Shadyside Real Estate

Shadyside Real Estate

Welcome to Shadyside, a vibrant neighborhood nestled in the heart of Allegheny County, Pennsylvania. Known for its charming tree-lined streets and eclectic mix of historic and modern architecture, Shadyside offers a unique blend of urban convenience and suburban tranquility. This delightful area is a haven for those who appreciate a strong sense of community, cultural diversity, and an abundance of amenities.

Shadyside is renowned for its bustling commercial districts, where you’ll find an array of boutique shops, trendy cafes, and gourmet restaurants that cater to every palate. Whether you’re in the mood for a cozy brunch at a local eatery or a night out at an upscale dining spot, Shadyside has something to satisfy every craving. The neighborhood is also home to several art galleries and theaters, making it a cultural hub that attracts residents and visitors alike.

Outdoor enthusiasts will appreciate the proximity to beautiful parks and green spaces, perfect for leisurely strolls, picnics, or simply enjoying the fresh air. With its strong sense of community, Shadyside hosts various events throughout the year, including farmers' markets and seasonal festivals, fostering connections among residents and creating an inviting atmosphere.

Families are drawn to Shadyside for its excellent schools and safe environment, making it an ideal place to raise children. With easy access to public transportation and major highways, commuting to downtown Pittsburgh and beyond is a breeze.

In Shadyside, you’ll find not just a place to live, but a vibrant lifestyle waiting to be embraced. Discover the charm and allure of this exceptional neighborhood today!

Newest Listings in Shadyside

$499,999
3 Beds ⋅ 2 Baths
928 Bellefonte is one of just two units with a front yard in this classic 1935 Shadyside building. In a community where most units step directly off the sidewalk, this one is set back — private front yard, mature landscaping, columned portico, brick path leading to the door. It's a condo that lives like a townhouse, with its own street entrance and none of the shared-hallway energy. It's also one of only two units with a bow window, filling the home with light most units simply don't get. Inside, the 1935 craftsmanship is everywhere: hardwood floors, thick baseboards, crown molding in every room, and cove ceilings on the main floor. French doors open from the living room into a den with a decorative fireplace, a room that shifts easily between home office, reading nook, or whatever you need it to be. The kitchen was completely gut-renovated in November 2024 — layout reworked, every finish chosen with intention. Quartzite countertops, gas range, stainless steel appliances, subway tile backsplash, glass-front cabinetry, slate tile floors. Three bedrooms upstairs, all with soft colors and gorgeous floors, all with generous closets, including a walk-in. The full bath, renovated in 2022, has a double vanity and penny tile floors. And the powder room, also renovated in 2024, is forest green floor to ceiling, with a selfie-worthy tortoiseshell mirror. Parking is on-street, but in a permit zone, which means a spot right out front is available more often than not. It's the kind of trade Shadyside living tends to reward: give up the driveway, gain the walk. So, then there's Walnut Street, a 2 block walk away. Yoga, coffee, salons, banking, dinner. Everything you need whether it's Friday night or Monday morning. Condo living, townhouse vibes, Shadyside at its most walkable.

928 Bellefonte Street, Shadyside

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

$299,000
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.

$650,000
4 Beds ⋅ 3 Baths
Nestled in the heart of Pittsburgh's coveted Shadyside neighborhood, this beautiful home built in the 1900's offers the rare combination of historic charm, generous living space, and endless potential. For buyers who appreciate craftsmanship you simply can't replicate today, this home showcases an impressive collection of original architectural details, including four decorative fireplaces, intricate wood moldings, pocket doors, stained and leaded glass windows, beautifully preserved hardwood floors, and original polished door hardware. The welcoming main level features a spacious, flowing floor plan that's ideal for everyday living or entertaining, highlighted by custom built-in bookshelves and abundant natural light. Step onto the inviting covered front porch to enjoy the neighborhood's tree-lined streets, or retreat to the private rear courtyard, an intimate outdoor space ready for gardening, relaxing, or hosting friends. Upstairs, the expansive third floor offers incredible flexibility as a future primary suite, guest retreat, home office, or multi-generational living space. While the home presents an opportunity for thoughtful updates, its exceptional bones and preserved character provide the perfect canvas for those looking to blend historic elegance with modern design. Located just blocks from Walnut Street, Ellsworth Avenue, and the East Liberty Pedestrian Bridge, you'll enjoy easy access to some of Pittsburgh's best restaurants, boutiques, coffee shops, parks, and cultural attractions. This is more than a home, it's an opportunity to own a piece of Shadyside history and create a space that reflects your personal style while honoring its timeless character. If you've been searching for a historic Shadyside home with original woodwork, classic Victorian architecture, walkability, and room to make it your own, this exceptional property is one you won't want to miss.

