Rare opportunity to own one of Galena's most iconic historic properties, offering the perfect blend of owner occupancy, investment potential, and an exceedingly scarce City of Galena short-term rental license, all perched high atop prestigious Quality Hill with some of the most breathtaking panoramic views in town. Built by Asa Haile, a licensed riverboat captain and accomplished mason, this stately Federal-style brick duplex with elegant Greek Revival influences has remained in the same family since the 1970s, lovingly passed from one generation to the next, and now presents a once-in-a-generation opportunity for its next steward. Encompassing over 4,500 square feet between two beautifully maintained residences, the property offers exceptional flexibility with one side licensed and successfully operated as a highly coveted City of Galena short-term rental (licensed for four-person occupancy), while the adjoining residence is ideal for owner occupancy or long-term rental income. The licensed vacation rental features three bedrooms, three full baths, a nicely appointed kitchen, spacious dining area perfect for entertaining, inviting living room centered around a cozy wood stove, private paver patio, and expansive windows that perfectly frame the spectacular vistas beyond. The owner's residence offers an updated kitchen, generous living room overlooking the incredible scenery, dining area, three bedrooms, three baths, convenient upper-level laundry/mudroom, and private aggregate patio. Rich with character throughout, both residences showcase remarkable historic craftsmanship including gorgeous original woodwork, period built-ins, wide-plank wood flooring, handsome decorative fireplaces, soaring ceilings, oversized windows, and countless architectural details that celebrate the home's enduring heritage. While the home's rich history and architectural details are extraordinary, it is the expansive covered front porch that truly defines the experience of living here, offering a front-row seat to one of the most spectacular vistas in Galena. Whether enjoying a quiet morning coffee as the town awakens below, relaxing as the sun sets beyond Grant's Home and Horseshoe Mound, or taking in the twinkling lights of historic Main Street and the Park Avenue skyline after dusk, the ever-changing views create an unforgettable backdrop in every season. Few homes in Galena command a setting of this caliber, where sweeping panoramas stretch across the city's historic rooftops and church steeples to the rolling hills and scenic countryside beyond. Additional amenities include separate attic spaces above each residence, individual basement/cellar areas, an attached one-car open garage/carport, and a convenient pass-through storage shed providing easy rear access to both residences. Located just moments from Galena's renowned shopping, dining, entertainment, festivals, and historic attractions, this extraordinary property combines architectural significance, irreplaceable views, remarkable flexibility, and income potential into one exceptional offering. Whether you're seeking a legacy residence with supplemental income, a premier investment property, or an iconic piece of Galena history, 209/211 S. Prospect Street represents an opportunity that rarely comes to market and may not be seen again for another generation.