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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
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.

$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.

$739,800
4 Beds 4 Baths
Welcome to Phase II of East Pittsburgh's newest residential home development- The Courtyards by Frick Park! 558 Mifflin Avenue is the 4th of 6 new construction homes to be built and the premier corner lot property of the plan with many options for customizations available. These beautiful standalone new construction single family homes custom designed by Wildman Chalmers feature a plethora of fantastic features both inside and out. Offering a wealth of curb appeal the exterior boasts front and rear porches, low maintenance fiber lap siding, Anderson series windows, an integral garage and one additional off street parking space. The interior living space of approximately 2,800 sqft spread over 3 levels features an open concept, FIVE ample sized bedrooms all with hardwood flooring, 3.5 bathrooms featuring glass shower enclosures and tile floors. Spacious kitchens will include brand new soft-close cabinets, granite/quartz counter-tops, and stainless steel appliances.Enjoy the close proximity of Frick Park, shopping amenities, public transportation, and 1 mile from the Parkway East to round out a perfect new home.

558 Mifflin Ave, Regent Square

Listing courtesy of RE/MAX SELECT REALTY.

$674,900
5 Beds 4 Baths
Welcome to Phase II of East Pittsburgh's newest residential home development- The Courtyards by Frick Park! 211 Green Street is the 3rd of 6 new construction homes to be built in the plan with many options for customizations available. These beautiful standalone new construction single family homes custom designed by Wildman Chalmers feature a plethora of fantastic features both inside and out. Offering a wealth of curb appeal the exterior boasts front and rear porches, low maintenance fiber lap siding, Anderson series windows, and 2 rear off-street parking spaces accessed by a private entrance. The interior living space of approximately 2,300sqft spread over 3 levels features an open concept, FIVE ample sized bedrooms all with hardwood flooring, 3.5 bathrooms featuring glass shower enclosures and tile floors. Spacious kitchens will include brand new soft-close cabinets, granite/quartz counter-tops, and stainless steel appliances.Enjoy the close proximity of Frick Park, shopping amenities, public transportation, and 1 mile from the Parkway East to round out a perfect new home.

211 Green St, Regent Square

Listing courtesy of RE/MAX SELECT REALTY.

$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.

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