14

Chester, MD Homes for Rent

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  • /49

    $4,200 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft
    • Condo for Rent

    4000 Herons Nest Way Unit 42, Chester, MD 21619

    Four Seasons @ Kent Island 55+ -- FULLY FURNISHED, LUXURY PENTHOUSE RENTAL, TURN-KEY, JUST BRING YOUR CLOTHES -- Fabulous Penthouse/4th Floor Unit, Elevator Building with Private Garage + Driveway Parking & Keyed Storage Closet. Fully Furnished Chester Model, 1900 sf, 2 Bedroom + Den/Office & 2.5 Baths. Balcony Access From Living Room + Primary Bedroom. This is the DREAM! Includes all Furnishings

    Agent Photo

    Carol Tinnin

    RE/MAX Leading Edge

    4000 Herons Nest Way Unit 42, Chester, MD 21619
  • /2

    $1,750 Per Month

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

    1540 Postal Rd Unit 107, Chester, MD 21619

    Property Id: 2841646 Great location to fit all your needs. Restaurants, shopping, parks and the Bay are close. Great spot to hang your hat! Call today!

    1540 Postal Rd Unit 107, Chester, MD 21619
  • /53

    $4,000 Per Month

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

    190 Harrier Way Unit 24, Chester, MD 21619

    Four Seasons @ Kent Island - A Premiere 55+ Community - Luxury, Upscale Rental Offered as Rent OR Rent with Option to Buy in Resort-Like Community - Largest Model Available, Severn Model, 2600sf, 2nd Floor End Unit, Elevator Building + Private Garage + Private Driveway + Bonus Conditioned, Lobby Level Storage Closet. Features 3 Bedrooms, 2.5 Baths, Unfurnished, Tons of Closet Space, Bright End

    Agent Photo

    Carol Tinnin

    RE/MAX Leading Edge

    190 Harrier Way Unit 24, 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: 2256460 SENIOR 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 10/1/2026. CALL TODAY TO ANSWER ANY QUESTIONS YOU HAVE. BLYTHE LARRIMORE OSM

    1540 Postal Rd Unit 210, Chester, MD 21619
  • /9

    $2,600 Per Month

    • 4 Beds
    • 2.5 Baths
    • 1,840 Sq Ft
    • House for Rent

    107 Chessie Ct, Chester, MD 21619

    Nestled in the charming Clayborne Woods neighborhood, this delightful 4-bedroom, 2.5-bathroom Colonial home offers a perfect blend of comfort and style. With 1,840 sq. ft. of living space, the interior features plush carpeting, ceiling fans, and a spacious combination kitchen/dining area, ideal for gatherings. Enjoy the convenience of modern appliances, including a built-in microwave, dishwasher,

    Kevin Waterman Coldwell Banker Waterman Realty

    107 Chessie Ct, Chester, MD 21619
  • /16

    $2,000 Per Month

    • 2 Beds
    • 1 Bath
    • 950 Sq Ft
    • Townhouse for Rent

    321 Piney Narrows Rd Unit 1, Chester, MD 21619

    Everything Is brand new! This unique little apartment has been freshly created inside of a building right near a marina. Enjoy all that the Kent Island lifestyle has to offer. You are close to everything. This unit is offered furnished or not-your choice. Check out this bright, cheerful and newly renovated unit. Six month lease available for $2400/mo. This unit is also being offered as a

    Terri Gable Chesapeake Real Estate Associates, LLC

    321 Piney Narrows Rd Unit 1, Chester, MD 21619
  • /13

    $2,300 Per Month

    • 2 Beds
    • 1.5 Baths
    • 1,010 Sq Ft
    • Condo for Rent

    26 Queen Anne Way, Chester, MD 21619

    Check the disclosures for application procedures. Discover the charm of this delightful unit in the serene Queens Landing community. This inviting 2-bedroom, 1.5-bathroom apartment offers a perfect blend of comfort and convenience, making it an ideal place to call home. Step inside to find a spacious layout adorned with Mediterranean architectural style, featuring warm stucco finishes that create

    Jackie Ball Daley Northrop Realty

    26 Queen Anne Way, Chester, MD 21619
  • /17

    $2,200 Per Month

    • 4 Beds
    • 2 Baths
    • 5,128 Sq Ft
    • House for Rent

    1606 Postal Rd Unit C, Chester, MD 21619

    Apartment #C-Upstairs all on one level 4-bedroom, 2 bath unit, just painted and new LVP flooring & carpet added. Plenty of parking in building lot. Easy access to Rt 50, close to shopping, restaurants. Trash, parking, grounds maintenance and water sewer included in rent. One pet under 35lbs allowed with pet rent.

