407 High St

Chestertown, MD 21620

$828,000
Price
3
Beds
3,047 Sq. Ft.
$272 / Sq. Ft.
3,047
Sq. Ft.
$272
per Sq. Ft.
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Coming SoonOpen: 5/9 10:00AM - 01:00PM
Coming SoonOpen: 5/9 10:00AM - 01:00PM

Description

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. 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. More details and pictures coming soon!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. 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. More details and pictures coming soon!
  1. Listed by Lisa P Raffetto • Coldwell Banker Chesapeake Real Estate Company
    P: (410)-708-0174 lisar@cbchesapeake.com

Property Details for 407 High Street

Tax ID Number
1504008561
Ownership
Fee Simple
Condo Coop Association
No
HOA
No
Structure Type
Detached
Style
Victorian
Levels/Stories
3
Waterfront
No

Open Houses

Saturday, May 9th10:00 AM - 1:00 PM
PublicView contact
LISTING UPDATED: 05/03/2026 11:29 AM

Property Details for 407 High Street

StatusComing Soon
MLS #MDKE2006496
Days on Market-
Taxes$10,781 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential / Fee Simple
Year Built1780
Lot Size0.14 AC / 6,286 SF
CountyKent County
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Location

Listing Courtesy of Coldwell Banker Chesapeake Real Estate Company
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Building Information for 407 High Street

Stories3Year Built1780Building Size-Lot Size0.14 AC / 6,286 SF

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$5,068 per month

30 year fixed, 6.46% Interest

Principal and Interest

$4,169

Property Taxes

$898

HOA Dues

$0

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Property Information for 407 High Street

