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Lynsey Bennett
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22005 Main Street, Hillsboro, MD 21641

$525,000
  • 22005 Main Street, Hillsboro, MD 21641 Main Photo

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Price Reduced $20,000 on February 24th, 2026
BEDS3 BATHS3 full SQUARE FEET3,088 MLS#MDCM2005446
STATUSACTIVE PROPERTY TYPEResidential - Single Family SCHOOLCAROLINE COUNTY PUBLIC SCHOOLS

Property Description

PLEASE NOTE that the Owner has listened to the current market, Price has been reduced to $525,000. It is a property of beautifully preserved quality on ¾ of an acre in an urban setting. Most unusual! When compared to equivalent historic properties it is now very competitively priced! 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. Public landing with dock and kayak lauch is just a block away. 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).

22005 Main Street | MLS# MDCM2005446

This single family home located at 22005 Main Street, Hillsboro, MD 21641 is currently listed for sale with an asking price of $525,000. This property was built in 1794 and has 3 bedrooms and 3 full baths with 3088 sq. ft. Main Street is located within the CAROLINE COUNTY PUBLIC SCHOOLS school district. Search Hillsboro real estate on www.lynseybennettrealtor.com today.

Property Features

Property Type: Residential - Single Family
Basement: Unfinished, Outside Entrance, Interior Access, Partial, Connecting Stairway
Basement: Yes
Cooling: Central A/C, Window Unit(s)
Fireplaces: 4
Fuel Type: Oil
Heating: Radiator
Home Style: Colonial
Lot Size: 0.66 Acres
Roof Type: Asphalt
Stories: 4.0
Taxes: $4,786
Year Built: 1794

Feature Descriptions

Additional Structures: Above Grade, Below Grade
Appliances: Dishwasher, Water Heater
Building Name: NONE AVAILABLE
Exterior: Brick
Exterior: Outbuilding(s), Sidewalks
Fireplace: Brick, Gas/Propane, Mantel(s)
Flooring: Wood
Lot: Corner, Level, Rear Yard, SideYard(s), Trees/Wooded
Lot Dimensions: 0.66 Acre(S)
Municipality: Hillsboro
Parking Features: Gravel Driveway
Parking Notes: 2 Total Parking Spaces
Rooms: Living Room, Dining Room, Primary Bedroom, Bedroom 2,Bedroom 3,Kitchen, Family Room, Basement, Foyer, Bathroom 2,Attic, Primary Bathroom
Sewer: On Site Septic
Special View Info: Garden/Lawn, Street, Trees/Woods
SQFT Above Finished: 3088
SQFT Total Finished: 3088
Structure Type: Detached
Total Garage/Parking Spaces: 2
Utilities: Cable TV, Propane
Water: Well
Windows: Double Hung, Transom, Wood Frame
Wooded: Yes

Room Sizes

Primary Bedroom: 20 x 16 Level - Upper 1
Primary Bathroom: 9 x 9 Level - Upper 1
Bedroom 2: 9 x 15 Level - Upper 1
Bedroom 3: 10 x 19 Level - Upper 1
Living Room: 20 x 19 Level - Main
Dining Room: 19 x 16 Level - Main
Kitchen: 17 x 15 Level - Main
Family Room: 20 x 16 Level - Main
Foyer: 20 x 10 Level - Main

Local Schools

School District: CAROLINE COUNTY PUBLIC SCHOOLS

Listed By / Shown By

Listed By

Agency Name: Maryland Heritage Properties
Agency Phone: 4107789319

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Estimated Payment

$ 1,720.38 per month $1,168.42 Principal & Interest $398.83 Property Tax $153.13 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 03/18/2026. The listing information on this page last changed on 03/18/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Wed 03/18/2026 12:01:02 AM EST) or Bright MLS (last updated Tue 03/17/2026 11:50:02 PM EST). Real estate listings held by brokerage firms other than Berkshire Hathaway HomeServices Homesale Realty may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
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Lynsey Bennett 

16 Greenmeadow Drive, Suite 300, Timonium, MD 21093
410-561-0044

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