On Maui, homes are where generations gather, families grow, and everyday life blends seamlessly with the island’s natural beauty. Increasingly, buyers are seeking residences that can adapt to their evolving needs. Islandwide, buyers are prioritizing spaces that evolve with real life: guest-ready suites for visiting loved ones, hybrid rooms that move from focused office to creative studio, and separate ohana units (accessory dwellings) that preserve privacy and comfort. Versatility isn’t a perk in today’s market—it’s the standard that turns every square foot into possibility.

Here are four extraordinary properties across the island that showcase the very best of multi-generational living and flexible design.

20 Kapuaimilia Place, Haiku

Wailea, Maui, is world-renowned for its golden beaches, sparkling waters, and luxury living. But beyond its breathtaking beauty, Wailea is also home to four of Maui’s most exceptional resorts: the Four Seasons Resort Maui at Wailea, the Andaz Maui at Wailea Resort, Grand Wailea, A Waldorf Astoria Resort and the Fairmont Kea Lani. Each of these destinations offers much more than overnight accommodations. From indulgent spas and award-winning restaurants to pool day passes and oceanfront adventures, these resorts create unforgettable experiences for visitors and locals alike.

Here’s your insider’s guide to the best ways to enjoy Wailea’s luxury resorts—whether you’re planning a vacation or looking for a rejuvenating staycation on the Valley Isle.

Towering over Maui at 10,023 feet above sea level, Haleakala National Park offers one of the most awe-inspiring experiences on the island. Known as the “House of the Sun,” the summit is a place where sky, clouds, and volcanic landscapes collide to create moments that feel truly otherworldly. Whether you start your day watching the sun rise above the clouds or end it soaking in a fiery sunset, visiting Haleakala is one of Maui’s bucket-list adventures.

This local’s guide will walk you through how to plan your perfect Haleakala day, from securing reservations and finding the best hikes to knowing where to grab food before or after your visit.

Option 1: A Sunrise Adventure 

Make Your Reservation 

Sunrise at Haleakala is one of Maui’s most

Island Sotheby’s International Realty is excited to welcome Mark Janes RS-86830 to our team! A seasoned professional whose unique blend of Silicon Valley business acumen, hands-on homebuilding experience, and passion for Maui living sets him apart in the luxury real estate market. With over 30 years in real estate and development, Mark brings a detail-driven, strategic approach to helping clients create and discover their own piece of paradise. We sat down with him to learn more about his journey, his love for Maui, and what makes his approach truly one-of-a-kind.

What led you to where you are today?

I spent over a decade in Silicon Valley building startups and honing skills in design, project execution, and strategic thinking. Now, with more

Along the lush North Shore of Maui, Haiku is a place where the pace slows down, the air feels fresher, and every view is a brushstroke of natural beauty. Known for its rolling green hills, misty mornings, and a creative spirit that seems to hum through the trees, Haiku invites you to live both intentionally and luxuriously. It's no wonder that some of Maui’s most striking modern homes are located right here, and two extraordinary properties currently on the market offer a rare chance to experience this lifestyle for yourself.

Whether you're drawn to mid-century charm reinvented for today or a sleek architectural marvel designed with gallery-like precision, both of these Haiku homes deliver a modern escape rooted in the island's soulful beauty.

There’s something magnetic about the island of Maui. From oceanfront elegance to Upcountry charm, Maui offers a lifestyle that seamlessly blends tranquility with sophistication. Today, we’re taking a closer look at two incredible homes currently on the market, each uniquely modern in design, yet connected by the effortless island lifestyle they offer.

3857 Waakaula Place | Wailea Golf Estates

Represented by Ryan MacLaughlin RB-21325 & Alex Cortez RB-21828

Tucked behind the gates of Wailea Golf Estates, 3857 Waakaula Place is a private sanctuary that elevates everyday living into something extraordinary. Perched alongside the lush fairways of the Wailea Blue Golf Course and positioned to maximize panoramic ocean views, this 4-bedroom,

On the sun-kissed coastline of West Maui where the waves meet the land and the trade winds carry the whispers of history, there grows a tree that holds more than just fruit—it holds a story. The breadfruit tree, or ‘ulu, is a symbol of life, resilience, and cultural memory in Hawai‘i, and perhaps nowhere is this more true than in Lahaina, the beloved town once known as Lele.

For centuries, ‘ulu has nourished families, shaded generations, and rooted itself deeply into the stories and soil of West Maui. Its wide green leaves and generous fruit have offered not only sustenance, but shelter, medicine, and meaning. Today, in the wake of hardship, this remarkable tree is making its quiet return, restoring not just the landscape but the spirit of a

When it comes to finding the perfect place to call home, pet parents know that it isn’t just about the view or the square footage…it’s about lifestyle. South Maui is a dream destination not only for humans but for their four-legged companions as well. With miles of walkable coastline, dog-welcoming beaches, and local businesses that roll out the red carpet for pups, South Maui is a haven for those who want to share their Hawaiian lifestyle with their furry family members.

From open-air restaurants to scenic trails and beaches where tails wag freely, we’ve rounded up the ultimate list of where you and your dog can enjoy life to the fullest.

1. Keawakapu Beach 

End of South Kihei Rd, (From Hwy 31 aka Piilani Hwy, turn off between mi 9.6 & 10.4)

Upcountry Maui is a place where rolling pastures meet panoramic ocean views, where volcanic slopes nourish generations of farmers, and where food isn’t just a meal—it’s a story of place, people, and passion. From historic general stores to modern zero-waste kitchens, Upcountry’s farm-to-table scene is a rich tapestry of locally sourced ingredients and unforgettable flavors.

Whether you’re a Maui resident or visiting for the first time, here are seven can’t-miss spots to savor the best of Upcountry Maui’s culinary bounty—all grounded in sustainability, community, and true island hospitality.

Haliʻimaile General Store

900 Hali'imaile Rd, Makawao
Hours: Daily 11:00 AM–8:00 PM
haliimailegeneralstore.com | @haliimailegeneralstore

For

With its rolling green fairways, dramatic ocean views, and year-round sunshine, it’s no surprise West Maui has earned its reputation as one of the most iconic golf destinations in the world. Whether you’re a seasoned player chasing a championship course or a casual golfer looking to enjoy the island breeze, West Maui offers some of Hawai‘i’s most memorable golfing experiences.

From the world-renowned Plantation Course at Kapalua to the historic Royal Ka‘anapali Course, here’s your guide to four standout golf courses that define the West Maui golf scene. 

Kapalua Golf

2000 Plantation Club Dr. Lahaina, HI 96761

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Kapalua Golf is more than just a place to play—it’s a full-on island lifestyle. Tucked into the upper