Chestertown

Explore Homes for Sale in Chestertown, MD

Chestertown, MD offers a unique blend of historic charm, waterfront beauty, and small-town living on Maryland’s Eastern Shore. From Colonial-era homes in the heart of downtown to serene riverfront retreats, this area has something for every type of buyer. Explore current real estate listings and discover the lifestyle that makes Chestertown one of the Eastern Shore’s most sought-after destinations.

7514 Muirfield Drive Chestertown, MD 21620

7514 Muirfield Drive Chestertown, MD 21620

Hoffecker Rd. Chestertown, MD 21620

Hoffecker Rd. Chestertown, MD 21620

21090 W Sharp St #133 Rock Hall, MD 21661

21090 W Sharp St #133 Rock Hall, MD 21661

11944 Augustine Herman Hwy. Kennedyville MD 21645

11944 Augustine Herman Hwy. Kennedyville MD 21645

300 Hickory Lane Chestertown, MD 21620

300 Hickory Lane Chestertown, MD 21620

Clam Cove, Rock Hall MD 21661

Clam Cove, Rock Hall MD 21661

11636 Lynch Rd. Lynch, MD 21678

11636 Lynch Rd. Lynch, MD 21678

26875 Mallard Rd. Chestertown, MD 21620

26875 Mallard Rd. Chestertown, MD 21620

20565 Rock Hall Ave #5 Rock Hall, MD 21661

20565 Rock Hall Ave #5 Rock Hall, MD 21661

Little Harbor Way #1 Chestertown, MD 21620

Little Harbor Way #1 Chestertown, MD 21620

Rock Harbor Drive Rock Hall, MD 21661

Rock Harbor Drive Rock Hall, MD 21661

Gregg Neck Road Galena MD 21635

Gregg Neck Road Galena MD 21635

Landing Lane Chestertown MD 21620

Landing Lane Chestertown MD 21620

103 Landing Lane Chestertown MD 21620

103 Landing Lane Chestertown MD 21620

226 S Water St. Chestertown, MD 21620

226 S Water St. Chestertown, MD 21620

Edwards Lane Rock Hall, MD 21661

Edwards Lane Rock Hall, MD 21661

21119 Striper Run Rock Hall, MD 21661

21119 Striper Run Rock Hall, MD 21661

Rock Hall Ave. Rock Hall, MD 21661

Rock Hall Ave. Rock Hall, MD 21661

21424 Catholic Ave Rock Hall MD 21661

21424 Catholic Ave Rock Hall MD 21661

5686 S Main St. Rock Hall, MD 21661

5686 S Main St. Rock Hall, MD 21661

Lawton Ave. Rock Hall, MD 21661

Lawton Ave. Rock Hall, MD 21661

Henry Avenue Rock Hall, MD 21661

Henry Avenue Rock Hall, MD 21661

212 Landing Lane Chestertown MD 21620

212 Landing Lane Chestertown MD 21620

117 Water St N #2A Chestertown, MD 21620

117 Water St N #2A Chestertown, MD 21620

117 N Water St #1A Chestertown MD 21620

117 N Water St #1A Chestertown MD 21620

230 S Water St. Chestertown, MD 21620

230 S Water St. Chestertown, MD 21620

228 S Water St. Chestertown, MD 21620

228 S Water St. Chestertown, MD 21620

Walnut St. Church Hill, MD 21623

Walnut St. Church Hill, MD 21623

Old Fairlee Rd. Chestertown, MD 21620

Old Fairlee Rd. Chestertown, MD 21620

Rock Hall Ave. Rock Hall, MD 21661

Rock Hall Ave. Rock Hall, MD 21661

Mckinleyville Rd. Rock Hall, MD 21661

Mckinleyville Rd. Rock Hall, MD 21661

Coleman Dr. Chestertown, MD 21620

Coleman Dr. Chestertown, MD 21620

Wilkins Ave. Rock Hall, MD 21661

Wilkins Ave. Rock Hall, MD 21661

S. Hawthorne Ave. Rock Hall, MD 21661

S. Hawthorne Ave. Rock Hall, MD 21661

Tamarack Rd. Chestertown, MD 21620

Tamarack Rd. Chestertown, MD 21620

Hillmont Dr. Rock Hall, MD 21661

Hillmont Dr. Rock Hall, MD 21661

E. Kentfield Rd. Worton, MD 21678

E. Kentfield Rd. Worton, MD 21678

Liberty St. Rock Hall, MD 21661

Liberty St. Rock Hall, MD 21661

N Bayview Ave. Chestertown, MD 21620

N Bayview Ave. Chestertown, MD 21620

Beach Rd. Rock Hall, MD 21661

Beach Rd. Rock Hall, MD 21661

Grays Inn Creek Rd. Rock Hall, MD 21661

Grays Inn Creek Rd. Rock Hall, MD 21661

Striper Run Rock Hall, MD 21661

Striper Run Rock Hall, MD 21661