View All Fox Chapel PA Luxury Homes Listings

This exceptional 4 bedroom Fox Chapel Borough home is ideally located on coveted Windsor Road, a quiet and charming street surrounded by one of the area’s most architecturally interesting neighborhoods. 39 Windsor Road enjoys a premier position with timeless curb appeal, a spacious turnkey interior, unforgettable character and unexpected surprises throughout. Gorgeous hardwood floors flow throughout the first floor featuring a classic living room and dining room. A lovely sitting room with built in bookshelves and doors leading to the private covered porch with awning. The sprawling eat in kitchen is truly a cook’s dream with loads of cabinetry, abundant counter space, a huge center island, double ovens, gas range and a built in desk area perfect for staying organized or for a convenient home work area! The kitchen is open to the inviting family room with a gas-log fireplace, builtin bookshelves and there are walls of windows with private views and doors leading to the deck and grilling area making entertaining effortless. The second floor offers a tremendous floor plan with four spacious bedrooms and three full bathrooms including the primary suite with a walk in closet. All bedrooms offer roomy closet space and wonderful natural light. A walk up third floor area provides excellent attic storage too. The finished lower level is a wonderful surprise with a large gameroom, extensive storage, a utility room and tool bench area. You'll love the bright and light dedicated laundry room and mudroom area. Also there is a full bathroom and direct access to the level driveway and the spacious two car garage. Beautiful professional landscaping and hardscape complete the property. An ideal location with quick access to Fox Chapel Area amenities, UPMC hospitals, Oakland, Downtown Pittsburgh, Fox Chapel area schools, Shadyside Academy, shopping, dining and more. Welcome Home!

39 Windsor Road, Fox Chapel

Listing courtesy of BERKSHIRE HATHAWAY HOMESERVICES THE PREFERRED REAL.

Selling Office: BERKSHIRE HATHAWAY THE PREFERRED REALTY.

$950,000

Perched above the Fox Chapel Golf Club, this architecturally distinctive home blends privacy, natural light, and thoughtful design. The main level is bright and open, featuring a spacious living room with a fireplace, a separate family room with a second fireplace, an elegant dining room, and a dedicated home office.The kitchen is equipped with a high-end JennAir gas range, granite island and countertops, and custom wood cabinetry with convenient pull-out shelving. Full-length windows and French doors throughout the first floor frame sweeping views of the surrounding landscape. There are four generously sized bedrooms on main level each include an en-suite bath. The primary suite stands out with its cathedral ceiling, walk-in closet, and private bath.The lower level adds exceptional flexibility with a full bath, abundant storage, and an open area ideal for work out space. A first-floor laundry with utility sink enhances everyday convenience. Long tandem integral garage can fit 3 cars Located in the top-rated Fox Chapel Area School District and minutes from parks, dining, and Downtown Pittsburgh.

231 Fairview Rd, Fox Chapel

Listing courtesy of RE/MAX REAL ESTATE SOLUTIONS.

$930,600

621 Twin Pine Rd, Fox Chapel

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

$1,300,000

Welcome to 104 Wynnwood—an exceptional contemporary residence set on two private acres in the heart of Fox Chapel. Privately positioned behind a gated entrance, this beautifully updated home blends modern design with warm, livable spaces and standout amenities throughout. Freshly painted and move-in ready, the home welcomes you with a grand, light-filled entry that opens to an expansive and thoughtfully designed main level. The large dining room is both elegant and inviting, featuring French doors that lead directly to the outdoor patio—creating effortless indoor-outdoor flow for entertaining. The patio itself is a true extension of the home, complete with a built-in grill and ample space to gather, dine, and relax. At the heart of the home is a stunning gourmet kitchen featuring heated floors and a suite of top-tier appliances, including Wolf, Miele, and Sub-Zero. Granite countertops, abundant cabinetry, and a built-in breakfast nook with custom storage make this space as functional as it is beautiful—perfect for both everyday living and hosting. The living room is anchored by rich wood floors and a striking fireplace, while a separate cozy family room with its own fireplace offers a more intimate setting to unwind. A first-floor guest suite provides flexibility for visitors or multigenerational living. Just inside the garage entry, a custom built-in cubbie system keeps daily life organized with ease. Upstairs, the primary suite is a true retreat—exceptionally spacious with room for a private sitting area or home office. The ensuite bathroom offers comfort and style, complemented by an impressive wall of built-in closets and a large walk-in closet featuring a center island for added storage and convenience. Two additional generously sized bedrooms share a well-appointed hall bathroom with heated floors, adding a touch of everyday luxury. Additional highlights include a heated garage with an epoxy floor, as well as a whole-house generator for peace of mind. The beautifully maintained two-acre setting enhances the home’s sense of privacy and tranquility while remaining just minutes from everything Fox Chapel has to offer. Offering a rare combination of contemporary style, high-end finishes, and exceptional indoor-outdoor living, 104 Wynnwood is a standout property in one of the region’s desirable communities.

104 Wynnwood Dr, Fox Chapel

Listing courtesy of BERKSHIRE HATHAWAY THE PREFERRED REALTY.

Privately set at the end of a long, winding driveway, this exceptional all-brick estate stands on two picturesque acres in the heart of Fox Chapel—one of Pittsburgh’s most prestigious and sought-after communities. Offered for the first time in more than 55 years, it is defined by privacy, presence, and enduring architectural elegance. Built in 1935, the residence showcases a richly detailed living space filled with original hardwood floors, custom millwork, decorative ironwork, and classic craftsmanship. A grand foyer welcomes guests with a sweeping curved staircase and wrought-iron railings, setting the stage for an impressive yet inviting entertaining atmosphere. Light-filled formal and casual rooms create an inviting flow throughout the main level, including a distinguished dining room framed by floor-to-ceiling French doors. Charming fireplaces, architectural nooks, and thoughtful design give each space warmth and character. Five spacious bedrooms and three-and-a-half baths provide comfort and flexibility across the upper levels, complemented by a finished lower level offering additional recreation and storage. A full third floor remains available for future personalization to suit modern needs. This estate has been meticulously maintained with significant investments in infrastructure, including updated electrical with the removal of knob and tube wiring, a new underground electrical service line, a new sewer line, slate roof restoration, added central air conditioning, and numerous plumbing enhancements. Exterior improvements include corrected foundation grading, repaired downspouts and sprinkler system, and a newer gravel driveway. Positioned within the top-rated Fox Chapel Area School District and just minutes from local amenities, parks, and Downtown Pittsburgh, this residence offers a rare blend of tranquility, heritage, and convenience. A truly generational property—ready to continue its legacy with its next proud steward.

