Chestertown, MD Homes & Real Estate for Sale

Page 1 of 4
80 listings
521 N KENT ST, Chestertown, MD 21620New listing icon New - 1 day ago
Single-Family Home

$385,000

  • 3 bed |
  • 2 bath |
  • 1,934 sqft |
  • 0.4 acre lot
521 N KENT ST Chestertown, MD 21620

#MDKE2006784 - Coldwell Banker Chesapeake Real Estate Company

7680 COUNTRY CLUB LN, Chestertown, MD 21620New listing icon New - 2 days ago
Single-Family Home For Sale

$885,000

  • 5 bed |
  • 4 bath |
  • 2,639 sqft |
  • 0.81 acre lot
7680 COUNTRY CLUB LN Chestertown, MD 21620

#MDKE2006758 - Gunther-McClary Real Estate

9126 FAIRLEE RD, Chestertown, MD 21620New listing icon New - 3 days ago
Single-Family Home For Sale

$344,000

  • 3 bed |
  • 2 bath |
  • 1,216 sqft |
  • 1.66 acre lot
9126 FAIRLEE RD Chestertown, MD 21620

#MDKE2006764 - Chesapeake Real Estate Associates, LLC

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

$325,000

  • 3 bed |
  • 1 bath |
  • 1,000 sqft |
  • 0.34 acre lot
896 WASHINGTON AVE Chestertown, MD 21620

#MDKE2006750 - Coldwell Banker Chesapeake Real Estate Company

103 MAPLE AVE, Chestertown, MD 21620
Single-Family Home

$615,000

  • 4 bed |
  • 3 bath |
  • 4,536 sqft |
  • 0.27 acre lot
103 MAPLE AVE Chestertown, MD 21620

#MDKE2006676 - Coldwell Banker Chesapeake Real Estate Company

210 N QUEEN ST, Chestertown, MD 21620
Coming Soon

$735,000

  • 4 bed |
  • 3 bath |
  • 2,730 sqft |
  • 0.46 acre lot
210 N QUEEN ST Chestertown, MD 21620

#MDKE2006744 - Coldwell Banker Chesapeake Real Estate Company

22481 GOOSE HOLLOW DR, Chestertown, MD 21620
Single-Family Home For Sale

$279,900

  • 3 bed |
  • 2 bath |
  • 1,296 sqft |
  • 2 acre lot
22481 GOOSE HOLLOW DR Chestertown, MD 21620

#MDKE2006682 - Keller Williams Legacy

105 N WATER ST #2, Chestertown, MD 21620
Condominium For Sale

$475,000

  • 2 bed |
  • 2 bath |
  • 1,011 sqft |
105 N WATER ST #2 Chestertown, MD 21620

#MDKE2006680 - Northrop Realty

25750 COLLINS AVE, Chestertown, MD 21620
Single-Family Home For Sale

$468,000

  • 3 bed |
  • 2 bath |
  • 3,262 sqft |
  • 0.76 acre lot
25750 COLLINS AVE Chestertown, MD 21620

#MDKE2006546 - Doug Ashley Realtors, LLC

101 S MILL ST, Chestertown, MD 21620
Single-Family Home For Sale

$515,000

  • 2 bed |
  • 3 bath |
  • 1,476 sqft |
101 S MILL ST Chestertown, MD 21620

#MDKE2006674 - Coldwell Banker Chesapeake Real Estate Company

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

$324,900

  • 3 bed |
  • 1 bath |
  • 1,248 sqft |
  • 0.34 acre lot
517 ROUND TOP RD Chestertown, MD 21620

#MDQA2017680 - Keller Williams Flagship

201 RIVER RD, Chestertown, MD 21620
Single-Family Home

$629,900

  • 3 bed |
  • 2 bath |
  • 2,430 sqft |
  • 1 acre lot
201 RIVER RD Chestertown, MD 21620

#MDQA2017684 - Coldwell Banker Chesapeake Real Estate Company

104 CONLEY DR, Chestertown, MD 21620
Town Home For Sale

$239,900

  • 3 bed |
  • 2 bath |
  • 1,280 sqft |
104 CONLEY DR Chestertown, MD 21620

#MDKE2006686 - Cummings & Co. Realtors

221 DUTCHESS RD, Chestertown, MD 21620
Single-Family Home

$228,000

  • 3 bed |
  • 2 bath |
  • 2,260 sqft |
  • 0.34 acre lot
221 DUTCHESS RD Chestertown, MD 21620

#MDQA2017670 - Doug Ashley Realtors, LLC

202 ROYSTON SHORES RD, Chestertown, MD 21620
Single-Family Home

$1,200,000

  • 4 bed |
  • 3 bath |
  • 2,292 sqft |
  • 0.61 acre lot
202 ROYSTON SHORES RD Chestertown, MD 21620

#MDQA2017462 - Cross Street Realtors LLC

10572 WATONGA RD, Chestertown, MD 21620
Single-Family Home

$325,000

  • 3 bed |
  • 2 bath |
  • 1,404 sqft |
  • 0.35 acre lot
10572 WATONGA RD Chestertown, MD 21620

#MDKE2006644 - Serhant

104 ACORN DR, Chestertown, MD 21620
Town Home For Sale

$284,900

  • 3 bed |
  • 3 bath |
  • 1,900 sqft |
104 ACORN DR Chestertown, MD 21620

#MDKE2006668 - Cross Street Realtors LLC

234 N COLLEGE AVE, Chestertown, MD 21620
Single-Family Home For Sale

$100,000

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

#MDKE2006670 - Cummings & Co Realtors

23264 CLARISSA RD, Chestertown, MD 21620
Single-Family Home

$365,000

  • 3 bed |
  • 2 bath |
  • 1,248 sqft |
  • 0.73 acre lot
23264 CLARISSA RD Chestertown, MD 21620

#MDKE2006096 - TTR Sotheby's International Realty

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

$89,900

  • 3 bed |
  • 2 bath |
  • 2,210 sqft |
110 PROSPECT ST Chestertown, MD 21620

#MDKE2006626 - ANR Realty, 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. ©2026 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 © 2026 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.

Connect with an Agent
Get paired with a top VA-friendly agentGet an Agent