This legacy property enjoys a premier location along the pedestrian bike path on the south side of Main Street, perfectly positioned between the base of Aspen and Shadow Mountain. Step outside right from the backyard onto the Midland Trail or Little Cloud Trailhead, offering effortless access to downtown's world-class restaurants, shopping, galleries, and skiing. The home's newly renovated outdoor spaces include a serene back patio with fire pit, in-ground hot tub, and expansive backyard- ideal for apres ski relaxation or summer BBQ under the stars. The well-manicured front lawn and ample off-street parking add both charm and convenience. Inside, the residence combines classic mountain sophistication with modern comforts. The main level features an updated chef's kitchen, a sunlit breakfast nook, formal dining room, and two spacious living and entertaining areas. A mudroom, laundry room, wet bar, and powder room ensure every convenience for rental guests. Upstairs, you will find three guest suites, each with its own en suite bathroom, plus a bunk room with loft and private bath- perfect for kids or overflow guests. The primary suite occupies its own wing, complete with private deck, spa-like en suite bathroom, and an oversized walk-in closet. This property seamlessly blends traditional Aspen charm, location, and livability, making it the perfect Aspen retreat just steps from all the action in town.