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Chester, MD Homes for Rent

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  • 1540 Postal Rd Unit 108, Chester, MD 21619
    1540 Postal Rd Unit 108, Chester, MD 21619
    /2

    $1,650 per month

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

    1540 Postal Rd Unit 108, Chester, MD 21619

    Property Id: 1348539SENIOR APTS 62+ Two-bedroom, one bath on first flooravailable to see July 9th. Appliances included. Small petsallowed. Close to all your needs. Call today .

    1540 Postal Rd Unit 108, Chester, MD 21619
  • 1018 Dundee Ct, Chester, MD 21619
    1018 Dundee Ct, Chester, MD 21619
    1018 Dundee Ct, Chester, MD 21619
    /29

    $2,400 per month

    • 3 Beds
    • 2.5 Baths
    • 1,400 Sq Ft
    • Townhouse for Rent

    1018 Dundee Ct, Chester, MD 21619

    1018 Dundee Court is the perfect townhouse located in the heart of Kent Island. As you enter the home, the spacious living room greets you, and leads to the kitchen and separate dining room. Off the dining room is the perfect sized deck to enjoy summer weather. The main level also features a half bath and laundry room. Additional outdoor storage room is located off on deck. Upstairs boasts 3

    Annie Eaton Coldwell Banker Realty

    1018 Dundee Ct, Chester, MD 21619
  • 137 Warbler Way, CHESTER, MD 21619
    137 Warbler Way, CHESTER, MD 21619
    /2

    $4,300 per month

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

    137 Warbler Way, CHESTER, MD 21619

    Welcome to this charming single-family home in the heart of coveted Four Seasons. Built in 2024, this delightful '55 or better' residence offers two bedrooms and two bathrooms within 2,147 square feet of living space, perfect for anyone seeking comfort and convenience.Key property features include a modern, open design with soaring ceilings ranging 10-13'- throughout the home! Enjoy the

    137 Warbler Way, CHESTER, MD 21619
  • 2201 Main St Unit 105, Chester, MD 21619
    2201 Main St Unit 105, Chester, MD 21619
    /2

    $1,890 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
  • 101 Chester Village, Chester, MD 21619
    101 Chester Village, Chester, MD 21619
    /2

    $1,200 per month

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

    101 Chester Village, Chester, MD 21619

    Completely renovated one bedroom one bath second floor apartment in Chester. New appliances, cabinets and countertops - granite and quartz. Totally renovated bathroom with new cabinets, sink, shower and fixtures. New engineered wood flooring. Laundry on site. Off street paved parking lot. Conveniently located near shopping, restaurants and marinas.

    101 Chester Village, Chester, MD 21619
  • 1606 Postal Rd Unit A, Chester, MD 21619
    1606 Postal Rd Unit A, Chester, MD 21619
    1606 Postal Rd Unit A, Chester, MD 21619
    /18

    $1,950 per month

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

    1606 Postal Rd Unit A, Chester, MD 21619

    Apartment A- One level 2 bedroom, 2 bath unit, Renovated in 2022 with new baths, flooring, paint, doors, some windows, HVAC, and dryer. Lots of parking. Has a deck off the parking area access to the unit. Easy access to Rt 50, close to shopping, restaurants. Trash, parking, grounds maintenance and water sewer included in rent.

    Cindy Jacobs Maryland Residential Management Co

    1606 Postal Rd Unit A, Chester, MD 21619
  • 5H Queen Victoria Way, Chester, MD 21619
    5H Queen Victoria Way, Chester, MD 21619
    5H Queen Victoria Way, Chester, MD 21619
    /26

    $2,800 per month

    • 2 Beds
    • 1 Bath
    • 1,380 Sq Ft
    • Townhouse for Rent

    5H Queen Victoria Way, Chester, MD 21619

    Welcome to your dream coastal escape! This beautifully situated waterfront townhome on Kent Island offers stunning views of Castle Marina and is just steps from two popular waterfront restaurants. Enjoy serene mornings and breezy evenings from your private patio, or hop onto your boat in the marina and venture into the scenic Chester River.Residents enjoy top-notch community amenities

    Darlene Winegardner RE/MAX Executive

    5H Queen Victoria Way, Chester, MD 21619
  • 107 Dundee Ave Unit 102, Chester, MD 21619
    107 Dundee Ave Unit 102, Chester, MD 21619
    107 Dundee Ave Unit 102, Chester, MD 21619
    /16

    $1,750 per month

    • 1 Bed
    • 1 Bath
    • 6,338 Sq Ft
    • Condo for Rent

    107 Dundee Ave Unit 102, Chester, MD 21619

    1 bedroom 1 bath apartments in Chester. Close to everything Kent Island. Secure building, keyless entry, 1 parking space per unit with plenty of overflow for one additional per unit. Large kitchens, full size washer & dryers in each unit. Water & sewer included. This is a NO SMOKING building. Pets under 35lbs welcome with pet rent of $50 monthly

    Cindy Jacobs Maryland Residential Management Co

    107 Dundee Ave Unit 102, Chester, MD 21619
  • 113 Henry Stoupe Way, Chester, MD 21619
    113 Henry Stoupe Way, Chester, MD 21619
    113 Henry Stoupe Way, Chester, MD 21619
    /10

