Big Island Buyer’s Guide

Prefer to read rather than flip? The complete guide follows below: the buying process, financing, lava zones, escrow, holding title, property taxes, and a profile of every West Hawaii community I work in.

What This Guide Covers

This is the full text of my Big Island Buyer’s Guide, the same guide in the flipbook above. It covers how a Big Island purchase actually works: representation, financing, lava zones, writing an offer, escrow, holding title, and property taxes, plus a profile of every West Hawaii community I work in.

I wrote it for the buyer I work with most often. Someone on the mainland, considering a second home, a vacation rental, a retirement property, or a move they have been planning for years, making the decision from a thousand miles away.

A Note From Penn

I am Penn Henderson, a full-time REALTOR® on the Big Island and a Kona resident since 2001. Over the past 25 years I have built my life, my family, and my reputation here, and I bring that local knowledge to every buyer I represent.

If you are thinking about buying on the Big Island, you already know this is more than a transaction. Whether it is a second home, a vacation rental investment, a future retirement landing pad, or a full move to the island, the decision carries weight. You deserve an agent who treats it that way.

Demand here is real, but the market is more nuanced than ever, and most of my buyers are making the call from a thousand miles away. I watch people overpay, miss what the disclosures were telling them, or lose a home they should have won, simply because the agent did not do the work. That is not how I operate.

I bring a finance degree, more than 20 years of executive sales and marketing experience, and a deep love for this island to every search. I do the homework before we ever walk into a property. I tell you what I actually think, including when I think you should pass. And I stay engaged from our first conversation through the day escrow closes.

Here is my sincere guarantee. Allow me to lead your Big Island home search, and if I am not the most consistent, caring, competent, and effective REALTOR® you have ever worked with, you are free to part ways with me at any time. No questions, no hard feelings.

Sound fair? Mahalo for considering me. You can read more about my background or get in touch directly.

Why Compass, and What It Actually Gives You

When you buy with me you get two things at once: the focused attention of a solo agent who runs every detail of your purchase personally, and a national platform working behind it. Compass gives me a transparent client dashboard, a national network I can reach directly, and a luxury division that matters in the private communities.

For years I have built my practice around a simple standard. People first. Relationships over transactions. Real service over sales pressure. Moving to Compass was a decision to give my clients more, not to change how I work.

A Purchase You Can Follow From Anywhere

Compass One gives you one secure place to watch your transaction in real time: your timeline and countdown to closing, every document, direct messaging with me, and your full team from lender to escrow. Most of my buyers manage the entire process from the mainland, often across three or four time zones. This is built for exactly that.

More Ways to Hear About a Property

Inventory in the right community can be thin, and the best opportunities often surface in conversation before they surface in a search alert. I work my own relationships across this island, and being part of a national brokerage adds another channel where agents talk about what is coming. No search tool substitutes for an agent who hears things first.

A National Network Working on Your Side

Compass is one firm, not a franchise system, which means I can reach agents in your current market directly. If selling a mainland home is part of funding this purchase, I coordinate that side personally rather than handing you off. The same network surfaces Big Island opportunities agent to agent, well before they reach a search alert.

Access at the Luxury Level

Buying into Hualalai, Kukio, Kohanaiki, Hokuliʻa, Mauna Lani, or Mauna Kea is as much about relationships as listings. The Compass Luxury division connects me to the agents and the international channels where these properties move, and my CLHMS Guild Elite credential means I have represented buyers at this level before, discreetly.

How I Approach Buyer Representation

The Big Island has roughly 1,600 licensed agents, and the average one closes three to four transactions a year. Most work part-time. My buyers are making one of the largest purchases of their lives from a thousand miles away, often sight unseen. That gap between average representation and what the work requires is the gap I built my practice to close.

That is not a knock on the profession. It is simply the math. I came to real estate with a finance degree from CU Boulder and more than 20 years of executive sales and marketing experience, and I do this full-time.

Buying a home on the Big Island is not complicated. Buying the right one is. Here is what I commit to.

Honest Assessment, Not Sales Pressure

My job is not to sell you a house. It is to help you find the right one and walk away from the wrong ones. I will tell you what is working in a property and what is not, including when I think you should pass. That has cost me transactions. It has also earned me the clients who come back and the ones who send their friends. Whoever ends up paying my compensation, you are the client, and my advice is not for sale.

Real Due Diligence Before You Write

Big Island properties carry nuances most mainland buyers have not encountered: short-term rental zoning, lava zones, water catchment, leasehold versus fee simple, HOA structures, condo warrantability, agricultural designations, access easements. I work through all of it before we write an offer, not after. My finance background is not decorative. I would rather lose a property on the facts than win one and have you find them in escrow.

A Remote Process That Actually Works

Most of my buyers never set foot in a property before going under contract, so the process has to match that reality. Detailed narrated video walkthroughs of every property we take seriously. Live FaceTime showings you direct in real time. Custom search alerts tuned to your criteria rather than a generic feed. A communication rhythm built around your time zone, not mine. None of this is an add-on. It is how the work actually gets done from three thousand miles away.

Negotiation That Protects Your Position

I research every seller’s motivation, every comparable sale, and every contingency before I write your offer. Price is rarely the only lever. The right combination of earnest money, timelines, and terms wins properties at fair prices, often over higher bids. Once we are in contract, the second negotiation begins, and inspection findings and credits get the same rigor as the offer itself. Information advantage almost always wins.

Is Now the Right Time to Buy

The honest answer depends on what you are trying to accomplish. Most of my clients are not first-time buyers, so the question is rarely whether to buy. It is when, where, and what kind of property actually serves the goal. Anyone who tells you there is a universal answer to the timing question should make you nervous.

The Hawaii market behaves differently than mainland markets, and the right strategy shifts considerably depending on what you are trying to do. Here is the framework I use.

Home Prices

The median West Hawaii home runs roughly $1.19M, up more than 120 percent since 2015. That number matters less than where your specific community sits on the curve. I track sales weekly, and pricing behaves very differently in a Waikoloa Beach Resort condo, agricultural land in South Kona, and a single-family home in Waimea.

Interest Rates and Financing

About half of Big Island sales involve financing, and Hawaii lending has its own rules. Condo warrantability, project approval, owner-occupancy ratios, and land loan terms all affect which products you qualify for and at what rate. Rate movement also shifts how much competition you face.

Tax Position

A 1031 exchange can defer capital gains when you are reinvesting proceeds from a mainland property. FIRPTA creates a withholding obligation when the seller is a foreign person, and it falls on the buyer. Hawaii County tax classification also changes with how you use the property. Your tax picture often shapes the timeline more than the market does.

Your Purpose for the Property

A pure investment property gets evaluated differently than a future retirement home. A vacation home you use six weeks a year is a different calculation than a primary residence. Be clear with yourself about which it is, because it changes everything from neighborhood to property type to financing structure.

Short Term Rental Income Potential

If short-term vacation rental income is part of the plan, zoning matters enormously here. Hawaii County has tightened its rules considerably, and not every property that looks like a rental is permitted to operate as one. I show you which areas remain eligible and how to read actual rental performance rather than listing photos.

Long-Term Plans

Where will you be in five years, or ten? Will this become a primary residence, pass to children, or get exchanged into something else? The answer changes how we structure the purchase, how you hold title, and which properties belong on the shortlist at all.

2025 Year-End Market Recap

Here is where West Hawaii stood at the close of 2025. Island-wide numbers are a starting point, not an answer. When we sit down together, I bring this same detail filtered to the communities you are considering, the property type you want, and the price band you are actually shopping in.

• West Hawaii median sales price, houses: $1,200,000
• West Hawaii median sales price, condos: $705,000
• West Hawaii median price increase since 2015: more than 122 percent

West Hawaii here means Honaunau to Kohala Ranch, including Waimea and Waikoloa Village. Figures are 2025 year-end, source Hawaii Information Service, compiled by Penn Henderson, R(S). Writing a confident offer starts with understanding the market you are competing in.

