22005 Main St

Hillsboro, MD 21641

$545,000
Price
3
Beds
3,088 Sq. Ft.
$176 / Sq. Ft.
3,088
Sq. Ft.
$176
per Sq. Ft.
front view of a house
a front view of a house with a yard
Rear of house showing wings.
a view of a yard with some trees
Winter rear entrance to grand Center Hall.
Summer.
a living room with wooden floor and furniture
a view of a hallway with wooden floor and staircase
a view of entryway
Gracious Stairway
a view of a small space
a living room with furniture and a fireplace
a living room with furniture a rug and a book shelf
a living room with furniture a flat screen tv and a dining table
a living room with furniture a rug and a bookshelf
a view of a workspace with furniture and a book shelf
a living room with a couch and a table
Dining Room
a view of a dining room with furniture
a living room with furniture a chandelier and a fireplace
Door to Kitchen Wing
a view of a park with large trees
Master of all he surveys.
Peaceful Gardens
Kitchen
a kitchen with kitchen island granite countertop a sink appliances cabinets and a counter top space
a kitchen with stainless steel appliances granite countertop a sink a stove and a wooden floors
a kitchen with stainless steel appliances granite countertop a stove a sink dishwasher and cabinets with wooden floor
a kitchen with stainless steel appliances granite countertop a stove a sink and a refrigerator
a kitchen with stainless steel appliances granite countertop a stove and a cabinets
a kitchen with stainless steel appliances granite countertop a stove and a refrigerator
a view of kitchen and hall with wooden floor
a view of entryway
a living room with lots of furniture and wooden floors
a living room with furniture and a window
a bedroom with a bed and walk in closet
a bathroom with a sink and a mirror
Hall Bath
Primary Bedroom
a living room with furniture and a fireplace
a view of a workspace with furniture
a bedroom with a bed and a fireplace
a bedroom with a bed and a window
Entering back stair hall
Back Stair Hall & Stairs
Transitional Hall in Primary Bedroom wing.
a view of a entryway door with wooden floor
a front view of a house with a yard
Gathering Room Wing added later..
Gathering Room Wing added later..
a view of a swimming pool with an outdoor kitchen
a view of a house with a tree
a view of a yard in front of a house with large trees
a front view of a house with a garden
a room with gym equipment
a living room with a couch and a stove top oven
a living room with furniture a flat screen tv and a window
a table with a vase and flowers on it
Outbuildiing interior.
Outbuildiing interior.
a front view of a house with a yard
a view of a white house next to a road with large trees
a view of a brick house with many windows
front view of a building with a street
a view of house with outdoor space and swimming pool
a front view of a house with a yard
a view of a wooden door of a house
a view of entryway

Description

This fine, brick dwelling originating from the18th c. is situated in Hillsboro on Maryland's peaceful Eastern Shore. Hillsboro, nestled along the Tuckahoe River, conveniently located to all that is important to the Eastern Shore's sought-after lifestyle. The WILLIAM SMITH HOUSE, built in 1794, exemplifies the world of a successful Grain Merchant living in an important hub for grain and tobacco. The house has been altered slightly through the many decades, but the character of the original building...This fine, brick dwelling originating from the18th c. is situated in Hillsboro on Maryland's peaceful Eastern Shore. Hillsboro, nestled along the Tuckahoe River, conveniently located to all that is important to the Eastern Shore's sought-after lifestyle. The WILLIAM SMITH HOUSE, built in 1794, exemplifies the world of a successful Grain Merchant living in an important hub for grain and tobacco. The house has been altered slightly through the many decades, but the character of the original building dominates the architecture and "feel" of its 1794 era. Its charm and elegance remain. The rooms are commodious and inviting. The grand center ENTRANCE HALL is punctuated by the graceful stair, fine woodwork and doors. The LIVING ROOM, as expected, is spacious and comfortable with fireplace (now gas fired), original floors, and bookshelves. The DINING ROOM, of a grand size, features a fireplace (now gas), cabinetry and glass front cupboards. Two steps down from the dining Room the fully equipped KITCHEN is found with wood floor, exposed rafters and back stairway. Open from the kitchen is the GATHERING ROOM with wood floor and wide views of the grounds and gardens. A paver path from this room leads to the driveway and parking. An open DECK offers a secluded retreat off the kitchen wing

