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Newest Property Listings In Chestertown

201 Silver Heel Dr, Chestertown image
201 Silver Heel Dr, Chestertown $329,990

The Sidney, a move-in ready 1,849 square-foot open concept two-story home, features four bedrooms, and two and a half bathrooms. A welcoming foyer with a coat closet gree...

  • 4 Beds
  • 3 Baths
  • MDKE2002516 MLS
209 Silver Heel Dr, Chestertown image
209 Silver Heel Dr, Chestertown $309,990

Ready to move in, the Paige is a 1,646 square foot two-story home, that features three bedrooms, and two and a half bathrooms. You will immediately feel at home as you en...

  • 3 Beds
  • 3 Baths
  • MDKE2002514 MLS
211 Silver Heel Dr, Chestertown image
211 Silver Heel Dr, Chestertown $324,990

New move-in ready home in The Village at Chestertown! The Sidney is a 1,849 square-foot two-story home that features four bedrooms, and two and a half bathrooms. A welcom...

  • 4 Beds
  • 3 Baths
  • MDKE2002512 MLS
213 Silver Heel Dr, Chestertown image
213 Silver Heel Dr, Chestertown $321,990

New move-in ready home in The Village at Chestertown! The Paige is a 1,646 square foot two-story home that features three bedrooms, and two and a half bathrooms. You will...

  • 3 Beds
  • 3 Baths
  • MDKE2002510 MLS
211 Manor Ave, Chestertown image
211 Manor Ave, Chestertown $249,900

Here's a little gem with heaps of potential, just needs TLC....Spacious rancher with 3 bedrooms, 1.5 baths, living room with Fireplace, kitchen, dining area, family room ...

  • 3 Beds
  • 2 Baths
  • MDKE2002502 MLS
9048 Georgetown Rd, Chestertown image
9048 Georgetown Rd, Chestertown $50,000

Buildable parcel with the possibility of subdividing into 2 lots.

  • MDKE2002504 MLS
212 Silver Heel Ct, Chestertown image
212 Silver Heel Ct, Chestertown $339,990

Affordable, Adorable, New Construction! - There's an opening in the coveted community of The Village at Chestertown! - New Construction without the wait - Turnkey and rea...

  • 5 Beds
  • 4 Baths
  • MDKE2002496 MLS
7755 Waterview Ln, Chestertown image
7755 Waterview Ln, Chestertown $1,290,000

This circa 2011, white brick house was built to celebrate the expansive views over the Chester River Yacht &Country Club golf course to the Chester River. There is an at...

  • 4 Beds
  • 3 Baths
  • MDKE2002490 MLS
114 Riverside Ter Unit #6, Chestertown image
114 Riverside Ter Unit #6, Chestertown $340,000

A delightful 2 bedroom 1 bath Duplex Condo in the lovely Riverside Terrace community. The unit has been well-maintained and has breathtaking water views from the front ya...

  • 2 Beds
  • 1 Baths
  • MDKE2002430 MLS
611 Cannon St, Chestertown image
611 Cannon St, Chestertown $240,000

Just a few blocks away from the heart of downtown Chestertown, this bungalow could be your perfect home, or great investment property. With a large kitchen and dining ro...

  • 2 Beds
  • 2 Baths
  • MDKE2002432 MLS
109 Water St N, Chestertown image
109 Water St N, Chestertown $1,198,500

Welcome to the Esau Watkins House (circa 1739), believed to be the earliest remaining dwelling on the Chester River in Historic Chestertown, the capitol of Kent County, M...

  • 5 Beds
  • 4 Baths
  • MDKE2002442 MLS
Berwyn Rd Unit #LOTS 269 & 270, Chestertown image
Berwyn Rd Unit #LOTS 269 & 270, Chestertown $289,900

Come by this lovely BRAND NEW home in quaint Waterfront Community of Chesapeake Landing. This home features Luxury Vinyl & Carpet Flooring throughout, White Shaker Style ...

  • 3 Beds
  • 3 Baths
  • MDKE2002418 MLS
10720 Augustine Herman Hwy, Chestertown image
10720 Augustine Herman Hwy, Chestertown $369,000

Imagine the possibilities of a business along a major highway in Kent County with a traffic count of 3,362 cars a day (2019). Previously used as an animal shelter, it's a...

  • MDKE2002416 MLS
Caulks Field Road, Chestertown image
Caulks Field Road, Chestertown $75,000 ▲

Two-acre wooded lot with road frontage on Caulks Field Road, Kent Co., MD. Zoned AZD,Village District; land use: Residential. Planned public water/sewer service area. ...

  • MDKE2002188 MLS
Georgetown Rd Se, Chestertown image
Georgetown Rd Se, Chestertown $60,000 ▲

Two-acre wooded lot located SE Georgetown Road, West of Chestertown. Zoned Village District. Planned water/sewer service area. No public water/sewer allocation at this...

  • MDKE2002190 MLS
206 Silver Heel Dr, Chestertown image
206 Silver Heel Dr, Chestertown $339,990 ▼

New move-in ready home in The Village at Chestertown! The Verona, a 2,302 square foot, three-story home, offers five bedrooms, and three and a half bathrooms. This well-d...

  • 5 Beds
  • 4 Baths
  • MDKE2002406 MLS
702 Deep Landing Rd, Chestertown image
702 Deep Landing Rd, Chestertown $349,900 ▼

PRICE REDUCED!!!Built in 2020 this nearly new 3 Bedroom 2 full bath rancher offers split open concept living all on 1 level. Many upgrades include 200 amp service with ex...

  • 3 Beds
  • 2 Baths
  • MDQA2005792 MLS
207 N Queen St, Chestertown image
207 N Queen St, Chestertown $819,900 ▼

New price! Wait until you see this beautiful renovation! No detail has been overlooked in this open-concept historic Chestertown gem. The owners were able to achieve t...

  • 4 Beds
  • 2 Baths
  • MDKE2002388 MLS
98 Cannon St, Chestertown image
98 Cannon St, Chestertown $1,290,000

Don’t miss out on the opportunity to own this restaurant and bar located in Historic Downtown Chestertown. 98 Cannon offers both indoor and outdoor dining with panoramic ...

  • MDKE2002356 MLS
716 Deep Landing Rd, Chestertown image
716 Deep Landing Rd, Chestertown $348,500 ▼

You won't want to miss this STUNNING rancher in Pine Cove! This home is located in Queen Anne's County and is only 5 years old. The home offers 3 bedrooms and 2 full bath...

  • 3 Beds
  • 2 Baths
  • MDQA2005712 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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