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$1,103,000
4 Beds 5 Baths
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
4 Beds 5 Baths
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.

Selling Office: HOWARD HANNA REAL ESTATE SERVICES.

$1,605,750
5 Beds 4 Baths
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.

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.

$2,195,000
4 Beds 5 Baths
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.

Selling Office: HOWARD HANNA REAL ESTATE SERVICES.

$1,020,000
4 Beds 5 Baths
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.

Selling Office: HOWARD HANNA REAL ESTATE SERVICES.

$365,265
2 Beds 2 Baths
Fall in love with this charming cottage nestled on a corner lot in a peaceful tree-lined neighborhood in Fox Chapel! Inside, you will find hardwood floors flow throughout the functional floor plan. The living room features a fireplace flanked by built-ins and a large picture window. Entertain in the formal dining room that opens to the kitchen, boasting a breakfast bar, butcher block counters, and stainless steel appliances. A lovely sunroom leads outdoors to the patio surrounded by perennial gardens, creating a lush oasis. Easily accessible just a few steps up, the main level features 2 comfortably sized bedrooms and 1 full bath complete with a glass-enclosed tiled shower. The lower level has a 12x12 bonus room, a rough-in for either a full bath or half bath-currently equipped with a toilet, ample storage space, and a generous laundry area. 1 car garage. Just minutes away from Route 28, restaurants, shopping, & the Hospital. Don't miss the chance to make this gem your own!

300 S Pasadena Drive, Fox Chapel

Listing courtesy of PIATT SOTHEBY'S INTERNATIONAL 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.

Selling Office: HOWARD HANNA REAL ESTATE SERVICES.

$2,900,000
5 Beds 5 Baths
This award-winning Lindal cedar home, set on a prime corner lot in Fox Chapel Borough, blends sustainability with modern luxury. Awarded multiple honors by the Builders Association of Metropolitan Pittsburgh (BAMP), it features geothermal heating, solar panels, a Superior Wall System, and 10 zones of radiant heating. Exquisite craftsmanship includes mahogany doors, cedar ceilings, and Villeroy & Boch tiles. The gourmet CUVVE kitchen boasts Miele appliances and a Wolf induction cooktop. The first-floor primary suite offers spa-like elegance with a steam shower and expansive dressing room. Additional highlights include a lower-level great room with a built-in bar, a heated three-bay garage with EV charging, and a custom insulated greenhouse. Impeccable grounds feature Corten steel fencing and extensive landscaping. This fantastic location offers easy access to downtown, Shadyside, Shadyside Academy, Fox Chapel High School, The Pittsburgh Field Club, and Fox Chapel Golf Club.

999 Elmhurst Rd, Fox Chapel

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

Selling Office: HOWARD HANNA REAL ESTATE SERVICES.

$710,000
4 Beds 4 Baths
Nestled within the serene woods of Fox Chapel Borough, this secluded home offers unparalleled privacy and a touch of clandestine charm. The house boasts numerous windows and an open floor plan that seamlessly integrates with the natural surroundings, inviting the outdoors in. Tucked away in the basement lies a hidden gem—a real prohibition-era speakeasy, evoking a bygone era of secrecy and indulgence. Despite its tranquil setting, convenience is at hand, with shopping and dining just minutes away. The bustling city is less than a 20-minute drive, ensuring both tranquility and accessibility. , with Shady Side Academy a stone's throw away and Fox Chapel High School just a few minutes' drive. This home is a sanctuary where privacy meets convenience, offering a unique blend of historical intrigue and modern comfort.

33 Old Fox Hollow Lane, Fox Chapel

Listing courtesy of COLDWELL BANKER REALTY.

Selling Office: COLDWELL BANKER REALTY.

$1,300,000
5 Beds 5 Baths
Come home to your own private retreat. 3+ acres of resort-like living in the heart of Fox Chapel. 5000+sf mini estate hidden from view. Coveted private flat lot. Multiple versatile open & private areas. Pool w/water feature. Perfect for entertaining day & night. Open & shaded dining areas, concrete tables & seating, serving stations. Walking paths to secluded shaded hideaways. Nature-lovers dream. Stroll thru colorful perennials on carefully planted low maintenance grounds. Tennis court (potential for pickle ball courts?) situated at distance from the house to buffer sound. Architect-designed & built with focus on natural light & views of the private grounds. Main fl. Office & Laundry; 2nd fl: Guest/flex space w/full bath; secret hide outs; LL: Expansive fin. 15 course fndtn; mirrored dance fl. Governor’s Dr., 3-car att'd garage + extensive guest parking, fort, shed. Inv. Fence. Prime location near SS Acad, shopping, dining, major arteries. Fairview Elem. MUST EXPERIENCE TO APPRECIATE.

