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$235,000
2 Beds ⋅ 2 Baths
Experience maintenance-free living in one of Pittsburgh's most sought-after condominium communities Amberson Towers—located in the heart of Shadyside. Unit 418 is where comfort, convenience, and timeless style come together. This beautifully maintained two-bedroom, two-bath residence offers the perfect blend of updated comfort, convenience, and an unbeatable location just moments from shopping, dining, universities, hospitals and entertainment. Updated flooring, fresh paint, a refreshed kitchen, and modern fixtures make this home truly move-in ready—offering a turnkey opportunity that's simply waiting for you to make it your own. Life at Amberson Towers extends well beyond your front door. enjoy access to a variety of on-site amenities, including a fitness center, community lounge, laundry and rooftop terrace, providing opportunities for relaxation and socialization. Additionally, the building offers convenient services such as 24-hour maintenance. Explore the photos, take in everything this exceptional home and the sought-after Amberson Towers community have to offer, and imagine yourself living in the heart of Shadyside. Opportunities like this don't come along often—schedule your private tour today and make your move before someone else does!

5 Bayard Road Unit 418, Shadyside

Listing courtesy of COLDWELL BANKER REALTY.

$225,000
2 Beds ⋅ 1 Baths
**Exceptional Location in the Heart of Shadyside/East Liberty! This Beautifully updated 2-bedroom home just steps from Bakery Square and the Walnut Street shopping district, with popular restaurants, cafés, boutiques, and specialty shops right outside your door. Easy access to Pitt, CMU, UPMC, and downtown via nearby public transportation. **Inside, the thoughtfully renovated kitchen and bathroom showcase contemporary finishes and timeless design. The spacious living room provides a versatile layout with plenty of room for entertaining, relaxing, or working from home. Two generously sized bedrooms offer comfort and flexibility, while hardwood floors throughout add warmth, character, and easy maintenance. **A standout feature is the rooftop deck, where you can enjoy panoramic city views, sunshine, and beautifully maintained flower gardens—an inviting retreat for morning coffee, evening sunsets, or entertaining guests.

372 S Highland Ave Unit 102, Shadyside

Listing courtesy of KELLER WILLIAMS STEEL CITY.

$599,900
3 Beds ⋅ 2 Baths
Welcome to 411 The Lofts at Shadyside, a double-unit condominium in one of Shadyside’s most sought-after neighborhoods. Filled with natural light, this residence showcases industrial-style ceilings, exposed brick walls, three spacious bedrooms, an open kitchen, two full baths, a laundry room, and new wall-to-wall carpeting. It also includes access to a two-car tandem garage space and storage in the building. The secure building is professionally managed on-site and offers a rooftop deck with incredible views.

5850 Centre Ave Unit 411, Shadyside

Listing courtesy of BERKSHIRE HATHAWAY HOMESERVICES THE PREFERRED PROP.

$209,990
1 Beds ⋅ 1 Baths
Welcome to Unit #104 at Amberson Towers Condominium in the heart of Shadyside. Beautifully updated throughout and move-in ready, this thoughtfully renovated residence offers the open floor plan, functionality, and modern finishes today’s buyers are seeking—all with the convenience of first floor living. Updates include flooring throughout, crown molding, replacement interior doors, a custom closet organization system, and a renovated bathroom with updated tile and vanity. Ideally located just minutes from Carnegie Mellon University, the University of Pittsburgh, renowned medical centers, and Shadyside’s premier dining and shopping destinations. Residents enjoy convenient parking options, while the monthly HOA fee covers all utilities, building maintenance, and security—providing exceptional value and truly low-maintenance living.

5 Bayard Rd Unit 104, Shadyside

Listing courtesy of CENTURY 21 FRONTIER REALTY.

$525,000
DUPLEX IN PRIME SHADYSIDE LOCATION! Endless opportunity with this home! You can keep it as a duplex and maintain a steady income from both units. You could owner occupy one unit and rent out the other. Or you could remove the wall separating the units and restore this home to a stunning single-family home. Unit #1 is a one bed and one full bath apartment with a fully equipped kitchen and roughly 815 sq. feet. Unit #2 boasts that Shadyside home charm. Mixing the old school charm with the modern updates supporting roughly 1,500 sq. feet and 3 bedrooms, 2 full bathrooms. Both units have their own laundry. To save the best for last, location, location, LOCATION! This home is walking distance to S. Highland St, Walnut St. & Bakery Square!