    Cindy Jacobs Maryland Residential Management Co

    1606 Postal Rd Unit C, Chester, MD 21619
  • /66

    $3,950 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
  • /35

    $3,000 Per Month

    • 2 Beds
    • 1 Bath
    • 645 Sq Ft
    • House for Rent

    215 Parks Rd, Chester, MD 21619

    Craving a WATERFRONT rental with pier, 15,000 lb boat lift, jet-ski lift, nearly 200 feet of shoreline, & sandy beach area on .4 acres just 5 mins from Bay Bridge? Welcome home! Enjoy this 6-Month WATERFRONT playground! Nearly 200' of shoreline with Private, sandy beach, 120' Pier with Boat Lift AND Jet-ski lift, panoramic views of coveted Cox Creek. With generous water depth, ideal location with

    Jennifer Chaney Chaney Homes, LLC

    215 Parks Rd, Chester, MD 21619
  • /44

    $4,500 Per Month

    • 5 Beds
    • 4.5 Baths
    • 3,225 Sq Ft
    • House for Rent

    215 Kingfisher Ln, Chester, MD 21619

    Try Before You Buy in Four Seasons at Kent Island! Experience the resort-style lifestyle of one of Kent Island’s most sought-after 55+ communities before making a purchase commitment.This nearly new Tuscaloosa model offers 5 bedrooms, 4.5 baths, a bright open floor plan, premium Café appliances, custom closets and window treatments, an oversized garage, and peekaboo Chester River views from

    Jennifer Thomas RE/MAX Executive

    215 Kingfisher Ln, Chester, MD 21619
  • /12

    $2,200 Per Month

    • 3 Beds
    • 1.5 Baths
    • 19,780 Sq Ft
    • House for Rent

    2201 Main St Unit 104, Chester, MD 21619

    Very spacious unit with large living area, large eat-in kitchen with walk-in pantry and, large bedrooms. Unit is a two story townhouse style on the 2nd and 3rd story of the building. Laundry on bedroom level. Ample closets, covered deck and security entrance. All new carpeting and paint.

    Rodger Weese Weese Properties, LLC

    2201 Main St Unit 104, Chester, MD 21619
  • /27

    $2,700 Per Month

    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft
    • House for Rent

    1340 Queen Anne Dr, Chester, MD 21619

    Discover the charm of this fully updated ranch in a serene, water-privileged community! With a spacious yard and an inviting open floor plan, this home features a stunning new kitchen complete with a large white granite island, sleek white cabinets, and stainless steel appliances. Sunlight floods the dining area through new sliding doors, while the generous living room is accented with stylish

    Darlene Winegardner RE/MAX Executive

    1340 Queen Anne Dr, Chester, MD 21619
  • /36

    $2,500 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,680 Sq Ft
    • Townhouse for Rent

    9 Queen Victoria Way, Chester, MD 21619

    Come see this freshly renovated waterview unit in Queens Landing! More photos to come, kitchen and bathrooms are being renovated. Enjoy Chester River views from all angles! The spacious first floor with a half bath has plenty of room for living, dining and whatever else you desire. The upper level features two bedrooms each with their own waterview balcony and full bathroom (one in the hall and

    Annie Eaton Coldwell Banker Realty

    9 Queen Victoria Way, Chester, MD 21619

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.

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 September 2026, condos tend to be the most affordable option while single-family homes and townhouses 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 24.0, 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

Number of Homes for Rent
14
Median Rent
$2,400
Median Single Family Home Rent
$2,500
Median Townhouse Rent
$2,550
Median Condo Rent
$2,000
How to Rent a Home