Chestertown, MD 2 Bedroom Homes For Sale

61 homes

Use arrow keys to navigate
0.28 ACRES
$450,000
4 Beds
2.5 Baths
2,880 sqft
110 Trafford Dr,
Chestertown, MD 21620
RE/MAX Advantage Realty
Use arrow keys to navigate
OPEN SAT, 10-12PM
$510,000
5 Beds
3.5 Baths
3,932 sqft
218 Camelot Dr,
Chestertown, MD 21620
Coldwell Banker Realty
Use arrow keys to navigate
NEW CONSTRUCTION
$839,500
3 Beds
2.5 Baths
1,964 sqft
102 Little Harbor Way,
Chestertown, MD 21620
Gunther-McClary Real Estate
Use arrow keys to navigate
NEW CONSTRUCTION
$813,900
3 Beds
3.5 Baths
2,192 sqft
104 Landing Ln,
Chestertown, MD 21620
Gunther-McClary Real Estate
Use arrow keys to navigate
NEW CONSTRUCTION
$1,099,900
4 Beds
3.5 Baths
2,784 sqft
25 Landing Ln,
Chestertown, MD 21620
Gunther-McClary Real Estate
Use arrow keys to navigate
NEW CONSTRUCTION
$753,500
3 Beds
2.5 Baths
1,964 sqft
36 Landing Ln,
Chestertown, MD 21620
Gunther-McClary Real Estate
Use arrow keys to navigate
NEW CONSTRUCTION
$765,900
3 Beds
2.5 Baths
1,964 sqft
37 Landing Ln,
Chestertown, MD 21620
Gunther-McClary Real Estate
NEW CONSTRUCTION
$786,900
3 Beds
2.5 Baths
1,964 sqft
35 Landing Ln,
Chestertown, MD 21620
Gunther-McClary Real Estate
0.28 ACRES
$499,000
4 Beds
3 Baths
3,504 sqft
311 Devon Dr,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
$275,000
2 Beds
1.5 Baths
920 sqft
611 Cannon St,
Chestertown, MD 21620
Select Land & Homes, LLC
NEW CONSTRUCTION
$849,900
3 Beds
2.5 Baths
1,980 sqft
104 Little Harbor Way,
Chestertown, MD 21620
Gunther-McClary Real Estate
NEW CONSTRUCTION
$799,900
3 Beds
3.5 Baths
2,092 sqft
106 Landing Ln,
Chestertown, MD 21620
Gunther-McClary Real Estate
OPEN SAT, 10-12PM
$1,295,500
5 Beds
4.5 Baths
3,243 sqft
105 High St,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
$434,999
4 Beds
2 Baths
1,656 sqft
222 Mount Vernon Ave,
Chestertown, MD 21620
Long & Foster Real Estate, Inc.
1.37 ACRES
$499,900
4 Beds
2.5 Baths
2,524 sqft
8620 Park Dr,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
1.01 ACRES
$670,000
4 Beds
2.5 Baths
3,248 sqft
7844 Chester Ct,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
OPEN SUN, 11-1PM
0.84 ACRES
$2,200,000
5 Beds
4.5 Baths
4,305 sqft
7989 Quaker Neck Rd,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
$499,999
2 Beds
2.5 Baths
2,100 sqft
103 Landing Ln,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
1.65 ACRES
$385,000
4 Beds
3 Baths
2,630 sqft
23043 Bay Shore Spur,
Chestertown, MD 21620
Rock Hall Properties Real Estate
0.26 ACRES
$509,000
5 Beds
3.5 Baths
4,067 sqft
116 Harlan Loop,
Chestertown, MD 21620
Samson Properties
NEW CONSTRUCTION
$1,800,000
4 Beds
3.5 Baths
3,540 sqft
Little Harbor Way #1,
Chestertown, MD 21620
Gunther-McClary Real Estate

