Big Island Seller’s Guide

Prefer to read rather than flip? The complete guide follows below: pricing, preparation, marketing, the launch window, escrow, and the Hawaii tax rules that catch non-resident sellers off guard.

What This Guide Covers

This is the full text of my Big Island Seller’s Guide, the same guide in the flipbook above. It covers how a Big Island sale actually works: valuation and pricing, preparation, marketing and launch, offers and negotiation, escrow, and the tax rules specific to Hawaii, including HARPTA, FIRPTA, and 1031 exchanges.

I wrote it for the seller I work with most often. Someone on the mainland with a Big Island vacation home, an investment property, or the house where they raised a family, managing the whole sale from a thousand miles away. If you are on the other side of the transaction, my Big Island Buyer’s Guide covers the purchase side in the same detail.

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 home I represent.

If you are thinking about selling your Big Island home, you already know this is more than a transaction. Whether it is a vacation home you are ready to part with, an investment property, or the place where you raised a family, the decision to sell carries weight. You deserve an agent who treats it that way.

The Big Island remains one of the most desirable places in the world to own real estate. Demand is real, but the market is more nuanced than ever. Even in strong conditions, I watch homes sit, sell short, or quietly underperform simply because the agent did not do the work. Outdated photography. Lazy pricing. Generic marketing. No follow-through. 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 listing. I price strategically, market aggressively across digital and traditional channels, and stay engaged from our first conversation through the day escrow closes. I do not cut corners, and I do not disappear after the listing goes live.

Marketing under the Compass brand now gives my sellers something this market has rarely seen: a launch strategy built around the first two weeks your home is on the market, tools made for owners managing a sale from thousands of miles away, and a reach that extends well beyond our shores.

This guide walks you through how I approach the sell side of a transaction, from market analysis and pricing to marketing, escrow, and the tax considerations specific to Hawaii. It is the same process I use whether I am representing a Waikoloa Village condo or a Kohala Coast estate.

Here is my sincere guarantee. Allow me to lead your Big Island sale, 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 I Sell Under Compass

When you list with me you get two things at once: the focused attention of a solo agent who runs every detail of your sale personally, and a national platform working behind it. Compass gives me a disciplined launch sequence, a transparent dashboard that keeps remote sellers informed in real time, and a luxury division built for the top of the market.

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 Sale You Can Follow From Anywhere

Compass One gives you one secure place to watch your sale in real time: your timeline, every document, live listing performance, and your full team. Most of my sellers manage their sale from the mainland, often across three or four time zones, and this is built for exactly that.

Reach a Buyer Pool No Single Agent Has

Compass.com is the most visited traditional brokerage website in the country, drawing more than 7.5 million monthly visitors, and the Compass partnership with Redfin extends a listing to a further 60 million active buyers. Those are national platform figures rather than a forecast for any one property, but the distribution is real and your listing plugs into it from day one.

Buyer Demand Visible Before We Launch

Before your home is even photographed, I can see buyer activity across a national network of Compass agents and the clients they represent, then reach the agents whose buyers are already searching for a property like yours. Knowing where the demand sits before launch changes how I position and price.

Global Reach for the Island’s Finest Homes

For qualifying luxury properties, Compass extends your home to an international audience of high-net-worth buyers through wealth-mapped targeting, a dedicated luxury platform, and global channels most brokerages cannot access. The full detail on that layer sits further down this guide.

Compass gives my sellers a platform no other brokerage can match. I make sure it always feels personal.

How I Approach Listings

Selling a home on the Big Island is not complicated. Doing it well is. The island has roughly 1,600 licensed real estate agents, and the average one closes three to four transactions a year. Most work part-time, between other jobs, or in a second career they fell into. 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. I do this full-time. I work harder than the agents I compete against, I invest in the systems that produce results, and I treat every listing, whether a Waikoloa condo or a Kohala Coast estate, like the financial decision it is for my client.

When you list with me, here is what I am committing to.

Pricing Built on Analysis, Not Guesswork

My finance background is not decorative. Every listing starts with a real comparative market analysis, a study of buyer behavior at different price points, and an honest conversation about timing. I would rather lose a listing by giving you an accurate, data-backed number than win one by telling you what you want to hear and then watching your home sit. You can start with an estimate of your home’s value before we ever meet.

Marketing That Earns Its Budget

Most agents talk about marketing. I run it as a discipline. Professional photography, twilight and aerial drone, video walkthroughs, 3D tours, a custom property website, broad syndication, and targeted digital advertising, plus a site I have spent years optimizing for search and AI visibility. All of it deployed before your home ever shows, all of it paid for by me.

Work Ethic, Not Lip Service

I do not disappear after the listing goes live. I attend my own showings. I host my own open houses. I write my own listing descriptions. I personally meet appraisers at the property. I report on traffic and feedback throughout. The most common reason sellers leave their first agent and come to me is responsiveness, and I take it seriously.

No Shortcuts

There is a right way to prepare a home, list it, market it, and negotiate it through closing. I know what that looks like, and I do it the same way every time. No skipped inspections, no lazy photos, no rushed disclosures, no figuring it out later. Doing it right the first time is faster, cleaner, and almost always nets you more.

Is Now the Right Time to Sell

There is no universal answer, and any agent who tells you there is should make you nervous. The right time depends on your financial picture, your tax situation, your life plans, and the specific corner of the Big Island market your property sits in. What I can do is help you think it through clearly.

Deciding when to sell is as personal as deciding when to buy was. When we sit down for a listing consultation, we walk through the full set of factors that should shape your decision and timeline. Some are personal, some are market-driven, some are tax-driven. Together they tell us whether now is the right window, or whether waiting six months changes the math.

Here is the framework I use.

Home Prices

The median price for a West Hawaii home is roughly $1.19M, up more than 120 percent since 2015. If you bought before the run-up, you may be sitting on substantial equity. The real question is not whether prices are high, but whether they are at the right point on the curve for your neighborhood and property type.

Interest Rates

About half of Big Island sales involve financing. When rates rise, the buyer pool narrows. When they ease, demand returns quickly. Rate movement affects how long your home sits and how much leverage you have when offers arrive.

Tax Position

A 1031 exchange can defer capital gains entirely when you reinvest in another property. The primary residence exclusion can shield up to $250,000 in gains if single, or $500,000 if married, under specific conditions. HARPTA and FIRPTA withholding apply to non-resident sellers. Your tax situation is often the single biggest variable in timing a sale, and it is covered in full later in this guide.

Property Condition

Homes that show well sell faster and for more. If yours needs paint, landscaping, minor repairs, or a deeper refresh, that prep window is part of the timeline. I help you decide what is worth doing, what is not, and what you can skip without losing value.

Future Plans

Where do you want to be in two years, or five? A move closer to family, a downsize, a 1031 into income property, a relocation off-island, a retirement transition. Knowing the destination shapes the strategy.

Financial Goals

Selling is a capital event. For some clients the proceeds fund the next chapter. For others they are redeployed into investments or a different property here on the island. The reason behind the sale should inform both its timing and its approach.

Together we evaluate the full context, financial, emotional, and situational, and build a timeline tailored to your situation.

The 2025 Year-End Market

Pricing your home well starts with understanding the market it is competing in. At the close of 2025, the median West Hawaii home price stood at roughly $1.19M, an increase of more than 122 percent since 2015. Those are island-wide figures, and they are a starting point rather than an answer for any single property.

