Highland Park Homes under $400,000

Highland Park Homes under $400,000

Welcome to Highland Park, a charming neighborhood nestled in the heart of Allegheny County, Pennsylvania. Known for its picturesque streets lined with lush trees, historic architecture, and a strong sense of community, Highland Park is a hidden gem that offers the perfect blend of suburban tranquility and urban convenience.

This vibrant area is home to a diverse population and boasts a rich cultural heritage, making it an ideal place for families, young professionals, and retirees alike. Residents enjoy easy access to a plethora of amenities, including local shops, restaurants, and parks. One of the crown jewels of the neighborhood is the stunning Highland Park itself, featuring beautiful gardens, walking trails, and playgrounds, perfect for leisurely strolls or family outings.

For those looking to make Highland Park their home, you’ll be pleased to discover an array of charming properties available for under $400,000. From quaint bungalows to spacious family homes, there’s something for everyone in this affordable price range. These homes often feature classic details and modern updates, providing both character and comfort. With the current market trends, now is the perfect time to explore your options and find the home of your dreams in Highland Park.

Whether you’re drawn to the neighborhood’s rich history, its vibrant community spirit, or the beautiful homes that await, Highland Park is a place where you can truly feel at home. Come and discover why so many are choosing to call this delightful area their own!

Newest Highland Park Homes under $400,000

5421 Wellesley Ave, Highland Park
$400,000
2 Beds ⋅ 1 Baths
Looking for a smart way to make homeownership work harder for you? This beautifully renovated Highland Park duplex offers the opportunity to live in one unit while generating rental income from the other. With two updated 2-bedroom, 1-bath units, separate gas and electric utilities, individual HVAC systems with central air, and extensive recent improvements, much of the heavy lifting has already been done. Both units feature remodeled kitchens and baths, quartz countertops, stainless steel appliances, dishwashers, built-in microwaves, LVP flooring, fresh paint and approximately 90% replacement windows. A shared laundry area is located in the basement. Unit 1 offers a living room, kitchen, full bath and bedroom on the main level, with a second bedroom upstairs for added separation and flexibility. A private rear deck provides its own outdoor space. Unit 2 features two bedrooms plus a versatile bonus room that could serve as an office, exercise room, storage or flex space. Both units also have access to the shared backyard and patio with solar string lighting. Major improvements include a new roof (2024), two HVAC systems with central air (2024), hot water tanks (2019 & 2020), renovated kitchens and baths, new electrical panels for each unit plus a third panel for common areas, updated flooring and paint, exterior painting and shared basement laundry. Located in Highland Park with public transit less than two blocks away, 5421 Wellesley offers convenient access to Highland Park, the Pittsburgh Zoo & Aquarium and Bryant Street dining and shops. Bakery Square, East Liberty, Shadyside and Lawrenceville are nearby, along with Carnegie Mellon University, the University of Pittsburgh, UPMC Children’s Hospital, West Penn Hospital and UPMC Shadyside. Whether you're considering an owner-occupied duplex or adding a well-improved property to your investment portfolio, 5421 Wellesley offers flexibility, separate utilities and two renovated units in a convenient East End location.

5421 Wellesley Ave, Highland Park

Listing courtesy of RE/MAX SELECT REALTY.

1129 N Saint Clair Street, Highland Park
$350,000
This three-unit property in Pittsburgh’s Highland Park neighborhood offers a versatile mix of units. The first-floor unit includes two bedrooms, a full bath, a living room, and a kitchen, plus finished basement space with a second kitchen, powder room, ceramic tile floor game room/bedroom, a 90% efficient furnace, a gas hot water tank, and direct backyard access. The second-floor unit offers two bedrooms, a full bath, living room, and kitchen. The third-floor unit includes one bedroom, a full bath, living room, and kitchen, creating a flexible mix of unit sizes for an income-producing property. Separate entrances provide added privacy, with the first floor having its own entrance and the upper units accessed separately. Outside, enjoy a spacious backyard with a storage shed, plus a welcoming front porch finished with Nature Stone flooring. A newer roof adds another important update. Located close to the shops, dining, parks, and amenities that make Highland Park such a desirable Pittsburgh neighborhood, this property offers both location and income potential for an owner/occupant or investor looking to add a multi-unit property to their portfolio.

1129 N Saint Clair Street, Highland Park

Listing courtesy of RE/MAX HOME CENTER.

