Own a remarkable piece of Greencastle history with the iconic Gilland Guest House, located at 101 E. Baltimore Street. Built around the turn of the 20th century by Dr. Gilland as both his medical practice and family residence, this stunning Victorian property offers a rare investment opportunity filled with quality craftsmanship and immediate, proven income potential. Unlike many converted homes, this property was originally designed to accommodate multiple living spaces and currently features four one-bedroom apartments, with the potential to create a fifth unit on the third level. Each apartment has been thoughtfully updated to preserve the building's historic charm while providing the modern conveniences today's tenants desire, including in-unit laundry facilities and off street parking. Timeless architectural details are found throughout, including beautifully preserved hardwood floors, intricate Victorian woodwork and moldings, reglazed tile, and original hand-crafted oak shutters that adorn every window. The attention to detail and quality of construction are a testament to a bygone era rarely found in today's properties. Situated in the heart of downtown Greencastle, this property offers strong rental appeal with walkable access to local shops, restaurants, and community amenities. Conveniently located less than two miles from Interstate 81, residents have easy commuting access north and south, with Frederick, MD and Carlisle, PA both approximately 44 miles away. Whether you're looking to expand your investment portfolio or own a truly distinctive historic property with reliable cash flow, the Gilland Guest House presents a rare opportunity to own one of Greencastle's most treasured landmarks.
Listing courtesy of Samson Properties. Contact: 7033788810

© 2026 TReND. All Rights Reserved.
The data relating to real estate for sale on this website appears in part through the TReND Internet Data Exchange (IDX) program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Real Estate Company participates, and is provided by TReND through a licensing agreement. Real estate listings held by brokerage firms other than Real Estate Company are marked with the IDX icon and detailed information about each listing includes the name of the listing broker.
All information provided is deemed reliable but is not guaranteed. Some properties which appear for sale on this website may no longer be available because they are under contract, have sold or are no longer being offered for sale. The information being provided is 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.