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

127 E Step Road, Chestertown $245,000

Quiet and Peaceful. Your chance to get a new home for a great price! Being built, is a 4 bedroom 2 bath open floorplan rancher. Everything you need. Why settle for any ...

4 Beds
2 Baths
MDQA146072 MLS

10788 Mallard Point Road, Chestertown image

10788 Mallard Point Road, Chestertown $470,000

Wonderful home nestled in a park like setting located on pristine Mill Creek leading to Worton Creek and just a very short boat ride to the Chesapeake Bay. This delightfu...

3 Beds
3 Baths
MDKE117364 MLS

355 High Street, Chestertown $244,000

Mixed use building offering many opportunities located in Downtown Chestertown's Historic District. Business space on the first floor and large residential space on the s...

MDKE117420 MLS

21341 Persimmon Drive Unit #17, Chestertown image

21341 Persimmon Drive Unit #17, Chestertown $119,900

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

2 Beds
1 Baths
MDKE117406 MLS

307 Central Drive, Chestertown $212,000 ▼

This home has great curb appeal, plenty of parking space, and a level backyard. Although this home needs some updating, it is priced with this in mind. The attached one...

3 Beds
2 Baths
MDQA145942 MLS

103 S College Avenue, Chestertown $295,000

Updated home.. fenced back yard with a storage shed, zoned heat pumps. There is a patio and a third floor deck overlooking the semi private back yard. Brand new carpet t...

2 Beds
2 Baths
MDKE117358 MLS

102 Wilton Road, Chestertown $212,000

Cute as a button, three bedroom 2 bath cottage with an open living area. Back yard is adorable, extremely private, with a deck, and plenty of room for kids of all ages, ...

3 Beds
2 Baths
MDQA145776 MLS

Morgnec Road, Chestertown $1,500,000

Over 13 acres at the corner of routes 213 & 291 in Chestertown. High traffic count intersection. Per MDOT, current Annual Average Daily Traffic is 14,710. Zoned RB Profes...

MDKE117304 MLS

104 Church Alley, Chestertown $242,000

Historic renovated office building, c.1880 is set in the heart of the Chestertown Historic District. Convenient Church Alley location is one block from the Courthouse and...

MDKE117260 MLS

108 S Kent Street, Chestertown $199,900

This charming Downtown Chestertown home offers a semi open floor plan and cozy feel with hardwood floors throughout! The first floor features a dining and living area, po...

1 Beds
2 Baths
MDKE117300 MLS

21317 Persimmon Drive Unit #23, Chestertown image

21317 Persimmon Drive Unit #23, Chestertown $119,900

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

2 Beds
1 Baths
MDKE117236 MLS

324 Longfellow Drive, Chestertown $249,500

Quiet, one level living on a spacious .34 acre property in Chester Harbor with community water access, beach & picnic area with dock. This well maintained 3 bedroom, 2 ...

3 Beds
2 Baths
MDQA145652 MLS

719 Round Top Road, Chestertown $273,000 ▼

OPEN HOUSE - SUN. Nov. 22nd - 2pm to 4pm - *HURRY! Completely updated and gorgeous!! This 4BR, 2 bath one-level living is in move-in, excellent condition. Granite counter...

4 Beds
2 Baths
MDQA145556 MLS

Church Hill Road, Chestertown $129,000

5.34 acre country lot. Perc approved . convenient to Chestertown , Church Hill, Centreville, and Rt 301. Great place to build your dream home!

MDQA145622 MLS

5750 Honest Point Lane, Chestertown image

5750 Honest Point Lane, Chestertown $2,750,000

Presenting "Honest Point Farm" - Embrace the finest of Eastern Shore Living, Serenity and Nature at Honest Point Farm. Three Waterfront homes in Chestertown's Estate a...

5 Beds
5 Baths
MDKE117208 MLS

609 High Street, Chestertown $690,000

Commercial building available at 609 High St in Chestertown. 3200 Square feet offers off street parking for 20+ vechicles. 400 amp panel features 3 phase electric. Block...

MDKE117168 MLS

High Street, Chestertown $75,000

2.64 acres behind High Street with deeded right of way (see documents) from High Street to property . Zoned C1/R2.

MDKE117140 MLS

106 N Water Street, Chestertown $318,000 ▼

A real restoration opportunity on Water St. This Victorian is a project for someone who has a love of old houses.It needs attention. This house has a Mansard roof is ...