Perched majestically on a hill, 334 Highbrook Avenue offers a rare combination of privacy, effortless flow, and modern conveniences. Built in 1920 and cherished by only three owners over the last century, this turn-key residence sits on a coveted through-lot spanning an entire block from Highbrook to Cliff Avenue. A comprehensive renovation and expansion done by the current owners transformed the home into a modern haven, beginning with a welcoming entry foyer that leads into an elegant formal living room anchored by a classic wood-burning fireplace. This space flows naturally into a gorgeous dining room, creating a sophisticated environment for hosting. Tucked nearby is a private main-level sunroom/office, where large picture windows perfectly frame "tree-house" views and stunning western sunsets. The heart of the home is the expansive chef's kitchen, equipped with a Sub-Zero refrigerator, dual Wolf ovens, Bosch dishwasher and a dedicated wet bar. Designed for both daily life and entertaining, the kitchen features an ample casual dining area and opens into a sun drenched second living room with a gas fireplace. Rounding out the main floor is the signature expansive porch—wired for sound and usable for over half the year. The upper levels offer abundant space and versatility, beginning with a second floor that hosts three generous bedrooms, including a primary suite with a custom walk- in closet and a serene bath. The fully renovated third floor boasts full-height ceilings and two additional large bedrooms, newly renovated bath, perfect for guests, an au pair, or a quiet home office. The lower level offers an additional 500 + square feet of finished space providing an ideal playroom, workout or hangout space. Throughout the entire home, Pella Architect series windows flood every room with natural light. This intentional connection to the outdoors culminates in the backyard oasis, where the expansive lawn ideal for sports and entertaining, and stone patios offer a level of privacy and scale (.43 acres) rarely found in the area. Adding to the home's exceptional convenience is a secondary entrance from Cliff Avenue, featuring a dedicated mudroom and easy access to the garage. With an unbeatable location, you are steps away from Colonial elementary school, minutes to the MS/HS and a short distance to the train station and downtown shops and restaurants.