Chestertown Real Estate - One Easy MLS Search

If you enjoy history and beautiful water views in a country setting this is your kind of town. Chestertown is quiet College town, home of Washington College a Liberal Arts school founded in 1782. Chestertown offers many fun things to do during throughout year with your family. Historic Chestertown, MD During the warmer months, there is a farmers market down town every saturday from 8-12pm. The farmers market offers lots of fresh produce, plants, flowers, and hand crafted works of local artisans. Every year on Memorial day weekend they have their annual Tea Party parade and festival that always brings out a great crowd.

Newest Property Listings In Chestertown

105 S Mill Street, Chestertown $625,000

Renovated by the editor of Historic Houses of Kent County, the Davis Duplex is the perfect blend of historic charm and modern amenities. The property features a first flo...

3 Beds
3 Baths
MDKE117106 MLS

25030 Chestertown Road, Chestertown image

25030 Chestertown Road, Chestertown $210,000

Adorable, affordable 4 bedroom, 2 bath saltbox style home just outside the town of Chestertown. Over half an acre with room to roam, yet close to town amenities. 2012 re...

4 Beds
2 Baths
MDKE117090 MLS

7979 Sandy Bottom Road, Chestertown image

7979 Sandy Bottom Road, Chestertown $299,900

The old "Hilltop Hotel"! This was once a hotel that was visited by many who vacationed at Tolchester Beach Amusement Park. Some renovations and updates have been compl...

3 Beds
3 Baths
MDKE117070 MLS

Mt Pleasant Plantation Drive, Chestertown image

Mt Pleasant Plantation Drive, Chestertown $750,000

Why drive 2 hours for hunting, when you can walk out your back door. This 77 acrea parcel was designed for waterfowl with two ponds, one drainable, and plenty of surroun...

MDKE117066 MLS

21244 Iowa Avenue, Chestertown $220,000

Rancher with 2 car detached garage 24' x 30' on a private dead end street with lots of trees. 4 bedrooms 2 full baths

4 Beds
1 Baths
MDKE117078 MLS

10050 Forrest Lane, Chestertown $575,000

Best of all worlds. with 5+ acres of private woodland. This waterfront home has very easy water access and natural surroundings. Located on Fairlee Creek, just minutes ...

4 Beds
2 Baths
MDKE117068 MLS

301 Hickory Lane, Chestertown $650,000

This 37-acre waterfront farm offers endless possibilities and an exceptional opportunity to generate multiple streams of income! The property backs to the Chester River a...

4 Beds
3 Baths
MDQA145178 MLS

301 Hickory Lane, Chestertown $650,000

This 37-acre waterfront farm offers endless possibilities and an exceptional opportunity to generate multiple streams of income! The property backs to the Chester River a...

4 Beds
3 Baths
MDQA145180 MLS

7784 Country Club Lane, Chestertown image

7784 Country Club Lane, Chestertown $525,000

Quality and class go hand in hand with this Country Club Estates beauty, which boasts vaulted & tray 9'+ ceilings, Brazilian Cherry hardwood floors throughout, GOURMET KI...

3 Beds
2 Baths
MDKE117060 MLS

127 N Queen Street, Chestertown $295,000

Want to live on one of Chestertown's most desirable streets? Look no further! This lovely home boasts hardwood flooring, tall ceilings, elegant molding and trim, and orna...

4 Beds
2 Baths
MDKE117044 MLS

106 Edmore Road, Chestertown $217,500 ▲

Charming 3 bedroom ranch home close to Chestertown. This home features a remodeled kitchen that opens into a large family room over looking the backyard, wood burning fir...

3 Beds
1 Baths
MDQA145108 MLS

23264 Clarissa Road, Chestertown $249,900

Under Construction, December/January Delivery.. .....Looking for a brand NEW home & the simple pleasures of one level living?? Look No Further!! Beautiful, Affordable R...

3 Beds
2 Baths
MDKE117034 MLS

21313 Persimmon Drive, Chestertown image

21313 Persimmon Drive, Chestertown $129,900

Take a look at this beautiful model home located in Tolchester Village! One of 23 available duplexes and townhouses that have been completely remodeled!! Featuring a ter...

3 Beds
1 Baths
MDKE117004 MLS

21354 Lynn Lane, Chestertown $129,900

Take a look at this beautiful model home located in Tolchester Village! One of 23 available duplexes and townhouses that have been completely remodeled!! Featuring a ter...

3 Beds
1 Baths
MDKE117002 MLS

125 Scheeler Road, Chestertown $1,100,000

One of the few C-1 Corner Commercial Properties left of it's size in Chestertown 2.7+acres Verify with the town regarding Uses, public water and sewer hookup . Level lot...

MDKE117010 MLS

504 Washington Avenue, Chestertown image

504 Washington Avenue, Chestertown $800,000

Prime High Traffic Commercial property on Rt 213 in the heart of Chestertown. Next to Washington College. Formerly Rita's Ice but has countless possibilities. Zoned C-3 C...

MDKE117008 MLS

7801 Airy Hill Road, Chestertown $599,900 ▼

Stunning 4 Bed 4 Full bath sitting on over 2 peaceful and secluded acres, circle driveway with plenty of garage space. Surrounded by farmland and yet only 2 miles from Ch...

4 Beds
4 Baths
MDKE116996 MLS

202 Mount Vernon Avenue, Chestertown image

202 Mount Vernon Avenue, Chestertown $395,000

TENANT OCCUPIED - 12 hour plus Notice Required. COVID PROTOCOL REQUIRED. Charm, character and natural light abound in this home which was expanded, renovated and update...