West Hawaii, Where I Live and Work

West Hawaii runs from South Kona up through North Kohala, taking in historic coffee towns, ultra-luxury resort communities, ranch country, and oceanfront estates. The climate is warm and dry, the water is calm, and the real estate options are as diverse as the landscape. It is where most of my work happens and where most of my clients end up.

The Big Island is the largest island in Hawaii, nearly twice as big as all the other Hawaiian islands combined. Energized by its massive volcanoes and remarkable range of climates, it is unlike anywhere else on earth. Where else can you travel from a sun-drenched sandy beach to a misty cloud forest in a matter of minutes?

What follows are the communities I cover most often, with 2025 pricing, a sense of what makes each place distinct, and notes on the kind of buyer who tends to land where. Use it as a starting point. Each one links to its full community page, where the current listings live.

All median sales prices below are 2025 figures from Hawaii Information Service, compiled by Penn Henderson, R(S).

The North Kona District

North Kona spans nearly 36 miles along the leeward coast, from Hokuliʻa to Waikoloa Beach Resort and up into the slopes of Hualalai. With nearly 45,000 residents it is the driving force behind the island’s expanding economy. Median sales price in 2025 was $1,297,000 for houses and $635,000 for condos.

Rich in Hawaiian history, Kona was once a favorite gathering spot for the Aliʻi, and King Kamehameha spent his final years in Kailua-Kona. In the 1800s the market took shape alongside agriculture, farming the slopes of Hualalai and using Kailua as a shipping port for sugar, coffee, and cattle. Most of the population lived in the crop-friendly elevations along Old Mamalahoa Highway, the coffee belt between 700 and 3,200 feet. That held until the early 1970s, when tourism drove development toward the lower elevations near the beaches. That is generally where you find the bulk of Kona real estate for sale today.

Kailua-Kona

Kailua-Kona is a vibrant oceanside town of roughly 16,000 residents serving as West Hawaii’s main business center, 15 minutes south of Ellison Onizuka Kona International Airport. Nearly every property type exists here, stretching down Aliʻi Drive toward Keauhou and up the hill to Holualoa: oceanfront homes and condos, residential subdivisions, private gated communities, luxury estates, and vacant land.

Once a fishing village and retreat for Hawaiian royalty, the heart of town is Historic Kailua Village, the start of the scenic byway known as The Royal Footsteps Along the Kona Coast. That seven-mile stretch of Aliʻi Drive tells the story of 700 years of Hawaii’s ruling class. Historical sites include Mokuaikaua Church, the oldest Christian church in the state and built entirely of lava and coral, Hulihee Palace, a summer retreat for Hawaiian royalty built in 1838, and Ahuena Heiau, a temple built by King Kamehameha I. Beyond the history you will find open-air shops, oceanfront restaurants, cultural festivals, and famous sporting events including the IRONMAN™ World Championship and the Jingle Bell Beach Run.

2025 median sales price: houses $1,250,000, condos $635,000.

Holualoa

Holualoa sits 10 minutes up the hill from Historic Kailua Village, on the cool lush slopes of dormant Hualalai, squarely inside the ideal growing zone for the Kona coffee bean. Cool mountain air, volcanic soil, and afternoon mist combine to make one of West Hawaii’s most distinctive places to live. The village has vintage charm, small businesses, churches, and well-known accommodations including the pink Kona Hotel and the Holualoa Inn.

The Kona Coffee Belt is a 30-mile strip running almost parallel to the coastline between 700 and 3,200 feet, starting north at Makalei and running south through Kaloko, Holualoa, Kainaliu, Kealakekua, Captain Cook, and Honaunau. The zone gets 60 or more inches of rain a year, well-drained volcanic soil, mild temperature swings, sunny mornings, cloudy afternoons, and wind protection from the mountains. If you want to grow coffee, this is one of the best spots you will find.

Holualoa also blends old Hawaii with fine arts, with private galleries showing local artists across various mediums. Homes range from old Kona coffee cottages to elaborate luxury estates with large acreage, many with privacy, tropical gardens, and panoramic ocean views.

2025 median sales price: residential homes $1,750,000.

Keauhou

Five miles south of Historic Kailua Village, Keauhou is both a popular visitor destination and a sought-after residential community, with sunny weather, long sunsets, and miles of oceanfront coastline suited to an active life. Snorkeling, kayaking, outrigger canoe paddling, fishing, surfing, scuba diving, and swimming with manta rays are all here, plus the oceanfront 18-hole Keauhou Country Club.

Residents have services and amenities at the Outrigger Kona Resort and Spa at Keauhou Bay and the Keauhou Shopping Center, with dining, weekly hula and cultural events, a grocery store, post office, gas station, cinemas, galleries, and boutique shops. For everything else, Kailua-Kona is an easy 10-minute drive down Aliʻi Drive.

Keauhou takes its name from ke au hou, the new era. It is one of Hawaii’s most historically rich locations, including Keauhou Bay where Kamehameha III was born, Kahaluu Bay, numerous sacred heiau, the Kuamoʻo Battlefield and Lekeleke Burial Grounds, and the Keauhou Holua Slide, a National Historic Landmark.

Keauhou has a special place in my heart. I live nearby and worked here for over 15 years with Fair Wind Cruises at Keauhou Bay. Having served on Keauhou’s marketing committee, I am proud to have played a small role in shaping its future.

2025 median sales price: houses $2,300,000, condos $750,000.

Kohanaiki

Two miles south of the Kona airport, Kohanaiki is a 450-acre private residential development on the sunny Kona Coast, and one of the best luxury living opportunities in Hawaii. Members enjoy a Rees Jones-designed golf course, a 67,000 square foot clubhouse and spa, a beach club and members’ beach, an adventure team, and restaurants ranging from casual to five-star.

Real estate here includes home sites, custom single-family luxury homes, and luxury townhomes, ranging from $3 million to over $20 million. Situated along the shores of Pine Trees Beach, one of Kona’s best surf spots, the setting is unrivaled in natural character. The care and conservation put into the planning and stewardship of the area is a genuine consideration when weighing luxury options on this island.

Kohanaiki is an invitation-only private club community. Each equity member who acquires club membership pays an initial membership contribution and annual dues, plus annual association dues to the Kohanaiki Community Association and condominium association dues where applicable.

2025 median sales price: residential homes and villas $5,200,000.

Kukio

Kukio is the gold standard for luxury homes in Hawaii: laid-back opulence, exclusivity, and privacy with unparalleled security. A retreat for modern-day royalty, celebrities, and business leaders from around the world, it is one of the only private equity beach clubs on the Big Island, with all facilities reserved for members and their guests.

Only Kukio owners can become members of the club, centered on a full-service beach clubhouse with an archaeological preserve, Hawaiian fishponds, open-air spa, fitness facilities, dining pavilion, green space, and swimming pool. On the beach at Kukio Bay, the Outdoor Pursuits program supports stand-up paddleboarding, surfing, outrigger canoe paddling, sailing, ocean fitness training, and kayaking. Adjacent to the beach club is a 10-hole Tom Fazio-designed short course, with an acclaimed 18-hole championship course a few minutes away.

2025 median sales price: homes and villas $14,000,000, based on seven sales.

Hualalai Resort

Hualalai Resort sits on 625 prime oceanfront acres, 10 minutes from the Kona airport, anchored by the award-winning Four Seasons Resort Hualalai. For the discerning buyer it holds some of the most exclusive luxury homes and condos in Hawaii.

Owners have access to the Hualalai Golf Club, the Four Seasons Resort, and the Hualalai Sports Club and Spa. Property owners who become club members gain access to the private Tom Weiskopf 18-hole championship course, the 18-hole Jack Nicklaus course, the Keolu Golf Clubhouse, and the Canoe Club perched above Kukio Bay. The resort brings dining, numerous pools, a tennis facility, and boutique retail, plus scuba diving, snorkeling, hiking, cycling, fishing, kayaking, paddleboarding, and surfing.

