Set on one of the most coveted streets in North of Montana's prestigious Gillette Regent Square, this Federal-style home is a rare gem on a nearly 9,000-square-foot lot. Coming to market for the first time in over 50 years, the offering boasts timeless charm on an idyllic, tree-lined street. Beyond the manicured front lawn, guests are welcomed into a home brimming with original character. The foyer is flanked by a formal living room with a fireplace, formal dining room, and kitchen with newer appliances and informal dining area. Also on the first level, a laundry room, bathroom with a shower, and cozy den with access to the sprawling backyard. Upstairs are all four bedrooms including the primary suite and hall bathroom with shower/tub. The primary suite includes multiple closets, vanity area, and an en-suite bathroom with shower. Additional features of the home include central heat and a California basement. The immensity of the lot is on full display in the backyard, which boasts a large pool, multiple lounge areas, and mature landscaping. A detached two-car garage completes the property and offers potential for conversion to an ADU (subject to city approval). This property presents an incredible opportunity to reimagine or fully develop the expansive lot into your dream North of Montana home. Enjoy close proximity to the Brentwood Country Mart, Montana Avenue boutiques and eateries, as well as top-rated schools, beaches, and more.