Refined Hawaiian Luxury in Paradise
The Big Island of Hawaii presents an extraordinary opportunity to own a luxury home unlike any other in the world. From gated oceanfront estates on the Kona Coast to hillside sanctuaries overlooking the Pacific and sprawling ranch-style homes in North Kohala, the Big Island is home to some of Hawaii’s most exclusive and awe-inspiring properties.
With dramatic coastlines, privacy, space, and a slower pace of life, luxury living on the Big Island means more than high-end finishes—it’s about lifestyle, setting, and a deeper connection to the land and sea.
$36.5 Mil
2024 TOP Sales Price
89
2024 Luxury Home Sales ($3M+)
+ 64.8%
% Chg vs. 2023 (54)
79%
"All Cash" Sales
Penn Henderson
BIG ISLAND LUXURY REALTOR®
I’m grateful to be recognized as a trusted resource in Hawaii’s luxury real estate market, particularly along the Kona and Kohala Coast. My approach is rooted in professionalism, discretion, and a strong commitment to delivering results.
Over the years, I’ve had the privilege of representing high-net-worth clients in some of the island’s most significant transactions—something I never take for granted. With a deep understanding of the local market and a focus on client confidentiality, I strive to make every real estate experience as seamless and successful as possible.
❂ Big Island Top 3% Sales
❂ West Hawaii Realtor Award
❂ Google Top-Rated ★★★★★
❂ 24 Years of Local Hawaii Insight
Simplify Your Home Search
You’re ready to make your dream of owning a luxury home in Hawaii a reality—exciting times! But as you dive in, the variety of listings and ever-changing market conditions can quickly feel overwhelming, especially when off-island searching from the mainland. That’s where I come in.
Tell me what you're looking for—whether it's ocean views, a gourmet kitchen, resort-style amenities, or a specific location within a private luxury community. I’ll set up a personalized home search tailored to your exact criteria and send you the most relevant, up-to-date listings directly from the professional Multiple Listing Service (MLS), so you never miss a great opportunity.
❂ Ready to go? Let's start defining your Big Island luxury home search criteria now:
Hawaii Luxury Homes Sold by Penn
49 Black Sand Beach at Mauna Lani
this magnificent residence offers a private office, seven bedrooms including the primary and secondary bedroom suites, and an ideal indoor-outdoor lifestyle.
The Villas at Mauna Kea
Rarely available Villas at Mauna Kea, in one of the best front row locations within the project. Walk to the golf course, hotel, and Mauna Kea beach.
Hale Hinahina at Kohanaiki
Hale Hinahina - a unique luxury enclave of beautifully paired residences within the exclusive private club community of Kohanaiki in Kona.
Waimea Hillside Architectural Home
A one-of-a-kind Waimea familly restreat located near the top of the famed nob-hill boasing breathtaking views of surrounding areas and the Kohala Coast.
Luxury Real Estate in Hawaii
Luxury real estate on the Big Island spans oceanfront resorts, hillside estates, gated subdivisions, and large-acreage retreats. While the Kohala Coast is well-known for its resort living, true luxury can be found in multiple pockets across North Kona, Holualoa, Waimea, and Hamakua.
Top Luxury Areas on the Big Island:
North Kona (Kailua-Kona to Kaupulehu):
This region features some of the island’s most exclusive real estate, including:
- Kukio – Ultra luxury private club community with beachfront estates, Tom Fazio golf, and concierge services.
Explore Kukio Real Estate »
- Hualālai Resort – Four Seasons-branded living with private beach access, spa, golf, and club membership
Discover Hualalai Homes »
- Kohanaiki – Rees Jones golf course, state-of-the-art clubhouse, and private beachfront homes
View Kohanaiki Real Estate »
- Keauhou – Several gated luxury communities, such as Keauhou Estates and Bayview Estates, with ocean views and custom designs
View Keauhou Real Estate »
- Kailua-Kona (Non-resort luxury communities):
- Iolani – Elevated above town with sweeping coastline views
- Kona View Estates – Adjacent to Iolani. High-end custom homes with panoramic ocean views
- Alii Point – Exclusive, gated oceanfront enclave just minutes from downtown Kailua-Kona
- View Kailua-Kona Real Estate »
- Holualoa - Set above Kailua-Kona, this artist and coffee farming village features sprawling estates with ocean views, cooler elevation, and privacy. Consider areas like Hualalai Farms, Keopu Mauka, and Holualoa Estates for boutique luxury subdivisions.
