$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.
$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.
$575,000 5 Beds ⋅ 5 Baths Located in the desirable Fox Chapel Borough and in the O’Hara Elementary school zone, this spacious 5 bedroom, 4.5 bath home offers the perfect blend of charm, functionality and a flexible floor plan in a sought after close in neighborhood. Set on a level lot this home is filled with natural light and designed for both everyday living and entertaining, with a fenced level yard and multiple decks. The kitchen flows seamlessly into the family room and dining room and sun room creating an ideal open concept. The main level has a charming living room and also features a unique and highly desirable first floor bedroom suite complete with a large sitting room and a private ensuite bathroom, perfect for guests, extended family or flexible living needs. Upstairs you will find four additional bedrooms including a spacious primary suite with a fantastic bonus room above, ideal for a private sitting area or home office. The bedrooms offer generous closet space and the home provides an abundance of storage throughout. Additional highlights include a large level driveway and a tremendous oversized two car garage with a dedicated workshop and even more storage. Enjoy an exceptional location in the borough, you'll enjoy a walkable neighborhood, easy access to schools, parks, trails, and amenities of Fox Chapel area plus quick access to Rt. 28, the East End, UPMC hospitals, universities and downtown. 116 S Pasadena Drive, Fox Chapel Listing courtesy of BERKSHIRE HATHAWAY HOMESERVICES THE PREFERRED REAL. Selling Office: COLDWELL BANKER REALTY.
$448,500 4 Beds ⋅ 3 Baths Welcome home to this beautifully updated single-family residence in Fox Chapel, offering timeless charm, thoughtful updates, and a peaceful natural setting. Enter through the new front door into the sun-drenched main level, where gleaming hardwood floors and abundant natural light create a warm and inviting atmosphere. The spacious living room is anchored by a classic wood-burning fireplace—perfect for cozy evenings. The dining room features sliding glass doors that open to the rear patio, seamlessly blending indoor and outdoor living. Enjoy your morning coffee or evening meals overlooking the quiet backyard, where birds and local wildlife provide a serene backdrop. The remodeled kitchen is both stylish and functional, complete with appliances less than two years old, offering modern convenience and peace of mind. Just off the main living areas, the den showcases stunning floor-to-ceiling built-in bookcases—an ideal space for a home office, study, or private library. A beautifully updated half bath completes the main level. Upstairs, you’ll find four generously sized bedrooms, including a spacious primary suite with an updated ensuite bath featuring a sleek glass-enclosed walk-in shower. Three additional large bedrooms share a tastefully renovated full hall bathroom. All bathrooms throughout the home have been recently updated, ensuring move-in ready comfort. The unfinished basement provides excellent storage and offers exciting potential to be finished for additional living space. It also provides convenient access to the two-car garage and new driveway. Ideally located just one mile from the community park and grocery store, this home combines tranquility with everyday convenience. A rare opportunity to enjoy space, updates, and natural beauty in a prime Fox Chapel location. 202 West Dr, Fox Chapel Listing courtesy of REDFIN CORPORATION. Selling Office: COMPASS PENNSYLVANIA, LLC.
$202,000 3 Beds ⋅ 2 Baths Fantastic opportunity in the Fox Chapel School District! This solid 3-bedroom home offers great bones, timeless Craftsman-style character, and a layout designed for everyday living. The bright, open interior features spacious rooms, original hardwood floors on the main level, and new carpet upstairs, creating a warm and comfortable feel throughout. The family-friendly floor plan provides room to grow, gather, and make memories. Enjoy a large yard perfect for kids, pets, gardening, or weekend get-togethers. Conveniently located near schools, parks, and major routes, this home offers both charm and practicality in a sought-after community. Ideal for first-time buyers or families ready to put down roots and build equity while adding their own personal touches. Bring your vision and make this house your home! 1317 Old Freeport Rd, Fox Chapel Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES. Selling Office: RE/MAX SELECT REALTY.
$2,800,000 5 Beds ⋅ 7 Baths 407 Rhodora Lane, Fox Chapel Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES. Selling Office: HOWARD HANNA REAL ESTATE SERVICES.
$1,290,000 3 Beds ⋅ 5 Baths 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. 14 The Trillium, Fox Chapel Listing courtesy of RE/MAX SELECT REALTY. Selling Office: PIATT SOTHEBY'S INTERNATIONAL REALTY.
$820,000 5 Beds ⋅ 4 Baths Nestled on 2 acres of prime Fox Chapel property, this classic 5 bedroom, 3.5 bath colonial offers instant curb appeal, timeless charm and limitless potential. Bring your Pinterest ideas to this "ready for your updates" gem. Brick walkway leads from driveway to front door. Sprawling first floor with spacious room dimensions and fabulous floorplan. Classic features like fireplaces, hardwood flooring under carpets, beamed ceiling, and beautiful built-in bookcases. Eat-in kitchen. 5 bedrooms on 2nd level: primary ensuite bedroom with fireplace! Four more large bedrooms + 2 full baths with hall access. Space for 2nd fl laundry. Potential for additional living space on unfinished lower level. 2-car integral garage. Deck overlooking backyard fit for a nature lover's paradise. Feeds to elementary school FAIRVIEW. Direct access to Fox Chapel's Parkland hiking trails. 200 Millview Dr, Fox Chapel Listing courtesy of BERKSHIRE HATHAWAY THE PREFERRED REALTY. Selling Office: BERKSHIRE HATHAWAY HOMESERVICES THE PREFERRED REAL.