Options run from single-family estate homes to luxury condos, townhomes, and villas, with a few vacant house lots remaining. Within the resort there are approximately 30 different home and condo neighborhoods.

2025 median sales price: homes and villas $10,242,500.

Kalaoa

Kalaoa sits just north of Kailua-Kona and directly up the hill from the airport, extending from the ocean to the lower slopes of Hualalai in the upper Makalei and Kaloko areas. Other than Kohanaiki, you will not find residential property within a mile of the ocean here, but the location gives convenient access to both Kailua-Kona and the Kohala Coast.

Home to roughly 12,000 residents, Kalaoa runs from modest residential homes to coffee farm estates and custom homes. Nearly all properties benefit from sloping topography, so ocean views are common. Kailua-Kona’s business district is 10 minutes away, though many essentials are here, including Costco and Home Depot. Honokohau Boat Harbor is nearby for deep-sea fishing, diving, snorkeling, whale watching, and small boat rentals.

Kalaoa was my first home on the Big Island, where I lived for five years while working at Mauna Lani Resort up on the Kohala Coast. Most of Kona’s best hiking trails are in upper Kalaoa, along with several of my favorite beaches: Kaloko Honokohau, Pine Trees, Kekaha, Makalawena, and Kua Bay.

2025 median sales price: residential homes $1,100,000 for Palisades and Kalaoa.

Honalo

Honalo covers 30 square miles, 15 to 20 minutes from Kailua-Kona’s business district, home to roughly 2,300 residents. It sits within the Kona Coffee Belt along the southern border of North Kona, mauka from Keauhou, between Holualoa to the north and Kealakekua to the south. At about 1,400 feet the climate brings sunny mornings, cloudy afternoons, and cooler temperatures in the 70s.

Property here is generally smaller vintage Hawaiian-style homes, large acreage parcels, horse properties, tropical fruit farms, and coffee farms. The topography is sloped, so ocean view opportunities are good, though foliage can be dense in parts of Honalo with large trees blocking potential views.

2025 median sales price: residential homes $1,194,250.

Puuanahulu and Puu Lani Ranch

If you are looking at Puuanahulu, your search will most likely center on Puu Lani Ranch, a gated community at the northern edge of the North Kona district surrounded by at least 10 miles of open terrain in every direction. Homes sit on one-acre lots with mountain views and some ocean views, at an elevation of 2,000 feet where temperatures run cooler.

The community has its own equestrian center with a riding ring and stables for horse boarding. Despite few services in the immediate area, it is within 30 minutes of most West Hawaii business centers: Kailua-Kona at 10 miles, Waikoloa Village at 18, Waimea at 22, and the Kohala Coast at 23.

2025 median sales price: residential homes $1,437,500.

The South Kona District

South Kona takes in Kainaliu, Kealakekua, Captain Cook, Honaunau and Napoopoo, resting on both Hualalai and Mauna Loa and extending from sea level into the upper ohia cloud forests. Locals call it Kona Country. Thirty minutes from the airport, it is a haven away from the bustle. Median sales price in 2025 was $750,000 for residential homes.

The area holds a seemingly endless number of farms producing Kona coffee, tropical fruit, macadamia nuts, and flowers. Most homes sit in the coffee belt between 700 and 3,200 feet, where temperatures run cooler, generally in the 70s, with more rain than the oceanfront communities below.

South Kona is loaded with historical significance dating to the 12th century. It is home to Puʻuhonua o Honaunau, the Place of Refuge, and Kealakekua Bay, where Captain James Cook first landed in Hawaii and where he later lost his life in 1779. It is also the birthplace of the Kona coffee industry, which began in the 1800s.

The range of property is wide: typical Kona residential homes, old coffee farm homes, and multi-million-dollar manicured estates. If you want a home with your own fruit and coffee trees, South Kona is excellent. You will not find many condos here, and no hotel resort communities. Though it is fairly rural, there are business services, dining, grocery stores, and outdoor adventure.

Kealakekua

Ten miles south of Kailua-Kona, Kealakekua is one of several small historic towns in South Kona, home to roughly 2,000 residents. Until a few decades ago this was Kona’s main hub, when agriculture drove the island’s economy. Visiting is a refreshing glimpse into Hawaii’s pre-statehood days.

Along with neighboring Kainaliu, the area has local-style restaurants, boutique shops, galleries, cafes, banks, a grocery store, and some of the best vintage Hawaii antique shops on the island. Until the early 1970s most of Kona’s population lived here, where higher elevation, cooler temperatures, and more rainfall let agriculture flourish. At 1,400 feet the climate suits coffee and fruit, and it makes for a comfortable place to live. Kealakekua remains vital today, home to West Hawaii’s only major hospital.

One of the most iconic buildings you will see along Kainaliu’s main street is the Aloha Theatre, opened in 1932 by the Tanimoto family. The 325-seat venue showed Japanese and American films for coffee farm workers until the 1970s, then reopened after renovation with a focus on live music and theatre. It is Kona’s oldest theatre and home to the Aloha Performing Arts Company. My father-in-law grew up in that theatre with his parents and siblings in the 1930s.

2025 median sales price: residential homes $948,750.

Captain Cook

Just past Kealakekua, Captain Cook is a tight-knit community with the same relaxed old-Hawaii feel that runs through South Kona. It is considered semi-rural, on the outer edge of Kona’s business hub, serving roughly 3,500 residents with a few restaurants, a good grocery store, an ACE Hardware, and scattered shops. For major shopping, Kailua-Kona is about 30 minutes away.

At a comfortable 1,250 feet, conditions are similar to Kealakekua: cooler temperatures and more rain than the oceanfront communities a few minutes down the road. There are numerous coffee farms here, both small and large. Driving the rural roads you will see an incredible variety of fruit trees on nearly every property, particularly mango and avocado, which tend to be an eye-opener for mainland visitors.

One of the biggest draws is the Pure Kona Green Market, held each Sunday from 9:00 AM to 2:00 PM, with fruit, homemade food, arts and crafts, and more. Arguably the best farmers market in West Hawaii.

2025 median sales price: residential homes $825,000.

Honaunau and Napoopoo

Honaunau and Napoopoo cover more than 40 square miles from sea level up into the high elevations above Mamalahoa Highway, home to roughly 2,500 residents. This is the most historically significant area in South Kona, holding the marine life sanctuary of Kealakekua Bay and the Captain Cook Monument to the north, and Puʻuhonua o Honaunau, a national historical park, to the south.

In the 12th century the Puʻuhonua was built as a religious refuge. Hawaiians lived under the kapu system, and breaking a kapu usually meant immediate death. If a lawbreaker reached a place of refuge, their life was spared, and kahuna performed absolution ceremonies. The walls extended 10 feet, adjacent to the Royal Grounds, the sacred home of the aliʻi. Carved images of gods known as kiʻi guarded the Hale o Keawe heiau, the temple that once held the bones of deceased aliʻi.

Three miles north, Napoopoo Village sits on the south end of Kealakekua Bay, a tiny oceanfront community with lush landscapes and gorgeous shoreline. Residents are close here, many part of long family lineages tied to the area. The bay stretches a mile end to end and is considered one of the best snorkeling locations in Hawaii. Napoopoo Road winds 4.5 miles up steep slopes to 1,300 feet near Captain Cook and Kealakekua, lined with homes carrying unparalleled ocean views.

2025 median sales price: $934,500.

Hokuliʻa

Hokuliʻa is an oceanfront luxury resort community on the border of North and South Kona, distinctly different from the Kohala Coast: privacy taken to another level, with no hotels or commercial areas inside the community. It covers 1,300 acres including three miles of Kona oceanfront and rises to over 700 feet. Because of the sloping topography, nearly all properties have spectacular ocean views.

