Built in 1780/1840, "Highcroft" is in the heart of the Historic District near the Chester River. A rare in-town property that offers a 2-car garage with a second floor and a long driveway for tons of off-street parking. 3 bedrooms, 4 full baths and 1 half bath. Primary bedroom has his and hers private baths. 8.2 kw solar array on the garage. EV level 2 charger. Easy room flow from front to back for entertaining. Just steps to restaurants, bars, and shops. This is an ultra efficient "green" house.
Under contract
Price cut: $30K (6/3)
$798,000
407 High St, Chestertown, MD 21620
3beds
3,047sqft
Single Family Residence
Built in 1780
6,286 Square Feet Lot
$-- Zestimate®
$262/sqft
$-- HOA
What's special
- 61 days |
- 409 |
- 9 |
Zillow last checked:
Listing updated:
Listed by:
Lisa Raffetto 410-708-0174,
Coldwell Banker Chesapeake Real Estate Company 410-778-0330
Source: Bright MLS,MLS#: MDKE2006496
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 5
- Full bathrooms: 4
- 1/2 bathrooms: 1
- Main level bathrooms: 1
Rooms
- Room types: Living Room, Dining Room, Primary Bedroom, Bedroom 2, Bedroom 3, Kitchen, Family Room, Den, Laundry, Attic
Primary bedroom
- Features: Flooring - HardWood
- Level: Upper
- Area: 225 Square Feet
- Dimensions: 15 X 15
Bedroom 2
- Features: Flooring - HardWood
- Level: Upper
- Area: 256 Square Feet
- Dimensions: 16 X 16
Bedroom 3
- Features: Flooring - HardWood
- Level: Upper
- Area: 256 Square Feet
- Dimensions: 16 X 16
Other
- Features: Attic - Finished, Flooring - HardWood
- Level: Upper
Den
- Features: Flooring - HardWood
- Level: Main
- Area: 64 Square Feet
- Dimensions: 8 X 8
Dining room
- Features: Flooring - HardWood, Fireplace - Wood Burning
- Level: Main
- Area: 225 Square Feet
- Dimensions: 15 X 15
Family room
- Features: Flooring - HardWood, Fireplace - Gas
- Level: Main
- Area: 256 Square Feet
- Dimensions: 16 X 16
Kitchen
- Features: Flooring - HardWood, Fireplace - Other
- Level: Main
- Area: 225 Square Feet
- Dimensions: 15 X 15
Laundry
- Features: Flooring - HardWood
- Level: Main
Living room
- Features: Flooring - HardWood, Wood Stove
- Level: Main
- Area: 256 Square Feet
- Dimensions: 16 X 16
Mud room
- Features: Flooring - HardWood
- Level: Main
- Area: 64 Square Feet
- Dimensions: 8 X 8
Heating
- Forced Air, Heat Pump, Hot Water, Radiator, Wall Unit, Electric
Cooling
- Ductless, Electric
Appliances
- Included: Dishwasher, Cooktop, Down Draft, Disposal, Dryer, Exhaust Fan, Microwave, Oven, Refrigerator, Six Burner Stove, Washer, Gas Water Heater, Tankless Water Heater
- Laundry: Main Level, Laundry Room, Mud Room
Features
- Kitchen - Gourmet, Combination Kitchen/Living, Dining Area, Primary Bath(s), Crown Molding, Curved Staircase, Floor Plan - Traditional, Beamed Ceilings, Dry Wall, Plaster Walls, Tray Ceiling(s), Vaulted Ceiling(s)
- Flooring: Wood
- Doors: Sliding Glass
- Windows: Casement, Vinyl Clad, Double Pane Windows, Insulated Windows, Skylight(s), Storm Window(s), Wood Frames
- Basement: Exterior Entry,Connecting Stairway,Sump Pump,Other,Partial,Unfinished
- Number of fireplaces: 2
- Fireplace features: Gas/Propane, Mantel(s)
Interior area
- Total structure area: 3,047
- Total interior livable area: 3,047 sqft
- Finished area above ground: 3,047
- Finished area below ground: 0
Property
Parking
- Total spaces: 2
- Parking features: Garage Door Opener, Garage Faces Side, Off Street, Detached
- Garage spaces: 2
