The 7 dreamiest multimillion dollar properties currently for sale on Maui

Are you thinking about acquiring a piece of paradise?

After perusing the current real estate listings on the market, we found some of the finest, dreamiest, most exclusive homes and properties we’ve ever seen!

Without further ado, we present our top seven:

Kapalua beachfront estate – 6 BD / 6.5 BA – $18.9M

With an estimated monthly mortgage payment of $67,674, this jaw-dropping beachfront home in Kapalua appears to be worth every penny. The opulent furnishings are included, as are the glass doors from Italy, the floating staircase and the Kapalua blue rock walls.

From most rooms in the house — or the pool — you get views of Oneloa Bay, Molokai and the breaching humpback whales in the winter.

See more Kapalua beachfront estate photos

Makena one acre on coastline – 8BD / 8.5BA – $26.9M

Makena is arguably the best spot to be in all of Maui, which explains why this giant 10,000 sq. ft. home is stunning with a touch of magic. The custom woodwork frames each room with depth and character. Enjoy a outdoor movie theater, 4,000 sq.ft. deck, en epic lawn overlooking the pool and of course — world-class views of the ocean and neighbor islands.

The other bonus: the property sits on one acre, and it’s right across street from the ocean.

See more photos of 1 acre property at Makena

Kihei – Keawakapu beachfront on 1/2 an acre – 9BD / 10BA – $24M

With a recent price drop of $2.9M, this 13,422 sq. ft. home on Keawakapu beach in South Maui is now listed at $24,000,000 — a total steal. Aside from privacy and ocean views, you get options: ten bathrooms, nine bedrooms, and half an acre of land to roam around.

Let’s not forget the interior: three ocean view master suites, five guest bedrooms (all en suite), a couple of powder rooms and quarters for a live-in caretaker. And artwork.

See more Keawakapu beach house photos

Wailea Point oceanfront condo – 3BD / 3BA – $25M

The town of Wailea is one of Maui’s most exclusive, which makes this $25M condo at Wailea Point the cream of the crop. Ocean views are the norm, of course, as are the views of Kahoolawe and Molokini and the upscale resort scene at neighboring Wailea Beach.

Inside, 25-foot high ceilings create a cathedral of open space, while a moveable wall of seamless windows allow you to break down the boundaries of inside and outside. Did we mention the views?

See more oceanfront at Wailea Point estate photos

Wailuku Upcountry estate on 5.75 acres – 5BD / 5.5BA – $14M

Okay, maybe beachfront isn’t your thing (or you already have a beachfront home).  If that’s the case, head upcountry to Wailuku, to the slopes of Mount Kahalawai, to this 10,300 sq. ft. stroke of architectural genius and spectacular views of Haleakala and the Pacific Ocean.

The home is designed through the lens of the California Mission revival style, with dramatic coffered ceilings, a chef’s kitchen, a four-car garage and master and guest en suites. Let’s not forget the nearly six acres of property, too, which include a swimming pool, and an oasis of endemic, indigenous plants.

See more upcountry Wailuku sprawl photos

Lower Kula upcountry 2 acres – 4BD / 4.5BA – $3.9M

Another upcountry jewel, this time in the desirable elevations of Kula: a meticulously designed and crafted family home with full wet bar, arcade room, pool table and a large screen movie theater. We should also mention the infinity pool and jacuzzi, private tennis court and “tennis observation dome.”

The living areas are equally classy, with bicoastal ocean views from the master bedroom, a mahogany library/office, wood and marble floors, a wet bar and lanais throughout that lead to the swimming pool. Also included is a two-bedroom guest house with an oceanview lanai.

View more Lower Kula estate photos

Own 35% of Molokai – 55,575 acres – $260,000,000

We had to write out the full number for this one: $260 million for over one-third of the island of Molokai!

The property is known as Molokai Ranch — technically part of Maui County — and comes with two hotels, two golf courses, 20 miles of coastline, nature preserves, and thousands of acres of oceanfront, interior and agriculture land, as well as commercial, residential and industrial properties.

And Honolulu is just 30 minutes away by private air charter — which is faster than it takes with traffic!

Purchase 35% of Molokai

Need a hand with your next Maui vacation? Please contact the Sunny Maui Vacations team at or call 808-240-1311, ext. 21. We’ll find you the best vacation rental condo in South Maui and help you with any and all recommendations and activities across Maui (chat with our in-house Concierge at extension 71).

Photo credits Hawaii Life and Sothebys International Realty

Need a hand with your next Maui vacation? Please contact the Sunny Maui Vacations team at or call 808-240-1311, ext. 21. We’ll find you the best vacation rental condo or rental home in South Maui and help you with any and all recommendations and activities across Maui.