5236 W Cuyler Avenue Nestled on a beautiful tree-lined street in Portage Park, this lovely 4-bedroom, 2-bath Prairie-style bungalow blends timeless Chicago charm with thoughtful modern updates. Rich original woodwork, crown molding, and ten original stained glass windows create warmth and character throughout, while extensive improvements offer comfort and peace of mind. The inviting three-season porch features custom storm windows and screens (2019), making it the perfect space to relax. The spacious living and dining areas showcase classic craftsmanship alongside beautiful hardwood oak floors. The large eat-in kitchen includes a granite island (2022), ample cabinetry, walk-in pantry, and a lofted ceiling with abundant natural light. Newer premium appliances make this an ideal kitchen for living and entertaining: Bosch oven/range (2024), Bosch microwave (2024), Bosch dishwasher (2020), KitchenAid refrigerator (2020). New Power HG windows throughout the home and Power HG sliding kitchen doors (both installed in 2019) include lifetime warranties. Step outside and enjoy the beautifully maintained yard space, the newer back deck (2021), and the concrete patio. Newer backyard fence (2021) provides privacy and peace of mind. Two bedrooms complete the 1st floor; one is currently used as an office with a passthrough to the upper level. Upstairs, you'll find the spacious primary bedroom and the fourth bedroom, which are conjoined by a bonus room featuring beautifully refinished oak hardwood floors (2019). Additional highlights include custom upstairs doors (2022), a whole-house water filtration system (2019), and a whole-house fan (2025). Located just steps from Portage Park, this home offers easy access to neighborhood restaurants, green space, and recreation. Don't miss your opportunity to own this gem in one of the Northwest's most beloved neighborhoods!