Introducing 66 Caleta Street, Old San Juan’s most coveted address.. Settled within the pristine treetops of the most historically significant strip in the oldest living city in the US.An intimate retreat steeped in history yet designed for modern living. Originally built in 1610 and carefully restored, this 3,290-square-foot residence unfolds across two levels, blending Spanish Colonial elegance with thoughtful updates. From the moment you step inside, the scale of the space is immediately felt, with 15-foot-high ceilings and handcrafted hydraulic tiles setting a tranquil tone. The home’s 5 bedrooms and 3 bathrooms are arranged to create a natural flow between gathering spaces and private quarters, offering a quiet retreat within the energy of the city. Designed for both entertaining and everyday living, the first floor spans 1,332 square feet, featuring a formal dining area, a chef’s kitchen, a wet bar, a breakfast nook, a guest bedroom, a full bathroom, and a cozy media room. A set of doors opens to an interiorpatio measuring 608 square feet, where an outdoor kitchen transforms meals into an alfresco experience. Upstairs, the 1,350-square-foot second level provides a more secluded sanctuary, with 4 additional bedrooms, 2 full bathrooms, and a secondary kitchenette/laundry area. A spiral staircase leads to the rooftop terrace, offering an elevated perspective of the city’s rooftops and the rhythm of life below. The architectural integrity of this home remains intact, with original marble flooring, restored archways, and exposed wooden beams. Every room is framed by 12- to 15-foot ceilings, amplifying the sense of space and airiness. For modern convenience, the home is fully furnished and equipped with a water softening system, backup power generator, 150-gallon water cistern, and a solar water heater. Located just steps from landmarks such as Hotel El Convento, Catedral de San Juan, and the iconic Puerta de San Juan, the home sits within history yet feels like its own intimate refuge within it. A rare opportunity to own a place where the past and present co-exist in perfect harmony.