119 High St
Chestertown, MD 21620

$1,165,000

Last Sold Price

Beds

Baths

4,409 Sq. Ft.

$264 / Sq. Ft.

4,409

Sq. Ft.

$264

per Sq. Ft.

Closed 12/1/25

Brick & Gravel Driveway to Studio & Gardens

Exceptional Rear & Side Gardens with Fencing

Sunroom Adjoins Living Room & Breakfast Room

Breakfast Room adjoins Sunroom & Family Room

Kitchen, Butler Pass-thru to Dining Room

Family Room w/ Fireplace, Powder Room & Back Porch

Primary Bedroom w/ Ensuite Bath & Walk-in Closet

Second Floor Porch Adjoins Primary Suite

Third Floor Plan w/ 2 Bedrooms, Office & Hall Bath

Basement Floor Plan Mechanicals & Workshop (1998)

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...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.

Listed by Richard Keaveney • Cross Street Realtors LLC
P: (410)-708-6470 rdkeaveney@gmail.com

Property Details for 119 High Street

Tax ID Number

1504017188

Ownership

Fee Simple

Condo Coop Association

HOA

Entry Floor Number

Structure Type

Detached

Style

Traditional, Georgian

Levels/Stories

LISTING UPDATED: 12/01/2025 07:56 PM

Property Details for 119 High Street

Status	Closed
MLS #	MDKE2005728
Days on Market	6
Taxes	$7,664 / year
HOA Fees	-
Condo/Co-op Fees	-
Compass Type	Single Family
MLS Type	Residential / Fee Simple
Year Built	1876
Lot Size	0.25 AC / 10,977 SF
County	Kent County

Location

Listing Courtesy of Cross Street Realtors LLC

Sold By Cross Street Realtors LLC

Add your commute

Building Information for 119 High Street

Stories3Year Built1876Building Size-Lot Size0.25 AC / 10,977 SF

Payment Calculator

$6,317 per month

30 year fixed, 6.15% Interest

Principal and Interest

$5,678

Property Taxes

$639

HOA Dues

The Payment Calculator is for illustrative purposes only.

Property Information for 119 High Street

Location

In City Limits: Yes
School District Name: KENT COUNTY PUBLIC SCHOOLS

School District County ID: 121139164602
SchoolDistrictSource: Listing Agent
County: KENT

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

Senior Community: No
Association Recreation Fee Y/N: No

Taxes and Assessment

Tax Year: 2024
Tax Assessed Value: $509,100

Year Assessed: 2025
County Tax: $5,545
Improvement Assessed Value: $250,200
City Town Tax: $2,118
Land Assessed Value: $258,900
Clean Green Assessed: No
Land Use Code: R
Loss Mitigation Fee: No
Zoning: R-3
School Tax: $0
Automatically Update Tax Values Y/N: Yes

Lease Information

Pets Allowed: Yes
Pet Restrictions: No Pet Restrictions

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: 5
# Bathrooms Count All Upper Levels: 4

# Bathrooms Full All Upper Levels: 4
# Bathrooms Half All Upper Levels: 0

Upper Level 1

# Bedrooms Count Upper Level: 3
# Bathrooms Count Upper Level: 3

# Bathrooms Full Upper Level: 3
# Bathrooms Half Upper Level: 0

Upper Level 2

# Bedrooms Count Upper Level: 2
# Bathrooms Count Upper Level: 1

# Bathrooms Full Upper Level: 1
# Bathrooms Half Upper Level: 0

All Lower Levels

# Bedrooms All Lower Levels: 0
# Bathrooms All Lower Levels: 0

# Bathrooms Full All Lower Levels: 0
# Bathrooms Half All Lower Levels: 0

Lower Level 1

# Bedrooms Lower Level: 0
# Bathrooms Lower Level: 0

# Bathrooms Full Lower Level: 0
# Bathrooms Half Lower Level: 0

Rooms

Room List: 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
Stories: Lower 1, Main, Upper 1, Upper 2

