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1055 Kaupakalua Rd

Haiku, HI 96708
  • $3,950,000
  • STATUS: Active
  • ON SITE: 53 Days
  • MLS #: 408773
UPDATED: 38 min ago
$3,950,000
  • 5
    BEDS
  • 16.03
    ACRES
  • 3
    BATHS
  • 0
    1/2 BATHS
  • 4,550
    SQFT
  • $868
    $/SQFT
Neighborhood:
Type:
Single-Family Home
Built:
1975
Area:
Land Tenure:
Fee Simple

School Ratings & Info

Listing provided courtesy of Hawaii Life (W): Cell: 808-283-2222.





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.

Monthly Payment Calculator

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. Copyright, 1995-2026, REALTORS® Association of Maui, Inc. All Rights Reserved. Data last updated: 2026-04-11T01:06:14.877.
www.gmmauigroupre.com/homes/173098312
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1055 Kaupakalua Rd Haiku, HI 96708

  • Price: $3,950,000
  • Status: Active
  • On Site: 53 Days
  • Updated: 38 min ago
  • MLS #: 408773
5
Beds
3
Baths
0
½ Baths
16.03
Acres
4,550
SQFT
$868
$/SQFT
1975
Built
Neighborhood:
Haiku
Area:
Haiku
Property 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.
Exterior Features

Carport YN No Fencing Wall/Fence Garage YN No Parking Features No Garage Pool Yes Pool Features In Ground View Mountain/Ocean View YN Yes Waterfront Features None Waterfront YN No

Interior Features

Appliances DishwasherDryerMicrowaveRangeRefrigeratorSolar Hot Water Fireplace YN Yes Interior Features Ceiling Fan(s)FurnishedKitchen WareSauna Levels One Master Bedroom Level Ground

Property Features

Home Warranty YN No Land Tenure Fee Simple Potential Short Sale No Property Sub Type Single Family Residence Water Source Public Zone 2

Listing provided courtesy of Hawaii Life (W): Cell: 808-283-2222.
Listing information © 2026 REALTORS® Association of Maui, Inc.
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. Copyright, 1995-2026, REALTORS® Association of Maui, Inc. All Rights Reserved. Data last updated: 2026-04-11T01:06:14.877.
 
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GM Maui Group of Coldwell Banker Island Properties
3750 Wailea Alanui #A37
Wailea HI, 96753
Listing provided courtesy of Hawaii Life (W): Cell: 808-283-2222.