Welcome to 148 N Carlisle St, a prominent historic home in the heart of downtown Greencastle. Once the residence of Philip E. Baer, founder of Greencastle’s Old Home Week, and the longtime home of Henson’s Bakery for over 50 years, this property blends small-town legacy with versatile living potential. This classic brick colonial features 3 bedrooms, 1.5 bathrooms and retains much of its original charm, including real hardwood floors, two fireplaces and a 100+ year-old safe built right into the staircase. The home is serviced by natural gas radiant heat, 200 amp electric, public water and sewer, and includes recent upgrades like a new roof in 2024, updated boiler in 2018 and a new vinyl privacy fence running the length of the yard. Outside, enjoy a covered rear deck, storage shed and a side yard buffer for added space and privacy. Parking includes street parking out front plus 3 dedicated off-street spots accessible from the rear alley. But what truly sets this property apart is the 600+ sqft detached building — complete with its own separate electric and gas meters, hardwood floors, new siding and new roof. With some minor interior finishing (drywall and ceiling), this space could be transformed into a workshop, studio, office, man cave or flex space — or potentially even a rental unit or guest house, if hooked up to public water/sewer. This property is within walking distance of Greencastle's vibrant downtown, including local shops, restaurants, ice cream parlors, coffee shops, Jerome King Playground and community events! Whether you're looking to own a piece of Greencastle history, find a walkable in-town home with character, or invest in flexible income-producing space, this property checks all the boxes!