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$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.

$199,900
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.

$749,900
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.

$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.

$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.