Two beautiful homes on one rare grandfathered parcel in one of Hilo's most convenient neighborhoods. Set on an 18,024sf lot, this property offers the flexibility few Hawaii listings can match: comfortable multi-generational living or a diversified income portfolio with three distinct income streams. The front home, lovingly known as The Pineapple Retreat, was built in 1950 and refreshed in 2022. It's a welcoming traditional island style home with Hilo Bay views from the primary living areas. Below, an independent basement studio with its own private entrance, kitchenette, bathroom (and fallout shelter!) enjoys a stable longer-term tenancy - or easily combine the 2 units back to the original status to create a 4 bedroom, 2 bathroom single family home. The rear residence, Hilo Bayview, was built in 1980 and was fully renovated in 2021. Enjoy sweeping island vistas and trade-wind breezes from its upper living spaces, along with generous bedrooms and modern finishes throughout. The 4 bedrooms and 3 bathrooms are complemented by an office, storage area, and a home theater room. Both homes come fully furnished and currently operate successfully as short-term rentals, earning great guest reputations. From January 2027, the rear residence could continue as a 3 bedroom hosted Transient Vacation Rental (TVR) under the new Hawaii County code, with the on-site long-term co-host living in the front residence basement studio. Conditional approval has been granted with certificate BBR-00084. The front residence upstairs can be operated as a longer-term, 6 month minimum lease. A new septic tank system was installed in 2022. Minutes from downtown Hilo, farmers market, bayfront parks, restaurants, shopping, and the airport, 441 Mohouli balances island charm with a genuine investment opportunity. Enjoy a 3D walkthrough and floor plans at:- https://my.matterport.com/show/?m=q9Kz3uVZhmV&brand=0 Please do not disturb guests.