Built between 1890-1910, this Classic Revival home sits on 1.77 acres along one of Monticello’s most admired streets and offers timeless architecture with room to make it your own. The two-story layout includes 4 bedrooms and 3 bathrooms, with a circular driveway framed by boxwoods leading to a wide front porch perfect for rocking chairs. Inside, two front parlors flank the entry—one used as a living room and one with a closet allowing for modern use as a bedroom—and a traditional staircase leads upstairs to two bedrooms and a full bath. The large dining room has been opened to expose the original rafters, giving the space a bright and airy feel. Six original fireplaces provide historic character throughout the home. Period details including original hardwood floors, banisters, and molding showcase the craftsmanship of the era. Downstairs also includes a family room off the kitchen, a full guest bath, and a primary suite with an attached bath and nearby laundry. The upstairs landing opens to a secondary covered porch offering another peaceful spot to enjoy the quiet beauty of Pearl Street. The back portion of the property remains wooded, providing privacy or potential to expand with a guest house, pool, or garden. Just a short walk to downtown Monticello’s shops and restaurants, about 25 minutes to Thomasville, and roughly 30 minutes to Tallahassee. This home has over a century of stories, it's just waiting for its next tale to unfold!