Welcome to a truly rare opportunity in the heart of Dover-Foxcroft -- a stunning and remarkably flexible antique property at 8 Monument Square that blends historic charm, incredible square footage, and endless possibilities for living, working, or investing. Whether you're searching for the ideal owner-occupied property, an impressive work-from-home setup, professional office space, or a unique multi-unit conversion opportunity, this exceptional building delivers. The upstairs owner's quarters are nothing short of spectacular, offering a dramatic two-story living space filled with character and natural light. Vaulted ceilings, spacious bedrooms, beautiful architectural details, and sun-drenched windows create an atmosphere that feels both grand and welcoming. Private entrances, a fenced-in yard, patio area, and peaceful outdoor spaces provide privacy rarely found in an in-town property. Downstairs, the former dental office opens the door to countless possibilities. Already equipped with multiple offices/exam rooms, lab or potential kitchen space, two full bathrooms, and two half baths, the layout is ideally suited for a medical provider, wellness business, professional offices, creative studio space, or conversion into additional residential units. With the addition of another kitchen area, the property could easily support multiple apartments or a live/work configuration. Throughout the home, you'll find gorgeous period details, multiple fireplaces, inviting porches, and the timeless character only a historic property can offer. Outside, enjoy river views, ample parking, and one of the most convenient locations in town -- just a short walk to shops, restaurants, schools, parks, and everything downtown Dover-Foxcroft has to offer.