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$850,000
Fantastic Owner Occupant or Investment Opportunity! Fully renovated 3 Floor 4 Unit in the heart of Shadyside!!! A very rare find! Unit 1 (occupied): Living, Kitchen, Bedroom, and Full Bath. Unit 2 (occupied): Living, Kitchen, Bedroom, Bedroom, and Full Bath. Unit 3 (occupied): Living, Kitchen, Bedroom, Bedroom, and Full Bath. Unit 4 (occupied): Living, Kitchen, Bedroom, and Full Bath. Many upgrades during ownership including kitchens and baths, refinished hardwoods, fresh paint, lights, electrical, plumbing, and some newer hvac, h2o tanks, windows, doors, etc. 5 electric, 4 gas, and 1 water meter. 2 mid level units have AC. Basement has laundry and plenty of storage. 4 Car Off Street Parking in Rear! Covered front porch and nice rear deck! Turn-key cash flow opportunity with strong appreciation potential because of this amazing location! Don't miss out on this building! Perfect for any investment portfolio or owner occupant looking to own and collect rent!

241 Amber St, Shadyside

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

$1,190,000
5 Beds ⋅ 4 Baths
Beautiful three-story brick home offering 5 bedrooms and 3.5 baths with abundant natural light throughout, ideally located in the heart of Shadyside. The open first floor features a seamless flow between the kitchen, living, and dining areas—perfect for both everyday living and entertaining. This modern style kitchen is equipped with custom cabinetry, soft-close drawers, generous cabinet space, and stainless steel appliances, creating a stylish and highly functional centerpiece of the home. The second floor includes three bedrooms, highlighted by a spacious primary suite featuring a fireplace, custom closet, and updated en suite bath. A conveniently located washer and dryer are also located on the second floor. The third floor offers two additional bedrooms along with a large open living space that provides flexibility for a family room, guest retreat, playroom, or home office. A full basement provides additional storage and potential. The property also features a two-car garage and additional off-street parking—an exceptional convenience in the city. All just minutes from Shadyside’s shopping, dining, and neighborhood amenities. Amazing location, amazing home! MUST SEE!

416 Denniston St, Shadyside

Listing courtesy of BERKSHIRE HATHAWAY THE PREFERRED REALTY.

$186,800
1 Beds ⋅ 1 Baths
Sun-drenched and inviting, this adorable one-bedroom condo offers a bright and airy retreat with wonderful views facing Bayard and looking toward Fifth Avenue. The interior features a clean, modern aesthetic with neutral walls and easy-care golden red oak laminate flooring throughout. The heart of the home is an updated kitchen complete with granite countertops, stainless steel appliances, and a large pantry for ample storage. An expansive, open-concept living and dining area provides incredible versatility, offering plenty of space for a home office, a full dining set for hosting game nights, and a large-screen media setup. This sense of space extends to the bedroom, which comfortably accommodates a king-sized bed, dressers, and a desk, all supported by generous closet space throughout the unit. Life at this building comes with an impressive suite of amenities, highlighted by a massive, playing-field-sized patio perfect for setting up badminton nets or enjoying a cookout at the provided grills. For even more dramatic views, head to the rooftop deck to soak in the sun and enjoy a spectacular 360-degree panorama of the city. Residents also benefit from a workout room, a community room, and the convenience of laundry facilities on both the residential floor and the lower level. Assigned indoor and outdoor parking is available for a fee. Providing ultimate peace of mind and simplified budgeting, the comprehensive HOA fee covers all major utilities—gas, electric, water, and sewer—as well as common area maintenance and contributions to the reserve funds. Seller will pay the capitalization fee for the buyer.

5 Bayard Rd Unit 717, Shadyside

Listing courtesy of YOUR TOWN REALTY LLC.

$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.

$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.

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