Nestled in the heart of Highland Park, this enchanting 1920s Tudor gem exudes timeless charm and modern comfort. Rich, original woodwork and beautifully refinished hardwood floors set the tone throughout, while the upper level offers a private 3/4 bath and flexible space perfect for a home office or creative retreat. The galley kitchen has brand new stainless steel appliances and custom cabinets. Outside, a newer two-car detached garage boasts extra power and a sump system, and the attic provides valuable additional storage. The property includes off-street parking for three cars and a whimsical playhouse designed as a baseball press box-complete with a pitching area and newer high-privacy fencing, ideal for both play and privacy. With a walkability score of 81/100, you're just steps from local shops, restaurants, parks, and the esteemed Cretin-Derham Hall High School. The neighborhood's architectural heritage-especially its 1920s Tudor homes-is well documented and celebrated in Highland Park's real estate market. Nearby, you'll find a mix of charming local businesses and conveniences. Highland Park is known for its walkable streets and vibrant community feel, with popular spots like local cafes, boutiques, and parks just a short stroll away. This home is a rare blend of historic character and thoughtful updates-ready to welcome its next chapter.