Location
Location
  • In City Limits: Yes
  • School District Name: KENT COUNTY PUBLIC SCHOOLS
  • School District County ID: 121139164602
  • SchoolDistrictSource: Listing Agent
  • High School: KENT COUNTY (KENT MD)
  • County: KENT
Waterfront / Water Access
Waterfront / Water Access
  • Water View: No
  • Water Access: No
  • Water Oriented: No
  • Navigable Water: No
  • Tidal Water: No
  • Riparian Rights Y/N: No
Association / Community Info
Association / Community Info
  • Senior Community: No
Taxes and Assessment
Taxes and Assessment
  • Tax Year: 2025
  • Tax Assessed Value: $705,567
  • Year Assessed: 2026
  • County Tax: $7,801
  • Improvement Assessed Value: $536,700
  • City Town Tax: $2,979
  • Land Assessed Value: $204,200
  • Clean Green Assessed: No
  • Land Use Code: R
  • Historic: Yes
  • Zoning: R-5
  • Tax Lot: 6
  • School Tax: $0
  • Tax Page Number: 487
  • Automatically Update Tax Values Y/N: Yes
Rooms
Main
  • # Bedrooms Count Main Level: 0
  • # Bathrooms Count Main Level: 1
  • # Bathrooms Full Main Level: 0
  • # Bathrooms Half Main Level: 1
All Upper Levels
  • # Bedrooms Count All Upper Levels: 3
  • # Bathrooms Count All Upper Levels: 3
  • # Bathrooms Full All Upper Levels: 3
  • # Bathrooms Half All Upper Levels: 0
Upper Level 1
  • # Bedrooms Count Upper Level: 2
  • # Bathrooms Count Upper Level: 2
  • # Bathrooms Full Upper Level: 2
  • # Bathrooms Half Upper Level: 0
Upper Level 2
  • # Bedrooms Count Upper Level: 1
  • # Bathrooms Count Upper Level: 1
  • # Bathrooms Full Upper Level: 1
  • # Bathrooms Half Upper Level: 0
Rooms
  • Room List: Living Room, Dining Room, Primary Bedroom, Bedroom 2, Bedroom 3, Kitchen, Family Room, Den, Laundry, Mud Room, Attic
  • Stories: Main, Upper 1, Upper 2
Rooms Information
Room 1
  • Room Type: Primary Bedroom
  • Room Length: 15.0
  • Room Width: 15.0
  • Room Level: Upper 1
  • Room Exists: Yes
  • Room Dimensions: 15 X 15
  • Room Features: Flooring - HardWood
Room 2
  • Room Type: Attic
  • Room Level: Upper 2
  • Room Exists: Yes
  • Room Features: Attic - Finished, Flooring - HardWood
Room 3
  • Room Type: Bedroom 2
  • Room Length: 16.0
  • Room Width: 16.0
  • Room Level: Upper 1
  • Room Exists: Yes
  • Room Dimensions: 16 X 16
  • Room Features: Flooring - HardWood
Room 4
  • Room Type: Bedroom 3
  • Room Length: 16.0
  • Room Width: 16.0
  • Room Level: Upper 2
  • Room Exists: Yes
  • Room Dimensions: 16 X 16
  • Room Features: Flooring - HardWood
Room 5
  • Room Type: Dining Room
  • Room Length: 15.0
  • Room Width: 15.0
  • Room Level: Main
  • Room Exists: Yes
  • Room Dimensions: 15 X 15
  • Room Features: Flooring - HardWood, Fireplace - Wood Burning
Room 6
  • Room Type: Kitchen
  • Room Length: 15.0
  • Room Width: 15.0
  • Room Level: Main
  • Room Exists: Yes
  • Room Dimensions: 15 X 15
  • Room Features: Flooring - HardWood, Fireplace - Other
Room 7
  • Room Type: Laundry
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Flooring - HardWood
Room 8
  • Room Type: Mud Room
  • Room Length: 8.0
  • Room Width: 8.0
  • Room Level: Main
  • Room Exists: Yes
  • Room Dimensions: 8 X 8
  • Room Features: Flooring - HardWood
Room 9
  • Room Type: Family Room
  • Room Length: 16.0
  • Room Width: 16.0
  • Room Level: Main
  • Room Exists: Yes
  • Room Dimensions: 16 X 16
  • Room Features: Flooring - HardWood, Fireplace - Gas
Room 10
  • Room Type: Living Room
  • Room Length: 16.0
  • Room Width: 16.0
  • Room Level: Main
  • Room Exists: Yes
  • Room Dimensions: 16 X 16
  • Room Features: Flooring - HardWood, Wood Stove
Room 11
  • Room Type: Den
  • Room Length: 8.0
  • Room Width: 8.0
  • Room Level: Main
  • Room Exists: Yes
  • Room Dimensions: 8 X 8
  • Room Features: Flooring - HardWood
Building Info
Building Info
  • Year Major Reno Remodel: 2008
  • Total Finished SQFT: 3,047.00
  • Total Finished SQFT Source: Assessor
  • Tax Total Finished SQFT: 3,047.00
  • Total SQFT: 3,047.00
  • Total SQFT Source: Assessor
  • Construction Materials: Frame
  • Roof: Metal, Asphalt
  • Ext Main Mid-res: http://bright-media02.prd.brightmls.com/bright/images/0000/8048/6905/8748/804869058748_512_384_WM_zRmSHBXCiyyThQ_4.jpg
  • Wall and Ceiling Types: Beamed Ceilings, Dry Wall, Plaster Walls, Tray Ceilings, Vaulted Ceilings
  • Basement Type: Outside Entrance, Connecting Stairway, Sump Pump, Other, Partial, Unfinished
  • Foundation Details: Slab
  • Room and Floor: Bathrooms Half-Main Level-1, Bedrooms-Upper Level 1-1, Bedrooms-Upper Level 1-2, Bathrooms Full-Upper Level 1-1, Bathrooms Full-Upper Level 1-2, Bedrooms-Upper Level 2-1, Bathrooms Full-Upper Level 2-1
  • # Bathrooms Full: 3
  • # Bathrooms Half: 1
  • Other Structure: Garage(s)
Lot / Land Information
Lot / Land Information
  • Lot Size Source: Assessor
  • Lot Features: Landscaping
  • Road Responsibility: City/County
  • Fencing: Partially, Rear
  • Parcel ID: 4504806
Parking
Parking
  • Type Of Parking: Off Street, Detached Garage
  • Num of Detached Garage Spaces: 2
  • Total Garage Spaces: 2
  • Garage Features: Garage Door Opener, Garage - Side Entry
Interior Features
Interior Features
  • Interior Features: Kitchen - Gourmet, Combination Kitchen/Living, Dining Area, Primary Bath(s), Crown Moldings, Curved Staircase, Wood Floors, Floor Plan - Traditional
  • Fireplace: Yes
  • Fireplaces Count: 2
  • Fireplace Features: Gas/Propane, Mantel(s)
  • Appliances: Dishwasher, Cooktop, Cooktop - Down Draft, Disposal, Dryer, Exhaust Fan, Microwave, Oven - Wall, Refrigerator, Six Burner Stove, Washer
  • Accessibility Features: None
  • Door Features: Sliding Glass
  • Window Features: Casement, Vinyl Clad, Double Pane, Insulated, Skylights, Storm, Wood Frame
  • Laundry Type: Main Floor
Exterior Features
Exterior Features
  • Outdoor Living Structures: Patio(s), Porch(es)
  • Pool: No Pool
Utilities
Utilities
  • Heating: Yes
  • Cooling Type: Ductless/Mini-Split
  • Cooling Fuel: Electric
  • Heating Type: Forced Air, Heat Pump(s), Hot Water, Radiator, Wall Unit
  • Heating Fuel: Electric
  • Hot Water: Bottled Gas, Tankless
  • Water Source: Public
  • Sewer Septic: Public Sewer
Confidential Data
Listing Office
  • List Agent AOR: Bay Area Association of REALTORS
  • List Agent URL: www.lisaraffetto.com

