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$849,000
3 Beds ⋅ 4 Baths
Outstanding location, in the heart of Shadyside, this sophisticated beautifully renovated two story home offers the perfect blend of timeless character and sophisticated modern design. Ideally located within walking distance to a major Medical Center, Universities, boutique shopping, and an outstanding selection of restaurants andcafes. Premier coeducational school Winchester Thurston is directly across the street. Lovingly maintained by the same owners for 48 years, this home features beautiful oak hardwood floors, an inviting living room with mirrored glass shelving, decorative marble fireplace and a cozy first-floor family room. The renovated kitchen features maple cabinetry, stainless steel appliances, including electric stove plus separate wall oven, French door refrigerator, microwave oven and breakfast nook with built-in seating. Upstairs are three bedrooms, including a primary suite with a private bath and walk-in shower, plus a second full bath. The finished lower level includes a gameroom which is ideal for a home office or gym, half bath, laundry, storage, and an integral garage. Beautiful landscaping, an automatic irrigation system, and a private side yard complete this exceptional home. All mechanical systems are in top condition, ring door bell, and the new roof has a 50 year warranty. YOU can move right into this home and be proud to call it HOME!

4940 Ellsworth Ave, Shadyside

Listing courtesy of COLDWELL BANKER REALTY.

$299,000
2 Beds ⋅ 3 Baths

5048 Fifth Avenue Unit 101, Shadyside

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

$469,000
2 Beds ⋅ 2 Baths
This two-story brick townhouse, built in 1900, offers a blend of historic Shadyside character and modern updates. The bright interior features contemporary laminate flooring throughout the main living space and recessed lighting throughout the home. The kitchen is equipped with high-end appliances, a full-length pantry, and premium cabinets and fixtures. The interior layout features a master suite with a spacious wardrobe closet, two bathrooms, and a main living area centered around a cozy fireplace. The home is equipped with central air conditioning and forced-air gas heating. A finished basement provides versatile extra space, dedicated storage, and includes a front-load washer and dryer.Outside, a covered back patio offers a private outdoor retreat with low-maintenance landscaping. The property is situated in an established neighborhood, providing convenient access to public transit, local dining, and retail options.

5847 Pierce St, Shadyside

Listing courtesy of FSBO BROKER LLC.

$375,000
3 Beds ⋅ 2 Baths
Hidden in one of Pittsburgh's best-kept pockets, this distinctive home offers the perfect blend of privacy, space, and unbeatable convenience. Tucked away just off S. Negley Avenue and Centre Avenue, you'll enjoy being just moments from Shadyside and West Penn Hospitals, Market District, Walnut Street, Bloomfield, and some of the city's best dining, shopping, and entertainment. Whether you're a physician, nurse, hospital employee, or simply someone who loves living close to everything, this location is hard to beat. Step inside and you'll immediately be drawn to the dramatic two-story living room, where soaring ceilings and abundant natural light create an inviting, open atmosphere. The living room flows seamlessly into the dining area, while hardwood floors add warmth and character throughout the main level. The spacious eat-in kitchen offers plenty of room for everyday living and entertaining, with the opportunity to update it to reflect your own style. Outside, enjoy a brand-new front porch or unwind on the private rear porch and patio, tucked beneath a beautiful canopy of mature trees. Upstairs, the unique primary suite overlooks the living room below and features a cozy sitting area, an oversized bath, and a generous dressing area. The third floor offers two additional large bedrooms, providing flexibility for family, guests, a home office, or creative space. Move right in and update over time, or transform this home into something truly spectacular. With its exceptional location, distinctive architecture, generous living spaces, and attractive price, this is a rare opportunity to create lasting value in one of Pittsburgh's most sought-after neighborhoods.

412 Noble Street, Shadyside

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

$715,000
3 Beds ⋅ 3 Baths
Welcome to 704 Ivy Street, ideally situated on a picturesque tree-lined street in the heart of Shadyside! Just a few minutes walk to vibrant Walnut Street with its popular coffee shops, boutiques, and restaurants, this home also offers an easy commute to Pittsburgh's renowned hospitals, universities, and downtown. Full of timeless character and ready for your personal touch, this spacious home offers endless potential to make it your own. A charming covered front porch welcomes you inside, where you'll find high ceilings, hardwood floors, and generously sized rooms throughout. The inviting living room features a fireplace, while the dining room opens through patio doors to a covered rear porch—perfect for relaxing or entertaining. The large eat-in kitchen offers abundant cabinetry, pantry space, and there is also a convenient first-floor laundry room with lots of storage too! Upstairs, the generous primary suite features an abundance of closet space and a private ensuite bathroom. Two additional spacious bedrooms with roomy closets and a full hall bathroom complete the second floor. The third floor has a finished attic space with built ins for plenty more storage. Enjoy the private fenced rear patio and deck, ideal for outdoor dining, gardening, or entertaining. A detached two-car garage provides excellent parking and storage. The home also has new roof which is an added bonus. A wonderful opportunity to create your dream home in one of Pittsburgh's most sought-after neighborhoods!

