For Sale154d on marketHistoric · 163 yrs
105 High St
Chestertown, MD, 21620 • 21620 • Kent County
$1,395,500
$430/sqft
Down payment assistance available
5Beds
5Baths
3,243Sqft
0.06 acLot
1863Built
Property DNA
Waterfront Property
River
Scenic Views
Water · Scenic Vista · River
Victorian Style
Built 1863 · 163 years of history
Chestertown Historic District
21620
Outdoor Living
Porch · Patio
2 Fireplaces
Cozy heat source
Special Features
Above Grade · Below Grade
1-Car Garage
Garage Faces Side · Detached
This home is getting attention
Listed 154 days ago · 699 views · 10 saves
Market activity
Demand and pricing signals for this listing
699 views
People checking out this listing
10 saves
Buyers have saved this home
154 days on market
Established listing
$430/sqft
Price per square foot
About this home
Single Family · Built 1863 · Historic
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.
Standout features identified
Our analysis highlights prominent historic corners, refined living spaces, and classic second empire architecture as key attractions of this home.
Estimated monthly payment
Based on current rates
$8,789/month
Principal & Interest$6,928
Property Tax$1,396
Insurance$465
Down payment20% ($279,100)
3%50%
Est. 6.33% rate · 30yr fixed · $1,116,400 loan
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At a glance
Key facts and listing details
TypeSingle Family Residence
Year Built1863
HeatingHeat Pump, Electric, Propane
CoolingCentral Air, Electric
Parking1 Garage space
Lot2,688 sqft
Days on Zillow154 Days
Price/sqft$430
Property
Home typeSingle Family
Sub-typeSingle Family Residence
StyleVictorian
Year built1863
Stories4
Systems
HeatingHeat Pump, Electric, Propane
CoolingCentral Air, Electric
ConstructionFrame
Water / SewerPublic / Public Sewer
Parking & Outdoor
ParkingGarage Faces Side, Detached
Garage1 spaces
BasementImproved,Interior Entry
Fireplaces2
Lot2,688 sqft
Location & Tax
Neighborhood21620
ZoningR-3
Annual tax$20,218
Parcel04018273
Bathrooms & Fees
Full baths4
Features & details
11 categories of property features
Interior Features
Appliances
Water Heater
Heating
Heat Pump
Electric
Propane
Cooling
Central Air
Electric
Accessibility
None
Exterior Features
Parking
Garage Faces Side
Detached
Construction
Frame
Patio & Porch
Porch
Patio
Lot Features
Downtown
Views
Water
Scenic Vista
River
Pool Features
None
Other Structures
Above Grade
Below Grade
Room details
10 rooms detailed
Bedroom1
UpperBedroom1
UpperBedroom2
UpperBedroom2
UpperBedroom3
UpperBathroom1
MainListing insights
Market data and value estimates
StatusFor Sale
Days on market154
Tax rate0.94%
Price/sqft$430
On marketNov 7, 2025
PostedNov 7, 2025
Last sold$200,000
MLS updatedMar 23, 2026
Tour days9
Views699
Favorites10
How are the schools in Chestertown?
3 schools rated nearby
Location
Chestertown, MD, 21620
Price history
5 events
DateEventPrice$/sqftSource
Nov 7, 2025Listed For Sale$1,395,500$430Bright MLS
Nov 7, 2025Listing Removed$1,395,500$430Bright MLS
Apr 29, 2025Price Change$1,395,500$430Bright MLS
Mar 28, 2025Listed For Sale$1,395,000$430Bright MLS
Sep 7, 2022Sold$200,000$62Public Record
Listed For Sale$1,395,500
Nov 7, 2025•$430/sqft•Bright MLS
Listing Removed$1,395,500
Nov 7, 2025•$430/sqft•Bright MLS
Price Change$1,395,500
Apr 29, 2025•$430/sqft•Bright MLS
Listed For Sale$1,395,000
Mar 28, 2025•$430/sqft•Bright MLS
Sold$200,000
Sep 7, 2022•$62/sqft•Public Record
Tax history
25 years of records
YearTax paidAssessed value
Apr 10, 2025$40,437$1,290,100
Apr 10, 2024$9,934$633,867
Apr 10, 2023$7,970$508,533
Apr 10, 2022$7,682$493,300
Apr 10, 2021$7,702$491,467
Apr 10, 2020$7,674$489,633
Apr 10, 2019$7,629$487,800
Apr 10, 2018$7,580$487,800
Apr 10, 2017$7,337$487,800
Apr 10, 2016$4,761$487,800
Apr 10, 2015$4,761$487,800
Apr 10, 2014$4,761$487,800
Apr 10, 2013—$495,800
Apr 10, 2012—$495,800
Apr 10, 2011—$495,800
Apr 10, 2010—$579,330
Apr 10, 2009—$537,380
Apr 10, 2008—$495,430
Apr 10, 2007—$453,480
Apr 10, 2006—$376,012
Apr 10, 2005—$298,546
Apr 10, 2004—$221,080
Apr 10, 2003—$208,760
Apr 10, 2002—$196,440
Apr 10, 2001—$184,120
Nearby homes
Neighborhood details
Local context around this listing
Chestertown, MD • Kent County
Nearby neighborhoods
Chesapeake Landing
Nearby cities
BettertonChestertownGalenaGeorgetownKennedyvilleMasseyMillingtonRock Hall
Nearby zip codes
2162021690
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