Chestertown, MD Homes & Real Estate for Sale

Page 2 of 5
87 listings
234 N COLLEGE AVE, Chestertown, MD 21620
Single-Family Home For Sale

$184,900

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

#MDKE2005434 - Cummings & Co Realtors

SANDPIPER RD, Chestertown, MD 21620
Land For Sale

$9,000

  • 0.61 acre lot
SANDPIPER RD Chestertown, MD 21620

#MDKE2005542 - Coldwell Banker Chesapeake Real Estate Company

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

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

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

866 WASHINGTON AVE, Chestertown, MD 21620
Duplex For Sale

$299,000

  • 1,224 sqft |
  • 9,148 sqft lot
866 WASHINGTON AVE Chestertown, MD 21620

#MDKE2005460 - Brenton Realty Group

10715 KASOTA RD, Chestertown, MD 21620
Pending

$975,000

  • 4 bed |
  • 3 bath |
  • 3,401 sqft |
  • 0.84 acre lot
10715 KASOTA RD Chestertown, MD 21620

#MDKE2005366 - Cross Street Realtors LLC

165 CHAR NOR MANOR BLVD, Chestertown, MD 21620
Single-Family Home For Sale

$475,000

  • 4 bed |
  • 3 bath |
  • 2,258 sqft |
  • 0.35 acre lot
165 CHAR NOR MANOR BLVD Chestertown, MD 21620

#MDQA2013956 - RE/MAX Executive

206 S WATER ST, Chestertown, MD 21620
Single-Family Home For Sale

$648,750

  • 4 bed |
  • 4 bath |
  • 2,008 sqft |
  • 1,742 sqft lot
206 S WATER ST Chestertown, MD 21620

#MDKE2005362 - Doug Ashley Realtors, LLC

21217 TEXAS AVE, Chestertown, MD 21620
Rental Available

$1,600 /mo

  • 2 bed |
  • 1 bath |
  • 912 sqft |
  • 0.37 acre lot
21217 TEXAS AVE Chestertown, MD 21620

#MDKE2005432 - RE/MAX Leading Edge

26933 MALLARD RD, Chestertown, MD 21620
Single-Family Home For Sale

$625,000

  • 1,600 sqft |
  • 0.63 acre lot
26933 MALLARD RD Chestertown, MD 21620

#MDKE2005422 - Coldwell Banker Chesapeake Real Estate Company

CHURCH HILL ( LOT 2) RD, Chestertown, MD 21620
Land For Sale

$165,000

  • 5.34 acre lot
CHURCH HILL ( LOT 2) RD Chestertown, MD 21620

#MDQA2014030 - Coldwell Banker Chesapeake Real Estate Company

134 CHAR NOR MANOR BLVD, Chestertown, MD 21620
Single-Family Home For Sale

$325,000

  • 3 bed |
  • 1 bath |
  • 1,128 sqft |
  • 8,712 sqft lot
134 CHAR NOR MANOR BLVD Chestertown, MD 21620

#MDQA2013988 - Meredith Fine Properties

201 BIRCH RUN RD, Chestertown, MD 21620
Single-Family Home For Sale

$470,000

  • 3 bed |
  • 2 bath |
  • 1,588 sqft |
  • 0.41 acre lot
201 BIRCH RUN RD Chestertown, MD 21620

#MDKE2005380 - Coldwell Banker Chesapeake Real Estate Company

10674 KASOTA RD, Chestertown, MD 21620
Single-Family Home For Sale

$309,999

  • 2 bed |
  • 1 bath |
  • 1,350 sqft |
  • 0.6 acre lot
10674 KASOTA RD Chestertown, MD 21620

#MDKE2005402 - Long & Foster Real Estate, Inc.

300 HICKORY LN, Chestertown, MD 21620
Single-Family Home For Sale

$1,297,000

  • 5 bed |
  • 4 bath |
  • 3,640 sqft |
  • 21.23 acre lot
300 HICKORY LN Chestertown, MD 21620

#MDQA2013388 - Gunther-McClary Real Estate

7514 MUIRFIELD DR, Chestertown, MD 21620
Single-Family Home For Sale

$797,000

  • 3 bed |
  • 3 bath |
  • 2,522 sqft |
  • 1.83 acre lot
7514 MUIRFIELD DR Chestertown, MD 21620

#MDKE2005370 - Gunther-McClary Real Estate

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.