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Kingstown Houses for Sale

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  • 925 Round Top Rd, Chestertown, MD 21620
    925 Round Top Rd, Chestertown, MD 21620
    925 Round Top Rd, Chestertown, MD 21620
    /19

    $300,000

    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft

    925 Round Top Rd, Chestertown, MD 21620

    Welcome to this cute-as-a-button home in the water-access community of Chester Harbor! Whether you're starting out, downsizing, or simply looking to simplify your lifestyle, this move-in ready gem offers the perfect balance of comfort, convenience, and charm. Set on a spacious third of an acre lot, this home offers just the right amount of space—three bedrooms, one full bath, and room to grow

    Liddy Campbell TTR Sotheby's International Realty

    925 Round Top Rd, Chestertown, MD 21620
  • 128 Edmore Rd, Chestertown, MD 21620
    128 Edmore Rd, Chestertown, MD 21620
    128 Edmore Rd, Chestertown, MD 21620
    /59

    $425,000

    • 4 Beds
    • 2 Baths
    • 2,568 Sq Ft

    128 Edmore Rd, Chestertown, MD 21620

    Your Dream Eastern Shore Retreat Awaits!Welcome to this meticulously maintained home, where charm and comfort blend seamlessly. Whether you're savoring peaceful nights or hosting lively gatherings, this home offers the perfect setting.Step into the breathtaking four-seasons room, where natural light pours in, highlighting an authentic reclaimed barn wood accent wall—crafted from

    Lauren Matera Berkshire Hathaway HomeServices PenFed Realty

    128 Edmore Rd, Chestertown, MD 21620
  • 109 Wilton Rd, Chestertown, MD 21620
    109 Wilton Rd, Chestertown, MD 21620
    109 Wilton Rd, Chestertown, MD 21620
    /30

    $349,900

    • 3 Beds
    • 2 Baths
    • 1,392 Sq Ft

    109 Wilton Rd, Chestertown, MD 21620

    Welcome to this charming 3-bedroom, 2-bathroom rancher, offering the perfect blend of comfort and convenience with one-level living in the desirable Chester Harbor community. Set on a spacious .76-acre lot on the Queen Anne's side of the Chester River, this home is ideally situated in a water-oriented neighborhood, perfect for boating enthusiasts and nature lovers alike.The home boasts a large

    Amy Larrauri Chesapeake Real Estate Associates, LLC

    109 Wilton Rd, Chestertown, MD 21620
  • 116 Pine Chip Rd, Chestertown, MD 21620
    116 Pine Chip Rd, Chestertown, MD 21620
    116 Pine Chip Rd, Chestertown, MD 21620
    /35

    $495,000

    • 3 Beds
    • 1.5 Baths
    • 2,767 Sq Ft

    116 Pine Chip Rd, Chestertown, MD 21620

    Don’t let the outside fool you—this beautifully renovated 3-bedroom, 1.5-bathroom home offers three levels of living space, with over 2,200 sq. ft. above ground and an additional 550 sq. ft. below ground! Every inch of this home has been thoughtfully updated to blend modern comfort with timeless charm.Step inside to discover a stunning custom kitchen, a true chef’s dream featuring a gas

    William Sutton Coldwell Banker Chesapeake Real Estate Company

    116 Pine Chip Rd, Chestertown, MD 21620
  • 600 Rosin Dr, Chestertown, MD 21620
    600 Rosin Dr, Chestertown, MD 21620
    600 Rosin Dr, Chestertown, MD 21620
    /4

    $424,000 Coming Soon

    • 3 Beds
    • 3 Baths
    • 1,300 Sq Ft

    600 Rosin Dr, Chestertown, MD 21620

    Nestled along the peaceful shores of Rosin Creek, this charming 3-bedroom, 2-bathroom waterfront cottage combines classic character with modern updates. Inside, the open floor plan creates a warm, inviting flow—perfect for everyday living or entertaining. The renovated kitchen features stylish finishes and connects seamlessly to the dining and living areas, all enhanced by updated flooring and

    Sarah King Cross Street Realtors LLC

    600 Rosin Dr, Chestertown, MD 21620
  • 201 Boundary Ave, Chestertown, MD 21620
    201 Boundary Ave, Chestertown, MD 21620
    201 Boundary Ave, Chestertown, MD 21620
    /7

    $470,000 Open House 8/09

    • 4 Beds
    • 3 Baths
    • 3,096 Sq Ft

    201 Boundary Ave, Chestertown, MD 21620

    Mary Carlisle Coldwell Banker Chesapeake Real Estate Company

    201 Boundary Ave, Chestertown, MD 21620
Maryland Kent County Chestertown Kingstown

Houses for Sale in Kingstown, Chestertown

Why Live in Kingstown
Kingstown is a quiet suburb bracketed by the Chester River and Chestertown to the west and farmland to the east. Thomas Boeshore, an associate broker at Berkshire Hathaway HomeServices Homesale Realty who has sold homes in the area for 27 years, ...
Learn more about living in Kingstown

Home Trends in Kingstown, MD

On average, homes in Kingstown, Chestertown sell after 60 days on the market compared to the national average of 70 days. The median sale price for homes in Kingstown, Chestertown over the last 12 months is $520,000, down 17% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$520,000
Median Single Family Sale Price
$460,000
Median 1 Bedroom Sale Price
$710,000
Average Price Per Sq Ft
$291
Number of Homes for Sale
6
Last 12 months Home Sales
38
Months of Supply
1.90
Median List Price
$497,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-17%
How to Buy a Home How to Finance a Home How to Sell a Home

In Kingstown, there are currently 6 houses for sale, offering a variety of options for prospective buyers. With houses ranging from $300,000 to $495,000, there's something for every budget. As of July, 2025 the median home price in Kingstown, Chestertown is $497,000, while the average sale price is $669,736, providing insight into local market trends. On average, houses spend 60 days on the market before being sold. Whether you're searching for a single-family residence, exploring single-family detached houses for sale, or considering new construction houses for sale, there are options available to suit every lifestyle. Browse properties and houses for sale in Kingstown, Chestertown and find the perfect place to call home.

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