11 Madeira Dr

High, dry, and BIG ROI—this Madeira Heights compound is a rare opportunity on Anastasia Island. Offering both a single-family home and a detached guest cottage, this property generated over $101,000 in gross rental income last year. With unmatched returns in today’s market, this is a true gem for investors, multi-generational buyers, or anyone looking to blend lifestyle and income potential. The main home features four bedrooms and three full bathrooms. One of the bedrooms, located on its own wing of the house, includes a private entrance, full bath, wet bar, and sleeping loft. This oversized space can function as a luxurious primary suite, an in-law suite, or a separate rental unit—ideal for flexible living or maximizing income. The main home is filled with character and timeless appeal, including a dramatic wall-sized coquina fireplace, exposed wood rafters, and beautiful original hardwood floors. Updates throughout the home have been thoughtfully done to preserve the original mid-century charm while adding modern comfort. Tucked at the rear of the property is a separate cottage with a full kitchen and bathroom, offering even more opportunities for rental income, a home office, studio space, or private guest quarters. Between the main house and guest cottage is a peaceful xeriscape garden shaded by towering live oaks draped in Spanish moss. Meandering stepping-stone paths lead you to a cozy fire pit, jacuzzi, outdoor dining area, and freshly painted deck—a true oasis that feels worlds away while still being in the heart of the Island. Sitting at high elevation, this concrete block home is built to last. The metal roof and low-maintenance, no-mow landscaping were designed with easy Island living in mind. From this location, you can walk to the weekly Saturday farmer’s market or catch a live show at the St. Augustine Amphitheatre. The beach and downtown historic district are just a short bike ride away, making this home perfectly situated for enjoying all that St. Augustine has to offer. Whether you're looking for a short-term or long-term rental investment, a multigenerational setup, or a live-work compound, this property offers incredible flexibility in a sought-after location. With savvy investment appeal, character, and convenience all in one package, this Madeira Heights compound checks every box.