The Club at Hokuliʻa offers a fitness facility, lap and resort-style pools, tennis courts, spa, walking trails, a shoreline park, and an open-air Polynesian-style pavilion with fine dining and sunset views over the Pacific. One of the biggest perks of ownership is the 18-hole Jack Nicklaus signature golf course, consistently ranked among the best in Hawaii, with a golf lounge and locker rooms alongside the pro shop. Community tournaments and charity events run throughout the year.

A handful of homes are available along with custom home lots ready to build. Lot sizes run approximately one acre, with homes varying from 3,500 to 6,000 square feet.

The Kohala Coast

The Kohala Coast is the sunniest part of the Big Island, with warm temperatures and just nine inches of rain a year. Thirty minutes north of the Kona airport, it holds six world-class hotels and golf courses across three resort communities. Median sales price in 2025 was $4,900,000 for houses and $1,625,000 for condos.

Real estate here is highly sought after, with diverse price points and property types: condos, townhomes, residential homes, luxury homes, luxury condos, vacant land, and ultra-luxury estates above $10 million. Just beyond the resorts, further up the coast, there are a handful of communities not to be overlooked, some oceanfront, several with large acreage suited to horse properties, and almost everywhere with ocean views.

You will find tropical oceanfront communities carved into sprawling fields of ancient lava flows. The beauty is unmistakable, and it is one of the reasons the area earned the nickname the Gold Coast.

Waikoloa Beach Resort

Waikoloa Beach Resort is anchored by the Hilton Waikoloa Village and the Waikoloa Beach Marriott Resort and Spa, and centers on Anaehoʻomalu Bay, undeniably one of the best beaches in Hawaii. Nearby are more than 100 shops, cafes, bars, galleries, restaurants, and two championship 18-hole golf courses.

A-Bay, as it is known, is adored for soft sand and calm water. Conditions suit snorkeling, swimming, kayaking, paddleboarding, windsurfing, and kiteboarding. It also hosts the LAVAMAN triathlon each spring, one of my favorite events and a permanent fixture on the family calendar.

Property runs from oceanfront estate homes to amenity-loaded condominiums. Two marquee developments sit within the resort, Kolea and Haliʻi Kai, both with oceanfront lot opportunities and extensive golf course frontage at Haliʻi Kai. Prices start around $800,000 for condos and extend into the millions for homes. Oceanfront property is a rare commodity here, but there are many condos available and a few homes with outstanding ocean views and golf frontage.

2025 median sales price: $1,242,500.

Mauna Lani Resort

When it comes to resort living on the Kohala Coast, nothing quite compares to Mauna Lani, and I know it well, having served as Director of Marketing at Mauna Lani Resort for several years. That is a level of familiarity with this property few agents can claim.

Traditionally known as Kalahuipuaʻa, Mauna Lani is the ancestral home of Hawaiian royalty and the only place in Hawaii where you can see five volcanoes: Mauna Kea, Mauna Loa, Kohala, Haleakala, and Hualalai. That ancient energy lives in the historic fishponds, prehistoric petroglyphs, and the resort itself. The whole resort was built to take advantage of the coast’s raw beauty, with miles of walking paths mapped to capture it.

Owners have access to two world-class golf courses, a private beach club, a tennis club with 10 courts, the Mauna Lani Spa and Fitness Center with a 25-meter lap pool, and the Shops at Mauna Lani with a grocery market, restaurants, cafes, and boutique shopping. More dining sits at the resort’s two luxury hotels, the Mauna Lani Auberge and the Fairmont Orchid Hawaii. The toughest decision here is not whether to go to the beach, it is which beach: black sand, white sand, and peppered sand, some secluded, others with full-service cabanas.

Condos generally start in the $600,000 range, though most are closer to $1,000,000 and beyond. Homes start around $3 million, with the bulk priced between $5 million and $20 million. Developments include 49 Black Sand Beach, Pauoa Beach, Mauna Lani Point, Mauna Lani Point Estates, Villages at Mauna Lani, Fairways at Mauna Lani, Kulalani, Ka Milo, and Palm Villas.

2025 median sales price: houses $6,075,000, condos $1,672,000.

Puako

Puako sits off the beaten path between Mauna Lani and Mauna Kea, a small secluded oceanfront community that drew little attention until recent years. Today it is in high demand and considered one of the most unique luxury beachfront communities on the Big Island.

There are essentially two sides to Puako, separated by the community’s only road, which runs three miles along the coast. One side is beachfront and the other is not, so price ranges and property types vary significantly. Puako is limited to just over 150 properties and is free from the covenants and restrictions you would typically be subject to in the surrounding resort areas. It is hard to believe an area like this still exists in Hawaii: a low-key feel and vintage Hawaii charm, minutes from world-class resort amenities.

While petroglyphs are found throughout Hawaii, the largest concentrations are just south of Puako. The archaeological preserve there holds more than 3,000 petroglyphs dating back to 1200 AD, open to the public.

2025 median sales price: $1,800,000.

Mauna Kea Resort

Mauna Kea is the resort that started it all. Developed by Laurance Rockefeller and opened in 1965, it remains an iconic gem on the Kohala Coast, built around the Mauna Kea Beach Hotel and the Westin Hapuna Beach Resort, with two of the best beaches in the world: Mauna Kea Beach and Hapuna Beach.

The resort has two championship 18-hole golf courses, an oceanfront 11-court tennis club, two fitness centers, numerous restaurants, the Mauna Kea Spa, and a collection of over 1,600 museum-quality pieces of Asian and Oceanic art. Properties benefit from sloping topography rising from the ocean, giving most homeowners ocean views, sunset views, and distant views of Maui.

Developments include The Bluffs at Mauna Kea, The Villas at Mauna Kea, Kumulani at The Uplands, The High Bluffs, Apaʻapaʻa at the Uplands, Fairways at Mauna Kea South, Fairways at Mauna Kea North, Moani Heights at The Uplands, Waiʻulaʻula at Mauna Kea, and Kaunaʻoa.

2025 median sales price: houses $6,200,000, condos and villas $4,917,500.

South Kohala Upcountry

Above the resort coastline sit two very different communities: Waikoloa Village, six miles up the hill, where more attainable single-family homes and condos are easier to find, and Waimea, at 2,600 feet, cooler and greener, with a paniolo small-town character unlike anywhere else in Hawaii.

Waikoloa Village

Waikoloa Village is a fast-growing yet relaxed community six miles up the hill from the resort-lined Kohala Coast. Your chances of finding more attainable single-family homes and condos are generally better here than elsewhere in West Hawaii, which makes it a logical choice for many buyers.

The location is convenient: Kailua-Kona in 45 to 60 minutes, Waimea in 20, the Kohala Coast in 10, and Hilo in just over an hour. Serving roughly 7,000 residents, the village has a shopping area, bank, gas station, grocery store, several restaurants and cafes, and a post office, with world-class golf and dining nearby at Waikoloa Beach Resort, Mauna Lani, and Mauna Kea.

Real estate here is subject to annual HOA dues, which cover tennis courts, two swimming pools, and an 18-hole community golf course. Worth knowing: Waikoloa Village can be windy, sitting between Mauna Kea and Kohala directly in the path of northeast trade winds funneling through the saddle.

I have several friends who bought here and love it. Proximity to the beaches and the resorts was a big factor in their decision.

2025 median sales price: houses $957,000, condos $453,500.

Waimea

Waimea, also known as Kamuela, is home to roughly 9,000 residents, making it the largest town in the northern part of West Hawaii. At a cooler elevation of 2,600 feet the climate is quite different from most other communities in Hawaii, and sitting in the saddle between East and West Hawaii, the weather can change quickly.

Despite the remote feeling and upcountry climate, Waimea is 20 minutes from sun-drenched beaches in one direction and valleys full of waterfalls in the other. It is well known for easy access to some of the best hiking, cycling, and running on the Big Island. You will also find a sophisticated yet laid-back paniolo small-town character, with farmers markets, good food, an eclectic local culture, and modern amenities.

