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Chestertown, MD Townhomes for Sale

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  • 21316 Persimmon Dr, Chestertown, MD 21620
    21316 Persimmon Dr, Chestertown, MD 21620
    21316 Persimmon Dr, Chestertown, MD 21620
    /21

    $179,000

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

    21316 Persimmon Dr, Chestertown, MD 21620

    Back on the market through no fault of the sellers. Home inspection went well. Two bedroom, one bath townhome with a nice view from the living room/patio area. NEW CARPET in living area/hallway on the main level and upstairs! Looks great! Located very close to a public landing and Tolchester Marina, which offers full service. This townhouse has outdoor storage both on the front patio

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (410) 267-4230

    21316 Persimmon Dr, Chestertown, MD 21620
  • 228 S Water St, Chestertown, MD 21620
    228 S Water St, Chestertown, MD 21620
    228 S Water St, Chestertown, MD 21620
    /32

    $878,000 New Construction

    • 3 Beds
    • 3.5 Baths
    • 2,310 Sq Ft

    228 S Water St, Chestertown, MD 21620

    Newly constructed three-bedroom townhome with all the desired attributes. Fantastic water views from the living level and bedrooms! Spacious open living space with warm hardwood floors and 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. On the

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 647-9404

    228 S Water St, 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
    /42

    $524,990 New Construction

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

    724 Aldora Dr Unit 111, Chestertown, MD 21620

    PRICE IMPROVEMENT ON THIS STUNNING QUICK MOVE IN-Close by 12/31/25 and receive a FREE washer/dryer and blinds. Luxury end-of-group 4-bedroom villa with a fully finished walk-out lower level. The open and functional layout features an oversized family room that flows into the kitchen and dining area, perfect for entertaining. The upper level includes three spacious bedrooms, including a luxurious

    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

    $474,990 Open Sat 12PM - 4PM

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

    728 Aldora Dr Unit 113, Chestertown, MD 21620

    PRICE IMPROVEMENT ON THIS QUICK MOVE-IN LUXURY VILLA! Settle by 12/31/25 and receive a FREE washer/dryer and Blinds. This stunning 4-bedroom villa offers a welcoming and functional layout with exceptional upgrades and finishes throughout. The main level features an oversized family room that opens to the kitchen and dining area—perfect for entertaining or everyday living. The upper level includes

    Agent Photo

    Terri Hill

    Builder Solutions Realty

    (410) 517-7657

    728 Aldora Dr Unit 113, Chestertown, MD 21620
  • 423 Calvert St, Chestertown, MD 21620
    423 Calvert St, Chestertown, MD 21620
    423 Calvert St, Chestertown, MD 21620
    /20

    $165,000

    • 3 Beds
    • 1.5 Baths
    • 1,136 Sq Ft

    423 Calvert St, Chestertown, MD 21620

    READY TO FINISH!!! LVP Flooring installed on 10/04/2025 on the main and upper levels. Materials, fixtures, applicances cabinetry, washer/dryer and new toilet on site and ready to install. Discover the potential of 423 Calvert Street — a two-story, 1,136 sq. ft. townhouse built in 1992 and set on a 2,006 sq. ft. lot. This 3-bedroom, 1.5-bath home has already undergone major updates in 2025,

    Barbara McCaffrey Redfin Corp

    423 Calvert St, Chestertown, MD 21620
  • 103 Landing Ln, Chestertown, MD 21620
    103 Landing Ln, Chestertown, MD 21620
    103 Landing Ln, Chestertown, MD 21620
    /69

    $559,000

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

    103 Landing Ln, Chestertown, MD 21620

    Welcome to 103 Landing Lane: a meticulously maintained 2-bedroom townhome in the desirable waterfront community of Chester River Landing. Just a short walk or bike ride into downtown Chestertown, this elegant, turn-key home offers maintenance-free living, great amenities, and easy water access to the Chester River. The welcoming foyer seamlessly flows into the rear den or office which could be

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    103 Landing Ln, Chestertown, MD 21620
  • 106 Landing Ln, Chestertown, MD 21620
    106 Landing Ln, Chestertown, MD 21620
    106 Landing Ln, Chestertown, MD 21620
    /23

    $799,900 New Construction

    • 3 Beds
    • 3.5 Baths
    • 2,092 Sq Ft

    106 Landing Ln, Chestertown, MD 21620

    Welcome to this beautifully designed 2,092 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 3.5 baths. Inside, an open-concept main level connects the great room, gourmet kitchen, and dining area—perfect for entertaining. There's also a private study, which could be used as additional space for guests.

