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Lifestyle

Discovering Upcountry: A Guide to Maui's Luxury Estates in Kula and Makawao

Riette Jenkins | September 9, 2025

When most people dream of Maui, their minds conjure images of golden beaches and oceanfront villas. However, for a discerning few, the true magic of the island lies nestled high on the slopes of Haleakalā, in the breathtaking region known as Upcountry Maui. Here, communities like Kula and Makawao offer a distinct and profoundly luxurious lifestyle—one defined by expansive acreage, panoramic views, cooler climates, and a vibrant local culture.

This is a side of Maui I have cherished and come to know intimately over my 38 years on the island. While my name is often associated with the oceanfront prestige of Wailea and Makena, my experience extends deep into these elevated landscapes. Upcountry Maui provides an unparalleled sense of peace, space, and a unique connection to the island's agricultural roots, attracting buyers who prioritize privacy, bespoke living, and breathtaking vistas away from the bustling coastline.

The Allure of Upcountry: Why Discerning Buyers Choose Kula & Makawao

The appeal of Upcountry Maui is multifaceted, offering a lifestyle that stands in elegant contrast to the coastal resorts.

  • Panoramic Vistas: From these elevated positions, properties boast sweeping, unobstructed views that often include both the north and south shores, the West Maui Mountains, and the outer islands. Sunrises over Haleakalā are a daily spectacle.

  • Temperate Climate: Due to the higher elevation, Upcountry enjoys a cooler, less humid climate than the coast. Mornings are crisp, days are pleasantly warm, and evenings can be cool enough for a fireplace – a true luxury in Hawaii.

  • Expansive Acreage: Unlike the compact lots of coastal communities, Upcountry estates typically offer significant acreage, providing unparalleled privacy, space for gardens, orchards, equestrian pursuits, or simply room to breathe.

  • Authentic Charm: Makawao, a historic paniolo (Hawaiian cowboy) town, offers a unique blend of boutique shops, art galleries, and farm-to-table dining, all steeped in old Hawaii charm. Kula is renowned for its agricultural beauty, with lavender farms, wineries, and flower farms.

Spotlight on Luxury Upcountry Communities & Property Types

The luxury properties in Kula and Makawao are diverse, ranging from historic ranch homes to modern architectural masterpieces.

Kula: Refined Elegance with Horticultural Roots Kula is synonymous with agriculture, cooler temperatures, and some of the most spectacular views on Maui.

  • Luxury Estates: Many properties here are multi-acre parcels with custom-built homes, often designed to maximize the incredible views. Expect features like gourmet kitchens, sprawling lanais, and beautifully landscaped grounds.

  • Farm-to-Table Living: Ideal for those who dream of growing their own food, cultivating orchids, or even owning a small vineyard or coffee farm. The rich volcanic soil is incredibly fertile.

Makawao: Historic Charm Meets Contemporary Luxury Makawao offers a blend of historic charm and artistic vibrancy, with properties often featuring a rustic elegance.

  • Equestrian Properties: Given its paniolo heritage, Makawao is a prime location for equestrian estates, complete with stables, riding rings, and ample grazing land.

  • Boutique Properties: Discover charming, renovated historic homes and contemporary residences that blend seamlessly into the unique character of the town, often on larger lots offering privacy.

Key Considerations for Your Upcountry Purchase

Before investing in this distinctive region, there are a few important factors to consider:

  • Water Source: Many Upcountry properties rely on private wells or county water. Understanding the water rights and infrastructure is crucial.

  • Climate Variations: While generally cooler, specific microclimates exist. Some areas receive more rainfall or experience more fog than others. A site visit is essential.

  • Access & Infrastructure: Roads can be winding, and some estates are more remote. Understanding internet and utility access is important, though many luxury estates are highly self-sufficient.

  • Permitting for Agricultural Use: If you envision a working farm or extensive agricultural operation, understanding local zoning and permitting processes will be key.

Your Gateway to Elevated Living

Upcountry Maui represents a unique facet of luxury living—a profound connection to the land, unparalleled privacy, and a refreshing escape from the coastal bustle. It’s a place for those who seek beauty, tranquility, and a bespoke lifestyle.

If you are drawn to the allure of cooler climates, panoramic views, and expansive estates, I invite you to contact me. With decades of experience across all of Maui's luxury enclaves, I can expertly guide you to your perfect Upcountry sanctuary.

Riette Jenkins
REALTOR® Broker | RB-17543
Managing Director of Global Luxury
Coldwell Banker Island Properties

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Their industry specialities include luxury homes, relocations, estate sales and investment properties. With 16 years of experience in the real estate industry, she has been through multiple market cycles as an agent, buyer and investor, and has a deep understanding for the often-complicated process that her clients will encounter.

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