BEDROOMS and BATHS are found on second floor. Two of which have fireplaces although decorative at this time. Access to the bedroom level is either from the main grand stairway or via the back stairs. Adding to the charm is the back stair hall in the primary bedroom wing located over the kitchen and "gathering" room. The baths are delightful. A surprise outbuilding is to the rear of the grounds. A perfect spot for an office, studio or storage. Another smaller outbuilding offers more storage. The grounds feature tall mature trees and fencing. The William Smith House is all one would expect built in a gracious era with a colorful history. Where is hillsboro?? Hillsboro lies a short distance from both Denton, Caroline County and Easton in Talbot County. Chestertown, in Kent County, is just 40 minutes. Annapolis, the Capitol of Maryland, is less than an hour. Unique shops, sailing facilities, live theater and restaurants abound. Hillsboro is from 1- 2 hours from the "rest of the world" for BWI, National and Philadelphia airports are a swift drive away. Dulles a bit further. A private airport is found in Easton. - 15 minutes. Atlantic Ocean resorts are about an hour. Adkins Arboretum is 1.5 miles. Adkins is a 400-acre native garden and preserve, provides exceptional experiences in nature to promote environmental stewardship. The Hillsboro Public Landing on the Tuckahoe is just a block from property. This property and lifestyle is an enriching experience” It awaits its next steward(s).
  1. Listed by Nancy McD McGuire • Maryland Heritage Properties
    P: (443)-480-7342 nmcguire@mdheritage.properties

Property Details for 22005 Main Street

Tax ID Number
0606005098
Ownership
Fee Simple
Condo Coop Association
No
HOA
No
Structure Type
Detached
Style
Colonial
Levels/Stories
4
Furnished
No
LISTING UPDATED: 12/08/2025 07:49 PM

Property Details for 22005 Main Street

StatusActive
MLS #MDCM2005446
Days on Market341
Taxes$4,786 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Fee Simple
Year Built1794
Lot Size0.66 AC / 28,575 SF
CountyCaroline County

