Penn Henderson

Kailua-Kona HI

NextHome Paradise Realty

58 Closed Sales

$67.2M Total Value

$15K - $8.2M Price Range

$1.2M Average Price

Prior 5 years

About Penn

Aloha from Hawaii! Penn Henderson is a top 3% Big Island REALTOR® with NextHome Paradise Realty, specializing in luxury, oceanfront, and investment properties across Kona, Kohala Coast, Waimea, and Waikoloa. Living in Kona since 2001, Penn blends 24 years of island experience with consistent $20M+ annual sales. Recognized with the NextHome President’s Circle Award and the West Hawaii REALTOR® Rising Star Award, he’s known for professionalism, integrity, and results. Certified in CLHMS, REALM®, and PSA, Penn guides clients through Hawaii’s real estate market with trusted expertise and genuine aloha.

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

Total Value

$6,974,500

Average Sale Price

$774,944

Price Range

$75K - $1.6M

Buyer Deals

Total Deals

Neighborhoods Penn is Experienced In

Kailua Kona

40 Sales
Waikoloa

6 Sales
Ocean View

4 Sales
Captain Cook

3 Sales
Kamuela

3 Sales
Honokaa

1 Sale

Penn's Active Listings

$500,000
- Land
- 1.39 Acres
- $359,712 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 NextHome Paradise Realty

$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 bedrooms and

Penn Henderson NextHome Paradise Realty

$97,500
- Land
- 0.17 Acre
- $573,529 per Acre
87-435 Kaohe Rd

Captain Cook, HI
Rare Corner Lot with Ocean Views - awaiting your vision! Imagine your own slice of paradise — an untouched piece of land on Hawai‘i Island’s sunny South Kona coast with sweeping ocean views and year-round sunsets. Located in the established community of Kona Paradise, this unique corner parcel offers the perfect setting for your future island home or getaway retreat.Kona Paradise is a

Penn Henderson NextHome Paradise Realty

$43,000
- Land
- 0.17 Acre
- $252,941 per Acre
88-1546 Ehiku Ave

Captain Cook, HI
Discover your own piece of paradise in Miloli‘i Beach Lots, one of Hawai‘i Island’s most unique and historically rich coastal communities. Located in sunny South Kona, this vacant lot offers partial ocean views and an authentic island lifestyle just minutes from the water. Enjoy year-round sunshine, spectacular sunsets, and proximity to some of Hawai'i's clearest waters— perfect for snorkeling,

Penn Henderson NextHome Paradise Realty

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
- $827/SF
- 19 Days On Market
- Current Est. Value $2M
Penn Henderson NextHome Paradise Realty

$75,000 Sold Apr 2, 2026
- Land
- 3.00 Acre Lot
0 Road 9 (Koloa Maoli)

Unit 728023

Mountain View, HI
- 1 Day On Market
Penn Henderson NextHome Paradise Realty

$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
- $851/SF
- 91 Days On Market
- Current Est. Value $1M
Penn Henderson NextHome Paradise Realty

$1,300,000 Sold Dec 23, 2025
- 3 Beds
- 2 Baths
- 1,052 Sq Ft
76-6246 Alii Dr

Unit 401

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

$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
- $772/SF
- 176 Days On Market
- Current Est. Value $374K
Penn Henderson NextHome Paradise Realty

$465,000 Sold Jun 24, 2025
- Land
- 6.70 Acre Lot
44-3895 Kukuipapa Rd

Honokaa, HI
- 21 Days On Market
Penn Henderson NextHome Paradise Realty

$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
- $744/SF
- 84 Days On Market
- Current Est. Value $569K
Penn Henderson NextHome Paradise Realty

$452,500 Sold May 6, 2025
- 2 Beds
- 2 Baths
- 960 Sq Ft
87-3205 Guava Rd

Captain Cook, HI
- 3% Above List
- $471/SF
- 2 Days On Market
- Current Est. Value $563K
Penn Henderson NextHome Paradise Realty

$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
- $686/SF
- 105 Days On Market
- Current Est. Value $796K
Penn Henderson NextHome Paradise Realty

Awards and Designations

Five Star Award
NextHome President's Circle 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 Home Buyers, Investments, Luxury Homes, New Construction

Agent License: Hawaii #RS83962

Penn Henderson

(808) 731-1136

Homes for Sale by City

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

Neighborhoods Penn is Experienced In

Penn's Listings and Deals

Penn's Active Listings

Recently Sold

Awards and Designations

Other Experience