5972 Alder Street, Shadyside

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

$209,000
1 Beds ⋅ 1 Baths
GREAT INVESTMENT OPPORTUNITY IN THE HEART OF SHADYSIDE WITH 2 OFF-STREET PARKING SPACES!! Blocks to CMU, PITT, Chatham University, Shadyside Hospital, Walnut Street Shops and Restaurants. On the main bus line for Public Transportation and Universities. Move in ready, SECURE BUILDING, Laundry Room in Basement. Lots of Natural Light. Vinyl Flooring throughout with Carpet in the Bedroom. This condo has a STORAGE UNIT! HOA fee covers Water, Sewage, Gas, Gas Heat, and Trash Removal. OWNER is RESPONSIBLE for ELECTRIC. Units in this building CAN BE RENTED.

5237 Fifth Avenue Unit B1, Shadyside

Listing courtesy of RE/MAX SELECT REALTY.

$184,900
1 Beds ⋅ 1 Baths
Welcome to Amberson Towers Condominium in the heart of Shadyside! This upscale high-rise offers the perfect blend of convenience, comfort, and flexibility—whether you're ready to move right in or add your own personal touch. Unit 215 boasts boats plenty of natural light, updated kitchen and bath and a bonus room with a murphy bed that can be used as an office, guest room or dining room. Ideally located, you’re just minutes away from Carnegie Mellon University, the University of Pittsburgh, and renowned local hospitals, as well as the popular dining spots and vibrant shopping that Shadyside has to offer. Amberson Towers delivers a full-service lifestyle with exceptional amenities, including 24/7 security, a fully staffed management office with an on-site property manager, a well-equipped fitness center with streaming TV, a spacious party room, a guest suite, and a library. Parking options include three levels of indoor garage spaces (available for a fee) along with limited outdoor parking. Plus, the monthly HOA fee provides outstanding value by covering all utilities, building maintenance, and security. Everything you need is right at your door!

5 Bayard Rd Unit 215, Shadyside

Listing courtesy of BERKSHIRE HATHAWAY THE PREFERRED REALTY.

$1,199,000
3 Beds ⋅ 4 Baths
Discover luxury newer construction at 5133 Fifth Avenue in Shadyside, Pittsburgh's most prestigious neighborhood. Completed in 2023, this approximately 3,099-square-foot townhome features a private elevator accessing all three floors, an open floor plan, and high-end finishes throughout. The gourmet kitchen boasts Miele appliances and custom cabinetry. The living space anchors around a built-in fireplace with custom tile surround. Sonos built in speakers and the TV create an elevated entertainment space. The primary suite offers a Juliet balcony, 110-square-foot custom walk-in closet, and spa-like bath with soaking tub and walk-in shower. A dedicated office with built-ins and two guest rooms occupy the third floor, providing complete separation from the primary suite. Additional features include Sonos sound system, two-car garage, and a prime Shadyside location steps from museums, restaurants, fine dining, shopping, parks, Carnegie Mellon University, and the University of Pittsburgh. One of the few new construction homes in this established neighborhood.

5133 5th Avenue, Shadyside

Listing courtesy of PIATT SOTHEBY'S INTERNATIONAL REALTY.

$519,000
3 Beds ⋅ 3 Baths
Rare Opportunity: Stunning Townhouse on a Private Road in Shadyside Discover this exceptional townhouse, nestled in a private community in one of Shadyside’s most desirable pockets. Offering the perfect blend of privacy and convenience, it sits tucked away amid mature trees yet remains just steps from the neighborhood’s vibrant shops, dining, and amenities. Key Features Include: • Ground Level: An extra-long two-car garage with abundant storage space, plus a dedicated dry storage room. • Main Living Level: An inviting living room, elegant formal dining room, fully equipped kitchen, casual breakfast dining area, and a convenient powder room. • Second Floor: A spacious primary suite featuring an en-suite bathroom and generous walk-in closet, a secondary bedroom, a full hallway bathroom, and a laundry closet equipped with a washer and dryer. • Third Floor: A versatile third bedroom, ideal for guests, a home office, or additional living space. This beautifully designed home boasts abundant storage throughout—including multiple closets and pantry space—along with expansive windows that flood the interior with natural light. Surrounded by lush greenery, it delivers a serene, secluded atmosphere while maintaining effortless access to everything Shadyside has to offer. A truly rare find—schedule your private showing today!

