Penn Henderson Real Estate Agent - COMPASS

Penn Henderson buyer's agent for 62-268 Kamahoi Place Unit 2, Kamuela, HI - sold for $6,700,000 — Sold $6,700,000

75-5681 Kuakini Hwy Unit 303, Kailua Kona, HI For Sale $499,000 - listed by Penn Henderson — For Sale $499,000

Penn Henderson listing agent for 75-5545 Hahai St, Holualoa, HI - sold for $1,600,000 — Sold $1,600,000

73-1157 Ala Kapua St, Kailua Kona, HI Under Contract $997,500 - listed by Penn Henderson — Under Contract $997,500

Penn Henderson buyer's agent for 78-7070 Alii Dr Unit C202, Kailua Kona, HI - sold for $660,000 — Sold $660,000

Penn Henderson

Kailua Kona HI

COMPASS

56 Closed Sales

$66.1M Total Value

$15K - $8.2M Price Range

$1.2M Average Price

Prior 5 years

About Penn

Aloha. I am Penn Henderson, a REALTOR® with Compass in Kona on Hawaii's Big Island, license RS-83962.

I have lived in Kona since 2001 and have been a full-time REALTOR® since 2021. I specialize in luxury, oceanfront, vacation, and investment property across West Hawaii, from Kailua-Kona, Holualoa, and Keauhou to Waikoloa, Waimea, and the Kohala Coast resort communities, including Hualalai, Kukio, Kohanaiki, Hokulia, Mauna Lani, and Mauna Kea.

Most of the people I represent are buying or selling from thousands of miles away. That shapes how I work: professional photography, video, and 3D tours on every listing; regular reporting; and a straight answer when a property isn't right for you.

Hawaii Information Service MLS data ranks me in the top 3 percent of Big Island agents, with more than $20M in annual sales. My clients rate me 5.0 across more than 40 Google reviews, which is how I judge an agent.

My certifications include CLHMS (Guild Elite tier), PSA, RSPS, AHWD, and e-PRO, and I am a REALM member.

808.345.6214 | penn@pennhenderson.com | pennhenderson.com

Home Types: House, Condo, Lot/Land, Townhouse

Years of Experience: 5

Education: University of Colorado at Boulder, and Vail Mountain School

Transaction History

1 Year
2 Year
5 Year

Seller Deals
Total Deals	5
Total Value	$4,655,000
Average Sale Price	$931,000
Price Range	$75K - $1.6M

Buyer Deals
Total Deals	9
Total Value	$10,435,000
Average Sale Price	$1,159,444
Price Range	$390K - $2.4M

1 Year View by Quarter

Seller Deals
Total Deals	9
Total Value	$6,974,500
Average Sale Price	$774,944
Price Range	$75K - $1.6M

Buyer Deals
Total Deals	15
Total Value	$21,969,900
Average Sale Price	$1,464,660
Price Range	$390K - $6.7M

Seller Deals
Total Deals	17
Total Value	$17,483,450
Average Sale Price	$1,028,438
Price Range	$75K - $5.1M

Buyer Deals
Total Deals	39
Total Value	$48,637,400
Average Sale Price	$1,247,113
Price Range	$15K - $8.2M

5 Year View

Areas Penn is Experienced In

Kailua Kona

38 Sales
Waikoloa

5 Sales
Kailua

5 Sales
Kamuela

4 Sales

Penn's Listings and Deals

Penn's Active Listings

$499,000
- 1 Bed
- 1 Bath
- 753 Sq Ft
75-5681 Kuakini Hwy

Unit 303

Kailua Kona, HI
Kalanikai 303 offers a rare combination of ocean proximity, thoughtful renovation, established short-term rental income, and a highly walkable location in Kailua-Kona. Set on the top floor of a concrete building surrounded by mature tropical landscaping, this 753-square-foot, one-bedroom, one-bath residence is positioned to capture natural light, cooling trade winds, and views across Kona town to

Penn Henderson COMPASS

$3,499,000
- 4 Beds
- 3 Baths
- 2,533 Sq Ft
74-4711 Kaianiani Place

Kailua-Kona, HI
Set on a full acre at ~1,200 feet of comfortable elevation, this new-build Island Contemporary captures panoramic ocean and sunset views of the Kona Coast. *With an estimated completion date of January 1, 2027, buyers purchasing during construction can personalize certain finishes, paint colors, and landscaping before move-in.The 2,533-square-foot single-level floor plan offers four

Penn Henderson COMPASS

$490,000
- Land
- 1.39 Acres
- $352,518 per Acre
81-460 Keehau St

Kealakekua, HI
E Komo Mai to Hokuli‘a Lot #123 — South Kona Living at Its Finest! Situated within the luxury private golf community of Hokuli‘a along the famed Kona Coast, Lot #123 offers an exceptional opportunity to build your dream home on a rare 1.4-acre corner parcel. This prime homesite is gently sloped makai, predominantly level, and generally FREE OF TOPSOIL ENCUMBRANCES, with nearly 100% usable land,

Penn Henderson COMPASS

$499,000
- 1 Bed
- 1 Bath
- 736 Sq Ft
75-6082 Alii Dr

Unit A308

Kailua Kona, HI
Welcome to Casa De Emdeko A308, where island living meets everyday comfort. This beautifully updated 1-bedroom, 1-bath condominium along Kailua-Kona’s iconic Aliʻi Drive delivers the perfect mix of modern design, relaxed tropical vibes, and oceanfront appeal.Step inside to find a bright, open floor plan filled with natural light. The contemporary kitchen shines with new appliances,

