This one has it all. A historic home less than half a mile from the Woodstock Square, Woodstock High School, and Dean St Elementary that blends character, space, and a long list of thoughtful updates. Major improvements are already done, with the roof, furnace, central air, water heater, dryer, refrigerator, and carpet all less than three years old. The first floor bedroom features a private bath with a zero step shower, offering the potential for multigenerational living. Upstairs, the primary bedroom has its own attached bath and a separate laundry room. Inside, there's room for everyone to spread out, with a massive living room featuring hardwood floors and a wood burning fireplace, plus a separate family room for even more living space. Outside the freshly painted exterior opens to multiple outdoor living spaces, including a covered front porch and a back deck spanning more than 800 square feet. Plenty of room to entertain, relax, and enjoy this incredible location. A truly unique home on one of Woodstock's most iconic streets, just minutes from schools and everything the Square has to offer.