• West Hawaii median home price: roughly $1.19M
• West Hawaii median price increase since 2015: more than 122 percent
• Districts covered: North Kohala, South Kohala, North Kona, and South Kona

Figures are 2025 year-end, source Hawaii Information Service, compiled by Penn Henderson, R(S).

When we sit down for your listing consultation, I bring this same level of detail filtered to your neighborhood, your price point, and the buyer pool actively shopping for properties like yours. You can also see what I have recently sold across the island.

Who Actually Buys Big Island Property

Strategy starts with knowing who is shopping for your home. A remote-working couple from Portland evaluating a Waikoloa condo is making a fundamentally different decision than a retired surgeon from Newport Beach considering a Kohala Coast estate. Their financing differs. Their timelines differ. The features they care about differ. So do the channels where they find listings.

Knowing who is most likely to buy your specific property shapes everything that follows: how I price, how I photograph, how I describe it, where I advertise, and how I negotiate. Every property I list gets matched to its most likely buyer, and every marketing decision flows from there. These are the five buyer profiles I see most often.

Off-Island Second-Home Buyers

Mainland and international buyers looking for a vacation home, a retirement landing pad, or a future relocation property. Most of mine come from California, the Pacific Northwest, Texas, Colorado, and Arizona. They are affluent and deliberate, often visiting several times before deciding, and they buy remotely. Professional photography, video, and 3D tours are how the home actually gets seen.

Telecommuters and Lifestyle Relocators

Remote-working professionals, often in their 40s and 50s, trading mainland cost-of-living for the Big Island lifestyle. This segment has grown substantially since 2020 and keeps expanding. They care about reliable internet, layouts that work for working from home, and proximity to what drove the move: beaches, trails, community, and climate. My guide to moving to Hawaii is often the first thing they read.

Investors and Vacation Rental Buyers

Buyers focused on income-producing property, particularly STVR-eligible condos and homes in resort communities. They evaluate on the numbers: gross rental income, occupancy, HOA structure, STVR zoning, and net cash flow. Marketing to them requires accurate income data, rental history, and clear documentation of zoning compliance.

Retirees

Buyers in their 60s and 70s planning a full or part-time relocation. They prioritize single-level living, low-maintenance property, proximity to medical care, and easy access to family on the mainland, where Kona’s direct flights matter. They tend to be cash or strong-financing buyers who decide on a measured timeline.

Kamaʻaina

Local Big Island families upgrading, downsizing, or relocating within the island. They know the neighborhoods and the market, and they are often making multi-generational decisions. This audience calls for a different tone and a different emphasis: community, schools, family layouts, and long-term value.

How I Value a Big Island Home

Pricing is the most consequential decision we make together, and it deserves more than a hunch. I think about it the way an analyst thinks about valuation: gather the data, weight the variables, model the scenarios, and arrive at a defensible number. Then I test it against what is actually happening in the market right now.

That discipline matters because the alternative, pricing on emotion, optimism, or what an agent thinks a seller wants to hear, is the single most common reason Big Island homes underperform. My valuation process has three layers.

Comparative Market Analysis

I start with a rigorous CMA: recent sales of comparable properties, active competing listings, expired and withdrawn listings, and pending sales waiting to close. Each comp gets adjusted for square footage, lot size, view, age, condition, location, and amenities. The output is not a single number. It is a defensible range, with every comp and adjustment documented so you can see exactly how I got there.

Market Conditions and Buyer Behavior

A CMA tells us what homes have sold for. It does not tell us what is happening right now. I layer in current market velocity, absorption rate, the interest-rate environment, and seasonality. I also analyze buyer behavior across price tiers: where the active buyer pool is concentrated, and where the gaps are.

Property Positioning

Every property has a story, and where I place it in the market shapes how buyers respond. A home priced at $1.95M attracts a different buyer pool than the same home at $2.05M, even though the gap is only 5 percent. I think carefully about price thresholds, search-filter cutoffs, and how your property compares to the active competition. The goal is not just the right number. It is the right number positioned correctly.

When we sit down for your listing consultation, I bring the full analysis: comps with adjustments, market velocity data, buyer-pool analysis, and a recommended pricing strategy with the reasoning behind it. You will see the math. You will see the logic. And you will have everything you need to make an informed decision about how to price your home.

Why Price Drives Everything

Pricing is not just about the number. It is about how that number interacts with two forces largely outside anyone’s control: the size of the buyer pool, and the timing of buyer attention. The right price exposes your home to the largest qualified buyer pool at the moment they are most likely to act.

The Buyer Pool

Price your home 10 percent above market value, and you have already eliminated a large share of the buyers actively shopping in your range. Price it at market, and the majority of qualified buyers will see it. The pyramid is mathematical, not theoretical. Every dollar above accurate market value is a dollar that narrows your audience.

The Window of Maximum Attention

Buyer attention peaks in the first one to two weeks a property hits the market. Real estate behaves like any other launch: new attracts attention, familiar gets ignored. If your home is priced wrong during that window, you have spent the most valuable marketing asset you will ever have, newness, without converting it into offers.

Combine the two forces and the strategy is clear: price accurately at launch, capture peak attention, and convert it into competing offers. That is how homes sell quickly and at strong numbers. The alternative, pricing high, sitting through the attention window, then chasing the market down with reductions, is how sellers leave money on the table.

What Overpricing Actually Costs

Sellers often assume the worst case of overpricing is simple: reduce the price later if the home does not sell. That assumption is wrong. When a home sits past its initial attention window, buyers do not just stop showing up. They start to assume something is wrong with the property.

Days on market becomes a story buyers tell themselves about the home, and that story almost always lowers the final sales price. Every week your home sits on the market past its launch window costs you money.

It is not stubbornness. It is math. When we sit down together, I bring the full analysis: comps, market velocity, buyer-pool data, and a defensible price range with the reasoning behind every adjustment. You make the final call. My job is to make sure that call is informed by real data, not wishful thinking. This is why I will not overprice a listing to win it.

Five Reasons Homes Sell For Less

Most underperforming listings fail for the same handful of reasons, and every one is preventable. Even in a strong market, listings sit, reduce, and eventually sell for less than they should have, or do not sell at all. After studying hundreds of Big Island listings, I can tell you the causes rarely change.

They cluster around the same preventable failures, repeated by agents who either do not know better or are not willing to do the work.

Misguided Pricing

Some agents inflate the list price to win the listing, knowing the seller wants to hear a big number. Others let sellers price aspirationally and plan to reduce later. Both miss the in-market buyers writing offers right now. List prices only move down over time, and sellers who price high to come down later almost always net less than those who priced accurately from day one.

Lazy Photography

A meaningful share of Big Island listings, including multi-million-dollar properties, hit the market with phone photos or amateur work. This is the single most common reason qualified buyers do not schedule a showing. If the photos do not make a buyer want to see the home, nothing else in the marketing plan matters.

Inadequate Marketing

Posting to the MLS is not marketing. Real marketing means professional photography, twilight and aerial drone, video, 3D tours, a custom property website, paid digital advertising, social campaigns, print, and active outreach to the right buyer pool. Most agents do a fraction of this. The homes that sell quickly and at strong numbers are the ones where execution matches what the property is worth.

