340 E Washington Street, Monticello, FL 32344 - Jefferson County

Step into the timeless elegance of the Simpkins-Bailey House, a distinguished circa 1854 residence nestled in the heart of Monticello's Historic District. This 3-bedroom, 3.5-bathroom home offers 3,635 square feet of meticulously updated living space, seamlessly blending historic charm with modern comforts. Zoned for business-residential use, the property provides incredible flexibility for a private residence, office, or mixed-use opportunity. The home features a brand-new 2024 metal roof and an encapsulated crawlspace with a dehumidifier for enhanced preservation. Inside, beautifully wide-plank hardwood floors stretch throughout, with a fireplace in every room adding to the historic character. The renovated kitchen and bathrooms seamlessly integrate modern style while honoring the home’s rich history, including a stunning clawfoot tub in the master bath. French doors lead from the living space to a screened-in back porch, offering a perfect place to relax. The fully fenced backyard features a picturesque boxwood garden, a charming pergola, and a magnificent live oak, creating a private oasis just steps from the vibrant downtown circle. With its stately presence, prime location, and thoughtful updates, this is a rare opportunity to own a beautifully preserved piece of Monticello’s history.

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