Big Island Hawai‘i Real Estate

Featured Big Island Properties

I’ve called the Big Island home for over 25 years. Let me help guide the way.

Penn Henderson, R(S)
(808) 345-6214

  • Tiki torches on Big Island Hawaii property, Kona coast, creating a tropical, luxurious outdoor ambia.
  • Top Kona Realtor - Penn Henderson - Big Island Hawaii Real Estate.
  • Oceanfront Hawaii condo with stunning coastal views in Kona and Kohala Coast.
  • Luxury Big Island Hawaii home near Kona with stunning ocean and mountain vistas.
  • Traditional Tiki statues on Big Island Hawaii beachfront, showcasing Polynesian culture and coastal.
  • Coffee farm in Kona, Big Island Hawaii with lush greenery and mountain views.
  • Stone pet sculpture on Big Island, Kona, Kohala Coast lifestyle, outdoor art piece.
  • Hawaiian luxury home with lush gardens in Kona and Kohala Coast.
GETTING STARTED

Find Your Home on the Big Island

Homes

Elegant homes for sale on the Big Island featuring a private pool, spacious outdoor living, and stunning ocean vistas.

Residential homes across Kona, the Kohala Coast, and Waimea. From upcountry ranches to turnkey resort properties.

VIEW

Condos

Big Island condos for sale with a bright kitchen and ocean views in Kona, Hawaii.

Turnkey island living with resort amenities. Top picks in Kailua-Kona, Keauhou, Waikoloa Beach Resort, and Mauna Lani.

VIEW

Land

Big Island vacant land for sale in Hawaii, Kona, Kohala Coast, tropical scenery, waterfalls.

Build your Hawaii dream from the ground up. Agricultural, residential, and ocean-view parcels across the Big Island.

VIEW

Oceanfront

Oceanfront property in Kona with lush palm trees and coastal views.

Direct ocean access, sunsets, and many with strong vacation rental upside. The most sought-after homes on the Big Island.

VIEW

Luxury

Modern Kona estate with outdoor living, tropical landscape, and sunset vistas.

Estate homes and resort residences at Hualalai, Kukio, Kohanaiki, Mauna Kea, and more. Curated for discerning buyers.

VIEW

Search

Search Big Island MLS: Oceanview Big Island Hawaii real estate with tropical garden and sunsets.

Browse all 3,000+ active Big Island listings updated by the minute. Filter by location, price, property type, and more.

VIEW

Featured

Big Island Properties

Get to Know

Big Island Areas

North Kona

Kailua-Kona, Keauhou, Holualoa, oceanfront condos, and the primary business hub of West Hawai‘i.

VIEW

Kohala Coast

Beachfront property in Kona, Big Island Hawaii with ocean views and luxury lifestyle.

Resort living, world-class beaches, golf, investment properties, exclusive estates, and plenty of sunshine.

VIEW

South Kona

Oceanfront estate on Big Island Hawaii with stunning coastal and mountain views near Kona and Kohala.

Coffee country, ocean views, acreage, semi-rural with numerous charming Vintage Hawai’i towns.

VIEW

Waikoloa Village

Luxury golf course home in Kona with ocean views and resort amenities.

Large inventory of residential homes, condos, and building lots with easy access to beaches and Kohala Coast amenities.

VIEW

Waimea

Luxury homes in Kona and Kohala Coast with lush green hills and ocean views.

Artsy-eclectic, cooler upcountry living with mountain views, ranch estates, and home to the island’s top private schools.

VIEW

North Kohala

An authentic slice of old Hawai‘i charm. Historic, rural, and dramatic. The northern part of the Big Island.

VIEW
+ Hamakua + Hilo + Puna + Ka’u
Explore the Big Island Map North Kona South Kona Kohala Coast Waikoloa Village Waimea North Kohala Hamakua Hilo Puna Kaʻu
North Kona
South Kona
Kohala
Coast
Waikoloa
Village
Waimea
North
Kohala
Hamakua
Hilo
Puna
Kaʻu
North KonaNorth Kona
South KonaSouth Kona
Kohala CoastKohala Coast
Waikoloa VillageWaikoloa Village
WaimeaWaimea
North KohalaNorth Kohala
HamakuaHamakua
HiloHilo
PunaPuna
KaʻuKaʻu

Explore the Big Island

EXPERT REPRESENTATION

Your Trusted Guide to Hawai‘i Real Estate on the Big Island.

I’m Penn Henderson, a full-time Kona resident since 2001 and one of the Big Island’s top-rated REALTORS®, focused primarily on West Hawai‘i. Most of my clients are coming from the mainland, making a significant financial and lifestyle decision from thousands of miles away. They need more than a search portal. They need a local expert who can tell them what the MLS can’t.

That’s what I bring to every transaction: deep local experience, a proven track record of results, and the kind of expert representation that only comes from truly calling this island home.

Contact About
Hawai‘i Expertise
BIG ISLAND Agent
Annual Sales
Google Rated
MARKET YOUR HOME TO SELL

Selling

Get a clear plan designed for today’s Hawai‘i market. From pricing strategy and professional marketing to negotiation and closing, every step is built to protect your equity and maximize your results.