Restricted Showings

A home that is hard to show is a home that does not sell. Tight showing windows, slow responses to showing requests, or a seller who is not prepared all reduce the number of qualified buyers who get through the door. Fewer eyes mean fewer offers, and fewer offers mean less leverage.

Poor Negotiation

Once offers come in, the value of the agent shows up fast. Inexperienced agents miss leverage points, fail to investigate buyer motivations, give away credits unnecessarily, or accept the first reasonable offer instead of working toward the strongest one. Negotiation is part skill, part research, part discipline. The information advantage almost always wins.

Every one of these failures is preventable, and every one is something I systematically eliminate from my listings.

How I Market Your Home

Most agents on the Big Island post the listing to the MLS, check the syndication box so it appears on Zillow and Realtor.com, maybe boost a Facebook post, and call the home marketed. That is not marketing. That is a checklist. Real marketing is a campaign, built before the home ever hits the market and paid for entirely by me.

It starts with strategy: who is the buyer, where do they spend time, what convinces them to act. It moves into production: photography, video, 3D tours, written copy, design assets, all built to a standard the property deserves. It executes across channels: digital, print, social, email, paid advertising, direct outreach. And it measures performance so we can adjust in real time, not look back at the end and wonder what happened.

Marketing Aligned to Your Buyer

The buyer profile we identified earlier shapes every marketing decision that follows. A Kohala Coast luxury estate gets marketed differently than a Waikoloa condo, not just in tone but in channel selection, advertising spend, and visual direction. The buyer pool determines where the budget goes.

Production That Elevates the Property

Every listing gets professional photography, twilight and aerial drone, video walkthroughs, 3D tours, 2D floor plans, a custom property website, and printed collateral, all paid for by me. The quality of the assets is the quality of the impression buyers form. You only get one.

Reach That Matches the Audience

Production without reach is wasted budget. Marketing under the Compass platform extends your listing to the firm’s national agent network alongside broad MLS syndication, paid Google Ads with retargeting, social campaigns on Instagram, Facebook, and LinkedIn, email to my active buyer database and more than 1,600 Big Island agents, and targeted print to neighbors and adjacent buyer pools. Coverage is intentional, not assumed.

A campaign you do not pay for is a campaign that will not perform. I invest in your marketing because the return is what gets your home sold.

How I Prepare a Home Before It Goes Live

A well-prepared home does not just sell faster. It sells for more. The difference between a property that shows beautifully and one that does not is rarely structural. It is preparation. This is also where most sellers get overwhelmed, and it is where I take over: I treat pre-listing preparation as a coordinated production, not a series of errands you have to run.

My Role as Project Manager

Inspectors, contractors, painters, landscapers, stagers, photographers. Coordinating all of it from the mainland, or even from down the street, is genuinely time-consuming. Once we are working together, here is what I handle.

• I commission and pay for the pre-listing home inspection, up to $800, so we identify any issues before buyers do.
• I help coordinate repairs, refresh, and cleaning work using my vetted network of Big Island contractors, painters, handymen, and landscapers.
• I oversee staging consultation and execution, indoors and out.
• I help manage scheduling so the work gets done in the right sequence, on a timeline that is ready for professional photography and launch.
• I handle change-of-address and utility coordination when you are ready to transition.

You stay informed. I run the project. Most of my mainland sellers never set foot back on the island during the prep phase, and the home is photo-ready before we go live.

The Ten-Step Preparation Checklist

This is the sequence I work through on a Big Island listing, adjusted for the property.

1. Pre-listing inspection. Surfaces any issues a buyer’s inspector would flag, giving us time to address them on our terms instead of theirs. I cover this up to $800 as part of my listing service.
2. Repairs and updates. Address structural and mechanical issues identified in the inspection. Fix the small things buyers notice: leaky faucets, dated fixtures, scuffed paint. Modest updates in kitchens and bathrooms often return multiples of their cost.
3. Deep cleaning. Professional carpet, window, tile, and grout cleaning. Pressure-wash the exterior, driveway, and lanai. Address any pet or mildew odors before showings begin.
4. Landscaping and curb appeal. Trim trees and shrubs, especially anything blocking views or the home’s exterior lines. Refresh the lawn, planters, and entry. Repair fencing, gates, and outdoor structures.
5. Declutter and depersonalize. Remove personal photos and overly specific decor. Clear closets, garages, and storage areas. A short-term storage unit is often a worthwhile investment.
6. Staging. Furniture and decor arranged to highlight the home’s flow and best features. For Hawaii properties, the goal is a clean, tropical, lifestyle-aspirational look that connects with the buyer’s emotional reasons for being here.
7. Pest treatment. A professional treatment before listing addresses common Big Island concerns: termites, roaches, ants, geckos in screens. Repair any visible damage from prior infestations.
8. Energy and systems check. Confirm windows and doors seal properly. Verify A/C, ceiling fans, water heater, and major appliances are functioning. Inspect solar PV systems and organize system documents.
9. Showing readiness. Establish a plan for pets during showings. Ensure the property is safe and walkable, with no obvious hazards. Stock cleaning supplies and quick-touch items for pre-showing prep.
10. Maintenance through closing. Keep utilities on. Continue lawn care and routine maintenance. The home should look as good for the buyer’s final walkthrough as it did the day we listed.

The Production Assets Every Listing Gets

Buyers form an opinion of your home in the first three seconds. The overwhelming majority begin their search online, most of them scrolling on a phone and comparing your home to dozens of others in the same session. The photos, video, and tour assets on your listing are not supplementary material. They are the listing, until a buyer commits to seeing the home in person.

For mainland buyers, who make up the majority of my clients, the production assets often are the entire experience. They write offers based on what they have seen on screen. Every listing I take gets the full treatment, as much as the property allows. None of it is optional. None of it is at extra cost to you.

Professional Photography

A minimum of 30 high-resolution images by a professional real estate photographer who knows how to shoot Big Island homes. Wide-angle interiors, natural light, balanced exposure, and accurate color.

Twilight and Aerial Drone

The Big Island looks its best at golden hour, and aerial perspective is often what turns a property into a place. Twilight exteriors with interior lights glowing. Drone footage capturing the lot, the views, and the surrounding landscape.

HD Cinematic Video Tour

A guided video walkthrough that takes a buyer through the home the way they would experience it in person. Music, motion, lifestyle pacing. For mainland buyers, this is often the single most important asset they reference before writing an offer.

3D Zillow Showcase Tour

An immersive 3D walkthrough that lets buyers explore the home at their own pace, clicking into any room and moving through the layout naturally. Zillow reports that Showcase listings receive 75 percent more views, saves, and shares than comparable non-Showcase listings. More on Showcase below.

2D Floor Plan Renderings

Every buyer asks for a floor plan. Most Big Island listings do not have one. I generate accurate, digitally dimensioned 2D renderings so buyers can understand the layout, plan furniture, and orient themselves before they walk through.

Custom Listing Webpage

Your home gets its own dedicated website at a memorable URL, with all media, the full property description, MLS details, and an inquiry form. Branded for the property, not for me. Used across print, social, postcards, and email.

How Your Listing Reaches Buyers Online

Beautiful production assets only matter if buyers actually see them. Your buyers are spread across the mainland, Canada, Asia, and Europe, searching from phones and laptops, and increasingly through AI tools that filter listings before a buyer ever sees them. I have spent years building the digital infrastructure to reach them.

