6

Chestertown, MD Open Houses

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  • 226 S Water St, Chestertown, MD 21620
    226 S Water St, Chestertown, MD 21620
    226 S Water St, Chestertown, MD 21620
    /31

    $898,000

    Open Sat 10AM - 2PM
    • 3 Beds
    • 3.5 Baths
    • 2,172 Sq Ft

    226 S Water St, Chestertown, MD 21620

    Newly constructed three-bedroom townhome with fantastic water views from the living level and bedrooms! Spacious open living space featuring a gourmet kitchen; 5-burner induction range, ample cabinet space, and a large island for entertaining. The home is filled with natural light and boasts multiple balconies and a front porch for relaxing. You'll love the warm hardwood floors throughout the

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 936-3661

    226 S Water St, Chestertown, MD 21620
  • 7989 Quaker Neck Rd, Chestertown, MD 21620
    7989 Quaker Neck Rd, Chestertown, MD 21620
    7989 Quaker Neck Rd, Chestertown, MD 21620
    /90

    $2,200,000

    Open Sat 11AM - 1PM
    • 5 Beds
    • 4.5 Baths
    • 4,305 Sq Ft

    7989 Quaker Neck Rd, Chestertown, MD 21620

    Price Improvement! Spectacular waterfront on the Chester River!! Words can't describe the uniqueness of this property. With the historic charm of an older home but high end modern upgrades, you will be living the life of luxury. Spacious rooms, magnificent views of the Chester River and your private dock with new boat lift, sandy beach, and stunning new saltwater pool. Exposed beams, scalamandre

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    7989 Quaker Neck Rd, Chestertown, MD 21620
  • 105 High St, Chestertown, MD 21620
    105 High St, Chestertown, MD 21620
    105 High St, Chestertown, MD 21620
    /48

    $1,295,500

    Open Sun 11AM - 1PM
    • 5 Beds
    • 4.5 Baths
    • 3,243 Sq Ft

    105 High St, Chestertown, MD 21620

    Rebuilt in 1863, the Tilley Residence showcases classic Second Empire architecture on one of Chestertown’s most prominent historic corners across from the Custom House, one of the first British Royal Ports of Entry to the Americas. Completely restored in 2025 by one of the Eastern Shore’s iconic builders, the home blends historic character with modern comfort through thoughtful updates, new

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    105 High St, Chestertown, MD 21620
  • 407 High St, Chestertown, MD 21620
    407 High St, Chestertown, MD 21620
    407 High St, Chestertown, MD 21620
    /58

    $828,000

    Open House 5/30
    • 3 Beds
    • 4.5 Baths
    • 3,047 Sq Ft

    407 High St, Chestertown, MD 21620

    Built in 1780/1840, "Highcroft" is in the heart of the Historic District near the Chester River. A rare in-town property that offers a 2-car garage with a second floor and a long driveway for tons of off-street parking. 3 bedrooms, 4 full baths and 1 half bath. Primary bedroom has his and hers private baths. 8.2 kw solar array on the garage. EV level 2 charger. Easy room flow from front to back

    Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

    407 High St, Chestertown, MD 21620
  • 106 S Queen St, Chestertown, MD 21620
    106 S Queen St, Chestertown, MD 21620
    106 S Queen St, Chestertown, MD 21620
    /92

    $865,000

    Open Sat 11AM - 2PM
    • 3 Beds
    • 3.5 Baths
    • 2,472 Sq Ft

    106 S Queen St, Chestertown, MD 21620

    New photos just added—capturing the truly one-of-a-kind gardens now in full bloom! This is a property you need to experience in person to fully appreciate the timeless character and breathtaking setting of this remarkable legacy home. The Bedingfield Hands House, circa 1750, traces its roots back to pre-revolutionary times and has a story to tell. One of the few downtown homes to offer a large

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    106 S Queen St, 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 Open Sat 11AM - 1PM $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

Open Houses in Chestertown, MD

Home Trends in Chestertown, MD

On average, homes in Chestertown, MD sell after 50 days on the market compared to the national average of 58 days. The median sale price for homes in Chestertown, MD over the last 12 months is $375,000, up 1% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$375,000
Median Single Family Sale Price
$398,000
Median Townhouse Sale Price
$287,500
Median 2 Bedroom Sale Price
$375,000
Median 1 Bedroom Sale Price
$285,000
Average Price Per Sq Ft
$211
Number of Homes for Sale
35
Last 12 months Home Sales
100
Months of Supply
4.20
Median List Price
$389,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
1%
How to Buy a Home How to Finance a Home How to Sell a Home

In Chestertown, there are currently 6 open houses available for viewing. Whether you're actively buying your first home or simply interested in the local real estate market, attending an open house can offer valuable insights. Open houses are a great way to do your homework before buying by exploring properties in-person, discovering new information, comparing options, learning about the local market, and forming relationships with real estate agents. Check out the open houses in Chestertown, MD today or take advantage of upcoming open houses this weekend to find the perfect place to call home.

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