Two classic early twentieth century homes are surrounded by enchanting gardens and majestic oaks, with sophisticated upgrades making this a rare property in the sought after Marengo neighborhood of South Pasadena. The 1926 front house is a timeless Colonial Revival with three bedrooms, two bathrooms, and den for working, exercising, or creating. After parking on the stately pea gravel driveway, enter the home under a charming gabled portico into the sumptuous interiors that seamlessly combine classical detailing with modern sensibilities. The home has been lovingly restored with artistic attention to detail - high-end upgrades include the Italian marble fireplace, custom steel work throughout, and built-in bookshelves. The ground floor features an en suite bedroom and walk-in closet, and upstairs are two more bedrooms and another updated bathroom. The gourmet chef's kitchen with state of the art appliances, including a Bertazzoni oven, features custom steel doors that connect to the magical garden where a custom cantilevered steel pergola canopies the outdoor dining space. The dappled light of mature 100+ year old oak trees canvas both backyards. Behind the front house's garden fence is a full second home, which was built by the property's original owners in the Normandy style in 1940. The sundial portico over the front door, and original Colonial style wood-burning fireplace are among its original features. This one bedroom, one and a half bathroom house has a separate address and entrance, allowing it the flexibility to be used as a guest house, work space, or income property. There is a small adjacent nursery to the main bedroom that can be utilized as a walk-in closet or a nursery. The property also includes an attached two car garage with a back entrance. The large property currently has its own captivating garden, but should one connect the two homes' grounds, the landscape design opportunities would be endless. The Americana chic property is blocks away from Garfield Park, blue ribbon schools, and downtown South Pasadena with its famous weekly farmer's market. The property qualifies for a 1031 exchange and is an ideal investment property.