Step inside this gated Neo-Classical Midtown estate featuring a 4 bedroom main residence, plus a rare investment opportunity with two income-producing rentals on-site. The main house welcomes you with soaring ceilings, 8 fireplaces, and plantation shutters. Enter through the back door into a cozy den, seamlessly flowing into the heart of the home which includes a grand formal dining room, an elegant living room with a gas fireplace, a striking foyer with a sweeping staircase, a full guest bath, and a hidden storage closet beneath the stairs. A beautifully appointed kitchen features granite countertops, ample storage, a walk-in pantry with built-in drawers, and an adjacent laundry room. Upstairs you’ll find the primary suite featuring two walk-in closets, a linen closet, and and 2 separate vanities. Two additional bedrooms share a well-appointed guest bath, while the fourth bedroom—offering access to the upstairs porch—can also serve as an inviting upstairs den or home office. Outdoor living is just as impressive, with a wraparound porch, a greenhouse, a potting shed, and ample parking. This historic gem boasts a detached carriage house with two fully equipped 1 bedroom 1 bath guest apartments, each with a strong short-term rental history. Adjacent to the carriage house, a separate structure contains a private home office and laundry space for the guest apartments. Enjoy relaxing walks to the neighborhood park and popular Midtown businesses including Publix Supermarket, Taco Mama, and Old Dutch Ice Cream. Roof replaced in 2019, upstairs HVAC 2024. Buyer to verify all information during due diligence.