117 total properties
View 6746 Quaker Road Chestertown, MD MLS# MDKE2006022
  • Recently Listed
1 of 49
$445,000
3,371

Sq.Ft.

6746 Quaker Road

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View 222 Mount Vernon Avenue Chestertown, MD MLS# MDKE2005876
$455,000
4

Beds

2.0

Baths

1,656

Sq.Ft.

222 Mount Vernon Avenue

Chestertown, MD

Bright
Courtesy of LONG & FOSTER REAL ESTATE, INC.
View 110 Trafford Drive Chestertown, MD MLS# MDKE2005964
$475,000
4

Beds

2.1

Baths

2,880

Sq.Ft.

110 Trafford Drive

Chestertown, MD

Bright
Courtesy of RE/MAX ADVANTAGE REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 201 Greenwood Avenue Chestertown, MD MLS# MDKE2006030
$495,000
4

Beds

3.0

Baths

3,984

Sq.Ft.

201 Greenwood Avenue

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View 8620 Park Drive Chestertown, MD MLS# MDKE2005850
  • Virtual Tour
1 of 53
$499,900
4

Beds

2.1

Baths

2,524

Sq.Ft.

8620 Park Drive

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View 100 Adela Way Chestertown, MD MLS# MDKE2005636
  • Virtual Tour
1 of 71
$500,000
4

Beds

3.1

Baths

3,799

Sq.Ft.

100 Adela Way

Chestertown, MD

Bright
Courtesy of BERKSHIRE HATHAWAY HOMESERVICES PENFED REALTY
View 116 Harlan Loop Chestertown, MD MLS# MDKE2005610
$509,000
5

Beds

3.1

Baths

4,067

Sq.Ft.

116 Harlan Loop

Chestertown, MD

Bright
Courtesy of SAMSON PROPERTIES
View 218 Camelot Drive Chestertown, MD MLS# MDKE2005982
  • Virtual Tour
1 of 57
$525,000
5

Beds

3.1

Baths

3,932

Sq.Ft.

218 Camelot Drive

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER REALTY
View 216 Blakefield Drive Chestertown, MD MLS# MDQA2015520
  • New Construction with Virtual Tour
1 of 38
$579,000
4

Beds

3.0

Baths

2,400

Sq.Ft.

216 Blakefield Drive

Chestertown, MD

Bright
Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
View 206 S Water Street Chestertown, MD MLS# MDKE2006058
  • Recently Listed
1 of 45
$585,000
4

Beds

3.1

Baths

2,008

Sq.Ft.

206 S Water Street

Chestertown, MD

Bright
Courtesy of TTR SOTHEBY'S INTERNATIONAL REALTY
View 251 Devon Drive Chestertown, MD MLS# MDKE2005536
$595,000
3

Beds

2.1

Baths

3,935

Sq.Ft.

251 Devon Drive

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View 311 Devon Drive Chestertown, MD MLS# MDKE2005930
  • Virtual Tour
1 of 40
$598,000
5

Beds

3.1

Baths

3,504

Sq.Ft.

311 Devon Drive

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View 108 Little Harbor Way Chestertown, MD MLS# MDKE2005902
$635,000
Studio

Beds

0.0

Baths

108 Little Harbor Way

Chestertown, MD

Bright
Courtesy of GUNTHER-MCCLARY REAL ESTATE
View 200 Washington Avenue Chestertown, MD MLS# MDKE2005538
$695,000
4

Beds

3.1

Baths

2,917

Sq.Ft.

200 Washington Avenue

Chestertown, MD

Bright
Courtesy of CROSS STREET REALTORS LLC
View 118 Little Harbor Way # 202 Chestertown, MD MLS# MDKE2005800
$695,000
3

Beds

2.0

Baths

1,600

Sq.Ft.

118 Little Harbor Way # 202

Chestertown, MD

Bright
Courtesy of BENSON & MANGOLD, LLC
View 7844 Chester Court Chestertown, MD MLS# MDKE2005796
$745,000
4

Beds

2.1

Baths

3,248

Sq.Ft.

7844 Chester Court

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View #36 Landing Lane Chestertown, MD MLS# MDKE2005958
  • New Construction
1 of 26
$753,500
3

Beds

2.1

Baths

1,964

Sq.Ft.

#36 Landing Lane

Chestertown, MD

Bright
Courtesy of GUNTHER-MCCLARY REAL ESTATE
View #37 Landing Lane Chestertown, MD MLS# MDKE2005960
  • New Construction
1 of 24
$765,900
3

Beds

2.1

Baths

1,964

Sq.Ft.

#37 Landing Lane

Chestertown, MD

Bright
Courtesy of GUNTHER-MCCLARY REAL ESTATE
View #35 Landing Lane Chestertown, MD MLS# MDKE2005956
  • New Construction
1 of 26
$786,900
3

Beds

2.1

Baths

1,964

Sq.Ft.

#35 Landing Lane

Chestertown, MD

Bright
Courtesy of GUNTHER-MCCLARY REAL ESTATE
View 106 Landing Lane Chestertown, MD MLS# MDKE2005892
  • New Construction
1 of 24
$799,900
3

Beds

3.1

Baths

2,092

Sq.Ft.

106 Landing Lane

Chestertown, MD

Bright
Courtesy of GUNTHER-MCCLARY REAL ESTATE

Information deemed reliable but not guaranteed.

Information Deemed Reliable But Not Guaranteed. The data relating to real estate for sale on this website appears in part through the BrightMLS Broker ReciprocitySM program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Weichert, Realtors® participates, and is provided by BrightMLS through a licensing agreement.

Real estate listings held by brokerage firms other than Weichert, Realtors® are marked with the Broker Reciprocity icon (a little black house) and detailed information about each listing includes the name of the listing broker.

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.

© 2026 BrightMLS. All Rights Reserved.