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Kingstown Homes for Sale

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  • 109 Wilton Rd, Chestertown, MD 21620
    109 Wilton Rd, Chestertown, MD 21620
    109 Wilton Rd, Chestertown, MD 21620
    /31

    $344,900

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

    109 Wilton Rd, Chestertown, MD 21620

    Charming 3-bedroom, 2-bath rancher in the desirable Chester Harbor community. Situated on a spacious 0.76-acre lot, this home offers comfortable one-level living with a bright layout, private primary suite, and plenty of outdoor space to enjoy. Detached two-car garage provides ample storage and parking. Conveniently located just minutes from historic downtown Chestertown, marinas, shops, and

    Amy Larrauri Chesapeake Real Estate Associates, LLC

    109 Wilton Rd, Chestertown, MD 21620
  • 208 Central Dr, Chestertown, MD 21620
    208 Central Dr, Chestertown, MD 21620
    208 Central Dr, Chestertown, MD 21620
    /16

    $299,000

    $16K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,120 Sq Ft

    208 Central Dr, Chestertown, MD 21620

    Welcome to 208 Central Drive, located in the desirable Chester Harbor community just minutes from historic Chestertown. This charming 3-bedroom, 1-bath home offers a wonderful blend of comfort, convenience, and value. It sits on 3 lots totaling approximately 0.55 acres, surrounded by mature trees and landscaping. Step inside to a bright, move-in-ready interior featuring brand-new wood flooring

    Jennifer Pogoda Redfin Corp

    208 Central Dr, Chestertown, MD 21620
  • 101 Coleman Dr, Chestertown, MD 21620
    101 Coleman Dr, Chestertown, MD 21620
    101 Coleman Dr, Chestertown, MD 21620
    /56

    $524,900

    • 3 Beds
    • 2.5 Baths
    • 2,268 Sq Ft

    101 Coleman Dr, Chestertown, MD 21620

    Tucked away just south of the scenic Chester River and moments from the timeless charm of Chestertown, this inviting home offers a warm and welcoming retreat in the heart of Queen Anne’s County. Surrounded by the natural beauty of Maryland’s Eastern Shore, the setting feels peaceful and relaxed—where quiet mornings and golden sunsets become part of everyday life.Inside, the home is designed

    Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    101 Coleman Dr, Chestertown, MD 21620
  • 205 River Rd, Chestertown, MD 21620
    205 River Rd, Chestertown, MD 21620
    205 River Rd, Chestertown, MD 21620
    /72

    $899,500

    New Construction $50K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,877 Sq Ft

    205 River Rd, Chestertown, MD 21620

    New price, same stunning home!!! Stop scrolling — this beauty is ready for new owners to move in and make lasting memories! Welcome to this exceptional custom-built home offering nearly 3,000 sq. ft. of beautifully designed living space where luxury, comfort, and style come together effortlessly. Featuring 4 bedrooms and 2.5 baths, this home is perfectly situated on a level 1 acre lot directly

    Karen Clark Clark & Co Realty, LLC

    205 River Rd, Chestertown, MD 21620
Maryland Kent County Chestertown Kingstown

Real Estate & Homes 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

Frequently Asked Questions

Is Kingstown a good place to live?
Kingstown is a good place to live. Kingstown is considered very car-dependent and somewhat bikeable with minimal transit options. It has a median age of 44. The average household income is $101,535 which is below the national average. College graduates make up 48.1% of residents. A majority of residents in Kingstown are home owners, with 17% of residents renting and 83% of residents owning their home. A local real estate agent serving Kingstown can help you decide if this neighborhood is the right one for you. Learn more on our Kingstown neighborhood guide.
Is Kingstown, MD a safe neighborhood?
Kingstown, MD is safer than the average neighborhood in the United States. It received a crime score of 3 out of 10.
How much do you need to make to afford a house in Kingstown?
The median home price in Kingstown is $349,950. If you put a 20% down payment of $70,000 and had a 30-year fixed mortgage with an interest rate of 6.51%, your estimated principal and interest payment would be $1,770 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $76K a year to afford the median home price in Kingstown. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Kingstown is $102K.
What are the best public schools in Kingstown?
The best public schools that serve Kingstown are:
What are the best private schools in Kingstown?
The best private schools that serve Kingstown are:
What are the most popular zip codes in Kingstown, Chestertown, MD?
The most popular zip codes in Kingstown, Chestertown, MD include 21620, 21623, 21678, 21668 and 21617.
What are the most popular neighborhoods near Kingstown, Chestertown, MD?
The most popular neighborhood near Kingstown, Chestertown, MD is Kent Narrows.
Are home prices dropping in Kingstown?
Yes, home prices in Kingstown are down 8% in the last 12 months.

Home Trends in Kingstown, MD

On average, homes in Kingstown, Chestertown sell after 50 days on the market compared to the national average of 58 days. The median sale price for homes in Kingstown, Chestertown over the last 12 months is $337,450, down 4% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$337,450
Median Single Family Sale Price
$344,900
Average Price Per Sq Ft
$229
Number of Homes for Sale
4
Last 12 months Home Sales
28
Months of Supply
1.70
Median List Price
$349,950
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-4%
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