  • Local Market Intelligence
  • Resort & Luxury Expertise
  • Savvy Marketing. Real Results!
My Selling Approach Big Island Seller’s Guide
Selling Big Island Hawaii real estate: Top Kona Realtor and Big Island Listing Agent - to Sell Your Home Fast.
Finding a Home on the Big Island. Kona and Kohala Coast homes for Sale.
FIND YOUR IDEAL HAWAI‘I HOME

Buying

Search smarter with local insight into Big Island neighborhoods, zoning, and market trends. Whether you’re relocating, investing, or buying your first home in Hawai’i, I provide expert guidance from search to closing.

  • Seamless Remote Buying Process
  • Off-Market & Resort Expertise
  • Local Knowledge. Real Advantage!
How I Help Buyers View My Buyer’s Guide
success stories

Read What My Clients Are Saying

Buying and selling property in Hawai‘i is one of life’s most exciting journeys. These are the stories of clients we’ve helped guide the way.

41+
Google ★★★★★
Client Experiences

Penn was extraordinarily patient, and his process for off-island buyers works spectacularly.

– Jeff Jensen (Buyer)

On a scale of 1 to 5, we would rate him a 10! He went above and beyond what you would expect from a real estate agent.

– Cindy & Dave (Buyers)

He was extremely detail-oriented and knew everything going on in the market. Always communicating without any surprises.

– Steve S. (Seller)

FAQ

Common Questions About Buying Real Estate on The Big Island.

It depends on how you plan to use it. Kailua-Kona and Keauhou suit buyers who want walkability, ocean access, and strong short-term rental potential. The Kohala Coast resort communities, Waikoloa Beach Resort, Mauna Lani, and Mauna Kea, offer amenities, gated security, and established rental programs with on-site management. Waimea draws buyers who want cooler weather, upcountry ranching character, and a quieter pace fifteen minutes from the coast. There is no universally best answer, only the right fit for how you actually plan to spend your time here. That is the first conversation I have with every buyer.

The whole island, with the depth concentrated in West Hawaii. Kailua-Kona, Keauhou, the Kohala Coast, and Waimea are where I live, where I sell, and where I can tell you which unit in a project gets the afternoon trade winds and which one gets the parking lot. I also represent buyers and sellers in Hilo, Volcano, and the Hamakua Coast. If you are seriously considering the east side, I will tell you honestly how my knowledge of it compares.

More than most buyers expect. Leasehold ownership, CPR structures, and Hawaiian Home Lands do not exist in most states. Lava hazard zones affect insurance and financing. HARPTA and FIRPTA withholding applies when non-resident owners sell. Vacation rental eligibility is governed by county zoning, which varies from street to street and can determine whether a property pencils at all. Contracts here are date-driven rather than contingency-driven, and closing occurs when the deed is recorded in Honolulu, not at a signing table. None of it is difficult once someone walks you through it, but it is not the process you went through in Denver.

Sometimes, and it is entirely property-specific. Short-term vacation rental permits are issued by Hawaii County, tied to the property rather than the owner, and require annual renewal. Resort-zoned properties along the Kohala Coast and in parts of Kona are generally eligible. Elsewhere, eligibility depends on zoning, permit history, and whether the AOAO or CC&Rs allow it regardless of what the county says. Verify before you make an offer, never after.

It can be, and the spread between a good one and a bad one is wide. A permitted unit in a high-demand location commands a real premium over an identical unit without a permit, and that premium exists because the income is genuinely different. What separates the properties that work from the ones that disappoint is honest math: actual occupancy for that specific project, rather than island-wide averages; maintenance fees; management splits; GET and TAT; insurance; and what the AOAO permits. I will run those numbers with you before you write an offer, and I will tell you when they do not work.

The range is wide. At Waikoloa Beach Resort, condos generally start in the $800,000 to $900,000 range, with single-family homes running $1M to $2M and above. Mauna Lani and Mauna Kea resort properties typically begin around $1.5M and climb well into eight figures for oceanfront and estate parcels. The private club communities of Hualalai, Kukio, and Kohanaiki occupy their own tier, with most transactions starting near $5M. Inventory and rates move these numbers, so treat them as orientation rather than gospel and reach out for a current picture at your price point.

Most of my clients are three thousand miles away, so the practice is built for it. I preview properties on video, walk the neighborhood, and tell you about the road noise and the afternoon sun that photos never show. I attend inspections on your behalf and send you the findings the same day. Documents are handled electronically, and escrow can arrange remote notarization. When you do fly out, the trip is spent efficiently touring a shortlist rather than starting from scratch.

A real shift, and for the right person, extraordinary. The pace is slower, the community is small enough that you will run into your contractor at the grocery store, and West Hawaii gets sun close to year-round. You can swim, hike, or paddle any day you choose. The Ironman World Championship comes down Alii Drive every October, and I have raced it three times. The farmers’ markets and the sense of aloha are not a tourism veneer. The trade-offs are real, too: shipping costs, limited retail options, long travel days to the mainland, and a cost of living that requires planning rather than optimism. I moved here in 2001 and raised my family here. I will give you the honest version.

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, Compass Hawaii

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

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