Located within walking distance of downtown Greenville, this exceptional 1927 Spanish Colonial sits on a large and private lot atop the historic North Main neighborhood. Built by Dr. William David Simpson, who owned Belk Simpson department store in Greenville, 2 W Hillcrest Drive is a true fortress. Featuring endless character and unparalleled quality, the "House on the Hill" includes 6 bedrooms, 5 full baths and 3 half baths that are thoughtfully placed throughout nearly 7,000 square feet and 3 levels of living space. Outside are 4 courtyards, each more beautiful than the last, covered arched terraces, a detached 6-car tandem garage and large, heated saltwater pool with covered hearth fireplace and ample space for entertaining. The freshly restored front iron doors bring you through the dramatic foyer, with soaring 12' ceiling and new limestone fireplace, to the light and bright formal living and dining rooms. A large, covered porch with fountain and views of the pool is a peaceful place to enjoy a meal or time with family and friends. The kitchen is a showstopper with its suite of premium appliances, hidden pantry and oversized island - all open to a large breakfast and keeping room with floor-to-ceiling arched windows overlooking the stunning gardens. Upstairs is a grand primary retreat with vaulted ceiling, fireplace, hidden office/coffee nook and views of Paris Mountain. The spa-like bathroom features a freestanding soaking tub, new dual quartz vanities and full-size marble steam shower with lounger. The dedicated closet is a full room with beautiful custom organization. A second bedroom with ensuite bath is also located upstairs while 3 additional bedrooms on the main level feature great space and privacy. A large office with handsome wood paneling and a fireplace fills with natural light from the two sets of double glass doors that open to a patio. The basement is a standout feature with exposed brick walls and hand-laid paver floors, housing a game/rec room and full wine cellar with a tasting room that once served as a garage for the original owner's Rolls-Royce. A bedroom suite on this level provides excellent flexibility for guests, and the oversized cedar-lined storage room is the perfect option for long-term storage. This spectacular home with pool and gardens designed by Dabney Peeples features timeless character expertly restored and reimagined for modern luxury living in one of the best locations in the US. Seize the rare opportunity to claim a piece of Greenville's storied history as your own!