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21 Properties Available In 21620
- Newest Listings
$39,000
Vacant Land
CLOQUET RD, Chestertown, MD 21620
Largest privately held parcel in Chesapeake Landing. 8 Lots each more than 10,000 sq ft. for a total 1.51 acres. Tax map...
MLS# MDKE2005966
Listed by Berkshire Hathaway HomeServices Homesale Realty
$598,000
Single Family Home
311 DEVON DR, Chestertown, MD 21620
311 Devon Drive is located in Coventry Farms; and being located within the Chestertown town limits offers town utilities...
MLS# MDKE2005930
Listed by Doug Ashley Realtors, LLC
$1,459,000
Condo
LITTLE HARBOR WAY #1, Chestertown, MD 21620
**To be built! Welcome to this beautifully designed 2,231 sq ft home in Chester River Landing, offering modern comfort, ...
MLS# MDKE2005768
Listed by Gunther-McClary Real Estate
$369,900
Single Family Home
112 SILVER HEEL DR, Chestertown, MD 21620
Welcome to this stunning 2023 built home — a move-in ready, three-story residence offering 5 bedrooms and 3.5 baths acro...
MLS# MDKE2005880
Listed by EXP Realty, LLC
$363,000
Single Family Home
303 E CAMPUS AVE, Chestertown, MD 21620
Charming Brick Rancher in the Heart of Chestertown<br><br>Discover this classic brick rancher nestled in one of Chestert...
MLS# MDKE2005756
Listed by Doug Ashley Realtors, LLC
$419,000
Single Family Home
411 GREENWOOD AVE, Chestertown, MD 21620
Experience the best of in-town Chestertown living in this custom-built single-level home! The open floor plan features a...
MLS# MDKE2005824
Listed by Coldwell Banker Chesapeake Real Estate Company
$499,900
Single Family Home
8620 PARK DR, Chestertown, MD 21620
Two Story Colonial on 1.37+/- acre lot, rectangular 200 x 300 ft. Approximately 2,700 sq ft. of living area in house (e...
MLS# MDKE2005850
Listed by Doug Ashley Realtors, LLC
$770,000
Single Family Home
7844 CHESTER CT, Chestertown, MD 21620
Beautifully Updated Home in a Serene Setting!<br><br>Welcome to this stunning home filled with thoughtful improvements a...
MLS# MDKE2005796
Listed by Doug Ashley Realtors, LLC
$499,999
Single Family Home
101 BIRCH RUN RD, Chestertown, MD 21620
Welcome to 101 Birch Run Rd., Chestertown, MD! <br>3 Bedrooms | 2 Full Baths | Oversized 2-Car Garage | .42 Acres<br>Dis...
MLS# MDKE2005810
Listed by Remax Vision
$290,000
Single Family Home
107 MALONE AVE, Chestertown, MD 21620
Welcome to 107 Malone Ave. in the friendly community of Foxley Manor....A Great place to call "HOME"! This lovely 3 Bed...
MLS# MDKE2005764
Listed by Douglas Realty LLC
$135,000
Townhouse
423 CALVERT ST, Chestertown, MD 21620
This property is primed and ready for your finishing touches—materials included! Enjoy the convenience of being just ste...
MLS# MDKE2005718
Listed by Redfin Corp
$375,000
Single Family Home
7653 BROAD NECK RD, Chestertown, MD 21620
Recently and thoroughly renovated, charming and spacious 4 bedroom 3 bathroom home located only about 6 miles from Ches...
MLS# MDKE2005742
Listed by Benson & Mangold, LLC
$515,000
Single Family Home
100 ADELA WAY, Chestertown, MD 21620
*Days on Market Reporting Incorrectly- Property listed Oct 30, 2025* <br>Nestled just outside of historic Chestertown, m...
MLS# MDKE2005636
Listed by Berkshire Hathaway HomeServices PenFed Realty
$2,500,000
Single Family Home
7989 QUAKER NECK RD, Chestertown, MD 21620
Price Improvement! Spectacular waterfront on the Chester River!! Words can't describe the uniqueness of this property. ...
MLS# MDKE2005590
Listed by Coldwell Banker Chesapeake Real Estate Company
$179,000
Townhouse
21316 PERSIMMON DR, Chestertown, MD 21620
Back on the market through no fault of the sellers. Home inspection went well. Two bedroom, one bath townhome with a...
MLS# MDKE2005624
Listed by Doug Ashley Realtors, LLC
$350,000
Single Family Home
10751 MILLBROOK DR, Chestertown, MD 21620
Chesapeake Landing - This home is featured on a corner lot with large living space and additional space above the detach...
MLS# MDKE2005652
Listed by Long & Foster Real Estate, Inc.
$409,900
Single Family Home
165 CHAR NOR MANOR BLVD, Chestertown, MD 21620
Chester River Views from Every Angle!<br>Welcome to this stunning Colonial located on the Queen Anne's County side of Ch...
MLS# MDQA2013956
Listed by RE/MAX Executive
$1,800,000
Condo
LITTLE HARBOR WAY #1, Chestertown, MD 21620
**Price increase due to the home's expanded footprint—over 1,200 additional square feet!**<br><br>**To be built! Welcome...
MLS# MDKE2004992
Listed by Gunther-McClary Real Estate
$344,900
Single Family Home
109 WILTON RD, Chestertown, MD 21620
Welcome to this charming 3-bedroom, 2-bathroom rancher, offering the perfect blend of comfort and convenience with one-l...
MLS# MDQA2011782
Listed by Chesapeake Real Estate Associates, LLC
$649,000
Single Family Home
11040 KYLIE LN, Chestertown, MD 21620
Rare lake front property in Kent County! Welcome to your serene getaway nestled on 2.62 acres of partially wooded land o...
MLS# MDKE2004586
Listed by Coldwell Banker Chesapeake Real Estate Company
$375,000
Commercial
860 & 870 HIGH ST, Chestertown, MD 21620
Price is the starting bid for a Ten-X auction to be held online from December 15-17. Pre-auction offers are being consi...
MLS# MDKE2003850
Listed by Taylor Properties