Ad #7280511
MLS #408773
Set across sixteen acres of fully fenced acreage, this Haiku
1055 Kaupakalua Rd, Haiku, HI 96708
$3,495,000
5Beds
3Baths
4,550Sqft
16.03Acres
About this property
Set across sixteen acres of fully fenced acreage, this Haiku estate is a world unto itself. Private, expansive, and rich with possibility. Thoughtfully positioned structures create a harmonious compound designed for inspired living, hosting, and creativity. Whether envisioned as an exclusive mountain residence, an artist's enclave, or a destination wellness retreat, the setting effortlessly supports a life well-lived. At the heart of the property, the main home captures the essence of refined rural living. An impressive primary suite is wrapped in glass windows and doors, inviting natural light and lush views from nearly every angle. A warm fireplace lounge in the living area sets the tone for intimate evenings, while a concealed projection screen transforms the space into a private cinema. The screened lanai area offers flexibility for gatherings or hosting events of any kind. Throughout the grounds, there are additional dwellings and versatile spaces, including a two-room cottage currently utilized as an office, an upper guest cottage with its own outdoor shower house, and a two-story building tucked privately toward the rear of the acreage. Each structure enhances the estate's ability to accommodate guests or creative pursuits. The outdoor experience is equally compelling. Pass by the courtyard area and enjoy the sounds of the cascading waterfall and koi fish pond, and head out to meandering trails that wind through the landscape. A commercial-grade kitchen with an adjacent screened-in gathering space, along with dedicated men's and women's bathhouses, reflects the property's history as a curated retreat destination. Leisure and restoration take center stage with a resort-style pool complete with a water slide, waterfall, an accompanying pool house, and a tranquil massage pavilion. This is more than acreage; it is a legacy estate with the capacity to evolve alongside your vision, all within a setting that feels worlds away.
Property Features
5 Beds
3 Baths
4,550 Sqft
16.03 Acres
Additional Photos
Contact Information
Josh Jerman
Hawaii Life Real Estate Brokers
808-283-2222
Location
Listing Agent: Josh Jerman 808-283-2222
Broker: Hawaii Life Real Estate Brokers 800-370-3848 Listing Site
Copyright © 2026 Realtors ® Association of Maui, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
Broker: Hawaii Life Real Estate Brokers 800-370-3848 Listing Site
Copyright © 2026 Realtors ® Association of Maui, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
BeachHouse.com
Printed Aug 11, 2026
Photo Gallery
$3,495,000
5
Beds
3
Baths
4,550
Sqft
1055 Kaupakalua Rd, Haiku, HI 96708
By contacting this agent you agree to these Terms and Conditions.
MLS# 408773
Set across sixteen acres of fully fenced acreage, this Haiku
$3,495,000
1055 Kaupakalua Rd, Haiku, HI 96708
5
Beds
3
Baths
4,550
Sqft
16.03
Acres
$3,495,000
1055 Kaupakalua Rd, Haiku, HI 96708
5 Beds
3 Baths
4,550 Sqft
16.03 Acres
Set across sixteen acres of fully fenced acreage, this Haiku estate is a world unto itself. Private, expansive, and rich with possibility. Thoughtfully positioned structures create a harmonious compound designed for inspired living, hosting, and creativity. Whether envisioned as an exclusive mountain residence, an artist's enclave, or a destination wellness retreat, the setting effortlessly supports a life well-lived. At the heart of the property, the main home captures the essence of refined rural living. An impressive primary suite is wrapped in glass windows and doors, inviting natural light and lush views from nearly every angle. A warm fireplace lounge in the living area sets the tone for intimate evenings, while a concealed projection screen transforms the space into a private cinema. The screened lanai area offers flexibility for gatherings or hosting events of any kind. Throughout the grounds, there are additional dwellings and versatile spaces, including a two-room cottage currently utilized as an office, an upper guest cottage with its own outdoor shower house, and a two-story building tucked privately toward the rear of the acreage. Each structure enhances the estate's ability to accommodate guests or creative pursuits. The outdoor experience is equally compelling. Pass by the courtyard area and enjoy the sounds of the cascading waterfall and koi fish pond, and head out to meandering trails that wind through the landscape. A commercial-grade kitchen with an adjacent screened-in gathering space, along with dedicated men's and women's bathhouses, reflects the property's history as a curated retreat destination. Leisure and restoration take center stage with a resort-style pool complete with a water slide, waterfall, an accompanying pool house, and a tranquil massage pavilion. This is more than acreage; it is a legacy estate with the capacity to evolve alongside your vision, all within a setting that feels worlds away.
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Property Details
HOME DETAILS
5 Beds
3 Baths
4,550 Sqft
16.03 Acres
Location
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Ad Statistics
Ad Number
7280511
Viewed
143 times
Listing Status
Active
Added
Feb 17, 2026
Last Refreshed
Jul 03, 2026 06:17:28 PM
Listing Information
Data Source
Realtors ® Association of Maui, Inc.
Source Property ID
408773
Listing Agent: Josh Jerman 808-283-2222
Broker: Hawaii Life Real Estate Brokers 800-370-3848 Listing Site
Copyright © 2026 Realtors ® Association of Maui, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
Broker: Hawaii Life Real Estate Brokers 800-370-3848 Listing Site
Copyright © 2026 Realtors ® Association of Maui, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
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