Properties range from smaller residential homes to larger estates with acreage. To understand the area, plan on spending time exploring its different pockets, where climates vary significantly. Waimea on a sunny day is considerably different from Waimea on a windy, rainy one, which is part of the appeal for many and may not be for everyone.

Waimea is often our basecamp for family adventures. When the weather cooperates there are few places on earth that compare. We will usually do some biking in the morning and then hit the farmers market afterward for lunch.

2025 median sales price: $945,000.

The Buyer’s Representation Agreement

Before we start touring homes we formalize the working relationship through a Buyer’s Representation Agreement. As of August 2024 this is a nationwide requirement, not a rule I invented. Every buyer working with a REALTOR® in the United States now signs one. Think of it as the equivalent of a listing agreement on the seller’s side.

It defines what I am responsible for, what you are responsible for, how I am compensated, and how either of us can end the relationship if it is not working. Most of my buyers are signing one for the first time. The form is straightforward, and I walk through it with you before anything gets signed.

Why It Matters for You

• Establishes me as your exclusive representative, with a fiduciary duty to protect your interests
• Secures confidentiality around your finances, motivations, and negotiating position
• Clarifies compensation up front, with no surprises at closing
• Eliminates conflicts of interest with competing agents or listing agents
• Sets expectations for how we communicate and how the process will run

When It Is Needed, and What It Commits You To

As early as possible, before we start touring homes. We can set the agreement to a specific time period, a specific area, or a specific set of properties. It is not designed to trap anyone. It is designed so we both know what we are doing and I can put real time and research behind your search.

On compensation: my figure is stated in the agreement and we discuss it before you sign, not at the closing table. In many transactions the seller offers a concession that covers part or all of it. In others it does not work out that way. Either way you will know the number in advance, and it does not change based on which property you choose.

The Four Phases of a Big Island Purchase

A Big Island purchase moves through four phases: consultation and alignment, search and offer, under contract, and closing. Most run 30 to 60 days from accepted offer to recorded deed. Your role is to stay informed and make decisions. Mine is to run the process, including everything that happens between those decisions.

Buying real estate here involves a lot of moving pieces: property searches, showings, financing, inspections, escrow, negotiations, closing logistics, and dozens of small decisions in between. For buyers who are not on-island during the search, managing all of it from a thousand miles away is one of the biggest sources of stress. You do not have to manage any of it. I do.

Phase One: Consultation and Alignment

The first conversation is not about touring homes. It is about understanding what you are trying to accomplish, what kind of property fits, and how to set the search up for success.

• An in-depth consultation on your goals, preferred areas, must-have features, and timeline
• A walkthrough of the current market and what to expect at your price point
• An overview of the buying process, including short-term rental zoning, financing nuances, HARPTA and FIRPTA, and anything specific to your situation
• Connection to trusted local lenders if financing is part of the plan
• A custom search built around your criteria, with new-listing and price-change alerts
• Your Compass One dashboard set up, so the search, documents, and team live in one place
• Buyer’s Representation Agreement signed and on file

Your role: be honest about what you actually want, what you are flexible on, and what your real budget looks like. The clearer we are at the start, the faster we find the right property.

Phase Two: Search, Tour, and Offer

This is the active phase. Depending on your timeline and whether you are on-island, it can move fast or unfold over months. I prescreen every property before it reaches you, and I will tell you when I think one is not right for you.

• Daily monitoring of new MLS listings, plus off-market opportunities I hear about through agent channels
• Property prescreening, including detailed narrated video walkthroughs for off-island buyers
• Private showings, broker tours, and open houses, attended personally
• Research on every property of interest: zoning, HOA, rental history, sales comps, area trends
• Investigation of seller motivations and circumstances to inform offer strategy
• Drafting and submitting your offer with terms designed to win without overpaying
• Negotiating counteroffers, credits, and contract terms on your behalf

Your role: stay engaged with the search, give honest feedback on the homes I send, and trust the process when I recommend passing on a property. The market does not reward emotion.

Phase Three: Under Contract

Once your offer is accepted, escrow opens and the clock starts on every contingency in the contract. This is where most of the technical work happens, and where having an experienced agent matters most.

• Escrow opened, earnest money wired, title report ordered and reviewed
• Lender coordination for financing approval and appraisal scheduling
• Home inspection scheduled and personally attended, with specialty inspections ordered as needed
• Seller’s disclosures, HOA documents, and property-specific reports reviewed in detail
• Inspection negotiations for repairs, credits, or price adjustments
• Contingency tracking and removal in proper sequence
• Final walkthrough scheduled and attended

Your role: review reports and disclosures, make decisions on inspection negotiations, and stay in close contact with your lender. I will flag every deadline as it approaches.

Phase Four: Closing and Keys

The final stretch. Loan funded, documents signed, deed recorded. For mainland buyers, signing is handled remotely with a mobile notary. Closing typically happens 30 to 60 days after going under contract, depending on financing.

• Final coordination with escrow, the lender, and the title company
• Closing document review before you sign
• Verification of wire instructions directly with escrow before any funds move
• Confirmation of recording with the State of Hawaii Bureau of Conveyances in Honolulu
• Utility transfer and address coordination, if needed
• Guidance on Hawaii County tax classification and any exemption filings that apply
• Keys, garage remotes, gate codes, manuals, and other property items collected for you

Your role: sign closing documents, often by mobile notary at your location, wire your remaining funds to escrow, and set up property accounts on your end. Then move in. Your Compass One dashboard stays open after closing, so every document remains in one place when you need it at tax time or on resale.

How Buying Sight Unseen Actually Works

Most of my clients are not on the Big Island during their search. They are on the mainland or overseas, often writing offers on properties they have never stood in. That changes how the process has to work. I do not rely on listing photos alone, because listing photos are curated and video shows the truth.

I create detailed narrated video walkthroughs of every property we seriously consider. Clear views of layout, condition, and surroundings, plus the things that never show up in MLS photos: the neighbor’s roof, the road noise, the view from the kitchen, what the lanai actually feels like at four in the afternoon.

We can also connect live by FaceTime so you can direct the showing in real time and ask questions as we walk. Every video stays saved and shareable, so you can rewatch it, sit with it, and send it to whoever else is part of the decision. Most clients tell me this is the closest thing to being there in person. I have done more than 400 property tour videos for clients over the years, and if you see a listing you like while browsing, just ask and I will get one done.

Penn provided above-and-beyond service making this sight-unseen mainland transaction a breeze. He provided detailed videos showing every aspect of the condo, and even one showing an evening sunset. Pat and Pam, oceanfront condo investment buyers, Kailua-Kona.

Financing Your Big Island Home

The basics are familiar: lenders evaluate income, credit, debt, down payment, and reserves. What catches mainland buyers off guard is how differently Hawaii financing works once the lender starts evaluating the property itself. Get pre-approved first, not last. A real pre-approval typically takes one to two weeks, and we start it the same day we begin your search.

A genuine pre-approval, not just a pre-qualification, gives us a defensible price range, a stronger offer when we write, and a clean closing once we are under contract.

Beyond your personal financials, lenders also evaluate the property: title status, HOA financial health, appraisal value, insurance requirements, and property taxes. For Hawaii specifically, this is where things get nuanced, and where the wrong lender can derail an otherwise solid transaction.

Why a Local Lender Matters Here

Choosing a lender on a Hawaii purchase is not just about rate. It is about whether the loan will actually close. Hawaii condos are classified warrantable or non-warrantable based on owner-occupancy ratios, short-term rental activity, HOA financial health, and insurance coverage, and that classification dramatically affects which loan products are available and at what rate.

Condo Financing

Many West Hawaii resort condos are non-warrantable because of high vacation rental activity. Mainland lenders often do not catch this until weeks into underwriting, at which point the loan falls apart and the buyer has to start over. Local lenders know the buildings, know the workarounds, and can close on properties mainland lenders cannot.

