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22005 MAIN ST, HILLSBORO, MD 21641

3 Beds

3 Baths

3,088SqFt

Active

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).

Property Details
Price $525,000
Bedrooms 3
Full Baths 3
Total Baths 3
Property Style Colonial
Lot Size Area Units Square Feet
Acres 0.66
Property Type Residential
Sub type SingleFamilyResidence
MLS Sub type Detached
Stories 4
Exterior Features Outbuilding(s),Sidewalks
Year Built 1794
Fireplaces 4
Subdivision NONE AVAILABLE
View Garden/Lawn,Street,Trees/Woods
Roof Asphalt
Heating Radiator
Foundation Brick/Mortar
Accessibility None
Lot Description Corner,Level,Rear Yard,SideYard(s),Trees/Wooded
Parking Description Gravel Driveway
Geographic Data
Directions From Ches. Bay Bridge travel East. Take R onto Rt 50 S toward Easton 1.5 miles L on to MD 404E miles; Take Old Queen Anne Rd exit 315 ft.; Continue onto MD 404 ALT E/Old Queen Anne Rd; Turn left onto MD 303 (MD 404 ALT aka E. Main Street; Brick 18th c. property on corner of Main and Maple.
County CAROLINE
Latitude 38.91684267
Longitude -75.94206513
Address Information
Address 22005 MAIN ST, HILLSBORO, MD 21641
Postal Code 21641
City HILLSBORO
Cross Street Maple
State MD
Country United States
Listing Information
Listing Office Maryland Heritage Properties
Listing Office Email nmcguire@mdheritage.properties
Listing Agent Nancy McGuire
Special listing conditions Standard
Ownership Fee Simple
Terms Cash,Conventional
School Information
District CAROLINE COUNTY PUBLIC SCHOOLS
MLS Information
Days on market 504
MLS Status Active
Listing Date Mar 19, 2025
Listing Last Modified Aug 4, 2026
Tax ID 0606005098
Tax Year 2024
Tax Annual Amount 4786
MLS # MDCM2005446

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Last updated: 2026-08-04T23:30:25.201313Z. Listing information is provided by Bright MLS. Listings are generated from various brokers who participate in IDX. Information is deemed reliable but not guaranteed.