$385,000 4 Beds ⋅ 3 Baths This 4 bedroom, 2 1/2 bath home is located in the Fox Chapel School District. The property features mature landscaping that creates a charming exterior with vibrant foliage, nestled in a peaceful neighborhood. The interior of the home boasts hardwood flooring on the main floor providing a warm and inviting ambiance. The spacious layout allows for ample natural light to fill the rooms, creating a bright and airy atmosphere. The home provides ample storage solutions to meet the needs of the residents. Situated on a large corner lot, you'll have plenty of outdoor room for activities or relaxation. The home's well-proportioned rooms can accommodate a variety of living arrangements and furnishings. 301 N Rose Drive, Fox Chapel Listing courtesy of COLDWELL BANKER REALTY. Selling Office: HOWARD HANNA REAL ESTATE SERVICES.
$565,000 4 Beds ⋅ 3 Baths Located in a sought after, close-in Fox Chapel neighborhood, this cozy yet spacious home features hardwood flooring and 10 foot ceilings that create an open feel throughout. The versatile "L" shaped family room offers plenty of room for relaxation and entertainment, with a flexible floor plan, perfect for adapting to your lifestyle. Outside, a flat and functional rear yard provides the ideal space for outdoor activities, gardening or even expansion opportunities. The second floor provides a spacious primary bedroom with an en-suite bathroom as well as three additional bedrooms and bathroom. Whether you are seeking a family friendly layout or space for a home office, this property offers endless possibilities in a prime and convenient location. 113 Pasadena Drive South, Fox Chapel Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES. Selling Office: KELLER WILLIAMS EXCLUSIVE.
$705,500 4 Beds ⋅ 5 Baths A Kingsly original! If you're looking for a home with lots of unique extras to make your own then look no further. This house was designed, built, and lived in by the owner of Kingsly Homes. Tucked away on a 2.005 acre private setting in the Fox Chapel SD, it is only a short drive from downtown Pgh's vibrant cultural district, offering the perfect balance of suburban peace and city convenience. Ideally located at the end of a cul-de-sac, this picture-perfect home exudes character, charm and large spacious rooms. Upon stepping through the welcoming double door entry, you are greeted by a beautifully scrolled grand staircase that leads to 3 large bedrooms equipped with oversized closets. Main floor includes large, sunken living room with an expansive picture window, dining room, large breakfast room, family room with beautiful brick fireplace and outside access, den, and master suite with his and her closets. Large lower level with additional fireplace is awaiting your finishing touches. 24 Wedgewood Ln, Fox Chapel Listing courtesy of K & S REAL ESTATE, INC.. Selling Office: K & S REAL ESTATE, INC..
$2,200,000 7 Beds ⋅ 8 Baths Welcome to the Estate at 301 Fairview Rd! This timeless colonial stunner consists of just over 7600 sqft of living space, & is situated on 3.82 private acres in the Fox Chapel Area School District. First floor consists of exceptionally large rooms, copious natural light, elevated ceilings, & recessed lighting throughout. There are 3 separate sets of stairs that can take you to the second floor, which contains 7 well sized bedrooms, & 5 full bathrooms. Intricate detail, exquisite dentil molding, custom built-ins, marble floors, & original wood paneling only scratch the surface when it comes to the amount of character in this luxury home. The exterior grounds of the property are simply magnificent. A 20x50 in ground pool, impeccable stone pool deck, two cabanas (kitchenette and full bath), a serene courtyard, mature trees, prestigious governors circle, double driveway & extreme privacy to name a few. Other highlights: full home generator, sprinkler system, updated electrical/HVAC 301 Fairview Rd, Fox Chapel Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES. Selling Office: HOWARD HANNA REAL ESTATE SERVICES.
$1,350,000 5 Beds ⋅ 5 Baths Welcome to this exquisite 1865 farmhouse nestled on a breathtaking 3-acre lot in Fox Chapel that is steeped in history and boasting undeniable charm. The main house exudes warmth and character at every turn. Spacious living room flooded with natural light from expansive windows. Generous den with a wall of built-ins has doors to the expansive patio. Entertainment is elevated in the pool room. Elegant dining room, adorned with a fireplace. The heart of the home, featuring ample space and a serving buffet for effortless hosting. Adjacent, the informal dining room provides a relaxed setting for everyday meals. First-floor mother-in-law suite, offering privacy and comfort for guests or multigenerational living. Beyond the main house lies a charming cottage, boasting a living room, three bedrooms, two full baths, a kitchen, and laundry facilities. Perfect for extended stays or cozy retreat. Completing this remarkable property is a classic barn. Welcome home to Fox Chapel's hidden gem. 315 Old Mill Rd, Fox Chapel Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES. Selling Office: PIATT SOTHEBY'S INTERNATIONAL REALTY.
