Welcome to Pillars Castle, a breathtaking architectural masterpiece located at 16 May Street in the heart of St. Augustine, Florida. This iconic estate, originally built in the early 20th century, has been meticulously restored to preserve its historic charm while incorporating modern luxury throughout. Known for its ornate engineering and timeless design, Pillars Castle stands as a symbol of the city’s rich heritage and offers a rare opportunity to own a fully licensed short-term rental in one of the most visited destinations in the country. Boasting over 4,400 square feet of living space, the property features four spacious bedrooms, four and a half bathrooms, a grand hall, formal dining room, chef’s kitchen, custom bar, a private patio perfect for entertaining or relaxing in the ocean breeze. The original stained glass windows, coffered ceilings, and stone fireplaces speak to the historic character of the home, while updated guest suites with en-suite baths, spa showers, and premium finishes provide comfort and sophistication. The beautifully landscaped courtyard with a fountain and gated rear-entry adds to the estate’s privacy and elegance, and ample off-street parking is a rare amenity in the downtown area. The property has a detached two-car garage, a covered carport, and an elongated driveway with plenty of parking that also allows you to exit through the rear of the property via the service road. Just minutes from the beaches, Castillo de San Marcos, the Fountain of Youth, Flagler College, and the shops and restaurants of St. George Street; the location is ideal for vacationers and history lovers alike. Actively operating as a luxury vacation rental, Pillars Castle commands premium nightly rates, making it both a stunning private residence and an exceptional investment opportunity. One of the bedrooms and bathrooms has a separate entrance with kitchenette and can be closed off to operate as a separate standalone rental unit or mother-in-law suite. Not to mention, furniture and everything within the property can stay! Don’t miss this chance to own a piece of St. Augustine’s living history–Pillars Castle offers the prestige, flexibility, and income rarely found in one extraordinary property.