EXTRAORDINARY OPPORTUNITY~BEST VALUE IN GLENCOE! Timeless East Glencoe elegance set on a beautifully landscaped .41-acre property with an expansive park-like setting as an extension of your backyard. 255 Harbor Street is a stately brick residence that blends architectural detail with refined, livable luxury in a premier location. A dramatic foyer creates an unforgettable first impression, introducing exquisite millwork, rich hardwood floors, 10 ft ceilings, and gracious proportions throughout. A sun-drenched living room, framed by oversized windows on three exposures, offers a sophisticated setting for entertaining or a casual vibe with an additional space for more relaxed gatherings. The generously sized dining room is impressive and includes a butler's pantry. An updated and sophisticated office offers a built-in bar and beverage center, a stone surround fireplace, coffered ceilings and rich custom cabinetry. Fully renovated kitchen features ample custom cabinetry, an oversized quartzite island with refrigerator drawers, high-end appliances, generous prep and storage space and flows seamlessly into the eat-in breakfast room and family room. The stunningly updated family room is highlighted by detailed custom built-ins, a stone surround fireplace, and French doors that open to the gorgeous private backyard- creating an ideal indoor-outdoor lifestyle with an expansive bluestone patio and built-in kitchen. Completing the main level are two powder rooms and a substantial mudroom/laundry room with direct entry to the attached 3 car garage. Upstairs, all 5 bedrooms are thoughtfully situated on the second level. An elegant primary suite includes a spa-caliber bath, abundant closet space, and private office. Each additional bedroom offers generous proportions and access to well-appointed baths, providing comfort and privacy for family and guests alike. The fully finished lower level includes expansive space for both activity and relaxation, with a large open recreation area ideal for games, media, and casual gatherings. A large indoor sport area with industrial netting provides exceptional space for a variety of athletic activities, workouts, and sports training. This thoughtfully designed level is further enhanced by a sleek wet bar with beverage refrigeration, an impressive temperature-controlled wine cellar, and a full bathroom. In addition to the fully renovated, kitchen, living room and office/library, substantial improvements include new windows (2023/2024), 1st floor air conditioner (2023), newer roof (2017), two 75-gal water heaters (2016), and more. This coveted location provides both presence and privacy with close proximity to both downtown Glencoe and Hubbard Woods, award-winning schools, parks, the lake, Green Bay trail, and public transportation. A great alternative to new construction. Welcome home to 255 Harbor Street!