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$1,800,000
6 Beds ⋅ 4 Baths
Welcome to Wallingford Street — one of the most storied blocks in Pittsburgh’s historic Shadyside neighborhood, where timeless architecture & tree-lined boulevards frame a world of elegance, grace, & cultural charm. Amid this distinguished enclave stands 4749 Wallingford Street, a stately Tudor Revival masterpiece. Lovingly updated from the leaded glass windows to its grand sweeping staircase, to the refinished fireplaces, woodwork, new roof, and windows, every detail offers modern comfort and refined sophistication while preserving its historic soul. Generous rooms, warm light, and architectural integrity along with all new baths create a space that feels majestic.Perfectly situated just minutes from the University of Pittsburgh, Carnegie Mellon University, & UPMC’s world-class hospitals. This is more than a home — it’s a living chapter in Pittsburgh’s architectural legacy. Experience history, craftsmanship, and elegance coming beautifully together in the heart of Shadyside.

4749 Wallingford St, Shadyside

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

$45,000
Perfectly located commercial space in Shadyside with high traffic. Conveniently right next to the parking garage and surrounded by other popular restaurants and shopping and neighborhoods. This space gives a more private and cozy feel away from the street level, but with great artificial lighting and room for costumers. Currently occupied as a Dr. Tea tea place on the second floor, the business and equipment is for sale at $95,000 with a lease of $4000/month for the space.

736 Bellefonte St, Shadyside

Listing courtesy of KELLER WILLIAMS EXCLUSIVE.

$549,900
5 Beds ⋅ 3 Baths
This impressive 5-bedroom, 3-bath renovated & updated home in Shadyside offers a harmonious blend of space & functionality across three floors which seamlessly combines modern luxury with timeless charm. The 1st floor is open with loads of natural light. Living room is open to a spacious dining room & kitchen. A stunning modern kitchen with stainless steel appliances, white cabinetry, & a large island, all illuminated by stylish pendant lighting. Wood floors extend throughout the main living areas, adding warmth & character. First floor also offers a flex space that can be used as a den, office or family room. Bathrooms showcase a mix of contemporary & traditional designs, with one featuring a sleek walk-in shower & another boasting charming black & white tilework. The bedrooms are spacious & bright, with the primary bedroom offering a decorative fireplace & large windows. Conveniently located to Oakland, Bloomfield, Downtown, shopping, restaurants, Children’s & West Penn Hospitals.

159 Morewood Avenue, Shadyside

Listing courtesy of NEIGHBORHOOD REALTY SERVICES.

$178,500
1 Beds ⋅ 1 Baths
Welcome home to this newly painted one-bedroom, one-bathroom condominium in the Historic Highwood Condominiums located in Shadyside. This first floor condominium offers hardwood floors in the living room and bedroom with title in the kitchen and bathroom. Condo offers a large living room and spacious bedroom with eat-in kitchen that is bright and airy. Enjoy the rooftop deck and the panoramic views. There is storage in the unit plus additional locked storage in the basement. Laundry and bike storage are in the basement. Enjoy walking to various restaurants, Ellsworth Avenue, S. Highland, and Walnut business districts. Transportation to Pitt, CMU and Chatham is across the street.

372 S Highland Ave Unit 103, Shadyside

Listing courtesy of COLDWELL BANKER REALTY.

$499,000
2 Beds ⋅ 2 Baths
Welcome to this beautifully crafted two-story condo located in Pittsburgh’s Shadyside neighborhood. This unique residence blends timeless architectural charm with modern convenience, featuring gorgeous original woodworking, coffered ceilings, and abundant natural light throughout. Step into the stunning sunroom, perfect for a morning coffee or a cozy reading nook. The updated kitchen boasts stainless steel appliances, a breakfast bar, and plenty of storage—ideal for both everyday living and entertaining. Upstairs, you'll find two spacious bedrooms and a spacious full bath, while a convenient half bath is located on the main floor. Enjoy the ease of in-unit, full-size laundry, and the rare benefit of a private one-stall garage with additional off-street parking—a true luxury in Shadyside. Situated close to major hospitals, universities, shops, and restaurants, this condo offers the perfect combination of location, character, and convenience.

6109 Fifth Avenue Unit 2, Shadyside

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

$4,999,000
8 Beds ⋅ 8 Baths
A chance to own one of the largest lots in the heart of West Shadyside. Magnificient mini mansion on property along with 39,000 square foot adjacent lot that is possibly subdividable. The property also has a governers drive which leads up to this incredible dwelling infused with huge rooms,stained and leaded glass,ornate wood original moldings and built ins,gleaming hardwood floors,an indoor swimming pool and newer addition with newer kitchen. Carriage house on property. One of Shadysides biggest properties. Blocks froim Shadyside shopping and dining. Close proximity to schools,universities and hospitals..

5238 Ellsworth Avenue, Shadyside

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

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