Beautifully updated Hyde Park Greystone ideally located just steps from the University of Chicago Laboratory Schools and the University of Chicago campus. Offering over 4,500 square feet of thoughtfully designed living space, this exceptional single-family home features 5 bedrooms plus an office, 4.5 bathrooms, and an abundance of flexible living areas. Major updates include a newer roof and mechanical systems, including the air conditioning compressor and air handler, boiler, and hot water tank. The main level showcases timeless architectural details, beginning with a welcoming sitting room featuring inviting bay windows and a wall of built-in bookshelves. The elegant living room centers around a wood-burning fireplace with its stunning original mantel and flows seamlessly into a separate formal dining room through beautiful glass-paneled doors. The updated eat-in kitchen overlooks the expansive patio, backyard, and outdoor entertaining area. Upstairs features a spacious primary bedroom with an updated en-suite bath. Two additional large and one smaller bedroom and a full hall bath along with generous hallway closets complete this level. The versatile third floor provides exceptional flexibility with a large bedroom featuring bay windows, a full bath, walk-in closet, and a private office. This space functions equally well as a luxurious primary suite, guest suite, family room, or private retreat. The finished lower level adds even more living space with a large family room, full bath, laundry area, abundant storage, and a flexible room ideal as a sixth bedroom, second office, exercise room, or playroom. A covered exterior walkway accessible from the lower level provides convenient outdoor access and secure storage for bicycles, gardening equipment, outdoor furniture, and more. Combining classic Hyde Park architecture with extensive updates, generous living spaces, and an unbeatable location, this is a rare opportunity to own a move-in-ready historic home in one of Chicago’s most sought-after neighborhoods.