9 Sylvan Dr

Legal grandfathered triplex Three separately metered residences 5 Bedrooms · 3 Bathrooms · 2,089 Heated Square Feet Fully furnished Private hot tub conveys Fully replumbed and fully rewired Conventional residential financing eligible Walkable Uptown / Fullerwood Park location Proven mix of short-term and long-term rental income A rare opportunity to own a legal, grandfathered triplex in Uptown St. Augustine—2 STR units are being sold fully furnished, income-producing, and eligible for conventional residential financing. Properties like this cannot be newly developed under today's zoning, making 9 Sylvan Drive as much a scarce real estate asset as it is a beautifully preserved home. Set beneath the live oaks of Fullerwood Park, this 1946 concrete-block Spanish Colonial blends historic character with modern reliability. Fully replumbed and fully rewired, it offers three separately metered residences, four off-street parking spaces, and a proven mix of short-term and long-term rental income—all within walking distance of the Historic District, the waterfront, restaurants, coffee shops, and the attractions that have made St. Augustine one of Florida's most sought-after destinations. Whether purchased as an investment, an owner-occupied income property, or a second home with built-in revenue, 9 Sylvan Drive offers a level of flexibility that is increasingly difficult to find in St. Augustine. The Three Residences The Retro Cottage - Projected $45k gross annual income 2 Bedrooms · 1 Bath · Approximately 841 Heated Square Feet The property's signature residence occupies the main level and has consistently been one of its strongest-performing short-term rentals. Offered fully furnished, it features a screened porch with a private hot tub and is ready to continue welcoming guests from day one. Sleeps 4. The Upper Apartment - $1450/mo 2 Bedrooms · 1 Bath · Approximately 768 Heated Square Feet A full second-story residence currently leased to a long-term tenant, providing stable in-place income while preserving flexibility for future ownership. The Uptown Cottage - Projected $36k gross annual income per 1 Bedroom · 1 Bath · Approximately 480 Heated Square Feet A detached guest cottage offering privacy, charm, and versatility. Whether used as a short-term rental, guest accommodations, or a quiet retreat, it adds a dimension rarely found in properties of this scale. Sleeps 4. 2,089 square feet of heated living area thoughtfully divided among three independent residences. More Than a Triplex Few properties combine this level of flexibility with this degree of scarcity. Some buyers will recognize an exceptional investment with established income already in place. Others will see the opportunity to live in one residence while the remaining homes offset the cost of ownership. Still others will find a second home that delivers both lifestyle and meaningful income in one of Florida's most historic coastal communities. However it is viewed, 9 Sylvan Drive represents something increasingly difficult to find in St. Augustine: a property that earns today, adapts tomorrow, and offers an ownership opportunity that becomes more difficult to replace with each passing year.Disclaimer: Information is believed to be reliable but is not guaranteed. Buyer is responsible for independently verifying all material facts, including square footage, lot dimensions, zoning, legal use and nonconforming status, short-term rental regulations, flood zone, insurance requirements, property condition, rental income and operating history, taxes, and all items included in the sale. Historical rental performance is provided for informational purposes only and does not guarantee future income. Furnishings and the hot tub are intended to convey subject to the terms of the purchase agreement.