$1,605,750

5 Beds ⋅ 4 Baths

470 Fairview Rd, Fox Chapel

Listing courtesy of COLDWELL BANKER REALTY.

Selling Office: BERKSHIRE HATHAWAY HOMESERVICES THE PREFERRED REAL.

$1,399,000

5 Beds ⋅ 4 Baths

Completely reimagined from top to bottom, this exceptional property blends refined luxury with thoughtful design and architectural character. Offering 5 bedrooms, 3.5 baths, and a 2-car garage, every inch of this home has been meticulously remodeled with high-end materials and custom craftsmanship throughout. A stunning main-level owner’s suite serves as a true retreat, featuring vaulted ceilings, a dramatic two-story stone fireplace, and direct access to a private deck, creating a seamless indoor-outdoor connection. The suite is complemented by a spa-inspired bath with heated floors, Carrera marble surfaces, handcrafted Zellige tile, champagne bronze fixtures, and beautifully designed inset cabinetry. The heart of the home is the architecturally designed kitchen, showcasing Taj Mahal natural stone countertops, European-style Rift Sawn white oak cabinetry, and a Fisher & Paykel appliance package with integrated refrigerator and dishwasher. A workstation sink and designer fixtures elevate both everyday living and entertaining. Throughout the main level, wide-plank European white oak flooring, solid wood interior doors, and curated lighting create a warm yet sophisticated aesthetic. A custom white oak staircase adds to the architectural detail, while the atrium space blends modern design with character through exposed brick and steel elements. Multiple living areas, including a living room with a secondary fireplace, offer both comfort and flexibility. The renovation extends far beyond the visible finishes, with all new aluminum-clad windows and doors, a new architectural roof with standing seam metal accents, two new HVAC systems, updated insulation, and enhanced mechanical systems including a recirculating hot water system for near-instant hot water. Additional highlights include beautifully updated secondary bathrooms with marble finishes, a stylish powder room with herringbone marble flooring, and thoughtful touches throughout that reflect both quality and intention. Set on professionally landscaped grounds with mature plantings, architectural urns, and designer exterior lighting, this home offers a rare combination of luxury, comfort, and craftsmanship - truly move-in ready and designed to stand apart.

90 Chapel Ridge Place, Fox Chapel

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

$1,300,000

Welcome to 100 Forest Drive located on a lovely level cul de sac street in the highly desirable Fox Chapel Borough within the Fairview Elementary School zone. This beautifully maintained 4 bedroom, 4.5 bath home offers a wonderful blend of classic charm, comfortable living spaces and a picturesque setting with exceptional outdoor appeal. The inviting floor plan is designed for both everyday living and entertaining with a gracious flow between rooms and an abundance of natural light throughout. The kitchen is warm and welcoming with a spacious eat in area, generous counter space, abundant cabinetry and is open to the family room creating a seamless space for gathering. From here, step out to a private deck overlooking the scenic grounds, perfect for morning coffee, dining outdoors or relaxing in a peaceful setting. The main level also features a formal dining room ideal for hosting, multiple sitting areas for flexible living, a convenient first floor office and a desirable first floor bedroom offering excellent options for guests or additional work from home space. Upstairs you will find a spacious and impressive primary suite with a large walk in closet and incredible views of the grounds, creating a true retreat. The additional bedrooms are generously sized with roomy closet space and access to a well appointed full bathroom on the second floor. The exterior setting is truly special with mature landscaping, beautiful plantings, play areas, and a huge shed for storage Located in the heart of Fox Chapel with easy access to parks, trails, shopping and amenities as well as a convenient commute to downtown Pittsburgh, Oakland and major medical centers. A wonderful opportunity to own a move in ready home in a premier location.

100 Forest Drive, Fox Chapel

Listing courtesy of BERKSHIRE HATHAWAY HOMESERVICES THE PREFERRED REAL.

$1,206,250

Set on a beautifully maintained homesite along a private road in Fox Chapel, this expansive 4-bedroom, 5-bath residence offers timeless design, refined finishes, and a layout tailored for both elevated everyday living and seamless entertaining. Surrounded by established homes and mature landscaping, the setting offers a sense of privacy while remaining well positioned near parks, dining, and everyday amenities. Located within the Fox Chapel Area School District. A desirable 3-car attached garage and a private, usable backyard complete the offering. A grand two-story entry sets the tone, anchored by a formal stairwell and flanked by a well-proportioned livingroom and an elegant dining room featuring a tray ceiling. The home unfolds into a spacious kitchen that serves as the central gathering point, effortlessly connecting to the main living areas. Designed with both functionality and presentation in mind, the kitchen features abundant cabinetry, granite countertops, and a bright eat-in area that opens to the dramatic two-story great room. Soaring ceilings, skylights, and a wall of windows create an airy, light-filled atmosphere, while a built-in wet bar and direct access to the patio enhance the home’s entertaining potential. A private study provides a sophisticated work-from-home environment, complete with floor-to-ceiling judge’s paneling and access to its own deck overlooking the backyard. The main level also includes a full bath, along with a well-appointed laundry room and mudroom for everyday convenience. Upstairs, hardwood flooring continues throughout all bedrooms and extends across much of the main level. The primary suite is thoughtfully designed with vaulted ceilings, French doors, oak flooring, a generous walk-in closet, and a spacious bath featuring a soaking tub, separate shower, and skylight. Secondary bedrooms are all well-sized with excellent storage and hardwood flooring. The lower level expands the home’s versatility with a finished game room, an exercise or flex space, a full bathroom, and ample storage. Additional highlights include the three-car garage, a classic brick exterior, and a level rear yard with a large patio designed for outdoor living and entertaining, with convenient access to main roads and an easy commute to the city.