5920 Alder St, Shadyside

Listing courtesy of COLDWELL BANKER REALTY.

$650,000
5 Beds ⋅ 3 Baths
Built in 1902, this three story Shadyside Victorian surprises at every turn. Larger than it appears from the street, the home unfolds across five bedrooms and two and a half bathrooms, with a level of original architectural detail that stops people in their tracks. From the moment you step inside, the craftsmanship is extraordinary. Original Eastlake millwork graces the principal doorways with intricate fretwork transoms, ornate spindlework, and geometric latticework that speak to a level of artistry rarely seen in modern construction. Richly carved newel posts, turned balusters, bracketed stair stringers, and substantial wood casings run throughout in remarkably preserved condition. Decorative fireplaces anchor nearly every room, and large windows flood the interiors with natural light. Art glass windows add quiet elegance in select rooms, while a colorful stained glass transom as you enter the sunroom is a genuine showstopper. Period-appropriate brass and frosted glass light fixtures cast a warm glow throughout, from the scrollwork chandelier in the living room to the delicate globe pendants in the dining room and the etched glass fixture gracing the upper hallway. This is a home that rewards every glance. The floor plan flows naturally and graciously. A welcoming living room opens to a formal dining room, creating an ideal space for gathering and entertaining, both graced with beautiful hardwood floors. A light-filled sunroom off the living room, modernized with skylights, is an irresistible retreat for morning coffee, reading, or tending to a flourishing plant collection. A substantial family room, currently staged as a home office, features built-in shelves, glass door cabinets, and richly toned woodwork that make it one of the home's most compelling spaces. The thoughtfully modernized kitchen is both beautiful and functional, with upgraded cabinetry, quartz counters, stainless steel appliances, and a peninsula for casual seating. A side door off the kitchen opens to a covered stoop, a convenient everyday entrance and exit. A rare intact rear staircase connects the kitchen directly to the second floor, a charming and practical feature original to homes of this era. The five large bedrooms are thoughtfully distributed across two floors. The second floor offers three bedrooms and a full bathroom, while the entire third floor provides two additional bedrooms, a full bathroom, and a large walk-in closet, a private and flexible retreat with endless possibilities. A powder room on the main level adds everyday practicality, and the massive basement provides laundry facilities and exceptional storage. Shadyside is one of Pittsburgh's most walkable and sought-after neighborhoods, and this address puts the very best of it within easy reach. Centrally located between Highland Park, Frick Park, and Schenley Park, and walkable to Mellon Park, with some of Pittsburgh's finest cultural amenities and recreational opportunities nearby, the setting is as appealing as the home itself. Trader Joe's, Whole Foods, and Target are all a short walk away, as is the new Meridian development. Walnut Street, Ellsworth Avenue, South Highland Avenue, and Bakery Square offer some of Pittsburgh's best dining, shopping, and everyday conveniences, all within easy reach. Add Carnegie Mellon University, the University of Pittsburgh, UPMC, and Pittsburgh's booming tech corridor to the mix, and the location speaks for itself. A stroll through the neighborhood is a walk through Pittsburgh history, where tree-lined streets and beautifully preserved historic homes reflect a community that has always taken pride in where it lives. This is Shadyside living the way it was meant to be.

6313 Kentucky Ave, Shadyside

Listing courtesy of RE/MAX REAL ESTATE SOLUTIONS.

$179,900
1 Beds ⋅ 1 Baths
Welcome to this beautifully updated 1-bedroom, 1-bath condominium in the iconic Amberson Towers, ideally located in the heart of Shadyside. At approximately900 sq. ft. this home offers one of the larger one-bedroom floor plans in the building. A rare open-concept kitchen—unlike the typical enclosed kitchens in other units—flows seamlessly into the spacious living and dining area, creating an open, inviting space perfect for everyday living and entertaining. Granite countertops, ample cabinetry, and updated appliances complete the modern kitchen. The living area is filled with natural light from two large windows, creating a bright and airy atmosphere that enhances the spacious feel of the home. The generously sized bedroom offers excellent closet space and comfort. The monthly HOA fee includes electricity, gas, heat, water, and sewer, providing exceptional value and truly low-maintenance living. Residents enjoy secure entry, 24/7 security, a fitness center, party room, guest suite, laundry facilities on every floor, a rooftop deck, outdoor patio, and additional storage. Garage parking is available for a monthly fee. Ideally situated just minutes from Carnegie Mellon University, the University of Pittsburgh, UPMC hospitals, Walnut Street shopping and dining, parks, and public transportation, this move-in-ready home offers the perfect combination of space, convenience, and maintenance-free living in one of Pittsburgh’s most desirable neighborhoods.