Location

Listing Courtesy of Maryland Heritage Properties
Add your commute

Building Information for 22005 Main Street

Stories4Year Built1794Building Size-Lot Size0.66 AC / 28,575 SF

Payment Calculator

$3,055 per month

30 year fixed, 6.15% Interest

Principal and Interest

$2,656

Property Taxes

$399

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 22005 Main Street

Location
Location
  • In City Limits: Yes
  • School District Name: CAROLINE COUNTY PUBLIC SCHOOLS
  • School District County ID: 121139029245
  • SchoolDistrictSource: 3rd Party
  • County: CAROLINE
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
  • Property Manager Y/N: No
  • Senior Community: No
  • Association Recreation Fee Y/N: No
Taxes and Assessment
Taxes and Assessment
  • Tax Year: 2024
  • Tax Assessed Value: $360,233
  • Year Assessed: 2024
  • County Tax: $3,934
  • Improvement Assessed Value: $329,600
  • City Town Tax: $792
  • Land Assessed Value: $52,600
  • Clean Green Assessed: No
  • Land Use Code: R
  • Section: 2
  • Agricultural Tax Due: No
  • Historic: Yes
  • Zoning: RESIDENTIAL
  • School Tax: $0
  • Automatically Update Tax Values Y/N: Yes
Lease Information
Lease Information
  • Pets Allowed: No
Rooms
Main
  • # Bedrooms Count Main Level: 0
  • # Bathrooms Count Main Level: 1
  • # Bathrooms Full Main Level: 1
All Upper Levels
  • # Bedrooms Count All Upper Levels: 3
  • # Bathrooms Count All Upper Levels: 2
  • # Bathrooms Full All Upper Levels: 2
Upper Level 1
  • # Bedrooms Count Upper Level: 3
  • # Bathrooms Count Upper Level: 2
  • # Bathrooms Full Upper Level: 2
Upper Level 2
  • # Bedrooms Count Upper Level: 0
  • # Bathrooms Count Upper Level: 0
  • # Bathrooms Full Upper Level: 0
All Lower Levels
  • # Bedrooms All Lower Levels: 0
  • # Bathrooms All Lower Levels: 0
  • # Bathrooms Full All Lower Levels: 0
Lower Level 1
  • # Bedrooms Lower Level: 0
  • # Bathrooms Lower Level: 0
  • # Bathrooms Full Lower Level: 0
Rooms
  • Room List: Living Room, Dining Room, Primary Bedroom, Bedroom 2, Bedroom 3, Kitchen, Family Room, Basement, Foyer, Bathroom 2, Attic, Primary Bathroom
  • Stories: Lower 1, Main, Upper 1, Upper 2
Rooms Information
Room 1
  • Room Type: Attic
  • Room Level: Upper 2
  • Room Exists: Yes
Room 2
  • Room Type: Primary Bedroom
  • Room Length: 20.0
  • Room Width: 16.0
  • Room Level: Upper 1
  • Room Exists: Yes
  • Room Features: Fireplace - Other, Flooring - Wood
Room 3
  • Room Type: Primary Bathroom
  • Room Length: 9.0
  • Room Width: 9.0
  • Room Level: Upper 1
  • Room Exists: Yes
  • Room Features: Flooring - Wood
Room 4
  • Room Type: Bedroom 2
  • Room Length: 9.0
  • Room Width: 15.0
  • Room Level: Upper 1
  • Room Exists: Yes
  • Room Features: Flooring - Wood
Room 5
  • Room Type: Bedroom 3
  • Room Length: 10.0
  • Room Width: 19.0
  • Room Level: Upper 1
  • Room Exists: Yes
  • Room Features: Fireplace - Other, Flooring - Wood
Room 6
  • Room Type: Living Room
  • Room Length: 20.0
  • Room Width: 19.0
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Flooring - Wood, Fireplace - Gas, Built-Ins, Lighting - Recessed
Room 7
  • Room Type: Dining Room
  • Room Length: 19.0
  • Room Width: 16.0
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Flooring - Wood, Fireplace - Gas, Built-Ins
Room 8
  • Room Type: Bathroom 2
  • Room Level: Upper 1
  • Room Exists: Yes
Room 9
  • Room Type: Kitchen
  • Room Length: 17.0
  • Room Width: 15.0
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Flooring - Wood
Room 10
  • Room Type: Family Room
  • Room Length: 20.0
  • Room Width: 16.0
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Flooring - Wood
Room 11
  • Room Type: Basement
  • Room Level: Lower 1
  • Room Exists: Yes
Room 12
  • Room Type: Foyer
  • Room Length: 20.0
  • Room Width: 10.0
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Flooring - Wood
Building Info
Building Info
  • Builder Name: William Smith in c. 1794
  • Total Finished SQFT: 3,088.00
  • Total Finished SQFT Source: Assessor
  • Tax Total Finished SQFT: 3,088.00
  • Total SQFT: 4,240.00
  • Total SQFT Source: Assessor
  • Construction Materials: Brick
  • Roof: Asphalt
  • Ext Main Mid-res: http://bright-media02.prd.brightmls.com/bright/images/0000/8037/0869/7780/803708697780_512_384_WM_Qxg6oLH5P8UWnYti.jpg
  • Wall and Ceiling Types: 9'+ Ceilings
  • Flooring Type: Wood
  • Basement Type: Unfinished, Outside Entrance, Interior Access, Partial, Connecting Stairway
  • Foundation Details: Brick/Mortar
  • Room and Floor: Bathrooms Full-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: 3
  • Other Structure: Above Grade, Below Grade
Lot / Land Information
Lot / Land Information
  • Lot Size Source: Assessor
  • Lot Features: Corner, Level, Rear Yard, SideYard(s), Trees/Wooded
  • Parcel ID: 4494832
  • Ground Rent Exists: No
Parking
Parking
  • Type Of Parking: Driveway, Off Street, On Street
  • Driveway - # of Spaces: 1
  • Off Street - # of Spaces: 1
  • Parking Features: Gravel Driveway
Interior Features
Interior Features
  • Fireplace: Yes
  • Fireplaces Count: 4
  • Fireplace Features: Brick, Gas/Propane, Mantel(s)
  • Appliances: Dishwasher, Water Heater
  • Accessibility Features: None
  • Door Features: Six Panel, French
  • Window Features: Double Hung, Transom, Wood Frame
  • Laundry Type: Has Laundry, Main Floor, Washer In Unit, Dryer In Unit
Exterior Features
Exterior Features
  • Exterior Features: Outbuilding(s), Sidewalks
  • Pool: No Pool
Utilities
Utilities
  • Utilities: Cable TV, Propane
  • Heating: Yes
  • Cooling Type: Central A/C, Window Unit(s)
  • Cooling Fuel: Electric
  • Heating Type: Radiator
  • Heating Fuel: Oil
  • Hot Water: Electric
  • Water Source: Well
  • Sewer Septic: On Site Septic
Confidential Data
Listing Office
  • List Agent AOR: Bay Area Association of REALTORS
  • List Agent URL: www. marylandheritageproperties.com

