Date
Details
Price
Change
Source
5/07/2026
Listed
$828,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
1/3
$828,000 Just Listed
This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
1/3
Property 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. # 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.
Full Property Details
Full Property Details for 407 High St
General
- Price: $828,000
- Taxes: $10,781 (2025)
- Status: Active
- Type: Single Family
- Source: BrightMLSMidAtlantic
- MLS ID: MDKE2006496
- Updated: Today (5/7/2026)
- Added to Site: Today
Interior
- Rooms/Areas: Living Room, Dining Room, Primary Bedroom, Bedroom 2, Bedroom 3, Kitchen, Family Room, Den, Laundry, Mud Room, Attic
- Interior Features: Kitchen - Gourmet, Combination Kitchen/Living, Dining Area, Primary Bath(s), Crown Moldings, Curved Staircase, Wood Floors, Floor Plan - Traditional
- Fireplace: Yes
- Number of Fireplaces: 2
- Fireplace(s): Gas/Propane, Mantel(s)
- Appliances: Dishwasher, Cooktop, Cooktop - Down Draft, Disposal, Dryer, Exhaust Fan, Microwave, Oven - Wall, Refrigerator, Six Burner Stove, Washer
Rooms
Bathrooms
- Total Bathrooms: 4
- Full Bathrooms: 3
- Half Bathrooms: 1
- Upper 2 - Full Baths: 1
- Upper Floor Baths: 3
- Upper - Full Baths: 3
- Main Floor Baths: 1
- Main - 1/2 Baths: 1
Bedrooms
- Total Bedrooms: 3
- Bedrooms Upper: 3
- Bedrooms-Up2: 1
Other Rooms
- Laundry: Main Floor
Exterior
- Porch/Patio/Deck: Patio(s), Porch(es)
Parking
- Garage: Yes
- Garage Spaces: 2
- Total Spaces: 2
- Parking Type: Off Street, Detached Garage
- Garage Description: Garage Door Opener, Garage - Side Entry
Location
- Municipality: Chestertown
- County: KENT
- Driving Directions: Cross Chester River bridge, left on Spring St., right on High St. property on left. Sign posted
- Historic District: Yes
- City Limits: Yes
School Information
- School District: Kent County Public Schools
- High School: Kent County
Heating & Cooling
- Cooling Type: Ductless/Mini-Split
- Cooling Fuel: Electric
- Heating Type: Forced Air, Heat Pump(s), Hot Water, Radiator, Wall Unit
- Heating Fuel: Electric
- Water Heater: Bottled Gas, Tankless
Utilities
- Sewer: Public Sewer
- Water: Public
Structural Information
- Architectural Style: Victorian
- Structure Type: Detached
- Construction: Frame
- Basement: Yes
- Basement Entrance: Yes
- Basement Desc.: Outside Entrance, Connecting Stairway, Sump Pump, Other, Partial, Unfinished
- Foundation: Slab
- Roof: Metal, Asphalt
- Walls/Ceilings: Beamed Ceilings, Dry Wall, Plaster Walls, Tray Ceilin
- Windows: Casement, Vinyl Clad, Double Pane, Insulated, Skylights, Storm, Wood Frame
- Doors: Sliding Glass
- Stories Description: Main, Upper 1, Upper 2
- Square Feet: 3,047
- Sq. Ft. Source: Assessor
- Living Area: 3,047 Sq. Ft.
- Finished Above Grnd: 3,047 Sq. Ft.
- Year Built: 1780
- Year Built Source: Estimated
- Property Condition: Excellent
Additional Structures
- Other Structures: Garage(s)
Lot Features
- Lot Size (Acres): 0.14
- Lot Size (Sq. Ft.): 6,286
- Lot Size Source: Assessor
- Zoning: R-5
- Lot Description: Landscaping
- Fencing (Description): Partially, Rear
Financial Considerations
- Price Per Sq. Ft.: $271.74
- Assessment Year: 2026
- City/TownTax: $2,979
- City/TownTax Freq: Annually
- County Tax: $7,801
- County Tax Freq: Annually
- Tax w/Assessment: $705,567
- Tax Amount: $10,781
- Tax Year: 2025
- Tax Total Finished Sq. Ft.: 3047
Disclosures and Reports
- Ownership: Fee Simple
- Lot Number: 6
Listed by Coldwell Banker Chesapeake Real Estate Company, Lisa P Raffetto
We Value Your Privacy
We Value Your Privacy
We Value Your Privacy
Listing agent
— 407 High St —
Lisa P Raffetto
Coldwell Banker Chesapeake Real Estate Company
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 407 High St
School District:Kent County Public Schools
| Name | Grades | Distance |
|---|---|---|
H. H. Garnett Elementary School 320 Calvert Street, Chestertown, MD 21620 | PK-5 | 0.2 mi |
Kent County Middle School 402 East Campus Avenue, Chestertown, MD 21620 | 6-8 | 0.6 mi |
Kent County High School 25301 Lambs Meadow Road, Worton, MD 21678 | 9-12 | 5.3 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 407 High St
Tax History
Tax History for 407 High St
Year
Property Taxes
Change
Tax Assessment
Change
2025
$10,593
5%
$687,900
5%
2024
$10,086
11%
$652,967
6%
2023
$9,080
—
$618,033
6%
2022
$9,080
1%
$583,100
1%
2020
$8,989
—
$578,333
1%
2021
$8,989
1%
$573,567
1%
2020
$8,896
1%
$568,800
—
2019
$8,839
3%
$568,800
—
2018
$8,555
—
$568,800
—
2017
$8,555
306%
$568,800
—
2016
$2,105
-75%
$568,800
—
2015
$8,555
98%
$568,800
-1%
2014
$4,310
—
$573,200
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 407 High St
This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
- Single Family
- Active
- Updated 10 days ago
- 3Beds
- 4Total Baths
- 2,472Sq. Ft.
- Single Family
- Active
- Updated 5 days ago
- 4Beds
- 4Total Baths
- 4,489Sq. Ft.
This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
- Single Family
- Active
- Updated 5 days ago
- 2Beds
- 1Total Bath
- 726Sq. Ft.
- Single Family
- Active
- Updated 5 days ago
- 4Beds
- 2Total Baths
- 1,192Sq. Ft.
- Single Family
- Active
- Updated 16 hours ago
- 3Beds
- 2Total Baths
- 1,680Sq. Ft.
This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
- Single Family
- Active
- Updated 4 days ago
- 3Beds
- 3Total Baths
- 1,484Sq. Ft.
- Single Family
- Active
- Updated 5 days ago
- 3Beds
- 2Total Baths
- 1,233Sq. Ft.
This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
407 High Street, Chestertown, MD 21620 (MLS# MDKE2006496) is a Single Family property with 3 bedrooms, 3 full bathrooms and 1 partial bathroom. 407 High Street is currently listed for $828,000 and was received on May 07, 2026. Want to learn more about 407 High Street? Do you have questions about finding other Single Family real estate for sale in Chestertown? You can browse all Chestertown real estate or contact a Coldwell Banker agent to request more information.