Hawaii’s beauty isn’t just in its landscapes — it’s in the homes that have quietly stood for generations. These eight historic properties reflect the islands’ rich blend of cultures, architecture, and craftsmanship. From plantation-style cottages to ocean-view homes with native woods and wide lanais, each one tells a story of life shaped by breeze, light, and tradition. And while these homes carry the spirit of old Hawaii, they’re also move-in ready. Whether you’re drawn to coastal calm or hillside charm, these historic homes are still available for buyers who want something timeless.

1. Hawaiian Plantation-Style Home in Hilo, Hawaii (1925)

Built in 1925, this classic home in Pueeo, just minutes from Downtown Hilo, retains its charm and is a rare find in such good condition for its age, though it needs some updating. The home sits at the top of a 16,000 sqft lot, with the back dropping down to a running stream. High wood lat ceilings and hardwood floors flow from the living room to the dining room and into the kitchen, evoking memories of old Hawaii as a true Kamaaina Home. This property is also zoned RM-1 (Multi-Family Residential), allowing for one living unit per 1,000 sqft of land.

2. Craftsman Bungalow in Hilo, Hawaii (1918)

Built in 1918, this fully functioning 15-unit multi-family building is just minutes from downtown Hilo. This permitted three-story building was converted from a single-family residence to a 15-unit congregate dwelling with three and a half bathrooms and three full kitchens, one to service each floor. The lower level consists of six units renting for $350/month. The second level has five units renting for $400/month. The third floor has four units also renting for $400/month. Notice of rental increase has been given to all tenants.

3. Hawaiian Plantation Cottage in Wahiawa, Hawaii (1922)

Built in 1922, this charming 2-bedroom, 1-bath home in Wahiawa presents a fantastic opportunity for buyers to personalize the property. The primary dwelling needs updating, but with a 5000+ sqft lot, the potential and options are seemingly endless. Quiet and ideally located within the Wahiawa neighborhood, the property is near restaurants, shops, Schofield & Wheeler Airfare Base, and a short drive from Oahu’s famous North Shore.

4. Hawaiian Plantation Home in Hilo, Hawaii (1909)

Built in 1909, immerse yourself in historic Honoka’a with this enchanting dream home! Surrounded by warmth and charm, this captivating property offers a unique opportunity for both investors and families. Situated at the very end of Kou Street, this attractive location extends more privacy and a serene living experience. With its purposeful layout, this 4-bedroom residence provides the perfect blend of comfort and versatility. The property offers two living areas, an upper level with interior stairs leading to the lower level living space. Each level measures 896 square feet, complete with two bedrooms, one bathroom, a cozy living area, and a kitchen.

5. Hawaiian Plantation Cottage in Kilauea, Hawaii (1920)

Built in 1920, this home offers the rare characteristics and charm of older residences blended with desirable modern amenities. This very spacious 3-bedroom, 2-bath home includes an added room off the third bedroom, perfect for an office or extra space for kids/family. Recently, a rock wall and bamboo fencing were added, making the property private and secure for animals and children. Very well-loved, it features open beam ceilings in the living room and high ceilings throughout the rest of the house, presenting an amazing opportunity to own a very special home.

6. Hawaiian Plantation Home in Volcano, Hawaii (1920)

Built in 1920, this classic red farmhouse estate is located on the highly coveted North Glenwood Road in Volcano, Hawaii, on the Big Island. Everything about this unique property offers a glimpse into the past: stately large-paned windows, redwood construction, magnificent ochre-colored wooden floors, quaint stairways, vaulted ceilings, and a den/library meditation room for literary and religious inspiration. The residence has a comfortable, inviting ambiance, excellent for appreciating the beautiful surroundings of this Mauka (mountain) Hawaiian location.

7. Plantation Vernacular Home in Honolulu, Hawaii (1918)

Built in 1918, this rarely available multiple dwelling property is located on desirable Keeaumoku Street. The units are configured as follows: one 3-bedroom with 2 bathrooms, four 1-bedroom units each with 1 bathroom, and seven bedrooms that share 2 bathrooms without a kitchen. In total, there are 8 bathrooms and 7 parking spots. The 3-bedroom unit has an in-dwelling washer/dryer, and there are two coin-operated washers shared by other tenants outside. The property was completely remodeled in 1948, when the second floor was added.

8. Commercial Vernacular Home in Honolulu, Hawaii (1918)

Built in 1918, this cash-flowing property in the heart of Honolulu offers a mix of business and residential units with a strong rental history, presenting a great opportunity to own a fee simple property with 2 business units and 3 residential units. Easy access to major streets and seconds from H1 make the commute very convenient. Residential units, consisting of one 3-bedroom and two 2-bedroom units, are all located upstairs. Below is an established convenience store and storage space for a business or a potential second business space. The property also includes 2 parking spaces.