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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, MDDuring 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

23730 Handy Point   Road, Chestertown image
23730 Handy Point Road, Chestertown $219,000

Formerly used as a house of worship, this property is zoned Village which could allow for many different uses including a residence. The building is almost 2000 sq. ft. w...

  • 2 Baths
  • MDKE117682 MLS
23730 Handy Point   Road, Chestertown image
23730 Handy Point Road, Chestertown $219,000

Formerly used as a house of worship, this property is zoned Village which could allow for many different uses. The building is almost 2000 square feet with a large open r...

  • MDKE117680 MLS
211 Devon   Drive, Chestertown image
211 Devon Drive, Chestertown $245,000

Coventry Farms Rancher! Enjoy one level living in the 3 bedroom 2 bath rancher with attached garage, and rear screened in porch. This home is close to the waterfront coll...

  • 3 Beds
  • 2 Baths
  • MDKE117676 MLS
204 Boundary   Avenue, Chestertown image
204 Boundary Avenue, Chestertown $259,900

Great location on a 1 acre corner lot within minutes of downtown Chestertown on the Queen Anne County side of the Chester River. The home needs some TLC but has great pot...

  • 3 Beds
  • 2 Baths
  • MDQA146776 MLS
306 Roosevelt   Drive, Chestertown image
306 Roosevelt Drive, Chestertown $139,900

Nice rancher with three bedrooms, 1.5 bathrooms, nice living room , kitchen, family room. and CAC/Heat. Affordably priced and just needs some TLC from you to turn thi...

  • 3 Beds
  • 2 Baths
  • MDKE117666 MLS
102 Conley   Drive, Chestertown image
102 Conley Drive, Chestertown $184,900

Completely renovated 1,280 sq ft 3BR Townhome in the heart of historic Chestertown on residential street with little traffic. Well maintained home has been completely upd...

  • 3 Beds
  • 2 Baths
  • MDKE117652 MLS
21320 Persimmon   Drive Unit #LOT 9, Chestertown image
21320 Persimmon Drive Unit #LOT 9, Chestertown $121,900

Updated two bedroom, one bath townhome that shows great! There is a community sports court on the common areas, a small playground area, high speed internet is availabl...

  • 2 Beds
  • 1 Baths
  • MDKE117650 MLS
Broad Neck   Road, Chestertown image
Broad Neck Road, Chestertown $200,000

This beautiful wooded waterfront lot located at the head waters of Lovely Cove is perc approved and ready for your new home. Perc approved for sand mound septic system, ...

  • MDKE117636 MLS
225 Richard   Drive, Chestertown image
225 Richard Drive, Chestertown $445,000

Location, location, location! Wonderfully maintained one story brick rancher. Flexible floor plan allows for in-home office, primary bedroom with views of the water, fire...

  • 4 Beds
  • 3 Baths
  • MDKE117622 MLS
Cloquet   Road, Chestertown image
Cloquet Road, Chestertown $50,000

Largest privately held parcel in Chesapeake Landing. 8 Lots each more than 10,000 sq ft. for a total 1.51 acres. Tax map 27, lots 254-257 & 297-300 (2 contiguous lots). T...

  • MDKE117632 MLS
206 S Cross   Street Unit #201, Chestertown image
206 S Cross Street Unit #201, Chestertown $835,000

This prime Downtown Chestertown space is move in ready and available for your business! Over 4800 sq.ft., with exposed brickwork, reclaimed hardwood flooring, high ceilin...

  • MDKE117590 MLS
307 S Queen   Street, Chestertown image
307 S Queen Street, Chestertown $345,000

The Chester River is just across the open space of Wilmer Park, from this townhome! The living room, with vaulted ceiling, fireplace and sky lights, is bright and roomy....

  • 3 Beds
  • 3 Baths
  • MDKE117594 MLS
206 S Cross   Street Unit #101, Chestertown image
206 S Cross Street Unit #101, Chestertown $285,000

This prime Downtown Chestertown space is available for your business! Over 1100 sq.ft., with generous windows for street front exposure, in a newly renovated building, in...

  • MDKE117588 MLS
810 Double Creek Point Road, Chestertown image
810 Double Creek Point Road, Chestertown $250,000

*NEW CONSTRUCTION* To be built. Lot cleared and ready! Quiet and peaceful Eastern Shore living. 4 Bedroom 2 Full baths. Wonderful price in this competitive market to get ...

  • 4 Beds
  • 2 Baths
  • MDQA146558 MLS
111 Cee Jay Road, Chestertown image
111 Cee Jay Road, Chestertown $245,000

Quiet and peaceful living. 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...

  • 4 Beds
  • 2 Baths
  • MDQA146372 MLS
10145 3rd Point   Road, Chestertown image
10145 3rd Point Road, Chestertown $439,000 ▼

Don't miss your chance to own in Great Oak Landing. Make this summer a new beginning by the Bay. Play a round on the 9-hole executive golf course or enjoy the summer heat...

  • 3 Beds
  • 3 Baths
  • MDKE117494 MLS
207 S Cross   Street, Chestertown image
207 S Cross Street, Chestertown $1,250,000

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

  • MDKE117496 MLS
property image
1933 Mcginnes Road, Chestertown $75,000

Affordable, wooded building lot in Queen Anne's county! Not many lots left at this price point. Perc approved for standard 4 bedroom septic. Great location for commute...

  • MDQA146172 MLS
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