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Sold for $725,000
    • $725,000

    407 High St, Chestertown, MD 21620

    3beds
    3,047sqft
    Single Family Residence
    Built in 1780
    6,286 Square Feet Lot
    $724,500 Zestimate®
    $238/sqft
    $3,573 Estimated rent

    Home value

    $724,500

    Estimated sales range

    Not available

    $3,573/mo

    Zestimate® history
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    What's special

    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.

    Zillow last checked:

    Listing updated:

    Listed by:

    Lisa Raffetto 410-708-0174,

    Coldwell Banker Chesapeake Real Estate Company

    Bought with:

    Richard Keaveney, 662142

    Cross Street Realtors LLC

    Source: Bright MLS,MLS#: MDKE2006496MLS Logo

    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: $238/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

    Price history

    DateEventPrice
    9/8/2026Sold$725,000-9.1%$238/sqft
    Source: Bright MLS #MDKE2006496 Report a problem
    7/27/2026Pending sale$798,000$262/sqft
    Source: Bright MLS #MDKE2006496 Report a problem
    6/26/2026Contingent$798,000$262/sqft
    Source: Bright MLS #MDKE2006496 Report a problem
    6/3/2026Price change$798,000-3.6%$262/sqft
    Source: Bright MLS #MDKE2006496 Report a problem
    5/7/2026Listed for sale$828,000+20.9%$272/sqft
    Source: Bright MLS #MDKE2006496 Report a problem
    2/10/2016Listing removed$685,000$225/sqft
    Source: Coldwell Banker Chesapeake Real Estate Company #KE8595980 Report a problem
    4/9/2015Listed for sale$685,000-42.7%$225/sqft
    Source: Coldwell Banker Chesapeake Real Estate Company #KE8595980 Report a problem
    12/24/2008Listing removed$1,195,000$392/sqft
    Source: Listhub #KE6744163 Report a problem
    8/22/2008Price change$1,195,000-7.7%$392/sqft
    Source: Listhub #KE6744163 Report a problem
    5/25/2008Listed for sale$1,295,000+223.7%$425/sqft
    Source: Listhub #KE6744163 Report a problem
    12/8/2006Sold$400,000+150%$131/sqft
    Source: Public Record Report a problem
    6/30/1998Sold$160,000$53/sqft
    Source: Public Record Report a problem

    Public tax history

    YearProperty taxesTax assessment
    2025$10,593 +3.5%$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

    Neighborhood: 21620

    Nearby homes

    Nearby schools

    GreatSchools rating
    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.

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    Estimated market value
    $724,500
    Get a cash offer in 3 minutes
    Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
    Estimated market value
    $724,500

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