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Kingstown Homes for Sale

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  • 104 Dutchess Rd, Chestertown, MD 21620
    104 Dutchess Rd, Chestertown, MD 21620
    104 Dutchess Rd, Chestertown, MD 21620
    /23

    $312,000

    • 3 Beds
    • 2 Baths
    • 1,188 Sq Ft

    104 Dutchess Rd, Chestertown, MD 21620

    This home is a must see! Join the Chester Harbor Community.A charming home in a lovely neighborhood on Maryland's Eastern Shore. Welcome to Chester Harbor, Queen Anne's County. Only minutes from historic Chestertown, this three bedroom, two bath home offers one-level living and an appealing owner's suite. The expansive, fully fenced backyard is easily accessed from the private deck off of the

    Helen J Butler Taylor Properties

    104 Dutchess Rd, Chestertown, MD 21620
  • 114 Ryan Ct, Chestertown, MD 21620
    114 Ryan Ct, Chestertown, MD 21620
    114 Ryan Ct, Chestertown, MD 21620
    /36

    $459,000

    • 2 Beds
    • 2 Baths
    • 1,496 Sq Ft

    114 Ryan Ct, Chestertown, MD 21620

    Perched above the peaceful waters of Rosin Creek, this charming waterfront cottage offers a rare opportunity to create your dream retreat. Whether you are searching for a cozy weekend getaway, a lucrative short-term rental, or a serene place to call home, this diamond in the rough is full of potential. Just a stone’s throw from historic Chestertown, the property combines seclusion with

    Julie Santoboni Taylor Properties

    114 Ryan Ct, Chestertown, MD 21620
  • 114 Darden Rd, Chestertown, MD 21620
    114 Darden Rd, Chestertown, MD 21620
    114 Darden Rd, Chestertown, MD 21620
    /33

    $289,900

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

    114 Darden Rd, Chestertown, MD 21620

    All one floor living on quiet street with large fenced yard and mature trees close to the bay! Lovely renovations and brand new kitchen with solid white shaker cabinetry including soft close dovetailed drawers and new stainless steel appliances PLUS BRAND NEW ROOF! Brand New septic system to be installed by settlement! ABSOLUTE MUST SEE HOME!

    Lee Wolff FSBO Broker

    114 Darden Rd, Chestertown, MD 21620
  • 128 Edmore Rd, Chestertown, MD 21620
    128 Edmore Rd, Chestertown, MD 21620
    128 Edmore Rd, Chestertown, MD 21620
    /57

    $440,000

    • 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
  • 118 Tuxedo Rd, Chestertown, MD 21620
    118 Tuxedo Rd, Chestertown, MD 21620
    118 Tuxedo Rd, Chestertown, MD 21620
    /26

    $274,000

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

    118 Tuxedo Rd, Chestertown, MD 21620

    Three bedroom/one bath rancher located in a water-oriented community just minutes from Chestertown. There is a Home Owners Association; however, is not mandatory to join. Home is being sold as is.

    Debbie Meikle Doug Ashley Realtors, LLC

    118 Tuxedo 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

    Amy Larrauri Chesapeake Real Estate Associates, LLC

    109 Wilton Rd, Chestertown, MD 21620
  • 909 Round Top Rd, Chestertown, MD 21620
    909 Round Top Rd, Chestertown, MD 21620
    909 Round Top Rd, Chestertown, MD 21620
    /37

    $309,000

    • 3 Beds
    • 1 Bath
    • 1,698 Sq Ft

    909 Round Top Rd, Chestertown, MD 21620

    Need additional space, no problem! This home has a sunken den with a brick wood fireplace off the main living room that could be used as an office and a humongous 23’8 X 18’4 family room currently used as the Billards room hosting a 9ft pool table/gym off the kitchen/dinning room that was added in 2021! This room is great for entertaining & hosting large parties and could be a fantastic place to

    Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    909 Round Top Rd, Chestertown, MD 21620
  • 107 Dutchess Rd, Chestertown, MD 21620
    107 Dutchess Rd, Chestertown, MD 21620
    107 Dutchess Rd, Chestertown, MD 21620
    /15

    $335,000 Open Sun 1PM - 3PM

    • 3 Beds
    • 2 Baths
    • 1,380 Sq Ft

    107 Dutchess Rd, Chestertown, MD 21620

    Welcome to Chester Harbor - a family oriented place to live! The Chester Harbor Community has a voluntary HOA of $30/year, which offers water access, a beach, community events, and a playground. Close by is Round Top Park offering tennis, pickleball, and basketball courts, a playground, and a pavilion. Minutes from Chestertown's historic waterfront, restaurants, shopping, and marinas. Queen

    Jo Ann Edwards The Hogans Agency

    107 Dutchess 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

    $515,000

    • 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 stove,

    William Sutton Coldwell Banker Chesapeake Real Estate Company

    116 Pine Chip Rd, Chestertown, MD 21620
Maryland Chestertown Kingstown

Real Estate & Homes for Sale in Kingstown, Chestertown

About 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, says people like Kingstown for its proximity to Chestertown’s shopping and dining. The town is only about a mile away, but not being within its borders means a quieter atmosphere and lower taxes. And despite being so close, the two areas are in different counties, with Kingstown sitting in Queen Anne’s ...

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. Kingstown is a neighborhood with a crime score of 2, making it safer than the average neighborhood in the U.S. It has a median age of 44. The average household income is $101,535 which is above 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 2 out of 10.
How much do you need to make to afford a house in Kingstown?
The median home price in Kingstown is $349,000. If you put a 20% down payment of $69,800 and had a 30-year fixed mortgage with an interest rate of 6.83%, your estimated principal and interest payment would be $1,830 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $78K a year to afford the median home price in Kingstown. 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 19709, 21619, 21620, 21220 and 21666.
What are the most popular neighborhoods near Kingstown, Chestertown, MD?
The most popular neighborhoods near Kingstown, Chestertown, MD are Kent Narrows, Bowleys Quarters, Long Bar Harbor, Old Philadelphia and Joppa.

Home Trends in Kingstown, MD

On average, homes in Kingstown, Chestertown sell after 37 days on the market compared to the national average of 47 days. The average sale price for homes in Kingstown, Chestertown over the last 12 months is $415,604, up 18% from the average home sale price over the previous 12 months.

Home Trends

Median Price (12 Mo)
$349,500
Median Single Family Price
$349,000
Average Price Per Sq Ft
$239
Number of Homes for Sale
9
Last 12 months Home Sales
36
Months of Supply
3.00
Median List Price
$349,000
Median Discount From 1st List Price
0%
Median Home Sale Price YoY Change
5%
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