$3,081,650 5 Beds ⋅ 7 Baths Unparalleled elegance and sophistication. Extreme privacy and established luxury neighborhood in the Fox Chapel Area School District. This magnificent estate is perfect for a growing family as well as entertainment. Two story entry with pristine marble floors & wrap around iron staircase. Superb formal dining room and vast gourmet kitchen are connected by a welcoming wet bar area. Countless windows providing copious natural light, elevated ceilings, & recessed lighting throughout entire home. 2nd floor balcony overlooks stunning 23 foot high great room including exquisite floor to ceiling windows. All 5 oversized bedrooms comprise of ensuite bathroom & walk in closets. The primary suite boasts two exceptional walk in closets & marble cladded bathroom with soaking tub. 3 outdoor areas: covered patio, a screened in patio off of office, & a sun filled casual AND dining area overlooking the slate surrounded inground private pool! 3 car garage. Your move-in ready retreat awaits! MUST SEE! 111 Nantucket Drive, Fox Chapel Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES. Selling Office: HOWARD HANNA REAL ESTATE SERVICES.
$632,000 4 Beds ⋅ 3 Baths This Craftsman style home is the best of both worlds -- set in Fox Chapel but within walking distance of Aspinwall shops and restaurants. Ten-foot ceilings grace the first floor with quarter-sawed oak floors, original cabinetry, two fireplaces (one wood burning, one decorative), sunroom, and a large covered porch. The family room converts to a guest suite at a moment’s notice and includes a newly remodeled bathroom with accessibility features. The second floor consists of a primary bedroom with en suite bathroom, three additional bedrooms, guest bathroom, and laundry room. Gardens and mature oaks surround the home. The two-car detached garage has a new foundation, running water, sewer line, 100 AMP electrical service and 50AMP charging for any EV. The partially heated basement has ample storage and an integral garage suitable for a small tractor, gardening equipment, etc. The neighborhood is dog-friendly and the yard is protected by an invisible fence. 804 Delafield Rd, Fox Chapel Listing courtesy of COLDWELL BANKER REALTY. Selling Office: BERKSHIRE HATHAWAY THE PREFERRED REALTY.
$799,000 4 Beds ⋅ 3 Baths Nestled amidst lush trees, this charming home in the woods offers a tranquil retreat. The interior boasts warm wood accents, cozy fireplace and inviting spaces. Updated baths and tranquil Primary suite. Wonderful outdoor spaces and private patio for sipping morning coffee or stargazing at night while the sounds of birdsong and rustling leaves serenade you into a state of relaxation. Whether you're seeking solitude or hosting gatherings, this Woodland Farms haven is the ideal location! 143 Woodland Farms Rd, Fox Chapel Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES. Selling Office: HOWARD HANNA REAL ESTATE SERVICES.
$699,900 5 Beds ⋅ 4 Baths Welcome to 510 Dorseyville Road, a spacious & inviting home in the picturesque Fox Chapel. This 3,748 sqft residence is situated on a generously sized lot, combining the feel of ample living space with the coziness of a cottage. As you enter, you're greeted by a warm, inviting living room with a fireplace that sets a hospitable tone. The seamlessly blended open floor plan of the dining room, living room, and kitchen is tied together with the lovely hardwood flooring. The kitchen, outfitted with new KitchenAid appliances, is functional for everyday use and entertaining, thanks to its open and welcoming layout. The property includes five bedrooms, providing plenty of space for guests or setting up home offices. A large basement offers extensive storage capacity. The porte-cochèreoffers convenient covered space for unloading groceries or parking. Additionally, a detached three-car garage, complete with second-floor storage, enhances the home's functionality and appeal. 510 Dorseyville Road, Fox Chapel Listing courtesy of PIATT SOTHEBY'S INTERNATIONAL REALTY. Selling Office: COLDWELL BANKER REALTY.
$1,060,000 5 Beds ⋅ 5 Baths Spectacular home with a separate Carriage house in the heart of Fox Chapel. This spacious Colonial has an unexpected open floor plan with walls of glass w/view of the private backyard and Koi pond. Buyers will love the expansive, well equipped eat-in kitchen, the family room w/soaring ceilings, the cozy paneled den w/fireplace, the formal dining room w/bay window, the formal living room w/fireplace, the octagonal Bonus room and first fl powder rm. Upstairs is an open hallway leading to a spacious Master Suite plus an additional Ensuite bedroom and 2 more sizable bedrooms, a full bath and laundry area. Up the spiral staircase is a secluded loft, making an ideal bedtime retreat or office space. Hardwood floors and recessed lighting throughout. The Carriage house features an outdoor heated, lit and jetted spa w/a waterfall on a sandstone patio. Inside is a dining area, bedroom, full bath and a flex room plus a 2 car garage. On a cul-de-sac street. O'Hara Elementary or private schools. 604 Berkshire Dr., Fox Chapel Listing courtesy of BERKSHIRE HATHAWAY HOMESERVICES THE PREFERRED REAL. Selling Office: ENGEL & VOLKERS SEWICKLEY.