910 Settlers Ridge Road, Fox Chapel

Listing courtesy of RE/MAX SELECT REALTY.

Selling Office: BERKSHIRE HATHAWAY THE PREFERRED REALTY.

$1,800,000

Nestled on a charming, tree-lined road in one of Fox Chapel's most beloved neighborhoods, this beautifully appointed residence blends timeless architecture with modern, livable elegance. From the moment you arrive, the home’s character is undeniable—classic curb appeal, thoughtful landscaping, and a welcoming presence that sets the tone for what’s inside. Step through the front door to discover a light-filled interior where original details and tasteful updates exist in perfect harmony. Rich hardwood floors, graceful moldings, and well-proportioned rooms create an effortless flow, ideal for both everyday living and entertaining. The living room, located just off the entryway, features a distinctive sunken design with oak hardwood floors, a wood-burning fireplace with a convenient gas starter, and custom built-in shelves and cabinetry—all complemented by expansive windows that fill the space with abundant natural light. At the center of the home is a beautifully designed chef’s kitchen, featuring Cambria quartz countertops, a professional-grade Wolf gas range with double wall ovens, and a Sub-Zero refrigerator and freezer with custom panels that seamlessly blend with the cabinetry. A custom stainless steel hood with pot filler anchors the space, while a butcher block island with prep sink and hanging pot rack adds both warmth and function. A farmhouse sink overlooks the backyard, and the kitchen opens to a stunning vaulted dining area with built-in seating, a wood-burning fireplace, and a pizza oven—creating an inviting space with seamless access to the patio and garden. The formal dining room, ideally situated between the living room and kitchen, showcases original painted pine wood floors, a cozy gas fireplace, and custom built-in shelving, all enhanced by a large window that fills the space with natural light and offers serene views of the pond. Upstairs, 4 spacious bedrooms offer comfort and retreat, while the primary suite provides a serene escape with refined touches and generous storage, a guest suite and 2 additional bedrooms with an additional hall bath is updated with clean, classic finishes that stand the test of time. A well-appointed first-floor laundry room offers abundant storage, a second dishwasher, an ice machine, and direct outdoor access for everyday convenience. The unfinished lower level features high ceilings, a half bath, generous storage, and dedicated gym space, while three HVAC systems and an attic-mounted whole-house ventilation fan ensure year-round comfort. Outside, a private backyard oasis provides the perfect setting for quiet mornings or lively evenings—an extension of the home’s warm and inviting atmosphere. Whether hosting friends or enjoying a peaceful moment, this outdoor space is designed to be enjoyed. Located just minutes from Pittsburgh’s downtown area cultural destinations, Shadyside restaurants and hospitals, this home offers not only beauty and comfort, but also the convenience of city living with a true neighborhood feel.

321 Fairview, Fox Chapel

Listing courtesy of BERKSHIRE HATHAWAY THE PREFERRED REALTY.

Selling Office: BERKSHIRE HATHAWAY THE PREFERRED REALTY.

$1,325,000

Tucked within one of Fox Chapel’s most desirable neighborhoods, 76 Fair Oaks Dr offers a refined blend of classic architecture and comfortable everyday living. A striking marble entry with a sweeping curved staircase creates an impressive first impression, leading into well-appointed living spaces designed for both entertaining and relaxation. The formal living room showcases custom built-ins and a timeless fireplace, while the richly detailed library—complete with floor-to-ceiling shelving and a granite-accented fireplace—provides a warm, inviting retreat. Natural light pours through elegant Palladian windows, brightening the spacious family room anchored by a brick fireplace. The eat-in kitchen is thoughtfully equipped with quartz countertops, a new cooktop, double ovens, and abundant cabinetry, seamlessly connecting to the home’s main living areas. A first-floor laundry room adds everyday ease. Upstairs, the primary suite offers a true retreat with its own fireplace and dual walk-in closets. The finished lower level expands the home’s versatility with a generous game room, additional flex space ideal for a home office or guest room, and extensive storage including a cedar-lined closet. Set in a private, sought-after location, this home delivers timeless character, functional space, and lasting appeal.

76 Fair Oaks Dr, Fox Chapel

Listing courtesy of COLDWELL BANKER REALTY.

Selling Office: BERKSHIRE HATHAWAY HOMESERVICES THE PREFERRED REAL.

$1,790,000

Situated in one of Fox Chapel’s most coveted locations—just 1.3 miles to Shadyside Academy & Fox Chapel Golf Club—this exceptional property features two residences on 3.2 acres. The primary all-brick estate, custom built in 2000 by Madia Homes, offers approximately 7,000+ sq ft of finished space with soaring 10' first-floor ceilings, 5 bedrooms, 4.5 baths, 4 fireplaces, and a grand entrance split staircase with a two-story open foyer. The home includes a main-level 4-car garage, two private offices, marble flooring throughout the main level, and hardwood flooring throughout the second floor. Expansive unfinished areas present a rare opportunity to customize and expand living space. The basement is framed with heating, cooling, and electrical rough-ins in place, while the third floor remains open for future finishing. The attached original 1950s ranch includes 3 bedrooms, 2 full baths, a 2-car integral garage, and its own private driveway. While in need of renovation, it offers exceptional potential as a guest residence, au pair suite, extended family quarters, or additional living space. Situated on 3.2 acres, the property offers remarkable flexibility to create a private outdoor retreat with room for amenities such as an inground pool, sport courts, or outdoor entertaining spaces. The scale and layout of the estate offer exceptional flexibility for multi-generational living, extended family, or long-term guests. A rare opportunity to create a true legacy estate in one of Pittsburgh’s most sought-after neighborhoods.

