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Kingstown Homes for Sale

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  • 222 Dutchess Rd, Chestertown, MD 21620
    222 Dutchess Rd, Chestertown, MD 21620
    222 Dutchess Rd, Chestertown, MD 21620
    /24

    $320,000

    • 3 Beds
    • 1.5 Baths
    • 1,096 Sq Ft

    222 Dutchess Rd, Chestertown, MD 21620

    Three bedroom one-floor living on a spacious lot in Chester Harbor! Over half an acre of nicely shaded yard space, and a short distance to the public beach on Mill Creek. 3 bedrooms and 1.5 bathrooms, open living and dining space, large sunroom/ porch with wood-burning stove, and an additional wood stove in the living room. Outside there's a small storage shed and a larger workshop/shed next to

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 927-1169

    222 Dutchess Rd, Chestertown, MD 21620
  • 704 Truslow Rd, Chestertown, MD 21620
    704 Truslow Rd, Chestertown, MD 21620
    704 Truslow Rd, Chestertown, MD 21620
    /43

    $440,000

    • 3 Beds
    • 2.5 Baths
    • 2,060 Sq Ft

    704 Truslow Rd, Chestertown, MD 21620

    Tucked away in the peaceful countryside on the Queen Anne’s County side of Chestertown, this charming one-level rancher offers the space, comfort, and tranquility you’ve been waiting for. Situated on a full acre and boasting over 2,000 sq. ft. of living space, this home is designed for easy, one-level living with room to truly spread out. Offering 3 large bedrooms and 2.5 bathrooms, plus the

    Crystal Smith RE/MAX Executive

    704 Truslow Rd, Chestertown, MD 21620
  • 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
  • 107 Longfellow Dr, Chestertown, MD 21620
    107 Longfellow Dr, Chestertown, MD 21620
    107 Longfellow Dr, Chestertown, MD 21620
    /37

    $295,000

    • 3 Beds
    • 1 Bath

    107 Longfellow Dr, Chestertown, MD 21620

    There is so much potential for this 3 bedroom, 1 bath ranch, in need of a little updating, with attached carport located in Chester Harbor. There is a full unfinished basement and a 3 car detached garage all situated on 2 parcels that include 5 lots. Chester harbor offers water access to Rosin Creek.

    Doug Ashley Doug Ashley Realtors, LLC

    107 Longfellow 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
  • 154 Longfellow Dr, Chestertown, MD 21620
    154 Longfellow Dr, Chestertown, MD 21620
    154 Longfellow Dr, Chestertown, MD 21620
    /26

    $315,000

    • 3 Beds
    • 1 Bath
    • 1,408 Sq Ft

    154 Longfellow Dr, Chestertown, MD 21620

    Located in the water-oriented community of Chester Harbor just outside of historic Chestertown, 154 Longfellow Drive offers the ideal blend of convenience and Eastern Shore living. This single-level home is situated on a cleared and fenced 0.34 acre-parcel and a voluntary HOA fee provides access to the community boat ramp and waterfront park. Less than a mile and a half from Route 213, enjoy

    Katie Stecklair Cross Street Realtors LLC

    154 Longfellow Dr, Chestertown, MD 21620
  • 205 River Rd, Chestertown, MD 21620
    205 River Rd, Chestertown, MD 21620
    205 River Rd, Chestertown, MD 21620
    /14

    $949,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,877 Sq Ft

    205 River Rd, Chestertown, MD 21620

    COMING SOON......Stop scrolling!!!the home you’ve been waiting for is finally here!!! Currently under construction with an estimated May completion, this stunning almost 3,000 sq. ft. custom estate spares no expense. Situated on a level 1 acre lot directly across from the Chester River, this home blends designer elegance with functional luxury. Highlights include an expansive open floor plan,

    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 $355,000. If you put a 20% down payment of $71,000 and had a 30-year fixed mortgage with an interest rate of 6.46%, your estimated principal and interest payment would be $1,790 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $77K 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, 21668, 21678 and 21651.
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 5% in the last 12 months.

Home Trends in Kingstown, MD

On average, homes in Kingstown, Chestertown sell after 54 days on the market compared to the national average of 55 days. The median sale price for homes in Kingstown, Chestertown over the last 12 months is $349,950, consistent with the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$349,950
Median Single Family Sale Price
$344,900
Average Price Per Sq Ft
$228
Number of Homes for Sale
7
Last 12 months Home Sales
26
Months of Supply
3.20
Median List Price
$355,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
0%
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