9 Graham Pl, Shadyside

Listing courtesy of BERKSHIRE HATHAWAY HOMESERVICES THE PREFERRED PROP.

$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.

$1,199,900
Rare opportunity to own a beautifully maintained and income-producing property in the heart of Shadyside. This charming Victorian-style property features high ceilings, timeless character, and numerous updates throughout. The property consists of three residential units, including two 2-bedroom, 1-bath apartments and one spacious 2-bedroom, 1.5-bath apartment and a finished Basement. All units are currently occupied, providing immediate rental income. Major improvements include updated furnaces, central air conditioning systems, roof, windows, doors, rear deck, and hot water tanks. Separate electric service is provided for each unit. A common laundry area is located in the basement for tenant convenience. Situated on a quiet street with ample off-street parking, this property offers an exceptional location just minutes from Shadyside's shopping, dining, entertainment, hospitals, and universities, as well as nearby Bloomfield's vibrant restaurant and nightlife scene. Whether you're expanding your investment portfolio or seeking a prime multifamily property in one of Pittsburgh's most desirable neighborhoods, this fully rented property is must-see.

191 Morewood Ave, Shadyside

Listing courtesy of REALTY ONE GROUP GOLD STANDARD.

$945,000
Rarely available and ideally located 5 unit in the heart of Shadyside. This 5-unit multifamily property presents an outstanding opportunity for investors seeking stable cash flow & long-term appreciation in one of Pittsburgh's most desirable neighborhoods. Two of the units extensively updated in the last two years. 8 bedrooms total, fully occupied. Positioned just minutes from Walnut Street's vibrant shopping and dining district, major employers, universities, hospitals, and public transportation, the property benefits from consistent tenant demand driven by professionals, graduate students, medical personnel, and long-term residents alike. 5 units total- two units are 1 bedrooms, three units are 2 bedrooms.

659 Maryland Ave, Shadyside

Listing courtesy of COMPASS PENNSYLVANIA, LLC.

$3,800,000
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.

$900,000
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.

$900,000
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.

$624,900
3 Beds ⋅ 3 Baths
Welcome to 5445 Fifth Avenue — a fabulous two-story townhouse in the heart of highly sought-after Shadyside. Bathed in natural light from oversized windows, this beautifully renovated residence seamlessly blends timeless charm with modern updates, offering effortless city living in one of Pittsburgh’s most vibrant neighborhoods. The thoughtfully designed main level features an expansive living room, an adjacent dining room ideal for entertaining, and a stylish galley kitchen complete with crisp white cabinetry and stainless steel appliances. An additional flex space provides the perfect opportunity for a home office, den, or potential fourth bedroom. Upstairs, you will find three generously sized bedrooms, including a serene en-suite primary retreat. Ample closet space and storage throughout add to the home’s everyday functionality. The finished lower level offers incredible versatility — ideal as a game room, family room, fitness area, or media space. Perfectly positioned just blocks from bustling Walnut Street, this exceptional home places the very best of Shadyside right outside your door. Enjoy easy access to Bakery Square, Downtown Pittsburgh, the Strip District, world-class hospitals, and leading universities, making daily commutes and weekend outings a breeze. Beautifully updated and impeccably located, 5445 Fifth Avenue is truly move-in ready — offering the rare opportunity to become part of one of Pittsburgh’s most desirable neighborhoods.