Penn Henderson COMPASS

$1,020,000
- 2 Beds
- 2 Baths
- 806 Sq Ft
76-6246 Alii Dr

Unit 411

Kailua Kona, HI
Oceanfront Alii Drive • Top-floor 2 bed 2 bath • Panoramic ocean and sunset views • 176 sq ft private lanai • Elevator building • 2 parking stalls • STVR permit Top-floor living meets oceanfront setting at Kona Bali Kai on Historic Alii Drive, where this 2-bedroom, two full bath condominium offers 806 sq ft of interior space plus a 176 sq ft private lanai. Located in Kailua-Kona, Kona Bali Kai

Penn Henderson COMPASS

$997,500

Under Contract
- 2 Beds
- 3 Baths
- 1,548 Sq Ft
73-1157 Ala Kapua St

Kailua Kona, HI
Beautiful two-bedroom home, plus a huge garden-level separate living space with private entrance! Located within Kona Palisades on a manicured 11,487 sq ft lot, this two-story home has been steadily improved by owners who clearly love it. Peek-a-boo ocean horizon and sunset views, mature tropical landscaping, and two separate living areas make it a rare value in North Kona.The main level

Penn Henderson COMPASS

$2,995,000

Under Contract
- 3 Beds
- 3.5 Baths
- 2,632 Sq Ft
72-4071 Akahipuu Place

Kailua Kona, HI
Set at the end of a private cul-de-sac in gated Makalei Estates, this single-level 3-bedroom, 3.5-bath residence with a dedicated office rests on 3.13 fully fenced acres transformed into a private garden estate. Terraced lawns, handcrafted rock walls, tropical landscaping, and elevated gathering spaces unfold across the property, all oriented toward the North Kona coastline and

Penn Henderson COMPASS

Recently Sold

$1,600,000

Sold Apr 23, 2026
- 3 Beds
- 2 Baths
- 1,934 Sq Ft
75-5545 Hahai St

Holualoa, HI
- 2% Below List
- 19 Days On Market
- $827/SF
- Current Est. Value $2M
Penn Henderson COMPASS

$1,300,000

Sold Apr 2, 2026
- 3 Beds
- 2 Baths
- 1,528 Sq Ft
73-4368 Kapuahi St

Kailua-Kona, HI
- 8% Below List
- 91 Days On Market
- $851/SF
- Current Est. Value $1M
Penn Henderson COMPASS

$1,300,000

Sold Dec 23, 2025
- 3 Beds
- 2 Baths
- 1,052 Sq Ft
76-6246 Alii Dr

Unit 401

Kailua Kona, HI
- 1 Day On Market
- $1,236/SF
- Current Est. Value $1M
Penn Henderson COMPASS

$380,000

Sold Sep 19, 2025
- 1 Bed
- 1 Bath
- 492 Sq Ft
68-3831 Lua Kula St

Unit I208

Waikoloa, HI
- 7% Below List
- 176 Days On Market
- $772/SF
- Current Est. Value $363K
Penn Henderson COMPASS

$465,000

Sold Jun 24, 2025
- Land
- 6.70 Acres Lot
44-3895 Kukuipapa Rd

Honokaa, HI
- 21 Days On Market
Penn Henderson COMPASS

$595,000

Sold Jun 10, 2025
- 2 Beds
- 1.5 Baths
- 800 Sq Ft
75-5855 Walua Rd

Unit 20

Kailua Kona, HI
- 8% Below List
- 84 Days On Market
- $744/SF
- Current Est. Value $535K
Penn Henderson COMPASS

$452,500

Sold May 6, 2025
- 2 Beds
- 2 Baths
- 960 Sq Ft
87-3205 Guava Rd

Captain Cook, HI
- 3% Above List
- 2 Days On Market
- $471/SF
- Current Est. Value $544K
Penn Henderson COMPASS

$807,000

Sold May 6, 2025
- 3 Beds
- 2 Baths
- 1,177 Sq Ft
75-5919 Alii Dr

Unit GG1

Kailua Kona, HI
- 5% Below List
- 105 Days On Market
- $686/SF
- Current Est. Value $769K
Penn Henderson COMPASS

$467,000

Sold May 8, 2024
- 1 Bed
- 1 Bath
- 639 Sq Ft
75-5766 Kuakini Hwy

Unit 201

Kailua Kona, HI
- 4% Below List
- 93 Days On Market
- $731/SF
- Current Est. Value $407K
Penn Henderson COMPASS

Awards and Designations

Five Star Award
Top Kona REALTOR®
West Hawaii REALTOR® Rising Star Award
NAR - National Association of Realtors
AHWD - At Home with Diversity
e–PRO - Internet Professional
LHC - Luxury Homes Certification
RSPS - Resort & Second-Home Property Specialist

Other Experience

First Time Homebuyers, Investments, Luxury Homes, New Construction

Agent License: Hawaii #RS83962

Frequently Asked Questions

Who is Penn Henderson, and what is their real estate background?

How many homes has Penn Henderson sold in Kailua Kona, HI?

What is Penn Henderson's track record representing buyers?

What is Penn Henderson's track record as a listing agent?

What areas does Penn Henderson serve?

How can I contact Penn Henderson?

Penn Henderson

(808) 731-1136

Nearby Homes

Penn Henderson

About Penn

Transaction History

Seller Deals

Buyer Deals

Production Over Time

1 Year View by Quarter

Seller Deals

Buyer Deals

Seller Deals

Buyer Deals

Production Over Time

5 Year View

Areas Penn is Experienced In

Penn's Listings and Deals

Penn's Active Listings

Recently Sold

Awards and Designations

Other Experience

Frequently Asked Questions

Who is Penn Henderson, and what is their real estate background?

How many homes has Penn Henderson sold in Kailua Kona, HI?

What is Penn Henderson's track record representing buyers?

What is Penn Henderson's track record as a listing agent?

What areas does Penn Henderson serve?

How can I contact Penn Henderson?