Chestertown, MD Homes & Real Estate for Sale

Page 1 of 8
142 listings
143 CHAR NOR MANOR BLVD, Chestertown, MD 21620New listing icon New - 16 hours ago
Coming Soon

$868,000

  • 3 bed |
  • 3 bath |
  • 2,073 sqft |
  • 1.08 acre lot
143 CHAR NOR MANOR BLVD Chestertown, MD 21620

#MDQA2014274 - Redfin Corp

SANDPIPER RD, Chestertown, MD 21620New listing icon New - 16 hours ago
Land For Sale

$9,000

  • 0.61 acre lot
SANDPIPER RD Chestertown, MD 21620

#MDKE2005542 - Coldwell Banker Chesapeake Real Estate Company

907 N MEADOWVIEW DR, Chestertown, MD 21620New listing icon New - 16 hours ago
Coming Soon

$440,000

  • 3 bed |
  • 3 bath |
  • 1,842 sqft |
  • 0.71 acre lot
907 N MEADOWVIEW DR Chestertown, MD 21620

#MDKE2005540 - Coldwell Banker Chesapeake Real Estate Company

251 DEVON DR, Chestertown, MD 21620New listing icon New - 16 hours ago
Single-Family Home For Sale

$595,000

  • 3 bed |
  • 3 bath |
  • 3,935 sqft |
  • 0.64 acre lot
251 DEVON DR Chestertown, MD 21620

#MDKE2005536 - Doug Ashley Realtors, LLC

234 N COLLEGE AVE, Chestertown, MD 21620New listing icon New - 16 hours ago
Single-Family Home For Sale

$199,900

  • 2 bed |
  • 1 bath |
  • 1,296 sqft |
  • 3,920 sqft lot
234 N COLLEGE AVE Chestertown, MD 21620

#MDKE2005434 - Cummings & Co Realtors

9194 N BAYVIEW AVE, Chestertown, MD 21620New listing icon New - 1 day ago
Single-Family Home For Sale

$698,000

  • 2 bed |
  • 2 bath |
  • 1,460 sqft |
  • 0.32 acre lot
9194 N BAYVIEW AVE Chestertown, MD 21620

#MDKE2005488 - Gunther-McClary Real Estate

9190 N BAYVIEW AVE, Chestertown, MD 21620New listing icon New - 3 days ago
Manufactured Home For Sale

$319,500

  • 2 bed |
  • 1 bath |
  • 1,160 sqft |
  • 7,841 sqft lot
9190 N BAYVIEW AVE Chestertown, MD 21620

#MDKE2005442 - Select Land & Homes, LLC

ELM RD, Chestertown, MD 21620New listing icon New - 3 days ago
Land For Sale

$12,675

  • 9,583 sqft lot
ELM RD Chestertown, MD 21620

#MDKE2005532 - Cross Street Realtors LLC

141 PROSPECT ST, Chestertown, MD 21620
Single-Family Home For Sale

$175,000

  • 4 bed |
  • 2 bath |
  • 1,156 sqft |
  • 7,841 sqft lot
141 PROSPECT ST Chestertown, MD 21620

#MDKE2005504 - Cross Street Realtors LLC

23370 LOVELY LN, Chestertown, MD 21620
Manufactured Home For Sale

$309,000

  • 3 bed |
  • 2 bath |
  • 1,680 sqft |
  • 0.5 acre lot
23370 LOVELY LN Chestertown, MD 21620

#MDKE2005510 - Coldwell Banker Chesapeake Real Estate Company

600 ROSIN DR, Chestertown, MD 21620
Coming Soon

$424,000

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

#MDQA2014374 - Cross Street Realtors LLC

112 METCALF RD, Chestertown, MD 21620
Coming Soon

$280,000

  • 3 bed |
  • 2 bath |
  • 1,280 sqft |
  • 3,049 sqft lot
112 METCALF RD Chestertown, MD 21620

#MDKE2005498 - Engel & Volkers Annapolis

108 S KENT ST, Chestertown, MD 21620
Coming Soon

$325,000

  • 1 bed |
  • 2 bath |
  • 936 sqft |
  • 1,742 sqft lot
108 S KENT ST Chestertown, MD 21620

#MDKE2005496 - Coldwell Banker Chesapeake Real Estate Company

205 PINE ST, Chestertown, MD 21620
Single-Family Home For Sale

$325,000

  • 3 bed |
  • 2 bath |
  • 2,212 sqft |
  • 0.29 acre lot
205 PINE ST Chestertown, MD 21620

#MDKE2005492 - Davis Real Estate, Inc.

866 WASHINGTON AVE, Chestertown, MD 21620
Single-Family Home For Sale

$299,000

  • 3 bed |
  • 2 bath |
  • 1,224 sqft |
  • 9,148 sqft lot
866 WASHINGTON AVE Chestertown, MD 21620

#MDKE2005480 - Brenton Realty Group

COGAR RD, Chestertown, MD 21620
Land For Sale

$15,000

  • 0.34 acre lot
COGAR RD Chestertown, MD 21620

#MDKE2005472 - Compass

TONOPAH RD, Chestertown, MD 21620
Land For Sale

$15,000

  • 0.34 acre lot
TONOPAH RD Chestertown, MD 21620

#MDKE2005470 - Compass

201 BOUNDARY AVE, Chestertown, MD 21620
Coming Soon

$470,000

  • 4 bed |
  • 3 bath |
  • 3,096 sqft |
  • 0.54 acre lot
201 BOUNDARY AVE Chestertown, MD 21620

#MDQA2014272 - Coldwell Banker Chesapeake Real Estate Company

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

$1,100,000

  • 3 bed |
  • 2 bath |
  • 2,600 sqft |
  • 0.91 acre lot
492 PEAR TREE POINT RD Chestertown, MD 21620

#MDQA2013108 - Meredith Fine Properties

7425 WILKINS LN, Chestertown, MD 21620
Pending

$320,000

  • 3 bed |
  • 2 bath |
  • 1,341 sqft |
  • 0.34 acre lot
7425 WILKINS LN Chestertown, MD 21620

#MDKE2005418 - Realty ONE Group Unlimited

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.