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$179,000
1 Beds ⋅ 1 Baths
Welcome to 400 S Highland Ave #10, a top-floor condo in the heart of Shadyside offering the perfect blend of convenience, comfort, and city living. Located just steps from some of Pittsburgh’s best shopping, dining, coffee shops, and nightlife, this home places you in one of the city’s most sought-after neighborhoods. Inside, you’ll find bright and inviting living spaces filled with natural light, a functional layout, and elevated views from the top floor that make the space feel open and airy. Designed for comfortable, low-maintenance living, the condo offers a practical flow ideal for both everyday living and entertaining. This prime location provides quick access to East Liberty, Bakery Square, downtown Pittsburgh, major hospitals, and nearby universities, making it an excellent option for professionals, students, or anyone seeking convenience and connectivity. If you’ve been searching for a condo in Shadyside with a great layout, top-floor views, and walkability to everything the neighborhood has to offer, 400 S Highland Ave #10 is an opportunity you won’t want to miss.

400 S Highland Ave Unit 10, Shadyside

Listing courtesy of COMPASS PENNSYLVANIA, LLC.

$649,000
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.

$356,500
3 Beds ⋅ 2 Baths
NEW PRICE – $356,500! Own for Less Than Rent! Charming 3-Bedroom, 2 bathrooms Condo in the Heart of Shadyside – Just Steps from Walnut Street! Don't miss this opportunity to own a beautiful Shadyside condo in one of Pittsburgh's most sought-after neighborhoods. Enjoy walkable access to Walnut Street's renowned restaurants, boutiques, coffee shops, and entertainment while building equity instead of paying rent. This home may qualify for the PHFA K-FIT Program, providing eligible buyers with valuable down payment assistance and reducing upfront homeownership costs. Qualified buyers may be eligible for: * Up to $17,500 in forgivable PHFA K-FIT down payment assistance * Estimated buyer cash needed at closing of approximately $14,500–$16,500 * Estimated monthly housing cost of approximately $2,850, including: * Principal * Interest * Property Taxes * Homeowners Insurance * HOA Fee Property Highlights * 3 Bedrooms * 1 and 1/2 Bathrooms * Prime Shadyside Location * Steps from Walnut Street shopping, dining, and entertainment * HOA Fee of just $182 per month * Potential PHFA K-FIT assistance available for qualified buyers Why rent when you can own and build equity? PHFA eligibility requirements and income limits apply. All financing assistance, monthly payment estimates, and cash-to-close estimates are subject to buyer qualification, lender approval, interest rates, taxes, insurance costs, closing costs, and program availability.

940 Bellefonte St, Shadyside

Listing courtesy of THE GREENE REALTY GROUP.

$329,900
2 Beds ⋅ 1 Baths
Welcome to this newly renovated 2-bedroom, 1-bath condo ideally located in the heart of Shadyside just steps from everything Shadyside has to offer! This move-in ready second floor unit combines modern updates with convenient city living. Inside, you’ll find a beautifully updated kitchen and bathroom featuring new cabinetry, counters, fixtures, and flooring. The functional layout offers comfortable living spaces along with a private Juliette balcony off the second bedroom and an additional rear deck accessed directly from the kitchen — perfect for relaxing or enjoying morning coffee outdoors. The primary bedroom is sizable and includes a walk-in closet! With a nice open floor concept, updated living room fireplace, new light fixtures, spacious rooms, tall ceilings, central AC, and large closets, this condo checks all the boxes. Additional highlights include dedicated off-street parking space #11, private enclosed storage locker #4, and access to the building’s common laundry room and bike storage room. The HOA also allows for rentals and pets. The HOA fee includes water, sewer, trash, common area maintenance, and snow removal. The unit owner is responsible for gas and electric only. Situated just one block from Walnut Street’s popular restaurants, coffee shops, boutiques, nightlife, and everyday conveniences, this condo offers an exceptional opportunity to enjoy one of Pittsburgh’s most walkable and sought-after neighborhoods.

5611 Elmer Street Unit 202, Shadyside

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

$370,000
2 Beds ⋅ 2 Baths
Located in the heart of Shadyside, this beautifully updated 2-bedroom, 2-bath condo offers stylish living with an unbeatable location. Step inside to stunning LVP flooring that flows throughout the bright and spacious living area. The updated kitchen features stainless steel appliances, white marble countertops, and abundant cabinet space, with convenient in-unit laundry just off the kitchen. The versatile living space also includes a dedicated dining area and bonus sitting space, perfect for a home office or reading nook. Down the hall, the spacious primary suite offers great natural light and an en suite bath complete with a walk-in shower and modern white vanity. A generously sized second bedroom with excellent closet space and a second full bath complete the home. The building includes one assigned parking space and offers fantastic shared indoor and outdoor common areas for residents to enjoy. Conveniently located near shopping, dining, and all that Shadyside has to offer, this condo is move-in ready and full of charm.

5825 5th Ave Unit 314, Shadyside

Listing courtesy of RE/MAX SELECT 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.

$290,000
1 Beds ⋅ 1 Baths
Charming and full of character, this spacious two-story, one-bedroom condo in the heart of Shadyside offers the perfect blend of style and convenience. Featuring hardwood floors throughout, soaring high ceilings, and stunning original woodwork and trim, the home is filled with warmth and tons of natural light. The generous living room showcases a beautiful decorative fireplace and opens to a private balcony—ideal for relaxing or entertaining. The updated kitchen is complete with white cabinetry and new sleek quartz countertops. Upstairs, you’ll find a versatile loft space perfect for additional living or a flex area, along with a large bedroom featuring a skylight and custom closet. A full bath and dedicated office space complete the upper level. Additional amenities include off-street parking, onsite laundry, and a private storage locker. Ideally located just steps from Walnut Street’s shops and restaurants, Mellon Park, and major hospitals and universities—this is city living at its best. **Second floor has exterior hallway access for moving/day to day purposes w/out using spiral staircase**

5321 5th Avenue Unit 5, 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.

