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$1,245,500

Listing Price

5beds

4baths

3,243sqft

2,688sqft lot

105 High St, Chestertown, MD 21620

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  • Full foreclosure details

  • Home value, equity and ownership info

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For Sale

Off Market

Single Family

Home type

430.31

Price / sqft

1900

Year built

Home Details

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 yet vibrant. This is more than a home; it is an irreplaceable asset and a true legacy property within one of Maryland's most beloved waterfront towns.

Interior Details

Square Feet
  • 3243

Bedrooms
  • 5

Bathrooms
  • 4

Heating
  • Has Heating:

    Yes

  • Heating Type:

    Heat Pump

Cooling
  • Has Cooling:

    Yes

  • Cooling Type:

    N/A

Fuel
  • Has Fuel:

    No

  • Fuel Type:

    N/A

Basement
  • Has Basement:

    No

  • Basement Type:

    Finished

Flooring
  • Has Flooring:

    No

  • Flooring Type:

    N/A

Fireplace
  • Has Fireplace:

    Yes

  • Fireplace Type:

    N/A

Property Details

Lot Size
  • 2688

Water
  • Yes

Sewer
  • Yes

Parking
  • Type:

    Garage, Detached

  • Location:

    N/A

  • Status:

    N/A

  • Number of Spaces:

    1

Deck
  • No

Patio
  • No

Fence
  • No

Pool
  • No

Porch
  • No

Stoop
  • No

Breezeway
  • No

Construction Details

Number of Stories
  • 3

Style
  • Conventional

Exterior
  • Wood Shingle

Foundation
  • N/A

Roof
  • N/A

Roofing Material
  • Wood Shingle

Tax History

Year

Amount

Land

Improvement

Percent Change

Assessment

2021

$7,673

$0

$0

--%

$489,633

2020

$15,209

$350,600

$137,200

--%

$487,800

2019

$7,580

$350,600

$137,200

--%

$487,800

2018

$6,279

$350,600

$137,200

--%

$487,800

2017

$6,006

$350,600

$137,200

--%

$487,800

2015

$5,498

$350,600

$137,200

--%

$487,800

2014

$2,636

$350,600

$145,200

--%

$495,800

2012

$5,022

$0

$0

--%

$495,800

percent-home-icon

Average Home Price in 21620

Nearby Properties

Zip Code

Price

Bed

Bath

Sqft

Lot

Sold Date

$690,155

-- Beds

2 Baths

3,178 Sqft

3,000 Lot (sqft)

Sold 09/16/2026

$1,029,658

-- Beds

2.5 Baths

3,189 Sqft

4,457 Lot (sqft)

Sold 09/09/2026

$1,009,820

-- Beds

3.5 Baths

2,786 Sqft

5,900 Lot (sqft)

Sold 07/07/2026

$949,004

-- Beds

2.5 Baths

3,034 Sqft

8,181 Lot (sqft)

Sold 05/20/2026

$1,250,000

5 Beds

5 Baths

3,247 Sqft

10,977 Lot (sqft)

Sold 09/29/2026

$695,000

4 Beds

3.5 Baths

2,869 Sqft

9,100 Lot (sqft)

Sold 09/29/2026

$828,000

3 Beds

5 Baths

3,047 Sqft

6,286 Lot (sqft)

Sold 10/05/2026

$395,000

7 Beds

4 Baths

3,664 Sqft

5,737 Lot (sqft)

Sold 09/29/2026

$968,866

-- Beds

3.5 Baths

3,030 Sqft

4,066 Lot (sqft)

Sold 10/05/2026

percent-home-icon

Calculators

Mortgage

Mortgage Calculator

Calculate your monthly mortgage payments.
Household Income
70,000
$
Home price
1,245,500
$
Down payment
249,100
$
Mortgage Rate
6.5
%
Loan Term
Property Tax Rate
1.1
%
Homeowner's Insurance (Annual)
7,473
$
HOA (Monthly)
0
$
PMI
0
$
$8,062
Your Payment
Total Monthly Payment:$8,062
Percent of Income:138%
Affordable:No

Details for 105 HIGH ST

Property Debt

Foreclosure Contact Details

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