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Set on 3.45 private acres in the heart of Hollywood Hill, this extensively remodeled estate offers a rare blend of seclusion, scale & lifestyle. Positioned along the crest of “Heart Attack Hill,” a well-known local landmark, the property captures unmatched privacy while just minutes from Woodinville’s wine district. Expansive living spaces are designed for gathering, with a formal living room, oversized dining room w/sunset exposure, open kitchen + family room, and 5 fireplaces throughout. The lower level is built for entertaining w/a wet bar, pool table, theater room, and temp-controlled ~400 bottle wine cellar, plus an oversized flex room w/full bath and separate entry- ideal for guests, multi-generational or ADU potential. Upstairs features 5 generously sized bedrooms, a large loft/bonus space, and 3 more full baths, including a primary suite w/private balcony, fireplace, and spa-like bath. Outdoor living shines w/professionally designed landscaping, covered patio, and multiple gathering areas. Oversized 1,010 sq ft 3-car garage w/EV charger, plus two garden sheds. Minutes to DT Woodinville, wineries, dining, and within the highly sought-after Hollywood Hill Elementary, Timbercrest Middle, and Woodinville High service areas. Convenient access to major tech hubs- approx. 6 miles to Meta, 8 miles to Microsoft, 11 miles to DT Bellevue, 18 miles to UW/Seattle, and 3 miles to DT Woodinville. One-of-a-kind privacy & lifestyle in one of Woodinville’s most desirable locations.