$3,495,000
 $18,762 est/mo Sourced by Back At You

1055 Kaupakalua Rd,Haiku, HI 96708

Haiku, HI 96708

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Description

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.

Details

MLS #408773
Listing TypeFor Sale
StyleHouse
Sub-TypeResale
StatusActive
Year1975
Days On Site185
Listing Provided ByHawaii Life (W) | Josh Jerman
TypeSingle Family Residence

Features

Bed(s)5
Bath(s) 3 Total
SQ Feet4,550
PoolYes
Story(s)1
Acreage16.03
Property ViewYes

Interior

Interior FeaturesCeiling Fan(s), Furnished, Kitchen Ware, Sauna
AppliancesDishwasher, Dryer, Microwave, Range, Refrigerator, Solar Hot Water
Fireplace Yes / NoYes

Exterior

FencingWall/Fence

Parking

Garage Yes / NoNo
Parking FeaturesNo Garage

Area Information

StateHI
CityHaiku
Zip Code96708
AreaMaui
SubareaHaiku
Community NameHI
Listing VS Median (in HI)
Price:
$3,495,000
low | high
Med:
$1,050,000
100% of Average
sqft:
4,550
low | high
Med:
1,219
100% of Average
$ / sqft:
$768
low | high
Med:
$878
35.717889744555% of Average
On site:
185
low | high
Med:
258
71.705426356589% of Average
Sourced by Back At You

Market Activity 96708

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This information is believed to be accurate. It has been provided by sources other than the Realtors Assoc. of Maui and should not be relied upon without independent verification. You should conduct your own investigation and consult with appropriate professionals to determine the accuracy of the information provided and to answer any questions concerning the property and structures located thereon. Featured properties may or may not be listed by the office/agent presenting this brochure. The listing broker’s offer of compensation is the dollar amount or percentage of sale price the listing broker offers to pay a broker who (a) participates in the multiple listing service where the listing broker filed the listing and (b) procures the buyer for a successful transaction. Copyright, 2026, REALTORS® Association of Maui, Inc. All Rights Reserved.

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Learn More About This Property

StateHI
CityHaiku
Zip Code96708
AreaMaui
SubareaHaiku
Community NameHI
Listing VS Median (in HI)
Price:
$3,495,000
low | high
Med:
$1,050,000
100% of Average
sqft:
4,550
low | high
Med:
1,219
100% of Average
$ / sqft:
$768
low | high
Med:
$878
35.717889744555% of Average
On site:
185
low | high
Med:
258
71.705426356589% of Average
Sourced by Back At You
Listing Updated: August 5, 2026 at 3:15:30 PM PDT