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$1,165,000
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Property Description
From within and without, from the front, the sides and the back, this exceptional 1876 and 1998 residence sings. Every passer-by has stopped and gazed upon the wrap around porch. No doubt, many a conversation "over the railing" has taken place for decades. Those fortunate enough to have enjoyed hospitality inside this German-wood clad home have experienced both its expansive flow of inter-connected rooms with center hall, the cozy grandness of an era long ago and comfortable living today amidst an eclectic mix of modern art and furniture, antiques, and other treasures. Prominent historic downtown location. Significant land parcel. 5 bedrooms, office, 6 public rooms on first floor, 4 and 1 half baths. Beautiful side and rear garden, with pond, brick paths, and exceptional specimens. Former garage converted to studio with full bath. Come visit Charleston or Savanah in Chestertown.
Full Property Details
Full Property Details for 119 High St
General
- Sold For: $1,165,000
- Taxes: $7,664 (2024)
- Status: Closed
- Type: Single Family
- Source: BrightMLSMidAtlantic
- MLS ID: MDKE2005728
- Added to Site: 102 day(s) ago
Interior
- Rooms/Areas: Living Room, Dining Room, Primary Bedroom, Sitting Room, Bedroom 2, Bedroom 3, Bedroom 4, Bedroom 5, Kitchen, Family Room, Breakfast Room, Sun/Florida Room, Laundry, Office, Utility Room, Workshop, Bathroom 2, Bathroom 3, Primary Bathroom, Half Bath
- Interior Features: Bathroom - Jetted Tub, Bathroom - Stall Shower, Breakfast Area, Built-Ins, Ceiling Fan(s), Chair Railings, Crown Moldings, Family Room Off Kitchen, Floor Plan - Traditional, Formal/Separate Dining Room, Kitchen - Gourmet, Primary Bath(s), Skylight(s), Wainscotting, Walk-in Closet(s), Window Treatments, Wood Floors
- Fireplace: Yes
- Number of Fireplaces: 3
- Fireplace(s): Gas/Propane, Wood
- Appliances: Built-In Microwave, Built-In Range, Dishwasher, Disposal, Dryer, ENERGY STAR Dishwasher, Exhaust Fan, Extra Refrigerator/Freezer, Icemaker, Range Hood, Refrigerator, Stainless Steel Appliances, Washer, Water Heater
- Flooring: Partially Carpeted, Hardwood
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: 5
- Bedrooms Upper: 5
- Bedrooms-Up2: 2
Other Rooms
- Laundry: Basement, Upper Floor
Additional Information
- Security/Safety: Carbon Monoxide Detector(s), Security System, Smoke Detector
Exterior
- Exterior Features: Gutter System
- Porch/Patio/Deck: Balconies- Multiple, Porch(es), Patio(s), Wrap Around
Parking
- Garage: Yes
- Garage Spaces: 1
- Total Spaces: 5
- Parking Features: Gravel Driveway
- Parking Type: Detached Garage, Driveway, Off Street
- Garage Description: Other
Location
- Municipality: Chestertown
- County: KENT
- Subdivision: HISTORIC DISTRICT CHESTERTOWN
- Driving Directions: High Street between Queen and Water Street, in downtown Chestertown
- City Limits: Yes
School Information
- School District: Kent County Public Schools
Community
- Pets Allowed: Yes
- Pets: No Pet Restrictions
Heating & Cooling
- Central air: Yes
- Cooling Type: Central A/C
- Cooling Fuel: Electric
- Heating Type: Baseboard - Hot Water
- Heating Fuel: Oil, Propane - Owned
- Water Heater: Electric
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: Propane, Electric Available
Structural Information
- Architectural Style: Traditional, Georgian
- Structure Type: Detached
- Builder: R.K. Pippen
- Construction: Wood Siding
- Basement: Yes
- Basement Entrance: Yes
- Basement Desc.: Partially Finished, Poured Concrete, Shelving, Side Entrance, Space For Rooms, Workshop
- Foundation: Stone, Block
- Roof: Metal, Shake, Architectural Shingle
- Walls/Ceilings: High, Plaster Walls, Dry Wall
- Windows: Bay/Bow, Wood Frame
- Doors: French, Storm
- Entry Floor Number: 1
- Stories Description: Lower 1, Main, Upper 1, Upper 2
- Square Feet: 5,345
- Sq. Ft. Source: Estimated
- Living Area: 4,409 Sq. Ft.
- Finished Above Grnd: 4,409 Sq. Ft.
- Year Built: 1876
- Year Built Source: Estimated
- Property Condition: Excellent
Additional Structures
- Other Structures: Office/Studio, Shed
Lot Features
- Property View: Garden/Lawn, Street
- Lot Size (Acres): 0.25
- Lot Size (Sq. Ft.): 10,977
- Lot Size Source: Assessor
- Zoning: R-3
- Lot Description: Rear Yard, SideYard(s), Landscaping
- Fencing (Description): Wrought Iron, Wood, Privacy
Financial Considerations
- Price Per Sq. Ft.: $283.51
- Assessment Year: 2025
- City/TownTax: $2,118
- City/TownTax Freq: Annually
- County Tax: $5,545
- County Tax Freq: Annually
- Tax w/Assessment: $509,100
- Tax Amount: $7,664
- Tax Year: 2024
- Terms: Standard Sale
- Tax Total Finished Sq. Ft.: 3247
Disclosures and Reports
- Ownership: Fee Simple
Listed by Cross Street Realtors LLC, Richard Keaveney
Sold by Cross Street Realtors LLC, Casey Scattergood
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Schools
Schools serving 119 High St
School District:Kent County Public Schools
| Name | Grades | Distance |
|---|---|---|
Kent County Middle School 402 East Campus Avenue, Chestertown, MD 21620 | 6-8 | 0.7 mi |
Kent County High School 25301 Lambs Meadow Road, Worton, MD 21678 | 9-12 | 5.5 mi |
Disclaimer:
School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 119 High St
Date
Details
Price
Change
Source
12/01/2025
Sold
$1,165,000
-6.8%
MLS
10/05/2025
Listed
$1,250,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
119 High Street, Chestertown, MD 21620 (MLS# MDKE2005728) is a Single Family property that was sold at $1,165,000 on December 01, 2025. Want to learn more about 119 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.