5421 Wellesley Ave, Highland Park
$400,000
Turnkey cash flowing Highland Park duplex in a prime East End location with major renovations already completed! The property offers two spacious 2-bedroom, 1-bath units with separate gas and electric utilities, individual hot water tanks, and separate HVAC systems with central air. Both units have completely gutted and remodeled with new kitchens and baths, quartz countertops, stainless steel appliances, dishwashers, built-in microwaves, LVP flooring, fresh paint, and approximately 90% replacement windows. A shared laundry area has also been added in the basement. Unit 1 offers a living room, kitchen, full bath and bedroom on the main level, with a second bedroom upstairs—providing added separation and flexibility. This unit also features its own private rear deck. Unit 2 offers two bedrooms plus a versatile bonus room ideal for an office, storage, exercise space or other uses. Outside, tenants have access to the shared backyard and patio with solar string lighting. Ample on-street parking is available with no residential parking permit currently required. Major improvements include a new roof (2024), two HVAC systems with central air (2024), two hot water tanks (2019 & 2020), approximately 90% replacement windows, renovated kitchens and baths, new electrical panels for each unit plus a third panel dedicated to common areas, updated flooring and paint throughout, exterior painting, shared basement laundry and a backyard patio. With public transit less than two blocks away, 5421 Wellesley offers convenient access to Highland Park, the Pittsburgh Zoo & Aquarium, and Bryant Street dining and shops. Bakery Square, East Liberty, Shadyside and Lawrenceville are nearby, along with Carnegie Mellon University, the University of Pittsburgh, UPMC Children's Hospital, West Penn Hospital and UPMC Shadyside. With extensive renovations already completed, separate utilities, individual HVAC systems and two updated units, 5421 Wellesley Ave offers an opportunity to add a well-improved property in a prime East End location to an investment portfolio.

5421 Wellesley Ave, Highland Park

Listing courtesy of RE/MAX SELECT REALTY.

943 N Negley Avenue Unit 4, Highland Park
$319,000
1 Beds ⋅ 1 Baths
Absolutely charming and truly one-of-a-kind, this delightful Highland Park Cottage Style Carriage Home offers the perfect blend of character, comfort, and low-maintenance living in one of Pittsburgh’s most beloved neighborhoods. Tucked into a highly desirable Highland Park setting, this former carriage house lives with a warm cottage feel and offers a rare opportunity for buyers seeking something unique, inviting, and easy to love. The main level features one bright, open living space that is ideal for today’s lifestyle, with room for both a comfortable living area and dining space. The open kitchen includes a new stainless-steel refrigerator, a microwave, and a disposal, and connects easily to the main gathering area, creating a smart and efficient layout. Tons of windows fill the home with natural light, giving the space an airy, cheerful feel throughout the day. The second level offers fresh new carpeting, a brand-new washer and dryer, and comfortable private living space. The entire interior has just been painted, and central air adds everyday comfort. The HOA includes water, sewage, and yard maintenance, making this a wonderful option for anyone looking for convenience without sacrificing personality or location. Highland Park is known for its tree-lined streets, architectural charm, neighborhood feel, and easy access to some of the East End’s favorite amenities. Enjoy being close to Highland Park, the Reservoir, walking trails, tennis courts, playgrounds, Bryant Street shops and restaurants, the Pittsburgh Zoo & Aquarium, Bakery Square, East Liberty, Shadyside, Lawrenceville, universities, hospitals, and Downtown Pittsburgh. Rarely does a home this special come along; a bright, cozy cottage-style residence with character, updates, central air, outdoor charm, and a location that captures everything buyers love about Highland Park.

943 N Negley Avenue Unit 4, Highland Park

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

817 Farragut Street, Highland Park
$169,900
2 Beds ⋅ 1 Baths
Opportunity awaits in the heart of Highland Park! This 3-story row house offers 2 bedrooms, 1 full bathroom, and a finished attic that can serve as a third bedroom, home office, or flexible living space. Filled with potential, this home is ready for your personal touches and vision. The fenced-in backyard provides outdoor space for relaxing or entertaining, while the 1-car garage offers the convenience of off-street parking. The basement includes a laundry area and ample storage space. A newer roof was installed in 2022. Ideally located just minutes from Highland Park and approximately a 15-minute walk to Bryant Street's popular coffee shops, restaurants, and boutiques. Convenient access to public transportation, Bakery Square, Bloomfield, Shadyside, Oakland, Lawrenceville, the North Side, and Downtown Pittsburgh makes commuting and enjoying city amenities a breeze. A fantastic opportunity in one of Pittsburgh's most sought-after neighborhoods!

817 Farragut Street, Highland Park

Listing courtesy of RE/MAX SELECT REALTY.