Explore Holualoa Real Estate »
Kohala Coast (South Kohala District):
While sometimes used to broadly describe the region, the true Kohala Coast includes:
- Mauna Lani Resort – Gated resort subdivisions like Pauoa Beach, Ke Kailani, and The Cape at Mauna Lani
Mauna Lani Real Estate »
- Mauna Kea Resort – Luxury homes with direct access to iconic beaches and golf
Mauna Kea Real Estate »
- Waikoloa Beach Resort - Popular with second-home buyers and vacation investors
Waikoloa Beach Real Estate »
- Kohala Ranch – Gated hillside community offering large estate parcels (3–10+ acres) with panoramic ocean, sunset, and mountain views
View Kohala Ranch Real Estate »
Waimea (Kamuela):
High-elevation estates and pastureland luxury properties. Notable enclaves include:
- Nob Hill (Buster Brown Hill) – Panoramic town views, near schools and the town center
- Sandalwood - High-end homes on the dry side of Waimea, near HPA private school
- Waiki'i Ranch, Kanehoa, and surrounding acreage homes
Hāmākua Coast & Mauka Retreats:
For buyers seeking acreage, waterfalls, and privacy, look to:
- Laupāhoehoe, Hakalau, Nīnole, and Honoka‘a – Custom-built homes and estates with ocean views
- Mauka farms and forested properties with potential for self-sufficient living or boutique agriculture
Explore Hilo & Hamakua Real Estate »
Hokuli‘a (South Kona):
Gated golf course private community with one-acre+ homesites, luxury custom homes, and a Jack Nicklaus Signature Course. Club membership is required for access to amenities.
Discover Hokulia Real Estate »
Common Features of Luxury Neighborhoods:
- Gated entry and private roadways
- Ocean or mountain views
- High-end architecture and finishes
- Clubhouses, private beach clubs, and golf access
- Secluded lots and estate privacy
Helpful Resources:
Yes, many luxury homes on the Big Island are located outside of HOA-managed communities. While gated resorts and private clubs are popular among high-end buyers, some prefer the freedom, privacy, and flexibility of owning a luxury home without the oversight or monthly fees of a homeowners association.
Popular Areas for Non-HOA Luxury Homes:
Holualoa
Mauka of Kailua-Kona, Holualoa offers estate-style properties, coffee farms, and custom homes on acreage, with minimal HOA restrictions.
Explore Holualoa Real Estate »
North Kona
Neighborhoods like Iolani, Kona View Estates, and Keopu Mauka feature upscale homes with expansive views, many of which are available without HOA fees.
Hāmākua Coast
From Honokaʻa to Hakalau, this scenic coastline features oceanfront and bluff-top estates with large parcels, privacy, and agricultural flexibility, without association dues.
Explore East Hawaii Properties »
Waimea & North Kohala
Areas such as Nob Hill, Kohala Estates, and ag-zoned Waimea acreage lots offer luxury living near town with no HOA, ideal for those seeking independence.
View Waimea Homes & Land »
Why Choose a Non-HOA Luxury Home?
- More freedom for design and use (e.g., vacation rental potential, agriculture, guest houses)
- No association dues or restrictions
- Larger lots with more privacy
- Ideal for buyers seeking a self-sufficient or custom lifestyle
Things to Keep in Mind:
- You may be responsible for your own road maintenance, security, or utility access
- Property values in non-HOA neighborhoods can vary more widely
- Short-term rental use may still be regulated by zoning, not just HOA rules
Helpful Links:
The Big Island is home to some of the most exclusive real estate in all of Hawaii. These ultra-luxury communities offer private club memberships, oceanfront estates, world-class golf courses, and concierge services tailored for discerning buyers seeking privacy, security, and resort-level amenities.
