Tucked into the historic Abbott Tract in uptown St. Augustine, just one block from the bayfront and a short stroll to charming shops, galleries, and restaurants, this beautifully preserved 1920 coastal retreat blends timeless character with thoughtful updates and exceptional flexibility. Set on a deep, quiet lot, the property offers a rare private courtyard-style haven centered around a screen-enclosed saltwater swimming pool with built-in spa seating—perfect for relaxing afternoons or entertaining under the Florida sun. The main residence features 1,963 square feet with 3 bedrooms and 3 full baths, including a spacious 1st-floor owner's suite. Historic details such as wood floors, a gas fireplace, and a wide covered and screened front porch create warmth and charm throughout, while impact-resistant windows, a metal roof, and fresh interior and exterior paint add modern peace of mind. The open kitchen showcases white cabinetry, stainless appliances, and striking blue tile backsplash. Adding remarkable versatility, the property includes a private detached poolside guest suite with full bath, creating a flexible 4-bedroom / 4-bath layout ideal for hosting family and friends, a home office, or a quiet studio retreat. Additional highlights include crown moldings throughout, a detached 1½-car garage, lengthy paver driveway, fenced backyard with gas firepit, mature landscaping, and RS-2 zoning allowing for short-term rentals, offering excellent income potential. An exceptional opportunity becomes even more rare with the adjacent buildable lot at 45 Osceola Street also available for purchase, presenting possibilities for expansion, investment, or creating a true compound in one of St. Augustine’s most desirable historic neighborhoods.