8

Chestertown, MD Townhomes for Sale

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  • 103 Landing Ln, Chestertown, MD 21620
    103 Landing Ln, Chestertown, MD 21620
    103 Landing Ln, Chestertown, MD 21620
    /41

    $569,000

    • 2 Beds
    • 2.5 Baths
    • 2,100 Sq Ft

    103 Landing Ln, Chestertown, MD 21620

    Step into this nearly new, impeccably maintained two-bedroom townhouse located in the highly desirable Chester River Landing community. Recent upgrades make this home truly turn-key, perfect for those seeking comfort and style. Relax and entertain all summer long on the beautifully designed screened-in porch, ideal for enjoying warm evenings and gentle breezes.On the second floor, the

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 981-2534

    103 Landing Ln, Chestertown, MD 21620
  • 21316 Persimmon Dr, Chestertown, MD 21620
    21316 Persimmon Dr, Chestertown, MD 21620
    21316 Persimmon Dr, Chestertown, MD 21620
    /25

    $179,000

    • 2 Beds
    • 1 Bath
    • 1,232 Sq Ft

    21316 Persimmon Dr, Chestertown, MD 21620

    Two bedroom & one bath townhome with a nice view from the living room/patio area. Located very close to a public landing and Tolchester Marina, which offers full service. This townhouse has outdoor storage both on the front patio area and the back patio area. New carpet and fresh paint will update this property nicely. Covered storage for bikes/yard toys and more. The townhouse is all

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (410) 708-2172

    21316 Persimmon Dr, Chestertown, MD 21620
  • 226 S Water St, Chestertown, MD 21620
    226 S Water St, Chestertown, MD 21620
    226 S Water St, Chestertown, MD 21620
    /22

    $998,000 New Construction

    • 3 Beds
    • 3.5 Baths

    226 S Water St, Chestertown, MD 21620

    Newly finished 3 Bedroom townhouses with nearly all the desired attributes of town living, with harbor and marina views and access from the marina on one side and waterfront park on the other. A short walk to downtown shops and restaurants. No short term rental restrictions.

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 376-5375

    226 S Water St, Chestertown, MD 21620
  • 212 Landing Ln, Chestertown, MD 21620
    212 Landing Ln, Chestertown, MD 21620
    212 Landing Ln, Chestertown, MD 21620
    /36

    $759,000 New Construction

    • 3 Beds
    • 3.5 Baths

    212 Landing Ln, Chestertown, MD 21620

    Nestled along the tranquil western shore of the Chester River, this beautiful townhome in Chester River Landing offers an unparalleled waterfront living experience with direct water access and captivating water views. Just a short stroll from the historic heart of Chestertown, MD, it combines modern luxury with timeless charm.This elegant 3-bedroom, 2.5-bath residence is designed to

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 883-7032

    212 Landing Ln, Chestertown, MD 21620
  • 724 Aldora Dr Unit 111, Chestertown, MD 21620
    724 Aldora Dr Unit 111, Chestertown, MD 21620
    724 Aldora Dr Unit 111, Chestertown, MD 21620
    /38

    $569,990 New Construction

    • 4 Beds
    • 3.5 Baths
    • 2,570 Sq Ft

    724 Aldora Dr Unit 111, Chestertown, MD 21620

    HOME OF THE MONTH -Under ConstructionLuxury, End of Group, 4 Bedroom Villa with a walk-out lower level. The layout is welcoming and very functional. The main level boasts an oversized family room which is open to the kitchen and dining area. The second floor boasts 3 bedrooms with an owner's suite that includes 2 walk-in closets and private bath which boasts ceramic tile, a double bowl

    Agent Photo

    Terri Hill

    Builder Solutions Realty

    (410) 883-7905

    724 Aldora Dr Unit 111, Chestertown, MD 21620
  • 728 Aldora Dr Unit 113, Chestertown, MD 21620
    728 Aldora Dr Unit 113, Chestertown, MD 21620
    728 Aldora Dr Unit 113, Chestertown, MD 21620
    /38

    $519,990 New Construction

    • 4 Beds
    • 3.5 Baths
    • 2,570 Sq Ft

    728 Aldora Dr Unit 113, Chestertown, MD 21620

    HOME OF THE MONTH -Under ConstructionLuxury 4 Bedroom Villa. The layout is welcoming and very functional. The main level boasts an oversized family room which is open to the kitchen and dining area. The second floor boasts 3 bedrooms with an owner's suite that includes 2 walk-in closets and private bath which boasts ceramic tile, a double bowl sink, private water closet and seated shower

    Agent Photo

    Terri Hill

    Builder Solutions Realty

    (410) 517-7657

    728 Aldora Dr Unit 113, Chestertown, MD 21620
  • 100 Metcalf Rd, Chestertown, MD 21620
    100 Metcalf Rd, Chestertown, MD 21620
    100 Metcalf Rd, Chestertown, MD 21620
    /17

    $255,000

    • 3 Beds
    • 2 Baths
    • 1,140 Sq Ft

    100 Metcalf Rd, Chestertown, MD 21620

    Welcome to Your Brand-New Beginning in Chestertown! Step into this stunning, move-in-ready home at 100 Metcalf Rd, Chestertown, MD 21620. For just $255,000, you can own this beautiful 3-bedroom, 2-bath ranch without the wait or hassle of new construction.Your Dream Home AwaitsThis one-level townhome is designed for easy living. You’ll love the freedom and savings that come

    Dale Hunter Bayside Realty

    100 Metcalf Rd, Chestertown, MD 21620
  • 112 Metcalf Rd, Chestertown, MD 21620
    112 Metcalf Rd, Chestertown, MD 21620
    112 Metcalf Rd, Chestertown, MD 21620
    /20

    $265,000

    • 3 Beds
    • 1.5 Baths
    • 1,280 Sq Ft

    112 Metcalf Rd, Chestertown, MD 21620

    Come enjoy the this 2 year old home in Historic Chestertown. The home features 3 full bedrooms with 1 1/2 baths . It has an open concept on the main floor, kitchen has beautiful white shaker cabinetry, large island, granite countertops, stainless steel appliances, and luxury vinyl flooring. Large covered patio off the kitchen leading out to a spacious back yard. A new shed recently installed

    Steven Knopf Engel & Völkers Annapolis

    112 Metcalf Rd, Chestertown, MD 21620
Maryland Kent County Chestertown

Townhomes for Sale in Chestertown, MD

Home Trends in Chestertown, MD

On average, homes in Chestertown, MD sell after 52 days on the market compared to the national average of 52 days. The median sale price for homes in Chestertown, MD over the last 12 months is $362,500, up 8% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$362,500
Median Single Family Sale Price
$394,000
Median Townhouse Sale Price
$289,500
Median 2 Bedroom Sale Price
$565,000
Median 1 Bedroom Sale Price
$285,000
Average Price Per Sq Ft
$217
Number of Homes for Sale
32
Last 12 months Home Sales
94
Months of Supply
4.10
Median List Price
$385,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
8%
How to Buy a Home How to Finance a Home How to Sell a Home

In Chestertown, there are currently 8 townhouses for sale, providing a range of options for prospective buyers. With townhouses priced between $179,000 to $998,000, there's a range to accomodate every budget. As of September, 2025 the median home price in Chestertown is $385,000, while the average sale price is $432,594, offering insights into the local housing market. On average, townhouses spend 52 days listed before being sold. Whether you're interested in modern townhouses, small townhomes, or traditional rowhouses, there are options to cater to different lifestyles. Explore the listings and townhomes for sale in Chestertown, MD, and find the perfect place to call home.

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