Big Island Luxury

Representing buyers and sellers in Kona, along the Kohala Coast, and inside the island’s private oceanfront communities. Compass brokerage.

Luxury Homes For Sale

Looking for a top luxury realtor on the Big Island? Meet Penn Henderson.

A Guild Elite Luxury Specialist in West Hawaii

Big Island luxury real estate generally begins around $3M in West Hawaii and runs past $20M inside the private oceanfront communities. I am Penn Henderson, a Kona resident since 2001 and a Certified Luxury Home Marketing Specialist at the Guild Elite tier, representing buyers and sellers at that level with Compass.

At this level, the properties carry weight, the communities carry rules, and the relationships among owners, brokers, and clubs matter as much as the transaction itself. That asks for credentials taken seriously, local relationships that open doors, and discretion.

I have lived here for 25 years. Most of the doors were not opened by a designation.

Aerial of an oceanfront estate set among anchialine ponds and lava rock on the North Kona coast.
Penn Henderson, REALTOR with Compass, seated in an art filled Big Island living room.
Open air clubhouse at Kohanaiki with a koa canoe in the foreground and the ocean beyond.
Luxury FAQ
Open air living pavilion with sliding glass walls opening to a tropical garden.
Off-Market Access
Living room of a modern home opening through glass walls to the ocean at sunset.
Looking to Sell?

Explore

Big Island Private Communities and Resorts

KUkio

Aerial of the oceanfront homes and bay at Kukio on the North Kona coast.

A private equity beach club community at Kukio Bay. Exclusive, secure, and quiet by design, with a Fazio short course and full 18.

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Hualalai

Aerial of the golf course and lake at Hualalai Resort on the North Kona coast.

625 oceanfront acres anchored by the Four Seasons. Two championship courses, sports club, and spa. Estates, villas, and a few remaining lots.

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Kohanaiki

Infinity pool and daybed looking out to the ocean at a Kohanaiki home.

Invitation-only, 450 acres on the Pine Trees shoreline. Rees Jones Golf, a 67,000-square-foot clubhouse, and a members’ beach club.

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Hokulia

Aerial of an estate with lawns and pavilions above the coast at Hokulia in South Kona.

1,300 acres and three miles of South Kona oceanfront. No hotel, no commercial. Nicklaus signature golf and roughly one-acre lots.

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Mauna Kea

Aerial of the beach and surf at Mauna Kea Resort on the Kohala Coast.

The iconic resort that started it all opened in 1965 by Laurance Rockefeller. Two of the best beaches in the world sit at its front door.

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Mauna Lani

Aerial of the calm beach and bay at Mauna Lani on the Kohala Coast.

Full resort living on the Kohala Coast. Black-and-white sand beaches, two courses, and the broadest luxury price range on the island.

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+ Puako + Waikoloa Beach + Keauhou + Waimea

Unique BIG ISLAND

Luxury Homes For Sale

Penn Henderson + Compass

Access at The Luxury Level

1.

Relationships Built Over 25 Years

I know the owners, the club staff, the property managers, and the agents who quietly represent this inventory. 25 years of showing up is why I hear about properties before they are announced, and sometimes instead of.

2.

Direct Outreach on Your Behalf

When the right property does not exist on the open market, I go find it. I discreetly approach owners in the communities you are targeting. Some have been considering a sale and were waiting to be asked.

3.

Utmost Discretion, Start to Finish

Buyers at this level often want their interest kept quiet, sometimes for privacy and sometimes because visible interest moves price. I do not discuss my clients, and I do not need to explain who you are to start a conversation.

4.

Collaboration, Coast to Coast

Compass operates as one company rather than a collection of franchises, so I can reach the agent directly for any Compass listing. That matters when a mainland sale is funding your Big Island purchase.

West Hawai‘i

Where The Luxury Market Thrives

The Big Island’s luxury communities are almost entirely on the west side. The private enclaves are Hualalai, Kukio, Kohanaiki, and Hokulia. The resort communities are Mauna Lani, Mauna Kea, and Waikoloa Beach. Each has its own ownership structure, club, and rental rules.

