The James Crockett House, circa 1822-1823. Steeped in history, filled with natural light and beautifully updated for modern living, 34-38 High Street is a remarkable reflection of Portland itself: rich in character, timeless in its appeal and brimming with possibility. Built before Portland became a city and standing long before the Great Fire of 1866, this distinguished Federal-style brick home offers an extraordinary connection to the city's past. The warmth of original pumpkin-pine floors, elegant fireplaces and mantels, tall windows with interior shutters, soaring ceilings, exquisite millwork and a graceful original staircase create an atmosphere that simply cannot be replicated. Every room tells a story. Yet this is a home to be lived in, not a museum to be admired. A beautiful new high-end kitchen, two updated bathrooms and thoughtful improvements bring modern comfort to nearly two centuries of architectural character. With 2,855 square feet, three bedrooms and exceptional natural light, the home is as inviting as it is impressive. Just beyond the Old Port, amid Portland's treasured Park, High and State Street corridors, the setting is wonderfully walkable and distinctly urban. And then there is the land: nearly a quarter acre in the heart of the city. Imagine gardens, an apple orchard, space to play or simply room to breathe. Add a detached garage, barn or ADU, or explore RN-4 zoning's potential for up to 14 total units, subject to approvals. Whether your vision is to preserve, expand or reimagine, the possibilities are extraordinary. A once-in-a-generation opportunity to own a truly irreplaceable piece of Portland.