$2,995,000
 $16,078 est/mo Sourced by Back At You

1055 Kaupakalua Rd,Haiku, HI 96708

Haiku, HI 96708

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Description

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.

Details

MLS #408773
Listing TypeFor Sale
StyleHouse
Sub-TypeResale
StatusActive
Year1975
Days On Site208
Listing Provided ByHawaii Life (W) | Josh Jerman
TypeSF w/Det Ohana or Cottage

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:
$2,995,000
low | high
Med:
$1,062,500
100% of Average
sqft:
4,550
low | high
Med:
1,204
100% of Average
$ / sqft:
$658
low | high
Med:
$935
7.962621349872% of Average
On site:
208
low | high
Med:
32
100% 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:
$2,995,000
low | high
Med:
$1,062,500
100% of Average
sqft:
4,550
low | high
Med:
1,204
100% of Average
$ / sqft:
$658
low | high
Med:
$935
7.962621349872% of Average
On site:
208
low | high
Med:
32
100% of Average
Sourced by Back At You
Listing Updated: September 1, 2026 at 8:45:53 PM PDT