West Penn MLS, Inc / Listed By: Lucy Wann, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Lucy Wann, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Ritu Vaidya, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Anthony Leone, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Imran Paniwala, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Georgie Smigel, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Sonia Gotera, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: James "Jim" Hiteshew, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Ritu Vaidya, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Georgie Smigel, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: James Battaglia, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Ryan Bibza, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Imran Paniwala, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Viktor Sizov, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Georgie Smigel, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Matthew "Matt" McKenna, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Georgie Smigel, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Anthony Leone, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Georgie Smigel, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Georgie Smigel, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Georgie Smigel, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Anthony Leone, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Ryan Bibza, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Georgie Smigel, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Anthony Leone, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Lucy Wann, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Georgie Smigel, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Anthony Leone, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Deborah "Deb" Walton, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Ryan Bibza, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Ryan Bibza, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Viktor Sizov, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Ryan Bibza, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Alishia Schultz, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Georgie Smigel, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Georgie Smigel, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Matthew "Matt" McKenna, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Georgie Smigel, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Georgie Smigel, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Samantha Campieri, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Valerie Keeley, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Georgie Smigel, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Rula Khoury, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Georgie Smigel, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Katina Hunter, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Samantha Campieri, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Ryan Bibza, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Deborah "Deb" Walton, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Patricia "Pat" Whigham, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Deborah "Deb" Walton, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Anthony Leone, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Matthew "Matt" McKenna, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Janet "Jan" Stevens, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Rula Khoury, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Sean Phillips, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Georgie Smigel, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Imran Paniwala, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Katina Hunter, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Janet "Jan" Stevens, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Georgie Smigel, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Chris Lange, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: James Battaglia, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Janet "Jan" Stevens, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Lisa Peters, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Anthony Leone, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Anthony Leone, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Melissa "Missy" Roberts, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Anthony Leone, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Anthony Leone, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Hannah O'Donoghue, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Jennifer Cosgrove, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Valerie Keeley, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Anthony Leone, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Georgie Smigel, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Rodney Lockwood, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Georgie Smigel, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Ryan Bibza, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Lisa Peters, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Ryan Bibza, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Tammy Romesburg, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Tammy Romesburg, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Katina Hunter, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Katina Hunter, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Georgie Smigel, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Anthony Leone, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Katina Hunter, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Georgie Smigel, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Katina Hunter, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Matthew "Matt" McKenna, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Anthony Leone, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Lucy Wann, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Deborah "Deb" Walton, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: James Battaglia, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Janet "Jan" Stevens, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Georgie Smigel, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Matthew "Matt" McKenna, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Sonia Gotera, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Ryan Bibza, Coldwell Banker Realty
West Penn MLS, Inc / Listed By: Sean Phillips, Coldwell Banker Realty
© 2022 Coldwell Banker Realty
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.