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24 Properties Available In Chestertown
- Default
- Price-High To Low
- Price-Low To High
- Newest Listings
- Beds (Most)
- Baths (Most)
- Year Built (Newest)
- Square Feet (Biggest)

$1,200,000
Single Family Home
22153 1ST POINT RD, Chestertown, MD 21620
Experience the waterfront lifestyle like never before in this stunning mid-century modern home, which seamlessly hangs c...
MLS# MDKE2004460
Listed by TTR Sotheby's International Realty


$749,900
Single Family Home
7988 ALDAN DR, Chestertown, MD 21620
This is a stunning property! It combines elegance and functionality with its spacious layout, beautiful finishes, and th...
MLS# MDKE2004966
Listed by Doug Ashley Realtors, LLC


$579,900
Single Family Home
5179 QUAKER NECK RD, Chestertown, MD 21620
A One-of-a-Kind Historic Treasure Reimagined for Modern Living<br>Step into history with this extraordinary Greek Reviva...
MLS# MDKE2005028
Listed by Hyatt & Company Real Estate, LLC


$364,900
Single Family Home
216 SILVER HEEL RD, Chestertown, MD 21620
Welcome to this move-in ready home, situated on a premium corner lot in The Village at Chestertown! This charming 1,742 ...
MLS# MDKE2005024
Listed by CENTURY 21 New Millennium


$385,000
Single Family Home
8605 CAMP RD, Chestertown, MD 21620
Your home sweet home retreat - a gorgeous 3 Bedroom 2 Full Bathroom Rancher with attached carport and unfinished basemen...
MLS# MDKE2004952
Listed by RE/MAX Executive


$285,000
Single Family Home
7483 SHORTALL ST, Chestertown, MD 21620
Discover this delightful, move-in-ready ranch-style home in a peaceful Chestertown setting. Featuring three bedrooms and...
MLS# MDKE2004948
Listed by RE/MAX Executive


$434,500
Single Family Home
130 SHEAFFER RD, Chestertown, MD 21620
Welcome to The Grove in Chestertown, a picturesque location in Queen Anne's county, located just a short drive from Ches...
MLS# MDQA2012600
Listed by Coldwell Banker Realty


$440,000
Single Family Home
128 EDMORE RD, Chestertown, MD 21620
Your Dream Eastern Shore Retreat Awaits!<br><br>Welcome to this meticulously maintained home, where charm and comfort bl...
MLS# MDQA2012546
Listed by Berkshire Hathaway HomeServices PenFed Realty


$319,000
Single Family Home
306 CEDAR ST, Chestertown, MD 21620
Lovely 4 bedroom, 2 bath Cape Cod located in College Heights. The house has been freshly painted inside and out and has...
MLS# MDKE2004954
Listed by Doug Ashley Realtors, LLC


$544,900
Single Family Home
314 DEVON DR, Chestertown, MD 21620
**Seller is motivated and ready to make a deal – bring your offer today!**<br>Welcome to 314 Devon Dr, Chestertown, MD 2...
MLS# MDKE2004946
Listed by The Parker Group


$289,500
Townhouse
116 OAK LEAF DR, Chestertown, MD 21620
Charming & Move-In Ready<br>Discover this beautifully maintained end-unit townhome just minutes from downtown Chestertow...
MLS# MDKE2004942
Listed by Doug Ashley Realtors, LLC


$324,900
Single Family Home
109 TAMARACK RD, Chestertown, MD 21620
Welcome to this beautiful 3-level Colonial in the sought-after Chester Harbor community on the Queen Anne's County side!...
MLS# MDQA2012102
Listed by RE/MAX Executive


$349,900
Single Family Home
110 FLYING CLOUD COURT, Chestertown, MD 21620
SINGLE FAMILY HOME (tax record is incorrect) in quaint little spot in Chestertown. Nearly new, beautiful home in the qu...
MLS# MDKE2004850
Listed by Berkshire Hathaway HomeServices Homesale Realty


$485,000
Single Family Home
123 BURCHARD SAWMILL RD, Chestertown, MD 21620
This is it! This is the one you and your horse have been dreaming about! Absolutely darling 4+ acre farmette! Charm char...
MLS# MDQA2012234
Listed by EXP Realty, LLC


$349,900
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


$269,000
Single Family Home
118 CHAR NOR MANOR BLVD, Chestertown, MD 21620
An adorable cottage with water views of the Chester River! Nicely maintained cottage featuring 3 bedrooms, 2 full baths ...
MLS# MDQA2011266
Listed by Chesapeake Real Estate Associates, LLC


$1,450,000
Condo
23393 CACAWAY FARM LN, Chestertown, MD 21620
**Exclusive Waterfront Craftsman Home with Sandy Beach – A Rare Opportunity**<br>Nestled on the serene East Fork of Lang...
MLS# MDKE2004002
Listed by Gunther-McClary Real Estate


$1,870,000
Commercial
870 HIGH ST, Chestertown, MD 21620
Radcliffe Mill presents an exceptional opportunity for a savvy investor looking for value and a one-of-a-kind investment...
MLS# MDKE2004140
Listed by Taylor Properties


$860,000
Commercial
860 HIGH ST, Chestertown, MD 21620
The Annex/Seed House at Radcliffe Mill is a stunning, one of a kind space. Fully restored in 2007, with additional work...
MLS# MDKE2004138
Listed by Taylor Properties


$2,700,000
Commercial
860 & 870 HIGH ST, Chestertown, MD 21620
Radcliffe Mill presents an exceptional opportunity for a savvy investor looking for value and a one-of-a-kind investment...
MLS# MDKE2003850
Listed by Taylor Properties


$425
Commercial
870 HIGH ST #INDIVIDUAL OFFICES, Chestertown, MD 21620
Individual office for rents, ranging from private office suites, private offices to cubicles. All utilities, including...
MLS# MDKE2004432
Listed by Taylor Properties


$18
Commercial
870 HIGH ST #2-3, Chestertown, MD 21620
Three floors of premium office space are available for lease at Radcliffe Mill. This listing encompasses the top three f...
MLS# MDKE2003776
Listed by Taylor Properties


$18
Commercial
870 HIGH ST #2, Chestertown, MD 21620
Strategically positioned at the head of the Rail Trail leading to downtown Chestertown and Washington College, and on th...
MLS# MDKE2003772
Listed by Taylor Properties


$18
Commercial
870 HIGH ST #3, Chestertown, MD 21620
Strategically positioned at the head of the Rail Trail leading to downtown Chestertown and Washington College, and on th...
MLS# MDKE2003766
Listed by Taylor Properties
