A rare opportunity to own a property filled with character, versatility and a fascinating connection to St. Augustine history. Situated beneath a canopy of majestic oak trees on nearly two private, fully fenced acres, this unique estate was once part of the historic Wolfe Ranch, owned by the family of prominent businessman, rancher and former St. Augustine mayor Herbert E. Wolfe. According to descendants of the Wolfe family, Presidents Dwight D. Eisenhower and John F. Kennedy stayed at the property during its years as a private lodge and summer retreat. The screened swimming pool is believed to be the original lodge pool, where generations of guests gathered and spent their summers. The pool was resurfaced and retiled in 2020, along with the installation of a new screen enclosure. The estate features two separate residences offering a combined 2,790 square feet, four bedrooms and three and a half bathrooms. The main home includes a 2023 addition featuring a spacious great room, walk-in pantry, guest room with attic access and a half bathroom with an exterior door for convenient pool access. Additional improvements include a new metal roof in 2023, new AC system in 2024, new appliances in 2021, new countertops in 2022, and updated valves and water lines for the sinks and toilets in 2024. Built in 2022, the detached 800-square-foot guest house offers one bedroom, one bathroom and separate utilities for added privacy and flexibility. It is ideal for extended family, guests, multigenerational living, a private office or potential rental income. The expansive grounds provide plenty of room for entertaining, gardening, recreation or simply enjoying the peaceful surroundings. A barn constructed in 2021 includes six custom cinder block dog kennels, an outdoor sink and a convenient wash-down hose. A durable metal roof was added to the barn in 2023. An extended driveway and additional parking provide ample space for residents, guests, recreational vehicles or equipment. With no HOA or CDD, this secluded estate offers remarkable freedom and flexibility while remaining convenient to World Golf Village, historic St. Augustine, shopping, dining and major roadways. Two homes, a storied pool, a well-equipped barn, six dog kennels and nearly two acres come together to create a truly one-of-a-kind St. Augustine property.