A rare offering just steps from Highland Park, where classic brick architecture meets resort-style outdoor living. Perfectly positioned with front-row park views, this stately 3-bedroom, 2.5-bath residence delivers timeless character, meaningful system upgrades, and a private heated in-ground pool, an exceptional find in the city! Rich hardwood floors and original woodwork create an immediate sense of warmth and craftsmanship. The living room is both refined and inviting, centered around a decorative fireplace and anchored by a large picture window framing the greenery of the park beyond. A formal dining room with updated lighting offers elegant space for entertaining, seamlessly connected to a kitchen layered in warm wood tones, granite countertops, center island with storage, and distinctive wood-paneled ceiling detail. Outdoor living is where this home truly sets itself apart. The fenced backyard unfolds into a private retreat featuring an expansive patio for dining and lounging, dedicated grilling space, and a heated in-ground pool with updated liner and pump. Whether hosting summer gatherings or enjoying quiet evenings under the lights, the setting feels elevated and intimate. A detached garage and additional off-street parking via rear alley access complete the experience. Upstairs, three generously sized bedrooms include a primary suite with extended, deep closet space. The finished walk-out lower level offers flexible living space with updated flooring, a full bath with shower, and direct pool access, ideal for effortless entertaining. Large laundry and storage areas provide functionality without compromise. Major improvements include completely replaced roofs (house and garage), all new windows, new HVAC systems and hot water heater, new front door and railings, and replaced sewer line. Moments from reservoir trails, Bryant Street dining, and minutes to East Liberty, Shadyside, Lawrenceville, Oakland, and Downtown, this home offers the rare combination of architectural integrity, mechanical confidence, and private outdoor luxury - all in one of Pittsburgh's most coveted neighborhoods.