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1055 Kaupakalua Rd, 
Haiku, HI 96708

$3,950,000


5

Beds


3

Baths


4,550

Sq Ft


Single Family

Active

Listed by

Josh Jerman Rb-19728

Tim Stice Rb-21556

Hawaii Life (W)

800-677-5028

Last updated:

March 2, 2026, 06:41 PM

MLS#

408773

Source:

HI RAM

About This Home

1055 Kaupakalua Rd

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.

Home Facts

Single Family

3 Baths

5 Bedrooms

Built in 1975

Price Summary

3,950,000

$868 per Sq. Ft.

MLS #:

408773

Last Updated:

March 2, 2026, 06:41 PM

Added:

17 day(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

5

Bathrooms

Total Bathrooms:

3

Interior

Living Area:

4,550 Sq. Ft.


Structure

Structure

Building Area:

4,550 Sq. Ft.

Year Built:

1975


Lot

Lot Size (Sq. Ft):

698,397


Finances & Disclosures

Finances

Price:

$3,950,000

Price per Sq. Ft:

$868 per Sq. Ft.

Source:HI RAM
The information being provided by REALTORS® Association Of Maui, Inc. is for the consumer’s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The information is deemed reliable but not guaranteed and should therefore be independently verified. © 2026 REALTORS® Association Of Maui, Inc. All rights reserved.

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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.