321 Woodland Road

Highland Park, Illinois 60035

Built in 1928, this exceptional Tudor residence seamlessly blends timeless architectural character with beautifully updated living spaces in one of Highland Park's most sought-after neighborhoods. Offering approximately 4,550 square feet over 2 levels plus a lower level and two car garage, this 5-bedroom, 3.1-bath home showcases classic craftsmanship, expansive entertaining spaces, and an ideal layout for modern living. Set behind a circular drive on a beautifully landscaped property on a ravine, this home makes an unforgettable first impression with its striking Tudor facade, leaded glass windows, and mature trees. Inside, gracious formal rooms are balanced by warm, inviting gathering spaces filled with natural light and rich architectural detail. Just off the entry, a richly paneled library with its own fireplace offers a warm and sophisticated retreat. The oversized living room features hardwood floors, elegant millwork, and a beautiful fireplace, while the formal dining room opens seamlessly to a charming sunroom and expansive entertaining deck. A spectacular updated kitchen serves as the heart of the home with custom cabinetry, granite countertops, oversized island, professional-grade appliances, extensive storage, and an exceptional butler's pantry connecting the formal and casual living spaces. One of the home's most impressive features built by Fraerman Associates Architecture is the stunning vaulted breakfast room/sun-filled workspace addition surrounded by windows and overlooking the grounds-creating an inspiring everyday living space rarely found in homes of this era. The second floor offers five generously sized bedrooms, including a spacious primary suite with a large walk-in closet and private bath. Two bedrooms are connected by a Jack-and-Jill bath, while two additional bedrooms provide excellent flexibility for guests, offices, or family living. The lower level with approximately 2,000 square feet includes recreation space, laundry, abundant storage, and future expansion potential. While the home requires renovation and updating, it offers an exceptional opportunity to restore and personalize a truly iconic Highland Park Tudor with remarkable scale and architectural character, ideally located near downtown, Metra, parks, highly-rated Ravinia Elementary School, Ravinia Festival, and the lakefront.