6

Chestertown, MD Open Houses

Section Image Section Image
  • 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

    $509,990 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 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

    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
    /19

    $185,000 Open Sat 1PM - 3PM

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

    423 Calvert St, Chestertown, MD 21620

    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, including new flooring, appliances, fresh paint, and a newer roof. Renovations are well underway, with all remaining materials provided, giving the next owner an incredible opportunity to add

    Barbara McCaffrey Redfin Corp

    423 Calvert St, Chestertown, MD 21620
  • 200 Washington Ave, Chestertown, MD 21620
    200 Washington Ave, Chestertown, MD 21620
    200 Washington Ave, Chestertown, MD 21620
    /35

    $745,000 Open Sat 11AM - 1PM

    • 4 Beds
    • 3.5 Baths
    • 2,917 Sq Ft

    200 Washington Ave, Chestertown, MD 21620

    Every initial showing stated “what a great house but it is priced a little high!”. The house is still GREAT! This early 20th C gem of a traditional "Four Square" has been a Chestertown STAND-OUT RESIDENCE since originally crafted by acclaimed master builder Walter Pippin. The flawless flow of its' first floor, with discreet powder room, and the abundance of windows throughout make this corner

    Richard Keaveney Cross Street Realtors LLC

    200 Washington Ave, Chestertown, MD 21620
  • 907 N Meadowview Dr, Chestertown, MD 21620
    907 N Meadowview Dr, Chestertown, MD 21620
    907 N Meadowview Dr, Chestertown, MD 21620
    /33

    $410,000 Open Sun 11AM - 1PM

    • 3 Beds
    • 2.5 Baths
    • 1,842 Sq Ft

    907 N Meadowview Dr, Chestertown, MD 21620

    JUST INSTALLED BRAND NEW CARPET! Welcome to 907 N Meadowview Drive, a beautifully maintained home in the sought-after Crestview community of Chestertown. Situated on a spacious .707-acre lot, this 3-bedroom, 2.5-bath home offers 1,842 square feet of comfortable living space.Step inside to find a bright and inviting living room anchored by a cozy pellet stove, ideal for chilly

    William Sutton Coldwell Banker Chesapeake Real Estate Company

    907 N Meadowview Dr, Chestertown, MD 21620
  • 11040 Kylie Ln, Chestertown, MD 21620
    11040 Kylie Ln, Chestertown, MD 21620
    11040 Kylie Ln, Chestertown, MD 21620
    /71

    $649,000 Open Sun 12PM - 3PM

    • 4 Beds
    • 3.5 Baths
    • 3,684 Sq Ft

    11040 Kylie Ln, Chestertown, MD 21620

    Rare lake front property in Kent County! Welcome to your serene getaway nestled on 2.62 acres of partially wooded land on Urieville Lake! This stunning 4-bedroom, 3.5-bathroom home offers the perfect blend of comfort and privacy, making it an ideal retreat for families and nature enthusiasts alike. With an option of a first floor bedroom there are currently three bedrooms on the second floor and

    Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    11040 Kylie Ln, Chestertown, MD 21620
  • 124 Char Nor Manor Blvd, Chestertown, MD 21620
    124 Char Nor Manor Blvd, Chestertown, MD 21620
    124 Char Nor Manor Blvd, Chestertown, MD 21620
    /5

    $245,000 Open House 10/18

    • 2 Beds
    • 2 Baths
    • 1,024 Sq Ft

    124 Char Nor Manor Blvd, Chestertown, MD 21620

    Welcome to 124 Char Nor Manor Blvd, a charming home tucked away on a quiet street in Chestertown. This residence offers the perfect balance of comfort, convenience, and lifestyle, all within the highly sought-after Queen Anne’s County school district.Step inside to find a warm and inviting space with high ceilings and skylights flooded with tons of natural lighting. Continue into the living

    Crystal Smith RE/MAX Executive

    124 Char Nor Manor Blvd, 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 49 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 $355,000, up 5% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$355,000
Median Single Family Sale Price
$380,000
Median Townhouse Sale Price
$263,750
Median 2 Bedroom Sale Price
$482,000
Median 1 Bedroom Sale Price
$285,000
Average Price Per Sq Ft
$220
Number of Homes for Sale
35
Last 12 months Home Sales
87
Months of Supply
4.80
Median List Price
$362,500
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 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.

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.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2025 CoStar Group