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$1,955,000
7 Beds ⋅ 4 Baths
Timeless Grandeur Reimagined. Built in 1892 for one of Pittsburgh’s distinguished Gilded Age families, this 7 bedroom, 3.5 bathroom West Shadyside estate is set on one of the neighborhood’s most sought-after streets. Rich in history and architectural presence, the home offers grand, open entertaining spaces, highlighted by an extraordinary central dining room that anchors the first floor and reflects the scale and elegance of a bygone era. A rare highlight is the large, flat, and exceptionally private fenced backyard, offering estate-like grounds seldom found in this location—ideal for outdoor entertaining, gardens, or a quiet retreat. The carriage house/garage provides additional flexibility and long-term potential, allowing for thoughtful enhancements tailored to modern luxury living. With gracious proportions, strong architectural integrity, and an irreplaceable setting, this is a unique opportunity to steward and elevate a historic Shadyside estate for the next generation.

4916 Wallingford St, Shadyside

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

$2,100,000
3 Beds ⋅ 4 Baths
Sitting on the corner of Castleman and Amberson in the coveted West Shadyside area, this immaculate totally updated home is terrific in every way. Gleaming hardwood floors, large room sizes,master ensuite with seperate office that could be a fourth bedroom,a few steps up to two bedrooms and bath, three zoned heating and cooling,finished basement,flat mansard roof with slate coving all around, surrounded by green space and steps from Walnut shopping and dining. This special residence has everything.

800 Amberson, Shadyside

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

$185,000
1 Beds ⋅ 1 Baths
Beautiful Open Floor Plan Condo With Private Balcony Located In, Shadyside...The Most Sought After Area In The City and Is Only 2 Mins Walk to Great Restaurants, Coffee Shops, Dr Offices and Retail. The updated kitchen features granite, tile backsplash, brand new dishwasher, and a massive island for entertaining guests. Both the living room ?& bedroom feature new paint and walls of windows washing your home with brilliant sunlight year-round. Of Course you can always step out on your own balcony to take in the sun. Your King Size Bed will be an easy fit in your spacious bedroom. The Secure entrance building has? an elevator to all levels, storage, laundry facility, and paid interior parking. The HOA includes heating, cooling, water, sewage, trash, and common area maintenance with recent updates to the laundry room and new hot water heaters. With 2 mins Walk to Walnut St, Bakery Square, Universities, Hospitals & Public Transportation a block away City Living Doesn't Get Any Better!

5619 Kentucky Ave Unit 104, Shadyside

Listing courtesy of KELLER WILLIAMS EXCLUSIVE.

$590,000
3 Beds ⋅ 4 Baths
In the heart of Shadyside, 627 S Aiken offers a rare blend of historic character and modern flexibility. This spacious three-story beauty features a bright open floor plan accented by exposed wood beams, intricate stained glass windows, and three cozy fireplaces. With 3 bedrooms, 3 baths, and a powder room, the home provides ample space for comfort and creativity. A private second-floor balcony and elegant staircases add architectural interest throughout. Enjoy the luxury of a two-car off-street parking pad—a true rarity in this prime location! Just steps from Walnut Street’s boutiques and dining, and less than a mile from Pittsburgh's universities and major medical centers, this property offers the ultimate in convenience and city living. An added bonus of the location also allows for business or mixed-use possibilities, making it a standout opportunity for those seeking a home with both style and purpose.

627 S Aiken Ave, Shadyside

Listing courtesy of COMPASS PENNSYLVANIA, LLC.

$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.

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