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Chester, MD Homes for Rent

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  • 41A Queen Catherine Ct, Chester, MD 21619
    41A Queen Catherine Ct, Chester, MD 21619
    41A Queen Catherine Ct, Chester, MD 21619
    /8

    $1,400

    Total Monthly Price

    • 2 Beds
    • 4 Baths
    • 2,300 Sq Ft
    • Townhouse for Rent

    41A Queen Catherine Ct, Chester, MD 21619

    Two Rooms for rent for 1,400 each or 2800 for the whole house in a beautiful townhome in Chester Maryland.There is a pond outback with fountain. It is a 3 story end unit next to a lighthouse. Two bedroom house with two full private bathrooms on the third floor in each bedroom, on the second floor there's the kitchen, a deck, a living room, a rec room and 1/2 bathroom. In the basement, there

    41A Queen Catherine Ct, Chester, MD 21619
  • 800 Abruzzi Dr, Chester, MD 21619
    800 Abruzzi Dr, Chester, MD 21619
    800 Abruzzi Dr, Chester, MD 21619
    /20

    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 at Red Apple Town Center, 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

    The Promenade

    800 Abruzzi Dr, Chester, MD 21619
  • 1712 Main St, Chester, MD 21619
    1712 Main St, Chester, MD 21619
    1712 Main St, Chester, MD 21619
    /11

    $1,500 Per Month

    • Studio
    • 2 Baths
    • 875 Sq Ft
    • House for Rent

    1712 Main St, Chester, MD 21619

    Property Id: 2619180Office space available approximately 875 square feet. Features two separate offices plus common area, Two individual private bath rooms . This is a second floor office with outside entry but no elevator. A shared kitchenette is also available for your use. NO CAM nor utility charges. Building is well maintained and office staff available during the week to answer any

    1712 Main St, Chester, MD 21619
  • 3000 Herons Nest Way Unit 11, Chester, MD 21619
    3000 Herons Nest Way Unit 11, Chester, MD 21619
    3000 Herons Nest Way Unit 11, Chester, MD 21619
    /66

    $4,500 Per Month

    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft
    • Condo for Rent

    3000 Herons Nest Way Unit 11, Chester, MD 21619

    Highly sought after first-floor condo shows like a model home. Love Where You Live! Experience resort-style living that blends comfort, luxury, and convenience—just steps from the waterfront. Enjoy peaceful mornings without the disruption of construction nearby. Move-in ready and meticulously maintained, featuring numerous upgrades throughout. Step inside to an open, light-filled layout enhanced

    John Freeman Coldwell Banker Realty

    3000 Herons Nest Way Unit 11, Chester, MD 21619
  • 1910 Churchhill Ln Unit A, Chester, MD 21619
    1910 Churchhill Ln Unit A, Chester, MD 21619
    1910 Churchhill Ln Unit A, Chester, MD 21619
    /5

    $1,650 Per Month

    • 1 Bed
    • 1 Bath
    • 370 Sq Ft
    • House for Rent

    1910 Churchhill Ln Unit A, Chester, MD 21619

    Charming attached cottage with a completely separate rear entrance. Features 1 bedroom, 1 full bath, and an open kitchen/living space combo. Enjoy a large yard with mature shade trees and a tranquil setting. Conveniently located near Route 50 with easy access to shopping, dining, and more. Rent includes sewer and trash pickup. Approximately 370 square feet. Washer and dryer are included. On

    Lisa Magnus Clark & Co Realty, LLC

    1910 Churchhill Ln Unit A, Chester, MD 21619
  • 45 Queen Neva Ct Unit B, Chester, MD 21619
    45 Queen Neva Ct Unit B, Chester, MD 21619
    45 Queen Neva Ct Unit B, Chester, MD 21619
    /43

    $2,300 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,312 Sq Ft
    • Townhouse for Rent

    45 Queen Neva Ct Unit B, Chester, MD 21619

    Discover the charm of this exquisite 2-bedroom, 2.5-bathroom townhouse nestled in the desirable Queens Landing community. Built in 1995, this Spanish-style gem boasts an open floor plan that seamlessly connects the living and dining areas, perfect for entertaining or cozy nights in. The interior features plush carpeting and ample natural light, creating a warm and inviting atmosphere. The

    Jackie Ball Daley Northrop Realty

    45 Queen Neva Ct Unit B, Chester, MD 21619
  • 101 Chester Village Unit 203, Chester, MD 21619
    101 Chester Village Unit 203, Chester, MD 21619
    101 Chester Village Unit 203, Chester, MD 21619
    /4

    $1,200 Per Month

    • 1 Bed
    • 1 Bath
    • 450 Sq Ft
    • Condo for Rent

    101 Chester Village Unit 203, Chester, MD 21619

    Recently renovated second floor apartment located off of Main Street in Chester. Off street parking and laundry on site. Located close to shopping, restaurants and KI trail.

    Lisa Lynch Keller Williams Realty

    101 Chester Village Unit 203, 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

    AVAILABLE FOR RENT JULY 1ST-- 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

    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 $2,400 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 $96,000 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 $2,400 per month in Chester, MD, renters typically need to show $7,200 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 22.9, 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 9 homes available for rent in Chester, MD. The median rent is $2,400 per month, with single-family homes renting at $2,865, townhouses at $2,500 and condos at $1,975.

Rental Home Trends

Number of Homes for Rent
9
Median Rent
$2,400
Median Single Family Home Rent
$2,865
Median Townhouse Rent
$2,500
Median Condo Rent
$1,975
How to Rent a Home

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