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Welcome to 537 S Cuyler, this well-maintained two-flat offers the perfect balance of character, flexibility, and convenience. Thoughtful updates blend seamlessly with original details like leaded glass windows, built-ins, and hardwood floors. Each unit has a spacious living room that opens into a bright sunroom, the perfect spot for relaxing with a book or setting up a home office. The kitchen and large dining room flow naturally into each other, creating a warm and inviting space for entertaining or enjoying everyday meals. Enclosed back porches on both levels add additional storage or the potential for additional living space. The first-floor unit is a generous duplex with 3 bedrooms and 2 full bathrooms, offering flexibility and room to spread out, including additional living area on the lower level. The second-floor unit features 2 bedrooms and 1 bathroom, making it an excellent rental, guest suite, or extended family living space. Shared storage and laundry are also located on the lower level. Set in a prime Oak Park location, you'll love the easy access to both the Green and Blue Lines and I-290 for a quick commute. The Community Recreation Center (CRC) is nearby, offering year-round programs, fitness, and activities. All of this is surrounded by the charm of Oak Park's tree-lined streets, welcoming community, and vibrant mix of shops, restaurants, and parks.