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$1,785,000
4 Beds 6 Baths
Welcome home to this fabulous two-story colonial nestled in the heart of Fox Chapel, set on a private, sprawling 2.25-acre lot. Fully renovated with high-end updates throughout, this home offers inviting spaces perfect for both everyday living and elevated entertaining. A gracious entry with open staircases sets an impressive tone from the moment you arrive. The top-of-the-line kitchen is a true showstopper, featuring a fireplace, cozy seating area, and a generously proportioned island, complemented by a convenient butler's pantry for effortless hosting. The large dining room boasts its own fireplace, while the living room impresses with soaring vaulted ceilings and abundant natural light. A large, covered deck off the family room and kitchen extends the living space outdoors. With 4 bedrooms, 3 full baths, and 3 half baths, there is space for everyone. The private primary suite is a retreat unto itself, complete with an oversized walk-in closet, a sitting room with fireplace, and a dedicated exercise room, plus convenient stacked laundry nearby. The lower level offers a large game room with fireplace opening to a private patio, along with an oversized laundry room. Outside, the expansive grounds offer endless possibilities for outdoor enjoyment and privacy, all just minutes from Pittsburgh's finest shopping, dining, and parks. A rare opportunity to own a beautifully updated estate on one of Fox Chapel's premier lots. Schedule your private showing today!

1256 Fox Chapel Road, Fox Chapel

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

$1,385,000
4 Beds 4 Baths
Set on over 2 acres in desirable Fox Chapel Borough, this contemporary home offers a private wooded setting, dramatic architectural details and exceptional indoor-outdoor living. Soaring ceilings, walls of windows, skylights and multiple fireplaces create light-filled spaces throughout. The inviting living room features a stone fireplace, beamed ceiling and French doors opening to a balcony, while the step-down family room is surrounded by windows and features vaulted ceilings, wood floors, two gas fireplaces and access to the expansive wraparound deck and stone patio. The eat-in kitchen is appointed with walnut cabinetry, granite countertops, a Wolf gas range with grill, stainless appliances, built-in sideboard and pantry. Upstairs, the spacious primary suite features a vaulted ceiling, fireplace, private balcony, walk-in closet and en-suite bath with jetted tub and double vanity. Two additional bedrooms, a newly renovated hall bath and convenient laundry complete the second floor. The upper-level bonus suite offers incredible flexibility with high beamed ceilings, wood floors, a stone fireplace, full bath, walk-in closet and beautiful views of the wooded grounds. The finished lower level provides additional living space, a den with full bath, patio access, generous storage and a private sauna. An exceptional contemporary retreat offering privacy, space and a connection to nature in the heart of Fox Chapel. All just minutes from Fox Chapel parks and trails, local dining and shopping, and convenient access to Route 28.

142 Riding Trail Ln, Fox Chapel

Listing courtesy of BERKSHIRE HATHAWAY THE PREFERRED REALTY.

$1,790,000
5 Beds 6 Baths
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.

