Living in Maui Meadows: Inside 557 Kupulau Drive, One of South Maui’s Most Extraordinary Homes

There are plenty of beautiful homes on Maui.

Then there are properties where the architecture, location, views and lifestyle all come together in a way that makes you stop and say:

This is why people dream about living on Maui.

557 Kupulau Drive in Maui Meadows is one of those homes.

Currently offered at $5,000,000, this private South Maui estate features 4 bedrooms, 4 bathrooms, approximately 3,447 square feet of interior living space and roughly 0.57 acre of land. But those numbers barely begin to explain the property.

The real story is the architecture.

The panoramic Pacific Ocean views.

The indoor-outdoor living.

The pool and spa.

The privacy.

And perhaps most importantly, the ability to have all of that while living just above Kihei and Wailea, with beaches, restaurants, shopping, golf and some of Maui's best resorts just down the hill.

This isn't simply a house in Maui Meadows.

It's a private resort above South Maui.

View 557 Kupulau Drive — photos and full property details

What Is It Like to Live in Maui Meadows?

Maui Meadows is a residential neighborhood located on the hillside above Kihei and Wailea in South Maui. Buyers are drawn to the area for larger properties, privacy, elevation and ocean views while remaining close to South Maui beaches, restaurants, shopping, golf and the amenities of Wailea.

That combination is what makes Maui Meadows so interesting.

There are places on Maui where you can get privacy and land.

There are places where you can be close to beaches, restaurants and resorts.

Finding both is harder.

Maui Meadows gives you the opportunity to live above the action without being removed from it.

You can spend the afternoon at the beach.

Have dinner at a world-class restaurant in Wailea.

And then come home to a completely different environment—more land, fewer people around you and panoramic views across the Pacific.

That's a pretty incredible way to live.

Why Maui Meadows Is One of South Maui's Most Unique Neighborhoods

Maui Meadows isn't a cookie-cutter subdivision.

That's one of the things I like about it.

Homes vary dramatically in architecture, size, age, lot configuration and views. You'll find everything from older Maui residences to remodeled estates and substantial luxury properties.

And because of the neighborhood's hillside location, certain properties have spectacular elevated ocean views.

But there's another major advantage:

Location.

You're immediately above Kihei and Wailea.

That means Maui Meadows can provide the privacy of an estate-style neighborhood without forcing you to give up the lifestyle that makes South Maui so desirable.

For buyers comparing communities around the island, that's an important distinction.

Our guide to Living in Wailea explains why South Maui has become such a desirable place to own property.

Maui Meadows gives you access to much of that lifestyle—but from your own private hillside retreat.

557 Kupulau Drive: The Resort in Maui Meadows

That's where 557 Kupulau Drive separates itself.

The property has been appropriately nicknamed:

The Resort in Maui Meadows

And once you see it, you'll understand why.

The residence is positioned above the coastline with expansive Pacific Ocean and neighboring-island views. Its open-concept design, oversized lanais and indoor-outdoor gathering areas were created to take advantage of both those views and Maui's climate.

This isn't a house where someone stuck a couple of chairs on a lanai and called it "indoor-outdoor living."

The architecture actually revolves around it.

The interior spaces transition naturally outside.

The ocean becomes part of the backdrop.

The pool feels connected to the home.

And instead of having one designated spot where you go to see the view, the view follows you through much of the property.

That's a completely different experience.

Architecture Designed for Maui

One of the things I think buyers sometimes underestimate is how important architecture becomes when you're purchasing a luxury home in Hawaii.

You can build the same generic house almost anywhere.

But the best Maui homes feel like they belong here.

557 Kupulau does.

Large openings, expansive lanais, gathering spaces and open sightlines allow the house to interact with its surroundings rather than shut them out.

That's exactly what good island architecture should do.

You're not simply looking at the Pacific through a window.

The ocean becomes part of the house.

You're cooking with it in the background.

You're entertaining with it behind you.

You're waking up to it.

And at the end of the day, you're watching the sky change over it.

The architecture isn't competing with Maui.

It's framing Maui.

Some Ocean Views Are Different From Others

This is something that's difficult to appreciate online.

An ocean view from elevation is completely different from an ocean view at sea level.

In Maui Meadows, you're looking over South Maui and across the Pacific.

The perspective is enormous.

