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.
For sale
Price cut: $50K (6/26)
$1,245,500
105 High St, Chestertown, MD 21620
5beds
3,243sqft
Single Family Residence
Built in 1863
2,688 Square Feet Lot
$-- Zestimate®
$384/sqft
$-- HOA
What's special
Prominent historic cornersRefined living spacesClassic second empire architectureCompletely restoredNew systemsThoughtful updates
- 237 days |
- 544 |
- 6 |
Zillow last checked:
Listing updated:
Listed by:
Murphy ONeill 443-480-4275,
Coldwell Banker Chesapeake Real Estate Company 410-778-0330
Source: Bright MLS,MLS#: MDKE2005890
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Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 5
- Full bathrooms: 4
- 1/2 bathrooms: 1
- Main level bathrooms: 2
Rooms
- Room types: Bedroom 2, Bedroom 3, Bedroom 1, Bathroom 1, Bathroom 2, Half Bath
Bedroom 1
- Level: Upper
Bedroom 1
- Level: Upper
Bedroom 2
- Level: Upper
Bedroom 2
- Level: Upper
Bedroom 3
- Level: Upper
Bathroom 1
- Level: Main
Bathroom 1
- Level: Upper
Bathroom 1
- Level: Upper
Bathroom 2
- Level: Upper
Half bath
- Level: Main
Heating
- Heat Pump, Electric, Propane
Cooling
- Central Air, Electric
Appliances
- Included: Water Heater
Features
- Basement: Improved,Interior Entry
- Number of fireplaces: 2
Interior area
- Total structure area: 4,235
- Total interior livable area: 3,243 sqft
- Finished area above ground: 3,243
- Finished area below ground: 0
Video & virtual tour
Property
Parking
- Total spaces: 1
- Parking features: Garage Faces Side, Detached
- Garage spaces: 1
Accessibility
- Accessibility features: None
Features
- Levels: Four
- Stories: 4
- Patio & porch: Porch, Patio
- Pool features: None
- Has view: Yes
- View description: Water, Scenic Vista, River
- Has water view: Yes
- Water view: Water,River
- Waterfront features: River
Lot
- Size: 2,688 Square Feet
- Features: Downtown
Details
- Additional structures: Above Grade, Below Grade
- Parcel number: 1504018273
- Zoning: R-3
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Victorian
- Property subtype: Single Family Residence
Materials
- Frame
- Foundation: Permanent
Condition
- New construction: No
- Year built: 1863
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Community & HOA
Community
- Subdivision: Chestertown Historic District
HOA
- Has HOA: No
Location
- Region: Chestertown
- Municipality: Chestertown
Financial & listing details
- Price per square foot: $384/sqft
- Tax assessed value: $1,290,100
- Annual tax amount: $20,218
- Date on market: 11/7/2025
- Listing agreement: Exclusive Right To Sell
- Ownership: Fee Simple
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
| Date | Event | Price |
|---|---|---|
| 6/26/2026 | Price change | $1,245,500-3.9%$384/sqft |
Source:  Bright MLS #MDKE2005890 Report a problem | ||
| 5/1/2026 | Price change | $1,295,500-7.2%$399/sqft |
Source: Bright MLS #MDKE2005890 Report a problem | ||
| 11/7/2025 | Listed for sale | $1,395,500$430/sqft |
Source: Bright MLS #MDKE2005890 Report a problem | ||
| 11/7/2025 | Listing removed | $1,395,500$430/sqft |
Source: Bright MLS #MDKE2005002 Report a problem | ||
| 4/29/2025 | Price change | $1,395,500+0%$430/sqft |
Source: Bright MLS #MDKE2005002 Report a problem | ||
| 3/28/2025 | Listed for sale | $1,395,000+597.5%$430/sqft |
Source: Bright MLS #MDKE2005002 Report a problem | ||
| 9/7/2022 | Sold | $200,000$62/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $40,437 +307.1% | $1,290,100 +103.5% |
| 2024 | $9,934 +24.6% | $633,867 +24.6% |
| 2023 | $7,970 +3.7% | $508,533 +3.1% |
| 2022 | $7,682 -0.3% | $493,300 +0.4% |
| 2021 | $7,702 +0.4% | $491,467 +0.4% |
| 2020 | $7,674 +0.6% | $489,633 +0.4% |
| 2019 | $7,629 +0.6% | $487,800 |
| 2018 | $7,580 +3.3% | $487,800 |
| 2017 | $7,337 +54.1% | $487,800 |
| 2016 | $4,761 | $487,800 |
| 2015 | $4,761 | $487,800 |
| 2014 | $4,761 | $487,800 -1.6% |
| 2013 | -- | $495,800 |
| 2012 | -- | $495,800 |
| 2011 | -- | $495,800 -14.4% |
| 2010 | -- | $579,330 +7.8% |
| 2009 | -- | $537,380 +8.5% |
| 2008 | -- | $495,430 +9.3% |
| 2007 | -- | $453,480 +20.6% |
| 2006 | -- | $376,012 +25.9% |
| 2005 | -- | $298,546 +35% |
| 2004 | -- | $221,080 +5.9% |
| 2003 | -- | $208,760 +6.3% |
| 2002 | -- | $196,440 +6.7% |
| 2001 | -- | $184,120 |
Find assessor info on the county website
Monthly payment
Est. payment$--/mo
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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Climate risks
Neighborhood: 21620
Nearby schools
GreatSchools rating
- 7/10H. H. Garnett Elementary SchoolGrades: PK-5Distance: 0.5 mi
- 2/10Kent County Middle SchoolGrades: 6-8Distance: 0.7 mi
- 5/10Kent County High SchoolGrades: 9-12Distance: 5.6 mi
Schools provided by the listing agent
- District: Kent County Public Schools
Source: Bright MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
A local agent can set up tours, give advice and negotiate with sellers.
- Maryland
- Kent County
- Chestertown
- 21620
- 105 High St
Nearby cities
Nearby neighborhoods
Nearby zip codes
Other Chestertown Topics