1060 Fox Chapel Road, Fox Chapel

Listing courtesy of SIMPLIHOM.

$1,025,000

Welcome to 112 Hickory Hill Road in Fox Chapel Borough, ideally located on a cul de sac with scenic rear views and a large deck perfect for relaxing or entertaining. This classic five bedroom Colonial offers a wonderful floor plan with spacious rooms throughout. The first floor features a lovely living room and dining room, an eat in kitchen, an office and a family room with fireplace and doors out to the deck. A level driveway leads to the attached garage with entry into a convenient mudroom and first floor laundry. The home offers five spacious bedrooms with three full baths and abundant storage throughout. The lower level includes a bright game room with windows and door to outstide, an additional laundry room, a utility room and a half bath providing excellent space for recreation or guests. A level driveway leads to the attached garage with built in cabinetry for storage Great location close to all Fox Chapel amenities, schools and country clubs with convenient commute times to the city, UPMC hospitals, Oakland and more.

112 Hickory Hill Road, Fox Chapel

Listing courtesy of BERKSHIRE HATHAWAY HOMESERVICES THE PREFERRED REAL.

Selling Office: BERKSHIRE HATHAWAY THE PREFERRED REALTY.

$1,915,000

Set quietly back from the road on a private and well-manicured, tree-framed property in Fox Chapel, this 5-bedroom 4.5 bath luxury home blends timeless architecture with the kind of warmth that makes a house truly inviting! This home was built in 2009 by The Waldeck Group and is the perfect balance of being sophisticated but also expressive and well thought out. The primary suite is located on the main level and offers a sense of retreat with its vaulted ceiling, soft neutral tones, and large windows overlooking the grounds. The great room with its stone fireplace and gorgeous lighting is open and bright and walks out onto a beautiful terrace. The den is moody and classic with its custom cabinetry and gas fireplace and is a perfect cozy spot for a first-floor office or entertaining guests. The kitchen is spacious and light and offers a large granite island and rich hardwood flooring along with 2 dishwashers, 2 ovens and gas cooktop. A chef's dream. The laundry room finishes out the main level and is fantastic. Upstairs there are 3 bedrooms, one is currently used as an upstairs office space. There is even a huge secret storage space that could be finished as an additional bedroom or media room! The basement measures over 2000 sq. feet and has a full bath and a bedroom in addition to a large living area and home gym. The house has an attached garage and also an additional 2 car detached garage which could have many uses! The house sits on 1.4 completely fenced acres and has been cared for meticulously by a local landscaper. The gardens, foliage and perennials are mature and stunning! Minutes away from Fox Chapel High School and Shadyside Academy, feeds to Fairview Elementary School. Quick access to Rt. 28 and I-279, downtown Pittsburgh, Shadyside/Squirrel Hill, and shopping. This home has quiet sophistication and peaceful surroundings. The current owners have thoughtfully designed every inch and have incredibly maintained this home. A true gem in Fox Chapel Borough.

135 Greenwood Road, Fox Chapel

Listing courtesy of PIATT SOTHEBY'S INTERNATIONAL REALTY.

Selling Office: BERKSHIRE HATHAWAY HOMESERVICES THE PREFERRED REAL.

$1,600,000

A completely unique home beautifully poised among towering trees and lush perennial gardens with a water feature, offering indoor and outdoor living at it's absolute finest and defined by a mix of creative energy and vibrant atmosphere perfect for relaxing or entertaining. Seamlessly blending indoors and out, the home was intentionally designed to invite nature into everyday living while offering an atmosphere that is both inspiring and efforlessly welcoming. With a beautifully curated living space, the home offers 4 bedrooms, 4 full baths, and 4 garage spaces- perfectly balancing sophistication, comfort and flexibility for today's lifestyle. Expansive entertaining areas, intimate gathering spaces, and peaceful retreats throughout the property make every corner feel both functional and special. Ideally located just minutes from Shadyside Academy, Fox Chapel Area schools, the Lauri Ann West Community Center, Hillman Performing Arts, Cooper-Siegel Library, Beechwood Farms Nature Reserve, UPMC hospitals, multiple Fox Chapel hiking trails and Hartwood Acres, this home offers an unmatched lifestyle in one of Pittsburgh's most desirable communities. Designed for versatility, connection and everyday enjoyment, 337 Fox Chapel Road is more than a home- it's a destination unto itself.

337 Fox Chapel Road, Fox Chapel

Listing courtesy of RE/MAX SELECT REALTY.

$3,250,000

5 Beds ⋅ 7 Baths

Perfectly positioned in prestigious Fox Chapel—just minutes from Fox Chapel Golf Club, Pittsburgh Field Club, and Rt. 28—this extraordinary estate pairs timeless Georgian elegance with refined modern luxury. A gated courtyard introduces a stately façade and a breathtaking interior defined by soaring ceilings, inlaid marble, intricate millwork, and dramatic architectural columns. Truly a rare find. A grand entry and a striking floating staircase—enhanced by a rear staircase and private elevator—anchors the home. Designed for effortless entertaining, elegant formal spaces transition seamlessly, while a richly appointed library offers a quiet retreat. The chef’s kitchen showcases marble surfaces, premium appliances, and a fully equipped butler’s pantry in the center of the home. Great laundry room and full bath which services the pool area...idea for guests using the swimming pool. Upstairs, four spacious bedroom suites each feature their own fireplace. The stunning primary suite includes an incredible dressing room and spa-inspired marble bath with double vanities. A private apartment with separate entrance, kitchen, living area, bedroom, bath, and laundry provide ideal guest, in-law, or extended-stay accommodations. Four car tandem garage. Manicured grounds, multiple outdoor living areas, and a sparkling pool complete this rare opportunity to own one of Fox Chapel’s most distinguished estates

418 Fox Chapel Rd, Fox Chapel

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

Selling Office: BERKSHIRE HATHAWAY THE PREFERRED REALTY.

