South Side Pennsylvania homes for sale starting at Fifty Thousand Dollars

$299,900 - South Side, PA

1711 Larkins Way South Side, PA - This is a four-bedroom, two-full-bath stand-alone home in the amazing South Side Flats walk-to-everything neighborhood. It has updated bathrooms, kitchen, and hard surface floors. It has been freshly painted and features a brand new furnace, central a/c, and water heater. It is move-in ready, and comes with a one-year home warranty.

$298,900 - South Side, PA

28 Gregory Street South Side, PA - Perched in the heart of the South Side Slopes, this spacious charmer is bursting with personality and potential! Enjoy breathtaking panoramic views of Downtown Pittsburgh, the South Side, and Oakland from the main living space, front porch, and bedrooms. The open-concept living and dining areas are perfect for game nights or cozy evenings in, while two private decks, one off the kitchen and another from a second-floor bedroom, offer the perfect spots for morning coffee or sunset unwinding. With four large bedrooms (plus a bonus room that could be a fifth!), this home has space to spare. Each level has its own thermostat, keeping everyone comfy. Parking in front and behind home! Just a mile from Giant Eagle, ALDI, SS Works, LA Fitness, a dog park, and plenty of great restaurants, this location is everything! Plus, you're just minutes from the stadiums, hospitals, and all the excitement of Downtown Pittsburgh. Don’t miss out on this one-of-a-kind city retreat!

$287,000 - South Side, PA

2611 Jane Street South Side, PA - South Side Flats Special! Plenty of potential here – three generous bedrooms and three full baths (one en-suite!), one on each floor, span nearly 1,700 sqft of character-filled living space, where modern updates meet timeless charm both inside and out. Well maintained throughout, bathed in natural light, LVP flooring, updated eat-in kitchen, side covered patio connecting to enclosed no-maintenance courtyard, balcony, and a quiet street. Three levels of flexible living space, abundant basement storage, and minimal upkeep make this an ideal Airbnb hotspot, house-hack opportunity, long-term rental or a smart choice for student housing – already staged and ready! Easy addition to any investor portfolio ready to generate income from day one. Prime location for steady demand – close to downtown and local colleges, all excitement on Carson Street and access to parks and bike trails. Enjoy a flat walk to grocery store, gym, offices, shops, and dining at SouthSide Works. Home Warranty Included!

$285,000 - South Side, PA

2412 Burham St South Side, PA - Jaw-dropping views at 2412 Burham St. This 3 bedroom, 2.5 bathroom home sits on the Southside slopes with a professional garden that greets you in the front. Upgrades from top to bottom. Kitchen is a chef's dream with a large island that has a gas top, double ovens, beautiful cabinetry and counters. Plenty of space for entertaining or a day of baking. The views from the living room are spectacular day or night. On the second floor are two bedrooms and a full bath. One bedroom features a balcony to enjoy the views and the second bedroom has access to the backyard. The home is steps from a lovely community park. Nicely located for a quick trip to any of the communities outside of the City, and minutes to Downtown. Plus, walkable to restaurants, coffee shops and more.

$284,900 - South Side, PA

2818 Edwards Way South Side, PA - Located in Pittsburgh’s historic South Side, this beautifully updated home offers the perfect mix of charm and convenience. Featuring ALL new siding, a brand NEW roof & gutters, this home is move-in ready. The open-concept living space flows seamlessly into the modern kitchen, ideal for entertaining. Enjoy ample closet space, a stylishly updated bathroom, and a spacious bedroom with plenty of natural light. Step outside to a backyard retreat and enjoy the ease of off-street parking. Just steps from South Side Works, this home is also minutes from downtown, universities, and Mercy Hospital. Don't miss this rare find in one of Pittsburgh’s most vibrant neighborhoods!

$277,000 - South Side, PA

2110 Larkins Way South Side, PA - This up-and-down duplex is a fantastic investment in a prime location near local universities, offering great rental potential. The first-floor unit is a cozy one-bedroom, one bath, currently rented out and providing immediate income. Upstairs, the two-bedroom, one bath is available for rent, perfect for attracting students and professionals. Both units feature fully equipped kitchens and are move-in ready. With separate entrances this property ensures privacy and convenience for tenants. Don't miss this chance to own an income-generating property in a high-demand area!

$239,900 - South Side, PA

15 Enon Way South Side, PA - Move in ready newly remodeled single family home located in the heart of the South Side flats. As you enter you will notice tons of natural light on the main level with the first bedroom and an updated bathroom. Upstairs you will find the new kitchen with white cabinetry, granite countertops, and stainless appliances. There are also the two additional bedrooms and the second updated bathroom. There is a laundry area on the second floor. This home features a new roof, siding, flooring, lighting, new furnace and new AC. Walking distance to shops, restaurants, bars, and more.

$229,900 - South Side, PA

2633 S 18Th St South Side, PA - Charming City Duplex – Ideal Location with Private Laundry in Each Unit This well-maintained duplex offers two distinct units in the heart of the city, perfect for owner-occupants or savvy investors. The front unit features 2 spacious bedrooms, 1 full bathroom, and an additional partial bath for extra convenience. The rear unit is a cozy 1 bedroom, 1 bathroom layout—ideal for a tenant, guest suite, or rental income. Both units are equipped with their own in-unit washer and dryer, adding value and convenience. Located directly on the bus line, commuting is a breeze, and you're just steps from local shops, restaurants, and city life. Don't miss this opportunity to own a versatile property in a prime urban location!

$229,900 - South Side, PA

2633 S 18Th St South Side, PA - Charming City Duplex – Ideal Location with Private Laundry in Each Unit. This well-maintained duplex offers two distinct units in the heart of the city, perfect for owner-occupants or savvy investors. The front unit features 2 spacious bedrooms, 1 full bathroom, and an additional partial bath for extra convenience. The rear unit is a cozy 1 bedroom, 1 bathroom layout—ideal for a tenant, guest suite, or rental income. Both units are equipped with their own in-unit washer and dryer, adding value and convenience. Located directly on the bus line, commuting is a breeze, and you're just steps from local shops, restaurants, and city life. Don't miss this opportunity to own a versatile property in a prime urban location!

$225,000 - South Side, PA

99 S 10Th St South Side, PA - Opportunity to own a well-maintained brick building on busy S 10th St near PJ McCardle, offering excellent visibility and easy access. Currently in use as an animal rescue, the first floor features a spacious front room, rear workspace, updated lighting, and a newer powder room. The second floor offers two rooms and a full bath with tub/shower. Outside, there’s a private back porch and a small fenced courtyard. Major updates include a new roof in 2021 and a furnace in 2024. Potential for office, mixed-use, etc.

South Side, Pennsylvania listings for sale

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