My Website

A live, custom-built platform rather than a templated lead page, with smart search, AI property matching, real-time MLS feeds, and hyper-local community data. Your listing gets featured placement, alongside the community pages and resources that bring buyers to the site in the first place.

MLS Syndication to 800 Plus Sites

Distribution to Zillow, Realtor.com, Redfin, and more than 800 national and international sites through ListHub, including Proxio, Juwai, and Immobel, reaching buyers in 19 languages.

Search and AI Optimization

I optimize for both traditional search and AI answer engines, so your listing surfaces when a buyer asks Google, ChatGPT, or another tool about Big Island properties. Most agents miss this entirely.

Targeted Google Ads and Retargeting

Paid campaigns aimed at buyers matched to your property and price point, with retargeting that follows engaged buyers across the web with ads featuring your home.

Email Reach to Buyers and Agents

Every new listing goes straight to my active buyer database and to more than 1,600 Big Island REALTORS®. The right buyer is often closer than the open market suggests.

Compass.com and Redfin

The most visited traditional brokerage website in the country, with 7.5 million monthly visitors, extended through the Compass partnership with Redfin and its 60 million active buyers. Compass publishes these as national platform figures.

What Zillow Showcase Adds

Zillow Showcase is a premium listing format available to a limited number of agents. Showcase listings receive priority placement in search results, dedicated email campaigns to interested buyers, immersive 3D and interactive media, distinct map markers that set them apart in the search grid, and feature placement on Apple Vision Pro.

Zillow publishes its own performance data for the format, drawn from transactions across the Showcase platform.

• 75 percent more views, saves, and shares compared to similar non-Showcase listings.
• More likely to go pending within 14 days than comparable non-Showcase listings nearby.
• An average of 2 percent more at sale.

Source: Zillow published Showcase performance data. National figures, not a projection for any individual property.

I include Zillow Showcase as a standard part of my listing service. No upcharge, no add-on, no decision for you to make about whether to invest in it. Every property I list gets the Showcase format, because the data shows it consistently produces stronger outcomes for my sellers. When buyers search Zillow for a property like yours, your listing will not look like the others.

Social, Print, and the Launch

Digital reach gets your listing seen. Social, print, and a strong launch turn attention into action. A great listing is not just visible, it builds momentum, and the first two weeks a property spends on the market are the most valuable marketing asset you have.

Social Media Promotion

Every listing receives a coordinated social campaign across the channels where Big Island buyers actually spend time.

• Featured posts on Instagram, Facebook, and LinkedIn through both my personal accounts and Compass platforms.
• A custom community blog post with embedded listing details, photography, and video, optimized for search and AI visibility.
• LinkedIn property features for relocation-driven and executive buyers.
• Social amplification for sustained reach over the listing period.

Print and Traditional Marketing

Digital does much of the work, but print still matters for the right buyer pool and the right property.

• Custom double-sided flyers on heavy stock, professionally designed and printed.
• Four-page property booklet brochures for select listings, suitable for showings and broker tours.
• Premium Compass signage with QR-coded sign riders linking directly to the property website.
• Targeted magazine remnant advertising for luxury properties where the placement makes sense.

Launch Execution

How a listing comes to market matters as much as how it is priced and produced.

• A coordinated rollout across digital and social channels, staggered for maximum first-week visibility.
• A launch-day email to my buyer database and more than 1,600 Big Island agents.
• Broker’s Caravan and a REALTOR® broker tour in the first week for local agent exposure.
• Bi-weekly traffic and exposure reports plus open house feedback summaries, so you always know how the campaign is performing.

Add this to the photography, video, 3D tours, custom website, digital reach, and Showcase positioning, and the picture becomes clear. Your home is not just listed. It is launched, surrounded, and supported with a campaign engineered to reach the right buyer in the shortest possible window.

What Happens From Listing to Closing

A Big Island sale moves through six phases, from a listing consultation roughly two to four weeks before launch through to funding a few days after closing. For most of my sellers, who do not live on-island during the listing, managing all of it from a thousand miles away is the biggest source of stress. You do not have to manage any of it. I do.

What follows is the actual sequence, and what your role is at each step. Your role is mostly to stay informed and make decisions. Mine is to run the process.

Phase 1: Strategy and Preparation

Roughly 2 to 4 weeks before going live, depending on the property and prep needs.

• Listing consultation and signed listing agreement
• Comparative market analysis and pricing strategy finalized
• Pre-listing inspection commissioned, covered by me up to $800
• Repair, refresh, cleaning, and staging coordinated through my vendor network
• Professional photography, twilight, drone, video, and 3D Showcase shoots scheduled
• Custom property website built and prepared for launch
• Disclosure package assembled and reviewed
• Launch date set, so every channel goes live together

Your role: review and approve the pricing strategy, sign disclosures, give vendors access as needed.

Phase 2: Going Live

Day of MLS launch and the first 14 days, the most concentrated marketing push of the entire listing.

• MLS listing goes active with the full media package
• Syndication pushes to 800 plus sites, including Zillow Showcase placement
• Email to my buyer database and more than 1,600 Big Island agents
• Coordinated launch across Instagram, Facebook, LinkedIn, and Google Ads
• Just Listed postcards mailed to 100 or more nearby neighbors
• Broker’s Caravan and REALTOR® broker tour scheduled
• Open houses, including a twilight option where appropriate
• Bi-weekly traffic and feedback reports begin

Your role: stay informed via the regular reports. I will flag anything that needs your input.

Phase 3: Offers and Negotiation

Begins as soon as offers come in, often within the first 2 to 4 weeks.

• Offers received, organized, and presented with clear summaries
• Buyer financial qualifications reviewed
• Buyer motivations and circumstances investigated to inform negotiation strategy
• Counteroffers, addendums, and final terms negotiated on your behalf
• Offer accepted and contract executed
• Buyer disclosure package delivered

Your role: make the final decision on which offer to accept and on key negotiation positions. I bring you the analysis and the recommendations.

Phase 4: Under Contract

Roughly 30 to 60 days, depending on financing and contingencies.

• Earnest money deposit confirmed and held in escrow
• Title report initiated and reviewed
• Buyer’s home inspection scheduled and attended
• Appraisal coordinated, and I personally meet appraisers at the property with comps and notes to support the value
• All disclosure deadlines tracked and managed
• Inspection negotiations, repairs and credits, handled on your behalf
• Contingencies removed in sequence as conditions are satisfied

Your role: respond to occasional decision points such as repair requests and credit negotiations. I handle scheduling, vendor coordination, and document flow.

Phase 5: Escrow and Closing Preparation

Final 7 to 14 days before closing.

• Final loan approval confirmed with the buyer’s lender
• Closing documents prepared by escrow
• HARPTA and FIRPTA documentation handled, if applicable
• 1031 exchange coordination, if applicable
• Final walk-through scheduled with the buyer
• Closing documents reviewed and signed, notarized remotely if needed
• Utility transfer and change-of-address coordinated

Your role: review and sign closing documents, often via mobile notary at your location.

Phase 6: Closing and Funding

Closing day and the days immediately after.

