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$2,395,000
6 Beds 6 Baths
Set on nearly one level acre in the heart of Fox Chapel, this exceptional residence combines luxury, comfort, and convenience with breathtaking panoramic views and an ideal close-in location. Designed with a modern flair for both everyday living and grand-scale entertaining, the home features an expansive open floor plan filled with natural light, seamlessly connecting elegant living spaces to spectacular outdoor areas. This home offers one floor living walking in from the 3-car garage. There is a possibility of an elevator if desired- space is allocated. The chef's kitchen serves as the centerpiece of the home, complemented by a fully equipped prep kitchen that makes entertaining effortless. Multiple spaces flow onto an expansive deck overlooking the beautifully landscaped grounds and scenic vistas beyond. The main deck has all new materials and can accommodate table seating for 12 plus a lounge area. On the other side of the home, the quaint covered side porch is perfect for cozy nights in. With six spacious bedrooms, including four private ensuite retreats, and five full baths, the home offers exceptional flexibility for family and guests alike. A dedicated theater and recreation area provides the ultimate entertainment experience, while the private basketball and sports court offers year-round opportunities for play and fitness. Skip the commute to the gym and enjoy the dedicated finished fitness space right at home. The large unfinished lower level room (currently used as a teen rec room) could be easily finished to any specifications. Thoughtfully designed with abundant storage throughout. This is a rare opportunity to own a luxury estate that delivers stunning views, unique and inviting floor plan, and an unmatched lifestyle.

218 Grandview Drive N., Fox Chapel

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

$1,895,000
5 Beds 7 Baths
Gracious 5-bedroom Colonial with a beautifully renovated guest house and 5-car garage, situated on a stunning, picturesque level cul-de-sac lot in one of Fox Chapel Borough's most desirable locations. Conveniently located near Fox Chapel Area schools, Shady Side Academy, the library, the Lauri Ann West Community Center, country clubs, shopping, and dining. This exceptional home offers spacious rooms, high ceilings, hardwood floors, and a wonderful floor plan designed for both everyday living and entertaining. The inviting living room with fireplace features a door to the outdoors, while the family room adjacent to the kitchen adds comfortable gathering space. A private office with built-in bookshelves provides an ideal work-from-home setting. The large eat-in kitchen is well-equipped with abundant cabinetry, extensive counter space, a center island, and is adjacent to a gracious dining room perfect for hosting family and guests. A first-floor laundry room and two powder rooms complete the main level. Upstairs, the spacious primary suite offers a walk-in closet and updated bathroom. Three additional generously sized bedrooms feature hardwood floors and ample closet space, including one with an ensuite bath and two connected by a Jack-and-Jill bathroom. The lower level includes a game room with fireplace, full bathroom, extensive storage, and direct access to the garages. The recently renovated guest house is a rare and special feature, complete with a bedroom, full bath, living room with a fireplace and kitchen—ideal for extended family, guests, an au pair suite, or private retreat. The spectacular rear grounds are truly an oasis, featuring a sprawling stone patio, level private yard, pond with waterfall, beautiful stone walls, and entire property has been professionally landscaped in the last few years. Well maintained and thoughtfully designed, this exceptional property offers the perfect blend of privacy, comfort, and an unbeatable Fox Chapel Borough location.Generator and water filtration sytem too! Easy commute to downtown, hospitals, universities and more. Welcome Home!

144 Springhouse Lane, Fox Chapel

Listing courtesy of 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.

$1,300,000
4 Beds 5 Baths
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.

Selling Office: HOWARD HANNA REAL ESTATE SERVICES.

