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Chester, MD Townhomes for Sale

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  • 54A Queen Caroline Ct, Chester, MD 21619
    54A Queen Caroline Ct, Chester, MD 21619
    54A Queen Caroline Ct, Chester, MD 21619
    /43

    $450,000

    • 2 Beds
    • 2.5 Baths
    • 1,280 Sq Ft

    54A Queen Caroline Ct, Chester, MD 21619

    OPEN HOUSE, Saturday, August 2, from 11 am to 12 pm...Price Improvement...End Unit in Sought-After Queens Landing – A Waterfront Lifestyle Awaits!Don’t miss this spacious end unit in the highly desirable Queens Landing community! Featuring two primary bedroom suites with private baths, this home offers the perfect blend of comfort and functionality. The expansive kitchen is a chef’s

    Darlene Winegardner RE/MAX Executive

    54A Queen Caroline Ct, Chester, MD 21619
  • 9B Queen Victoria Way, Chester, MD 21619
    9B Queen Victoria Way, Chester, MD 21619
    9B Queen Victoria Way, Chester, MD 21619
    /48

    $475,000

    • 3 Beds
    • 2.5 Baths
    • 1,680 Sq Ft

    9B Queen Victoria Way, Chester, MD 21619

    This 1680 sq ft , 2 1/2 story townhome & this community have it all! It features many updates within the last year. It is "move-in ready", and if you would like, most furniture can be conveyed.. The updates include a new main-level half bath & a new full bathroom on the top level, both have new flooring, ADA-compliant toilets, new vanity/sink & faucets, and paint. Interior doors are 6 panel

    Melanie Mcknight RE/MAX Professionals

    9B Queen Victoria Way, Chester, MD 21619
  • 312 Blenny Ln, Chester, MD 21619
    312 Blenny Ln, Chester, MD 21619
    312 Blenny Ln, Chester, MD 21619
    /39

    $479,000

    • 3 Beds
    • 4 Baths
    • 1,899 Sq Ft

    312 Blenny Ln, Chester, MD 21619

    You do not want to miss this opportunity to enjoy island living in this maintenance free, WATER 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

    Judith Brown Samson Properties

    312 Blenny Ln, Chester, MD 21619
  • 49 Queen Guinivere Way, Chester, MD 21619
    49 Queen Guinivere Way, Chester, MD 21619
    49 Queen Guinivere Way, Chester, MD 21619
    /79

    $529,250

    • 2 Beds
    • 2.5 Baths
    • 1,600 Sq Ft

    49 Queen Guinivere Way, Chester, MD 21619

    Welcome to Queens Landing, where resort-style living meets the comfort of home. This beautifully updated townhome offers 1,440 square feet of thoughtfully designed living space plus an open sunroom, adding approximately 160 additional square feet, creating a seamless and spacious floor plan ideal for everyday living and entertaining.Enjoy panoramic water views from every room - lake and

    Julia Stevens Realty Navigator

    49 Queen Guinivere Way, Chester, MD 21619
  • 15 Queen Anne Way Unit E, Chester, MD 21619
    15 Queen Anne Way Unit E, Chester, MD 21619
    15 Queen Anne Way Unit E, Chester, MD 21619
    /68

    $539,000

    • 2 Beds
    • 2.5 Baths
    • 1,680 Sq Ft

    15 Queen Anne Way Unit E, Chester, MD 21619

    Price Improvement and a full year of Condo Fees paid!! Wake up to shimmering Chester River views and let every day feel like a getaway!This beautifully maintained 2.5-level townhome offers 1,680 square feet of stylish and functional living space in the sought-after waterfront community of Queens Landing. The main level features a cozy living area with a gas fireplace, luxury vinyl plank

    Julia Stevens Realty Navigator

    15 Queen Anne Way Unit E, Chester, MD 21619
  • 112 Harbour Sound Dr, Chester, MD 21619
    112 Harbour Sound Dr, Chester, MD 21619
    112 Harbour Sound Dr, Chester, MD 21619
    /40

    $539,500

    • 3 Beds
    • 3.5 Baths
    • 2,131 Sq Ft

    112 Harbour Sound Dr, Chester, MD 21619

    Resort Living at it's best!! Available furnished or unfurnished. Enjoy stunning, unobstructed water views in the highly sought after community of Bayside! Many recent upgrades and improvements to this home include renovated bathrooms (2024) , New garage door, with fresh sealing floor paint (2023) New Kitchen cabinets (2022), New Double Oven (2022) , New Quartz Countertops (2022) New flooring