• All signed documents and funds transferred to escrow
• Documents recorded at the Bureau of Conveyances in Honolulu
• Existing mortgages paid off and remaining bills settled
• Net proceeds wired to your account
• Keys and access transferred to the new owner
• Final closing statement and tax documents delivered for your records

Your role: confirm wire instructions, and celebrate.

How Compass One Keeps You Informed

Compass One is a client dashboard that connects you and your agent through every phase of the transaction, with 24/7 visibility before, during, and after the sale. Throughout all six phases it is one secure place to follow the sale in real time, which matters most when you are managing the whole thing from another time zone.

• Collaborate with ease. Communicate with me in one shared space, so the process stays transparent from start to finish.
• Keep up to date. View your timeline for an overview of upcoming steps, recent updates, and pending tasks.
• Know your team. Contact information for everyone involved, including your agent team, loan officer, and closing partners.
• Stay organized. Reference your signed documents, forms, and other paperwork from one place.
• Gain insights. Monitor the market and track your listing traffic and engagement metrics to inform data-backed decisions.
• Follow from anywhere. See the sale from the mainland or abroad, on any device, with the same view of the transaction that I have.

Ask me to set up your Compass One account when we start working together.

How the Hawaii Escrow Process Works

Once your home is under contract, the transaction enters escrow. An escrow company is a confidential, impartial third party that holds funds and documents in safekeeping until every condition of the purchase contract is satisfied. They represent neither you nor the buyer. Their job is to make sure the transaction closes correctly.

For mainland sellers especially, this is where the process can feel opaque, because Hawaii’s escrow system works differently than what you may be used to from prior transactions. You do not need to learn the mechanics. You just need to know what is happening, when, and what is expected of you.

When Escrow Opens

In Hawaii, escrow opens the moment the purchase contract is signed by both parties. The buyer’s earnest money deposit is wired to the escrow company within a few days of contract execution. From there, escrow tracks every milestone in the contract through to recordation.

Typical Timeline: 30 to 60 Days

Most Big Island escrows run 30 to 60 days, depending on whether the buyer is paying cash or financing. Cash transactions can close faster, sometimes in 2 to 3 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 What They Mean for You

A purchase contract includes contingencies, the conditions the buyer must satisfy or waive before they are obligated to close. The most common are home inspection, financing approval, title review, appraisal, seller’s disclosure review, and, for condos, HOA document review.

If the buyer cancels within their contingency periods for a covered reason, they can typically recover their earnest money deposit. Once contingencies are removed, the buyer is fully committed and the deposit is at risk if they walk. I track every contingency deadline. You do not need to.

Inspection and Repair Negotiations

After the buyer’s home inspection, they may request repairs or credits. As the seller, you are not automatically obligated to do anything. We negotiate from a position of information: which items are reasonable, which are not, and what makes sense given the contract terms and the buyer’s leverage. This is usually the second negotiation of the transaction, after the original offer. Handled well, it protects your proceeds. Handled poorly, it can erode them quickly.

Closing and Recordation

About a week before closing, escrow prepares the closing documents, including the deed, for signing. You sign separately from the buyer. Rarely are both parties in the same room, especially on the Big Island. 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 final funds 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. Escrow then pays off any existing mortgages, settles outstanding bills, and wires your net proceeds to the account you designate. The buyer receives the keys. You receive the funds.

Why a Cooperating Broker Helps Your Sale

Working with a professional buyer’s agent provides benefits sellers often have not considered. In partnership with a buyer’s agent, I can show your home in its best light to a widened pool of qualified buyers and secure a more efficient contract-to-close process for everyone involved.

• Increased exposure for your listing. More eyes means more interest. A buyer’s agent can get your listing in front of buyers they are currently representing, which maximizes your home’s exposure in a competitive market.
• More qualified buyers. Working with a buyer’s agent increases the likelihood your home will be seen by qualified, vetted buyers who are educated about the market and ready to transact.
• Seamless contract-to-close. Buyer agents provide guidance and support to buyers through the contract-to-close process to troubleshoot and resolve potential issues. Dedicated agents on both sides ensures an objective approach and increases the likelihood of a smooth transaction.
• Reduced liability and exposure. Professional representation more readily ensures the buyer completes their investigations to their satisfaction, thoroughly reviews and understands seller disclosures, and completes each required step. The result is a well-informed client without buyer’s remorse.

Seller acknowledges and understands that (i) commissions are negotiable, (ii) Seller is not required to offer compensation to a Cooperating Broker, and (iii) any offer of compensation is at the discretion of the Seller.

What Offering Buyer Agent Compensation Does

In the United States, real estate commissions can be paid by the seller, the listing agent, or the buyer. Continuing the practice of offering buyer compensation by the seller or listing agent increases the likelihood of having a professional buyer’s agent on the other side of the transaction, and provides a number of advantages.

• Increase interest from qualified buyers. Offering compensation to the buyer’s agent can make your property more attractive to serious buyers and more accessible to a wider pool, some of whom have limited cash for upfront costs.
• Secure a higher purchase price. If buyers do not need to reserve funds to pay their own agent, those funds stay available for the purchase price, which can raise what they are able to offer on your home.
• Sell faster. Removing that financial burden from the buyer side widens the field of buyers who can transact immediately, which can reduce the time your property spends on the market.
• Simplify negotiations. With compensation settled up front, negotiations stay focused on price and terms rather than on who pays whom, which keeps the conversation cleaner and moving.

Seller acknowledges and understands that (i) commissions are negotiable, (ii) Seller is not required to offer compensation to a Cooperating Broker, and (iii) any offer of compensation is at the discretion of the Seller.

Selling a Big Island Income Property

When your home is also a business, it has to be sold like one. A primary residence sells on lifestyle. An income property sells on lifestyle and return. The buyers for these properties, most of them on the mainland, are underwriting a purchase, not just falling for a view. The listing has to answer both.

Many of my sellers own a vacation home they have rented part of the year or a property run as a full short-term rental. Selling one is a different transaction than selling a home someone lives in, and the difference shows up in the final price. A rental with clean, transferable income sells to a wider pool, faster, and for more.

The Income Story

Documented revenue, occupancy, and average nightly rate turn an emotional purchase into a confident one. I assemble a clear, accurate performance summary that widens your buyer pool to include investors who would otherwise scroll right past.

Permitted Standing

On the Big Island, a property’s legal short-term rental status directly affects its value and how many buyers can act on it. I confirm your standing is documented and transferable up front, before a buyer’s questions become a renegotiation.

Marketing to Investors

Most agents market every listing the same way. An income property needs financial storytelling alongside the visuals, placed where investor buyers actually search. That is how a rental reaches the full pool and sells for what it is truly worth.

Showings While Booked

Your property can stay on the rental calendar while it is listed. I coordinate photography and showings around active reservations, working with your cleaners and manager so guests are never disrupted and you keep earning while the home sells.

Timing the Calendar

Existing bookings are an asset, not an obstacle. We position the sale around your reservation calendar and decide early how assumed bookings transfer to the buyer, so revenue keeps flowing and the transaction stays clean from contract to close.

Turnkey Conveyance

Investor buyers expect to keep earning the day they close. Furnishings, systems, and trusted vendor relationships are part of the value here, not an afterthought. I help you present the property as the turnkey operation it already is.