$7,750,000
4 Beds 8 Baths
Welcome to a residence that redefines modern living, pairing timeless Tudor architecture with a minimalist, fully reimagined interior. Set on nearly 8 acres of rolling grounds in Fox Chapel Borough, the estate offers approximately 7,000 square feet of unsurpassed living space with every detail carefully crafted to perfection. From the slate roof and classic brick exterior, meticulously restored and preserved, to the new Kolbe windows and doors throughout, this residence showcases uncompromising quality. The all-new flooring, French oak, limestone, and antique terracotta, was sourced from François & Co. All of the interior paint is exclusively either Bauwerk Limewash Paint, an all-natural lime/plaster paint that acts as an air filter, or from Farrow & Ball. Completely remodeled, the lighting includes fixtures by Rose Uniacke, Jamb London, and Roman and Williams Guild. The interior doors are solid natural character oak with Classic Brass hardware. The mantels, all new, were custom made for this house, and the baths, also new, feature hardware by Waterworks. Filled with natural light, the main level benefits from expansive windows and numerous glass doors that allow easy access to the patios and grounds. Overlooked by a Juliet balcony, the spectacular great room is crowned by a magnificent new chandelier and exposed beams that have been painstakingly restored. Double doors reveal a generously sized den/office that opens to a brick patio. An extensive wet bar elevates the ample dining room. Anchoring the home with an ambiance both sophisticated and serene, the chef’s kitchen is appointed with white Olympia marble countertops and an 11-foot-long, solid walnut island. A Lacanche range with industrial-level Best hood and Gaggenau appliances— microwave, combi-steam oven, vacuum sealing drawer, and refrigerator—provide an unparalleled blend of performance and artistry. Fitted with walnut cabinetry, the butler’s pantry includes refrigerator and freezer drawers and an extra dishwasher. The side entry area has been reconfigured to create a dog grooming station and a second powder room. Upstairs, four bedrooms and four full baths include the sumptuous primary suite. A new double shower complements the soaking tub and towel warmer imported from Catchpole & Rye and the extensive walnut vanity with dual sinks. Dual walk-in closets are appointed with wicker caning and interior lighting, a theme carried through to a second suite with private bath. A third suite currently serves as a family room, while a luggage closet and a laundry room, consisting of two washers and two dryers, add convenience. The finished lower level features a luxury gym, a fifth full bath, and a separate entrance. The layout of the home ensures flexibility for everyday living and exceptional entertaining. Framed by rare 360-degree privacy, the outdoor terraces and gathering spaces invite seamless indoor-outdoor living. The property also includes a carriage home at the rear of the estate—currently uninhabitable, but rich in potential. With existing utility connections, it holds the possibility of becoming a guest house, studio, or destination for entertaining—an opportunity nearly impossible to replicate under current Borough approvals. This is more than a home—it is a once-in-a-lifetime offering for those who demand rarity, privacy, and enduring elegance.

Fox Chapel

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

$875,000
5 Beds 4 Baths
Authentic mid-century modern in Fox Chapel, on more than two private acres. This multi-level home offers five bedrooms, three and a half baths, and a mid-century interior that was never remodeled away. The living room sits under vaulted wood-beam ceilings, with floor-to-ceiling windows and a stone fireplace anchoring the space. The dining room carries the same wall of glass, with French doors opening to the outdoor living area. Natural light and lush greenery reaches every level, truly honoring natures relationship with the home. Hardwood floors run throughout the upper level, where the bedrooms are generously sized. The primary bath has been updated and includes a custom closet. The finished lower level adds flexible living space and looks out over the level backyard through its own bank of windows. New carpet and fresh paint have been updated throughout most of the home. Outside, an enormous brick patio, partially covered, overlooks the wooded and private grounds. The rear yard is flat, open, and fenced. A three-car garage provides parking and storage. Much of the home is original, including the kitchen and several of the baths, and is ready for its next chapter. Original tile, original cabinetry, and period details that are increasingly hard to find unaltered are all still here, waiting for a buyer who wants to bring them back rather than start over. Two-plus private acres, minutes from shopping, dining, and downtown Pittsburgh. Mid century homes on acreage rarely come available in Fox Chapel. Restore it or reimagine it.

101 Tomahawk Drive, Fox Chapel

Listing courtesy of PIATT SOTHEBY'S INTERNATIONAL REALTY.

$1,507,500
5 Beds 4 Baths
Welcome to 125 Riding Trail — a truly exceptional residence nestled in a spectacular private setting in the heart of Fox Chapel. Surrounded by mature trees and picturesque natural beauty, this home offers the perfect balance of luxury, comfort, and tranquility while remaining just minutes from Route 28, premier shopping, renowned hospitals, and private clubs.From the moment you enter the dramatic two-story foyer, you are greeted by soaring ceilings, expansive windows, and an abundance of natural light that flows throughout the home. Designed with both everyday living and entertaining in mind, the floor plan seamlessly connects the main living spaces while showcasing stunning views of the surrounding landscape from nearly every room.The spacious family room is the heart of the home, featuring oversized windows and sliding glass doors that open to incredible outdoor living spaces, creating the perfect indoor-outdoor lifestyle. The gourmet kitchen is thoughtfully designed with a large center island, generous cabinetry, stainless steel appliances, stone countertops, ample workspace, and a sunny breakfast nook ideal for casual dining. A standout feature of the home is the luxurious modern designed first-floor primary suite, offering privacy, comfort, and convenience all on the main level. This elegant retreat features spacious shower, counter space, and walk in closet. Nearby, the first-floor den provides the perfect flex space for a home office, or library.room. Adding architectural charm and character, the stunning fireplace creates a dramatic focal point in the living area, while the loft space above overlooks the main level and offers additional flexible living space. The upper level features three generously sized bedrooms and well-appointed full bathrooms, providing comfortable accommodations for family and guests alike. Second level loft-style bonus room could be 5th BR. Additional highlights include a convenient first-floor laundry room, oversized windows throughout, exceptional storage, and beautiful sight lines from every angle of the home. Outside, the property transforms into a private haven. The picturesque outdoor living areas provide the perfect backdrop for relaxing mornings, outdoor dining, entertaining guests, or simply enjoying the peaceful surroundings and unmatched privacy. This home combines timeless design, a functional floor plan, and a serene setting with convenient access to everything Fox Chapel has to offer. 125 Riding Trail is a rare opportunity to enjoy luxury living, privacy at its finest, and an unbeatable location all in one extraordinary property.