Top-Rated Luxury Communities:
1.) Kukio (North Kona)
A private, members-only oceanfront enclave near the Four Seasons Hualalai. Offers two Tom Fazio golf courses, a private beach club, concierge services, and estate-sized homesites. Explore Kukio Real Estate »
2.) Hualālai Resort (North Kona)
Home to the Four Seasons Hualalai, this gated resort features custom homes, villas, and a renowned golf course. Membership grants access to the Ke‘olu Clubhouse, Canoe Club, spa, and tennis facilities. View Hualalai Resort Homes »
3.) Kohanaiki (North Kona)
A 450-acre private club community with oceanfront estates, a Rees Jones golf course, and a 67,000 sq. ft. clubhouse offering luxury amenities and wellness services. Browse Kohanaiki Real Estate »
4.) Mauna Kea Resort (South Kohala)
Luxury living with two championship golf courses, private beach clubs, and proximity to iconic beaches like Kauna‘oa and Hapuna. Features estates, villas, and townhomes. Mauna Kea Real Estate »
5.) Mauna Lani Resort (South Kohala)
Includes several ultra-luxury subdivisions, such as Pauoa Beach, 49 Black Sand Beach, Ke Kailani, and Nohea, offering beachfront estates, golf, and wellness-focused living. Mauna Lani Real Estate »
6.) Hokuliʻa (South Kona)
A gated, 1,260-acre oceanfront development with large one-acre+ lots, a Jack Nicklaus Signature golf course, clubhouse, pool, fitness, and dining facilities. Discover Hokulia Real Estate »
Why These Communities Stand Out:
- 24/7 gated security and privacy
- Clubhouse amenities (spa, dining, fitness, golf, concierge)
- Private beach access and oceanfront trails
- Strong resale value and high demand from global buyers
Helpful Resources:
Yes. While Hawaii’s overall property tax rates are among the lowest in the U.S., certain luxury properties may be subject to higher tax classifications, depending on their use, location, and value.
Key Tax Considerations for Luxury Homeowners:
Property Tax Classification
Each county assigns tax rates based on the type of property use. For example, Hawaiʻi County (Big Island) applies different rates for:
- Homeowner (primary residence) – Lower rate
- Residential (second homes or vacant homes) – Higher rate
- Residential Tier 2 – Applied to the portion of assessed value exceeding $2 million for non-owner-occupied properties
Transient Accommodations Tax (TAT)
If you rent your property short-term (less than 180 days), you must pay:
- Hawaii State TAT: 10.25%
- Hawaiʻi County Surcharge: 3%
- This applies even if the property is in a resort zone
Learn More About TAT (PDF) »
General Excise Tax (GET)
Hawaii charges a 4.5% tax on rental income, including long-term and short-term rentals.
- Must register for a GET license
- Applies to furnished rentals, even occasional vacation use
Capital Gains Tax
When selling, luxury homeowners may be subject to federal capital gains and Hawaii’s capital gains tax of 7.25% (if applicable).
- HARPTA (7.25% withholding for non-residents) may also apply at the sale.
Tips for Buyers and Sellers:
- Check the current assessed value and tax classification with Hawaiʻi County
- Ask about tax implications for short-term rental use or second-home status
- Work with a knowledgeable real estate professional to understand how taxes may impact your purchase, use, or sale
Helpful Resources:
Off-market luxury properties—often referred to as “pocket listings” or “quiet listings”—are homes that aren’t publicly advertised on the MLS or major real estate platforms. These properties are typically made available through private networks and trusted relationships within the luxury real estate community.
How to Access Off-Market Listings:
Work with a Trusted Luxury Agent
Agents like Penn Henderson often have direct access to off-market inventory through their local network of high-net-worth clients, developers, and brokers. These relationships are key to gaining early or private access to exclusive homes.
Meet Penn Henderson »
Join a Prequalified Buyer Network
If you’re a serious buyer, Penn can help position you as a qualified prospect to sellers who may be open to discreet offers. This often involves verification of financial capability, especially for high-value listings.
Contact Penn to Begin Your Search »
Attend Private Showings & Events
High-end properties are sometimes revealed at invitation-only viewings or through targeted networking. Being present in the local market—or having representation—matters.
Target Communities with Known Off-Market Activity:
Why Sellers Choose Off-Market Sales:
- Privacy and discretion
- Avoiding days-on-market metrics or public price reductions
- Testing buyer interest before formal listing
- Reducing exposure to the general public
Helpful Resources:
Many luxury homes on the Big Island are offered fully or partially furnished, especially those in resort communities or used as second homes and vacation rentals. However, furnishings can vary widely in quality, completeness, and whether they are included in the sale price.
Common Scenarios:
Turnkey Properties:
These homes are move-in ready and typically include high-end furnishings, appliances, housewares, and sometimes artwork. Common in resort areas like Mauna Lani, Mauna Kea, and Hualālai.
