Welcome to 142 Longfellow Street, nestled in the quiet leafy streets of Portland's Deering Highlands, one of the city's most sought-after neighborhoods. This home has not been offered for sale in more than two decades. Tastefully renovated while retaining its classic Craftsman charm, it boasts updated systems including a new state-of-the-art boiler and water heater, Andersen architecturally authentic windows throughout, and a no-maintenance gutter system. Its large city lot with spacious back yard offers privacy and mature landscaping with a shady brick patio and private sunny deck off the kitchen. Heavy oak cabinets, granite countertops, newer appliances, and an adjacent sunroom make its eat-in kitchen the heart of the home, perfect for large family gatherings. Its front-to-back living/dining area features a cozy window seat and French doors. You'll find three bedrooms upstairs along with a private office space. When company stays, a comfy den on the first floor with an ensuite bath doubles as a guest room. This home also features a spacious and practical tiled mudroom/pantry and a finished walk-out ground-floor bonus room with full-sized windows and a fireplace (wood-stove insert) for use as a family room or office.