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Chester, MD Homes for Rent

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  • 141 Switchgrass Way Unit 34, Chester, MD 21619
    141 Switchgrass Way Unit 34, Chester, MD 21619
    141 Switchgrass Way Unit 34, Chester, MD 21619
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    $3,800 per month

    • 3 Beds
    • 2.5 Baths
    • 2,600 Sq Ft
    • Condo for Rent

    141 Switchgrass Way Unit 34, Chester, MD 21619

    K Hovnanian's Four Seasons at Kent Island is an active 55+ community on Maryland's Chesapeake Bay, offering island resort-style and maintenance-free living at its finest! The Severn design is a spacious and airy 3 bedroom, 2.5 bath end-unit boasting an expansive open floor plan with over 2600 square feet of luxurious living space. This home features a lavish gourmet kitchen and dining area, a

    Ralph Kennedy RE/MAX Executive

    141 Switchgrass Way Unit 34, Chester, MD 21619
  • 137 Warbler Way, Chester, MD 21619
    137 Warbler Way, Chester, MD 21619
    137 Warbler Way, Chester, MD 21619
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    $4,300 per month

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

    137 Warbler Way, Chester, MD 21619

    Ready to "try-on" coveted 'Four Seasons'? Treat yourself to this STUNNING 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- easily used for 3rd

    Jennifer Chaney Chaney Homes, LLC

    137 Warbler Way, Chester, MD 21619
  • 1606 Howard Rd, Chester, MD 21619
    1606 Howard Rd, Chester, MD 21619
    1606 Howard Rd, Chester, MD 21619
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    $5,000 per month

    • 3 Beds
    • 2 Baths
    • 1,755 Sq Ft
    • House for Rent

    1606 Howard Rd, Chester, MD 21619

    Welcome to Crab Alley Bay, Chester, MDThis cherished waterfront home offers one of the most captivating settings on the Eastern Shore—perched on a point with sweeping 270-degree panoramic views of Crab Alley Bay. Resting on approximately three-quarters of an acre, the property is as peaceful and restorative as it is beautiful, providing a rare opportunity to enjoy true waterfront

    Lisa Barton Coldwell Banker Realty

    1606 Howard Rd, Chester, MD 21619
  • 242 Peregrine Dr, Chester, MD 21619
    242 Peregrine Dr, Chester, MD 21619
    242 Peregrine Dr, Chester, MD 21619
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    $4,500 per month

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

    242 Peregrine Dr, Chester, MD 21619

    PLEASE SEE MLS # MDQA2013106 FOR PHOTOS. 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

    Pamela Owens Anchor Group Realty, LLC

    242 Peregrine Dr, 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, Victor Haven, Cape Saint Claire, 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 21619, 21666, 21409, 21601 and 21403.
How to Rent a Home

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