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

7439 Wilkins Lane, Chestertown $149,900

0.45 acres, no basement, handicap ramp leading to front door. Ideal for investors or first-time buyer with FHA203k rehab loan. DHCD property.

4 Beds
2 Baths
MDKE116126 MLS

321-343 Calvert Street, Chestertown image

321-343 Calvert Street, Chestertown $749,500

Lord Calvert Gardens 12-1 bedroom units in 4 buildings across from H. H. Garnett Elementary School. Close to Washington College and Hospital plus within walking distanc...

MDKE116114 MLS

103 Cedar Street, Chestertown $224,000

Beautiful and well maintained home in Chestertown's College Heights, close to the college and all that Chestertown has to offer. Even provides quick access to route 213 ...

3 Beds
2 Baths
MDKE116088 MLS

222 S Water Street, Chestertown $198,400

This unique unimproved lot is last available in Historic District with River views. It is surrounded by upscale modern properties some , of which, are waterfront condos. ...

MDKE116106 MLS

7956 Radcliffe Road, Chestertown $267,000

Three bedroom ranch home located in HEATHER HEIGHTS, south of Chestertown, near Chester River Yacht and Country Club and a short walk to the Chester River. Large lot that...

3 Beds
2 Baths
MDKE116102 MLS

4 Rolling Road, Chestertown $147,700

Own this home less than the cost to rent! 3 bedrooms, a remodeled full bathroom, living room, office, and wood floors complete the main level. The lower level features a ...

3 Beds
2 Baths
MDKE116100 MLS

312 Park Row, Chestertown $295,000

Prime location in downtown Chestertown! Formerly known as ~The Pippin Hotel,~ this property offers lots of possibilities including retail space on first floor and possibl...

MDKE116098 MLS

27759 Stryckning Road, Chestertown image

27759 Stryckning Road, Chestertown $219,900

Don't miss this 3BR, 2BA charming home with open country kitchen, large living room, den and spacious master bedroom with master bathroom and walk-in closet. Nicely situ...

3 Beds
2 Baths
MDKE116096 MLS

10718 Tilden Lane, Chestertown $999,000

Hidden away in a private park-like setting, this wonderful waterfront retreat is ideally situated to take advantage of panoramic views and access to Worton Creek and the ...

4 Beds
4 Baths
MDKE116070 MLS

207 S Cross Street, Chestertown $1,275,000 ▲

Rare Investment Opportunity: Mixed Use, Stabilized Asset. Provides both residential and commercial income. 1st Floor consists of multiple commercial tenancies: retail...

MDKE116084 MLS

200 Court Street, Chestertown $340,000

Great opportunity for someone wanting professional office space or would like to convert into a residence! RB professional zoning permits both! Was used as a law office...

MDKE116074 MLS

118 Little Harbor Way Unit #300, Chestertown image

118 Little Harbor Way Unit #300, Chestertown $899,900

Welcome to 118 Little Harbor Way, Unit 300 in Chester River Landing in Chestertown Maryland. This one of a kind Penthouse unit has panoramic views of the Chester River a...

3 Beds
4 Baths
MDKE116060 MLS

22428 Great Oak Landing Road, Chestertown image

22428 Great Oak Landing Road, Chestertown $297,000

Welcome Home to 22428 Great Oak Landing. Pull up to your very welcoming driveway complete with mature landscaping, room for boat, RV, and/or extra cars. Open concept floo...

3 Beds
2 Baths
MDKE116054 MLS

Lot 18 Grant Court, Chestertown $75,000

BUILD THAT DREAM HOUSE YOU HAVE ALWAYS WANTED. 1 ACRE LOT READY TO GO. BLAKEFIELD SUBDIVISION. CORNER LOT. ROADS JUST PUT IN. RIDE OUT AND SEE WHAT YOU THINK. BRING YOU...

MDQA142434 MLS

23064 Raleigh Road, Chestertown $125,000

Bungalow in the town of Fairlee. Cozy home with nice wood floors. Knotty Pine kitchen cabinets. Large lot has old shed/chicken coop and plenty of room for a large garden....

2 Beds
1 Baths
MDKE116048 MLS

118 Little Harbor Way Unit #101, Chestertown image

118 Little Harbor Way Unit #101, Chestertown $539,000

Shows great! Nice hardwood floors, beautiful millwork, built ins were custom made, granite counter tops, open floor plan, living room has a gas fireplace, private maste...

2 Beds
3 Baths
MDKE116030 MLS

537 High Street, Chestertown $325,000

Lovingly renovated home in the heart of historic Chestertown, just walking distance to all the shops and restaurants. Original details have been retained throughout the h...

3 Beds
3 Baths
MDKE116036 MLS

108 Harlan Loop, Chestertown $339,900

This home looks like it has never been lived in!!!. When you enter the two story entrance foyer (pease take off your shoes) you will get a sense of what a new home look...