Step into timeless charm and modern comfort with this beautifully renovated historic home in the heart of downtown Marianna. Nestled along a picturesque street lined with majestic live oaks, this stunning 4-bedroom, 3-bath residence blends classic character with thoughtful updates throughout. Inside, you'll find a gorgeous custom kitchen designed to impress, featuring quartz countertops, stainless steel appliances, unique built-in features, a striking tin feature ceiling, and a movable island that provides flexible workspace for cooking and entertaining. The spacious primary suite offers two cedar closets with a dedicated dressing area and a beautifully renovated en-suite bathroom complete with a tiled walk-in shower and double shower heads for a spa-like experience. Outdoor living is just as inviting. Imagine starting your mornings with coffee on the large front porch while enjoying the peaceful canopy of historic live oaks overhead. The partially fenced backyard offers a private retreat with a sparkling in-ground swimming pool, screened porch area, and pool deck with string lights overhead--creating the perfect setting for evening swims,or weekend gatherings. Adding incredible versatility, the property also includes a charming carriage house with its own full kitchen, laundry, living room, and 1 bedroom and 1 bathroom--ideal for guests, extended family, or potential rental income. The carriage house features a welcoming covered front porch and an attached open deck, perfect for enjoying a quiet afternoon, grilling with friends, or unwinding while overlooking the beautifully landscaped grounds. Additional highlights include a detached workshop, a covered pergola area, beautiful landscaping, a Rinnai tankless water heater, and a roof updated in 2018. This rare downtown gem offers historic charm, modern amenities, and flexible living spaces all in one exceptional property.