At 557 Kupulau, the property's elevated position creates sweeping views stretching toward Maui's neighboring islands, with the ocean providing a backdrop from much of the residence.

During the day, you've got blue Pacific.

Toward evening, you've got Maui sunset.

And once it gets dark, you've got the lights of South Maui below you.

The view changes constantly.

That's one of those things pictures can show you.

But they can't really make you feel it.

This House Was Built to Entertain

If you enjoy having people over, this property gets even more interesting.

The chef's kitchen anchors the primary entertaining area, while the open floor plan connects the interior gathering spaces with the oversized lanais and outdoor areas.

You could have a quiet dinner with a few friends.

Or you could throw one hell of a party.

Both work.

And that's the beauty of a well-designed luxury home.

It doesn't only impress people when they walk through it.

It functions.

People can gather around the kitchen.

Others can move outside.

Someone is in the pool.

Someone else is sitting on the lanai.

And the entire property still feels connected.

On Maui, that's how a house should entertain.

Your Own Private Resort

Of course, we have to talk about the pool.

Because this is where the "Resort in Maui Meadows" idea really starts making sense.

The pool and spa sit within lush tropical surroundings and extensive outdoor living areas, creating a setting that feels less like a backyard and more like a private retreat.

And privacy changes everything.

You don't need a resort wristband.

You don't need to find a lounge chair.

You don't have a hundred people sharing the pool.

It's yours.

Wake up and swim.

Spend the afternoon outside.

Have friends over.

Pour a drink.

Watch sunset.

Stay exactly where you are.

There are certainly spectacular resorts in Wailea.

But there's something pretty appealing about being able to enjoy Wailea whenever you want—and then come home to your own resort.

More Than Half an Acre in South Maui

557 Kupulau sits on approximately 24,916 square feet, or 0.57 acre.

On Maui, land matters.

In South Maui, it matters even more.

The additional space provides room for tropical landscaping, outdoor living and separation from neighboring properties.

And there's an intangible benefit that's difficult to quantify:

breathing room.

When you drive through many densely developed parts of South Maui, homes can sit relatively close together.

Maui Meadows feels different.

At a property like this, you aren't simply buying a house.

You're buying the environment around the house too.

The Detached Ohana Adds Even More Flexibility

557 Kupulau is classified as a single-family property with a detached ohana or cottage.

That's another major advantage for the right owner.

Maybe you've got family coming to Maui.

And if you live here long enough, trust me—they're coming.

Maybe you want guest accommodations.

Maybe you need workspace.

Maybe you have extended family.

Whatever the intended use, additional detached space can give a Maui property flexibility that a traditional single-residence layout simply doesn't have.

Buyers should, of course, independently verify permits, zoning and allowable uses for any additional dwelling or structure.

Luxury Living Without Giving Up Convenience

This might be my favorite argument for Maui Meadows.

You're living on more than half an acre.

You've got privacy.

You've got an ocean view.

You've got your own pool.

It feels like you're away from everything.

Except you're not.

Kihei and Wailea are right below you.

Beaches.

Restaurants.

Shopping.

Golf.

Resorts.

Coffee.

Groceries.

Everyday services.

That's the part of luxury real estate people don't talk about enough.

Privacy is fantastic.

But being private and convenient is better.

Some of Maui's Best Dining Is Right Down the Hill

Here's where living in Maui Meadows gets really fun.

You can spend the afternoon at your own pool, shower, head down the hill and have dinner at some of Wailea's best restaurants.

For a special evening, The Restaurant at Hotel Wailea is one of the standouts. Sitting above Wailea, the restaurant offers open-air dining with panoramic ocean views and emphasizes seasonal ingredients sourced from Maui farms and fishers. Hotel Wailea also offers private experiences including its Chef's Table, Garden Table and Treehouse dinner.

Explore The Restaurant at Hotel Wailea

Then there's Spago at the Four Seasons Resort Maui at Wailea.

It's Wolfgang Puck's upscale Wailea restaurant, pairing Hawaiian ingredients with Pacific and California influences in an ocean-view setting. It's exactly the type of restaurant that makes having Wailea right down the hill such a luxury.

For oceanfront Italian, Ferraro's Restaurant & Bar at the Four Seasons is another great option. Its open-air, sunset-facing setting combines coastal Italian cuisine with Hawaiian seafood and produce.

And now you've got Nobu Grand Wailea.

