407 High Street, Chestertown, MD 21620 - Photo 1

1/1

$725,000

Sold
Closed
Single Family
3 Beds
4 Full Baths
1 Partial Bath
3,047 Sq. Ft.
2 Car Garage

1/1

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. 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.

Full Property Details

Full Property Details for 407 High St

General

Sold For: $725,000
Taxes: $10,781 (2025)
Status: Closed
Type: Single Family
Source: BrightMLSMidAtlantic
MLS ID: MDKE2006496
Added to Site: 156 day(s) ago

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: 5
Full Bathrooms: 4
Half Bathrooms: 1
Upper 2 - Full Baths: 1
Upper Floor Baths: 4
Upper - Full Baths: 4
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.: $261.9
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
Terms: Standard Sale
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
Sold by Cross Street Realtors LLC, Richard Keaveney

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Listing agent

— 407 High St —

Lisa P Raffetto

Coldwell Banker Chesapeake Real Estate Company

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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

Date

Details

Price

Change

Source

9/08/2026

Sold

$725,000

-9.15%

MLS

6/03/2026

Price Reduced

$798,000

-3.62%

MLS

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.

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Total Bath
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Sq. Ft.

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Bed
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Total Bath
1,508
Sq. Ft.

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Single Family
Active
Updated 1 day ago

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Beds
3
Total Baths
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Sq. Ft.

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11729 St James Newtown Rd, Worton, MD 21678 - Photo 1

Price Reduced

-$30,000 (-51.72%)

$28,000

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Lots/Land
Active
Updated 2 days ago

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Acres

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Price Reduced

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Single Family
Active
Updated 3 days ago

3
Beds
1
Total Bath
1,008
Sq. Ft.

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Price Reduced

-$76,000 (-13.22%)

$499,000

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Single Family
Active
Updated 2 days ago

1
Bed
2
Total Baths
2,044
Sq. Ft.

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Price Reduced

-$63,000 (-6.64%)

$886,500

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Single Family
Active
Updated 3 days ago

5
Beds
3
Total Baths
3,696
Sq. Ft.

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Sold

$660,000

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Condo
Closed

3
Beds
2
Total Baths
1,600
Sq. Ft.

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$705,000

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Single Family
Closed

3
Beds
4
Total Baths
4,037
Sq. Ft.

Listed by Chesapeake Real Estate Associates, LLC, Erin Anderson
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$640,000

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Single Family
Closed

4
Beds
3
Total Baths
3,248
Sq. Ft.

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$825,000

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Single Family
Closed

4
Beds
4
Total Baths
5,290
Sq. Ft.

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Sold by Unrepresented, Unrepresented

407 High Street, Chestertown, MD 21620 (MLS# MDKE2006496) is a Single Family property that was sold at $725,000 on September 08, 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.

407 High St Chestertown, MD 21620