Nestled on a rare quadruple lot just steps from Chautauqua Park, this 1911 Craftsman-style home offers breathtaking views and thoughtful modern updates. Refined interiors and exquisite attention to detail combined with expansive outdoor spaces, breathtaking views of the Flatirons and Mt Sanitas, and proximity to iconic outdoor recreation and cultural opportunities make this home an exceptional Boulder retreat. This property includes 3 buildings on an oversized 1/4 acre lot, creating a small compound in the city. The historic main house offers light-filled living spaces with 9' ceilings, stained white oak floors, a gourmet kitchen with generous island and a picturesque dining room with giant picture windows and indoor-outdoor connectivity. The pristine primary suite offers its own sanctuary with wired sound system, double closets, ensuite bathroom and dual closets. A finished walkout lower level adds flexibility with guest quarters, storage and a mudroom. The detached guest house allows for additional flexibility with a main level studio space, 3/4 bathroom and upper level bedroom with a private balcony, while the original carriage house - insulated and electrified - offers a serene, creative space. Escape to the lush, landscaped, private backyard offering a flagstone patio, fruit trees, raised garden beds, and an expansive, level sports field ideal for a variety of recreational activities or large-scale entertaining. With ample parking, a single car garage + 2 additional parking spaces with an EV charger, and potential for future development, this is a must-see property and a rare opportunity in one of Boulder's most sought-after enclaves.