HARPTA and FIRPTA for Non-Resident Sellers

If you are a Hawaii non-resident selling Big Island property, you are subject to one or both of these withholding rules at closing. HARPTA withholds 7.25 percent of the gross sales price for the State of Hawaii. FIRPTA withholds 15 percent for the IRS when the seller is a foreign person. Both are withholdings, not final taxes.

They exist to ensure the state and federal governments collect the taxes owed on any gain from the sale, but the way they are structured can catch sellers off guard if they are not planned for in advance.

HARPTA: Hawaii Real Property Tax Act

Applies to any seller who is not a Hawaii resident, regardless of citizenship. At closing, escrow withholds 7.25 percent of the gross sales price, the full sales price rather than the gain, and remits it to the State of Hawaii Department of Taxation.

This is a withholding, not a tax. The actual tax owed depends on your gain and your overall tax situation, and any over-withheld amount is refundable when you file your Hawaii non-resident tax return for the year. For most non-resident sellers, the actual tax owed is significantly less than 7.25 percent of the sale price, which means a substantial refund is typically due once the return is filed.

FIRPTA: Foreign Investment in Real Property Tax Act

Applies to foreign persons or entities, meaning non-U.S. citizens and non-resident aliens, selling U.S. real property. At closing, escrow withholds 15 percent of the gross sales price and remits it to the IRS.

As with HARPTA, this is a withholding rather than a final tax. The actual tax owed is based on the gain, and over-withheld amounts are recoverable through a U.S. tax return or by applying for a withholding certificate in advance. If you are subject to both HARPTA and FIRPTA, both withholdings apply at closing.

How Sellers Can Minimize the Impact

Several strategies may help reduce, defer, or eliminate the withholding altogether. The right path depends on your specific situation, and I always recommend coordinating with a Hawaii-licensed tax professional or 1031 specialist alongside the listing process.

• Withholding certificates. Apply to the State of Hawaii or the IRS in advance to reduce or waive withholding when the actual tax owed is demonstrably lower than the standard amount. Done correctly and filed on time, this can release significant funds at closing rather than tying them up for months waiting on a refund.
• 1031 tax-deferred exchange. If you are reinvesting the proceeds into another investment property, a properly structured 1031 exchange can defer both the capital gains tax and the HARPTA and FIRPTA withholding entirely.
• Primary residence exclusion. If the property qualifies as your primary residence under IRS rules, you may be able to exclude up to $250,000 of gain if single, or $500,000 if married filing jointly, from federal taxation, with potential reductions in withholding as a result.
• Timely filing and documentation. For sellers who do not qualify for advance reduction, filing your non-resident tax return promptly after closing accelerates any refund due.

These rules sound complicated. In practice, they are routine. I have coordinated dozens of HARPTA and FIRPTA transactions, and I work with experienced Hawaii tax professionals and 1031 specialists who handle the technical filings. You will know what to expect well before closing.

Tax laws are complex and individual situations vary. The information here is general guidance, not tax advice. Always consult a Hawaii-licensed tax professional for advice specific to your situation.

How a 1031 Exchange Defers Capital Gains

A 1031 exchange lets you sell a qualifying investment property and reinvest the proceeds into another like-kind property without immediately recognizing the capital gains tax. Named for Section 1031 of the Internal Revenue Code, the taxes are deferred, often indefinitely, as long as you keep exchanging into qualifying properties over time.

For Big Island sellers in particular, this is a significant strategy. The island has appreciated substantially over the last decade, and many of my clients are sitting on properties they bought years ago at a fraction of today’s value. Without a 1031 exchange, the capital gains tax bill on a sale can be staggering. With one, that capital stays working for you.

The Process, Simplified

A 1031 exchange has strict timelines and requirements. Miss a deadline or fail to follow the rules, and the entire exchange fails, meaning the full capital gains tax becomes due immediately.

1. Plan before you list. The exchange must be set up before your sale closes. We coordinate with a Qualified Intermediary, a third party who holds the proceeds during the exchange. You cannot take direct receipt of the funds at any point, or the exchange is disqualified.
2. Sell your property. Your Big Island property sells through the normal listing and escrow process. Proceeds go directly from escrow to the Qualified Intermediary, not to you.
3. Identify the replacement property. You have 45 days from closing to formally identify up to three potential replacement properties, or more under specific rules. This deadline is strict.
4. Acquire the replacement property. You have 180 days from closing to complete the purchase. The replacement property must be of equal or greater value to fully defer the gain. This deadline is also strict.

Why Sellers Use a 1031

• Capital gains tax deferral. Defer federal capital gains tax, Hawaii state capital gains tax, depreciation recapture, and net investment income tax. On a property with significant appreciation, the deferred tax can easily exceed six figures. That capital stays invested in the new property rather than going to the IRS.
• Portfolio repositioning. Exchange out of a property that no longer fits your goals, such as a high-maintenance vacation rental, a distant location, or an aging asset, and into one that does. A 1031 lets you upgrade or restructure your portfolio without a tax penalty.
• Generational wealth strategy. Continue exchanging through your lifetime, and when the property eventually passes to your heirs, they receive a stepped-up cost basis, potentially eliminating the deferred tax entirely.

How I Support 1031 Exchanges

Most agents have heard of 1031 exchanges. Far fewer have actually executed them with clients. I have, and the experience matters, because the timing of the listing, the structure of the contract, the coordination with the Qualified Intermediary, and the identification of replacement properties all need to align precisely.

• I help you evaluate whether a 1031 is the right strategy for your situation, and connect you with experienced Qualified Intermediaries and Hawaii-licensed tax professionals.
• I structure the listing timeline to give you the best possible window for identifying and acquiring a replacement property.
• I coordinate directly with the Qualified Intermediary throughout escrow to ensure the funds flow correctly.
• If you are exchanging into another Big Island property, I help you identify and acquire it. If you are exchanging into mainland or other markets, I connect you with trusted agents through the Compass national network.

1031 exchanges are subject to strict IRS rules and timelines. Always work with a Qualified Intermediary and a Hawaii-licensed tax professional to structure your exchange correctly. The information here is general guidance, not tax advice.

Five Reasons Sellers Choose Me

I have had hundreds of conversations with sellers about why they ultimately chose to work with me over another agent. The reasons are consistent, and they reflect what actually matters in this work rather than what an agent’s marketing tries to claim. 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 price, marketability, and buyer behavior in a Waikoloa condo versus a Kohala Coast estate are not theoretical to me.

Finance-Backed Pricing

A degree in finance and more than 20 years of executive sales and marketing experience changed how I approach the analytical side of this work. I bring a level of rigor most agents do not: comparative market analysis with documented adjustments, market velocity data, buyer-pool analysis, and a defensible price range you can actually follow.

Marketing as a Discipline

Before real estate, I spent two decades in executive sales and marketing for respected West Hawaii companies. That background is the reason my listings get professional photography, twilight and aerial drone, video, 3D Showcase tours, custom property websites, paid digital advertising, and social campaigns. All paid for by me, all executed personally, all measured and adjusted. Marketing is not a feature of my service. It is how my career has worked for decades.

Honesty That Holds Up

Real estate is full of agents who tell sellers what they want to hear to win the listing, then fail to deliver. 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 the truth about your property, your pricing, and the market. My clients consistently say the honesty is what made them comfortable signing with me.

