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Chester, MD Homes for Rent

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  • 8013 Bridgepointe Dr, Chester, MD 21619
    8013 Bridgepointe Dr, Chester, MD 21619
    8013 Bridgepointe Dr, Chester, MD 21619
    /17

    $2,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,285 Sq Ft
    • Condo for Rent

    8013 Bridgepointe Dr, Chester, MD 21619

    Welcome to your new home in Chester, MD! This charming property offers a comfortable living space in a welcoming community. Located conveniently nearby, you'll find fantastic restaurants perfect for enjoying meals out and socializing. Also convenient to Rt 50, golf and outlet shopping.Key property features include a large new deck that spans the length of the back of the house, central

    (443) 981-2425

    8013 Bridgepointe Dr, Chester, MD 21619
  • 6006 Bridgepointe Dr, Chester, MD 21619
    6006 Bridgepointe Dr, Chester, MD 21619
    6006 Bridgepointe Dr, Chester, MD 21619
    /25

    $2,600 Per Month

    • 2 Beds
    • 2 Baths
    • 1,232 Sq Ft
    • Condo for Rent

    6006 Bridgepointe Dr, Chester, MD 21619

    Suzanne Hitt Coldwell Banker Waterman Realty

    6006 Bridgepointe Dr, Chester, MD 21619
  • 112 Merganser Ct Unit 1112 Merganser Ct, Chester, MD 21619
    112 Merganser Ct Unit 1112 Merganser Ct, Chester, MD 21619
    112 Merganser Ct Unit 1112 Merganser Ct, Chester, MD 21619
    /28

    $2,100

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,069 Sq Ft
    • Condo for Rent

    112 Merganser Ct Unit 1112 Merganser Ct, Chester, MD 21619

    2 bedroom, 2 bath condo with cathedral ceilings, washer/dryer, walk-in closet, fireplace, balcony and upgraded kitchen cabinets. Includes clubhouse with gym, large community swimming pool with lifeguard, and tennis/pickleball court. Near the bay, boating, Cross Island walking/biking trail, restaurants, and 5 minutes to Bay Bridge. References and good credit necessary. Pets okay with additional

    112 Merganser Ct Unit 1112 Merganser Ct, 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
  • 2201 Main St Unit 105, Chester, MD 21619
    2201 Main St Unit 105, Chester, MD 21619
    2201 Main St Unit 105, Chester, MD 21619
    /12

    $1,950 Per Month

    • 2 Beds
    • 1.5 Baths
    • 1,200 Sq Ft
    • Chester Centre Apartments

    2201 Main St Unit 105, Chester, MD 21619

    2 bedroom, 1.5 bath townhouse style apartment on the 2nd and 3rd floors of the Chester Centre building. Approximately 1200 square feet. Secure entry door, ample parking, easy walk to restaurants.

    2201 Main St Unit 105, Chester, MD 21619
  • 1812 Main St Unit 202, Chester, MD 21619
    1812 Main St Unit 202, Chester, MD 21619
    1812 Main St Unit 202, Chester, MD 21619
    /32

    $1,650 Per Month

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

    1812 Main St Unit 202, Chester, MD 21619

    Modern, energy-efficient luxury apartment for lease offering 926 sq ft of thoughtfully designed living space. This oversized 1-bedroom, 1-bath unit stands apart from typical apartment living with an open, spacious layout and quality finishes throughout. Luxury vinyl flooring runs through the foyer, hallway, kitchen, dining, and family room. The well-appointed full-size kitchen features

    Jennifer Norfolk Coldwell Banker Waterman Realty

    1812 Main St Unit 202, Chester, MD 21619
  • 29D Queen Mary Ct, Chester, MD 21619
    29D Queen Mary Ct, Chester, MD 21619
    29D Queen Mary Ct, Chester, MD 21619
    /37

    $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
  • 11F Queen Elizabeth Ct, Chester, MD 21619
    11F Queen Elizabeth Ct, Chester, MD 21619
    11F Queen Elizabeth Ct, Chester, MD 21619
    /34

    $2,100 Per Month

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

    11F Queen Elizabeth Ct, Chester, MD 21619

    Here is your chance to live in one of Kent Island's favorite neighborhoods!! Nicely renovated waterfront condo features spectacular sunrises & moonlit evenings! Separate bedroom on waterside. Neutral decor and new glass top range and granite counter top in kitchen. Mirrored wall in family room makes the room seem larger and more open! New wood-look vinyl flooring, ceramic tile and new tub/shower

    Mary Stevens Long & Foster Real Estate, Inc.

    11F Queen Elizabeth Ct, 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
  • 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
  • 106 Blenny Ln, Chester, MD 21619
    106 Blenny Ln, Chester, MD 21619
    106 Blenny Ln, Chester, MD 21619
    /43

    $2,899 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
  • 107 Dundee Ave Unit 203, Chester, MD 21619
    107 Dundee Ave Unit 203, Chester, MD 21619
    107 Dundee Ave Unit 203, Chester, MD 21619
    /17

    $1,800 Per Month

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

    107 Dundee Ave Unit 203, 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 kitchen with an island, full size washer & dryers in unit. Water & sewer included. This is a NO SMOKING building. Pets under 35lbs welcome with pet rent. Closet on balcony is mechanical only, not for tenant use.

    Cindy Jacobs Maryland Residential Management Co

    107 Dundee Ave Unit 203, Chester, MD 21619
  • 312 Blenny Ln, Chester, MD 21619
    312 Blenny Ln, Chester, MD 21619
    312 Blenny Ln, Chester, MD 21619
    /48

    $3,150 Per Month

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

    312 Blenny Ln, Chester, MD 21619

    You don't want to miss the opportunity to enjoy Island Living in this maintenance free Pond View End Unit! Come enjoy Island Living in the Bayside Community. Offering Pond Views from every window in this sought after end unit home complete with beautiful landscaping. Relax on your spacious deck overlooking the pond complete with 2 fountains or invite family and friends to enjoy a cookout on your

    Judith Brown EXP Realty, LLC

    312 Blenny Ln, 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
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

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, Eastport, Victor Haven 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 21619, 21638, 21666, 21409 and 21403.

Rental Home Trends in Chester, MD

There are currently 14 homes available for rent in Chester, MD. The median rent is $2,500 per month, with single-family homes renting at $2,850, townhouses at $2,600 and condos at $2,000.

Rental Home Trends

Number of Homes for Rent
14
Median Rent
$2,500
Median Single Family Home Rent
$2,850
Median Townhouse Rent
$2,600
Median Condo Rent
$2,000
How to Rent a Home

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