Welcome to 375 Park Avenue, a rare opportunity to own a stately 5-bedroom, 4-bathroom Victorian-style residence nestled in the heart of Highland Park. Set on a beautifully landscaped 0.19-acre lot, this timeless home offers over 2,700 square feet of finished living space, plus a massive 3-car detached garage with soaring ceilings-ideal for a car enthusiast, workshop, or future coach house addition. Built in 1920, the property sits just minutes from Lake Michigan, downtown Highland Park, Sunset Woods Park, the Metra station, Ravinia Festival, and acclaimed District 112/113 schools. This is truly one of the most walkable and sought-after neighborhoods in Highland Park, offering both historic charm and unmatched convenience. From the moment you arrive, the home's classic curb appeal and recently refreshed landscaping make an impression. A large front porch and elegant architectural lines reflect the charm of a bygone era, while mature trees and a fenced backyard offer privacy and green space. Inside, the main level greets you with tall ceilings, rich original woodwork, hardwood floors, oversized windows, and intricate trim details that speak to the home's heritage. A spacious foyer opens to a formal living room with decorative fireplace, an expansive formal dining room, a bright front parlor/sunroom, and a full main-level bathroom. The rear family room and generously sized kitchen offer everyday functionality and flow seamlessly into the backyard for indoor-outdoor living. Upstairs, you'll find five true bedrooms, each with hardwood flooring and ample closet space. The primary suite is spacious and includes a full private bathroom. Two additional full baths on the upper level provide convenience for families or guests. All bathrooms have been updated over time with neutral finishes, but still leave room for customization. The unfinished attic offers even more space for potential expansion-perfect for a home office, creative studio, or future lofted retreat. The full basement, accessible from the rear staircase, provides flexible space for recreation, storage, or future finishing. The home's mechanical systems appear functional, and there is visible evidence of recent upgrades in parts of the interior, but additional cosmetic and structural repairs are recommended to fully modernize and maximize value. The exterior, while recently cleared and cleaned, is in need of paint, siding repairs, and trim restoration. There is visible wear from age, but the structure itself appears sound. This home is ideal for an owner-occupant ready to invest in updates or for a seasoned rehabber looking to restore and resell a property in one of the most desirable pockets of Highland Park. With strong resale comparables nearby, particularly for move-in-ready historic homes, the potential here is significant. The location is unbeatable: steps from Green Bay Road, downtown shops and restaurants, the public library, lakefront trails, and commuter rail. Top-rated Indian Trail Elementary and Highland Park High School serve the area, and year-round community events make this a vibrant place to live. Whether you're drawn by the architecture, the space, or the location, 375 Park Avenue offers the rare chance to own a piece of Highland Park history and shape it into your forever home. Properties with this combination of size, location, and potential do not come along often. Don't miss the virtual tour for a complete walkthrough of this special offering.