Nestled in the exclusive and historic enclave of Castlewood Terrace sits this three-story Tudor Revival style home on a massive 90x114 wide lot. This 5BR, 3.2BA home has undergone an extensive renovation over the last four years, with every detail carefully crafted to ensure light, flow, and functionality were at the forefront. Built in 1909, Alexander Maltman, President of Aetna Bank, and his son, James, saw the opportunity to build lakefront estates, capitalizing on the growing entertainment district on Broadway Avenue. The Maltman's commissioned architect William Mann to design two Tudor style homes (this home and the one across the street), and the father-son duo built four homes total on the street, leaving an indelible mark on Castlewood Terrace. Natural light fills every square inch of the perfectly proportioned rooms, showcasing exquisite details crafted with the utmost precision. The first floor has a fluid layout-a captivating living room w/a wood-burning fireplace, adorned with a sleek custom-milled surround and bookcases. The naturally lit sitting room adjacent to the living room provides an ideal work-from-home environment, or space for large gatherings. The redesigned kitchen, semi-open to the living room, and open to the dining area, is a culinary haven with expansive counter space, professional-grade appliances, custom backsplash, handcrafted white oak cabinetry, and a contrasting handcrafted concrete island w/seating. Flowing seamlessly from the kitchen and dining room, the open and airy family room has new architect series Pella windows, custom wood paneling, a built-in media area, and a mudroom w/a discreet custom white oak closet. The family room extends to a two-tiered deck overlooking the pond and side yard. A tastefully updated powder room completes the main level. The upper level has three large bedrooms, including the expansive primary suite featuring a bespoke closet/dressing area, an additional walk-in closet, an office/sunroom, and a luxurious ensuite bath with a dual vanity and spa-like shower. Two additional bedrooms share access to the updated second full bath. The third floor is equipped with 2BRs, full bath, and ample closet space. This level offers many possibilities, such as a private primary suite, or guest/au pair suite, or office space. The modern aesthetic extends to the lower level, hosting a versatile play area with a preserved bar rumored to have once housed a speakeasy (in fact, when the sellers built the new garage, they found an underground tunnel believed to be part of a chain of speakeasies on the street)! Outdoors, the lushly landscaped fenced yard features a waterfall stone fountain, expansive grassy areas, and mature trees, creating a private suburban ambiance just moments away from downtown, Uptown, Andersonville, and Edgewater. The new 2-car Hardie board garage is equipped with custom storage, Pella architect series custom windows, and the option for an electric charging port. Adding to the allure of this home and location is the fact it is walking distance to the beaches along Lake Michigan, the Lake Front Trail, and one mile north of the Montrose Bird Sanctuary. Enjoy all the nightlife and entertainment Uptown has to offer, including concerts at the Riviera Theatre, Aragon Ballroom, and soon to be remodeled Uptown Theatre. Some of the best dining is within 2-4 blocks, including several restaurants in the Asia on Argyle corridor, Tweet, and Dib. Commuting downtown is simple: 146 (Gunnison & Marine, 1 block away) & 147 (Foster & Marine, 3 blocks away and runs express to Michigan Avenue) express buses, the Lawrence Red Line stop, or easy access to Lake Shore Drive!