10

Chestertown, MD Homes for Sale under $200,000

Section Image
  • 108 Pine St, Chestertown, MD 21620
    108 Pine St, Chestertown, MD 21620
    /2

    $115,000

    $28K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 910 Sq Ft

    108 Pine St, Chestertown, MD 21620

    Previous Buyer failed to perform - Your opportunity has come around again - Don't miss out this time. FULL RENOVATION PROJECT - Prime Chestertown Location Priced for Immediate Equity Creation. This 3-bedroom, 1-bath single-family home at $115,000 represents a clear value-add opportunity in one of Chestertown’s most “walkable” corridors. With estimated renovation investment of $60K-$80K+,

    David Moore Real Broker, LLC

    108 Pine St, Chestertown, MD 21620
  • 116 N Cross St, Chestertown, MD 21620
    116 N Cross St, Chestertown, MD 21620
    116 N Cross St, Chestertown, MD 21620
    /9

    $109,999

    • Land
    • 7,840 Sq Ft
    • $611,106 per Acre

    116 N Cross St, Chestertown, MD 21620

    Great opportunity in the heart of Chestertown. This downtown commercial lot offers incredible potential just steps from established businesses and local amenities. Public sewer is available and accessible, making development that much more convenient. Positioned next to a professional office building, the property benefits from strong daily visibility with both foot and vehicle traffic passing

    Hayley Norris Select Land & Homes, LLC

    116 N Cross St, Chestertown, MD 21620
  • 144 Prospect St, Chestertown, MD 21620
    144 Prospect St, Chestertown, MD 21620
    144 Prospect St, Chestertown, MD 21620
    /18

    $179,000

    • 2 Beds
    • 1.5 Baths
    • 1,082 Sq Ft

    144 Prospect St, Chestertown, MD 21620

    Great opportunity to own a small cottage in Chestertown. Right next to, and with direct access to the walking trails, this end of road 2 bedroom home comes with an extra lot, currently used for parking, but could also possibly be built on. Buyer to verify with county

    Michele Palmer Doug Ashley Realtors, LLC

    144 Prospect St, Chestertown, MD 21620
  • 109 2nd St, Chestertown, MD 21620
    109 2nd St, Chestertown, MD 21620
    /2

    $150,000

    • Land
    • 1.8 Acres
    • $83,333 per Acre

    109 2nd St, Chestertown, MD 21620

    Nestled in one of the most beautiful and peaceful areas of Queen Anne’s County, this serene wooded lot has already been perc approved and offers the perfect blend of privacy and convenience. The lot is surrounded by mature trees and feels secluded and tranquil while still being just 9 minutes from Historic Chestertown. Convenient access to Routes 213 and 544 makes travel to Centreville, Easton,

    Katie Stecklair Cross Street Realtors LLC

    109 2nd St, Chestertown, MD 21620
  • 127 Wood Duck Ln, Chestertown, MD 21620
    127 Wood Duck Ln, Chestertown, MD 21620
    127 Wood Duck Ln, Chestertown, MD 21620
    /23

    $138,000

    • 3 Beds
    • 2 Baths
    • 1,666 Sq Ft

    127 Wood Duck Ln, Chestertown, MD 21620

    Well priced 3 bedroom, 2 bath double wide in Duck Neck, Queen Annes County situated on a half an acre and shed , man cave and car ports included. House has a metal roof. Close to the Chester River and minutes from Deep Landing and Chestertown. The property does need work, but some sweat equity would result in a really nice place! Property can be accessed on Wood Duck Lane or Snyder Lane. The

    Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

    127 Wood Duck Ln, Chestertown, MD 21620
  • 0 Caulks Field Rd Unit MDKE2005120, Chestertown, MD 21620
    0 Caulks Field Rd Unit MDKE2005120, Chestertown, MD 21620
    0 Caulks Field Rd Unit MDKE2005120, Chestertown, MD 21620
    /8

    $150,000

    • Land
    • 2 Acres
    • $75,000 per Acre

    0 Caulks Field Rd Unit MDKE2005120, Chestertown, MD 21620

    Sebrin Adem RE/MAX Allegiance

    0 Caulks Field Rd Unit MDKE2005120, Chestertown, MD 21620
  • 423 Calvert St, Chestertown, MD 21620
    423 Calvert St, Chestertown, MD 21620
    423 Calvert St, Chestertown, MD 21620
    /30

    $185,000

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

    423 Calvert St, Chestertown, MD 21620

    Fully renovated from top to bottom, this charming 3-bedroom, 1.5-bath townhome in the heart of downtown Chestertown offers the perfect blend of modern updates and convenience. Step inside to find new flooring, new carpet, fresh paint throughout, updated molding, and a beautifully renovated kitchen featuring white cabinetry, new countertops, and new appliances. Both bathrooms have been completely

    Ashley Earle Compass

    423 Calvert St, Chestertown, MD 21620
  • 0 Georgetown Rd SE Unit MDKE2005076, Chestertown, MD 21620
    0 Georgetown Rd SE Unit MDKE2005076, Chestertown, MD 21620
    0 Georgetown Rd SE Unit MDKE2005076, Chestertown, MD 21620
    /3

    $150,000

    • Land
    • 2 Acres
    • $75,000 per Acre

    0 Georgetown Rd SE Unit MDKE2005076, Chestertown, MD 21620

    Beautiful 2-Acre Lot – Build Your Dream Home! Come and experience the charm of this picturesque 2-acre lot, perfectly priced and ready for your dream home. Nestled among scenic farms and mature trees, this serene setting offers the perfect blend of privacy and natural beauty.Located just minutes from the water, you'll enjoy easy access to nearby Tolchester Beach—only about 2 miles west—and

    Sebrin Adem RE/MAX Allegiance

    0 Georgetown Rd SE Unit MDKE2005076, Chestertown, MD 21620
  • 0 Round Top Rd, Chestertown, MD 21620
    0 Round Top Rd, Chestertown, MD 21620
    0 Round Top Rd, Chestertown, MD 21620
    /23

    $200,000

    • Land
    • 5.81 Acres
    • $34,423 per Acre

    0 Round Top Rd, Chestertown, MD 21620

    This is a unique opportunity to invest in cleared and level acreage just off one of the Eastern Shore's commercial corridors and a few minutes from Downtown Chestertown. Suburban Commercial Zoning allows for a variety of possible uses.

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    0 Round Top Rd, Chestertown, MD 21620
  • 117 N Water St Unit 1B, Chestertown, MD 21620
    117 N Water St Unit 1B, Chestertown, MD 21620
    117 N Water St Unit 1B, Chestertown, MD 21620
    /20

    $200,000

    • 1 Bed
    • 1 Bath
    • 700 Sq Ft

    117 N Water St Unit 1B, Chestertown, MD 21620

    117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects

    Liddy Campbell TTR Sotheby's International Realty

    117 N Water St Unit 1B, Chestertown, MD 21620
Maryland Kent County Chestertown

Real Estate & Homes in Chestertown, MD under $200,000

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 $370,000, consistent with the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$370,000
Median Single Family Sale Price
$398,000
Median Townhouse Sale Price
$264,900
Median 2 Bedroom Sale Price
$375,000
Median 1 Bedroom Sale Price
$285,000
Average Price Per Sq Ft
$210
Number of Homes for Sale
37
Last 12 months Home Sales
101
Months of Supply
4.40
Median List Price
$377,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
0%
How to Buy a Home How to Finance a Home How to Sell a Home

In Chestertown, you'll find a diverse selection of properties with 10 homes for sale under $200,000, catering to budget-conscious buyers seeking affordable housing solutions. Whether you're a first-time homebuyer in search of a cozy starter home or an investor eyeing a promising opportunity, these affordable homes provide a gateway into the real estate market in Chestertown, MD.

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 © 2026 CoStar Group