50 Charlotte St, St. Augustine, FL 32084

50 Charlotte Street | St. Augustine, Florida - An Iconic Corner in the Heart of the Historic District

Positioned at the prominent corner of Charlotte and Hypolita Streets, 50 Charlotte Street presents a truly rare offering in the heart of St. Augustine’s historic district that has been lovingly held as a legacy property by the same family for over 50 years. Just one block from the Matanzas River bayfront, this exceptional property is surrounded by renowned restaurants, boutique shops, and the city’s most celebrated attractions. With unmatched walkability, high visibility, and constant pedestrian and trolley traffic throughout the day, the location stands among the most desirable in one of Florida’s most iconic destinations.

Originally constructed in 1900, this two-story historic building embodies the timeless character and architectural heritage that define St. Augustine. Set on a fully walled lot, the property reveals a private, brick-pavered courtyard shaded by mature trees - an inviting and tranquil retreat that contrasts beautifully with the vibrant energy just beyond its walls. A classic wooden second-story balcony overlooks Charlotte Street, offering a charming vantage point of the lively streetscape with glimpses toward the bayfront.

The first floor features two thoughtfully designed units, including an inviting retail storefront and a separate residential apartment, each curated with finishes that honor the building’s historic integrity. The second floor hosts a beautifully appointed one-bedroom residence, complete with rich wood flooring, a cozy kitchen, traditional shuttered windows, and a full bath. This residence opens onto a private deck overlooking the courtyard, creating a serene and intimate outdoor living space.

Access from Charlotte Street welcomes guests through a charming entry into the courtyard, providing entry to the retail space, the second-floor residence, and an additional detached unit tucked within the courtyard - ideal for a creative studio, office, or flexible workspace. A second point of entry through an antique iron gate on Hypolita Street offers convenient access to the first-floor residential unit and the rear studio, enhancing the property’s versatility for multiple occupants or uses.

Zoned HP-2 (Historic Preservation 2), the property allows for a dynamic mix of residential and commercial uses, including retail, office, and hospitality-oriented concepts. With four total units, enduring architectural appeal, and a premier downtown location, this property offers exceptional flexibility for an owner-user, investor, or business operator. Whether envisioned as a boutique retail destination, professional office, income-producing investment, or a distinctive live-work environment, the possibilities are as compelling as the setting itself.

Please note: The current business does not convey with the sale, as it will be relocating to another downtown location. All occupants will vacate the property prior to closing. The square footage is approximate.