Chestertown, MD Homes & Real Estate for Sale

Page 2 of 8
144 listings
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

128 N QUEEN ST #3, Chestertown, MD 21620
Rental Available

$1,450 /mo

  • 1 bed |
  • 1 bath |
  • 900 sqft |
  • 6,098 sqft lot
128 N QUEEN ST #3 Chestertown, MD 21620

#MDKE2005464 - Brenton Realty Group

304 HILLTOP LN, Chestertown, MD 21620
Town Home For Sale

$209,900

  • 3 bed |
  • 3 bath |
  • 1,199 sqft |
  • 2,178 sqft lot
304 HILLTOP LN Chestertown, MD 21620

#MDKE2005440 - Doug Ashley Realtors, LLC

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

$64,890

  • 2 bed |
  • 1 bath |
  • 910 sqft |
  • 2,614 sqft lot
132 PROSPECT ST Chestertown, MD 21620

#MDKE2005444 - ANR Realty, LLC

206 SILVER HEEL DR, Chestertown, MD 21620
Pending

$375,000

  • 5 bed |
  • 4 bath |
  • 2,302 sqft |
  • 4,356 sqft lot
206 SILVER HEEL DR Chestertown, MD 21620

#MDKE2005338 - Samson Properties

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

$499,000

  • 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

$495,000

  • 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

206 BARROLL DR, Chestertown, MD 21620
Single-Family Home For Sale

$480,000

  • 3 bed |
  • 2 bath |
  • 1,820 sqft |
  • 0.34 acre lot
206 BARROLL DR Chestertown, MD 21620

#MDKE2005094 - Cross Street Realtors LLC

21317 PERSIMMON DR, Chestertown, MD 21620
Town Home For Sale

$195,000

  • 2 bed |
  • 1 bath |
  • 1,269 sqft |
  • 3,049 sqft lot
21317 PERSIMMON DR Chestertown, MD 21620

#MDKE2005356 - Doug Ashley Realtors, LLC

10578 TONOPAH RD, Chestertown, MD 21620
Pending

$335,000

  • 3 bed |
  • 3 bath |
  • 1,500 sqft |
  • 0.35 acre lot
10578 TONOPAH RD Chestertown, MD 21620

#MDKE2005352 - RE/MAX Executive

925 ROUND TOP RD, Chestertown, MD 21620
Single-Family Home For Sale

$300,000

  • 3 bed |
  • 1 bath |
  • 1,056 sqft |
  • 0.34 acre lot
925 ROUND TOP RD Chestertown, MD 21620

#MDQA2013044 - TTR Sotheby's International Realty

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.