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Chester, MD Homes for Rent

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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

    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
  • /27

    $3,200 per month

    • 3 Beds
    • 2 Baths
    • 1,890 Sq Ft
    • House for Rent

    203 Anchor Ln, Chester, MD 21619

    Staged and re-freshed you'll wonder why you didn't scoop this one up earlier! This adorable rancher has the traditional 3 bedrooms and 2 baths and so much more including a large dining area, kitchen with breakfast bar that flows into a large living room anchored by a beautiful brick fireplace. PLUS a large addition offers a second living space with wood stove that overlooks the private, fenced

    Tricia Wilson Wilson Realty & Staging LLC

    203 Anchor Ln, 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
  • /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
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    $3,400 per month

    • 3 Beds
    • 3 Baths
    • 1,786 Sq Ft
    • House for Rent

    1614 Calvert Rd, Chester, MD 21619

    Located in the coveted water access community of Marling Farms in Chester (o Kent Island), this beautifully updated split level home has so much to offer including gorgeous water views from the living room, multiple livings spaces, huge kitchen with center island and a total of 3 beds and 3 full baths. Large deck off the dining room is perfect for entertaining or relaxing. Storage shed, too.

    1614 Calvert Rd, Chester, MD 21619
  • /13

    $2,395 per month

    • 4 Beds
    • 2.5 Baths
    • 1,586 Sq Ft
    • Townhouse for Rent

    6002 Bridgepointe Dr, Chester, MD 21619

    Discover this great rental opportunity on Kent Island! This spacious unit offers 3 bedrooms plus a flexible upstairs room perfect for a 4th bedroom or office. Enjoy the outdoors on your rear deck. Coming July 1st with fresh paint and new flooring throughout!

    Kevin Waterman Coldwell Banker Waterman Realty

    6002 Bridgepointe Dr, Chester, MD 21619
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    $2,700 per month

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

    31K Queen Anne Way, Chester, MD 21619

    Available July 1st - Gorgeous End Unit 2 bedroom, 2 bath with a large loft and high ceilings. This is a great home with lots of natural light and 3 patio areas. The 2nd floor offer a large loft, 2nd bedroom and full bath along with a balcony with water views. The views are incredible with the lake and fountain just a few steps from the back sliding glass door. The Queens Landing community is

    Terri Murray RE/MAX Executive

    31K Queen Anne Way, Chester, MD 21619
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    $4,500 per month

    • 3 Beds
    • 3.5 Baths
    • 3,400 Sq Ft
    • House for Rent

    235 Bayberry Dr, Chester, MD 21619

    Experience Kent Island living at its finest in this upgraded luxurious San Sebastian model in the prestigious Four Seasons community. Featuring an open floor plan with 10’ ceilings, designer finishes, newly renovated enclosed four-season porch and patio overlooking a gorgeous premium lot, this residence provides an ideal setting for both entertaining and everyday comfort. Arriving home, manicured

    Ralph Kennedy RE/MAX Executive

    235 Bayberry 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
  • /15

    $2,100 per month

    • 2 Beds
    • 2 Baths
    • 1,050 Sq Ft
    • Condo for Rent

    102 Teal Ct Unit A, Chester, MD 21619

    Move-in-ready 2 bed/2 bath condo on Kent Island in the conveniently located, water-oriented Bayside community. This is a 1st floor unit. Washer/dryer included. The resort-like community is beautifully landscaped and includes a swimming pool, hot tub, tennis courts, clubhouse and fitness center. Pets considered case-by-case. For boaters, Castle Harbor Marina is less than 1 block from this unit.

    Branden Schroeder GybeSet Homes

    102 Teal Ct Unit A, 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
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    $4,300 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

Why Live in Chester

Sandwiched between the Chester River and Chesapeake Bay in the heart of Kent Island, the Chester area comprises residential suburbs with close proximity to Highway 50. “It is known for its maritime feel—endless views of water, marinas and local establishments, lining the shoreline,” says Jennifer Heilman, the marketing manager for K. Hovnanian Homes. The area also sits 17 miles from Annapolis, Maryland’s capital city and the home of the United States Naval Academy. With access to both nature and modern conveniences, Chester caters to the laid-b ...

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, Eastport, Cape Saint Claire 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 21060, 21122, 21403, 21225 and 21601.
How to Rent a Home