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Newest Property Listings In Chestertown

8312 Broad Neck Rd, Chestertown image
8312 Broad Neck Rd, Chestertown $380,000

Bring your vision and transform this unique property into the home of your dreams. Situated on 3.79 picturesque acres, the property features a beautiful one-acre stocked ...

  • 3 Beds
  • 2 Baths
  • MDKE2006854 MLS
201 N Lynchburg St Unit #LOTS 4, 5, 6 & 7, Chestertown image
201 N Lynchburg St Unit #LOTS 4, 5, 6 & 7, Chestertown $300,000

4 Vacant Lots with many possiblilites. The project has the potential for a density change for 10 or more units. Buyer should do all necessary due diligency. Can also be s...

  • MDKE2006846 MLS
201 N Lynchburg St, Chestertown image
201 N Lynchburg St, Chestertown $500,000

A great opportunity for community mission driven organizations. The church and 5 additional parcels are all offered separately or together. Located in the heart of Cheste...

  • MDKE2006844 MLS
8999 Orchard Dr, Chestertown image
8999 Orchard Dr, Chestertown $824,900

Welcome to a breathtaking country estate where modern elegance, architectural grandeur, and total sanctuary converge across 2.23 serene acres. Spanning over 4,000 square ...

  • 5 Beds
  • 4 Baths
  • MDKE2006786 MLS
115 Metcalf Rd, Chestertown image
115 Metcalf Rd, Chestertown $259,900

Brand new home in Historic Chestertown available for move-in now. This interior unit features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitch...

  • 3 Beds
  • 2 Baths
  • MDKE2006826 MLS
107 Conley Dr, Chestertown image
107 Conley Dr, Chestertown $240,000

Welcome to easy, move in ready living in the heart of Chestertown! This fully renovated townhouse offers modern updates, low maintenance living, and an unbeatable locatio...

  • 3 Beds
  • 1 Baths
  • MDKE2006828 MLS
7828 Country Club Ln, Chestertown image
7828 Country Club Ln, Chestertown $799,000

Welcome to this spacious brick rancher located in the desirable Country Club Estates neighborhood, offering over 2,800 square feet of beautifully updated living space in ...

  • 3 Beds
  • 3 Baths
  • MDKE2006736 MLS
123 Heath Rd, Chestertown image
123 Heath Rd, Chestertown $349,000

Welcome to easy, one-level living in a location that truly gives you the best of both worlds! Just minutes from the charm and downtown, walkable, waterfront lifestyle of ...

  • 3 Beds
  • 2 Baths
  • MDQA2017994 MLS
200 Manor Ave, Chestertown image
200 Manor Ave, Chestertown $325,000

A rare opportunity to own a classic two-story split-level home in Chestertown — set on a large, shaded corner lot just a few miles to Downtown Chestertown, Washington Col...

  • 4 Beds
  • 2 Baths
  • MDKE2006808 MLS
305 Roosevelt Dr, Chestertown image
305 Roosevelt Dr, Chestertown $60,000

Nice cleared building lot in an established community. Public water and sewer available. Property recently acquired through tax sale foreclosure, recording is in process....

  • MDKE2006830 MLS
121 Metcalf Rd, Chestertown image
121 Metcalf Rd, Chestertown $264,900

Brand new home in Historic Chestertown available for move-in now. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with ...

  • 3 Beds
  • 2 Baths
  • MDKE2006678 MLS
200 High St, Chestertown image
200 High St, Chestertown $2,300,000

A rare turnkey, profitable, investment property in downtown Chestertown. Renovated to the studs in 2022, 200-202-204 High Street has 5 apartments and 3 storefronts and s...

  • MDKE2006810 MLS
233 Merganser Dr, Chestertown image
233 Merganser Dr, Chestertown $60,000

Vacant lot ready for your own choice of residence. Walking distance to the Chester River community access by boat or just enjoy the waterfront on the community deck.

  • MDQA2017912 MLS
21324 Persimmon Dr, Chestertown image
21324 Persimmon Dr, Chestertown $199,000

Welcome to this beautifully renovated 2-bedroom, 1-bath townhome offering the perfect blend of comfort, style, and convenience. Completely updated from top to bottom, thi...

  • 2 Beds
  • 1 Baths
  • MDKE2006816 MLS
10720 Foreston Rd, Chestertown image
10720 Foreston Rd, Chestertown $335,000

Welcome to 10720 Foreston Rd, a charming and inviting home situated in the peaceful surroundings of Chesapeake Landing in Chestertown, MD. 3 bedrooms and 2 full bathroom...

  • 3 Beds
  • 2 Baths
  • MDKE2006800 MLS
409 Calvert St, Chestertown image
409 Calvert St, Chestertown $155,000

Affordable opportunity in the heart of downtown Chestertown! This 3-bedroom, 1.5-bath townhome is ideally located just minutes from Washington College, shops, restaurants...

  • 3 Beds
  • 2 Baths
  • MDKE2006794 MLS
7680 Country Club Ln, Chestertown image
7680 Country Club Ln, Chestertown $885,000

Custom-built home in Country Club Estates with beautiful architectural details. Spacious open living space with hardwood floors and wooden beams, glowing with ample natur...

  • 5 Beds
  • 4 Baths
  • MDKE2006758 MLS
9126 Fairlee Rd, Chestertown image
9126 Fairlee Rd, Chestertown $344,000

Looking for peaceful country living? The search is over! Nestled on 1.66 acres, this beautifully renovated 3-bedroom, 1.5-bath home offers the perfect blend of comfort, f...

  • 3 Beds
  • 2 Baths
  • MDKE2006764 MLS
896 Washington Ave, Chestertown image
896 Washington Ave, Chestertown $325,000

A rare find! This rancher on Washington Ave has dual use: zoned residential and commercial. Full finished basement. More details and pictures coming soon!

  • 3 Beds
  • 1 Baths
  • MDKE2006750 MLS
517 Round Top Rd, Chestertown image
517 Round Top Rd, Chestertown $299,900 ▼

An exceptional opportunity to own this Single Level 3 bedroom 1 full bathrooms Ranch Style Home at a GREAT price nestled on an adorable lot. No need to worry about climbi...

  • 3 Beds
  • 1 Baths
  • MDQA2017680 MLS

Chestertown Real Estate -

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.

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Taylor Properties
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