Welcome to 808 Ashland Avenue, an expansive 5-bedroom, 3.1-bath home perfectly situated on a 60x186 lot in the highly sought-after CAGE neighborhood and super close to dreamy Chestnut Beach! You will love the gracious floor plan and the incredible first-floor living spaces. Step into the welcoming foyer, complete with a convenient powder room, and flow into the large living room featuring built-in bookcases, a wood-burning brick fireplace and beautiful French doors that open to a bright sunroom overlooking beautiful Ashland Avenue. The beautiful chef's kitchen is complete with custom cabinetry, granite countertops, an island, stainless steel appliances, and seamlessly connects to the spacious family room. Do not miss the adjoining eat-in area with views of the stunning backyard-perfect for everyday living, private retreat, and family gatherings. An oversized formal dining room with beautiful wood-paneled ceilings completes the main level. On the second level, you will find 4 spacious rooms featuring 3 bedrooms and 2 full bathrooms, including a spacious primary bedroom with 2 generous closets and an en-suite private bathroom. The addition includes a bedroom with high ceilings and loads of windows overlooking the backyard. This bedroom connects to a tandem room-ideal for a home office, playroom, or potential 4th bedroom on the second level. The third-floor retreat offers 2 additional bedrooms connected by a Jack-and-Jill bathroom-an ideal space for guests, family, or flexible living. The unfinished basement provides excellent storage and future expansion potential. You will also appreciate the large laundry room, complete with a sink, counter space, and cabinetry-excellent space for a mudroom. Outside, enjoy a beautifully landscaped and private backyard with a large paver patio, perfect for summer entertaining. An oversized detached 2-car garage includes pull-down stairs for additional storage above. Lovingly maintained for many years and just blocks from the Metra, Gilson Beach, Plaza del Lago, and downtown Wilmette!