Charming historic home with bonus guest cottage, located on the most beautiful oak lined street in picturesque Monticello, Florida. OWNER FINANCING AVAILABLE call for convenient terms. Enjoy small town living in this updated home featuring a 2020 Roof, 2022 HVAC, 2025 Water Heater, Updated Electrical, CPVC and Copper Plumbing, Schedule 40 sewer piping, and mostly updated windows. New mini split ac in owners suite, new ac duct work, carpet, and landscaping. Relax on the inviting wrap around porches or sundeck, perfect for enjoying peaceful mornings and evenings. Inside, the home offers formal living and dining rooms, a spacious owner's suite with en suite bath and dual walk in closets and beautiful hard wood floors. A galley kitchen with SS appliances, large pantry and sunny breakfast room with guest bath. Spacious laundry room with W/D 2nd refrigerator and ample storage. Upstairs, you'll find a second master suite with an updated bath and walk in closet. Also 2 additional bedrooms and full bath. Situated on a generous .91 acre lot with 2 Homes and two fenced areas, ideal for pets or even a chicken coop! The separate guest cottage, built in 1987, features a full kitchen, bath, living room, washer/dryer, carport, and separate utility meter perfect for rental income or multi generational living. Walk to charming local restaurants, antique shops, and live performances at the Monticello Opera House, or enjoy nearby outdoor adventures and historic attractions. Main Home is 4 bedroom 3 1/2 Baths and the guest cottage is 718 Square feet not included in listing square footage total.