    Carlos Larraz Annapolis Properties LLC

    112 Harbour Sound Dr, Chester, MD 21619
  • 1033 Dundee Ct Unit 5, Chester, MD 21619
    1033 Dundee Ct Unit 5, Chester, MD 21619
    1033 Dundee Ct Unit 5, Chester, MD 21619
    /63

    $365,000

    • 3 Beds
    • 2.5 Baths
    • 1,360 Sq Ft

    1033 Dundee Ct Unit 5, Chester, MD 21619

    Welcome to easy Eastern Shore living in this beautifully renovated 3 Bedroom, 2.5 Bath Townhouse Condo with water privileges, just minutes from the Bay Bridge! Updated top to bottom in 2023, this home is truly move-in ready! Enjoy peaceful mornings on the spacious screened-in porch, complete with bonus storage space, and spend afternoons at the community pier on scenic Piney Creek—perfect

    Erin Anderson Chesapeake Real Estate Associates, LLC

    1033 Dundee Ct Unit 5, Chester, MD 21619
  • 25 Queen Elizabeth Ct, Chester, MD 21619
    25 Queen Elizabeth Ct, Chester, MD 21619
    25 Queen Elizabeth Ct, Chester, MD 21619
    /39

    $569,000

    • 3 Beds
    • 2.5 Baths
    • 1,680 Sq Ft

    25 Queen Elizabeth Ct, Chester, MD 21619

    Experience breathtaking sunrises over the Chester River and Chesapeake Bay from this beautifully updated, three-level townhouse-style condo. Located in a serene waterfront community, this home offers the perfect blend of modern amenities and natural beauty. The front entrance welcomes you with a porcelain-tile foyer and a river-rock inset, leading into an open living area with stunning water

    Evguenia Mathur Samson Properties

    25 Queen Elizabeth Ct, Chester, MD 21619
  • 28E Queen Mary Ct, Chester, MD 21619
    28E Queen Mary Ct, Chester, MD 21619
    28E Queen Mary Ct, Chester, MD 21619
    /34

    $365,000

    • 3 Beds
    • 2.5 Baths
    • 1,680 Sq Ft

    28E Queen Mary Ct, Chester, MD 21619

    Just painted. One more thing allowing you to move right in and enjoy life overlooking the lake!Welcome to 28E Queen Mary Court — one of the largest condos in the sought-after Queens Landing community, offering 1,660 square feet of thoughtfully designed living space. This spacious 3-bedroom, 2.5-bath home is ideally positioned to take in the best of the neighborhood, with serene lake

    Justin Disborough Samson Properties

    28E Queen Mary Ct, Chester, MD 21619
  • 208 Ringneck Ct, Chester, MD 21619
    208 Ringneck Ct, Chester, MD 21619
    208 Ringneck Ct, Chester, MD 21619
    /57

    $339,900 Open House 8/17

    • 2 Beds
    • 2.5 Baths
    • 1,747 Sq Ft

    208 Ringneck Ct, Chester, MD 21619

    208 Ringneck Court is a great home for the smart buyer! The 2 bedroom, 2 1/2 bathroom GARAGE town-home, located in the Bayside community on the Chester River, underwent a MAJOR RENOVATION within the past 3 years. As you enter the south-facing home, you'll notice that the floor plan is a bit different than others...the kitchen has been reconfigured to create an open concept design which

    Phyllis Endrich Long & Foster Real Estate, Inc.

    208 Ringneck Ct, Chester, MD 21619
  • 202 Ringneck Ct, Chester, MD 21619
    202 Ringneck Ct, Chester, MD 21619
    202 Ringneck Ct, Chester, MD 21619
    /72

    $349,900

    • 2 Beds
    • 2.5 Baths
    • 1,956 Sq Ft

    202 Ringneck Ct, Chester, MD 21619

    PRICE IMPROVED.............Dont miss out, still time to enjoy summer near the water!Beautifully Updated End-Unit Townhouse in Sought-After Bayside Community!This spacious 2-bedroom, 2.5-bath end-unit townhome with a 1-car garage offers the perfect blend of comfort, style, and convenience. Step inside to discover a beautifully remodeled kitchen and updated bathrooms that add a

    Sheila Washburn Benson & Mangold, LLC

    202 Ringneck Ct, Chester, MD 21619
  • 206 Blenny Ln, Chester, MD 21619
    206 Blenny Ln, Chester, MD 21619
    206 Blenny Ln, Chester, MD 21619
    /23

    $359,900

    • 3 Beds
    • 4 Baths
    • 1,899 Sq Ft

    206 Blenny Ln, Chester, MD 21619

    Come see this town home with 1 car garage and offering 1900' of living space with interesting options on the first floor. Family room w/fp is connected to bright kitchen and sliders lead to 2nd floor deck. There are 3 Bedrooms and the Primary has a private bath with skylight. This light filled home is ready for your touches. New flooring on main level. Newer carpet on 3rd level. HVAC is

    Jimmy White Long & Foster Real Estate, Inc.

