Welcome to a rare live–work opportunity in the heart of Lake Helen’s Downtown Commercial District. This charming 2-bedroom, 1-bath home offers 1,040 total square feet and sits on a buildable double lot, opening the door to endless possibilities for living, working, and creating income in one of Central Florida’s most beloved small towns. Conveniently positioned across from Blake Park, home to popular Saturday markets and community events, this property features peaceful views of the equestrian center and Lake Helen’s iconic water tower, blending small-town charm with excellent visibility and accessibility. Zoned mixed-use, this property allows you to explore business opportunities while enjoying the convenience of living on-site. Whether you envision a boutique storefront, studio, office, wellness space, creative workshop, or income-producing venture, the flexibility here is exceptional. Inside, the home offers central air, a newer roof installed in 2019, and a layout full of character and potential, ready to be customized to fit your vision. Out back, a fully wired shed adds significant value and can easily be transformed into a workspace, studio, workshop, or additional business use. Located near local businesses, dining, and community favorites, and zoned for A-rated, award-winning schools, this property delivers both lifestyle and opportunity. Properties offering a double lot, mixed-use zoning, downtown location, and true live–work potential are rare in Lake Helen. 421 Pleasant Street presents a unique opportunity for entrepreneurs, creatives, investors, or owner-occupants looking to build something special. The Gem of Florida welcomes you!