Beautifully rebuilt and thoughtfully designed, this Downtown Issaquah property offers two separate homes on one spacious lot. Main home features 2 bedroom/1.75 baths, while detached 1 bed/1 bath 2021-built ADU (above garage) is ideal for rental, guest space, or multi-gen living. Main home pairs original character with an extensive 2019 renovation. Major updates include electrical, plumbing, sewer line, windows, siding, roof, minisplits with AC and earthquake retrofitting. Inside, fir hardwood floors, skylights, custom tile work, heated bathroom floors and thoughtful modern finishes add warmth & character throughout. The remodeled kitchen flows into the living spaces, while the primary suite features rare walk-in closet and remodeled bath complete with dual sinks. Second spacious bedroom features murphy bed for added flexibility. Lower level, accessed via spiral staircase, offers great ceiling height. Currently used as wine cellar, workspace and storage area, with plenty of other uses. Completely self-contained 1 bed ADU includes full kitchen, plus in-unit washer/dryer. Outside, huge fully fenced lot backs to greenspace, creating private setting with plenty of room to garden and enjoy outdoors. Two car garage provides exceptional flexibility. All of this just a few blocks from Front Street & Gilman Village, with restaurants, shops, theater & coffee nearby. Rare opportunity to own 2 distinct living spaces while enjoying the character and convenience of Downtown Issaquah!