Welcome home to Cheerio Tipp and The Little House--a legacy property in Carmel-by-the-Sea, offered for the first time in generations. This rare opportunity includes two houses on separate lots, totaling 9,663 sq ft, with individual parcel numbers and utilities. The larger Cheerio Tipp is rich in charm and lore. The family owned the first television in the neighborhood; friends and neighbors often gathered around to enjoy. On the main level, vaulted ceilings and old-growth redwood interiors create a warm, inviting atmosphere. Period details remain throughout--including a built-in pipe rack, a hidden safe, and cleverly concealed storage closets. A primary suite, spacious great room, eat-in kitchen, and loft with peeks of the Pacific complete this floor. Downstairs offers a full laundry room, guest suite, and two-car garage. Next door, "The Little House" sits on a 4000 sq ft lot and includes two bedrooms, one bath, a cozy living room with fireplace, and a generous deck. Both homes enjoy Carmel stone patios, garden space, and spots to sip morning coffee or dine al fresco. Just blocks from downtown shops, restaurants, galleries, and Carmel's white sand beaches, this is a rare chance to continue a cherished legacy and become the next custodian of an extraordinary double-lot property.