Chestertown, MD Homes & Real Estate for Sale

Page 4 of 4
80 listings
#35 LANDING LN, Chestertown, MD 21620
Single-Family Home For Sale

$786,900

  • 3 bed |
  • 3 bath |
  • 1,964 sqft |
#35 LANDING LN Chestertown, MD 21620

#MDKE2005956 - Gunther-McClary Real Estate

#25 LANDING LN, Chestertown, MD 21620
Single-Family Home For Sale

$1,099,900

  • 4 bed |
  • 4 bath |
  • 2,784 sqft |
#25 LANDING LN Chestertown, MD 21620

#MDKE2005954 - Gunther-McClary Real Estate

104 LANDING LN, Chestertown, MD 21620
Town Home For Sale

$813,900

  • 3 bed |
  • 4 bath |
  • 2,192 sqft |
104 LANDING LN Chestertown, MD 21620

#MDKE2005952 - Gunther-McClary Real Estate

#36 LANDING LN, Chestertown, MD 21620
Single-Family Home For Sale

$753,500

  • 3 bed |
  • 3 bath |
  • 1,964 sqft |
#36 LANDING LN Chestertown, MD 21620

#MDKE2005958 - Gunther-McClary Real Estate

#37 LANDING LN, Chestertown, MD 21620
Single-Family Home For Sale

$765,900

  • 3 bed |
  • 3 bath |
  • 1,964 sqft |
#37 LANDING LN Chestertown, MD 21620

#MDKE2005960 - Gunther-McClary Real Estate

102 LITTLE HARBOR WAY, Chestertown, MD 21620
Single-Family Home For Sale

$839,500

  • 3 bed |
  • 3 bath |
  • 1,964 sqft |
102 LITTLE HARBOR WAY Chestertown, MD 21620

#MDKE2005950 - Gunther-McClary Real Estate

311 DEVON DR, Chestertown, MD 21620
Single-Family Home

$475,000

  • 4 bed |
  • 3 bath |
  • 3,504 sqft |
  • 0.28 acre lot
311 DEVON DR Chestertown, MD 21620

#MDKE2005930 - Doug Ashley Realtors, LLC

611 CANNON ST, Chestertown, MD 21620
Single-Family Home

$275,000

  • 2 bed |
  • 2 bath |
  • 920 sqft |
611 CANNON ST Chestertown, MD 21620

#MDKE2005906 - Select Land & Homes, LLC

104 LITTLE HARBOR WAY, Chestertown, MD 21620
Single-Family Home For Sale

$849,900

  • 3 bed |
  • 3 bath |
  • 1,980 sqft |
104 LITTLE HARBOR WAY Chestertown, MD 21620

#MDKE2005894 - Gunther-McClary Real Estate

106 LANDING LN, Chestertown, MD 21620
Town Home For Sale

$799,900

  • 3 bed |
  • 4 bath |
  • 2,092 sqft |
106 LANDING LN Chestertown, MD 21620

#MDKE2005892 - Gunther-McClary Real Estate

LITTLE HARBOR WAY #1, Chestertown, MD 21620
Single-Family Home For Sale

$1,459,000

  • 3 bed |
  • 3 bath |
  • 2,231 sqft |
LITTLE HARBOR WAY #1 Chestertown, MD 21620

#MDKE2005768 - Gunther-McClary Real Estate

105 HIGH ST, Chestertown, MD 21620
Single-Family Home For Sale

$1,245,500

  • 5 bed |
  • 5 bath |
  • 3,243 sqft |
105 HIGH ST Chestertown, MD 21620

#MDKE2005890 - Coldwell Banker Chesapeake Real Estate Company

222 MOUNT VERNON AVE, Chestertown, MD 21620
Single-Family Home For Sale

$419,999

  • 4 bed |
  • 2 bath |
  • 1,656 sqft |
222 MOUNT VERNON AVE Chestertown, MD 21620

#MDKE2005876 - Long & Foster Real Estate, Inc.

8620 PARK DR, Chestertown, MD 21620
Single-Family Home For Sale

$499,900

  • 4 bed |
  • 2,524 sqft |
  • 1.37 acre lot
8620 PARK DR Chestertown, MD 21620

#MDKE2005850 - Doug Ashley Realtors, LLC

7844 CHESTER CT, Chestertown, MD 21620
Single-Family Home

$670,000

  • 4 bed |
  • 3 bath |
  • 3,248 sqft |
  • 1.01 acre lot
7844 CHESTER CT Chestertown, MD 21620

#MDKE2005796 - Doug Ashley Realtors, LLC

222 DUTCHESS RD, Chestertown, MD 21620
Single-Family Home For Sale

$320,000

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

#MDQA2014830 - Gunther-McClary Real Estate

7989 QUAKER NECK RD, Chestertown, MD 21620
Single-Family Home For Sale

$2,200,000

  • 5 bed |
  • 5 bath |
  • 4,305 sqft |
  • 0.84 acre lot
7989 QUAKER NECK RD Chestertown, MD 21620

#MDKE2005590 - Coldwell Banker Chesapeake Real Estate Company

103 LANDING LN, Chestertown, MD 21620
Town Home For Sale

$499,999

  • 2 bed |
  • 3 bath |
  • 2,100 sqft |
103 LANDING LN Chestertown, MD 21620

#MDKE2005670 - Coldwell Banker Chesapeake Real Estate Company

23043 BAY SHORE SPUR, Chestertown, MD 21620
Single-Family Home For Sale

$385,000

  • 4 bed |
  • 3 bath |
  • 2,630 sqft |
  • 1.65 acre lot
23043 BAY SHORE SPUR Chestertown, MD 21620

#MDKE2005584 - Rock Hall Properties Real Estate

LITTLE HARBOR WAY #1, Chestertown, MD 21620
Single-Family Home For Sale

$1,800,000

  • 4 bed |
  • 4 bath |
  • 3,540 sqft |
LITTLE HARBOR WAY #1 Chestertown, MD 21620

#MDKE2004992 - 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. ©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