Work Ethic That Shows Up

The most common reason sellers leave their first agent and come to me is responsiveness. Calls returned within the hour. Texts answered the same day. Showings personally attended. Open houses personally hosted. Bi-weekly reports throughout the listing. Final walkthroughs personally walked. None of this is exceptional. It is just doing the job at the standard the work deserves.

When you list 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 listing.

Selling at the Big Island Luxury Level

Selling at the luxury level requires the credentials, the network, the discretion, and the experience to represent properties and clients at this scale. My clients include high-net-worth individuals, executives, real estate collectors, and families building generational wealth. They expect service that matches the value of the asset.

The Certified Luxury Home Marketing Specialist designation, at its highest Guild Elite tier, is awarded to agents with demonstrated performance in the luxury market. It is my personal credential, earned representing high-value Big Island property, and it signals real expertise serving affluent buyers and sellers.

Communities I Represent

Kailua-Kona, Holualoa, and Keauhou, the Kohala Coast resort communities, Waikoloa, and Waimea, along with the island’s ultra-luxury private enclaves: Hualalai, Kukio, Kohanaiki, Hokuliʻa, Mauna Lani, and Mauna Kea.

For listings at the Big Island’s luxury tier, generally $3.2M and above, your home also qualifies for the Compass Luxury platform, a dedicated marketing layer built for affluent and international buyers. You can see the current market in luxury homes and luxury condos across the island.

At this level, the difference is not just marketing. It is judgment, discretion, and a track record of results, brought to every luxury listing I represent.

What the Compass Luxury Platform Adds

For your most valuable Big Island properties, the standard campaign is only the beginning. Listings at $3.2M and above in West Hawaii qualify for the Compass Luxury platform, a dedicated suite built to put a property in front of affluent and international buyers through channels an independent brokerage cannot match.

This is a platform layer that sits on top of everything else in this guide: the production, the digital reach, and the coordinated launch, reserved for the top of the market. These channels run alongside my hands-on service, not in place of it. I manage the strategy, the assets, and the relationships.

• Wealth mapping. Access to a Compass database of more than 157,000 high-net-worth individuals, each with a minimum net worth of $5 million, across 193 countries. The targeting is built around your property, not guesswork.
• Luxury website. Placement on luxuryatcompass.com, the dedicated Compass luxury site. Qualifying listings may be featured through homepage spotlights, video and press features, and inclusion in a luxury Lifestyle Collection.
• Luxury newsletters. Feature in a Compass Luxury newsletter reaching more than 35,000 ultra-high-net-worth consumers and leading brokers around the world.
• Curated magazine. Visibility within Curated, the Compass print and digital publication, reaching an audience of more than 70,000 ultra-high-net-worth consumers and leading brokers.
• Instagram and YouTube. Featured on the main Compass Instagram account and its audience of 189,000 followers, with video added to the Compass Luxury YouTube playlist and its 13,000 subscribers.
• Luxury agent network. One-click promotion to thousands of Compass luxury agents nationwide. Compass is not franchised, which lets me work directly with the top luxury agents in every major market.

Compass Luxury platform figures are published by Compass and are national. Availability of individual channels depends on the property and on Compass qualification at the time of listing.

Global Reach

The buyer for a multi-million-dollar Big Island estate is rarely local. They are in California, the Pacific Northwest, and Texas, and in the financial centers of Asia, Canada, and Europe. Reaching them takes a platform with genuine international distribution, not a local listing pushed to the usual national portals.

• International distribution. Featured across 96 international portals in more than 50 countries, and on the native Compass Chinese-language website and social platforms, reaching more than 38,000 affluent Chinese followers actively tracking US real estate.
• Wealth-mapped global targeting. The same wealth mapping that identifies likely buyers at home extends worldwide, focusing your property’s marketing on affluent audiences in the regions where Big Island demand actually originates.
• BARNES International Realty. Compass has established a program with BARNES to showcase listings to their international network of ultra-high-net-worth consumers and leading brokers. BARNES is present in more than 75 destinations, with 130 offices across 20 countries, 1,300 luxury agents, and 150,000 international clients.

How Luxury Marketing Works in Practice

The Compass Luxury platform is not theory. It is a set of capabilities I deploy in deliberate ways depending on the property, the buyer, and the goal. No two luxury properties are marketed the same way. My job is knowing which tools a given property needs, and executing them with the discretion the luxury level demands.

Pitch Support

For ultra-luxury communities such as Kohanaiki or Hualalai, I use wealth mapping to define the buyer pool before the home ever comes to market: where the likely buyers live, what they already own, and what draws them to the Big Island. Those insights shape how the property is positioned from day one.

Listing Strategy

For a signature property, I build a curated visual narrative, a single cohesive story told through photography, design, and copy, and deliver it to a targeted list of affluent buyers and their agents through luxury print pieces and direct outreach. The property arrives as an experience, not a listing.

Custom Design

A large oceanfront or upcountry estate can warrant a design system of its own. Marketing materials drawn from the property’s setting, the lava and water of the Kohala Coast, the pasture and elevation of Waimea, so every touchpoint reflects the specific place rather than a template.

Discretion

At this level, privacy is often part of the brief. Showings by appointment and prequalification only, no public open houses unless you want them, and controlled release of address and interior imagery. Your home gets marketed fully. Your household does not.

Events and PR

For an architecturally significant property, a curated launch event paired with placement in luxury publications can turn a listing into an occasion, drawing the right buyers, brokers, and attention to the home.

My Commitment to This Community

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. That commitment matters in this work.

Sellers I represent are usually entrusting me with one of their most significant assets, and most of them never meet me in person before signing the listing agreement. They want to know who they are working with. They want to know I am here for the long haul. And they want to know I treat this island as a home, not just a market.

The Jingle Bell Beach Run

In December 2005, my wife 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. It is one of many events on the island’s running calendar.

City SC Hawaii

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 of our 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. Below are a few of the people who have trusted me with their Big Island sale or purchase, in their words. More are on my reviews page.

Penn handled everything perfectly from start to finish. From my very first minute of reaching out to inquire about selling my condo, to the final day of closing, Penn was on top of everything. He scheduled meetings, took care of communication between all parties, and handled all of the details promptly and professionally. I have a background in real estate, and can honestly say Penn was as good as they get.

Jeni Winegarner
Sold her Aliʻi Cove condo in Kona

Talk about going the extra mile. Penn’s most recent transaction required a ton of research, but in the end that research presented an incredible opportunity, to the tune of hundreds of thousands of dollars in instant equity, for his client. All 900 West Hawaii agents in this market saw this property and saw the red flags, but Penn was the only one to do the work and see those red flags weren’t really there. Truly an amazing job.

Mike Drutar
Principal Broker

I am a mortgage lender so I work with a lot of REALTORS® in Hawaii. Penn is one of the absolute best on the Big Island. He truly cares about people. He’s very detailed and writes excellent strategic offers. His marketing materials are extremely professional. He has built amazing tools into his website. And he has a very good handle on the market and watches new listings diligently with his clients in mind. Realtors are NOT created equal. If you want someone who will work hard to get you the best deal possible and who really cares about you, pick Penn. You won’t be disappointed.

April Nelson
Mortgage lender and client, Kainaliu condo

I’m so lucky and grateful to have found Penn when it came time to sell my elderly mother’s home in Kona Paradise. I was sure I’d have to travel from California, but Penn handled everything there. He got the best buyer and price for the house and the whole process went smoothly.