Nobu brings Chef Nobu Matsuhisa's Japanese-Peruvian style to more than 13,000 square feet of indoor and alfresco space overlooking the ocean at Grand Wailea. Signature offerings include Black Cod Miso and Yellowtail Jalapeño, and OpenTable named it among its Top 100 Hotel Restaurants in America for 2026.

Explore Nobu Grand Wailea

And sometimes you don't want a formal $500 dinner.

For something more relaxed, you've got Monkeypod Kitchen by Merriman - Wailea, Maui at Wailea Gateway, along with numerous other restaurants throughout Wailea and Kihei.

That's the lifestyle advantage.

Dinner at Nobu tonight. Spago next weekend. Sunset cocktails at Hotel Wailea. Or don't leave 557 Kupulau at all.

Because Staying Home Might Be Better

This is where this particular property changes the equation.

When your own house has panoramic ocean views, a chef's kitchen, expansive lanais, tropical landscaping, a pool and spa and enough space to entertain…

Going out isn't always the better option.

Pick up great food.

Open a bottle of wine.

Invite friends over.

Turn on some music.

Get in the pool.

Watch the sun disappear into the Pacific.

You aren't trying to recreate the Maui resort experience.

You're living your own version of it.

That's why I think "Resort in Maui Meadows" fits this property so well.

How Close Is Maui Meadows to Wailea?

Maui Meadows is located immediately above South Maui's Kihei and Wailea resort areas, allowing residents to live in a more private, lower-density residential setting while maintaining convenient access to Wailea's beaches, restaurants, shopping, resorts and golf courses.

This is one of the neighborhood's strongest selling points.

You're not living inside the resort environment.

You're living above it.

For buyers trying to decide between the different South Maui lifestyles, I recommend reading our complete guide to Living in Wailea: Resort Living Without Sacrificing Everyday Life.

The comparison is interesting.

Wailea gives you resort living.

Maui Meadows gives you proximity to resort living with considerably more opportunity for land and privacy.

Is Maui Meadows Close to the Beach?

Yes. Maui Meadows sits directly above the South Maui coastline, giving residents convenient access to beaches throughout Kihei and Wailea while allowing them to live outside the denser coastal and resort areas.

That's a major distinction.

You don't have to live directly across the street from the ocean to make the beach part of your everyday life.

Want to spend the morning at Keawakapu?

Go.

Want to catch sunset at Kamaole?

Go.

Want to spend the afternoon in Wailea?

Go.

Then drive back up the hill.

Your pool is waiting.

What Does $5 Million Buy in Maui Meadows?

557 Kupulau provides a pretty spectacular current example.

At its $5,000,000 asking price, the property offers:

• 4 bedrooms
• 4 bathrooms
• Approximately 3,447 square feet
• Approximately 0.57 acre
• Panoramic Pacific Ocean views
• Pool and spa
• Detached ohana/cottage
• Expansive indoor-outdoor entertaining areas
• Chef's kitchen
• Seller-owned photovoltaic system
• Solar hot water
• Four covered parking spaces
• Tropical landscaping
• Proximity to Kihei and Wailea

But there's something important about evaluating luxury Maui real estate:

Price per square foot doesn't tell the whole story.

How do you put a price per square foot on a sunset?

Or privacy?

Or architecture?

Or half an acre?

Or the way the ocean looks from your lanai?

At this level, buyers aren't simply comparing bedroom counts.

They're comparing experiences.

They're asking:

How difficult would this property be to recreate somewhere else?

That's where special homes separate themselves from ordinary ones.

Is Maui Meadows a Good Place to Live?

Maui Meadows can be an exceptional place to live for buyers who want larger properties, privacy and elevated ocean views while remaining close to Kihei and Wailea. It is particularly attractive to buyers who want an estate-style residential setting without giving up easy access to South Maui beaches, restaurants, shopping, golf and resorts.

It's not necessarily right for everybody.

If your dream is walking out of an oceanfront condo and being on the sand in two minutes, there are better choices.

If you want a gated resort community, look at Wailea.

If you want acreage and cooler weather, let's talk about Kula.

But if you tell me:

Todd, I want privacy.

I want some land.

I want an incredible ocean view.

I want a pool.

And I still want Wailea and the beach right down the hill.

Then we're going to talk about Maui Meadows.

What Should Buyers Know Before Buying in Maui Meadows?

