Welcome to 203 Highland Ave., the only remaining example of the Second Empire Style of Architecture in Santa Cruz, and one of the most iconic homes in the city. This oft-published Painted Lady is perched prominently on a large corner lot in Santa Cruzs desirable Upper Westside and Westlake School District, and is being offered for sale for the first time in nearly 50 years. The 3BR+den, 2.5BA main house w/ 2,393sqft. includes a parlor & formal dining room w/ soaring ceilings, elegant spiral staircase, and period details. 3BR and 1BA upstairs, plus bonus space in the Cupola w/ distant ocean views. The den/4th bedroom and common areas are downstairs including the bright and airy updated kitchen. A 556 sqft. detached "carriage house" was permitted in 1989 above a 2-car garage loaded w/ storage, and the private yard with raised garden beds, mature fruit trees, a low-maintenance turf area, and room for a hot tub or fire pit is the perfect oasis for gardening, entertaining, playing, or relaxing. Easy commute location close to Hwy 1/Hwy 17, and a short stroll from downtown Santa Cruz, Harvey West, UCSC, W Cliff Drive, and many other Santa Cruz landmarks. An incredible piece of Santa Cruz history that may not be available again for another 50 years, this gem is not to be missed!