Kaupo Real Estate

Welcome to Kaupo, a hidden gem nestled within the breathtaking landscapes of Maui, Hawaii. This charming neighborhood, located in the serene district of Hana, offers a unique blend of natural beauty, cultural richness, and a tranquil lifestyle that is hard to find elsewhere.

Kaupo is characterized by its lush greenery, dramatic coastal views, and the soothing sounds of the ocean waves. The area is surrounded by pristine beaches and lush rainforests, making it a paradise for nature lovers and outdoor enthusiasts. Whether you’re hiking the nearby trails, exploring the scenic coastline, or simply enjoying a sunset from your porch, Kaupo invites you to embrace the beauty of island living.

The community here is warm and welcoming, with a rich cultural tapestry woven from the traditions of the Hawaiian people. Residents enjoy a slower pace of life, where neighbors know each other by name, and community gatherings are a cherished part of daily life. The local lifestyle is centered around outdoor activities, from surfing and snorkeling to farming and fishing, allowing you to immerse yourself in the island's vibrant culture.

Kaupo is also conveniently located near Hana, where you can access essential amenities, including local markets, eateries, and artisan shops. The famous Road to Hana, with its breathtaking vistas and cascading waterfalls, is just a short drive away, making it easy to explore everything this enchanting region has to offer.

If you’re seeking a slice of paradise that combines natural beauty, a tight-knit community, and a laid-back lifestyle, Kaupo is the perfect place to call home. Discover the magic of this unique neighborhood and experience the true essence of Maui living.

Newest Listings in Kaupo

$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.