Land Loans

Buying a lot to build on later? Land loans in Hawaii work differently than mainland construction loans, with different down payment requirements, different terms, and a narrower pool of lenders. Working with someone who understands the local lot market saves significant time and money.

The right local lender saves real money. The wrong one can derail an entire deal. I have worked with most of the active Hawaii lenders and can point you toward two or three I trust, depending on your situation. Call me before you commit to a lender, not after.

What Lava Zones Mean for Insurance and Financing

The U.S. Geological Survey maps the island into nine lava hazard zones by long-term probability of lava flow. Zone 1 carries the greatest hazard, Zone 9 the least. For buyers this matters in two practical ways: insurance and financing. Higher-hazard zones can be difficult or expensive to insure, and that directly affects what lenders will finance.

Here is what most buyers do not realize. The meaningful dividing line is between Zone 2 and Zone 3. Zones 1 and 2 sit on or alongside the active rift zones of Kilauea and Mauna Loa, where flows are most frequent. That is where insurance options narrow, premiums climb, and financing gets complicated. Most lenders will not write loans there at all without significant money down.

From Zone 3 upward the risk profile changes entirely. Standard insurance is readily available, financing follows normal underwriting, and volcanic risk does not weigh on property values. The vast majority of West Hawaii, including Kona, the Kohala Coast, Waikoloa, and Waimea, sits well within these lower-risk zones. Waikoloa Beach Resort is Zone 3. Waimea is Zone 8. The geology that makes headlines is concentrated on the active side of the island, not where most of the market trades.

Zone assignment can shift within a single neighborhood, so I confirm it parcel by parcel rather than by area. On every property we take seriously I verify the exact zone and get you a real insurance figure in writing during the contingency period, before you are committed to anything. There is more detail on my Big Island lava zones page.

How I Write an Offer

The offer is not just a number, it is a strategy. A well-structured offer wins properties at fair prices, often beating higher bids. A poorly structured one overpays, loses to inferior competition, or falls apart under contract. Every offer I write starts with the same homework: know the seller, know the property, know what wins.

Know the Seller

What is motivating the sale? How long has the property been on the market? Are there price reductions in the history? Is the listing agent signaling flexibility on timing or contingencies? Public records, MLS history, conversations with the listing agent, and a careful read of the disclosure package usually answer most of these questions before we ever name a price.

Know the Property

Every offer is informed by recent comparable sales, current competing inventory, property condition, and any red flags surfaced during due diligence. I bring you the data, the analysis, and a recommended range with the reasoning behind it. You make the final call on price and terms.

Know What Wins

Price matters, but it is rarely the only lever. The right combination of earnest money, contingency timelines, closing date, inspection terms, and how the offer is presented can win a property at a lower price than a competing bid that simply threw money at it. I write every offer with intent.

Inspection and Repair Negotiation

Once we are under contract the second negotiation begins. The inspection always finds something, and the question becomes what is worth asking the seller to address, what is worth accepting, and what is worth walking away from. Handled well, this protects your investment without blowing up the deal. Handled poorly, it costs you the property or the price advantage you fought for in the original offer.

The Hawaii Escrow Process

An escrow company is a confidential, impartial third party that holds funds and documents until every condition of the purchase contract is satisfied. It represents neither you nor the seller. In Hawaii, escrow opens the moment both parties sign the purchase contract, and your earnest money is wired within a few days of execution.

For mainland buyers especially, this is where the process can feel opaque, because Hawaii’s escrow system works differently than what you may be used to. The good news is that escrow is designed to protect both parties, and you have an experienced agent and a neutral third party coordinating the whole thing. You do not need to learn the mechanics. You just need to know what is happening, when, and what is expected of you.

Typical Timeline: 30 to 60 Days

Most Big Island escrows run 30 to 60 days depending on whether you are paying cash or financing. Cash transactions can close faster, sometimes in two to three weeks. Financed transactions take longer because of lender underwriting, appraisal, and final loan approval. I work closely with escrow throughout to keep every milestone on track and flag potential issues before they become delays.

Contingencies and Your Earnest Money

Your contract includes contingencies, the conditions that must be satisfied or waived before you are obligated to close. The most common are home inspection, financing approval, title review, appraisal, seller disclosure review, and for condos, HOA document review.

If you cancel within your contingency periods for a covered reason, your earnest money is typically refundable. Once you remove contingencies you are fully committed, and your deposit is at risk if you walk away without cause. I track every contingency deadline and walk you through every decision point. You will never miss a window because I did not tell you it was coming.

Closing and Recordation

About a week before closing, escrow prepares your closing documents, including the deed and loan documents if you are financing. You sign separately from the seller. Rarely are both parties in the same room, especially here. If you are on the mainland, signing is handled remotely with a mobile notary and the original notarized documents are returned to escrow.

All signed documents and your remaining funds, meaning your down payment plus closing costs, must reach escrow no later than two business days before recordation. On closing day the documents are recorded at the Hawaii Bureau of Conveyances in Honolulu, your loan funds if applicable, and the property officially becomes yours. The seller receives their proceeds. You receive the keys.

Escrow looks complex from the outside. For my buyers it is not. I manage the timeline. Escrow manages the funds and documents. You sign when it is time to sign. That is the entire experience.

How to Hold Title in Hawaii

Hawaii recognizes four main forms of ownership: tenants in severalty, tenants in common, joint tenants, and tenants by the entirety. How you take title affects how the property transfers if you pass away, how it is protected from individual creditors, and how it fits your estate plan. Decide before you sign your offer, not at closing.

Tenants in Severalty

For sole owners. You hold title alone, with no other person or entity having an ownership interest. Also used when title is held by a single trust. The word severalty comes from severed, not several. It refers to ownership that is separate and individual.

Tenants in Common

For two or more owners who want to define specific ownership percentages. Each party owns their share independently. When one owner passes away, their share becomes part of their estate and transfers according to their will, trust, or state probate law, not automatically to the other owners. Most commonly used by unmarried co-owners, business partners, or married couples in second marriages where each spouse has children from a prior relationship.

Joint Tenants

For two or more owners who want equal shares with right of survivorship. When one owner passes away, their share automatically transfers to the surviving owners in equal portions, bypassing probate entirely. Historically the most common way for married couples to hold title in Hawaii, though tenants by the entirety has largely replaced it for that purpose.

Tenants by the Entirety

Reserved exclusively for married couples. Offers all the benefits of joint tenants, meaning equal ownership, right of survivorship, and no probate, plus one significant additional protection: the property is shielded from individual creditor claims against either spouse. If one spouse is sued individually, that claim cannot attach to the jointly held home. Joint debts and liabilities still can. This is the most common form of ownership for married couples buying in Hawaii today.

Trusts and LLCs

Many of my buyers take title in a revocable living trust, which keeps the property inside an existing estate plan and avoids probate without changing how you use or finance it. Others, particularly on vacation rental purchases, consider an LLC for liability separation.

Both are common and both are workable, but they change things upstream. Most conventional lenders will not lend to an LLC, and taking title in an entity can affect your county tax classification. If either is on the table, we need to know before we write the offer, not at signing.

This is a legal decision, not a real estate decision. I can walk you through the options at a high level, but the right choice depends on your estate plan, marital situation, and tax goals. This is general guidance and not legal advice. Coordinate with a Hawaii-licensed attorney or estate planning professional before you sign.

How Big Island Property Taxes Work

Hawaii County property tax rates are significantly lower than California, Texas, Colorado, or most states my clients come from, and the Homeowner rate for owner-occupied primary residences is especially generous. Taxes run on a fiscal year, July 1 through June 30, paid in two installments: August 20 and February 20.

Installment one, due August 20, covers July 1 through December 31. Installment two, due February 20, covers January 1 through June 30.