848 Heberton St, Highland Park
$275,000
4 Beds ⋅ 2 Baths
Ideally situated in the heart of Highland Park, this quaint 3-bedroom, 1.5-bath row house welcomes you with an enchanting front porch where summer breezes filter through the shady awning. The welcoming main floor showcases high coffered ceilings, an original fireplace, and classic built-ins that enhance the bright living room and spacious dining room, creating an inviting atmosphere for both everyday living and entertaining. The updated kitchen in a neutral palette features contemporary appliances and access to a rear deck, perfect for enjoying morning coffee or dining outdoors. Upstairs, you'll find three comfortable bedrooms and a renovated full bath. The expansive third floor offers incredible flexibility and can serve as a home office, guest suite, media room, or fourth bedroom. The large dry basement boasts a laundry area, half bath, a framed out room that can be a game room, exercise room or playroom. Ample storage throughout the home ensures plenty of room for organization. A charming backyard provides the perfect setting for gardening or simply unwinding in your tranquil haven. Enjoy the beauty of being within walking distance of historic Highland Park neighborhood shops, popular restaurants, and the vibrant business corridor. Combining classic architectural details, valuable updates, and an exceptional location, this Highland Park gem offers the perfect blend of character, charm and comfort. Recent improvements provide added peace of mind, including a new boiler (2025) new hot water tank (2025), new electrical panel (2025), and a new sewer line (2025). Roof was replaced under 8 years ago.

848 Heberton St, Highland Park

Listing courtesy of RE/MAX SELECT REALTY.

5443 Wellesley Ave, Highland Park
$360,000
3 Beds ⋅ 2 Baths
Welcome to this inviting 3 bedroom, 1.5 bath home located in the beautiful Highland Park neighborhood. Recently painted walls and new carpeting have given the interior a fresh new look. This house offers a comfortable layout and contains updates throughout. On the main level, you will find a seamless, open flow between the living and dining areas. In addition, there is a bright sunroom which not only adds flexible space for relaxing but also invites the afternoon sun. The second floor has three reasonably sized bedrooms as well as the main bath. The lower level contains a dedicated office area with soundproofing which is ideal for remote work, creative projects, or a quiet retreat. The large, functional basement has plenty of room for storage as well as laundry access. Gardening or any outdoor activities can be enjoyed in the backyard, where you'll find a spacious deck. Located minutes from the Pittsburgh Zoo, Highland Park, and the shops and restaurants along Bryant Street this house is central to all the East End has to offer.

5443 Wellesley Ave, Highland Park

Listing courtesy of RE/MAX SELECT REALTY.

1303 Olivant St, Highland Park
$33,500
3 Beds ⋅ 2 Baths
Attention investors & rehabbers! Spacious 3BR / 1.5BA single-family home in Lincoln-Lemington-Belmar offering approx 1,384 sq ft & solid bones. Functional floor plan w/full basement, generous room sizes, & sizable lot. Property needs cosmetic & system updates—ideal value-add, fix-and-flip, or buy-and-hold rental opportunity. AS-IS sale. Convenient to public transit, neighborhood amenities, & a growing retail and dining corridor. Strong rental demand, cash-flow potential, and long-term upside.

1303 Olivant St, Highland Park

Listing courtesy of JANUS REALTY ADVISORS.

6333 Glenview Place, Highland Park
$375,000
4 Beds ⋅ 2 Baths
Character & Charm describe this row house located in such a key spot in the heart of Highland Park! Natural sunlight flows in through the windows making it bright and cheerful throughout. The interior has been freshly repainted with brand new carpet. The front porch invites you into a lovely living room with a decorative fireplace and a spacious dining room leading into a cozy kitchen. From the kitchen there is access to the back porch and shed. The 2nd floor has a large primary bedroom, full bathroom, and 2 additional bedrooms. The 3rd floor offers a 4th bedroom or option for an office/den. Walkable to Highland Park and the Zoo! Easy access to Universities, Medical Centers, Shopping, Restaurants, and everything Pittsburgh has to offer

6333 Glenview Place, Highland Park

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

904 N Saint Clair St, Highland Park
$265,000
3 Beds ⋅ 1 Baths
A charming 3 bedrooms row home in Highland Park. Partial renovated top to bottom. The renovated bathroom features walking shower and and beautiful Spanish tiles. The living room features beautiful engineering hardwood floor. The kitchen includes new cabinetry and quart countertop. A fence in back yard leads to the one car garage. Located in a walkable neighborhood, close to the Highland Park business district, parks, bus stops, and just minutes from hospitals, universities, shopping, and dining.

904 N Saint Clair St, Highland Park

Listing courtesy of HOMEZU.

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