$880,000
5 Beds 5 Baths
Beautifully reimagined with a focus on style and livability, this five-bedroom Fox Chapel residence offers three full and two half baths, set on a quaint lot in one of Pittsburgh's most desirable areas. The home showcases a refined, modern aesthetic with spacious interiors, elegant lighting, updated fixtures, and fresh, neutral finishes that create a bright and cohesive feel throughout. The main level is both inviting and visually striking, beginning with a warm living room highlighted by rich hardwood floors and flowing seamlessly into a beautifully updated kitchen. Designed with both function and style in mind, the kitchen features a gas range, abundant cabinetry, and a tasteful backsplash that adds texture and sophistication. Entertaining is effortless with a comfortable family room featuring a fireplace and wet bar, a sun-drenched sunroom (also serves as a great playroom), and a formal dining room perfect for hosting. An updated powder room adds a polished touch to the main floor. Upstairs, the spacious owner’s suite offers a serene retreat, complemented by four additional bedrooms, three well-appointed full bathrooms, and generous closet space throughout. Each room is thoughtfully designed with comfort and flexibility in mind. The finished lower level extends the living space with a large game room, ideal for relaxing, working out or entertaining, along with a half bath, laundry area, and convenient access to the garage with an EV charging station. Extensive recent improvements further enhance the home’s appeal and functionality. Between 2024 and 2025, updates include remodeled basement and living room spaces, along with key infrastructure upgrades such as a basement and garage waterproofing system, foundation reinforcement, updated venting, and improved exterior drainage through patio trenching, tree removal, and side yard regrading. In 2026, continued enhancements include a fully replaced gas line, garage wall stabilization, sealed venting, professional mold remediation, and a radon system, along with additional updates such as a repaired retaining wall, a new lamp post, and more. With its thoughtful updates, stylish finishes, and move-in ready condition, this home offers an exceptional blend of comfort, design, and everyday elegance all within Fairview Elementary district. Opportunities like this are rare, where thoughtful design, extensive updates, and true move-in-ready condition come together so seamlessly. Buyers won’t want to miss the chance to own a beautifully finished home in a prime Fox Chapel location that offers both immediate enjoyment and long-term peace of mind.

119 Shadow Ridge Dr, Fox Chapel

Listing courtesy of BERKSHIRE HATHAWAY THE PREFERRED REALTY.

Selling Office: HOWARD HANNA REAL ESTATE SERVICES.

$1,206,250
4 Beds 5 Baths
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.

$975,000
4 Beds 5 Baths
Flat Backyard! Located in the heart of Fox Chapel, near Fairview Elementary. This beautiful residence blends timeless architecture with thoughtful updates and refined living throughout. Rich hardwood floors span almost the entire home, complementing a well-designed layout that includes a formal living room, elegant dining room, and inviting family room with one of three wood-burning fireplaces. A pass-through wet bar enhances effortless entertaining, while the library and expansive sunroom offer versatile, light-filled spaces. The kitchen features quality appliances, including a JennAir electric stove and Bosch dishwasher. From the family room, step onto the brand new, impressive 53-foot composite deck, overlooking a flat backyard complete with raised garden beds, stacked stone wall (2020), and a covered patio below. Upstairs, the primary suite is a true retreat with a cathedral ceiling, multiple closets including two walk-ins, and a marble en-suite bath with jetted Jacuzzi tub and updated fixtures. Additional bedrooms feature hardwood flooring, another newly updated en-suite bath, and the hall bath has been updated with a double sink and walk-in shower. The finished lower level offers a game room with fireplace, full bath, walk-in pantry, and abundant storage. Additional highlights include laundry with chutes on every floor, three A/C units, a 2020 water heater, modular closet systems, 3-car garage! Mudroom, conditioned pantry, and an underground dog fence. Ideally located near the bus stop, this home offers a seamless blend of comfort, functionality, and understated luxury in one of Fox Chapel’s most sought-after settings.

131 Wilmar Drive, Fox Chapel

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

$1,325,000
5 Beds 5 Baths
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.

$750,000
4 Beds 4 Baths
Welcome to 210 Rutledge Drive, a home that offers exceptional curb appeal and a spacious, inviting layout designed for everyday living. This sprawling three-bedroom, four-bath residence features a flexible floor plan with generous room sizes, and an easy flow throughout. The updated kitchen is the heart of the home, showcasing abundant cabinetry, expansive counter space, and a large walk-in well designed pantry. The kitchen opens seamlessly to a comfortable family room with built ins and out to the covered side porch, creating the perfect setting for indoor-outdoor gatherings with family and friends, the patio extends in rear to a grilling area and side yard. The main living areas provide ample space for entertaining with a large classic living room, formal dining room and an eat in kitchen room. There is a fantastic sunny spacious hallway with walls of windows, perfect for indoor plants, and a sunroom area. Upstairs, the large bedrooms offer comfort and privacy, each with roomy closet space. The primary suite has a captive (4th) room that can be used as an office, library or sitting room or even a nursery. The lower level includes an office/game room, ideal for working from home. There is loads of storage, a mudroom off the 2 car garage and a dedicated laundry room. Set on a private lot, the rear patio provides a peaceful retreat with flowering trees. Located within walking distance to Aspinwall, this home combines convenience, charm, and space. It is a great location to all of Fox Chapel amenities, also easy access to schools, parks, and short commute times to the City, Shady side, Oakland, UPMC hospitals and more. Welcome Home!

210 Rutledge Drive, Fox Chapel

Listing courtesy of BERKSHIRE HATHAWAY HOMESERVICES THE PREFERRED REAL.

Selling Office: COLDWELL BANKER REALTY.

$1,915,000
5 Beds 5 Baths
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.

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