125 Riding Trail, Fox Chapel

Listing courtesy of BERKSHIRE HATHAWAY THE PREFERRED REALTY.

Selling Office: BERKSHIRE HATHAWAY HOMESERVICES THE PREFERRED REAL.

$1,300,000
4 Beds 4 Baths
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.

Selling Office: HOWARD HANNA REAL ESTATE SERVICES.

$755,000
3 Beds 2 Baths
Escape to this authentic mid-century modern stone ranch, tucked away on two parcels at the end of a tranquil road in Fox Chapel. Perfectly situated on 2.5 peaceful acres, this home harmoniously pairs vintage character with modern sustainability.   The MCM charm shines through large bay windows, two stone fireplaces, original hardwood floors, and preserved vintage tilework that beautifully accent the open floor plan—perfect for daily life or entertaining.    Recent high-efficiency upgrades include a brand-new solar roof (2025), Mitsubishi heat pump (2025), and comprehensive whole-house insulation ensure modern energy efficiency without compromising the home's original aesthetic.    The expansive, professionally waterproofed and reinforced lower level offers a large finished recreation room—perfect for a home theater or private gym. Adjacent to this living space is a versatile walk-out workshop providing ample storage and utility.  The large attached two car garage provides additional space for potential expansion.   Outside, the property is a living gallery of Pennsylvania’s natural beauty. From the established orchard to the certified backyard habitat and native woodlands, the landscaping has been thoughtfully curated over decades.   Located just minutes from Fairview Elementary and a short 20-minute drive to downtown Pittsburgh, this Fox Chapel gem offers a rare blend of secluded retreat, modern efficiency, and suburban convenience.

90 Dietrich Rd, Fox Chapel

Listing courtesy of COLDWELL BANKER REALTY.

Selling Office: HOWARD HANNA REAL ESTATE SERVICES.

$1,800,000
4 Beds 5 Baths
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.

$970,000
4 Beds 5 Baths
The most prime central location in Fox Chapel, located in the Fairview Elementary school zone. Great opportunity! This expansive brick residence approximately 4700 Sq.Ft. blends timeless charm with exceptional everyday livability, set on a stunning 3 acre parcel with mature landscaping and endless potential for a pool, gardens or play areas including soccer, baseball, football or playing catch. The first floor primary suite offers a fireplace, custom built ins and a spacious walk in closet, providing comfort and convenience for today’s lifestyle. The spacious kitchen offers generous counter space, abundant cabinetry and an adjoining eat in area, seamlessly opening to the inviting family room with fireplace and custom built ins. From here, step out to the covered porch and impressive stone patio, perfectly designed for effortless indoor outdoor entertaining, all overlooking the private, expansive backyard. Entertain with ease in the gracious dining room featuring a wet bar and built ins, the classic living room with fireplace, a dramatic vaulted ceiling sunroom filled with natural light and off the entry area is an additional parlor offering flexible living space. A convenient first floor laundry and powder room add everyday ease. Upstairs, three additional bedrooms and two full baths are complemented by excellent closet space and storage throughout. Hardwood flooring extends across most of the first and second levels. The lower level offers a comfortable game room, half bath and dedicated utility area. A level governors driveway and three car garage enhance both function and curb appeal. Ideally located with easy commute times to the city, the East End and UPMC hospitals, and the Fox Chapel Area High School campus, Shady Side Academy, library, community center, parks, trails, Fox Chapel Golf Club, Pittsburgh Field Club, Racquet Club and swim clubs, and shopping.

1001 Fox Chapel Road, Fox Chapel

Listing courtesy of BERKSHIRE HATHAWAY HOMESERVICES THE PREFERRED REAL.

Selling Office: COLDWELL BANKER REALTY.

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