128 total properties
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
View 105 High Street Chestertown, MD MLS# MDKE2005890
$1,395,500
5

Beds

4.1

Baths

3,243

Sq.Ft.

105 High Street

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 204 Rolling Road Chestertown, MD MLS# MDKE2005896
$370,000
3

Beds

2.0

Baths

2,296

Sq.Ft.

204 Rolling Road

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
The time to sell is now! THE TIME TO SELL IS NOW!
View 112 Silver Heel Drive Chestertown, MD MLS# MDKE2005880
$369,900
5

Beds

3.1

Baths

2,615

Sq.Ft.

112 Silver Heel Drive

Chestertown, MD

Bright
Courtesy of EXP REALTY, LLC
View 10230 John Carvill Road Chestertown, MD MLS# MDKE2005716
$750,000
4

Beds

3.0

Baths

2,350

Sq.Ft.

10230 John Carvill Road

Chestertown, MD

Bright
Courtesy of SHORELINE REALTY
View 222 Mount Vernon Avenue Chestertown, MD MLS# MDKE2005876
1 of 30
OPEN HOUSE: Sunday 12/7 10:00 AM - 12:00 PM
$470,000
4

Beds

2.0

Baths

1,656

Sq.Ft.

222 Mount Vernon Avenue

Chestertown, MD

Bright
Courtesy of LONG & FOSTER REAL ESTATE, INC.
View 216 Blakefield Drive Chestertown, MD MLS# MDQA2015520
$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 304 Hadaway Drive Chestertown, MD MLS# MDKE2005848
$399,000
4

Beds

2.0

Baths

1,325

Sq.Ft.

304 Hadaway Drive

Chestertown, MD

Bright
Courtesy of CUMMINGS & CO. REALTORS
View 10121 Fairlee Road Chestertown, MD MLS# MDKE2005866
$2,350,000
6

Beds

5.0

Baths

4,954

Sq.Ft.

10121 Fairlee Road

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
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 109 S College Avenue Chestertown, MD MLS# MDKE2005818
$449,900
3

Beds

2.1

Baths

1,216

Sq.Ft.

109 S College Avenue

Chestertown, MD

Bright
Courtesy of CROSS STREET REALTORS LLC
View 303 E Campus Avenue Chestertown, MD MLS# MDKE2005756
$363,000
3

Beds

2.0

Baths

1,532

Sq.Ft.

303 E Campus Avenue

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View 7844 Chester Court Chestertown, MD MLS# MDKE2005796
$770,000
4

Beds

2.1

Baths

3,248

Sq.Ft.

7844 Chester Court

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View 10121 Fairlee Road Chestertown, MD MLS# MDKE2005852
$2,350,000
6

Beds

5.0

Baths

4,954

Sq.Ft.

10121 Fairlee Road

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 206 S Water Street Chestertown, MD MLS# MDKE2005840
$619,000
4

Beds

3.1

Baths

2,008

Sq.Ft.

206 S Water Street

Chestertown, MD

Bright
Courtesy of TTR SOTHEBY'S INTERNATIONAL REALTY
View 318 Lincoln Chestertown, MD MLS# MDKE2005842
$269,000
3

Beds

2.0

Baths

960

Sq.Ft.

318 Lincoln

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 228 S Water St Chestertown, MD MLS# MDKE2005812
  • New Construction
1 of 32
$878,000
3

Beds

3.1

Baths

2,310

Sq.Ft.

228 S Water St

Chestertown, MD

Bright
Courtesy of GUNTHER-MCCLARY REAL ESTATE
View 8750 Georgetown Road Chestertown, MD MLS# MDKE2005834
$339,000
3

Beds

2.0

Baths

1,900

Sq.Ft.

8750 Georgetown Road

Chestertown, MD

Bright
Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
View 411 Greenwood Avenue Chestertown, MD MLS# MDKE2005824
$419,000
3

Beds

2.1

Baths

1,676

Sq.Ft.

411 Greenwood Avenue

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 127 Wood Duck Lane Chestertown, MD MLS# MDQA2015154
$215,000
3

Beds

2.0

Baths

1,666

Sq.Ft.

127 Wood Duck Lane

Chestertown, MD

Bright
Courtesy of RE/MAX POINT REALTY

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.

© 2025 BrightMLS. All Rights Reserved.