704 Ivy Street, Shadyside

Listing courtesy of BERKSHIRE HATHAWAY HOMESERVICES THE PREFERRED REAL.

$1,195,000
6 Beds ⋅ 4 Baths
A rare Shadyside masterpiece where timeless architecture, modern luxury, and an unbeatable city lifestyle come together in unforgettable fashion. Perfectly positioned on a prominent corner lot, this Luxury residence makes a statement from the moment you arrive, offering the character buyers dream of, the updates they demand, and the outdoor living that is nearly impossible to find in the heart of the city. Step inside and prepare to be captivated by the original woodwork, rich architectural details, soaring ceilings, hardwood floors, and stunning stained-glass windows that fill the home with warmth, charm, and history. Every room tells a story, yet the home lives beautifully for today. The main level is designed to impress, with gracious living spaces, incredible scale, and a grand kitchen that serves as the heart of the home. French doors open to a screened-in porch, creating an effortless connection between indoor and outdoor living. Beyond that, enjoy a perfectly sized yard and one of the most extraordinary features in Shadyside, an unbelievable rooftop deck above the 2-car garage. Private, elevated, and completely unexpected, this outdoor space is ideal for entertaining, relaxing, dining under the stars, or enjoying a quiet city escape. The second floor offers a gorgeous primary suite that feels refined, private, and luxurious. The newly renovated primary bath is spectacular, featuring a soaking tub, oversized shower, and a spa-like design that elevates everyday living. Second-floor laundry adds convenience exactly where you want it. With 6 bedrooms total, this home offers incredible flexibility for family, guests, offices, fitness, creative space, or extended stays. The third floor includes 4 additional bedrooms and a full bath, creating a rare level of space and function. The finished lower level adds even more lifestyle appeal with a game room and TV/movie room, perfect for movie nights, entertaining, or casual everyday living. The location is simply unmatched. Live minutes from Pittsburgh’s major universities, hospitals, technology centers, Bakery Square, East Liberty, Oakland, and Downtown, while enjoying the walkable charm that makes Shadyside one of the city’s most sought-after neighborhoods. Stroll to Walnut Street for boutique shopping, coffee, dining, and neighborhood favorites, then return home to a property that feels private, gracious, and truly special. This is not just a beautiful Shadyside home. This is the one buyers wait for with historic character, modern luxury, rare outdoor living, a 2-car garage, and an address that delivers the very best of Pittsburgh living.

601 Emerson St, Shadyside

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

$4,450,000
7 Beds ⋅ 5 Baths
Welcome to Pittsburgh's "Garden House," an iconic Shadyside estate where timeless architecture and storybook gardens converge in one of Pittsburgh’s most coveted neighborhoods. Designed in 1913 by renowned Pittsburgh architect Edward J. Weber, this classic English Cottage Revival home boasts stucco walls, half-timber gables, and a sweeping slate roof. Tucked behind a charming gate, natural stone walls, and a picket fence draped in rambling roses are lush perennial gardens that surround the peaceful outdoor living spaces. As you enter this exceptional 7-bedroom, 4.5 bath residence, you are welcomed by a gracious foyer anchored by a grand staircase that makes an unforgettable first impression. The rich original craftsmanship has been beautifully preserved throughout, offering a rare blend of grandeur, warmth, and enduring elegance. From the moment you arrive, this meticulously restored home captivates with its distinctive hand-carved woodwork, period fireplaces, and original hardwood floors that span the homes expansive living spaces. To the rear of the residence, just beyond the serene stone patio, is a four-car carriage house, with an unfinished chauffeur’s quarters above which offers exceptional potential as a guest cottage or artist's studio. Thoughtfully designed for elegant entertaining and refined everyday living, this remarkable residence offers scale, character, and sophistication which is rarely found today. This distinguished property places you moments from Pittsburgh's finest dining, boutiques, universities, hospitals, and cultural institutions, while still offering the privacy and serenity of a true urban oasis. Iconic. Timeless. Unforgettable. "The Garden House" is more than a home — it is a cherished piece of Pittsburgh history.