Browse Big Island Luxury Homes »
Vacation Rental Properties:
If the home has operated as a short-term vacation rental (STVR), it often comes fully equipped to continue rental operations, including linens, kitchenware, electronics, and decor.
Learn About STVR Homes on the Big Island »
Custom Estates or Primary Residences:
These may or may not be furnished. Sellers sometimes prefer to keep personal furnishings or custom art. Negotiations can include the option to purchase furniture separately.
Tips for Buyers:
- Always review the inventory list provided during escrow to see what’s included
- High-end furniture packages can carry significant value, sometimes $100,000+
- Ask your agent (like Penn) to negotiate furnishings into the sale if they’re desirable
- Custom-built homes may feature built-in furniture or luxury appliances that stay regardless
Helpful Resources:
Luxury homes in Hawaii—especially on the Big Island—combine high-end architecture, prime locations, luxurious lifestyles, and custom design elements that showcase the natural beauty of the islands. While price is a factor, what truly defines a luxury property is the quality of experience it delivers.
Defining Features of Hawaii Luxury Homes:
Location, Views & Privacy
Prime oceanfront lots, elevated estates with panoramic coastline views, or secluded properties on acreage are all hallmarks of Big Island luxury.
Indoor-Outdoor Living Design
Seamless transitions between indoor and outdoor spaces with features like pocketing glass walls, lanais, infinity pools, and tropical landscaping.
Custom Architecture & Materials
Luxury homes often incorporate exotic hardwoods, volcanic rock accents, coral stone, custom cabinetry, and bespoke furnishings.
Smart Home Technology
Integrated security, lighting, audio, and climate systems are standard in many new builds and renovated estates.
Gourmet Kitchens & Spa-Like Baths
Chef-level kitchens, featuring Wolf/Sub-Zero appliances, wine cellars, and oversized islands, are common. Similarly, master baths often include soaking tubs, outdoor showers, and high-end finishes.
Resort-Level Amenities
Many homes—particularly in communities like Kukio, Hualālai, or Mauna Kea Resort—offer access to private clubs, golf courses, concierge services, fitness centers, and private beach clubs.
Sustainability & Energy Efficiency
Luxury properties are increasingly featuring solar arrays, Tesla Powerwalls, water catchment systems, and green building certifications, especially in mauka (upland) areas.
Notable Add-Ons:
- Guest houses or ohanas
- Detached studios or home offices
- Gated entrances and long driveways
- Lava rock walls and tropical gardens
- Home theaters and wellness rooms
Helpful Resources:
Yes. Financing a luxury home in Hawaii is absolutely possible, but the process is more specialized than a typical mortgage. Jumbo loans, portfolio lending, and asset-based underwriting are often required for high-value purchases, especially those exceeding conforming loan limits.
Financing Options for Luxury Buyers:
Jumbo Loans
These are mortgage loans that exceed the standard loan limits set by Fannie Mae and Freddie Mac (currently around $1,149,825 for most of Hawaii). Jumbo loans typically require:
- Higher credit scores (720+)
- Larger down payments (15–30%)
- Strong debt-to-income ratios
- Extensive income and asset documentation
Portfolio Lending
Private banks and local credit unions may offer portfolio loans to high-net-worth clients. These loans are kept in-house (not sold on the secondary market) and offer more flexible terms, often tailored to the borrower's entire financial profile.
Asset-Based Loans
In some cases, buyers can qualify based on their overall assets rather than income, especially for second homes or investment properties. This is common with self-employed or retired buyers with significant holdings.
Cash Purchases
A large number of luxury transactions in Hawaii are all-cash, particularly in ultra-exclusive communities like Kukio, Hualālai, and Kohanaiki. Cash offers often provide stronger negotiating power and faster closings.
Explore Ultra-Luxury Communities »
Tips for Financing Success:
- Work with a lender who specializes in Hawaii real estate and jumbo products
- Get pre-approved before touring properties—this strengthens your position when making offers
- Consider institutions familiar with Hawaii luxury transactions (e.g., Bank of Hawaii, First Hawaiian Bank, Wells Fargo Private Banking)
Helpful Resources:
Deciding whether to build or buy a luxury home in Hawaii, particularly on the Big Island, depends on your goals, timeline, and personal vision. Both paths offer unique advantages, but also come with important considerations specific to island living.