    $3,500 per month

    • 3 Beds
    • 2.5 Baths
    • 1,844 Sq Ft
    • House for Rent

    113 Henry Stoupe Way, Chester, MD 21619

    The "Gibson's Grant" Waterfront Community has a new Rental Home available! They don't come on the market that often in this desired neighborhood... so don't delay! This Stunning 3 BR, 2.5BA, single family home is ready for you to move right in! Full of upgrades to include a Custom Stone Fireplace Surround and Mantel, Hardwood floors, Granite Countertops, SS Appliances, Beautiful Tiled Backsplash,

    Pamela Ackermann-Doll RE/MAX Executive

    113 Henry Stoupe Way, Chester, MD 21619
  • 124 Nighthawk Dr, Chester, MD 21619
    124 Nighthawk Dr, Chester, MD 21619
    124 Nighthawk Dr, Chester, MD 21619
    /54

    $4,300 per month

    • 2 Beds
    • 2.5 Baths
    • 2,014 Sq Ft
    • House for Rent

    124 Nighthawk Dr, Chester, MD 21619

    Beautiful Award-Winning 55+ One-Level living — 2-bedroom, 2.5-bath single family home in the desirable Four Seasons at Kent Island community. Just minutes from the Bay Bridge, you will not want to miss this home, which offers an open layout, expertly appointed details, modern finishes, ensuite baths, and an expansive patio perfect for relaxing, entertaining or watching the wildlife at the pond.

    Melanie Wood Berkshire Hathaway HomeServices PenFed Realty

    124 Nighthawk Dr, Chester, MD 21619
  • 242 Peregrine Dr, Chester, MD 21619
    242 Peregrine Dr, Chester, MD 21619
    /2

    $4,500 per month

    • 4 Beds
    • 3 Baths
    • 3,151 Sq Ft
    • House for Rent

    242 Peregrine Dr, Chester, MD 21619

    Introducing the Simone – Where Modern Comfort Meets Farmhouse Charm. This 6 month old Simone offers the perfect blend of open-concept living and timeless Farmhouse style with 4 spacious bedrooms, 3 full baths, and a 2-car garage, this home is designed with both functionality and flair. Step inside to find stylish engineered wood flooring flowing through the foyer, hallways, home office, great

    Pamela Owens Anchor Group Realty, LLC

    242 Peregrine Dr, Chester, MD 21619
  • 218 Switchgrass Way Unit 42, Chester, MD 21619
    218 Switchgrass Way Unit 42, Chester, MD 21619
    218 Switchgrass Way Unit 42, Chester, MD 21619
    /55

    $5,000 per month

    • 2 Beds
    • 2.5 Baths
    • Condo for Rent

    218 Switchgrass Way Unit 42, Chester, MD 21619

    Experience luxurious, maintenance-free living at K. Hovnanian’s Four Seasons at Kent Island—an active 55+ community on Maryland’s Eastern Shore. This 2-bedroom, 2.5-bath penthouse condo offers sweeping views of the Chester River and refined coastal living. The open floor plan features a gourmet kitchen with quartz countertops, premium appliances, and a large center island, flowing into a

    Courtney Chipouras TTR Sotheby's International Realty

    218 Switchgrass Way Unit 42, Chester, MD 21619
  • 137 Warbler Way, Stevensville, MD 21666
    137 Warbler Way, Stevensville, MD 21666
    137 Warbler Way, Stevensville, MD 21666
    /81

    $3,850 per month

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

    137 Warbler Way, Stevensville, MD 21666

    No waiting on the builder here! Treat yourself to this STUNNING move-in-ready Four Seasons 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. Custom barn doors open to bonus space-

    Jennifer Chaney Chaney Homes, LLC

    137 Warbler Way, Stevensville, MD 21666
Maryland Chester

Homes for Rent in Chester, MD

Why Live in Chester

Chester features a diverse housing market with single-family homes, condos, and townhouses. The neighborhood includes ranch-style homes, colonials, and New Traditional builds. Properties south of Highway 50 date back to the mid-to-late 20th century, while newer communities in the northern sector have been developed over the past decade. Chester's parks and recreational activities are abundant, with Terrapin Nature Park offering walking paths and Chesapeake Bay views, and the Cross Island Trail providing a paved walkway for hikers and cyclists. Castle Marina is a hub for boating activities, and Club One Fitness and Aerobics offers gym facilities and an aquatic center. Shopping and dining are concentrated in plazas off Highway 50, with big-box stores like Safeway, Walgreens, and Target, and a variety of restaurants ranging from fast food to local favorites. Notable dining spots include The Jetty, Bridges, and Fisherman’s Inn in nearby Kent Narrows. Annual events such as the Kent Island Day parade and the Annapolis Baygrass Music Festival bring the community together. Highway 50 is the main thoroughfare, connecting Chester to Annapolis, 17 miles away, and the Chesapeake Bay Bridge provides access to Baltimore and Washington, D.C. Public transportation is available via Queen Anne’s County buses, and BWI International Airport is about 30 miles away. Schools in Chester are highly rated, with Bayside Elementary, Stevensville Middle, and Kent Island High all receiving strong ratings.
Learn more about living in Chester

Frequently Asked Questions

What are the most popular neighborhoods in Chester, MD for renters?
The most popular neighborhoods in Chester, MD for renters are Pendennis Mount, Cape Saint Claire, Victor Haven, Eastport and Downtown Annapolis.
What are the most popular zip codes in Chester, MD for renters?
The most popular zip codes in Chester, MD for renters include 21060, 21403, 21225, 21601 and 21122.
How to Rent a Home

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