$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.

$180,000
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. Ideally located, you’ll enjoy close proximity to Carnegie Mellon University and The University of Pittsburgh while also being close renowned hospitals, popular dining spots, and vibrant local shopping in Shadyside. Some standout features of this unit in particular are the south-facing windows which provide great natural light, parkay wood floors in the bedroom, and great placement for laundry. Everything you need is just minutes from your door! Amberson Towers delivers a full-service lifestyle with exceptional amenities, including 24/7 security, a well-equipped fitness center with streaming TV, a spacious party room, guest suite, library, and convenient laundry facilities on eight of the nine floors. Residents also benefit from a fully staffed management office with an on-site property manager—an advantage that sets this building apart. Parking options include three levels of indoor garage spaces (available for a fee) along with limited outdoor parking. The monthly HOA fee provides outstanding value, covering all utilities, building maintenance, and security.

5 Bayard Rd Unit 207, Shadyside

Listing courtesy of COMPASS PENNSYLVANIA, LLC.

$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.

$479,672
3 Beds ⋅ 2 Baths
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.

$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.

$320,000
2 Beds ⋅ 2 Baths
Welcome to stylish city living in the heart of Shadyside, where vibrant shops, acclaimed restaurants, and cultural institutions are just a short stroll from your door. This move-in ready residence blends comfort and modern design with thoughtfully upgraded designer features throughout. Step inside to discover an airy living space highlighted by dramatic double-story windows that flood the home with natural light. Textured plaster walls and curated designer light fixtures add warmth and sophistication, creating a refined yet inviting atmosphere. The home offers two well-appointed bedrooms and an updated full bath featuring custom tile, along with a convenient half bath on the main level—perfect for guests. Everyday living is made easy with the added convenience of an in-unit washer and dryer. Outside, a charming brick walkway with elegant planters leads to the building’s attractive lobby with a soaring ceiling, offering a welcoming first impression. The property also includes a designated, deeded parking space in the integral garage, plus guest parking directly in front of the building. With rentals and pets permitted, this home offers flexibility and an exceptional opportunity to enjoy one of Pittsburgh’s most desirable neighborhoods in style.

325 S Highland Ave Unit 103, Shadyside

Listing courtesy of BERKSHIRE HATHAWAY THE PREFERRED REALTY.

$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.

$399,000
2 Beds ⋅ 2 Baths
Stunning contemporary condo with 3 story dining area with a magnificent sky light and balcony. Open floor plan. 3rd floor accesses the roof top patio area and common area. Architectural masterpiece designed by the famous Arthur Lubetz* Wood burning fireplace in living room. In unit laundry area. **Steps to Universities, Hospitals and shopping areas and restaurants.** Secure parking garage with elevator to unit floor. Private storage area. Rooftop views are spectacular.

5030 5th Ave Unit 213, Shadyside

Listing courtesy of KELLER WILLIAMS STEEL CITY.

$185,000
1 Beds ⋅ 1 Baths
Welcome to Unit 621 at Amberson Towers — a beautifully updated one-bedroom, one-bath condo in the heart of Pittsburgh’s desirable Shadyside neighborhood. The thoughtfully renovated kitchen and bath create a move-in-ready space that is both comfortable and stylish. Custom-built closets throughout maximize storage and functionality. The open-concept living and dining area is filled with natural light from oversized windows that provide wonderful views and a bright, airy feel. The bedroom is generously sized, also featuring a large window and abundant natural light — a comfortable and peaceful retreat. Unit is on the end of the hall, very private and quiet. The location couldn’t be more convenient. Whether you work/attend UPMC, Carnegie Mellon University or University of Pittsburgh, or simply enjoy being close to parks, restaurants, and cultural attractions, everything is just steps away. Public transportation is right outside your door. (This building is just around the corner from Shady Side Hospital and Hillman ) Tired of circling the block or worrying about parking tickets? Garage parking is available in the building for just $93 per month — a perfect, stress-free solution for city living. The HOA fee includes ALL UTILITIES: water, sewer, heat, electricity, and insurance for the common areas. Residents enjoy a newly renovated fitness center, a party room, laundry facilities on every floor, and even a guest suite available to rent when (too many) friends or family come to visit. Walkable, convenient, and easy — this is Shadyside living at its best.

5 Bayard Rd Unit 621, Shadyside

Listing courtesy of RE/MAX SELECT REALTY.

$1,350,000
Amazing and Fabulous opportunity to live in the main house of 2 bedrooms and 3 full baths and lease the top floor for income. Main floor has an open floor plan allowing for a formal living room, dining room, and a family roomm with custom builtins, a full bath and a huge walk-in storage closet. The kichen has great prep space, pantries, and island with seating for 4. Totally renovated hroughout all floors. Light streams through every level. Newer mechanics, bathrooms, builtins, roof, etc. Enjoy a balcony off the primary suite and the rear covered terrace with awning. Gardens have abundant perrenials for seasons of beauty and space for the grill. Top floor apt has 2 bedooms with a full bath (two sink areas), open floor plan for living and dining areas. A full kiitchen with great cabinetry/storage, sky lights, and a balcony leading from the living space allows for lots of enjoyment throughout the seasons. 2nd floor laundry in main house and a basement laundry for tenants. Separate entrance on the side for the apt, with separate utilities. First floor access to stairs for the apt. Make it a single family residence....Add a 2nd floor doorway on the landing. Welcome to a lifestyle of luxury, with the location as well.

918 S Aiken Avenue, 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.

$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.

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