How Assessed Value Is Set

Property taxes are based on assessed value, determined by the County Real Property Tax Office, which may differ from market value. For existing properties, the County appraisal team reviews comparable sales data, typically without visiting, to determine value as of January 1 each year. That January 1 value sets taxes for the following fiscal year.

For new construction not yet completed, the appraiser typically values the property on the cost of building permits filed with the County. Permit costs are usually a fraction of actual market value, which is why newly built homes often carry taxes well below market for the first year or so. A home completed in May 2026 is taxed for fiscal year 2026 on its January 1, 2026 value, before the house was finished. By January 1, 2027 the County has completion and sales data, and the assessment usually jumps considerably.

What Changes When You Buy

The taxes the seller is paying are usually not the taxes you will pay. If the seller occupied the home as a primary residence and you will not, the property moves from the Homeowner class to the Residential class, and the rate roughly doubles. This is the single most common property tax surprise for second-home buyers on this island. I check the current classification and model the post-closing figure on every property we take seriously, before you write an offer.

The Rate Table

Rates below are per $1,000 of net taxable value for fiscal year July 1, 2026 through June 30, 2027. Multiply the rate by the assessed value in thousands. Minimum annual tax is $200.

Class	Rate per $1,000
Affordable Rental Housing	$5.75
Homeowner (Resident)	$5.75
Long Term Rental	$7.75
Agricultural and Native Forests	$9.35
Commercial	$10.70
Industrial	$10.70
Residential	$11.10
Conservation	$11.55
Hotel/Resort	$11.55
Apartment	$11.70
Residential, portion valued $2M to $4M	$14.50
Residential, portion valued $4M and above	$17.00

The tiered Residential rates apply only to properties with no exemption, and only to the portion of value above each threshold.

Example Calculations

A $1,500,000 home held as a primary residence at the Homeowner rate of $5.75 generates roughly $8,625 per year, before any home exemption. The same home held as a second residence at the Residential rate of $11.10 generates roughly $16,650.

Above $2 million the Residential rate tiers, and it tiers on the margin rather than all at once. A $5,000,000 second home is taxed at $11.10 on the first $2 million, $14.50 on the next $2 million, and $17.00 on the final $1 million, for roughly $68,200 per year.

Disputing Your Assessed Value

Assessment notices are mailed by March 15. If you believe your assessed value is too high, you can file an appeal using RP Form 19-91 on or before April 9. Appeals require a $50 non-refundable deposit and are limited to specific grounds, most commonly that the assessed value exceeds market value by more than 20 percent. Be prepared to provide recent comparable sales to support your case. Rates and forms are published by Hawaii County Real Property Tax.

Five Reasons Buyers Choose Me

I have had hundreds of conversations with buyers about why they chose to work with me. The reasons are consistent: deep Big Island expertise, honesty that holds up, a process built for off-island buyers, real research and due diligence, and a work ethic that shows up. These are the five that come up most often.

Deep Big Island Expertise

I have been a full-time Kona resident since 2001. I have lived through the market cycles, watched the communities evolve, raised my family here, and built deep relationships across the island. When I moved into real estate I brought all of that with me. The nuances that affect value, livability, and resale potential in a Waikoloa condo versus a Kohala Coast estate are not theoretical to me.

Honesty That Holds Up

Real estate is full of agents who will tell you what you want to hear to keep the deal moving. I came into this profession deliberately, with a strong reputation already built, and I have no interest in trading it for a single transaction. I will tell you when a property is right for you, and I will tell you when it is not. My clients consistently say that willingness to recommend they pass on something is what made them comfortable trusting me on what to buy.

A Process Built for Off-Island Buyers

Most of my clients are buying from the mainland or overseas. Detailed narrated video walkthroughs, FaceTime showings, a custom search tuned to your criteria, and a communication rhythm built around your time zone are not extras. They are how the work gets done. I write more sight-unseen offers than most agents on this island, and they hold up in escrow because the due diligence behind them is real.

Research and Due Diligence

A degree in finance and more than 20 years of executive sales and marketing experience changed how I approach property analysis. I read disclosures carefully, run comps with documented adjustments, investigate seller motivations, and dig into the zoning, HOA, and rental nuances most agents skim past. The result is offers built on real information, written with intent, and stress-tested before they leave my hands.

Work Ethic That Shows Up

Calls returned within the hour. Texts answered the same day. Properties personally previewed. Showings personally attended. Inspections personally walked. Updates throughout the search. None of this is exceptional. It is just doing the job at the standard the work deserves, and it is the single most common reason buyers leave their first agent and come to me.

When you work with me you are not hiring a brand or a brokerage alone. You are hiring me. Compass gives me a powerful platform, but the agent doing the work is the agent producing the result, and I take that responsibility seriously on every search.

Buying at the Luxury Level

West Hawaii’s luxury tier begins around $3.2M. Buying at this level is different: the properties carry weight, the communities carry rules, and the relationships between owners, brokers, and clubs matter as much as the transaction. It requires credentials to be taken seriously, local relationships to open doors, and discretion to operate without drawing attention.

My clients at this level include high-net-worth individuals, executives, real estate collectors, and families investing in generational property. They expect service that matches the value of the asset, and access to properties that match their goals, whether those properties are publicly listed or not.

Two of my designations speak directly to this work. Certified Luxury Home Marketing Specialist at its Guild Elite tier, for demonstrated performance in the luxury market. Resort and Second-Home Property Specialist, awarded by the National Association of REALTORS®, for proven experience in exactly the kind of purchase you are making.

Why the Best Properties Are Often Invisible

The Big Island’s highest-value inventory does not behave like the rest of the market. Owners at this level often prefer not to advertise. Some test the market quietly before committing to a public launch. Others will sell to the right buyer and never list at all. A search built only on portal alerts misses all of it.

When the right property does not exist on the open market, we go find it. I approach owners in the communities you are targeting, discreetly and on your behalf. Some say no. Some have been quietly considering a sale for a year and were waiting to be asked. You only need one. Buyers at this level frequently 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 in order to start a conversation.

What Nobody Tells You About Buying Inside the Gates

Hualalai, Kukio, Kohanaiki, Hokuliʻa, Mauna Lani, and Mauna Kea are not simply neighborhoods with a guardhouse. Each has its own ownership structure, and the club sitting alongside the real estate is often the more complicated purchase.

• Membership is a separate transaction. In most of these communities, buying the property and joining the club are two different decisions with two different costs and two different approval processes.
• Dues and assessments are real numbers. They belong in your carrying-cost analysis from the start, not as an afterthought.
• Rental rules vary widely. What one community permits, the one next door may not.
• Showings require a relationship. Access is not automatic, and it is not the same as booking a tour.

I have deliberately not published the specifics here, because they differ by community and they change. What I will do is give you the current, accurate picture for whichever communities you are considering, in writing, before we tour anything. There is more on the luxury homes and luxury condos pages.

Why Being Part of This Place Matters

I have lived on the Big Island for 25 years. My wife Rani and I have raised our family here, built our careers here, and committed our time and resources to this community in ways that go well beyond real estate. Most of my buyers never meet me in person before signing a representation agreement, and they want to know I am here for the long haul.

In December 2005, Rani conceived the idea for a community run to kick off Christmas week with something fun, festive, and meaningful. Together we built it into the Jingle Bell Beach Run, now one of the largest annual events in Kailua-Kona, drawing hundreds of participants every year. What started as a simple holiday run has become a charitable platform. Each year we present a Special Recognition Award to a deserving local nonprofit, with donations going to organizations supporting Big Island youth and families.

I currently serve as Board President of City SC Hawaii, the largest and most successful youth soccer club in West Hawaii. The club shapes hundreds of young athletes each year, with several players going on to compete at the collegiate and professional levels. I also volunteer as a coach. The kids on my team teach me as much as I teach them, and supporting youth sports on this island is one of the most rewarding things I do outside of work and family.

What My Clients Say

Real estate is a relationship business. The strongest endorsement an agent can offer is not their own marketing copy, it is what their clients say after the transaction closes. There are more on my reviews page.

We just moved into our awesome Kona home. Penn was extraordinarily patient and his process, understanding goals and video tours, for off-island buyers works spectacularly. He was honest and when showing us many properties, was forthright if he did not think a home was right for us. I would unconditionally recommend Penn to anyone looking for something special in Kona.
Jeff Jensen, Keauhou Estates, second-home buyer

I worked with three Realtors in Kona before landing a more long-term relationship with Penn. He was extremely responsive throughout the whole process. He was not pushy at all. Most importantly, he struck me as just a genuine, good man. He had empathy for me when I was having second thoughts multiple times throughout the process. He even had empathy for the sellers who seemed to be going through rough times. He is deeply rooted in the community, and now I admire him too.
SJ Lee, Hualalai Farms, remote work buyer

Penn went above and beyond what we ever expected of a realtor. He helped pick up my pets at the airport because our rental car was not big enough for their crates. He lent us his generator when our power was out so our groceries would not go bad. Excellent service does not even begin to cover what he provided for us, truly an amazing human being.
Clay and Kelly Foster, Kona Palisades, relocation buyers

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, 1031 exchange buyer

He listened to all our needs and was with us every step of the way, from the beginning to the end of the process. He sent us a video of our complex and the specifications, and was so knowledgeable and professional. He went above and beyond and exceeded our expectations, giving us information about the area and contractors for our unit. We could not have navigated this journey without him.
Christina De Vito, condo buyer, Waikoloa Village

We visited the Big Island from Atlanta to scope out home ownership. I searched online since we did not know any realtor and Penn was the most responsive and accommodating during our short visit. For over a year we viewed homes online. Fifteen months later we were ready to purchase. Penn knew exactly what we were looking for. In this competitive housing market he was able to close the deal in record time. Even after we closed, Penn made sure everything was fine.
Mila Krueger, Kona Palisades, relocation buyers

We truly cannot express how grateful we are for Penn’s professionalism and care throughout the entire home-buying process. What could have been incredibly stressful felt so much more manageable thanks to his knowledge and expertise. From the first meeting to the final closing, Penn was there every step of the way.
Brooke and Nick, first-time homebuyers, Kailua-Kona

Questions to Ask Any Agent

Most buyers do not interview their agents the way they should. The decision is often made before any real questions are asked, and that can cost you. Below are the questions I would ask any agent I was thinking of hiring, with my own answers included. Use them with me. Use them with anyone else you are considering.

How Long Have You Been in Real Estate on the Big Island?

I have lived on the Big Island full-time for 25 years and have been a full-time REALTOR® here since 2021. Before that I spent over 20 years in executive sales and marketing for respected West Hawaii companies. The local knowledge runs deep.

What Are Your Professional Qualifications?

A finance degree from the University of Colorado, plus active certifications including CLHMS, Certified Luxury Home Marketing Specialist at the Guild Elite tier, RSPS, Resort and Second Home Property Specialist, PSA, Pricing Strategy Advisor, e-PRO for digital marketing, and At Home With Diversity.

What Percentage of Your Business Is Buyer Representation?

Roughly 60 to 70 percent. I work both sides of the table, but most of my clients are buyers, usually mainland or international, often making one of the largest purchases of their lives without ever stepping into the property before going under contract. That experience shapes how I approach the work.

How Do You Work With Off-Island Buyers?

Detailed narrated video walkthroughs of every property we seriously consider. FaceTime showings for live, real-time tours. A custom search tuned to your specific criteria. A communication rhythm built around your time zone. Most of my buyers never set foot in a property before going under contract, and the process is built specifically to make that work.

How Do You Find Properties That Are Not on the MLS?

Mostly by asking. I approach owners directly in the communities you are targeting, and I lean on relationships with the agents who handle this island’s high-end inventory, built over 25 years here. Being part of a national brokerage adds another set of conversations. None of it is guaranteed to produce anything, but it produces more than a portal alert does.

How Do You Approach Property Due Diligence?

Before we write an offer I research recent comparable sales, current competing inventory, days on market, zoning, HOA financials and rules, rental history and short-term rental eligibility where relevant, and any red flags in the disclosure package. I will show you the work and the reasoning behind every recommendation I make.

How Do You Handle Negotiations?

Research first, then strategy. I investigate the seller’s motivations, the listing history, and the agent on the other side before I write your offer. Every offer is built with intent: price grounded in data, terms designed to win without overpaying, and a presentation that makes the listing agent want to advocate for it. Inspection negotiations get the same approach.

How Does Your Commission Work?

My compensation is set in the Buyer’s Representation Agreement before we begin, and it does not change based on which property you choose. Since the 2024 rule changes it is technically negotiable and requested as part of your offer, but in practice sellers on the Big Island continue to cover the buyer’s brokerage fee in nearly every transaction I write. If a seller declines, you will know well before we submit, and we will decide how to handle it together. No surprises at closing.

How Do You Communicate With Buyers During the Search?

Direct and frequently. Phone, text, or email, whichever you prefer. New-listing alerts the moment properties hit the MLS. Property previews and video walkthroughs as quickly as I can get them to you. Real-time updates on showings, offers, and market movement. The most common reason buyers leave their first agent and come to me is responsiveness, and I take that seriously.

Will You Pressure Me to Buy Something?

No. My job is not to sell you a house. It is to help you find the right one and walk away from the wrong ones. If a property is not right for you, I will tell you. If you need more time, you will get it. The relationship matters more to me than the transaction, and the work I am doing now is building the next 20 years of my practice, not closing a single deal.

Ask me anything else. The right agent welcomes hard questions. I would rather earn your trust by answering them than win your business by avoiding them.

Where Your Search Actually Starts

Two platforms, two jobs. pennhenderson.com is where you search and learn the island. Compass One is where your transaction lives once we are under contract. You will use both, and I will set up both.

My website is not just listings. It is packed with real insight into the different areas, communities, and lifestyles across the Big Island, so you are not just scrolling homes. You are starting to understand where you actually want to be. Start with homes for sale, condos, oceanfront, or browse the communities directly.

The internet alone gives you options, but not clarity. That is where I come in. I take the time to listen, filter through the noise, and focus on what actually fits your goals. When I send you a property it is not random. It is something I have already looked at closely and feel confident is worth your time. You are not sorting through hundreds of listings wondering what you are missing. I have already done that work for you.

Ready to Find Your Big Island Home

Whether you are ready to start your search now, planning a move a year or two out, or simply gathering information for the future, I would welcome a conversation. Reach me at (808) 345-6214 or penn@pennhenderson.com, or through the contact page.

When we sit down together, you can expect:

• A focused, no-pressure consultation built around your specific goals and timeline
• A custom search set up immediately, with new-listing and price-change alerts tuned to your criteria
• Honest market context for the communities you are considering, including pricing, inventory, and what to expect at your price point
• A clear walkthrough of the process, including financing options, short-term rental considerations, FIRPTA, and anything specific to your situation
• Honest answers to every question you ask

I have handled everything from oceanfront estates to Waikoloa condos, vacation rental investments to multi-generational family homes, 1031 exchanges to HARPTA situations. Whatever your circumstance, the experience is here to support you. If you are also thinking about the practical side of the move, my guides on moving to the Big Island and moving with pets cover the ground the buying process does not.

With aloha,
Penn Henderson, R(S), Hawaii License RS-83962
Compass, 75-1029 Henry St., Suite 301, Kailua-Kona, HI 96740

---

Copyright 2026 Penn Henderson, R(S), Hawaii License RS-83962. The Big Island Buyer’s Guide is my own original work, written from 25 years of living and working on this island. You are welcome to link to this page or quote a short passage with attribution and a link back. Reproducing it in whole or in substantial part, or rewriting it for use on another agent or brokerage website, is not permitted. Market figures are sourced to Hawaii Information Service for the period stated and are not a substitute for current data on a specific property.