    206 Blenny Ln, Chester, MD 21619
  • 8 Queen Victoria Way, Chester, MD 21619
    8 Queen Victoria Way, Chester, MD 21619
    8 Queen Victoria Way, Chester, MD 21619
    /40

    $354,900

    • 3 Beds
    • 2.5 Baths
    • 1,680 Sq Ft

    8 Queen Victoria Way, Chester, MD 21619

    Upgraded two level townhouse, like new kitchen with granite counter tops, stainless steel appliances and ceramic floor on main level for easy cleaning. Wood burning fireplace and sliding doors to private patio that backs to common areas. Second level provides two bedrooms with vaulted ceilings and skylights, each with a private balcony. Two upgraded bathrooms, washer/dryer. Upgraded heating and

    Miguel Ruiz RE/MAX Realty Services

    8 Queen Victoria Way, Chester, MD 21619
  • 807 Auckland Way, Chester, MD 21619
    807 Auckland Way, Chester, MD 21619
    807 Auckland Way, Chester, MD 21619
    /34

    $497,000

    • 3 Beds
    • 3.5 Baths
    • 2,100 Sq Ft

    807 Auckland Way, Chester, MD 21619

    PRICE REDUCED! Waterside Living on Kent Island! Discover the perfect blend of comfort and convenience in this spacious 3-bedroom, 3.5-bathroom condo located on Kent Island, in the Bayside Condominiums waterside community. This 3-level condo offers a wonderful combination of space, style, and serene coastal living.The open-concept main floor features a freshly painted, inviting living

    Andrew Spagnolo Samson Properties

    807 Auckland Way, Chester, MD 21619
  • 7014 Bridgepointe Dr, Chester, MD 21619
    7014 Bridgepointe Dr, Chester, MD 21619
    /2

    $359,000

    • 3 Beds
    • 2.5 Baths
    • 1,635 Sq Ft

    7014 Bridgepointe Dr, Chester, MD 21619

    Welcome Home! This beautifully designed townhome features a bright and sunny kitchen that invites natural light to fill the space, perfect for cooking and entertaining. The high ceilings create an airy atmosphere, enhancing the open feel of the main level. The primary bedroom suite is conveniently located on the main level, offering privacy and ease of access. A stylish powder room is also

    Dee Dee Miller Long & Foster Real Estate, Inc.

    7014 Bridgepointe Dr, Chester, MD 21619
  • 108 Bodys Neck Rd, Chester, MD 21619
    108 Bodys Neck Rd, Chester, MD 21619
    108 Bodys Neck Rd, Chester, MD 21619
    /10

    $499,900 Coming Soon

    • 3 Beds
    • 2.5 Baths
    • 1,791 Sq Ft

    108 Bodys Neck Rd, Chester, MD 21619

    Coming Soon in Bayside on Kent Island – Resort-Style Island Living with Unmatched Water Views!Discover the perfect blend of coastal charm and modern luxury in this rarely available, oversized end-unit townhome Perfectly positioned to capture water views and marina, this meticulously updated 3-bedroom, 2.5-bath home offers a true resort-style experience in one of the Eastern Shore’s most

    Bill Longest Realty Navigator

    108 Bodys Neck Rd, Chester, MD 21619
Maryland Queen Annes County Chester

Townhomes for Sale 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

Home Trends in Chester, MD

On average, homes in Chester, MD sell after 41 days on the market compared to the national average of 70 days. The median sale price for homes in Chester, MD over the last 12 months is $645,000, down 12% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$645,000
Median Single Family Sale Price
$654,650
Median Townhouse Sale Price
$469,000
Median 2 Bedroom Sale Price
$539,950
Average Price Per Sq Ft
$350
Number of Homes for Sale
12
Last 12 months Home Sales
111
Months of Supply
1.30
Median List Price
$637,900
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-12%
How to Buy a Home How to Finance a Home How to Sell a Home

In Chester, there are currently 16 townhouses for sale, providing a range of options for prospective buyers. With townhouses priced between $339,900 to $569,000, there's a range to accomodate every budget. As of August, 2025 the median home price in Chester is $637,900, while the average sale price is $589,862, offering insights into the local housing market. On average, townhouses spend 41 days listed before being sold. Whether you're interested in modern townhouses, small townhomes, or traditional rowhouses, there are options to cater to different lifestyles. Explore the listings and townhomes for sale in Chester, MD, and find the perfect place to call home.

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