Welcome to 5450 Fair Oaks Street, a timeless 4-bedroom, 3-full-bath home nestled on one of Squirrel Hill's most picturesque tree-lined streets in the coveted Murdoch Farms neighborhood. Rich in character and architectural detail, this beautifully maintained residence has been thoughtfully updated while preserving its historic charm. Freshly painted throughout, the home welcomes you with a dramatic two-story living room featuring soaring beamed ceilings, a beautiful fireplace with a classic mantel, stunning leaded and stained glass windows, and an abundance of natural light. Just off the living room, a sun-filled den enclosed by two walls of leaded glass windows provides the perfect space for a home office, reading room, or peaceful retreat. The formal dining room opens through French doors to a spacious rear deck overlooking an exceptionally large, level backyard—a rare find in the city—offering abundant space for entertaining, gardening, or play. The kitchen features generous cabinet and counter space, a breakfast bar with seating for three, and a suite of Bosch appliances. An LG washer and dryer are also included. Beautiful hardwood floors extend throughout the main level and continue upstairs to the second floor. The spacious primary suite offers a walk-in closet and a private en-suite bath, while two additional bedrooms and another full bath complete the second floor. Both full bathrooms were completely renovated down to the studs by Marvista Design Build in 2021, blending timeless design with modern functionality. Throughout the home, you'll appreciate the abundance of storage, while the third floor provides exceptional flexibility with two additional finished rooms, a full bath, and a large storage area. The finished lower level adds valuable living space perfect for a family room, game room, fitness area, or playroom. Beyond its beauty, this home has benefited from extensive investment in major mechanicals and infrastructure, including all new Pella windows throughout with custom-built storm windows (2020), whole-house insulation by Insulwise (2020), a high-velocity central air conditioning system installed by Calfo (2022), a French drain and comprehensive waterproofing system by Baker's Waterproofing (2022), a radon mitigation system (2023), and a boiler replaced in 2018. Additional exterior improvements include a new garage door, exterior painting, and meticulous professional maintenance of the slate roof from 2018 through 2024, including new copper chimney flashing, copper valley work, and multiple slate repairs to ensure lasting performance. Additional highlights include a one-car integral garage, a private driveway providing convenient off-street parking, and an unbeatable location just minutes from Pittsburgh's renowned universities and world-class medical centers. Enjoy an exceptional walkable lifestyle with easy access to the restaurants, cafés, and shops along Forbes and Murray Avenues, the Carnegie Library of Pittsburgh, Schenley Park, and nearby public transportation.