15

Newest Homes for Rent in Chester, MD

Section Image
  • 111 Marshgrass Way Unit 22, Chester, MD 21619
    111 Marshgrass Way Unit 22, Chester, MD 21619
    111 Marshgrass Way Unit 22, 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
  • 400 Schooner Way, Chester, MD 21619
    400 Schooner Way, Chester, MD 21619
    400 Schooner Way, 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 1540 Postal Rd Unit 210, Chester, MD 21619
    1540 Postal Rd Unit 210, 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
Maryland Queen Anne's County Chester

Newest Homes for Rent in Chester, MD

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

There are currently 15 homes available for rent in Chester, MD. The median rent is $2,300 per month, with single-family homes renting at $2,850, townhouses at $2,600 and condos at $1,975.

Rental Home Trends

Number of Homes for Rent
15
Median Rent
$2,300
Median Single Family Home Rent
$2,850
Median Townhouse Rent
$2,600
Median Condo Rent
$1,975
How to Rent a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group