4420 Holland Avenue A Located in one of Oak Lawn’s most coveted pockets, 4420 Holland Ave delivers the kind of indoor–outdoor living experience that’s rare to find in the city. Sleek, modern lines frame every level of this light-filled home — but it’s the two incredible outdoor spaces that truly set it apart. On the first floor, a quiet, walled courtyard becomes your private green escape — perfect for morning coffee, gardening, or letting a pup roam. All the way up, the atmosphere shifts: the expansive rooftop deck feels like your own boutique hotel lounge, complete with a fire pit, shaded dining area, bar seating, built-in fridge & warming drawer, turf for lounging, and skyline glimpses. It’s built for sunrise routines, weekend gatherings, and evenings that stretch long past sunset. Inside, the home flows with clean modern design: an open-concept living level with floor-to-ceiling windows, a striking stone fireplace, custom built-ins, and a generous dining area suited for hosting. The kitchen features sleek cabinetry, a wide island with seating, stainless appliances, and warm natural light. The entire home is also enhanced by a sophisticated whole-home entertainment system, with in-ceiling speakers on every level and the rooftop deck, smart wiring throughout, and a Savant system upgraded in 2023 — allowing audio and video to be controlled from your phone and even play two different sources in different rooms. The primary suite is a calming retreat with a cozy fireplace, abundant built-in storage, and a spa-worthy bathroom complete with a freestanding soaking tub, oversized shower, double vanities, TV, and beautiful wood detailing. Both guest bedrooms have ensuite baths. The first floor bedroom opens to the garden and features built-in shelving, making it perfect for a home office. A private front-entry, 2-car garage rounds out the thoughtful layout.