Hawaii’s oldest standing homes are more than just places to live—they’re living pieces of history, offering a rare glimpse into the islands’ rich cultural tapestry. These homes reflect a beautiful blend of architectural styles, from traditional Hawaiian cottages to elegant Colonial Revivals and classic Craftsman bungalows. Each property tells a story of the people and moments that shaped Hawaii’s past. In this article, we will explore 12 of the oldest surviving homes across Hawaii.

1. Craftsman Home in Hilo, Hawaii (1909)

Built in 1909, this charming Craftsman-style home is located on a generous 0.72-acre lot in the serene community of Hilo. With a thoughtful layout, the home offers 4 bedrooms and 2 bathrooms, featuring classic elements such as a sloping roof, wooden details, and exposed beams. The lower level provides additional living space, ideal for privacy or rental potential. The outdoor space is perfect for various activities, and the property is surrounded by lush tropical greenery, offering a peaceful living experience.

2. Craftsman Home in Honolulu, Hawaii (1911)

Built in 1911, this expansive traditional Hawaiian-style home is situated in the serene Nuuanu Pali area. The property offers over 5,300 square feet of living space, featuring large picture windows that capture views of the forest and mountain, koa plank flooring, and a wood-burning fireplace. The home also includes a wine cellar, formal dining area, family room, and a separate guest quarter above the garage, all set in a peaceful environment.

3. Colonial Revival in Honolulu, Hawaii (1918)

Built in 1918, this Colonial Revival-style home combines classic architecture with modern convenience. Situated in the desirable Keeaumoku neighbourhood, this property offers spacious living with 7 bedrooms and 8 bathrooms, providing ample room for both private and shared living. The home features traditional Colonial Revival elements such as symmetrical facades, large windows for natural light, and a prominent front entry with classical detailing. Original features like wooden floors and crafted woodwork remain, enhancing the home’s historic charm. 

4. Hawaiian Plantation Cottage in Koloa, Hawaii (1918)

Built in 1918, this renovated home features 5 bedrooms and 3 bathrooms on a 0.74-acre lot. The home blends historic charm with modern upgrades, including a spacious kitchen, expansive great room, and energy-efficient systems. It offers a versatile layout ideal for multi-generational living, set in a private wooded area.

5. Craftsman Bungalow in Hilo, Hawaii (1918)

Built in 1918, this charming Craftsman-style home in Hilo offers a spacious layout with generous living spaces. The home features prominent stonework, a low-pitched roof with deep eaves, and large, inviting front porches typical of the Craftsman style. Inside, you’ll find ample natural light, hardwood finishes, and a welcoming atmosphere. The home includes separate living spaces and is surrounded by lush gardens, offering a peaceful, serene environment.

6. Contemporary Hawaiian Cottage in Honolulu, Hawaii (1920)

Built in 1920, this remarkable multi-family property offers an exceptional investment opportunity with diversification and long-term value appreciation. The property features 13,340 sqft of land with three homes, a 4-bedroom, 3-bathroom house in Kahala, and a 2-bedroom, 2-bathroom condo with tennis courts, a swimming pool, and a party room. This property provides a haven for investors looking for a reliable income source and potential for future growth, especially in uncertain market conditions.

7. Craftsman Home in Kukuihaele, Hawaii (1920)

Built in 1920, this Craftsman-style home offers a harmonious blend of historic charm and modern comfort. Located in the serene town of Kukuihaele, the property spans 0.44 acres and provides stunning views from its hilltop location. The home features a custom-built 2-bedroom, 1-bathroom living space, seamlessly integrated with a repurposed old church building that serves as a versatile living area with a kitchenette. The property is further enhanced by fruit trees, including avocado, cacao, and bananas, and offers a peaceful setting for multi-generational living, creative use, or as a private retreat.

8. Tropical Vernacular House in Mountain View, Hawaii (1920)

Built in 1920, this charming 3-bedroom, 1-bathroom classic red farmhouse estate on 2 acres in the highly coveted North Glenwood area offers a glimpse into Hawaiian history. The home features redwood construction, large-paned windows, vaulted ceilings, and magnificent ochre-coloured wooden floors. It includes a den/library for literary and religious inspiration and a comfortable, inviting atmosphere.

9. Contemporary Hawaiian Cottage in Volcano, Hawaii (1920)

Built in 1920, this charming 3-bedroom, 3-bathroom Contemporary Hawaiian Cottage is nestled on a 3.06-acre lot in Volcano Village. The home seamlessly blends historic charm with modern updates, featuring open beam ceilings, modern fireplaces, and a beautiful covered lanai. Lush native forests surround the property and offers a serene, private setting perfect for a multi-generational family or a personal hideaway. The Summit House boasts modern conveniences, including a new 10,000-gallon catchment system, a new driveway, and upgraded electrical and plumbing systems.

10. Modern Hawaiian Craftsman Home in Honolulu, Hawaii (1921)

Built in 1921, located in a single-family residential zoning area, enjoys “grandfathered” status due to its duplex configuration predating current zoning laws. This unique property offers a prime location, with easy access to local amenities and the vibrant Honolulu community. Although the zoning designates it for single-family use, the property’s versatility and income potential make it an attractive option for investors looking to expand their portfolio.

11. Plantation Cottage in Wahiawa, Hawaii (1922)

Built in 1922, this charming 2-bedroom, 1-bath bungalow offers an excellent opportunity for potential buyers. The home is located on a 5000+ sqft lot in the quiet Wahiawa neighbourhood, just a short distance from Schofield & Wheeler Airforce Base and Oahu’s North Shore. While the property requires updating, the spacious lot offers endless possibilities for renovation or expansion.

12. Contemporary Hawaiian Plantation Revival Home in Waianae, Hawaii (1924)

Built in 1924, this island-style duplex offers a luxurious and expansive living space with 5 bedrooms and 5 bathrooms across 3,295 square feet. The property has been fully remodelled to county code, with high 9-foot ceilings on the first floor, enhancing the spaciousness throughout the home. The spacious upstairs loft provides unparalleled views of Poka’i Bay’s turquoise waters and the majestic Waianae Mountains, perfect for relaxation or entertaining.