Chestertown, MD Homes & Real Estate for Sale

Page 1 of 5
94 listings
23043 BAY SHORE SPUR, Chestertown, MD 21620New listing icon New - 14 hours ago
Coming Soon

$395,000

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

#MDKE2005584 - Rock Hall Properties Real Estate

100 METCALF RD, Chestertown, MD 21620New listing icon New - 14 hours ago
Coming Soon

$255,000

  • 3 bed |
  • 2 bath |
  • 1,140 sqft |
  • 6,098 sqft lot
100 METCALF RD Chestertown, MD 21620

#MDKE2005634 - Bayside Realty

127 CHAR NOR MANOR BLVD, Chestertown, MD 21620New listing icon New - 14 hours ago
Single-Family Home For Sale

$329,900

  • 2 bed |
  • 1 bath |
  • 832 sqft |
  • 10,454 sqft lot
127 CHAR NOR MANOR BLVD Chestertown, MD 21620

#MDQA2014664 - Iron Valley Real Estate of Central PA

7483 SHORTALL ST, Chestertown, MD 21620New listing icon New - 14 hours ago
Single-Family Home For Sale

$305,000

  • 3 bed |
  • 2 bath |
  • 1,232 sqft |
  • 0.34 acre lot
7483 SHORTALL ST Chestertown, MD 21620

#MDKE2005616 - RE/MAX Executive

8978 ORCHARD DR, Chestertown, MD 21620New listing icon New - 14 hours ago
Single-Family Home For Sale

$675,000

  • 4 bed |
  • 3 bath |
  • 3,820 sqft |
  • 1.83 acre lot
8978 ORCHARD DR Chestertown, MD 21620

#MDKE2005500 - TTR Sotheby's International Realty

24415 CHESTERTOWN RD, Chestertown, MD 21620New listing icon New - 1 day ago
Single-Family Home For Sale

$279,900

  • 2 bed |
  • 1 bath |
  • 1,110 sqft |
  • 1 acre lot
24415 CHESTERTOWN RD Chestertown, MD 21620

#MDKE2005630 - TTR Sotheby's International Realty

7989 QUAKER NECK RD, Chestertown, MD 21620New listing icon New - 1 day ago
Coming Soon

$2,750,000

  • 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

225 DUKE OF KENT ST, Chestertown, MD 21620New listing icon New - 2 days ago
Coming Soon

$399,900

  • 3 bed |
  • 3 bath |
  • 1,850 sqft |
  • 0.46 acre lot
225 DUKE OF KENT ST Chestertown, MD 21620

#MDQA2014684 - Coldwell Banker Chesapeake Real Estate Company

105 PARMA RD, Chestertown, MD 21620
Coming Soon

$326,500

  • 3 bed |
  • 2 bath |
  • 1,232 sqft |
  • 0.34 acre lot
105 PARMA RD Chestertown, MD 21620

#MDQA2014652 - Benson & Mangold, LLC

224 VALLEY RD, Chestertown, MD 21620
Single-Family Home For Sale

$450,000

  • 3 bed |
  • 2 bath |
  • 1,886 sqft |
  • 0.37 acre lot
224 VALLEY RD Chestertown, MD 21620

#MDKE2005546 - Cross Street Realtors LLC

116 HARLAN LOOP, Chestertown, MD 21620
Single-Family Home For Sale

$538,000

  • 5 bed |
  • 4 bath |
  • 4,067 sqft |
  • 0.26 acre lot
116 HARLAN LOOP Chestertown, MD 21620

#MDKE2005610 - Samson Properties

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

$745,000

  • 3 bed |
  • 4 bath |
  • 2,492 sqft |
  • 8,712 sqft lot
110 S MILL ST Chestertown, MD 21620

#MDKE2005558 - Gunther-McClary Real Estate

104 MAPLE AVE, Chestertown, MD 21620
Rental Available

$2,175 /mo

  • 3 bed |
  • 2 bath |
  • 1,200 sqft |
  • 10,454 sqft lot
104 MAPLE AVE Chestertown, MD 21620

#MDKE2005596 - Real Broker, LLC - Annapolis

200 FEY RD, Chestertown, MD 21620
Single-Family Home For Sale

$374,900

  • 3 bed |
  • 2 bath |
  • 1,572 sqft |
  • 0.48 acre lot
200 FEY RD Chestertown, MD 21620

#MDQA2014600 - Long & Foster Real Estate, Inc.

302 PARK ROW #OFFICE 2, Chestertown, MD 21620
Commercial Property

$600

302 PARK ROW #OFFICE 2 Chestertown, MD 21620

#MDKE2005598 - Chesapeake Real Estate Associates, LLC

103 ADELA WAY, Chestertown, MD 21620
Single-Family Home For Sale

$615,000

  • 4 bed |
  • 4 bath |
  • 5,576 sqft |
  • 10,454 sqft lot
103 ADELA WAY Chestertown, MD 21620

#MDKE2005594 - Douglas Realty LLC

No photos available for BUCK NECK LANDING RD, Chestertown, MD 21620
Land For Sale

$10,000

  • 0.55 acre lot
BUCK NECK LANDING RD Chestertown, MD 21620

#MDKE2005586 - Rosendale Realty

492 PEAR TREE POINT RD, Chestertown, MD 21620
Single-Family Home For Sale

$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

907 N MEADOWVIEW DR, Chestertown, MD 21620
Single-Family Home For Sale

$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

7729 COUNTRY CLUB LN, Chestertown, MD 21620
Single-Family Home For Sale

$635,000

  • 3 bed |
  • 3 bath |
  • 2,280 sqft |
  • 0.68 acre lot
7729 COUNTRY CLUB LN Chestertown, MD 21620

#MDKE2005552 - Cross Street Realtors 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. ©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.