379 Highland Avenue Classic Tudor charm meets exceptional outdoor living in this beautifully maintained home just a few blocks from Upper Montclair shopping, cafes, restaurants, fitness studios, NYC train/bus access, Anderson Park and the hiking trails & Hawk Watch at Mills Reservation. Rich architectural character, warm inviting spaces & central air conditioning create a home that feels both timeless and effortlessly livable. The main level offers gracious living & entertaining spaces including a beautiful living room with fireplace, formal dining room, spacious family room, private office, powder room & eat-in kitchen, while both the kitchen and family room provide direct access to the wraparound deck for seamless indoor-outdoor flow. Outside, the property becomes a true, fully fenced, private oasis featuring an in-ground pool with expansive patio surround, poolside Pirate Bar & generous yard space ideal for entertaining, relaxing or play. The 2nd floor features a luxurious primary suite with dressing room & updated bath featuring a soaking tub & stall shower, plus 3 additional bedrooms & updated hall bath. The 3rd floor offers 2 more bedrooms & a 3rd full bath, providing exceptional flexibility for guests, offices or creative space. A rare opportunity to enjoy distinctive Tudor architecture, resort-like outdoor amenities & one of Montclair's most sought-after locations.