A timeless South Redlands classic with rare heritage, modern touches, and unmatched charm. Welcome to the Thomas M. Dugan House, a distinguished 1898 Historic Victorian Cottage and recipient of the Historical Society Heritage Award tucked into the heart of the Smiley Park Historic District. This is where old-world craftsmanship meets modern convenience in all the best ways. With over 2,500 square feet of open living area, 4 bedrooms, 2 full baths, and several bonus rooms, this home offers both space and soul. Step into a home where every detail tells a story—original hardwood floors, box beam ceilings, diamond-paned dual-hung windows, intricate moldings, and beautifully paneled custom pocket doors all speak to the timeless craftsmanship of 1898. Yet, this home has been painstakingly contemporized, with modern touches such as central AC/heating, recessed lighting, and indoor laundry room with sink and storage enhancing everyday living without compromising the home’s historical integrity. The expansive formal living room is the heart of the home, anchored by a unique river rock fireplace and filled with voluminious natural light from oversized windows. The adjacent dining room stands ready for both everyday dinners and special celebrations. The chef’s kitchen has been masterfully updated to blend heritage with high function, offering granite countertops, custom cabinetry, stainless steel appliances, a built-in Sub-Zero refrigerator, and a professional-grade 6-burner DSC range with griddle. Through the parlor, the airy family/game room features a distinctive v-shaped bay window. Upstairs, the primary suite is a peaceful retreat with a cedar-lined closet and a private, tiled balcony shaded by mature trees. The primary bath feels like a vintage spa retreat, featuring a clawfoot tub with a rain shower and a brass-enclosed surround. The gated driveway—EV-ready—leads to a detached two-car garage with an upper-level finished loft offering nearly 250 square feet of flexible space, well-suited for a creative studio, home office, or future junior ADU. Located on a classic, tree-lined street just blocks from downtown Redlands, Gerrard’s Market, and more—you’re surrounded by boutique shops, foodie spots, and historic charm at every turn, as well as award-winning schools, outdoor life, and quick access to amenities/travel options. Homes like this don’t come along often—and when they do, they don’t last. Come experience a true piece of Redlands history.