704 Amberson Avenue, Shadyside

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

$2,725,000
8 Beds ⋅ 6 Baths
This remarkable Queen Anne Victorian is more than a home—it is a legacy property, offering historic significance, architectural beauty, and a rare opportunity to own a treasured piece of Pittsburgh's past. Prominently situated on a coveted corner lot in the heart of West Shadyside, this distinguished residence features eight bedrooms, four full bathrooms, and approximately 4,751 square feet of living space on an expansive 0.30-acre lot. Built in 1885 and designed by renowned Pittsburgh architect George Orth, the home stands as one of the neighborhood's finest and best-preserved examples of late-19th-century Queen Anne Victorian architecture. Hallmark design elements include a complex roofline, decorative gables, bay windows, intricate masonry, multiple chimneys, and a striking asymmetrical façade. Steeped in Pittsburgh history, the property was the longtime residence of the Spencer family, whose life within the home was later immortalized in the book The Spencers of Amberson Avenue. Beginning in 1968, the home entered a new chapter with the Fairman family, continuing its enduring role in the evolving story of Shadyside. A gracious vestibule adorned with encaustic tile opens to an elegant foyer, while a grand staircase set the tone. Expansive, light-filled rooms unfold throughout the main level, including a spacious living room with a floor-length side door and a distinctive diagonal bay, an elegant formal dining room, and a stately library lined with floor-to-ceiling bookshelves. Rich architectural details abound, from oak hardwood floors and operational pocket doors to classic wainscoting, custom built-ins, multiple hand-painted slate mantel fireplaces, and soaring 11-foot ceilings. Beautifully preserved leaded and stained-glass windows fill the home with natural light, while charming hideaway shutters provide exceptional craftsmanship. The bright and inviting kitchen features a sunny breakfast nook and offers direct access to the backyard garden. The second floor offers four spacious bedrooms and three full bathrooms, including a remarkable library and art studio. The third floor—once the servants' quarters—has been thoughtfully reimagined as a private retreat, featuring two comfortable bedrooms, a living room with a cozy nook, and a dedicated wellness space complete with a massage area, yoga space, and a beautifully preserved vintage world map wall that adds charm and peaceful vibes. Outside, the level backyard provides a rare sense of privacy and space, with a beautifully landscaped mature garden and a patio for outdoor entertaining and relaxing. A detached three-car garage is discreetly positioned at the rear of the property. Located on one of Shadyside’s most picturesque tree-lined streets, this exceptional residence offers convenient access to renowned schools, boutique shopping, acclaimed restaurants, major universities, world-class medical centers, and everything Pittsburgh’s vibrant East End has to offer.

719 Amberson Ave, Shadyside

Listing courtesy of COLDWELL BANKER REALTY.

$1,000,000
3 Beds ⋅ 5 Baths
Unique Mixed-Use Opportunity in the Heart of Shadyside Welcome to 5884 Ellsworth Avenue, a truly unique and iconic Shadyside property offering endless possibilities for investors, entrepreneurs, artists, and owner-occupants alike. Home to the renowned Photo Forum since 1986, this one-of-a-kind property consists of three distinct units: a commercial café space, a residential apartment/art gallery, and a separate two-bedroom house. The main building features a charming 30-seat café on the first floor, currently configured for food and beverage service. Rich in local history, the space once housed the beloved Con Alma before its move downtown. Guests can enjoy a beautifully landscaped 35-seat outdoor patio complete with a tranquil koi pond and mature gardens, creating an inviting urban oasis. The upper levels of the main building offer exceptional live/work flexibility. The second floor is currently home to the Photo Forum photography gallery and includes a kitchen with access to a private deck. The residential space extends to the third floor, offering a spacious one-to-two-bedroom apartment highlighted by a stunning solarium. Above it all, a rooftop deck provides breathtaking panoramic views of Shadyside and the surrounding neighborhoods. Adding even more value, the property includes a separate two-bedroom house located at the rear of the lot with alley access, creating additional rental income potential, guest accommodations, or owner occupancy options. Outdoor living and entertaining spaces abound, from the café patio to the private residential deck and expansive rooftop terrace. Situated in one of Pittsburgh's most walkable neighborhoods, the property enjoys constant foot traffic and is just steps from the shopping, dining, and entertainment districts of Shadyside and East Liberty. Major universities, hospitals, and employment centers are only a short drive away. Whether you're seeking an investment opportunity, a live/work environment, or a landmark property with character and history, 5884 Ellsworth Avenue is a rare offering unlike anything else on the market.

5884 Ellsworth Ave, Shadyside

Listing courtesy of COLDWELL BANKER REALTY.

$789,000
3 Beds ⋅ 3 Baths
Welcome to The Revival - a masterful blend of historic soul and modern sophistication in the heart of the city. This beautifully reimagined residence seamlessly combines timeless architectural character with sleek contemporary upgrades, creating a home that feels both warm and elevated from the moment you step inside. Original exposed brick and striking wood beams pay homage to the home’s history, while thoughtful renovations bring it firmly into today’s luxury lifestyle. The centerpiece living space is anchored by a stunning modern fireplace that contrasts perfectly against the home’s rich textures and industrial-inspired details. The fully renovated kitchen delivers clean lines, sleek finishes, updated cabinetry, and modern functionality designed for both daily living and entertaining. Contemporary bathroom fixtures and stylish upgrades throughout the home create a polished, designer feel without sacrificing charm or authenticity. Rare for a home with this level of character, The Revival also features a coveted two-car garage, offering convenience that perfectly complements the home’s urban appeal. Perfectly positioned in one of Pittsburgh’s most vibrant and walkable neighborhoods, you’re just moments from Walnut Street, neighborhood bakeries, cafés, restaurants, boutiques, and everything that makes city living exciting. Whether grabbing coffee on a quiet morning or enjoying a night out steps from your front door, this location captures the very best of Pittsburgh living. This is not simply a renovation…it’s a rebirth. A home where old-world craftsmanship and modern design collide in all the right ways.

357 Lehigh Avenue, Shadyside

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

$519,000
3 Beds ⋅ 1 Baths
Charming 3-bedroom Victorian in the heart of Shadyside with garage parking. Features 10-foot ceilings on the first floor, hardwood floors throughout, and an updated galley kitchen with granite countertops, Miele wall ovens, and a Miele warming drawer. Space available to add a first-floor powder room. Second floor offers two bedrooms, a den, and a renovated full bath. Expansive walkout basement with 10-foot ceilings provides excellent storage or future finishing potential. Enjoy a private rear courtyard, newer front porch, and fenced yard. A wonderful blend of classic character and modern updates in a prime location.

5733 Kentucky Ave, Shadyside

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

$967,000
5 Beds ⋅ 4 Baths
Historic Shadyside character meets the ease of condominium living at 703 Saint James Street. Set along one of the neighborhood’s most distinguished residential streets, this second-floor condominium residence offers two levels of private living space and the scale, warmth, and architectural presence of a classic Pittsburgh home. Built circa 1900, the residence showcases original Tiger’s Eye White Oak floors, substantial moldings, built-in cabinetry, high ceilings, and a wood-burning fireplace. The main living level features gracious gathering spaces, a Viking Professional 36-inch six-burner range, and a spacious primary suite with walk-in closet, additional closet space, and en-suite bath with smart toilet and bidet. The second level adds two large bedrooms and a full bath, with newly added interior stairs improving flow and functionality between the two levels. Two exceptional office spaces offer flexibility for modern living, including one with a private balcony and sound-dampening door, and another with built-ins and an attached half bath. Recent updates include new windows, carpet, blinds, re-grouted kitchen and bathroom tile, updated electrical panel, new second-level HVAC in 2023, new main-level HVAC in 2025, and a new patio door and private deck off the front office in 2024. Large additional basement storage and a one-car garage space are included. The HOA supports a more service-conscious ownership experience, with items that include lawn care, snow removal, window cleaning, gutter cleaning and clearing, and HOA insurance policy. Minutes from Walnut Street, Ellsworth Avenue, restaurants, boutiques, universities, hospitals, and downtown Pittsburgh, 703 Saint James offers historic architecture, generous interior space, condominium convenience, and a more manageable way to own in the heart of Shadyside. Details about our seller offered repair allowance upon request.

703 Saint James St, Shadyside

Listing courtesy of KELLER WILLIAMS STEEL CITY.

$3,900,000
6 Beds ⋅ 6 Baths
Welcome to 1101 Shady Avenue—where effortless luxury meets the best of the East End. Set on lush, manicured grounds, this estate delivers true country club living at home, complete with a private pool, sport court, and putting green—an everyday escape designed for both play and entertaining. Inside, timeless architecture meets a fresh, elevated feel. Expansive, light-filled spaces flow seamlessly from room to room, creating a layout that lives as beautifully as it entertains. The kitchen anchors the home, opening to inviting gathering spaces that strike the perfect balance between relaxed and refined. With 6 bedrooms and 5.5 baths, the home offers exceptional flexibility for family and guests alike. The primary suite is its own retreat, featuring a custom dressing room and a spa-level, marble-clad bath designed for total unwind. Tucked in one of Pittsburgh’s most coveted neighborhoods, just moments from Shadyside’s best dining, boutiques, hospitals, and universities, this is a rare offering—private, polished, and effortlessly cool.

1101 Shady Avenue, Shadyside

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

$1,299,000
5 Beds ⋅ 4 Baths
Major price improvement! Seller is relocating and highly motivated to make a deal. An incredible opportunity to own a unique Victorian loft. A Masterpiece of Light and Silence: 1900 Victorian Reimagined. This is not just a house; it is a meticulously contemplated space designed to fulfill the deepest fantasies of the soul. Originally built in 1900, this classic three-story Victorian residence underwent a profound transformation in the 1980s under the visionary direction of a Professor of Architecture. The result is an introverted, minimalist sanctuary that harmonizes historical grandeur with modern simplicity. The Dance of Light At the heart of the home lies a breathtaking two-story Loft. As the sun begins its descent, the space is flooded with golden, warm hues, seamlessly bringing the outdoors in. The shimmering sunlight creates a rhythmic vitality throughout the room, turning the interior into a living canvas of light and shadow. The Cloud Room: A Sanctuary of Silence In stark contrast to the sun-drenched loft, tucked between the kitchen and the dining area, lies "The Cloud Room." This windowless, secret chamber offers total tranquility. With its built-in bookshelves and private bar, it serves as a quiet retreat for contemplation, reading, or an evening glass of wine. An Urban Oasis The garden and courtyard have been designed with a philosophy of "Sui Yuan" (ease and serenity), creating an extraordinarily quiet atmosphere in the heart of the bustling city. It is a rare urban hideaway that invites you to linger and never want to leave. Key Features: Designed by a distinguished Professor of Architecture. Dramatic two-story Loft with exceptional western exposure. The "Cloud Room": A unique, windowless library and bar. Serene private courtyard and minimalist landscaping. A thoughtful blend of 1900 Victorian character and 1980s minimalism.

5820 Howe St, Shadyside

Listing courtesy of THE GREENE REALTY GROUP.

$2,600,000
4 Beds ⋅ 4 Baths
Located in the heart of Shadyside, this stately brick Colonial blends timeless architecture with modern amenities. Exceptional curb appeal begins with manicured landscaping that includes hydrangeas which bloom all summer long, a two-car detached garage, a two-car pan driveway and a private fenced yard that offers a brick patio and grilling area. Inside, refined living spaces feature hardwood floors, crown molding, marble mantels, custom built-ins, and elegant formal and casual rooms. The kitchen is anchored by two Wolf ovens, a Wolf cooktop, a Sub-Zero refrigerator and granite countertops. The spacious primary suite includes a beautifully finished bath and custom walk-in closet with laundry. The finished third floor and basement add flexible living spaces and two full bathrooms. Ideally located on a private cul-de-sac near Walnut Street and Ellsworth Avenue.

619 Pitcairn Place, Shadyside

Listing courtesy of HOMECOIN.COM.

$3,390,000
8 Beds ⋅ 6 Baths
Homes of this caliber are increasingly rare—not simply because of their architecture, but because they continue to live so beautifully. Carefully preserved, thoughtfully updated, and remarkably adaptable, 400 Devonshire is equally suited for elegant entertaining, multigenerational living, working from home, or simply enjoying the comfort and character of a residence that feels both established and timeless. The main residence offers seven bedrooms, three full bathrooms, and two half bathrooms. Above the detached two-car garage, the fully renovated carriage house provides exceptional flexibility with a private guest suite, full bathroom, eat-in kitchen, and laundry—ideal for extended family, long-term guests, a home office, or a creative studio. Ideally located just blocks from Shadyside's boutiques, cafés, acclaimed restaurants, parks, and Pittsburgh's premier cultural and academic institutions—including Carnegie Mellon University and the University of Pittsburgh—the home offers a lifestyle defined by walkability, convenience, and enduring neighborhood charm. A gracious entry welcomes you into a thoughtfully designed first floor featuring two spacious living areas, a formal dining room, an eat-in kitchen, and a dedicated office. Throughout the home, original architectural details—including soaring ceilings, generous room proportions, rich millwork, and abundant natural light—blend seamlessly with a floor plan that adapts effortlessly to modern living. Several bedrooms have been thoughtfully reimagined as home offices, lounge spaces, and entertainment rooms, demonstrating the home's remarkable versatility. Outside, mature gardens create a private urban retreat, highlighted by tranquil landscaping and a picturesque koi pond. The outdoor spaces feel as inviting as the interiors, offering peaceful settings for entertaining or quiet relaxation. Thoughtfully integrated modern improvements, including discreet solar panels, enhance efficiency while preserving the home's historic character and architectural integrity. The result is a residence that honors its past while meeting the expectations of contemporary living—a truly exceptional offering in one of Pittsburgh's most sought-after neighborhoods.

400 Devonshire St, Shadyside

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

$594,900
2 Beds ⋅ 3 Baths
Location, Location! An Elegant 2Bd, 2.5Ba, 1Car Garage Colonial Style Home with a Fenced in Backyard, Located in a Highly Desired SHADYSIDE area. Home Offers a Recently Renovated Kitchen with a Brand New Cabinets, Granite Countertops, Stainless Steel Appliances and a Beautiful Backsplash. Hardwood Floors All Throughout the House. The Main Level Offers a Large and Bright Dining Room with Charming Built Ins, Crown Molding, wainscoting and a Fireplace. Powder Room with a Pedestal Sink and a built in closet. A Living Room with Tasteful Crown Molding, Accented Woodwork, Built ins and a Fireplace, an Easy Access into the Fenced In Courtyard where You can Relax and Entertain with a Bliss. The Upper Level Offers Hardwood Floors and Plenty of Light. An En-Suite with a Walk-in Shower, a Beautiful Vanity witha Marble Countertop, Wainscoting, Crown Moldings, a Walk-in Closet and a Laundry Room. The Second Generously Sized Bedroom also Offers an En-Suite Bathroom with a Tub/Shower Combo. The 1 Car Garage Conveniently Located Right off Of the Kitchen where Unloading your Groceries is at Ease. A walking Distance to Frick Park, Colleges, Shopping and Entertainment.

1 Schoolhouse Ln, Shadyside

Listing courtesy of RE/MAX SELECT REALTY.

$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.

$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.

$1,350,000
4 Beds ⋅ 4 Baths
Currently a legal Duplex with a lovely 2 bedroom, open floor plan, dual sink large bathroom and spacious balcony on 3rd floor apt. First and second floorhave an open floor plan that includes a living room, dining room, family room, kitchen that seats four at the island, and two doors to access the awning-covered terrace porch that overlook extensive gardens. Abundant custom closets on all levels that include a walk in cedar and two coat closets. Laundry on second floor and the basement. 3 large off street spaces in the rear that allow for easy turn around. Also listed as a Duplex, MLS #1739804. Separate side entry to the apt. Door on the first floor leads to the apt. Add a door on the 2nd floor landing and you have a single family space. The income, if kept as a rental, is always naice and tenants are always available. Current month to month.

918 S Aiken Ave, Shadyside

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

$999,000
4 Beds ⋅ 4 Baths
Just steps from the shops, cafes, and dining of Walnut St, this beautifully updated Shadyside residence combines timeless character with thoughtful modern updates. A welcoming front porch leads into the foyer and spacious living/dining rooms highlighted by hardwood floors, high ceilings, and two decorative fireplaces. French doors open to a bright sunroom, perfect as a home office or reading nook. The granite kitchen with stainless appliances flows seamlessly into a comfortable family room, creating the heart of the home. A rare 2-car garage provides ease and convenience. Upstairs, the primary suite offers a generous sitting area, walk-in closet, and private bath, along with direct access to an expansive sun deck ideal for entertaining or relaxing. The third floor serves as a private retreat with a bedroom, full bath, sitting room, large closet, and its own HVAC system. Elegant, versatile, and perfectly located, this home is Shadyside living at its finest.

702 Bellefonte 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.

$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.

$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.

$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.