All Things Maui Real Estate - maui

Kihei vs. Wailea: Which Community Is Right For You?

Kihei vs. Wailea: Which Maui Neighborhood Is Right for You?

If you're searching for real estate in South Maui, you're going to spend a lot of time comparing two communities that sit right next to each other on the map but feel like entirely different worlds when you're actually living in them.

Kihei and Wailea are both exceptional places to own property. Both offer world-class beaches, incredible weather, and easy access to everything South Maui has to offer. But they attract very different buyers, and choosing the wrong one for your lifestyle and goals can be a costly mistake.

I've sold real estate in both communities for years, and I've helped many buyers navigate this exact decision. Here's my honest take on both.

Kihei vs Wailea:…

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Buying a Second Home on Maui: Insight, Tips, Do's and Don'ts

The Complete Guide to Buying a Second Home on Maui

Buying a second home on Maui can be one of the most exciting and life-changing decisions a person can make. I've worked with a lot of second-home buyers over the years, and what I've found is that most of them have been thinking about this for a long time.

Maybe they started coming to Maui as kids, and as adults, they want to share that with their children. Maybe they fell in love with the island on a honeymoon and have always felt a connection. Maybe they've been renting for longer periods each year and have finally decided it makes more sense to own than to keep renting.

Whatever has you thinking about buying a second home on Maui, I want to share my experience and help you navigate this…

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Top 13 Vacation Rentals on Maui to Rent or Own

Maui's Best Vacation Rentals to Rent or Own

From Maui’s incredible beauty and world-class beaches to its unforgettable sunsets and breathtaking scenery, it is the ultimate destination for a tropical island getaway.

When searching for a vacation rental on Maui, either to rent or to own, most people are looking for something that combines the comforts and luxuries of home with the authentic feel of the islands.  However, with numerous vacation rentals on Maui to choose from, identifying the property that’s the best fit for you can be a little overwhelming.

After 16 years of living and working on Maui, with intimate knowledge of these complexes, I’ve put together a short list of some of the best options Maui has to offer at a variety of price…

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Does Maui Have a Water Problem?

Does Maui Have a Water Problem? 

The Hawaiian Islands occupy a unique position on Planet Earth and are subject to distinct, sometimes extreme, weather patterns. Here in the middle of the Pacific Ocean, 2,300 miles from California, Hawaii exists because of a fixed volcanic hot spot in the ocean (a deep plume of magma under the slowly moving Pacific Plate) that has been flowing for millions of years and is currently creating the Big Island.

It's a miracle that life exists in Hawaii and living here in Hawaii, at least in my humble opinion, is also miraculous.

Amazingly, Hawaii Island, the largest of the chain, is still growing from its active volcanoes, while the rest of the main Hawaiian Islands, Maui, Oahu, Kauai, Lanai, Molokai, and Niihau,…

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Using a 1031 Exchange on Maui | What It Is and How It Works

Using a 1031 Exchange on Maui to Leverage Up Without Losing Your Gains to Taxes

From the stable cash flow of rental income to the exceptional growth of property value and more, Maui investment properties hold tremendous financial potential. When you sell a rental property or second home, you will ideally enjoy a handsome profit. As is the case with all types of income, Uncle Sam try to take a cut.

Depending on how much appreciation your subject property of the 1031 exchange has had, tax liabilities from selling can be substantial. So, you'll understandably want to avoid taxes, if possible, and maximize your return on your initial investment. Fortunately, you can do so legally with one of the largest wealth-building tools for real estate…

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Montage Kapalua To Become St. Regis Under Marriott Management

Montage at Kapalua to Become St. Regis 

It was recently announced that Marriott International signed a management agreement with the Tennessee-based owners of the Montage Resort at Kapalua Bay, KWC Management.

The former management agreement was between KWC Management and White Label Asset Management, who continued to operate under the Montage brand after KWC had purchased the property in November of 2023. Marriott will now operate the Resort under their luxury St. Regis Resort Division. 

The Montage Kapalua property has consistently been regarded as one of the very best resorts in the State of Hawaii, and last traded hands when Lantern Asset Management purchased it in 2013 through a foreclosure sale, after it was owned by the infamous Lehman…

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HOA Fees on Maui : Explained

HOA Fees on Maui: Explained

Homeowners’ Associations have been around in the United States since the mid-20th century. They operate as non-profit organizations whose primary objectives are to organize, maintain, and protect properties along with their owners within planned communities or subdivisions, condominium complexes, and cooperative ownership agreements. There is a wide variety of HOAs across the country, and specifically on Maui. 

Some HOAs can be very small, with only a few properties in the association, while others can involve 1,000s of homeowners. The most common type of HOA on Maui is a condominium community HOA.

There are hundreds of condo complexes on Maui, and their HOAs use the funds they collect from owners to cover things…

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14 of the Best Things to Do in Kapalua Maui

Best Things to do in Kapalua Maui

Located just north of Napili and Ka'anapali on West Maui, the luxury resort destination of Kapalua offers a relaxed vibe with world-class beaches and unforgettable experiences on land and sea.

The area provides sights, sounds and activities for all to enjoy, making it well-suited for an amazing getaway. Here are the 14 best things to do in Kapalua from someone who's done them all. 

1. Walk the Kapalua Coastal Trail 

The unforgettable Kapalua Coastal Trail is an out-and-back route covering a total of 1.76 miles each way for a total round trip mileage of 3.52 miles. This is a flat, relatively easy trail that takes roughly an hour and a half to walk.

However, with many sights and activities to enjoy…

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The Risks of Buying Real Estate on Maui and How to Navigate Them

What Are The Risks of Buying Real Estate on Maui?

Selling real estate on Maui, or anywhere for that matter, is rarely, if ever, as glamorous as the reality TV shows like Selling Sunset or Million Dollar Listing make it look.

My day-to-day life as a Realtor looks a lot more like early morning emails with 17 open tabs on my Chrome browser, hours a day in my car driving around the island for appointments or check-ins, often making the whole circuit from Upcountry to Kapalua to Wailea and back while making calls and texts, to return home, just to send a few more emails. 

The best part of my work day is when I’m with clients, either on the phone or in person. I spend the rest of my time in front of the soft glow of my iMac, moving deals forward…

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Maui STR Ban Bill 9 Exemption List and Temporary Investigative Group Report (Proposed 10/14/25)

Maui STR Ban Bill 9 Exemption List and Temporary Investigative Group Report (Proposed 10/14/25)

On October 14th, the Temporary Investigative Group (TIG) of the Housing and Land Use Committee reported the results of their findings to the public, which included a much-welcomed determination that the bill to take away STR rights of owners on the Minatoya List should include an exemption list of 53 properties that includes many Minatoya List condo complexes and a few BnB residential properties.

Most of us in the Maui community have been hoping to see some logic and reason applied to this issue.  Aside from the economic consequences of such a possible ban, there are many reasons why simply banning short-term rentals in apartment-zoned complexes won't…

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