Lindsey Jennings
Sold her Kona Paradise home

Penn helped sell our home in Iolani. He was extremely detail-oriented and knew everything that was going on in the market. He was on top of scheduling showings and open houses. He was always communicating with us and there were never any surprises. He was always professional and kept us informed 100% through the entire process. He did a great job and we’d recommend him to anyone buying or selling on the Big Island.

Steve and Jennifer Spelshaus
Sold their Iolani Estates home in Kona

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 wasn’t 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’s deeply rooted in the community, and now I admire him too.

SJ Lee
Holualoa 5-acre estate, buyer and seller client

Penn provided incredible service in our quest to find the perfect waterfront condo in Kona. He 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. Outstanding service every step of the way.

Pat and Pam Kemp
Kona oceanfront condo, buyer and seller clients

Penn was amazing. He knew exactly what we were looking for and helped us find the perfect condo. He was remarkably responsive, professional, and fun to work with. You simply won’t find a better Realtor. Penn deserves my highest recommendation.

Steve Weiss
Oceanfront condo and investment property, Kailua-Kona

We just moved in to 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 didn’t think a home was right for us. I would unconditionally recommend Penn to anyone looking for something special in Kona.

Jeff Jensen
Keauhou Estates, buyers

I am so thankful for honest, hardworking people in our community. Penn is one of them. When it comes to the home-buying process, he helps every step of the way and has patience for the many, many questions. Thank you, Penn, for making the process that much easier.

Bree Wee
Kona condo, first-time buyer

Hawaii Real Estate Terms You Will Hear

These are the terms that come up most often in a Big Island sale. A few of them, HARPTA, the Bureau of Conveyances, and fee simple versus leasehold, work differently here than they do on the mainland, and those are the ones worth reading twice.

• Appraisal. Assessment of the property’s market value, for the purpose of obtaining a mortgage and performed by a licensed appraiser.
• Assessed value. Value placed upon property for property tax purposes by the Tax Collector.
• Closing costs. Expenses incidental to a sale of real estate, such as loan fees, appraisal fees, title insurance and escrow fees.
• Closing statement. The statement listing the financial settlement between buyer and seller, and the costs each must pay.
• Contingency. Certain criteria that have to be met in order to finalize the sale.
• Conventional mortgage. A mortgage not obtained under a government-insured program such as FHA or VA.
• Credit. Money given to a buyer from a seller through escrow at closing.
• HARPTA. Hawaii Real Property Tax Act. Requires escrow to withhold a percentage of the gross sales price from non-resident sellers and remit it to the State of Hawaii. A withholding, not a tax.
• FIRPTA. Foreign Investment in Real Property Tax Act. The federal equivalent, applying to foreign persons and entities selling U.S. real property.
• 1031 exchange. A transaction under Section 1031 of the Internal Revenue Code that defers capital gains tax when sale proceeds are reinvested in a like-kind property within strict deadlines.
• Escrow. A neutral third party that handles the transfer of any money during the sale of a home from initial deposit to final funding and closing.
• Earnest money deposit. A deposit made by the buyer at contract signing and held by escrow to demonstrate good faith. The amount is negotiated in the purchase contract, and it is generally refundable if a contingency cannot be met within its deadline.
• Fixed rate mortgage. A loan on which the interest rate and monthly payment do not change.
• Home warranty. A policy that covers certain repairs, such as plumbing and electrical, of a newly purchased home for a period of time, typically one year.
• Preliminary title report. A report showing the condition of title before a sale or loan transaction. After completion of the transaction, a new title insurance policy will be issued.
• Title insurance. Insurance to protect the buyer and lender against losses arising from disputes over the ownership of a property.
• Recording fees. Money paid for recording a home sale with the local authorities, thereby making it part of the public records.
• Bureau of Conveyances. The State of Hawaii office in Honolulu where deeds and other real property documents are recorded. Recordation there is the moment a Hawaii sale closes.
• Fee simple and leasehold. Fee simple conveys ownership of both the improvements and the land. Leasehold conveys the improvements and the right to use the land for a fixed term.

Questions to Ask Any Agent, Including Me

Most sellers do not interview their agents the way they should. They go with someone a friend recommended, someone they saw on a sign, or someone whose face they recognized from a postcard. The decision is often made before any real questions are asked, and that approach can cost you. Below are the questions I would ask any agent I was thinking of hiring, with my own answers.

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

I have lived on the Big Island full-time for over 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, Guild Elite tier), PSA (Pricing Strategy Advisor), e-PRO (digital marketing), RSPS (Resort and Second Home Property Specialist), and At Home With Diversity. I am also a REALM member, an invitation-only network representing the top 0.5 percent of luxury agents worldwide.

How Do You Approach Pricing Strategy

With rigor. Every listing starts with a comparative market analysis using documented adjustments, layered with current market velocity, absorption-rate data, and buyer-pool analysis at relevant price tiers. I will show you the math behind any price I recommend, and you will have everything you need to make an informed decision.

What Is Your Marketing Plan

A complete marketing campaign, all paid for by me: professional photography, twilight and aerial drone, video walkthroughs, 3D Zillow Showcase tours, custom property websites, MLS syndication to 800 plus sites, paid Google Ads with retargeting, social campaigns across Instagram, Facebook, and LinkedIn, print collateral, Just Listed mailers, and broker tour outreach. Detailed throughout this guide.

Can You Provide Client References

Yes. I will connect you directly with past sellers, lenders, and title officers I have worked with. Several testimonials are included in this guide, with many more on my reviews page. I encourage you to call them.

What Percentage of Your Business Comes From Referrals

Roughly 20 percent. The rest comes from my marketing engine: website, search visibility, paid digital, and sustained outreach. That distribution matters because it means I am active in the market every day, not just when referrals happen to come in. You want an agent whose business runs whether or not their network is feeding them deals.

How Do You Communicate With Sellers During the Listing

Direct and frequently. Phone, text, or email, whichever you prefer. Bi-weekly traffic and feedback reports throughout the listing period. Real-time updates on showings, offers, and market movement. The most common reason sellers leave their first agent and come to me is responsiveness, and I take that seriously.

Do You Discount Your Fees to Win Listings

No, and I would encourage you to be cautious of agents who do. Discounted commissions usually correlate with discounted service: less marketing investment, less personal attention, and less leverage at the negotiation table. I would rather lose a listing than win one I cannot deliver on. That said, every situation is different, and I build a custom service plan for every client.

What Is Your Guarantee

If at any point during our listing agreement you are not satisfied with my service, you are free to part ways with me. No questions, no hard feelings. I would rather earn your business every day than hold you to a contract you no longer want.

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.

Reach out by phone, text, or email. I respond quickly, and I would be honored to hear about your home.

With aloha,

Penn Henderson, R(S)
REALTOR®, Hawaii License RS-83962
penn@pennhenderson.com
808.345.6214
Compass, 75-1029 Henry St., Suite 301, Kailua-Kona, HI 96740

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This guide is original work by Penn Henderson, R(S). Linking to it and short attributed quotations are welcome. Republishing it, or rewriting it for another agent or brokerage website, is not permitted. Market figures are sourced from Hawaii Information Service and compiled by Penn Henderson, R(S). Compass and Zillow platform figures are published by those companies and are national. Nothing here is tax or legal advice.