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Kingstown Homes for Sale

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  • 119 Darden Rd, Chestertown, MD 21620
    119 Darden Rd, Chestertown, MD 21620
    /2

    $315,000

    • 3 Beds
    • 2 Baths
    • 1,424 Sq Ft

    119 Darden Rd, Chestertown, MD 21620

    Welcome to 119 Darden Road, a lovely ranch-style home nestled in Chestertown, MD. This charming residence offers 3 cozy bedrooms and 2 bathrooms across 1,424 square feet of living space, perfect for comfortable living. The eat-in kitchen, complete with a handy stove, sets the stage for delightful meals and gatherings. Enjoy the warm ambiance of a fireplace in the spacious living room, enhanced by

    Solomon Zaldivar Compass

    119 Darden Rd, Chestertown, MD 21620
  • 201 Boundary Ave, Chestertown, MD 21620
    201 Boundary Ave, Chestertown, MD 21620
    201 Boundary Ave, Chestertown, MD 21620
    /46

    $449,000

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

    201 Boundary Ave, Chestertown, MD 21620

    Discover this spacious home offering 3,100 sq ft of living space on a 1⁄2 acre lot with deeded access to the Chester River. Generously sized rooms and an inviting floor plan create an ideal setting for both everyday living and entertaining. The main level bedroom features a recently remodeled bath and large walk in closet. Enjoy the natural light and tranquil views from the sunroom, perfect for

    Mary Carlisle Coldwell Banker Chesapeake Real Estate Company

    201 Boundary Ave, Chestertown, MD 21620
  • 600 Rosin Dr, Chestertown, MD 21620
    600 Rosin Dr, Chestertown, MD 21620
    600 Rosin Dr, Chestertown, MD 21620
    /36

    $424,000

    • 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
  • 0 East St, Chestertown, MD 21620
    0 East St, Chestertown, MD 21620
    0 East St, Chestertown, MD 21620
    /11

    $103,000

    • Land
    • 0.48 Acre
    • $214,583 per Acre

    0 East St, Chestertown, MD 21620

    Great chance to purchase a corner lot just across the river from Chestertown's Historic District. Sit and listen to the birds by the pond on this peaceful retreat just minutes from the town's shops, galleries, and waterfront. There aren't many more opportunities like this. Please see the documents for the perc approval and site plan.

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    0 East St, Chestertown, MD 21620
  • 128 Edmore Rd, Chestertown, MD 21620
    128 Edmore Rd, Chestertown, MD 21620
    128 Edmore Rd, Chestertown, MD 21620
    /59

    $415,000

    • 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
    /31

    $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
  • 116 Pine Chip Rd, Chestertown, MD 21620
    116 Pine Chip Rd, Chestertown, MD 21620
    116 Pine Chip Rd, Chestertown, MD 21620
    /35

    $475,000

    • 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
  • 221 Old Bridge Rd, Chestertown, MD 21620
    221 Old Bridge Rd, Chestertown, MD 21620
    221 Old Bridge Rd, Chestertown, MD 21620
    /11

    $369,900 Coming Soon

    • 3 Beds
    • 2 Baths
    • 1,851 Sq Ft

    221 Old Bridge Rd, Chestertown, MD 21620

    Coming Soon! Charming American Foursquare on a half-acre corner lot, just one block from the Chester River on the Queen Anne's County side of Historic Chestertown. The home features a welcoming front porch, 3 bedrooms, 2 full baths, an office on the main level, hardwood floors, and many original details. Recent updates include a new upstairs bathroom, new electric panel, and a 2-year-old roof.

    Courtney Chipouras TTR Sotheby's International Realty

    221 Old Bridge Rd, Chestertown, MD 21620
  • 110 Tuxedo Rd, Chestertown, MD 21620
    110 Tuxedo Rd, Chestertown, MD 21620
    /2

    $275,000 Coming Soon

    • 3 Beds
    • 2.5 Baths
    • 1,664 Sq Ft

    110 Tuxedo Rd, Chestertown, MD 21620

    YOUR DIAMOND IN ROUGH.........Home is original and needs updating through out....Priced to sell. Good bones, will need a buyer with vision. Main level has a large eat in kitchen, living room area and laundry room. Upper level has 3 bedrooms, 2 full bath; including master on suite. Large deck and fenced in back yard. Minutes from The Chester Bridge.

    Vince Stonesifer Cummings & Co. Realtors

    110 Tuxedo 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. 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.
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 6.26%, your estimated principal and interest payment would be $1,730 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $74K 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 21620, 21623, 21678, 21668 and 21628.
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 6% in the last 12 months.

Home Trends in Kingstown, MD

On average, homes in Kingstown, Chestertown sell after 53 days on the market compared to the national average of 52 days. The median sale price for homes in Kingstown, Chestertown over the last 12 months is $346,950, up 3% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$346,950
Median Single Family Sale Price
$349,950
Average Price Per Sq Ft
$221
Number of Homes for Sale
8
Last 12 months Home Sales
30
Months of Supply
3.20
Median List Price
$349,950
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
3%
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