$1,850,000

Live in the heart of Fox Chapel on 6 acres. Coming from the city, feel free to walk to Aspinwall for delights in coffee shops, restaurants, a Spa, boutiques, and more.Get to downtown, Shadyside,Sq Hill, Cranberry, & the Turnpike with ease.History awaits you on all levels with light that streams trough all the day long.Updates to kitchen and bathrooms along with hardwood floors, side and rear patios, grilling porch off the kitchen, two staircases, mud rm, & a 12x5 temp controlled wine cellar. Bonus rm is used as an office, but can be a bedroom, if needed.Architecture of the 1920's defies the ordinary and has an appreciative value. Closet space is abundant on all levels. Bonus 8x7 nook in the kitchen is used as an office area for organizing the family acivities. A huge walk up top floor for gaming space and storage.Lower level has a walk in safe, bathroom, work room, storage, and a game room with a decorative fireplace. Enjoy the expansive lawn areas that surround the home, while the rear affords you privacy with specacular views and mature trees. Classic Tudor with todays floorplan and lifestyle needs in the award winning Fox Chapel School District. Welcome to what you have waited to find.

918 W Waldheim Rd, Fox Chapel

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

Discover the perfect canvas for your dream home on a premier 3-acre vacant lot. This prime piece of land offers an unmatched opportunity to build a custom residence tailored to your vision, surrounded by stunning natural beauty. Partner with Wade Weissman Architecture and Phillip Wentzel Custom Homes to bring your ideas to life, blending innovative design with superior craftsmanship. The lot is construction-ready, allowing you to take advantage of the endless possibilities it offers. Draft floor plans are available as a starting point, but you have the freedom to adapt and modify every aspect to suit your taste. This lot is more than just land; it's a chance to create a legacy that reflects your unique style and dreams. Don’t miss out on this rare opportunity to craft a one-of-a-kind residence on a premier Fox Chapel property, where luxury and limitless potential await.

$1,600,000

5 Beds

280 Glen Laurel Ln, Fox Chapel

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

$4,950,000

Welcome to your dream home opportunity nestled on a premier 3-acre lot. This custom residence offers an unparalleled chance to fully customize your ideal living space amidst breathtaking natural surroundings. Collaborate with Wade Weissman Architecture and Phillip Wentzel Custom Homes, where the fusion of innovative design and masterful craftsmanship brings your vision to life. With a site ready for construction, the possibilities are as endless as the panoramic views that surround you. Draft floor plans are prepared, offering a starting point for your creativity. Whether you choose to embrace these plans or prefer to tweak them to perfection, the power to shape every detail is in your hands. This is more than a home; it’s a legacy, a reflection of your unique style and aspirations. Don't miss this chance to turn your dreams into reality. Your future begins here, on this premier Fox Chapel lot, where luxury meets limitless potential.

280 Glen Laurel Ln, Fox Chapel

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

$2,195,000

Move right into this Fox Chapel home, set on a private, park-like lot that artfully blends modern luxury with timeless sophistication. Every element reflects exceptional craftsmanship and design. New Pella Reserve windows, French white oak floors, Italian marble, Restoration Hardware fixtures, and designer kitchen with custom cabinetry, Sub-Zero refrigerator, 48” Wolf range, and Bosch dishwasher. Additional highlights include a tankless water heater, Lennox HVAC with humidifier, two laundry areas, and a slate roof. A foyer with a sweeping staircase opens to light-filled living areas with a marble fireplace and exposed beams. The first floor offers an ensuite bedroom or office, the upper level features a primary suite with spa-inspired bath and guest rooms. The lower level includes a family room with fireplace and flex space. Enjoy outdoor living on the side porch and stone patio all in a prime location, minutes from local clubs, Shady Side Academy, the community center, and library.

129 South Drive, Fox Chapel

Listing courtesy of BERKSHIRE HATHAWAY HOMESERVICES THE PREFERRED REAL.

$2,800,000

5 Beds ⋅ 7 Baths

407 Rhodora Lane, Fox Chapel

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

$1,165,000

700 W Waldheim Road, Fox Chapel

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

$1,195,000

Stunning home situated on a large lot. Fenced in yard. Governers driveway. Large living room with plenty of natural light, fireplace and access to a side deck. Quaint family room with brick fireplace and sliding glass doors to the deck overlooking the backyard. Kitchen with updated appliances, island and breakfast nook. Oversized dining room with bay window and built in bookshelves. Also on the first floor is a spacious laundry room with access to the backyard, 2 half baths and lots of storage. Upstairs the owner's suite with 2 closets and large bath. Extra large bedroom over the garage with ensuite bath. Two nicely sized additional bedrooms and hall bath complete the 2nd floor. Finished walkout basement with media room, home office, half bath with rough in for shower and plenty of storage. Covered patio right outside the walkout basement.

907 Settlers Ridge Rd, Fox Chapel

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

Welcome to a luxury life style that is rare and defies the ordinary. Stone home situated on a spectacular 1+acre in the heart of Fox Chapel. Lovingly restored in a meticulous approach that is perfection. Access to the patios and professionally landscaped gardens from the dining room, great room, and kitchen make it perfect for gathering family, small groups or corporate style events. From work day needs, to fitness and fun, the space is there for it all. Craft room, billiard room, game room, and theatre make this all that one needs. Sought after location close to schools, shopping, golf, swim clubs, community center and library. Parks and trails throughout the community make life a vacation in all seasons.

