Rarely does a property combine the character of Historic North Hill with the flexibility, privacy, and income potential offered here. Built circa 1919 as a purpose-built fourplex, this property was designed as a multi-family residence rather than a single-family home converted into apartments. The two downstairs units have been combined into an approximately 2,800 square foot owner's residence with 4 bedrooms and 2 bathrooms, while preserving two separate upstairs apartments of approximately 1,500 square feet each. Each upstairs unit offers 2 bedrooms and 1 bathroom. The current configuration offers flexibility and potential to restore the original four-unit layout, subject to buyer verification and approvals. Each residence enjoys a private entrance, separate utility metering, central HVAC, and functional floor plan. Each upstairs apartment includes a flex room overlooking W Strong Street, ideal for a home office. Architectural details include hardwood floors, extensive millwork, abundant built-ins, interior columns, high ceilings, and classic clawfoot tubs. The owner's residence features a covered front porch and partially covered rear patio, while each upstairs apartment enjoys an oversized private balcony. Situated on an unusually deep lot, the property features a New Orleans-inspired courtyard. Surrounded by mature landscaping and greenery, the courtyard provides a peaceful setting for entertaining or outdoor dining. The outdoor space is exceptional today, yet still leaves room for a future owner to explore possibilities such as a pool, garage, or other outdoor enhancements, subject to buyer verification of zoning, historic district requirements, and other applicable regulations. Located minutes from Downtown Pensacola, Pensacola Beach, shopping, dining, and entertainment, this is a rare opportunity to own one of North Hill's most distinctive income-producing properties. Floor plans, lease information, and additional photos available upon request.