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$479,000
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.

300 S Trenton Ave, Wilkinsburg

Listing courtesy of COLDWELL BANKER REALTY.

$170,000
Welcome to 650 Ardmore Boulevard, Pittsburgh, PA, a charming duplex offering a perfect opportunity for owner-occupancy. Zoned for mixed use, keep it as a duplex or use the first floor for a commercial venture right on a main artery with Bricolage Productions and Community Forge right across the street. Easy access to i376. Each unit offers 2 bedrooms and one bath, with a third full bath in the basement. All utilities are separate, basement has two sump pumps and laundry. A small, fenced-in yard and a 2 car detached garage round out the property. The 2nd floor unit offers a private balcony to enjoy. With lots of natural light and great rental history, this duplex is ready to welcome its new owners and offers a fantastic opportunity for those looking to invest in a versatile property. Across the street is Community Forge and Bricolage Productions, inhabiting an old school building. Soon this space will have a coffee shop and theater!

650 Ardmore Blvd, Wilkinsburg

Listing courtesy of COMPASS PENNSYLVANIA, LLC.

$170,000
4 Beds 4 Baths
Welcome to 650 Ardmore Boulevard, Pittsburgh, PA, a charming duplex offering a perfect opportunity for owner-occupancy. Zoned for mixed use, keep it as a duplex or use the first floor for a commercial venture right on a main artery with Bricolage Productions and Community Forge right across the street. Easy access to i376. Each unit offers 2 bedrooms and one bath, with a third full bath in the basement. All utilities are separate except for water, basement has two sump pumps and laundry. A small, fenced-in yard and a 2 car detached garage round out the property. The 2nd floor unit offers a private balcony to enjoy. With lots of natural light and great rental history, this duplex is ready to welcome its new owners and offers a fantastic opportunity for those looking to invest in a versatile property. Community Forge inhabits an old school building across the street and soon this space will have a coffee shop and theater!

650 Ardmore Blvd, Wilkinsburg

Listing courtesy of COMPASS PENNSYLVANIA, LLC.

$170,000
Welcome to 650 Ardmore Boulevard, Pittsburgh, PA, a charming duplex offering a perfect opportunity for owner-occupancy. Zoned for mixed use, keep it as a duplex or use the first floor for a commercial venture right on a main artery with Bricolage Productions and Community Forge right across the street. Easy access to i376. Each unit offers 2 bedrooms and one bath, with a third full bath in the basement. All utilities are separate, basement has two sump pumps and laundry. A small, fenced-in yard and a 2 car detached garage round out the property. The 2nd floor unit offers a private balcony to enjoy. With lots of natural light and great rental history, this duplex is ready to welcome its new owners and offers a fantastic opportunity for those looking to invest in a versatile property. Community Forge inhabits an old school building across the street and soon this space will have a coffee shop and theater!

650 Ardmore Blvd, Wilkinsburg

Listing courtesy of COMPASS PENNSYLVANIA, LLC.

$697,750
REDEVELOPMENT OPPORTUNITY!! The former Wilkinsburg High School presents a prime redevelopment opportunity in historic Wilkinsburg—long considered the gateway between Downtown Pittsburgh and the Eastern Suburbs. Built to last, this architecturally distinct property is rich in charm and character, featuring high ceilings, abundant natural light, with original woodwork and flooring throughout. The building encompasses over 100,000 square feet across three floors, plus an additional 25,000-square-foot lower level. The main school includes wide corridors and approximately 40 spacious classrooms (±875 SF each) with dual access, along with multiple offices and restrooms. A large library/multipurpose room showcases original proscenium architectural detail, adding to the building’s historic appeal. The connected East Wing features a stunning, state-of-the-art 1,500-seat theater with balcony with direct street-level access. Above, the top floor houses a full-size gymnasium with mezzanine seating and locker rooms. The lower level offers additional amenities, including a cafeteria, dining area, woodshop, music room, and a second gymnasium. Centrally located just off Penn Avenue, the property offers strong walkability and convenient access to public transportation, including the Martin Luther King Jr. East Busway. It also provides excellent connectivity to Route 8, I-376 (Parkway East), and I-76 (PA Turnpike), making it an ideal location for commuters. With potential eligibility for tax incentives—such as Wilkinsburg’s LERTA tax abatement, Opportunity Zone designation, and Historic Tax Credits—the property presents exceptional adaptive reuse potential for a variety of uses, including multifamily, mixed-use, or institutional development. Take advantage of the area’s rich history and strong economic development support to bring new life to this iconic Wilkinsburg asset!!!

747 Wallace Ave (Wilkinsburg High School), Wilkinsburg

Listing courtesy of BERKSHIRE HATHAWAY HOMESERVICES THE PREFERRED PROP.

$89,900
4 Beds 1 Baths
Newly Vacant! Must See! Investor or First Time Buyer Special! Solid frame single family residence conveniently located in the heart of Wilkinsburg! Perfect for an investor looking for a great rental with appreciation potential or first time buyer! Amazing location! Updated a few years back and tenant had been in place ever since. Add some cosmetic upgrades and maximize rents or make this the home of your dreams! Main Floor: Entry, Living Room, Dining Room, and Kitchen. 2nd Floor: 3 Bedrooms and a Full Bath. 3rd Floor: Large Bedroom. Full basement for Laundry and Storage. 1 Car Integral Garage. Nice sized covered front porch and rear covered patio for your morning coffee. Decent sized rear yard for entertainment and cookouts! Could serve as a very nice rental grade home for a tenant, a fix and flip, or owner occupant looking to create the space of their dreams. With a vision, anything is possible here! This is a rare find, ideal for any investment portfolio!

1725 Laketon Rd, Wilkinsburg

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

$30,000
2 Beds 1 Baths
Townhouse located in Wilkinsburg offering approximately 1,000 square feet of living space with a traditional and functional layout. The main level features a living room, dining room, and kitchen, providing defined spaces suitable for everyday living and entertaining. The second level includes two nicely sized bedrooms and a full bathroom. The lower level offers a basement with generous storage space, adding flexibility for organization or additional use. Exterior features include a rear yard and a back porch, offering outdoor space for enjoyment or relaxation. The property provides a solid footprint and layout with the opportunity to enhance and personalize the home over time. Conveniently located near local amenities, public transportation, and surrounding neighborhoods.

1616 Montier St, Wilkinsburg

Listing courtesy of COLDWELL BANKER REALTY.

$349,900
Imagine the possibilities for the second century of this historic stone church! Restoration, renovation, and re-envisioning of 55,000 sq ft of unique opportunity into an ideal space for events, studios, offices, community center, or even condos or apartments. Main sanctuary is awe-inspiring with original stained glass windows, balconies, altar, and small chapel. The attached school’s 3 floors include classrooms, gym, kitchen, and a stunning children’s chapel with a curved, vaulted ceiling and arches. Established in 1905, the former Mulberry Presbyterian Church’s main sanctuary was built in 1911 with the school added in 1928. Portions of the main sanctuary roof were repaired in 2022 and a new roof installed on school in 2025. Multiple structural repairs were made to support the roof, interior beams, joists, and headers between first and second floors of the school. Property includes 3 lots comprising parking and green space. Come shape the next hundred years of this historic space!

710 Mulberry St, Wilkinsburg

Listing courtesy of RE/MAX REALTY BROKERS.

INFORMATION DEEMED RELIABLE, BUT NOT GUARANTEED. Listings courtesy of WEST PENN MULTILIST, INC.