The Kona and Kohala coastline runs roughly 35 miles, from Kailua-Kona north through Kohala. It is the sunniest, driest stretch of the island, and it is where the resorts, the golf courses, and the private clubs were built. Almost everything above $3M sits inside it.

The distinctions matter more than a map suggests. Kukio and Hualalai are equity club communities where the real estate and the membership are two separate purchases. Kohanaiki is invitation-only. Hokulia is oceanfront, with no hotel or commercial development at all. Mauna Lani and Mauna Kea are full resort communities with far broader ranges, from condos near $1M to estates well past $10M.

Which one fits depends on how you plan to use the property, how often you will be here, and whether the home needs to earn while you are away. That conversation is worth having before you start touring, and it is the first one I have with every client at this level.

The Distance Was Never a Factor

We were introduced to Penn through a trusted realtor recommendation, and even though we began working with him remotely from the mainland, the distance was never a factor. He made himself incredibly available through phone and Zoom, and he took the time to truly understand our unique needs and preferences. If you want an agent who is thorough and genuinely listens, we cannot recommend Penn highly enough.

– Srikanth R., Bayview Estates Buyer, Reverse 1031x

Aerial of Keauhou Bay with moored boats and homes along the Kona coastline.

Luxury Properties

Recently Represented

Lanai, pool and lounge seating at a home in Mauna Lani Resort on the Kohala Coast.

Mauna Lani Resort

Buyer represented | $8.2M

These buyers found me through their own research, and we worked together for over a year before we ever met. I previewed properties and sent detailed video tours until one finally resonated. They flew out within the week, and after long negotiations, we got it. I still check on the house most weeks.

Lit pool and lounge chairs at dusk beside a villa at Mauna Kea Resort.

Mauna Kea Resort

Buyer Represented | $6.7M

This started with a call from an out-of-state buyer while I was at a conference. They needed proximity to Waimea’s private schools but with access to world-class golf. I researched every area they were considering. The property was coveted, and they bought it sight unseen on my video tours.

White contemporary kitchen with an island and stools opening to an ocean view.

Kohanaiki

Seller Represented | $5.1M

A Kohanaiki property manager referred these owners to me, and we ran the entire sale remotely. I never met them in person. I coordinated the marketing, showings, and negotiations from here while they stayed where they were, and the home sold at near asking price within a few months.

Aerial of rolling green ranch country with scattered homes above Waimea.

Waimea

Buyer Represented | $3.3M

Repeat clients needed a family home near Waimea’s private schools, and inventory was tight enough that we looked at nearly everything available. Nothing worked. So I went looking off-market, made calls, and flushed out an opportunity in one of the best locations in town. That turned out to be the one.

Working With Penn

Selling at The Luxury Level

Penn Henderson monogram.

I run your sale personally.

Listings priced at roughly $3.2M or above in West Hawaii qualify for the Compass Luxury platform, a marketing layer designed for affluent and international buyers. It sits on top of the photography, video, property website, and coordinated launch that every listing I represent already receives.

1.

Wealth Mapping

Compass technology identifies the likely buyers for your specific property from a global database of high-net-worth individuals, then focuses the marketing where real demand already sits. Built around the property, not guesswork.

2.

Global Reach

Syndication across international portals in more than 50 countries, supported by a native Chinese-language site reaching one of the most active buyer pools for Hawaii real estate. For Big Island luxury properties, your likely buyer is rarely local.

3.

Luxury Channels

Placement on luxuryatcompass.com, feature consideration in the Compass Luxury newsletter and Curated magazine, and amplification through the Compass luxury social media built for this audience.

4.

Luxury Agent Network

One-click promotion to thousands of Compass luxury agents nationwide, direct to the people who already represent affluent buyers and know which of their clients is looking at Hawaii.

These channels run on top of my hands-on service, not in place of it. I manage the strategy, the assets, and the relationships.

My Selling Process Luxury Selling Guide

FAQ

Common Questions About Big Island Luxury Real Estate

The threshold moves with the market, but in practice, the luxury conversation here starts around $3 million, and the resort and club communities run well past it. The 2025 Kohala Coast median for houses was $4,900,000. Mauna Kea came in at $6,200,000 and Mauna Lani at $6,075,000. The private club communities of Hualalai, Kukio, and Kohanaiki generally open near $5 million and climb into eight figures. Price is only part of it. What defines this market is scarcity, since the properties that matter here are irreplaceable positions rather than comparable inventory.