5 Bayard Rd Unit 706, Shadyside

Listing courtesy of YOUR TOWN REALTY LLC.

$329,000
2 Beds ⋅ 2 Baths
Prime Shadyside Location! Two-bedroom, two-bath, garden condominium located in prime Shadyside area! The primary bedroom features a walk-in closet and an en-suite bathroom. The second bedroom is well-proportioned and has ample natural light. The open-concept living area seamlessly flows into the kitchen, which is equipped, ample counter space and cabinet space. Hardwood vinyl floors throughout the main living areas provide a warm and inviting ambiance. The unit includes a storage, washer and dryer, 1 car integral garage for added convenience.

605 Shady Ave Unit A-5, Shadyside

Listing courtesy of COLDWELL BANKER REALTY.

$339,000
2 Beds ⋅ 2 Baths
Welcome to "Fairytale City Living" in a STUNNINGLY LARGE 2Bed/2Full Bath, 1253ft.², MOVE-IN-READY and beautifully sophisticated Open-Floor-Plan with private balcony in coveted SHADYSIDE where you walk to universities, hospitals, offices, cultural centers, fitness/yoga , amazing restaurants & shopping where you will never need a car! You are greeted with expansive wall to wall windows (some floor to ceiling) drenching the huge living and dining room with natural light. The modern kitchen has been updated with granite, stainless steel appliances, richly finished cabinetry, stylish backsplash and bar area. This home offers an incredibly large owner's suite with a generously sized bath, exceptional walk-in closet, and more wall to wall windows to view the lush foliage that spans the entire home. The oversized light filled secondary bedroom has a nicely tiled full bathroom across the hall making it convenient for your guests. You will find abundant storage throughout this luxury condo. Maintenance Free City Living At It's Finest! Will Not Last Long! Schedule Your Tour Today:))

5619 Kentucky Ave Unit 202, Shadyside

Listing courtesy of KELLER WILLIAMS EXCLUSIVE.

$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.

$210,000
1 Beds ⋅ 1 Baths
All that Shadyside has to offer, literally at your doorstep. Welcome to Shady Court Condominiums. This nicely updated ground floor condo located in the heart of one of Pittsburgh's most desirable neighborhoods! This 1-bedroom, 1-bathroom home puts you minutes from the quintessential Shadyside experience. Enjoy the Main Street USA feel that offers easy access to Pitt, CMU and other area universities, as well as both UPMC and West Penn Hospital Systems. The inviting open layout is highlighted by sleek flooring throughout, creating a sense of flow between the spaces. The kitchen is fully equipped with stainless steel appliances, granite countertops and breakfast bar, making meal prep and casual dining a breeze. You'll also enjoy the added convenience of in building laundry and secure entry. The coffee shops, bars, restaurants and top notch retail experience that have defined Shadyside for decades begins just down the block to your left. Turn to your right and you'll find the newest Commonplace Coffee location. Whether you’re a first-time buyer, rightsizing, or looking for a city retreat, this property offers a wonderful combination of convenience and style. This is a rental friendly building. Don’t miss out on this fantastic opportunity—schedule your showing today!

5708 Walnut Street Unit G-1, Shadyside

Listing courtesy of COMPASS PENNSYLVANIA, LLC.

$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.

$200,000
1 Beds ⋅ 1 Baths
Beautifully renovated 1-bedroom, 1-bath condominium in the heart of Shadyside! This move-in-ready condo combines modern updates with low-maintenance living in one of Pittsburgh's most sought-after neighborhoods. The bright, inviting interior features stylish finishes and a functional layout designed for everyday comfort. Luxury vinyl plank flooring, renovated kitchen and bath. Ideally located just minutes from UPMC hospitals, the University of Pittsburgh, Carnegie Mellon University, and Chatham University. Perfect for medical professionals, faculty, students, or anyone seeking an exceptional location. Enjoy being just steps from Shadyside's boutique shopping, popular restaurants, cafés, parks, and public transportation, with easy access to Oakland, Downtown Pittsburgh, Bakery Square, and major roadways.

5825 5th Ave Avenue Unit 310, Shadyside

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

Start Your Search

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