Nestled on one of downtown Plymouth's most picturesque tree-lined streets, this beautifully updated home blends timeless character, thoughtful modern updates, and an unbeatable walkable location. Spend your mornings with coffee or evenings with friends on the expansive covered front porch, enjoying the charm of one of Plymouth's most beloved neighborhoods, just a short stroll from Kellogg Park, restaurants, shops, and year-round community events. Inside, nearly every space has been thoughtfully refreshed while preserving the home's historic craftsmanship. Original hardwood floors, rich millwork, and vintage door hardware are complemented by fresh interior paint, designer lighting, and carefully curated finishes throughout. The inviting living room flows seamlessly into the dining room before opening to a spacious, updated kitchen featuring stainless steel appliances, generous prep space, and a dedicated coffee bar. A standout feature rarely found in homes of this era is the dedicated mudroom with its own private entrance, custom soft-close built-ins, and a hidden in-drawer power strip—adding both beauty and everyday functionality. The main level offers 1,260 square feet of well-designed living space, including three bedrooms and two full bathrooms, creating an exceptionally functional layout that makes everyday living convenient and accessible. The finished lower level, completed in 2022, brings the home to over 2,000 square feet of finished living space and adds 750 square feet designed for today's lifestyle. It features a cozy family room anchored by a built-in electric fireplace and large television, a dedicated fitness room, craft area, secondary office or flex workspace, and an updated laundry room—creating flexible space for work, hobbies, fitness, or family movie nights. Step outside to a private, fenced backyard with a spacious deck overlooking mature landscaping, along with a detached two-car garage and two additional storage sheds for exceptional storage. Extensive mechanical improvements provide exceptional peace of mind, including a new air conditioning system (2025), gutters and gutter guards (2024), hot water heater (2024), upgraded 200-amp electrical service with capacity for future EV charging (2023), updated washer and dryer, refreshed exterior paint, and significant updates to both the home's electrical and plumbing systems over the years. The home is also professionally plumbed for an exterior generator, which is included with the sale. Beautifully maintained, thoughtfully modernized, and filled with original charm, 465 Ann Street offers the best of both worlds: the character buyers love in a historic Plymouth home and the updates that make everyday living effortless. This is the kind of home that feels special the moment you arrive—and one you'll be proud to call home.