Chestertown, MD Real Estate & Homes For Sale

104 homes

Use arrow keys to navigate
1.65 ACRES
$385,000
4 Beds
3 Baths
2,630 sqft
23043 Bay Shore Spur,
Chestertown, MD 21620
Rock Hall Properties Real Estate
Use arrow keys to navigate
0.26 ACRES
$509,000
5 Beds
3.5 Baths
4,067 sqft
116 Harlan Loop,
Chestertown, MD 21620
Samson Properties
Use arrow keys to navigate
2.15 ACRES
$164,000
7224 Rock Hall Rd,
Rock Hall, MD 21661
Rock Hall Properties Real Estate
Use arrow keys to navigate
0.55 ACRES
$10,000
Buck Neck Landing Rd,
Chestertown, MD 21620
Rosendale Realty
Use arrow keys to navigate
0.9 ACRES
$25,000
Johnsontown Rd,
Chestertown, MD 21620
Berkshire Hathaway HomeServices PenFed Realty
Use arrow keys to navigate
0.34 ACRES
$9,000
Kinglet Rd,
Chestertown, MD 21620
Chesapeake Real Estate Associates, LLC
Use arrow keys to navigate
0.34 ACRES
$9,000
Buck Neck Rd,
Chestertown, MD 21620
Chesapeake Real Estate Associates, LLC
87.34 ACRES
$3,000,000
Cromwell Clark Rd,
Chestertown, MD 21620
The Land Group
2 ACRES
$150,000
Caulks Field Rd,
Chestertown, MD 21620
RE/MAX Allegiance
2 ACRES
$150,000
Georgetown Rd SE,
Chestertown, MD 21620
RE/MAX Allegiance
NEW CONSTRUCTION
$1,800,000
4 Beds
3.5 Baths
3,540 sqft
Little Harbor Way #1,
Chestertown, MD 21620
Gunther-McClary Real Estate
AUCTION
0.34 ACRES
$5,000
Towhee Rd,
Chestertown, MD 21620
Ashland Auction Group LLC
AUCTION
0.34 ACRES
$5,000
Beltram Rd,
Chestertown, MD 21620
Ashland Auction Group LLC
AUCTION
0.37 ACRES
$5,000
Fish Hatchery Rd,
Chestertown, MD 21620
Ashland Auction Group LLC
AUCTION
0.34 ACRES
$5,000
Bunting Rd,
Chestertown, MD 21620
Ashland Auction Group LLC
0.52 ACRES
$22,900
E Step,
Chestertown, MD 21620
0.34 ACRES
$9,500
Buck Neck Landing Rd,
Chestertown, MD 21620
Long & Foster Real Estate, Inc.
AUCTION
0.34 ACRES
$8,000
PARCEL Buck Neck Rd,
Chestertown, MD 21620
Ashland Auction Group LLC
$40,000
Montgomery Ave,
Chestertown, MD 21620
The Hogans Agency
0.5 ACRES
$24,000
23710 L Rd,
Chestertown, MD 21620
Long & Foster Real Estate, Inc.
0.34 ACRES
$37,000
Fish Hatchery Rd,
Chestertown, MD 21620
Long & Foster Real Estate, Inc.
0.56 ACRES
$38,000
Spinnaker Rd,
Chestertown, MD 21620
Long & Foster Real Estate, Inc.
0.34 ACRES
$38,000
Redfield Rd,
Chestertown, MD 21620
Long & Foster Real Estate, Inc.
0.34 ACRES
$15,000
Sheldrake Dr,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company

