300 S Trenton Ave, Pittsburgh, PA 15221

Few investment properties offer this level of character, flexibility, and existing revenue potential. Located just steps from Regent Square and Wilkinsburg's growing collection of restaurants, coffee shops, and neighborhood amenities, 300 S. Trenton Avenue is a beautifully restored three-unit property where thoughtful design and historic craftsmanship have been transformed into a truly distinctive income-producing asset. The striking brick exterior immediately captures attention with its steep gables, original architectural details, and artfully crafted metal fire escapes that showcase the care and creativity invested in the property's restoration. Inside, each residence offers its own unique personality while sharing a common theme of thoughtfully designed living spaces filled with natural light, character, and warmth. Refinished hardwood floors, exposed brick accents, oversized windows, custom built-ins, exposed ductwork, reclaimed materials, and carefully curated finishes create an aesthetic rarely found in traditional investment properties. Dedicated work-from-home spaces, loft-inspired layouts, and abundant natural light make each residence feel more like a boutique urban loft than a conventional rental. The property features two spacious 1-bedroom, 1-bath apartments along with a beautifully designed studio apartment currently operating as a successful short-term rental. The Airbnb unit has generated $19,959.77 in income during 2025 alone, providing an attractive supplemental revenue stream and demonstrating the property's strong income-producing potential. The dramatic third-floor residence is particularly memorable, featuring soaring vaulted ceilings, exposed brick, corrugated metal architectural details, and an open-concept layout that creates a truly one-of-a-kind living experience. Beyond the interiors, residents enjoy private outdoor spaces, mature landscaping, and a surprisingly large, flat rear yard rarely found in this walkable urban setting. The corner lot location enhances natural light throughout the building while providing easy access to nearby shopping, dining, parks, public transportation, and the vibrant amenities of both Wilkinsburg and Regent Square. Whether you're seeking a fully leased investment, an owner-occupied opportunity with supplemental rental income, or a distinctive multifamily property with proven short-term rental performance, 300 S. Trenton Avenue delivers a compelling combination of historic character, creative design, flexibility, and income potential in one of Pittsburgh's most connected east-end neighborhoods.