» Buying a Luxury Home:
For many buyers, purchasing an existing high-end property offers a streamlined path to ownership.
Pros:
- Move-in Ready: Many luxury homes in areas like Kukio, Hualalai, or Mauna Lani are fully furnished, turnkey properties.
- Established Landscaping & Infrastructure: Gated communities often offer mature landscaping, roadways, utilities, and amenities already in place.
- Proven Design: You can see exactly what you're buying—layout, views, finishes, and how the home performs in the environment.
Considerations:
- Inventory is limited, especially in premier communities like Kohanaiki or Mauna Kea.
- Customization may be limited unless you're willing to remodel.
» Building a Luxury Home:
If you have a specific vision, building a custom estate may be ideal, especially on larger acreage properties in areas such as Hamakua, Holualoa, or North Kohala.
Pros:
- Full Customization: Design a one-of-a-kind residence to fit your lifestyle, with the materials, layout, and features you want.
- Access to Larger Lots: Areas like Kohala Ranch or mauka (upcountry) Waimea offer more space, views, and privacy.
Considerations:
- Longer Timeline: Permitting, site prep, design, and construction can take 18–36 months or more.
- Higher Upfront Costs: Land acquisition, architectural design, and construction can often exceed the cost of buying an existing home, especially with rising material and labor costs.
- Zoning & Infrastructure: Some rural areas may have off-grid requirements, limited access to utilities, or stricter design guidelines.
Final Thoughts:
- If you’re seeking resort-style living with club amenities and beach access, buying in an established community may be the most practical route.
- If you’re looking for a private retreat with acreage, agricultural potential, or a unique architectural vision, a custom-built home may offer the lifestyle you want.
Helpful Resources:
Possibly, but it depends on the property's zoning, location, and whether it has a valid Short-Term Vacation Rental (STVR) permit. On the Big Island, vacation rentals are tightly regulated, especially outside designated resort zones. Understanding these rules is essential before purchasing a luxury property with rental income potential.
Where Vacation Rentals Are Generally Allowed:
Resort-Designated Areas
Homes and condos within official resort zones, such as Mauna Lani, Mauna Kea, Waikoloa Beach Resort, Hualālai, and Kohanaiki, are typically allowed to operate as a Short-Term Vacation Rental with a valid (STVR) permit. These areas are pre-approved for vacation use, but may be subject to stricter HOA rules.
Non-Resort Areas (Kailua-Kona, Holualoa, etc.)
If the property is not in a resort zone, you’ll need a non-confirming use certificate (NUC) and a valid STVR permit issued by Hawaii County to operate short-term rentals legally. Many permits were grandfathered in before the 2019 regulation changes.
Learn More About Hawaii STVR Rules »
What to Know About STVR Permits:
- Permits stay with the property (not the owner) and must be renewed annually
- New permits are no longer being issued for properties in certain residential/agricultural zones
- Noncompliance can result in steep fines and legal issues
Tips for Buyers:
- Always verify if a property has an active STVR permit before making an offer
- Work with a knowledgeable agent (like Penn) who understands zoning regulations and can help you identify income-producing properties
- Properties with existing rental history and strong reviews often command a premium.
Helpful Resources:
- Hawaii County STVR Overview
- Contact Penn for STVR Listings.»
- Big Island Buyer’s Guide »While it’s possible to purchase a condo without a buyer’s agent, having professional representation is highly recommendspeciawhere real estate laws, ownership structures, and condo-specific rules differ from the main
Why Work with a Local Agent:
Understanding Leasehold vs. Fee Simple:
A local agent can help you avoid surprises by explaining the legal and financial differences between these two ownership types, which are more common in Hawaii than elsewhere.
Guidance on HOA Rules, Fees & Restrictions:
Your agent will help you review pet policies, vacation rental rules, reserve funding, and other important details before submitting an offer.
Expert Navigation of Local Escrow & Title Process:
Hawaii’s real estate system has unique steps, timelines, and regional customs. A knowledgeable agent ensures nothing is overlooked.
Access to Off-Market & Upcoming Listings:
Many luxury and investment properties are not publicly listed. Agents often have insider access to these opportunities.
Contract Negotiation & Due Diligence:
Your agent works to protect your interests, helps coordinate inspections, reviews condo documents, and ensures key deadlines are met.
Helpful Resources: