Chestertown, MD Homes & Real Estate for Sale

Page 1 of 5
95 listings
101 BIRCH RUN RD, Chestertown, MD 21620New listing icon New - Just listed!
Single-Family Home For Sale

$525,000

  • 3 bed |
  • 2 bath |
  • 1,961 sqft |
  • 0.42 acre lot
101 BIRCH RUN RD Chestertown, MD 21620

#MDKE2005810 - Remax Vision

127 WOOD DUCK LN, Chestertown, MD 21620New listing icon New - 2 days ago
Manufactured Home For Sale

$215,000

  • 3 bed |
  • 2 bath |
  • 1,666 sqft |
  • 0.53 acre lot
127 WOOD DUCK LN Chestertown, MD 21620

#MDQA2015154 - RE/MAX Point Realty

10050 FORREST LN, Chestertown, MD 21620New listing icon New - 2 days ago
Single-Family Home For Sale

$899,000

  • 4 bed |
  • 2 bath |
  • 1,820 sqft |
  • 5.05 acre lot
10050 FORREST LN Chestertown, MD 21620

#MDKE2005792 - Coldwell Banker Chesapeake Real Estate Company

222 DUTCHESS RD, Chestertown, MD 21620New listing icon New - 3 days ago
Coming Soon

$320,000

  • 3 bed |
  • 2 bath |
  • 1,096 sqft |
  • 0.67 acre lot
222 DUTCHESS RD Chestertown, MD 21620

#MDQA2014830 - Gunther-McClary Real Estate

206 VALLEY, Chestertown, MD 21620
Single-Family Home For Sale

$639,900

  • 4 bed |
  • 2 bath |
  • 2,869 sqft |
  • 0.81 acre lot
206 VALLEY Chestertown, MD 21620

#MDKE2005762 - Coldwell Banker Chesapeake Real Estate Company

107 MALONE AVE, Chestertown, MD 21620
Single-Family Home For Sale

$305,000

  • 3 bed |
  • 1 bath |
  • 1,200 sqft |
  • 0.35 acre lot
107 MALONE AVE Chestertown, MD 21620

#MDKE2005764 - Douglas Realty LLC

492 PEAR TREE POINT RD, Chestertown, MD 21620
Coming Soon

$920,000

  • 3 bed |
  • 2 bath |
  • 2,632 sqft |
  • 0.91 acre lot
492 PEAR TREE POINT RD Chestertown, MD 21620

#MDQA2015126 - Coldwell Banker Chesapeake Real Estate Company

600 ROSIN DR, Chestertown, MD 21620
Single-Family Home For Sale

$424,000

  • 3 bed |
  • 2 bath |
  • 1,300 sqft |
  • 0.51 acre lot
600 ROSIN DR Chestertown, MD 21620

#MDQA2014896 - Doug Ashley Realtors, LLC

221 OLD BRIDGE RD, Chestertown, MD 21620
Single-Family Home For Sale

$369,900

  • 3 bed |
  • 2 bath |
  • 1,851 sqft |
  • 0.51 acre lot
221 OLD BRIDGE RD Chestertown, MD 21620

#MDQA2014888 - TTR Sotheby's International Realty

8833 GEORGETOWN RD, Chestertown, MD 21620
Single-Family Home For Sale

$314,000

  • 4 bed |
  • 2 bath |
  • 1,625 sqft |
  • 0.39 acre lot
8833 GEORGETOWN RD Chestertown, MD 21620

#MDKE2005766 - Coldwell Banker Chesapeake Real Estate Company

CLARISSA RD, Chestertown, MD 21620
Land For Sale

$10,000

  • 0.34 acre lot
CLARISSA RD Chestertown, MD 21620

#MDKE2005786 - Samson Properties

126 METCALF RD, Chestertown, MD 21620
Single-Family Home For Sale

$230,000

  • 3 bed |
  • 2 bath |
  • 1,140 sqft |
126 METCALF RD Chestertown, MD 21620

#MDKE2005734 - Taylor Properties

423 CALVERT ST, Chestertown, MD 21620
Town Home For Sale

$185,000

  • 3 bed |
  • 2 bath |
  • 1,136 sqft |
423 CALVERT ST Chestertown, MD 21620

#MDKE2005718 - Redfin Corp

110 TUXEDO RD, Chestertown, MD 21620
Single-Family Home For Sale

$275,000

  • 3 bed |
  • 3 bath |
  • 1,664 sqft |
  • 0.34 acre lot
110 TUXEDO RD Chestertown, MD 21620

#MDQA2014816 - Cummings & Co. Realtors

404 SPRING RD, Chestertown, MD 21620
Land For Sale

$19,500

  • 0.99 acre lot
404 SPRING RD Chestertown, MD 21620

#MDQA2014990 - The Parker Group

10761 KASOTA RD, Chestertown, MD 21620
Single-Family Home For Sale

$895,000

  • 3 bed |
  • 3 bath |
  • 2,582 sqft |
  • 0.48 acre lot
10761 KASOTA RD Chestertown, MD 21620

#MDKE2005698 - Coldwell Banker Chesapeake Real Estate Company

7653 BROAD NECK RD, Chestertown, MD 21620
Single-Family Home For Sale

$375,000

  • 4 bed |
  • 3 bath |
  • 1,790 sqft |
  • 0.91 acre lot
7653 BROAD NECK RD Chestertown, MD 21620

#MDKE2005742 - Benson & Mangold, LLC

517 HIGH ST, Chestertown, MD 21620
Triplex For Sale

$389,900

  • 1,728 sqft |
517 HIGH ST Chestertown, MD 21620

#MDKE2005736 - L. C. Parker Real Estate

221 RICHARD DR, Chestertown, MD 21620
Pending

$385,000

  • 2 bed |
  • 3 bath |
  • 1,711 sqft |
  • 0.34 acre lot
221 RICHARD DR Chestertown, MD 21620

#MDKE2005680 - TTR Sotheby's International Realty

FAIRLEE-MELITOTA RD, Chestertown, MD 21620
Coming Soon

$50,000

  • 0.5 acre lot
FAIRLEE-MELITOTA RD Chestertown, MD 21620

#MDKE2005726 - Chesapeake Real Estate Associates, LLC

Presented by James Mark Wilson - Veterans United Realty

Veterans United Homefront
IDX Information Deemed Reliable But Not Guaranteed. The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which participates, and is provided by BRIGHT through a licensing agreement.

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on this website may no longer be available because they are under contract, have sold or are no longer being offered for sale. Some real estate firms do not participate in IDX and their listings do not appear on this website. Some properties listed with participating firms do not appear on this website at the request of the seller. This home sale information is not to be construed as an appraisal and may not be used as such for any purpose.

BRIGHT MLS is the (or a) provider of this home sale information and has compiled content from various sources. Some properties represented may not have actually sold due to reporting errors. ©2025 BrightMLS. All rights reserved. Data displayed may be a portion of, and not a complete set of all listings published in the MLS.

For questions call 1-833-252-8030

Copyright © 2025 Veterans United Realty and Did You Serve, LLC. Homefront.com is NOT affiliated with any government agencies, including the VA. Homefront.com is a service of Did You Serve, LLC. Veterans United and the Veterans United House logo are registered trademarks of Mortgage Research Center, LLC, used under license agreement. Terms of Use.