16

Chester, MD Homes for Rent

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  • /34

    $2,500 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,720 Sq Ft
    • Townhouse for Rent

    45D Queen Neva Ct, Chester, MD 21619

    Queen's Landing - Spacious Floor Plan with Rare1st Floor Master Bedroom with En Suite Full Bath and Walk-In Closet + 2 Additional Large Bedrooms on Upper-Level w Hall Full Bath + Large Hall Walk-In Closet. Large Rear Living Room/Dining Room Combo with Corner Gas Fireplace and Sliding Glass Doors to Patio. w View of Pond. Abundant Storage with Stylish Two-Sided Kitchen Cabinets with Pass Thru to

    Agent Photo

    Carol Tinnin

    RE/MAX Leading Edge

    (410) 709-7190

    45D Queen Neva Ct, 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: 2256460SENIOR 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 06/01/2026.CALL TODAY TO ANSWER ANY QUESTIONS YOU HAVE.BLYTHE LARRIMORE OSM

    (443) 569-4059

    1540 Postal Rd Unit 210, 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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /102

    $3,600 Per Month

    • 2 Beds
    • 2.5 Baths
    • Condo for Rent

    111 Marshgrass Way Unit 22, Chester, MD 21619

    Your dream retreat awaits in this stunning luxury condo, where modern elegance meets breathtaking natural beauty. Total Turnkey! This exquisite residence features two spacious bedrooms, each with its own en-suite bath, and an additional half bath for guests. The thoughtfully designed office boasts custom built-in cabinets, providing both functionality and style.--Step into the heart of the home,

    Sharon Blaszczak Long & Foster Real Estate, Inc.

    111 Marshgrass Way Unit 22, 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
  • /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
  • /40

    $2,600 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,747 Sq Ft
    • Townhouse for Rent

    400 Schooner Way, Chester, MD 21619

    **Live the Island Lifestyle**Bayside Town Home w/3 Levels**2 BR possible 3rd on Lower Level**Garage Parking**Looks out over Pond**Community Offers, Swimming Pool, Tennis Courts, Exercise Room**Close to Route 50 for Easy Access**$75.00 per Adult Processing Fee**Walk to Restaurants**

    Deborah Savoie Long & Foster Real Estate, Inc.

    400 Schooner Way, 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
  • /13

    $2,300 Per Month

    • 2 Beds
    • 1 Bath
    • 1,018 Sq Ft
    • House for Rent

    117 Goodhand Creek Rd, Chester, MD 21619

    Well maintained 2BR/1BA rancher offering convenient one-level living in Chester. Features include a spacious kitchen, separate dining room, and comfortable living room. Enclosed front porch can be used as a home office, sitting room, or flex space. Huge separate laundry room adds extra functionality. Situated on approximately 0.5 acres with a storage shed for additional storage. Close to

    Lisa Magnus Clark & Co Realty, LLC

    117 Goodhand Creek Rd, 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
  • /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

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

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, Downtown Annapolis, Victor Haven and Eastport.
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, 21638, 21409 and 21403.

Rental Home Trends in Chester, MD

Rental Home Trends

Number of Homes for Rent
16
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