5

Chestertown, MD Open Houses

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  • 7989 Quaker Neck Rd, Chestertown, MD 21620
    7989 Quaker Neck Rd, Chestertown, MD 21620
    7989 Quaker Neck Rd, Chestertown, MD 21620
    /61

    $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

    $1,245,500

    Open House 7/11
    • 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
  • 210 N Queen St, Chestertown, MD 21620
    210 N Queen St, Chestertown, MD 21620
    210 N Queen St, Chestertown, MD 21620
    /12

    $735,000

    Open House 7/18 Coming Soon
    • 4 Beds
    • 2.5 Baths
    • 2,730 Sq Ft

    210 N Queen St, Chestertown, MD 21620

    Experience the warmth and charm of in-town living in this beautiful residence in Chestertown's Historic District. Just a few blocks from the waterfront, shops, galleries, and restaurants, it offers the perfect balance of walkability and tranquility on one of the district's quietest streets. The thoughtfully designed layout makes excellent use of every square foot, while tasteful updates fill the

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    210 N Queen St, Chestertown, MD 21620
  • 103 Metcalf Rd, Chestertown, MD 21620
    103 Metcalf Rd, Chestertown, MD 21620
    103 Metcalf Rd, Chestertown, MD 21620
    /22

    $259,900

    New Construction Open Sat 12PM - 4PM
    • 3 Beds
    • 1.5 Baths
    • 1,280 Sq Ft

    103 Metcalf Rd, Chestertown, MD 21620

    Brand new home in Historic Chestertown available for move-in now. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you’ll find generously sized bedrooms including a large primary suite with walk-in

    David Moore Real Broker, LLC

    103 Metcalf Rd, Chestertown, MD 21620
  • 105 N Water St Unit 2, Chestertown, MD 21620
    105 N Water St Unit 2, Chestertown, MD 21620
    105 N Water St Unit 2, Chestertown, MD 21620
    /49

    $475,000

    Open Fri 4PM - 6PM
    • 2 Beds
    • 2 Baths
    • 1,011 Sq Ft

    105 N Water St Unit 2, Chestertown, MD 21620

    Open House Friday July 3rd 4-6pm! Located on Water Street in the heart of Chestertown's premier waterfront historic district, this beautiful two-bedroom, two-bath condominium offers an exceptional opportunity to enjoy life along the banks of the Chester River. Set within an architecturally significant 1800s building that reflects the timeless character of this remarkable town, the residence

    Missy Miller Aldave Northrop Realty

    105 N Water St Unit 2, Chestertown, MD 21620
Maryland Kent County Chestertown

Open Houses in Chestertown, MD

Home Prices in Chestertown, MD

The median home sale price in Chestertown, MD is $357,450, down 6% year-over-year. Homes in Chestertown sell in 51 days on average, compared to the national average of 57 days.

Home Price Trends

Median Sale Price
$357,450
Median Single Family Sale Price
$379,900
Median Townhouse Sale Price
$264,900
Median 2 Bedroom Sale Price
$355,000
Median 1 Bedroom Sale Price
$242,500
Average Price Per Sq Ft
$220
Number of Homes for Sale
29
Last 12 months Home Sales
96
Months of Supply
3.60
Median List Price
$364,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-6%
How to Buy a Home How to Finance a Home How to Sell a Home

In Chestertown, there are currently 5 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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