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Chester, MD Homes for Rent

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  • 106 Blenny Ln, Chester, MD 21619
    106 Blenny Ln, Chester, MD 21619
    106 Blenny Ln, Chester, MD 21619
    /42

    $2,995 per month

    • 3 Beds
    • 4 Baths
    • 1,899 Sq Ft
    • Townhouse for Rent

    106 Blenny Ln, Chester, MD 21619

    Welcome to this beautifully updated 3-level interior townhome located in the highly sought-after Bayside community on Kent Island. This move-in ready home features 3 spacious bedrooms, 2 full bathrooms, and 2 half baths, offering both comfort and functionality across every level. The main living area showcases gleaming hardwood floors, a gas fireplace, and an open layout perfect for everyday

    Jose Matos Chaney Homes, LLC

    106 Blenny Ln, Chester, MD 21619
  • 113 Henry Stoupe Way, Chester, MD 21619
    113 Henry Stoupe Way, Chester, MD 21619
    113 Henry Stoupe Way, Chester, MD 21619
    /19

    $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
  • 226 Bentons Pleasure Rd, Chester, MD 21619
    226 Bentons Pleasure Rd, Chester, MD 21619
    226 Bentons Pleasure Rd, Chester, MD 21619
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    $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
  • 2626 Cecil Dr, Chester, MD 21619
    2626 Cecil Dr, Chester, MD 21619
    2626 Cecil Dr, Chester, MD 21619
    /10

    $2,500 per month

    • 3 Beds
    • 2.5 Baths
    • 1,272 Sq Ft
    • House for Rent

    2626 Cecil Dr, Chester, MD 21619

    Welcome to this charming home located in the quiet, established community of Harbor View in Chester. This well-maintained property features a bright and open floor plan with a cozy fireplace—perfect for relaxing evenings. The kitchen comes fully equipped with modern appliances. Enjoy the convenience of an attached garage and a spacious 0.34-acre lot with plenty of outdoor space. Situated just

    Kevin Waterman Coldwell Banker Waterman Realty

    2626 Cecil Dr, Chester, MD 21619
  • 2605 Harrington Rd, Chester, MD 21619
    2605 Harrington Rd, Chester, MD 21619
    2605 Harrington Rd, Chester, MD 21619
    /29

    $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. PROPERTY AVAILABLE

    Raj Mirani Taylor Properties

    2605 Harrington Rd, Chester, MD 21619
  • 907 Auckland Way, Chester, MD 21619
    907 Auckland Way, Chester, MD 21619
    907 Auckland Way, Chester, MD 21619
    /59

    $3,200 per month

    • 3 Beds
    • 3.5 Baths
    • 2,100 Sq Ft
    • Townhouse for Rent

    907 Auckland Way, Chester, MD 21619

    Showings begin Sunday! Rare waterview end-unit townhouse for rent on Kent Island. Located in Bayside, a sought-after waterfront community on Maryland’s Eastern Shore, this tucked-away property offers true Chesapeake Bay resort-style living. Residents enjoy a community pool with hot tub, tennis courts, lawn volleyball, scenic walking trails, and a renovated clubhouse with fitness center, kitchen,

    Jennifer Snead Long & Foster Real Estate, Inc.

    907 Auckland Way, Chester, MD 21619
  • 107 Dundee Ave Unit 201, Chester, MD 21619
    107 Dundee Ave Unit 201, Chester, MD 21619
    107 Dundee Ave Unit 201, Chester, MD 21619
    /16

    $1,750 per month

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

    107 Dundee Ave Unit 201, Chester, MD 21619

    1 bedroom 1 bath apartment 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 per month. Closet on balcony is mechanical room and not

    Cindy Jacobs Maryland Residential Management Co

    107 Dundee Ave Unit 201, Chester, MD 21619
  • 29D Queen Mary Ct, Chester, MD 21619
    29D Queen Mary Ct, Chester, MD 21619
    29D Queen Mary Ct, Chester, MD 21619
    /39

    $2,700 per month

    • 3 Beds
    • 2.5 Baths
    • 1,440 Sq Ft
    • Townhouse for Rent

    29D Queen Mary Ct, Chester, MD 21619

    Wonderful Queens Landing on Kent Island! Totally updated kitchen area with center island and bar stools! *Hardwood floors on main living area! Enclosed sun-room with beautiful views of the lake. Spacious living room with fireplace and built in book cases. Kitchen with Breakfast Bar. Main Bedroom, with Main Bath, also over looks the lake. *This town home is a must see in Queens Landing* Community

    Michael Roenigk Chaney Homes, LLC

    29D Queen Mary Ct, Chester, MD 21619
Maryland Queen Annes 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

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 Tyler Heights-Primrose Acres.
What are the most popular zip codes in Chester, MD for renters?
The most popular zip codes in Chester, MD for renters include 21619, 21666, 21409, 21403 and 21012.
How to Rent a Home

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