for sale

See all 48

for sale

48 photos

1 / 48

2 / 48

3 / 48

4 / 48

5 / 48

6 / 48

7 / 48

8 / 48

9 / 48

10 / 48

11 / 48

12 / 48

13 / 48

14 / 48

15 / 48

16 / 48

17 / 48

18 / 48

19 / 48

20 / 48

21 / 48

22 / 48

23 / 48

24 / 48

25 / 48

26 / 48

27 / 48

28 / 48

29 / 48

30 / 48

31 / 48

32 / 48

33 / 48

34 / 48

35 / 48

36 / 48

37 / 48

38 / 48

39 / 48

40 / 48

41 / 48

42 / 48

43 / 48

44 / 48

45 / 48

46 / 48

47 / 48

48 / 48

$1,395,500

5beds

5baths

3,243sqft

1863built

105 High St,Chestertown, MD 21620

Est.$9,176/moCustomize payment

What's special

$430/sqft

Price per square foot

Built in 1863

163 years old

1 parking spaces

Garage

Overview

Rebuilt in 1863, the Tilley Residence showcases classic Second Empire architecture on one of Chestertown's most prominent historic corners across from the Custom House, one of the first British Royal Ports of Entry to the Americas. Completely restored in 2025 by one of the Eastern Shore's iconic builders, the home blends historic character with modern comfort through thoughtful updates, new systems, and refined living spaces. Just one block to the waterfront promenade or to morning coffee at Evergrain, the location captures the rhythm of Chestertown living - laid back yet polished, historic ye...

Listed on November 7, 2025 · Source: MLS #MDKE2005890