1055 Kaupakalua Rd, Haiku, HI 96708

bedrooms 5
bathrooms 3
|Other
NZD $5,321,181
USD $2,995,000
Published on: 18 Feb 2026
Last updated on: 28 Oct 2026
1055 Kaupakalua Rd, Haiku, HI 96708
1055 Kaupakalua Rd, Haiku, HI 96708
1055 Kaupakalua Rd, Haiku, HI 96708
+50
1055 Kaupakalua Rd, Haiku, HI 96708
  • 50
Property ID: 110105797018
Translate to English

Residential, Haiku, HI

1055 Kaupakalua Rd, Haiku, HI 96708
Set across 16 fully fenced and gated acres in Ha'iku, this expansive Maui estate offers privacy, substantial infrastructure, multiple structures, and considerable flexibility. The property is served by a County of Maui 5/8-inch water meter and a high-capacity well nearing completion, and is potentially subdividable subject to applicable County approvals. More than 20 varieties of mature exotic fruit trees and flowering plants are established throughout the grounds, with walking paths connecting the residences and amenities. At the center of the property is a 5,000+ square-foot main residence with five bedrooms, three bathrooms (two are large/bathhouse style), and a spacious commercial-type kitchen. The primary suite is surrounded by walls of glass overlooking the tropical landscape. The living room features a fireplace and concealed projection screen, while a large screened lanai provides additional space for dining and entertaining. A landscaped courtyard with a cascading waterfall and koi pond leads to trails winding throughout the property. A separate commercial-grade kitchen, adjoining screened gathering area, and dedicated men's and women's bathhouses reflect the property's history as a retreat destination and provide additional flexibility for larger gatherings. Additional structures include a two-room cottage currently used as an office, an upper guest cottage with a private outdoor shower house, and a separate two-story building tucked toward the rear of the acreage. These spaces provide options for guests, offices, studios, workshops, storage, or other uses. Outdoor amenities include a resort-style swimming pool with a waterfall and slide, pool house, massage pavilion, and extensive landscaped grounds. The estate is offered fully furnished, including more than $150,000 in furnishings, artwork, and antiques, with appraisals available. With 16 acres, multiple structures, established infrastructure, extensive landscaping, and potential subdivision opportunities, this Ha'iku property offers a range of possibilities as a private estate, multigenerational compound, creative retreat, or long-term Maui investment.

Property Details

Basic Info

Property Type
Other
Listing Status
Pending
Land Size
64,883.31 m2
Building Size
422.71 m2
Rooms
5 bedroom(s), 3 bathroom(s)
Provider
Realtors ® Association of Maui, Inc.
Brokerage Office Name
Hawaii Life Real Estate Brokers
Brokerage Office Phone
(800) 370-3848
Neighbourhoods
Haiku
Address
1055 Kaupakalua Rd, Haiku, HI 96708
Contact Agent
Josh Jerman
Hawaii Life (W)
Wailea, HI
Get in touch
Report this page

Contact Agent

Contact Agent

Email enquiry to Hawaii Life (W)

Josh Jerman
Wailea, HI
What's your enquiry about?
      By clicking "Submit", you accept our Privacy Policy and acknowledge that as the agent for this property is located overseas, your information may not be handled in accordance with the privacy laws applicable to this website.

      Property ID: 110105797018

      Original Property ID: 3yd-RAMHI-408773
      Data provided by Realtors ® Association of Maui, Inc., MLS #: 408773
      * THIS SERVICE MAY CONTAIN TRANSLATIONS POWERED BY GOOGLE. GOOGLE DISCLAIMS ALL WARRANTIES RELATED TO THE TRANSLATIONS, EXPRESS OR IMPLIED, INCLUDING ANY WARRANTIES OF ACCURACY, RELIABILITY, AND ANY IMPLIED WARRANTIES OF MERCHANTABILITY, FITNESS FOR A PARTICULAR PURPOSE AND NONINFRINGEMENT.
      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.