Accessibility
- Accessibility features: None
Features
- Levels: Three
- Stories: 3
- Patio & porch: Patio, Porch
- Pool features: None
- Fencing: Partial,Back Yard
Lot
- Size: 6,286 Square Feet
- Features: Landscaped
Details
- Additional structures: Above Grade, Below Grade
- Parcel number: 1504008561
- Zoning: R-5
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Victorian
- Property subtype: Single Family Residence
Materials
- Frame
- Foundation: Slab
- Roof: Metal,Asphalt
Condition
- Excellent
- New construction: No
- Year built: 1780
- Major remodel year: 2008
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Community & HOA
Community
- Subdivision: None Available
HOA
- Has HOA: No
Location
- Region: Chestertown
- Municipality: Chestertown
Financial & listing details
- Price per square foot: $262/sqft
- Tax assessed value: $705,567
- Annual tax amount: $10,781
- Date on market: 5/7/2026
- 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 | Contingent | $798,000$262/sqft |
Source:  Bright MLS #MDKE2006496 Report a problem | ||
| 6/3/2026 | Price change | $798,000-3.6%$262/sqft |
Source: Bright MLS #MDKE2006496 Report a problem | ||
| 5/7/2026 | Listed for sale | $828,000+20.9%$272/sqft |
Source: Bright MLS #MDKE2006496 Report a problem | ||
| 2/10/2016 | Listing removed | $685,000$225/sqft |
Source: Coldwell Banker Chesapeake Real Estate Company #KE8595980 Report a problem | ||
| 4/9/2015 | Listed for sale | $685,000-42.7%$225/sqft |
Source: Coldwell Banker Chesapeake Real Estate Company #KE8595980 Report a problem | ||
| 12/24/2008 | Listing removed | $1,195,000$392/sqft |
Source: Listhub #KE6744163 Report a problem | ||
| 8/22/2008 | Price change | $1,195,000-7.7%$392/sqft |
Source: Listhub #KE6744163 Report a problem | ||
| 5/25/2008 | Listed for sale | $1,295,000+223.7%$425/sqft |
Source: Listhub #KE6744163 Report a problem | ||
| 12/8/2006 | Sold | $400,000+150%$131/sqft |
Source: Public Record Report a problem | ||
| 6/30/1998 | Sold | $160,000$53/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $21,186 +107% | $687,900 +5.3% |
| 2024 | $10,233 +5.7% | $652,967 +5.7% |
| 2023 | $9,686 +6.7% | $618,033 +6% |
| 2022 | $9,080 +0.2% | $583,100 +0.8% |
| 2021 | $9,064 +0.8% | $578,333 +0.8% |
| 2020 | $8,989 +1% | $573,567 +0.8% |
| 2019 | $8,896 +0.6% | $568,800 |
| 2018 | $8,839 +3.3% | $568,800 |
| 2017 | $8,555 -0.8% | $568,800 |
| 2016 | $8,621 | $568,800 |
| 2015 | $8,621 | $568,800 |
| 2014 | $8,621 | $568,800 -0.8% |
| 2013 | -- | $573,200 |
| 2012 | -- | $573,200 |
| 2011 | -- | $573,200 -25.8% |
| 2010 | -- | $772,380 +12.2% |
| 2009 | -- | $688,132 +181.5% |
| 2008 | -- | $244,473 -16.5% |
| 2007 | -- | $292,930 +16% |
| 2006 | -- | $252,522 +18.8% |
| 2005 | -- | $212,506 +23.2% |
| 2004 | -- | $172,490 +6.6% |
| 2003 | -- | $161,842 +7% |
| 2002 | -- | $151,196 +7.6% |
| 2001 | -- | $140,550 |
Find assessor info on the county website
Monthly payment
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Payment breakdown
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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: 0.2 mi
- 2/10Kent County Middle SchoolGrades: 6-8Distance: 0.6 mi
- 5/10Kent County High SchoolGrades: 9-12Distance: 5.3 mi
Schools provided by the listing agent
- High: Kent County
- 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
- 407 High St
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