Property History for 407 High Street

DateEvent & SourcePriceAppreciation
Jan 22, 2016

Withdrawn

BRIGHT #1007887218

—
Apr 7, 2015

Listed (Active)

BRIGHT #1007887218

$685,000—
Dec 19, 2008

Withdrawn

BRIGHT #1008475246

$1,195,000—
DateEvent & SourcePrice
01/22/2016

Withdrawn

BRIGHT #1007887218

—
04/07/2015

Listed (Active)

BRIGHT #1007887218

$685,000
12/19/2008

Withdrawn

BRIGHT #1008475246

$1,195,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 407 High Street

Taxable ValueLand$204,200Additions$483,700Total$687,900
Tax Record2025$10,593 ($883 / month)
Home Facts
Beds0Baths4.5Total Finished SqFt3,047 SqFtAbove Grade Finished SqFt3,047 SqFtStories3Lot Size6,286 SqFtStyleSingle Family ResidenceYear Built1900ZoningR-5CountyKENTAPN04-008561Fireplace TypeHas Fireplace

Schools near 407 High Street

This home is within Kent County Public Schools.
Rating
School
Type
Grades
Distance
H. H. Garnett Elementary School
Public - PK to 5
Kent County Middle School
Public - 6 to 8
Kent County High School
Public - 9 to 12
Rock Hall Elementary School
Public - PK to 5
Rating
School
Distance
H. H. Garnett Elementary School
PublicPK to 5

Kent County Middle School
Public6 to 8

Kent County High School
Public9 to 12

Rock Hall Elementary School
PublicPK to 5

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 407 High Street, Chestertown, MD 21620

407 High Street is a single family home Coming Soon in Chestertown, MD 21620. This property is currently priced at $828,000. This listing's school district is Kent County Public Schools. Nearby schools include H. H. Garnett Elementary School, Kent County Middle School and Kent County High School. 407 High Street is a 3-bed, 4-bath, 3,047 sqft single family home built in 1780.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Coldwell Banker Chesapeake Real Estate Company

© 2026 Bright MLS. All rights reserved. All information is deemed reliable, but accuracy is not guaranteed. Listing information is from various brokers who participate in IDX and not all listings may be visible on the site. The property information being provided is for the consumer’s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated on 05/03/2026 11:29 AM