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
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
Use arrow keys to navigate
3D VIEW
1 ACRE
$400,000
2 Beds
2 Baths
1,344 sqft
612 Tanyard Rd,
Centreville, MD 21617
RE/MAX Executive
Use arrow keys to navigate
0.65 ACRES
$524,900
4 Beds
3.5 Baths
3,162 sqft
120 Archer Ln,
Millington, MD 21651
Cross Street Realtors LLC
Use arrow keys to navigate
NEW
COMING SOON 5/21
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 - 2 DAYS AGO
0.47 ACRES
$447,000
3 Beds
2 Baths
2,556 sqft
22300 Frazier Rd,
Rock Hall, MD 21661
Cross Street Realtors LLC
Use arrow keys to navigate
OPEN SAT, 12-2PM
2.5 ACRES
$685,000
3 Beds
2.5 Baths
1,745 sqft
4819 Eastern Neck Rd,
Rock Hall, MD 21661
Chaney Homes, LLC
Use arrow keys to navigate
NEW
COMING SOON 5/22
0.43 ACRES
$549,000
5 Beds
5 Baths
4,305 sqft
12712 Still Pond Rd #12714,
Still Pond, MD 21667
Coldwell Banker Chesapeake Real Estate Company
$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
NEW
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
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
OPEN SAT, 1-3PM
1.86 ACRES
$399,000
3 Beds
1 Bath
1,762 sqft
251 Rings End Rd,
Millington, MD 21651
Northrop Realty
OPEN SUN, 11:30-1:30PM
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
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
3D VIEW
1.27 ACRES
$750,000
6 Beds
5 Baths
5,277 sqft
118 Dabbling Ct,
Church Hill, MD 21623
Samson Properties
AUCTION
2.6 ACRES
Est. $339,700
2 Beds
2 Baths
1,500 sqft
1103 Barclay Rd,
Barclay, MD 21607
1.17 ACRES
$524,900
4 Beds
2.5 Baths
2,004 sqft
112 Lently Farm Ln,
Centreville, MD 21617
HomeSmart
1.18 ACRES
$498,000
3 Beds
2.5 Baths
1,574 sqft
405 Chester River Heights Rd,
Millington, MD 21651
Village Real Estate Company LLC
OPEN SUN, 11-1PM
$475,000
4 Beds
2.5 Baths
1,667 sqft
203 Brookfield Dr,
Centreville, MD 21617
Coldwell Banker Realty
OPEN SAT, 12-2PM
1.5 ACRES
$649,000
3 Beds
3 Baths
1,710 sqft
108 Claiborne Fields Dr,
Centreville, MD 21617
Coldwell Banker Realty
COMING SOON 5/22
0.51 ACRES
$350,000
3 Beds
2 Baths
1,820 sqft
640 Main St,
Church Hill, MD 21623
RE/MAX Executive
$595,000
4 Beds
3.5 Baths
3,508 sqft
131 Fair Brook Way,
Centreville, MD 21617
Redfin Corp
1.27 ACRES
$350,000
3 Beds
2 Baths
1,296 sqft
5666 Walnut St,
Rock Hall, MD 21661
Rock Hall Properties Real Estate
OPEN SAT, 11-2PM
1.37 ACRES
$699,000
4 Beds
2.5 Baths
2,640 sqft
988 White Marsh Rd,
Centreville, MD 21617
Compass
$299,000
3 Beds
1 Bath
1,008 sqft
11060 Plum Dr,
Worton, MD 21678
Patterson-Schwartz Real Estate
27.12 ACRES
$850,000
4 Beds
2 Baths
3,300 sqft
4020 Eastern Neck Rd,
Rock Hall, MD 21661
Rock Hall Properties Real Estate
0.34 ACRES
$288,500
3 Beds
1 Bath
960 sqft
11167 Oak Ln,
Worton, MD 21678
Chesapeake Real Estate Associates, LLC
0.28 ACRES
$699,900
4 Beds
3 Baths
2,592 sqft
119 Watson Rd,
Centreville, MD 21617
Long & Foster Real Estate, Inc.

1 More Home

We found 1 more home that matches your search in other listings.

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 2 Bedroom Homes For Sale

61 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