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Chester, MD Townhomes for Sale

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  • 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
  • 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
  • 24 D Queen Elizabeth Ct, Chester, MD 21619
    24 D Queen Elizabeth Ct, Chester, MD 21619
    24 D Queen Elizabeth Ct, Chester, MD 21619
    /86

    $549,000

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

    24 D Queen Elizabeth Ct, Chester, MD 21619

    Welcome to 24D Queen Elizabeth Ct, a beautifully updated 2-bedroom waterfront condo with a spacious loft that easily serves as a third bedroom, office, or bonus space. Nestled in the highly desirable Queens Landing community, this home offers spectacular front and back water views — enjoy both peaceful sunrises and vibrant sunsets every day. Boat slip is negotiable with sale.Inside, the

    The Williams Home Team JPAR Maryland Living

    24 D Queen Elizabeth Ct, 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

    $529,500

    • 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 fountain

    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
  • 31C Queen Anne Way, Chester, MD 21619
    31C Queen Anne Way, Chester, MD 21619
    31C Queen Anne Way, Chester, MD 21619
    /46

    $334,900

    • 2 Beds
    • 1.5 Baths
    • 1,104 Sq Ft

    31C Queen Anne Way, Chester, MD 21619

    Welcome to 31-C Queen Anne Way, a beautifully updated two-bedroom, 1.5-bath located in Condo located in the desirable waterfront community of Queens Landing. This well-maintained unit offers 1,104 square feet of thoughtfully designed living space spread across the second and third levels. Enjoy unobstructed views of Lake Amletto and the community water tower, along with partial but striking

    Julia Stevens Realty Navigator

    31C Queen Anne Way, Chester, MD 21619
  • 35 F Queen Anne Way, Chester, MD 21619
    35 F Queen Anne Way, Chester, MD 21619
    35 F Queen Anne Way, Chester, MD 21619
    /60

    $354,900

    • 2 Beds
    • 2.5 Baths
    • 1,440 Sq Ft

    35 F Queen Anne Way, Chester, MD 21619

    Welcome to 35F Queen Anne Way in Queens Landing! This lakefront updated home offers 2 bedrooms and 2 full bathrooms. Updates include a spacious kitchen and both bathrooms. Wake up to lakefront views from the spacious primary bedroom and enjoy a cup of coffee or a glass of wine on the back patio or three season room while gazing over the lake. A stones throw away is the scenic Chester River

    Lawrence Doyle Long & Foster Real Estate, Inc.

    35 F Queen Anne Way, 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
  • 28E Queen Mary Ct, Chester, MD 21619
    28E Queen Mary Ct, Chester, MD 21619
    28E Queen Mary Ct, Chester, MD 21619
    /26

    $365,000

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

    28E Queen Mary Ct, Chester, MD 21619

    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 views from one side and the vibrant energy of the tennis and pickleball courts on the other.Tucked

    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
    /45

    $369,900

    • 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! This three-level, 2 bedroom, 2 1/2 bathroom garage town-home, located in the coveted Bayside Condominium neighborhood, was updated 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 is ideal

    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

    $374,900

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

    202 Ringneck Ct, Chester, MD 21619

    Seller New Home is Complete! Packing has started....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

    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

    $365,000

    • 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
  • 30 C Queen Mary Ct, Chester, MD 21619
    30 C Queen Mary Ct, Chester, MD 21619
    30 C Queen Mary Ct, Chester, MD 21619
    /26

    $304,000

    • 2 Beds
    • 2.5 Baths
    • 1,440 Sq Ft

    30 C Queen Mary Ct, Chester, MD 21619

    PRICE IMPROVEMENT! Amazing waterfront neighborhood on Northeast Bay leading to the Chester River! You'll feel the stress of the day melt away as you walk in the front door and immediately see the expansive view of the pond and fountain in the rear. Large windows take advantage of the gorgeous views of the pond behind the property. There are walkways around the water's edge of the

    Tina Cadden Jenkins Douglas Realty, LLC

    30 C Queen Mary Ct, 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

    $359,900

    • 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

    $535,000

    • 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 room with a

    Andrew Spagnolo Samson Properties

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

    $359,000 Coming Soon

    • 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
Maryland Chester

Townhomes for Sale in Chester, MD

Why Live in Chester

Chester features a diverse housing market with single-family homes, condos, and townhouses. The neighborhood includes ranch-style homes, colonials, and New Traditional builds. Properties south of Highway 50 date back to the mid-to-late 20th century, while newer communities in the northern sector have been developed over the past decade. Chester's parks and recreational activities are abundant, with Terrapin Nature Park offering walking paths and Chesapeake Bay views, and the Cross Island Trail providing a paved walkway for hikers and cyclists. Castle Marina is a hub for boating activities, and Club One Fitness and Aerobics offers gym facilities and an aquatic center. Shopping and dining are concentrated in plazas off Highway 50, with big-box stores like Safeway, Walgreens, and Target, and a variety of restaurants ranging from fast food to local favorites. Notable dining spots include The Jetty, Bridges, and Fisherman’s Inn in nearby Kent Narrows. Annual events such as the Kent Island Day parade and the Annapolis Baygrass Music Festival bring the community together. Highway 50 is the main thoroughfare, connecting Chester to Annapolis, 17 miles away, and the Chesapeake Bay Bridge provides access to Baltimore and Washington, D.C. Public transportation is available via Queen Anne’s County buses, and BWI International Airport is about 30 miles away. Schools in Chester are highly rated, with Bayside Elementary, Stevensville Middle, and Kent Island High all receiving strong ratings.
Learn more about living in Chester

Home Trends in Chester, MD

On average, homes in Chester, MD sell after 49 days on the market compared to the national average of 50 days. The median sale price for homes in Chester, MD over the last 12 months is $575,000, up 9% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$575,000
Median Single Family Sale Price
$630,900
Median Townhouse Sale Price
$390,500
Median 2 Bedroom Sale Price
$499,000
Median 1 Bedroom Sale Price
$293,000
Average Price Per Sq Ft
$294
Number of Homes for Sale
77
Last 12 months Home Sales
173
Months of Supply
5.30
Median List Price
$569,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
9%
How to Buy a Home How to Finance a Home How to Sell a Home

In Chester, there are currently 17 townhouses for sale, providing a range of options for prospective buyers. With townhouses priced between $304,000 to $569,000, there's a range to accomodate every budget. As of July, 2025 the median home price in Chester is $569,000, while the average sale price is $590,679, offering insights into the local housing market. On average, townhouses spend 49 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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