfully designed office boasts custom built-in cabinets, providing both functionality and style.--Step into the heart of the home,

    Sharon Blaszczak Long & Foster Real Estate, Inc.

    111 Marshgrass Way Unit 22, 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
  • 2006 Stevens Dr, Chester, MD 21619
    2006 Stevens Dr, Chester, MD 21619
    2006 Stevens Dr, Chester, MD 21619
    /12

    $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
  • 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
  • 2605 Harrington Rd, Chester, MD 21619
    2605 Harrington Rd, Chester, MD 21619
    2605 Harrington Rd, Chester, MD 21619
    /27

    $2,950 Per Month

    • 4 Beds
    • 2.5 Baths
    • 1,852 Sq Ft
    • House for Rent

    2605 Harrington Rd, Chester, MD 21619

    Beautiful, four-bedroom, ranch-style home on level lot with spacious, fenced backyard. Kitchen has stainless steel appliances and granite counters/island. Hardwood floors. Energy efficiency improvements include a fully encapsulated, insulated crawlspace and R49 attic insulation. Quiet street. One small dog considered on case-by-case-basis, additional fee and deposit will apply. AVAILABLE JUNE 1,

    Raj Mirani Taylor Properties

    2605 Harrington Rd, Chester, MD 21619
  • 1540 Postal Rd Unit 210, Chester, MD 21619
    1540 Postal Rd Unit 210, Chester, MD 21619
    /2

    $1,950 Per Month

    • 2 Beds
    • 1 Bath
    • 850 Sq Ft
    • Condo for Rent

    1540 Postal Rd Unit 210, Chester, MD 21619

    Property Id: 2256460SENIOR APTS 62+ AT VILLAGE AT CHESTER. ALL APTS ARE TWO BR, ONE BA. ALL APPLIANCES INCLUDED. PETS ALLOWED. STORAGE SPACE COMES WITH LEASE. ONE YEAR LEASE. ELECTRIC AND CABLE ARE TENANTS BILLS. CLOSE TO ALL YOUR NEEDS. AVAILABLE 06/01/2026.CALL TODAY TO ANSWER ANY QUESTIONS YOU HAVE.BLYTHE LARRIMORE OSM

    (443) 569-4059

    1540 Postal Rd Unit 210, Chester, MD 21619
Maryland Queen Anne's County Chester

Newest Homes for Rent in Chester, MD

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 $1,950 per month, though prices vary by neighborhood, size, and property type. As of May 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 $78,000 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 $1,950 per month in Chester, MD, renters typically need to show $5,850 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 27.6, 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 Home Trends in Chester, MD

There are currently 7 homes available for rent in Chester, MD. The median rent is $1,950 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
7
Median Rent
$1,950
Median Single Family Home Rent
$2,750
Median Townhouse Rent
$2,550
Median Condo Rent
$1,950
How to Rent a Home

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