Twisting along Maui’s rural northwest coastline, Kahekili Highway is truly a road less traveled, even on an island that attracts roughly 3 million visitors each year. The road carves into rugged cliffs and lush valleys, winding past waterfalls, hiking trails and panoramic views that sweep from the sea to summit of Haleakala. 

Stop at farm stands to buy fresh produce, flowers and some of Maui’s best banana bread, or gaze upon verdant pastures of grazing cattle. And if you follow the road just 15 minutes down past Wailuku, you’ll find a different slice of paradise: Hale Wainui.

Situated on 51 acres of pristine acreage, Hale Wainui is the epitome of luxury island living. Built with only the finest furnishings and craftsmanship, the

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Island Sotheby’s International Realty is proud to present one of the rarest offerings ever to come to market: a breathtaking getaway on one of South Maui’s most exclusive white-sand beaches.

With four bedrooms, five and a half bathrooms and 5,065-square-feet of living space, this newly-constructed, fully-furnished home offered for $29.98 million is one of the finest in Makena, an area known for being home to some of the most extraordinary properties in Hawaii. Constructed out of the highest quality materials from across the world, this home was created with the utmost attention to detail, with interior living spaces that seamlessly blend into expansive covered lanais.

“The master level of craftsmanship and thoughtful design throughout the

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Island Sotheby’s International Realty agents are representing what could be the largest sale ever for a single-family home on Maui.

Realtors Courtney Brown, R(S) and Rob Shelton, R(B) are representing the owners of a sprawling 10-acre oceanfront estate, equipped with its own small lighthouse, that’s offered for $49 million. If it sells for that price, it would break Maui’s current record of a single-family home, which is currently held by a $41.8 million home sold in 2015, according to the Maui Association of Realtors.

This once in a lifetime property has already garnered national attention, including that of the Wall Street Journal and Mansion Global. That’s no surprise: The estate boasts more than 12,000 square feet of indoor-outdoor living

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Privacy. Tranquility. Nature.

This 5.8 acre estate nestled in the lush slopes of Haleakala has it all. With an idyllic country setting and sweeping coastal views, this property offered for $2.999 million boasts every feature — both natural and man-made — that a buyer would want in their ultimate private retreat.

“What makes this property special is the location,” said Island Sotheby’s International Realty agent Megan Bouhey R(S), who’s representing the seller. “It is a short trip to civilization, but feels like you are on top of the world.”

Bouhey explained that the property was once owned by famed country singer Randy Travis. Located in one of Kula's most desirable neighborhoods, this manicured estate borders ranch land, thus

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Experience the best of Maui resort living - privacy, breathtaking ocean views and luxury amenities in the heart of Wailea.

Island Sotheby’s International Realty is representing the sellers of one of Wailea’s finest units - Wailea Point Unit 102. With an asking price of $25 million, this condominium is the epitome of prestigious vacation living in one of Maui’s most coveted communities.

Wailea Point is perfectly situated above Wailea Beach, offering breathtaking ocean vistas that include multiple Hawaiian Islands like Kaho’olawe and Molokini. Just steps from the community, guests and residents can explore premiere hotels including the Four Seasons Resort, Grand Wailea and Andaz.

The three-bedroom condominium boasts 3,850 square feet of

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There are few properties in the Hawaiian Islands that rival the natural beauty found at this Makena estate.

Perched on the point of Makena Place, this jewel recently sold for $9.3 million in one of South Maui’s most coveted oceanfront communities. Island Sotheby’s International Realty agent Wendy Peterson R(S) was one of the listing agents who facilitated the sale of this magnificent home. 

“Makena Place is just extremely special,” said Island Sotheby’s International Realty agent Wendy Peterson. “This residence is on the point and has an unobstructed five-island view.”

With four bedrooms and three-and-a-half bathrooms, this beautifully-designed estate provides magnificent vistas of the azure Pacific Ocean and islands that span

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Traveling down the carriage driveway to H.A. Baldwin’s Olinda vacation home is truly like going back in time.

Perched atop the slopes of Haleakala, this historical 60-acre estate was once the vacation home for one of Maui’s most influential families. The home was built in 1912 by Henry Alexander Baldwin, a sugarcane plantation manager and politician who served as congressional delegate during Hawaii’s territorial era.

“When you walk in, it's like you're stepping back into the 1920s or the 1930s,” said Wendy Peterson, the Island Sotheby’s International Realty agent who’s representing the seller.

This timeless property looks as if it’s out of a storybook, with 6,000 square feet that includes spacious living areas, verandas, six bedrooms

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Rock star Pat Benatar and her guitarist husband Neil “Spyder“ Giraldo are offering their secluded Hana estate for $3.6 million.

The oceanfront home perches atop a private cove that's minutes from the sleepy town of Hana. As recently featured in Wall Street Journal and Mansion Global, the famed couple lived there full time with their two daughters for several years until about 2009. Island Sotheby’s International Realty agents Dan Omer and Megan Bouhey are listing the home, which offers breathtaking views that sweep from the Big Island to Haleakala crater. 

Hana is known as one of Maui’s most pristine jewels with dozens of waterfalls, freshwater pools and hiking spots scattered throughout the area. Located minutes away from Waioka Pond — also

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  Imagine. Maui. This exceptional vintage garden view one bedroom two bath townhome with a spacious loft is ideally located in the historic district of Lahaina. Pumana 8-1 listed by Lori Powers, R(S) and Anita White, R(B), offers a unique community that is a quiet oasis of 30 oceanfront acres of tropical gardens and swaying palm trees. Your day begins with the morning beverage of choice on your private lanai. Your residence has views of the West Maui Mountains, where the sun rises, and at sunset enjoy the neighborhood gathering place in front of the Puamana Clubhouse where homeowners and guests mingle and watch the spectacular sunsets. For those interested in exploring the Lahaina real estate market and available opportunities, visit our West Maui…

  Beautifully maintained 2 bedroom, 2 bathroom unit at Wailea Elua 705. Listed by Ryan MacLaughlin, R(B) and Paul MacLaughlin, PB offering two patios allowing one to enjoy wonderful sunrises and sunsets. This unit is one of only a select few in the complex that has an oversized garage. Situated conveniently a short distance from the pool, beach and fitness center, come and enjoy this “neat as a pin” Condominium Unit. For those interested in exploring the Wailea real estate market and available opportunities, visit our Wailea office located in the Shops at Wailea at 3750 Wailea Alanui Dr. Ste. B34 or call us at 808.879.8880.