Real Estate & Homes For Sale Near Chestertown, MD

We found 30 more homes matching your filters just outside Chestertown

Use arrow keys to navigate
NEW - 12 HRS AGO
9.06 ACRES
$180,000
1420 Barclay Rd,
Barclay, MD 21607
Benson & Mangold, LLC
Use arrow keys to navigate
NEW
COMING SOON 5/28
$384,900
3 Beds
2.5 Baths
1,712 sqft
21124 Striper Run Rock,
Rock Hall, MD 21661
RE/MAX Executive
Use arrow keys to navigate
NEW
COMING SOON 6/30
0.25 ACRES
$325,000
3 Beds
2 Baths
1,376 sqft
11054 Austin Ln,
Worton, MD 21678
RE/MAX Chesapeake
Use arrow keys to navigate
OPEN SAT, 10-12PM
1 ACRE
$725,000
4 Beds
3 Baths
3,010 sqft
306 Old Line Dr,
Centreville, MD 21617
Taylor Properties
Use arrow keys to navigate
NEW - 1 DAY AGO
0.27 ACRES
$650,000
4 Beds
2 Baths
2,271 sqft
20694 Mercer Ave,
Rock Hall, MD 21661
Gunther-McClary Real Estate
Use arrow keys to navigate
NEW - 1 DAY AGO
$650,000
3 Beds
2.5 Baths
2,400 sqft
20563 Rock Hall Ave #16,
Rock Hall, MD 21661
Gunther-McClary Real Estate
Use arrow keys to navigate
NEW
COMING SOON 5/27
$330,000
3 Beds
2 Baths
1,484 sqft
11976 Flour Mill St,
Kennedyville, MD 21645
Coldwell Banker Chesapeake Real Estate Company
AUCTION
5.88 ACRES
Est. $510,200
Studio
2 Baths
1,552 sqft
415 Flat Iron Square Rd,
Church Hill, MD 21623
COMING SOON 6/1
1.48 ACRES
$950,000
5 Beds
4.5 Baths
5,764 sqft
218 Upland Ln,
Centreville, MD 21617
Wilson Realty & Staging LLC
COMING SOON 5/22
$425,000
3 Beds
2 Baths
1,400 sqft
21007 Bayside Ave,
Rock Hall, MD 21661
Rock Hall Properties Real Estate
0.43 ACRES
$86,000
River Bend Ln,
Millington, MD 21651
Coldwell Banker Chesapeake Real Estate Company
COMING SOON 5/23
0.76 ACRES
$560,000
3 Beds
2.5 Baths
2,208 sqft
137 White Marsh Rd,
Centreville, MD 21617
RE/MAX Executive
0.65 ACRES
$524,900
3 Beds
3.5 Baths
3,162 sqft
120 Archer Ln,
Millington, MD 21651
Cross Street Realtors LLC
0.47 ACRES
$447,000
3 Beds
2 Baths
2,556 sqft
22300 Frazier Rd,
Rock Hall, MD 21661
Cross Street Realtors LLC
COMING SOON 5/22
0.43 ACRES
$549,000
6 Beds
5 Baths
4,305 sqft
12712 Still Pond Rd #12714,
Still Pond, MD 21667
Coldwell Banker Chesapeake Real Estate Company
10.4 ACRES
$850,000
21190 Green Ln,
Rock Hall, MD 21661
Rock Hall Properties Real Estate
$310,000
2 Beds
1 Bath
1,700 sqft
313 Oak St,
Centreville, MD 21617
Cummings & Co. Realtors
1.56 ACRES
$649,000
4 Beds
2.5 Baths
3,216 sqft
337 Roe Ingleside Rd,
Centreville, MD 21617
Taylor Properties
2 ACRES
$75,000
11200 Boyer Ln,
Worton, MD 21678
Chesapeake Real Estate Associates, LLC
COMING SOON 5/22
$215,000
2 Beds
1 Bath
1,152 sqft
223 New St,
Church Hill, MD 21623
Long & Foster Real Estate, Inc.
1.83 ACRES
$730,000
6 Beds
3.5 Baths
3,554 sqft
615 Ell Downes Rd,
Henderson, MD 21640
Benson & Mangold, LLC
360.51 ACRES
$4,950,000
Worton Hopewell Rd,
Worton, MD 21678
Cross Street Realtors LLC
OPEN SAT, 11-1PM
COMING SOON 5/22
0.27 ACRES
$359,900
3 Beds
2 Baths
1,381 sqft
5862 N Main St,
Rock Hall, MD 21661
LPT Realty, LLC
0.31 ACRES
$60,000
21451 E Sharp St,
Rock Hall, MD 21661
Bayside Realty
1.86 ACRES
$399,000
3 Beds
1 Bath
1,762 sqft
251 Rings End Rd,
Millington, MD 21651
Northrop Realty
3D VIEW
$300,000
2 Beds
1.5 Baths
879 sqft
201 Belvedere Ave,
Centreville, MD 21617
Long & Foster Real Estate, Inc.
FORECLOSURE
BANK OWNED
1.41 ACRES
$229,000
3 Beds
1 Bath
1,440 sqft
1826 Sudlersville Rd,
Sudlersville, MD 21668
212 Degrees Realty, LLC
FOR SALE BY OWNER
0.34 ACRES
$250,000
Studio
0.5 Baths
224 sqft
5728 Beach Rd,
Rock Hall, MD 21661
2.17 ACRES
$759,900
4 Beds
3.5 Baths
3,282 sqft
127 Pleasant Springs Dr,
Centreville, MD 21617
Chesapeake Real Estate Associates, LLC
1.64 ACRES
$128,000
Crosby Rd,
Rock Hall, MD 21661
Rock Hall Properties Real Estate

Listing information is 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, and is provided by BRIGHT through a licensing agreement. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information 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 the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 Bright MLS, Inc. Click here for more information

Chestertown, MD Real Estate & Homes For Sale

104 homes

We found 30 more homes matching your filters just outside Chestertown

Nearby Real Estate

Nearby Zip Codes

Popular Cities in Maryland

Chestertown Neighborhoods

Chestertown Property Types

Real Estate Guides

Find Rental Properties