5445 Fifth Avenue, Shadyside

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

$349,500
3 Beds ⋅ 2 Baths
The most affordable 3-bedroom condo currently available in Shadyside — with an exceptionally low HOA of just $182 per month. This rare 3-bedroom, 1.5-bath home offers a spacious layout at a price point typically seen in smaller 2-bedroom units. Its low monthly HOA stands out in Shadyside, where many buildings carry substantially higher dues, creating a more cost-efficient ownership experience that may compare favorably to renting in the neighborhood. The unit includes a large in-unit storage and utility room with a washer and dryer, offering convenience and functionality rarely found in comparable Shadyside condos. Three true bedrooms provide flexibility for shared living arrangements, allowing occupants to distribute expenses in ways that may be more manageable than traditional single-bedroom or two-bedroom options. The condominium association recently completed and fully funded new roofing across all buildings, and no special assessments are currently anticipated. This major improvement provides added confidence in the long-term stability and financial health of the community. Located steps from Walnut Street, the property offers outstanding walkability to shops, dining, CMU, Pitt, and multiple nearby medical facilities. The location is ideal for nurses, interns, residents, fellows, and university affiliates seeking a convenient commute and predictable monthly living costs. A home warranty active through 2027 provides additional peace of mind, covering major kitchen and laundry appliances along with eligible electrical and plumbing systems. The home is move-in ready, offering a turnkey opportunity for owner-occupants, medical professionals, graduate students, and investors. Parking is convenient and reliable, with street options available directly out front and on nearby side streets, even during neighborhood events. Seller is motivated and open to discussing buyer-friendly terms.

940 Bellefonte St, Shadyside

Listing courtesy of THE GREENE REALTY GROUP.

$350,000
2 Beds ⋅ 2 Baths
Located in the heart of Shadyside, this spacious 2-bedroom, 2-bath condo offers a great layout in an ideal location. The fully renovated kitchen features stainless steel appliances, marble countertops, ample cabinetry, and convenient in-unit laundry. The bright living area includes dedicated dining space plus a flexible bonus area perfect for an office or sitting room. The primary suite offers great natural light and a private bath with walk-in shower. A generously sized second bedroom, full bath, and excellent closet space complete the unit. One assigned parking space is included, along with shared indoor and outdoor common areas. HOA fee of $617.15/month includes all utilities except electric, common area maintenance, and parking. Convenient to Shadyside’s shopping, dining, and neighborhood amenities.

5825 5th Ave Unit 314, Shadyside

Listing courtesy of RE/MAX SELECT REALTY.

$489,000
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.

$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.

$275,000
1 Beds ⋅ 1 Baths
Discover this penthouse condo in the heart of Shadyside, just steps from premier shopping, top universities, and leading medical facilities This spacious one-bedroom residence plus a a den, offers a rare sense of tranquility, creating a private oasis high above the city's vibrant energy. Enjoy, the convenience of an indoor parking space with 24/7 valet service. Unwind at the end of the day on your own private rooftop deck where you can take in breathtaking sunset views. The building features an extensive fitness center, multiple laundry facilities, and a generously sized private storage unit Experience elevated city living with convenience at your doorstep. Your pets are welcome! HOA fee includes heat, water, sewer, trash, basic cable, internet, valet, security/parking, landscaping & snow removal. Owner pays electric.

825 Morewood Ave Unit PH2, Shadyside

Listing courtesy of PIATT SOTHEBY'S INTERNATIONAL REALTY.

$2,950,000
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.

$450,672
3 Beds ⋅ 2 Baths
GREAT FOR STUDENTS! Walnut Street in Shadyside is best known for its upscale shopping, fine dining, private boutiques & now, you can live only a few minutes from all of it! This condo conversion does not only have the most sought after location in Shadyside but also has to offer it's new owner 3 bedrooms of considerable size, 2 full bathrooms, 2 car detached garage, log burning fireplace, in unit laundry & has been completely updated including a new roof!

712 S Aiken Avenue, Shadyside

Listing courtesy of RE/MAX REAL ESTATE SOLUTIONS.

$320,000
1 Beds ⋅ 1 Baths
Welcome to the Village of Shadyside. One bedroom large luxury condo unit in the Corinthian Condo Building. Unit 422 comes with its own one-car temperature controlled parking space along with a large secure storage room. Second floor location with a large covered balcony for outdoor lounging and perhaps a grill for seasonal entertaining. Entrance embellishments include sizable coat closet and parquet flooring along with room for a welcoming table and lamp. Drop those groceries off in the fully applianced galley kitchen and attached pantry. Bright and roomy living/dining area. Primary bedroom with large walk-in closet and attached full bathroom. Summer time relaxing at the heated inground pool with clubhouse facilities for all your entertaining and pool house conveniences. Extraordinary shopping and dining abounds right outside the gates of Village of Shadyside. A must see to appreciate, please call to schedule your tour.

100 Denniston St Unit 422, Shadyside

Listing courtesy of COLDWELL BANKER REALTY.

$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.

$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.

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