208 Fairview Rd, Fox Chapel

Listing courtesy of BERKSHIRE HATHAWAY HOMESERVICES THE PREFERRED REAL.

Selling Office: COLDWELL BANKER REALTY.

$833,000
5 Beds 5 Baths
Lovely Colonial located in Fox Chapel Borough in close proximity to parks, shopping, restaurants, UPMC hospitals, and Rt. 28. O’Hara Elementary School. Situated on a 1.2 acre lot surrounded by nature with great yard / outdoor living space! Flooded with natural light & generous room sizes throughout. 2-car attached garage enters into convenient mud room adjacent to the kitchen. Many updates including newly refinished hardwood floors, brand new garage floor, Hardie board siding, exterior recently painted, Trex decking, roof, windows, garage doors, front door, HVAC, water heaters, driveway, master bath fully remodeled & so much more! Radiant floor heating in the family room & dining room. 3 wood burning fireplaces. Spacious bedrooms with ample closet space. 5th bedroom/office option in the light filled walk-out lower-level adjacent to full bath and remodeled game room. 2 large storage rooms. Fantastic covered patio & large deck perfect for entertaining.

103 Westchester Dr, Fox Chapel

Listing courtesy of HOWARD HANNA REAL ESTATE SERVICES.

Selling Office: PIATT SOTHEBY'S INTERNATIONAL REALTY.

$2,000,000
5 Beds 5 Baths
Coveted Fox Chapel neighborhood. Timeless bright contemporary luxury living on 3.61 acres of private expansive manicured grounds. Custom 2010 build. Governor's drive. Two-story entry w/inlaid marble floors. Dramatic windows for spectacular views of park-like acreage. Main Fl. Quality Amenities: HW floors, spacious rooms, dramatic windows for views of tranquil grounds; Equipped kitchen w/dynamic functional design & hi-end appliances (2 DW's, drink fridg.); Wine Cellar, Den & Laundry. Upper level: Impressive primary suite, en-suite BA, super-sized WIC; 4 add'l BRs; 2 add'l full BAs. Extraordinary fin. LL: dedicated Theater w/motorized seating & popcorn mach., kitchenette & full BA. EXTERIOR SPACE IS PERFECT FOR ENTERTAINING: flagstone & omnistone patios, outdoor grill, water feature into koi pond, gazebo, sound syst. & lighting. SIX-CAR GARAGE PARKING (4 att'd/2 integral). Close to Shadyside Acad., parks, shopping, Univ's & Med. Ctrs. East End, Downtown & major arteries for EZ commute.

200 Staffordshire Pl, Fox Chapel

Listing courtesy of BERKSHIRE HATHAWAY HOMESERVICES THE PREFERRED REAL.

Selling Office: COLDWELL BANKER REALTY.

$1,699,000
6 Beds 7 Baths
Prime Fox Chapel location offering complete privacy on this 3 acre property. This spectacular 6 bedroom home reflects an elegant and modern design throughout. The 1st floor en-suite includes a beautiful bath with a walk-in closet, private laundry and private patio. The main living space gives you many options for entertaining from sitting in the dining room next to the fireplace to enjoying nature from the many large windows and patio. You’ll never tire from cooking in this wonderful kitchen which includes Fisher and Payel stainless appliances and quartz countertops. The 10.5 center island give you plenty of room to entertain. One of the bonuses to this kitchen is the butler’s pantry with 2 dishwashers and plenty of storage. All bedrooms include full baths and generous closet space. Private second En-suite above the large 3 car attached garage provides an added storage area and easy walk with groceries to the kitchen. Don't miss the opportunity to preview this incredible home!

1626 Powers Run, Fox Chapel

Listing courtesy of COLDWELL BANKER REALTY.

Selling Office: HOWARD HANNA REAL ESTATE SERVICES.

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