$4,101,175

4 Beds ⋅ 8 Baths

134 South Dr, Fox Chapel

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

Enjoy year-round resort-style living with your own indoor pool, fully equipped fitness room, state-of-the-art movie theatre, and game room. The spacious layout offers multiple entertaining areas, elegant formal rooms, and a luxurious owner's suite retreat.

$1,900,000

6 Beds ⋅ 7 Baths

590 Old Mill Road, Fox Chapel

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

$1,020,000

Farmhouse-style home on 3+ acres, privately set in Fox Chapel away from the main road. Enjoy nature, privacy, and community. Main level features 2-car garage, family room with gas fireplace & sunny breakfast nook, chef’s kitchen with dual islands, concrete counters, Sub-Zero fridge, Wolf range, and ample cabinetry. Hardwood flooring throughout the home. Formal dining, spacious living room with fireplace, and all-season room—each with French doors to the outdoors. Ideal for entertaining! Large patio with hot tub, fenced yard, and space for a future pool in the larger upper flat yard. Upstairs: oversized primary suite with walk-in closets, dual-vanity bath, and private deck. Three more bedrooms and two updated baths. Lower level includes guest suite with en-suite bath, game room, and storage. Near Beechwood Farms & Fairview Elementary. ~20 mins to Bakery Square, Downtown, and Oakland. A rare blend of tranquility and convenience—perfect for nature lovers, and entertainers alike.

1258 Fox Chapel Rd, Fox Chapel

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

$1,870,000

240 Old Mill, Fox Chapel

Listing courtesy of BERKSHIRE HATHAWAY THE PREFERRED REALTY.

Introducing The Oberoi—Fox Chapel’s last great estate opportunity. Set on approximately 5 acres of untouched woodland in one of Pittsburgh’s most prestigious communities, this rare property offers unparalleled privacy and the chance to create a lasting legacy. Nestled within this extraordinary setting, Walden is a modern cottage-inspired residence blending timeless elegance with contemporary comfort. From the arched windows and stone-accented façade to the 2-story great room and gourmet kitchen, every detail exudes thoughtful luxury. A grand main-floor primary suite, formal dining, hearth room, and private guest apartment above the porte cochere add sophistication and flexibility. With space for extended family, work-from-home ease, and seamless indoor-outdoor living, The Oberoi is a unique opportunity to own what cannot be replicated—by private appointment only.

$4,770,000

4 Beds ⋅ 6 Baths

Walden The Oberoi Fox Chapel, Fox Chapel

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

$3,585,000

3 Beds ⋅ 3 Baths

Introducing The Oberoi—Fox Chapel’s last great estate opportunity. This rare offering includes approximately 5 acres of old-growth woodland in one of Pittsburgh’s most private, prestigious communities. A setting of extraordinary seclusion, yet just moments from the cultural, academic, and country club life that define Fox Chapel. Nestled within this legacy property, the Easton is a modern cottage-style home that blends classic charm with today’s functionality. A brick and shuttered façade opens to an airy, open layout perfect for entertaining, anchored by a cozy hearth room and fireplace. The main-level primary suite includes dual closets, while the upper level offers additional bedrooms and a dedicated storage room. Two spacious garages on either side of the home add balance and convenience. A timeless estate in the making—now available by private appointment. Own what cannot be replicated.

Easton The Oberoi Fox Chapel, Fox Chapel

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

$2,400,000

Introducing The Oberoi - Fox Chapel’s Last Great Estate Opportunity Tucked within the heart of Fox Chapel—one of Pittsburgh’s most prestigious and private communities—The Oberoi is a rare offering: approximately 20 acres of untouched, old-growth woodland. More than land, it’s the foundation for a lasting legacy. This is a singular opportunity to bring a personal vision to life—whether a residence of architectural significance, a retreat designed for generations, or an estate that quietly reflects permanence, beauty, and purpose. Set amid mature trees and gently rolling topography, The Oberoi offers extraordinary privacy and natural seclusion—just moments from the cultural institutions, country clubs, and academic life that define the Fox Chapel lifestyle. As one of the last large parcels available in this storied neighborhood, The Oberoi is a rare canvas for those with the vision to create something truly enduring. Now available by private appointment. Own what cannot be replicated.

Hawthorne The Oberoi Fox Chapel, Fox Chapel

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

$1,750,000

Introducing The Oberoi - Fox Chapel’s Last Great Estate Opportunity Tucked within the heart of Fox Chapel—one of Pittsburgh’s most prestigious and private communities—The Oberoi is a rare offering: approximately 20 acres of untouched, old-growth woodland. More than land, it’s the foundation for a lasting legacy. This is a singular opportunity to bring a personal vision to life—whether a residence of architectural significance, a retreat designed for generations, or an estate that quietly reflects permanence, beauty, and purpose. Set amid mature trees and gently rolling topography, The Oberoi offers extraordinary privacy and natural seclusion—just moments from the cultural institutions, country clubs, and academic life that define the Fox Chapel lifestyle. As one of the last large parcels available in this storied neighborhood, The Oberoi is a rare canvas for those with the vision to create something truly enduring. Now available by private appointment. Own what cannot be replicated.

Walden The Oberoi Fox Chapel, Fox Chapel

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

$1,600,000

Introducing The Oberoi - Fox Chapel’s Last Great Estate Opportunity Tucked within the heart of Fox Chapel—one of Pittsburgh’s most prestigious and private communities—The Oberoi is a rare offering: approximately 20 acres of untouched, old-growth woodland. More than land, it’s the foundation for a lasting legacy. This is a singular opportunity to bring a personal vision to life—whether a residence of architectural significance, a retreat designed for generations, or an estate that quietly reflects permanence, beauty, and purpose. Set amid mature trees and gently rolling topography, The Oberoi offers extraordinary privacy and natural seclusion—just moments from the cultural institutions, country clubs, and academic life that define the Fox Chapel lifestyle. As one of the last large parcels available in this storied neighborhood, The Oberoi is a rare canvas for those with the vision to create something truly enduring. Now available by private appointment. Own what cannot be replicated.