Rooms Information

Room 1

Room Type: Living Room
Room Level: Main

Room Exists: Yes

Room 2

Room Type: Dining Room
Room Level: Main

Room Exists: Yes

Room 3

Room Type: Breakfast Room
Room Level: Main

Room Exists: Yes

Room 4

Room Type: Kitchen
Room Level: Main

Room Exists: Yes

Room 5

Room Type: Sun/Florida Room
Room Level: Main

Room Exists: Yes

Room 6

Room Type: Family Room
Room Level: Main

Room Exists: Yes

Room 7

Room Type: Half Bath
Room Level: Main

Room Exists: Yes

Room 8

Room Type: Primary Bedroom
Room Level: Upper 1

Room Exists: Yes

Room 9

Room Type: Primary Bathroom
Room Level: Upper 1

Room Exists: Yes

Room 10

Room Type: Sitting Room
Room Level: Upper 1

Room Exists: Yes

Room 11

Room Type: Bedroom 2
Room Level: Upper 1

Room Exists: Yes

Room 12

Room Type: Bedroom 3
Room Level: Upper 1

Room Exists: Yes

Room 13

Room Type: Bathroom 2
Room Level: Upper 1

Room Exists: Yes

Room 14

Room Type: Laundry
Room Level: Upper 1

Room Exists: Yes

Room 15

Room Type: Bedroom 4
Room Level: Upper 2

Room Exists: Yes

Room 16

Room Type: Bedroom 5
Room Level: Upper 2

Room Exists: Yes

Room 17

Room Type: Bathroom 3
Room Level: Upper 2

Room Exists: Yes

Room 18

Room Type: Utility Room
Room Level: Lower 1

Room Exists: Yes

Room 19

Room Type: Laundry
Room Level: Lower 1

Room Exists: Yes

Room 20

Room Type: Workshop
Room Level: Lower 1

Room Exists: Yes

Room 21

Room Type: Office
Room Level: Upper 2

Room Exists: Yes

Room 22

Room Type: Bathroom 3
Room Level: Upper 1

Room Exists: Yes

Building Info

Builder Name: R.K. Pippen
Year Major Reno Remodel: 1997

Total Finished SQFT: 4,409.00
Total Finished SQFT Source: Estimated
Tax Total Finished SQFT: 3,247.00
Total SQFT: 5,345.00
Total SQFT Source: Estimated
Construction Materials: Wood Siding
Roof: Metal, Shake, Architectural Shingle
Ext Main Mid-res: http://bright-media02.prd.brightmls.com/bright/images/0000/8042/0234/7932/804202347932_512_384_WM_UoBYt99r-31pihib.jpg
Wall and Ceiling Types: High, Plaster Walls, Dry Wall
Flooring Type: Partially Carpeted, Hardwood
Basement Type: Partially Finished, Poured Concrete, Shelving, Side Entrance, Space For Rooms, Workshop
Basement Footprint Percent: 90.00
Foundation Details: Stone, Block
Room and Floor: Bathrooms Half-Main Level-1, Bedrooms-Upper Level 1-1, Bedrooms-Upper Level 1-2, Bedrooms-Upper Level 1-3, Bathrooms Full-Upper Level 1-1, Bathrooms Full-Upper Level 1-2, Bathrooms Full-Upper Level 1-3, Bedrooms-Upper Level 2-1, Bedrooms-Upper Level 2-2, Bathrooms Full-Upper Level 2-1
# Bathrooms Full: 4
# Bathrooms Half: 1
Other Structure: Office/Studio, Shed

Lot / Land Information

Lot Size Source: Assessor
Lot Features: Rear Yard, SideYard(s), Landscaping

Fencing: Wrought Iron, Wood, Privacy
Parcel ID: 4505415
Ground Rent Exists: No

Parking

Type Of Parking: Detached Garage, Driveway, Off Street
Num of Detached Garage Spaces: 1

Driveway - # of Spaces: 4
Total Garage Spaces: 1
Parking Features: Gravel Driveway
Garage Features: Other

Interior Features

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

Fireplaces Count: 3
Fireplace Features: 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
Accessibility Features: None
Security Features: Carbon Monoxide Detector(s), Security System, Smoke Detector
Door Features: French, Storm
Window Features: Bay/Bow, Wood Frame
Laundry Type: Basement, Upper Floor