Property History for 22005 Main Street

DateEvent & SourcePriceAppreciation
Mar 19, 2025

Listed (Active)

BRIGHT #MDCM2005446

$545,000—
Apr 1, 2009

Closed (Public Record)

Public Record #267016214

$330,000

+13.7% / yr

Apr 1, 2009

Closed

BRIGHT #MDCM100658

$330,000—
Feb 20, 2009

Pending

BRIGHT #MDCM100658

—
Sep 28, 2007

Listed (Active)

BRIGHT #MDCM100658

$445,000—
Nov 30, 2006

Withdrawn

BRIGHT #MDCM121264

$495,000—
Nov 30, 2006

Withdrawn

BRIGHT #MDCM121264

—
Feb 24, 2006

Listed (Active)

BRIGHT #MDCM121264

$525,000—
Nov 19, 2003

Closed

BRIGHT #MDCM105434

$165,000—
Nov 12, 2003

Closed (Public Record)

Public Record #135261334

$165,000—
Aug 19, 2003

Pending

BRIGHT #MDCM105434

—
Jul 9, 2003

Listed (Active)

BRIGHT #MDCM105434

$199,000—
DateEvent & SourcePrice
03/19/2025

Listed (Active)

BRIGHT #MDCM2005446

$545,000
04/01/2009

Closed (Public Record)

Public Record #267016214

$330,000

+13.7% / yr

04/01/2009

Closed

BRIGHT #MDCM100658

$330,000
02/20/2009

Pending

BRIGHT #MDCM100658

—
09/28/2007

Listed (Active)

BRIGHT #MDCM100658

$445,000
11/30/2006

Withdrawn

BRIGHT #MDCM121264

$495,000
11/30/2006

Withdrawn

BRIGHT #MDCM121264

—
02/24/2006

Listed (Active)

BRIGHT #MDCM121264

$525,000
11/19/2003

Closed

BRIGHT #MDCM105434

$165,000
11/12/2003

Closed (Public Record)

Public Record #135261334

$165,000
08/19/2003

Pending

BRIGHT #MDCM105434

—
07/09/2003

Listed (Active)

BRIGHT #MDCM105434

$199,000

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

Public Records for 22005 Main Street

Taxable ValueLand$52,600Additions$329,600Total$382,200
Tax Record2023$4,364 ($364 / month)
Home Facts
Beds0Baths2.5Total Finished SqFt3,088 SqFtAbove Grade Finished SqFt3,088 SqFtStories2Lot Size28,575 SqFtStyleSingle Family ResidenceYear Built1794CountyCAROLINEAPN06-005098Fireplace TypeHas Fireplace

Schools near 22005 Main Street

This home is within Caroline County Public Schools.
Rating
School
Type
Grades
Distance
Ridgely Elementary School
Public - PK to 5
Lockerman Middle School
Public - 6 to 8
North Caroline High School
Public - 9 to 12
Rating
School
Distance
Ridgely Elementary School
PublicPK to 5

Lockerman Middle School
Public6 to 8

North Caroline High School
Public9 to 12

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 22005 Main Street, Hillsboro, MD 21641

22005 Main Street is a single family home for sale in Hillsboro, MD 21641. This property was listed for sale on March 19, 2025 by Maryland Heritage Properties, it's currently listed at $545,000. It has been on the market for a total of 341 days and was last sold on April 1, 2009. This listing's school district is Caroline County Public Schools. Nearby schools include Ridgely Elementary School, Lockerman Middle School and North Caroline High School. 22005 Main Street is a 3-bed, 3-bath, 3,088 sqft single family home built in 1794.

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 Maryland Heritage Properties

© 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 12/08/2025 07:49 PM