Historic charm, two homes on a double lot, a resort-style pool, and endless possibilities—welcome to one of Sanford's most unique properties. Step into the timeless charm of this rare historic Sanford property offering two homes on a spacious double lot just minutes from vibrant Downtown Sanford. Rich in character and thoughtfully updated where it counts, this one-of-a-kind property presents an exceptional opportunity for those seeking historic architecture, flexible living space, and room to make it their own. The main residence features 2,111 square feet under air (2,499 total square feet) with 3 bedrooms and 2 bathrooms. Original details blend beautifully with everyday comfort, including two wood-burning fireplaces—one in the formal living room and a second in the spacious family room addition just off the kitchen. The kitchen retains its vintage charm while offering generous workspace and overlooking the family room, making it ideal for gathering with family and friends. Relax on the screened porch overlooking the sparkling pool and enjoy the beauty of mature landscaping and majestic oak trees. The detached guest house offers approximately 1,600 square feet under air with two separate living areas of approximately 800 square feet each. The upper level includes a one-bedroom layout with living area, kitchen, and space for a bathroom to be reinstalled. The lower level is ready for the next owner's vision. Whether you envision guest accommodations, a home office, studio, hobby space, or future income potential (subject to buyer verification and local regulations), the possibilities are abundant. Situated on two parcels (309 & 311 W. 16th Street), the property offers alley access with off-street parking for approximately four vehicles, a large in-ground pool, and a setting that is increasingly difficult to find in today's market. Major improvements include roof (2022), main house HVAC (2022), complete electrical rewire (2021), and gas water heater (2019), providing peace of mind while preserving the home's historic character. If you've been searching for a property that offers charm, history, flexibility, and opportunity in one of Central Florida's most beloved historic communities, this is one you won't want to miss.