Exterior Features

Spa: No
Exterior Features: Gutter System

Outdoor Living Structures: Balconies- Multiple, Porch(es), Patio(s), Wrap Around
Pool: No Pool
Horse: No

Utilities

Utilities: Propane, Electric Available
Heating: Yes

Cooling Type: Central A/C
Cooling Fuel: Electric
Heating Type: Baseboard - Hot Water
Heating Fuel: Oil, Propane - Owned
Hot Water: Electric
Water Source: Public
Sewer Septic: Public Sewer
Internet Services: Fiber Optic

Confidential Data

Listing Office

List Agent AOR: Mid-Shore Board of REALTORS

Property History for 119 High Street

Date	Event & Source	Price	Appreciation
Dec 1, 2025	Closed (Public Record) Public Record #1922569128	$1,165,000	—
Dec 1, 2025	Closed BRIGHT #MDKE2005728	$1,165,000	—
Oct 10, 2025	Pending BRIGHT #MDKE2005728		—
Oct 10, 2025	Active Under Contract BRIGHT #MDKE2005728		—
Oct 5, 2025	Listed (Active) BRIGHT #MDKE2005728	$1,250,000	—

Date	Event & Source	Price
12/01/2025	Closed (Public Record) Public Record #1922569128	$1,165,000
12/01/2025	Closed BRIGHT #MDKE2005728	$1,165,000
10/10/2025	Pending BRIGHT #MDKE2005728	—
10/10/2025	Active Under Contract BRIGHT #MDKE2005728	—
10/05/2025	Listed (Active) BRIGHT #MDKE2005728	$1,250,000

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

Public Records for 119 High Street

Taxable ValueLand$258,900Additions$250,200Total$509,100

Tax Record2025$7,979 ($665 / month)

Home Facts

Beds0Baths5.5Total Finished SqFt3,247 SqFtAbove Grade Finished SqFt3,247 SqFtStories3Lot Size10,977 SqFtStyleSingle Family ResidenceYear Built1900ZoningR-3CountyKENTAPN04-017188Fireplace TypeHas Fireplace

Schools near 119 High Street

This home is within Kent County Public Schools.


Rating	School	Type	Grades	Distance
7/10	H. H. Garnett Elementary School	Public - Nearby school	PK to 5	0.5 mi
2/10	Kent County Middle School	Public - Serves this home	6 to 8	0.7 mi
5/10	Kent County High School	Public - Serves this home	9 to 12	5.5 mi
NR	Worton Elementary School	Public - Nearby school	PK to 5	5.4 mi
5/10	Rock Hall Elementary School	Public - Nearby school	PK to 5	10.5 mi
NR	Millington Elementary School	Public - Nearby school	PK to 5	12.8 mi
NR	Chester River Adventist School	Private - Nearby school	1 to 8	0.4 mi
NR	Chestertown Christian Academy	Private - Nearby school	PK to 12	1.1 mi
NR	Radcliffe Creek School	Private - Nearby school	K to 8	1.3 mi


Rating	School	Distance
7/10	H. H. Garnett Elementary School PublicPK to 5 Nearby school	0.5 mi
2/10	Kent County Middle School Public6 to 8 Serves this home	0.7 mi
5/10	Kent County High School Public9 to 12 Serves this home	5.5 mi
NR	Worton Elementary School PublicPK to 5 Nearby school	5.4 mi
5/10	Rock Hall Elementary School PublicPK to 5 Nearby school	10.5 mi
NR	Millington Elementary School PublicPK to 5 Nearby school	12.8 mi
NR	Chester River Adventist School Private1 to 8 Nearby school	0.4 mi
NR	Chestertown Christian Academy PrivatePK to 12 Nearby school	1.1 mi
NR	Radcliffe Creek School PrivateK to 8 Nearby school	1.3 mi

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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Listing Courtesy of Cross Street Realtors LLC

© 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 12/01/2025 07:56 PM

119 High StChestertown, MD 21620

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119 High St
Chestertown, MD 21620