Easton The Oberoi Fox Chapel, Fox Chapel

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

$1,250,000

Welcome to this stunning red brick estate, perfectly situated on a picturesque 3-acre lot in the Fox Chapel School District. This exceptional property offers space, serenity, and timeless elegance in a truly coveted location. Step inside to find a warm and inviting living room with rich character, flowing seamlessly onto a covered patio — ideal for indoor-outdoor living and entertaining. The heart of the home is the eat-in kitchen with its own cozy fireplace, connecting to a formal dining room that overlooks the breathtaking backyard. A handsome office with a fireplace provides the perfect work-from-home retreat or quiet library space. The finished lower level offers even more room to relax and unwind, featuring a light-filled game room, full bathroom, and abundant storage. Whether you’re hosting guests or enjoying peaceful evenings under the covered patio, this remarkable home blends comfort, style, and privacy — all just minutes from the City, schools and shopping.

231 Hunt Road, Fox Chapel

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

$1,825,000

143 North Drive on Fox Chapel's premier street. Stunning 1920s colonial epitomizes sophisticated luxury with sprawling space. The central chef's kitchen boasts gas range, double ovens & granite counters. Charming breakfast/bar area with cabinetry flows seamlessly into spacious family room adorned with cathedral beamed ceilings and looking out into level backyard. Inviting living room with fireplace leads into sunroom, perfect for relaxation or game tables. Private office off of LR for serene workspace. 2nd floor 3 BR/3 BA layout includes laundry. Primary suite shines with a gorgeous, bright renovated bathroom featuring marble-clad shower, soaking tub & dressing area. 3rd level of 2 more BRs & updated hall bath. Finished lower level has convenient 5th full bath. Zoned HVAC. Exterior space is athlete’s & entertainer's dream! Sport Court. Stone patio & fireplace. Huge yard with space for pool. Close to downtown, Shadyside, Oakland & all major highways. Near FC parks, clubs, schools.

143 North Drive, Fox Chapel

Listing courtesy of BERKSHIRE HATHAWAY THE PREFERRED REALTY.

Selling Office: BERKSHIRE HATHAWAY THE PREFERRED REALTY.

$1,138,000

5 Beds ⋅ 4 Baths

Nestled on 1.7 scenic acres in Fox Chapel Borough, this reimagined luxury residence blends timeless design with modern sophistication. Consisting of 5 great sized bedrooms and 3.5 full baths. A striking addition anchors the home with a vaulted sun-drenched great room, sunroom, and chef’s kitchen featuring Wolf and True appliances, custom Omega cabinetry, Galloway quartz counters, and a spacious walk-in pantry. The expanded primary suite boasts 3 cedar-lined walk-in closets and a spa-inspired bath with a Thermasol steam shower. A private guest suite on the walk-out lower level offers comfort and seclusion. Stone patios, an outdoor kitchen, and tranquil wooded views complete this refined retreat—crafted for everyday living and elegant entertaining. Located in an established, mature tree-lined neighborhood, and has quick access to all schools, golf courses, restaurants, and more! Large home perfect for entertaining or big families!

38 Easton Road, Fox Chapel

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

Selling Office: PIATT SOTHEBY'S INTERNATIONAL REALTY.

$1,345,000

Be impressed by this sprawling contemporary ranch, over 5000 SF of versatile living space, all set on a level lot with 2 patios & a expansive backyard. Dramatic vaulted ceilings in the living&diningrms create a dramatic 1st impression, while a wall of glass brings in natural light offering picturesque views of the yard.The kitchen is sunkissed, boasting abundant white cabinetry, sleek black granite countertops, seating at the island, vaulted ceilings, skylight, walk in panty & comfortable breakfast area all open to the 1st flr familyroom, a gas fireplace creates a warm & cozy space. Glass doors lead to the patio. Room for everyone with 4 bedrms & 4.5 baths on the main level! Luxurious primary suite with huge walk in closet & spa-inspired bath. 1 of the guest bedrooms will surprise you with a loft space, a great teen retreat! Finished LowerLevel offers more space with a 5th bedrm, full bath, office, gamerm & 2nd familyrm complete with a brick fireplace & built in shelving. 3 car garage!

241 W Chapel Ridge Road, Fox Chapel

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

$975,000

Absolutely beautiful home with updates galore!

115 Tree Farm Road, Fox Chapel

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

$1,381,250

Stunning fully renovated home nestled on a cul de sac in a neighborhood within the Fox Chapel Borough. This 5 bedroom 5 1/2 bath home has been thoughtfully renovated with a first floor bedroom and space for future elevator. Welcoming entryway leads to a large dining room with a fireplace, large well appointed kitchen with granite counters, 2 dishwashers, 2 sinks , 2 ovens and stainless appliances which is open to the family room with large stone fireplace. A 1/2 bath, first floor laundry, office area and sun room complete the main floor. The 2nd floor includes another primary bedroom with ensuite bathroom with soaking tub & glass shower, another bedroom with ensuite bathroom and 2 more bedrooms which share a jack and jill bath.The finished basement includes a large game room, full bath, and locker area before entering the 3 car garage. Beautifully landscaped yard includes a stone patio and built in grill. Convenient location which is close to hospitals, stores and access to downtown.

230 Foxhurst Dr, Fox Chapel

Listing courtesy of RE/MAX SELECT REALTY.

Selling Office: PIATT SOTHEBY'S INTERNATIONAL REALTY.