Buying an estate-style property requires different due diligence than buying a resort condominium.

Depending on the property, buyers should investigate issues including permits, wastewater systems, water service, drainage, access, additional dwellings, solar equipment, insurance, landscaping requirements and any applicable zoning restrictions.

You should also think about something less technical:

How are you actually going to live?

Don't buy an acre because an acre sounds impressive if you don't want to maintain it.

Don't buy an oceanfront condo because "oceanfront Maui" sounds incredible if you really want privacy.

Don't buy Upcountry if you want dinner in Wailea every night.

And don't overlook Maui Meadows if you're trying to find the middle ground.

Buying the right Maui property starts with understanding the lifestyle you actually want.

Frequently Asked Questions About Maui Meadows Real Estate

Where is Maui Meadows?

Maui Meadows is a residential area located on the hillside above Kihei and Wailea in South Maui. Its elevated location allows many properties to offer ocean views while remaining convenient to the South Maui coastline.

Is Maui Meadows part of Kihei?

Maui Meadows homes generally use Kihei mailing addresses. 557 Kupulau Drive has a Kihei address and is identified as being in the Maui Meadows subdivision.

Does Maui Meadows have ocean views?

Many Maui Meadows properties have ocean views because of the neighborhood's elevation, although every lot is different. 557 Kupulau Drive is particularly notable for its sweeping Pacific Ocean and neighboring-island views.

Is Maui Meadows close to Wailea?

Yes. Maui Meadows sits above South Maui near the Wailea resort area, making access to Wailea beaches, restaurants, golf, resorts and shopping one of the neighborhood's major lifestyle advantages.

Are Maui Meadows lots larger than typical Kihei properties?

Many properties in Maui Meadows offer substantial lot sizes compared with Maui's denser residential and condominium areas. Lot sizes vary considerably from property to property.

Is Maui Meadows considered luxury real estate?

Maui Meadows includes a broad range of properties, including substantial luxury estates. Buyers looking for ocean views, larger lots and privacy near Wailea often include Maui Meadows in their South Maui search.

Is 557 Kupulau Drive for sale?

Yes. As of this writing, 557 Kupulau Drive is offered at $5,000,000. The property features 4 bedrooms, 4 bathrooms, approximately 3,447 square feet of interior living area and approximately 0.57 acre.

See the complete 557 Kupulau Drive listing and photos

A Different Kind of South Maui Luxury

Luxury means different things to different people.

For some people, it's an oceanfront penthouse.

For someone else, it's walking to Wailea Beach.

For someone else, it's five acres in Kula.

At 557 Kupulau Drive, luxury is different.

It's waking up above South Maui with the Pacific stretched out in front of you.

It's having enough land that your home feels private.

It's opening the house to the outdoors.

It's having friends over without feeling crowded.

It's having your own pool and spa.

It's being able to head down the hill for dinner at Spago or Nobu—and come home to peace and privacy afterward.

And it's having a house with enough architectural character that the property itself becomes part of the Maui experience.

That's the Resort in Maui Meadows.

Experience 557 Kupulau Drive

There are houses you can understand from pictures.

I don't think this is one of them.

You need to stand on the property.

You need to see how wide the ocean view actually feels.

You need to experience the relationship between the architecture, lanais and outdoor spaces.

You need to walk around the pool.

And preferably, you need to be there when the sun starts dropping over the Pacific.

If you're looking for a luxury home in Maui Meadows, Wailea, Kihei or South Maui, I'd put this one on the list.

Explore 557 Kupulau Drive — full listing and photos

557 Kupulau Drive | Maui Meadows
Offered at $5,000,000
4 Bedrooms | 4 Bathrooms | 3,447 Sq. Ft. | 0.57 Acre

About Todd Hudson

Todd Hudson is a Maui Realtor® and Broker with The 808 Team at Keller Williams Realty Maui, ranked among the Top 1% of real estate professionals in Hawaii by sales volume. Todd works with buyers, sellers and investors throughout Maui, with experience in luxury homes, residential real estate, condominiums, investment properties and vacation-rental real estate.

My job isn't simply to show you houses.

It's to help you understand where and how you want to live on Maui—and then find the property that delivers it.

Todd Hudson, REALTOR® | Broker
The 808 Team | Keller Williams Realty Maui
Call/Text: 808-344-3584
Email: Todd@The808Team.com