    Julia Hilfiker Gunther-McClary Real Estate

    106 Landing Ln, Chestertown, MD 21620
  • 104 Little Harbor Way, Chestertown, MD 21620
    104 Little Harbor Way, Chestertown, MD 21620
    104 Little Harbor Way, Chestertown, MD 21620
    /22

    $849,900 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,980 Sq Ft

    104 Little Harbor Way, Chestertown, MD 21620

    Welcome to this beautifully designed 1,980 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath, large walk-in closet, and

    Julia Hilfiker Gunther-McClary Real Estate

    104 Little Harbor Way, Chestertown, MD 21620
  • 100 Metcalf Rd, Chestertown, MD 21620
    100 Metcalf Rd, Chestertown, MD 21620
    100 Metcalf Rd, Chestertown, MD 21620
    /16

    $245,000

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

    100 Metcalf Rd, Chestertown, MD 21620

    Like-New Chestertown Ranch: Pristine Condition, Ready Today! $250K Skip the construction drama! Step into this stunning, move-in-ready 3-bedroom, 2-bath ranch at 100 Metcalf Rd, Chestertown, MD 21620 for just $250,000! Your Dream Home Checklist: * NO HOA! Freedom & Savings! * One-Level Living: Easy breezy! * Open Concept: Perfect for entertaining! The heart of the home is the spectacular eat-in

    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

    $249,950

    • 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 for

    Steven Knopf Engel & Völkers Annapolis

    112 Metcalf Rd, Chestertown, MD 21620
  • 103 Metcalf Rd, Chestertown, MD 21620
    103 Metcalf Rd, Chestertown, MD 21620
    103 Metcalf Rd, Chestertown, MD 21620
    /25

    $259,900 New Construction

    • 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 this October. 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

    David Moore Real Broker, LLC

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

Townhomes for Sale in Chestertown, MD

Why Live in Chestertown

Chestertown, Maryland, is a historic community on the Chester River, known for its maritime heritage and charming downtown. Founded in 1706, Chestertown was once a bustling port and remains a popular destination for homebuyers seeking a quieter lifestyle away from larger cities like Washington or Philadelphia. The town features a mix of Victorian homes downtown and waterfront properties, with river access being a significant draw. Residents enjoy boating on the river, and many homes feature private docks. The private Chester River Yacht & Country Club offers additional amenities such as an 18-hole golf course and a marina. Local parks like Wilmer Park provide walking trails and playgrounds, while the Wayne Gilchrest Trail caters to bikers and joggers. Downtown Chestertown is pedestrian-friendly, hosting boutiques, galleries and locally owned restaurants. Annual events like the Chestertown Tea Party Festival and the Sultana Downrigging Festival celebrate the town's rich history. Washington College, a small liberal arts institution, adds to the vibrant atmosphere. The University of Maryland Shore Medical Center provides health care services, including an emergency room. Chestertown is within driving distance of Baltimore, 75 miles away, and Baltimore/Washington International Airport. With its blend of historic charm, riverfront recreation and local amenities, Chestertown offers a unique living experience.

Learn more about living in Chestertown

Home Trends in Chestertown, MD

On average, homes in Chestertown, MD sell after 51 days on the market compared to the national average of 53 days. The median sale price for homes in Chestertown, MD over the last 12 months is $365,000, up 5% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$365,000
Median Single Family Sale Price
$382,500
Median Townhouse Sale Price
$289,500
Median 1 Bedroom Sale Price
$285,000
Average Price Per Sq Ft
$216
Number of Homes for Sale
34
Last 12 months Home Sales
91
Months of Supply
4.50
Median List Price
$370,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
5%
How to Buy a Home How to Finance a Home How to Sell a Home

In Chestertown, there are currently 11 townhouses for sale, providing a range of options for prospective buyers. With townhouses priced between $165,000 to $878,000, there's a range to accomodate every budget. As of November, 2025 the median home price in Chestertown is $370,000, while the average sale price is $425,247, offering insights into the local housing market. On average, townhouses spend 51 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.

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

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