$1,250,000

6 Beds ⋅ 5 Baths

Welcome to location, location, location. Classic 1928 Tudor on a 1.4 acre lot in the heart of Fox Chapel Boro. Enter along the sweeping front lawn to a spacious driveway. Once you walk in the entry you will appreciate the large living room with granite fireplace and sconce lighting, a sunroom with tile flooring and access to rear yard, a dining room fit for formal or informal gatherings, a breakfast room, den/office and kitchen with a back staircase and door to the rear gardens. Four spacious bedrooms, two classic tile floor baths, and numerous closets complete the second floor. A third floor has two bedrooms with a shared hall bath and a walk in attic. The lower level is partially finished with a half bath and laundry. Bring your own ideas to create a lifestyle that defies the ordinary.

634 W Waldheim Rd, Fox Chapel

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

$2,800,000

Newly built and never lived in architectural standout Inspired by the visionary principles of Frank Lloyd Wright. This custom built masterpiece in Pittsburgh, Pennsylvania utilizes western red cedar transported from Washington state to express architectural ingenuity & timeless design. Stepping into the grand foyer, guests are greeted by a sense of awe-inspiring spaciousness, enhanced by the open floor plan & flowing layouts that exude a sense of tranquility & balance. Rich materials & meticulous craftsmanship elevate the ambiance with understated luxury. Situated within a half mile of both the private Shady Side Academy & the Fox Chapel Area High School, this home sits between Oakmont Country Club, the Pittsburgh Field Club, and the Fox Chapel Golf Club. Additionally, the seamless commute to the nearby Google and Duolingo Offices ensures that residents can effortlessly navigate between work & leisure, further enhancing the allure of this sanctuary in the heart of Fox Chapel.

409 Fox Chapel Road, Fox Chapel

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

Exceptionally maintained townhome in the desirable, gated Trillium neighborhood of Fox Chapel. Large entryway leads to a family room with grand 2 story fireplace, wet bar, desk area, 1/2 bath and a well appointed kitchen with stainless appliances, eat-in area overlooking lush gardens and a screened in porch. Formal dining room, living room, and large bedroom (possible primary) with ensuite bath and lots of closet space complete this level. Second level includes a large primary bedroom with ensuite bath, a home office/dressing room with attached bath and another bedroom and a bathroom. Second level also includes the laundry room, a cedar closet and additional storage areas. Spacious rooms, high ceilings, gleaming hardwood floors and crown molding throughout the home. Basement is unfinished but plumbed for an additional bathroom. 2 car garage as well as an additional parking spot. Home is surrounded by acres of woodlands & parkland, unique homes & gate house with onsite caretaker.

$1,290,000

3 Beds ⋅ 5 Baths

14 The Trillium, Fox Chapel

Listing courtesy of RE/MAX SELECT REALTY.

Selling Office: PIATT SOTHEBY'S INTERNATIONAL REALTY.

$1,410,000

Welcome to 301 Hampton Road, a stunning 5-bedroom home nestled at the end of a quiet road in a highly sought-after close in location in Fox Chapel Borough. This distinctive residence offers unmatched charm, comfort, and privacy on a rare double lot. Surrounded by nature, it’s a peaceful retreat with lush greenery and a serene atmosphere. You'll love the updated kitchen with center island and walk in pantry space. Fantastic informal and formal living spaces to spread out and enjoy. A primary suite retreat with a study too, 4 additional bedrooms with roomy closets & 2nd floor laundry. The expansive flat driveway and large open lawn are perfect for outdoor fun—think ball games, tag, or future pool plans. Fantastic flagstone patio and gardening space. Come winter, enjoy the best sled-riding hill in the neighborhood! Whether you're relaxing in the tranquil setting or entertaining in style, this home blends timeless appeal with everyday livability. A true gem in Fox Chapel. Welcome Home!

301 Hampton Road, Fox Chapel

Listing courtesy of BERKSHIRE HATHAWAY HOMESERVICES THE PREFERRED REAL.

Selling Office: RE/MAX SELECT REALTY.

$1,795,000

Welcome to 251 Fairview Road, a 5 bedroom Colonial on 3 acres offering timeless charm, warmth and comfort.This spacious home features dual staircases, a classic living room that seamlessly flows to a serene porch and private patio, perfect for entertaining or relaxing.Enjoy breathtaking views from the rear of the property and a sprawling level lawn too.A gracious entry sets the tone for the expected well-appointed rooms with gorgeous floors, and doors outside from nearly every first-floor room.The kitchen is timeless with hand painted backsplash, lots of cabinetry, fine appliances and a gorgeous eat in area in the sunroom.Entertain in the exquisite dining room, the butlers pantry space and you will love the den with builtins and fireplace. Upstairs, there is a relaxing primary composed of a bedroom suite and an office. An additional 4 bedrooms, roomy closets and 3 full baths. Expansive level driveway for ample parking convenience and a 3car garage.Welcome home to this Fox Chapel Gem!

251 Fairview Road, Fox Chapel

Listing courtesy of BERKSHIRE HATHAWAY HOMESERVICES THE PREFERRED REAL.

$2,025,000

Welcome to 114 Hillcrest Road - an architecturally stunning home privately nestled on nearly 2 acres in Fox Chapel Boro. Illuminated w/ natural light from skylights & full-length windows, it features a dramatic sunken living room w/ soaring ceilings & a dual-sided brick fireplace. The gourmet kitchen impresses w/ sleek Eggersmann cabinetry, Thermador fridge & oven (steam oven, warming drawer/lights, 6 burners, griddle/grill), & an extra-large island w/ crystallized glass countertop & refrigerator drawers. The owner’s suite is luxurious w/ an office, sitting room w/ deck access, & spa-like bath w/ heated floors, soaking tub, glass shower, & dual walk-in closets. The lower level is equally impressive w/ 3 generously sized bedrooms, 2 full baths, a bonus room w/ Murphy bed, & game room that includes a convenient wet bar & direct access to the spectacular outdoor oasis! Outside, enjoy a saltwater pool w/ integrated hot tub, & grassy, fenced in yard - all set in a serene, tree-lined oasis.

114 Hillcrest Road, Fox Chapel

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

$1,135,000