A block from the turquoise waters of Waimanalo Bay awaits a rare opportunity to own two separate dwellings in one of Oahu's most cherished beachside communities. Located in coveted Waimanalo Beach Lots, this updated property boasts numerous living spaces across a breezy, tropical lot -- ideal for multi-generational living, hosting visitors, great rental potential (separate electrical meters), or simply enjoying Waimanalo living. The front cottage features 2 bedrooms and 2 full bath, blending timeless charm & tasteful modern upgrades. Just behind, a spacious studio includes a full bathroom, kitchenette, & open living area; perfect as guest suite, creative space or home office. In back, a separate two-bedroom apartment sits above a converted garage, with a full kitchen, full bath and spacious open-air deck with sweeping views of the Ko'olau mountains, a peaceful spot for morning coffee or evening pau hana. Downstairs, the garage conversion adds even more flexibility with a large bonus space, kitchenette and full bath. Completely renovated in recent years with split A/C throughout. This home captures the spirit of Waimanalo living; relaxed, grounded and just moments from the shoreline.