Two cottages. One incredible opportunity! Welcome to The Sister Cottages — two beautifully restored historic homes in St. Augustine’s sought-after Abbott Tract. Sold together as a turnkey short-term rental portfolio with a transferable LLC, this rare offering provides both flexible living and exceptional income potential in one of Florida’s most desirable destinations. Completely rebuilt from the ground up in 2019, these residences blend classic craftsmanship with modern comfort, creating a pair of timeless retreats that celebrate the city’s heritage while embracing today’s lifestyle. Big Sister Cottage, originally constructed in 1844, stands as a masterwork of preservation and design. Every detail reflects a deep respect for its storied past — from reclaimed wood beams and cypress accents to crystal chandeliers, as well as curated antiques and art., With three bedrooms and three full baths, the home offers high ceilings, sunlit living areas, and a gracious front porch that evokes the charm and soul of the Old City. A private courtyard invites relaxation or entertaining under the shade of ancient oaks, blending indoor elegance with outdoor tranquility. Rare off street parking! Next door, Little Sister’s Carriage House is the last remaining coquina carriage home in Uptown St. Augustine — a one-bedroom, one-bath retreat that radiates character and craftsmanship. Compact yet refined, it mirrors the design integrity of its larger counterpart, with vintage-inspired details and modern updates throughout. Below, a coquina garage offers valuable utility space for laundry and storage, not included in the home’s square footage. Both cottages were rebuilt from the foundation up, with new roofs, plumbing, electrical, and mechanical systems, combining the integrity of historic architecture with the ease of low-maintenance, modern living. Perfectly positioned on oak-shaded streets just steps from the heart of downtown, The Sister Cottages enjoy an unrivaled location within walking distance of St. Augustine’s most treasured landmarks — including the Castillo de San Marcos, St. George Street, and the Bayfront. Together, they tell a story of heritage, design, and opportunity — a chance to own a piece of the Ancient City’s history, fully restored and ready for its next chapter as a private residence, investment property, or heritage retreat.