Almost entirely in West Hawaii, along about forty miles of leeward coast. The Kohala Coast is home to three resort communities: Waikoloa Beach, Mauna Lani, and Mauna Kea. North of the airport sit the private club communities, Kohanaiki, Hualalai, and Kukio. South of Keauhou is Hokulia, agricultural and low-density on a different model entirely. Puako and Kohala Ranch offer oceanfront and large acreage outside any resort structure. Each attracts a genuinely different buyer, and the properties photograph more similarly than they do in person.

Land, mostly. You can still buy acreage with an ocean view here at numbers that no longer exist on the other islands, and the private club communities on this coast offer a level of space and privacy that Maui and Oahu cannot match at any price. The island is also less developed and less crowded, with a real working economy rather than a purely resort one. What you give up is direct flight availability and some infrastructure. Buyers who have looked at all three islands tend to arrive here for space and stay for the pace.

A meaningful share, and it grows as prices rise. At the top of this market, sellers frequently prefer discretion, and properties trade through relationships and quiet outreach rather than public marketing. That is why the agent you work with matters more here than at any other price point. Being on this coast, knowing which owners are considering a move, and being in regular contact with the agents who represent them is how you hear about things before they exist publicly. If you are only shopping what is on Zillow, you are seeing a fraction of it.

At Hualalai, Kukio, and Kohanaiki, real estate ownership is tied to club membership, which carries its own initiation contribution and annual dues, all of which are entirely separate from the purchase price. Those figures are substantial and disclosed through the club rather than published. Hokulia and the Kohala Coast resorts work differently, with varying membership structures. Puako and Kohala Ranch have no club at all. This is one of the largest variables in your true cost of ownership, and I get the membership documents in your hands early rather than late.

Sometimes, and rarely enough to be the point. The Kohala Coast resorts have established rental programs, and several condominium projects have operated them for decades. Private club communities restrict short-term rentals to protect the member experience, and single-family homes are generally more limited than attached inventory is everywhere. At this level, rental income typically offsets carrying costs for owners who are here part of the year rather than driving the purchase. If income is central to your thinking, I will tell you honestly which communities are worth your time and which are not.

Many transactions here are cash, and that shapes the negotiating landscape more than buyers expect. For financed purchases, you are in jumbo territory with underwriting that varies significantly by lender, and Hawaii-specific factors including CPR ownership, leasehold, condotel classification, and lava zone routinely stall mainland underwriters who have not seen them. A lender who works this market will move quickly. One who does not can cost you a property. Get that conversation started before you tour, not after you find something.

I handle photography, video, aerials, the 3D walkthrough, and the floor plan myself, which means the property is fully documented before it goes live, and I control the timeline rather than waiting on a vendor. From there, it is Compass’s national and international network, Zillow Showcase placement, syndication across the major portals, targeted digital advertising, direct outreach to a buyer database of more than 4,000, and personal contact with the agents actively working in that price band on this coast. At this level, a listing is a campaign rather than a posting, and most of the work happens before it is public.

Because every one of these communities has an on-site sales team, and every one of them sells exactly one community. That is their job, and they do it well. It also means the only perspective you get is the one you happen to walk into first. I work the entire coast, so I can tell you how Hualalai actually compares to Kukio on membership and culture, where Mauna Lani values hold and where they do not, why Kohanaiki feels different from both, and what Puako or Hokulia gives you that no club can. I cannot count how many luxury buyers arrived certain about what they wanted and changed their minds once they saw the alternatives side by side. Beyond the comparison, I know these places from the inside. I served as Director of Marketing for Mauna Lani Resort before real estate, which taught me how these resorts, associations, and rental programs actually operate. You hire me because I work for you, not for a single community.

Talk Story

Every Big Island move starts with a conversation. Tell me what you are looking for, and we will take it from there.

Compass Real Estate in Kona, Hawaii - Penn Henderson, Big Island Real Estate
Penn Henderson of Compass

75-1029 Henry St., Suite 301
Kailua-Kona, HI 96740

Phone: (808) 345-6214
Email: penn@pennhenderson.com