Kaupo Homes with Fee Simple Land tenure

Welcome to Kaupo, a hidden gem nestled on the enchanting island of Maui, Hawaii. This tranquil neighborhood, part of the picturesque Hana district, offers a serene escape from the hustle and bustle of island life. With its breathtaking landscapes, Kaupo is a paradise for nature lovers and those seeking a peaceful retreat.

Kaupo is characterized by its stunning vistas of lush greenery, dramatic cliffs, and the sparkling Pacific Ocean. The area is home to a small, tight-knit community that embraces the spirit of aloha. Residents enjoy a slower pace of life, where the beauty of nature is just outside their doors. Hiking trails, pristine beaches, and the iconic Haleakal? National Park are all within a short drive, providing endless opportunities for outdoor adventures.

One of the most appealing aspects of Kaupo is the availability of homes with fee simple land tenure. This means that homeowners have complete ownership of their property and the land it sits on, providing a sense of security and permanence. Whether you're looking for a charming cottage or a spacious estate, Kaupo offers a variety of real estate options that cater to diverse lifestyles and budgets.

As you explore this enchanting neighborhood, you'll find a unique blend of natural beauty, cultural richness, and a welcoming community spirit. Kaupo is not just a place to live; it's a lifestyle that invites you to slow down, connect with nature, and enjoy the simple pleasures of island living. Discover your dream home in Kaupo, where paradise awaits!

Newest Kaupo Homes with Fee Simple Land tenure

$695,000

406336 MLS ⋅ Fee Simple Tenure

This 30-acre lot has sweeping ocean and mountain views along with all the privacy and tranquility that is characteristic of the region. The property’s terrain offers a multitude of choices for building and development. Kaupo is believed to be where the first Polynesians landed on Maui. It's a place with a rich history and many preserved cultural sites. Ancient Hawaiians called it wahi pana, “storied places”. The property is located off the Kaupo Gap Road, a natural feature of Haleakala National Park, and a gateway to exploring the Park's trails. A trail through the Kaupo Gap leads to the top of the volcano, winding through old Koa forests and dense rainforests. This is a rare opportunity to own a pristine slice of old Hawaii. Access to the property is on the Kaupo Gap Road, one-third mile off the Piilani Hwy.

Kaupo Gap Rd, Hana

Listing courtesy of Island Sotheby's International Realty(W).

$1,195,000

1 Beds ⋅ 1 Baths ⋅ 405926 MLS ⋅ Fee Simple Tenure

Also Listed as MLS#405925 Vacant Land. Tranquil Kaupo Retreat Discover peace and privacy on nearly 10 acres in scenic Kaupo. Thoughtfully designed for off grid living, this unique retreat combines rustic charm with modern comfort. Spaciously crafted 1 bed, 1 bath offers approx. 1,000 sq ft of living space with stunning 360' views. Take in Kaupo Gap from the Kitchen, to the sparkling Ocean vistas that surround, with Hawai'i off in the distance. A rare opportunity to own a slice of Southeast Maui paradise—ideal for a private retreat, artist’s escape, or nature lover’s dream. Please note nonconforming structures may exist. Photovoltaic-Off Grid Electric.E Komo Mai and come experience the untamed magic of Kaupo--where the pace slows, and the spirit soars!

34701 Piilani Hwy, Hana

Listing courtesy of Keller Williams Realty Maui-Ka.

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Based on information from the Multiple Listing Service of Hicentral MLS, Ltd. Listings last updated on . Information is deemed reliable but not guaranteed. Copyright: 2026 by HiCentral MLS, Ltd. IDX information is provided exclusively for consumers' personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.