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

Park Drive, Chestertown $85,000

Your piece of the block and a fine piece it is. Two parcels totaling approximately 1.81 Acres on a quiet street among well-kept homes and manicured lawns. The second par...

MDKE116398 MLS

6798 Broad Neck Road, Chestertown $6,500,000

"Walnut Point Farm" ~ Exquisite 300+ Acre Waterfront Farm with over a mile of Shoreline is the perfect Eastern Shore Retreat! The Estate offers a 7,500+/- Main House with...

5 Beds
6 Baths
MDKE116276 MLS

9816 Fairlee Road, Chestertown $275,000

Over 6 acres of land to explore. And the home has numerous upgrades... a gorgeous master bath with huge tiled shower, upgraded hall bath and kitchen, new roof, 5 years yo...

2 Beds
2 Baths
MDKE116352 MLS

9201 Fairlee Road, Chestertown $118,000

The house needs work, but it sits on over 2 acres just outside of Fairlee. Classic knotty pine paneling, hardwood floors, two bedrooms and a bathroom with a walk in tub. ...

2 Beds
1 Baths
MDKE116362 MLS

125 Haacke Drive, Chestertown $699,000

Property Highlights- 9 acre lot Soil types are viable for constructionMunicipal water & sewer services available Site is Zoned for Institutional Use which permits public ...

MDKE116364 MLS

611 Cannon Street, Chestertown $137,500

Just a few blocks away from the Chester River and all that Chestertown has to offer, this cute bungalow has been well maintained and was a very successful rental for 19 y...

2 Beds
2 Baths
MDKE116372 MLS

130 Prospect Street, Chestertown $125,000

Beautifully renovated home, move-in ready, perfect for a first time homebuyer! Close your eyes and allow me to virtually guide you through your soon to be home: Enter the...

3 Beds
2 Baths
MDKE116382 MLS

914 N Meadowview Drive, Chestertown image

914 N Meadowview Drive, Chestertown $320,000

Coming Soon! This immaculately maintained home offers main level living... gleaming hardwood floors, a generous master suite, a screened in porch and huge fenced backyard...

4 Beds
3 Baths
MDKE116336 MLS

110 Trafford Drive, Chestertown $315,000

None

4 Beds
3 Baths
MDKE116284 MLS

411 E Campus Avenue, Chestertown $349,000

One of the few properties in Chestertown on a full acre of land! The solid brick home has undergone an extensive renovation to include a gourmet kitchen, new HVAC and win...

4 Beds
3 Baths
MDKE116378 MLS

23706 L Road, Chestertown $130,000

This Property is tucked away from it all. Great Deal, 2 for the Price of One- Home is 1152 sq. ft of Main Level Living on 3 acres, plus front Extra Lot of 1/2 acre raw la...

3 Beds
2 Baths
MDKE116260 MLS

111 Trafford Drive, Chestertown $297,000

Coventry charmer with a fenced back yard, deck with new awning makes this an "outdoor room". Family room is open to the kitchen/breakfast area. Partially finished basem...

3 Beds
3 Baths
MDKE116368 MLS

8630 Elm Road, Chestertown $279,900

Hot New Listing in Tolchester!!! Check out this 4 Bedroom 2.5 bath home with approx 1936 sq ft in Tolchester Estates. Recently Updated . This is a quality stick built hom...

4 Beds
3 Baths
MDKE116230 MLS

25026 Chestertown Road, Chestertown image

25026 Chestertown Road, Chestertown $210,000

A peaceful setting for this classic brick cape cod just outside of Chestertown. Enjoy a picnic on the porch or a dip in the pool - there's plenty of room to play on this...

4 Beds
2 Baths
MDKE116358 MLS

118 Little Harbor Way Unit #202, Chestertown image

118 Little Harbor Way Unit #202, Chestertown $600,000

This 1,600 sf ritzy waterfront suite simply exudes class. The unobstructed panoramic views of the Chester to the Bridge serve as living art bringing the River into the h...

3 Beds
2 Baths
MDKE116302 MLS

218 Central Drive, Chestertown $129,500 ▼

*INVESTOR ALERT!* Opportunity awaits in Chester Harbor - This is a cute 2 bedroom, 1 bath rancher with a full basement and is priced to sell. This could be turned into ...

2 Beds
1 Baths
MDQA143260 MLS

109 High Street, Chestertown $346,000

The Malloy House has stood proudly in the heart of Historic Chestertown since. ca. 1753 as a handsome example of the Colonial period. It has been beautifully maintained a...

3 Beds
3 Baths
MDKE116332 MLS

6910 Pentridge Lane, Chestertown $950,000

This is a "must see" to appreciate all this waterfront property has to offer. Located on the East Fork of Langford the setting is beautiful with grounds designed by a lan...