1055 Kaupakalua Rd

Haiku, HI 96708

$3,950,000
Price
5
Beds
3
Baths
4,550 Sq. Ft.
$868 / Sq. Ft.
4,550
Sq. Ft.
$868
per Sq. Ft.
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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...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.
  1. Listed by Josh Jerman • License #RB-19728 • Hawaii Life (W)
    P: (808)-283-2222 josh@hawaiilife.com
  2. Listed by Tim Stice • License #RB-21556 • Hawaii Life (W)
    P: (808)-268-8511 timstice@hawaiilife.com

Property Details for 1055 Kaupakalua Road

View
Mountain/Ocean
Waterfront Features
None
Waterfront
No
LISTING UPDATED: 03/02/2026 07:50 AM

Property Details for 1055 Kaupakalua Road

StatusActive
MLS #408773
Days on Market47
Taxes-
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family Residence
Year Built1975
Lot Size16.03 AC / 698,397 SF
CountyMaui County
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Location

Listing Courtesy of Hawaii Life (W), Josh Jerman, License #RB-19728; Hawaii Life (W), Tim Stice, License #RB-21556
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Building Information for 1055 Kaupakalua Road

Stories-Year Built1975Building Size-Lot Size16.03 AC / 698,397 SF

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$20,734 per month

30 year fixed, 6.46% Interest

Principal and Interest

$19,890

Property Taxes

$844

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 1055 Kaupakalua Road

Summary
Location and General Information
  • Coordinates: -156.286898, 20.901768
  • Latitude: 20.901768
  • Longitude: -156.286898
  • View YN: Yes
  • FIPS Code: 15009
  • Multiple Address: 1055 Kaupakalua Rd
Taxes and HOA Information
  • Tax ID: 2270130500000
  • Tax Legal Description: 1
  • Tax Other Annual Assessment Amount: 0.0
Parking
  • Carport: No
  • Garage: No
  • Parking Features: No Garage
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Property Information
Lot Information
  • Building Area Total: 4550.0
  • Building Area Units: Square Feet
  • Land Improvements: Wall/Fence
  • Living Area: 4550.0
  • Lot Desc: Driveway Easement
  • Lot Size Units: Acres
  • MLS Area Major: Haiku
  • CPR: 0000
Property and Assessments
  • Home Warranty: No
  • Levels: One
Utilities
  • Water: Public
Interior and Exterior Features
Exterior Features
  • Pool Features: In Ground
  • Other Features: Wall/Fence, Sauna
Interior Features
  • Appliances: Dishwasher, Dryer, Microwave, Range, Refrigerator, Solar Hot Water
  • Bathrooms: 3
  • Fireplace: Yes
  • Flooring: Wood, Tile
  • Heating: Fireplace(s), Solar Water Heating
  • Heating YN: No
  • Interior Features: Ceiling Fan(s), Furnished, Kitchen Ware, Sauna
  • Room Primary Bedroom Level: Ground
  • Additional Rooms: Dining Area, Work Space

Property History for 1055 Kaupakalua Road

DateEvent & SourcePriceAppreciation
Feb 15, 2026

Listed (Active)

MAUIMLS #408773

$3,950,000—
Aug 19, 2019

Sold

MAUIMLS #382284

$2,115,000—
Aug 13, 2019

Sold (Public Record)

Public Record #651361508

$2,115,000

+0.1% / yr

May 29, 2019

Contract Signed

MAUIMLS #382284

—
Mar 25, 2019

Listed (Active)

MAUIMLS #382284

$2,350,000—
Jul 11, 2007

Permanently Off Market

MAUIMLS #321540

$2,950,000—
Dec 11, 2006

Listed (Active)

MAUIMLS #321540

$3,500,000—
Aug 4, 2003

Sold

MAUIMLS #222953

$2,075,000—
Jul 29, 2003

Sold (Public Record)

Public Record #117499759

$2,075,000—
Apr 25, 2003

Contract Signed

MAUIMLS #222953

—
Oct 27, 2002

Permanently Off Market

MAUIMLS #215725

$2,400,000—
Oct 22, 2002

Listed (Active)

MAUIMLS #222953

$2,400,000—
Mar 20, 2001

Listed (Active)

MAUIMLS #215725

$3,350,000—
DateEvent & SourcePrice
02/15/2026

Listed (Active)

MAUIMLS #408773

$3,950,000
08/19/2019

Sold

MAUIMLS #382284

$2,115,000
08/13/2019

Sold (Public Record)

Public Record #651361508

$2,115,000

+0.1% / yr

05/29/2019

Contract Signed

MAUIMLS #382284

—
03/25/2019

Listed (Active)

MAUIMLS #382284

$2,350,000
07/11/2007

Permanently Off Market

MAUIMLS #321540

$2,950,000
12/11/2006

Listed (Active)

MAUIMLS #321540

$3,500,000
08/04/2003

Sold

MAUIMLS #222953

$2,075,000
07/29/2003

Sold (Public Record)

Public Record #117499759

$2,075,000
04/25/2003

Contract Signed

MAUIMLS #222953

—
10/27/2002

Permanently Off Market

MAUIMLS #215725

$2,400,000
10/22/2002

Listed (Active)

MAUIMLS #222953

$2,400,000
03/20/2001

Listed (Active)

MAUIMLS #215725

$3,350,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 1055 Kaupakalua Road

Taxable ValueLand$1,899,900Additions$1,323,400Total$3,223,300
Tax Record2025$10,134 ($844 / month)
Home Facts
Beds8Baths7Total Finished SqFt4,550 SqFtAbove Grade Finished SqFt4,550 SqFtStories1Lot Size698,397 SqFtStyleSingle Family ResidenceYear Built1920Year Renovated2000ZoningAGRCountyMAUIAPN2-7-013-050

Schools near 1055 Kaupakalua Road

This home is within Hawaii Department Of Education.
Rating
School
Type
Grades
Distance
Haiku Elementary School
Public - PK to 5
Samuel Enoka Kalama Intermediate School
Public - 6 to 8
King Kekaulike High School
Public - 9 to 12
Kulanihakoi High School
Public - 9 to 11
Rating
School
Distance
Haiku Elementary School
PublicPK to 5

Samuel Enoka Kalama Intermediate School
Public6 to 8

King Kekaulike High School
Public9 to 12

Kulanihakoi High School
Public9 to 11

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 1055 Kaupakalua Road, Haiku, HI 96708

1055 Kaupakalua Road is a single family home for sale in Haiku, HI 96708. This property was listed for sale on February 16, 2026 by Hawaii Life (W), it's currently listed at $3,950,000. It has been on the market for a total of 47 days and was last sold on August 20, 2019. This listing's school district is Hawaii Department Of Education. Nearby schools include Haiku Elementary School, Samuel Enoka Kalama Intermediate School and King Kekaulike High School. 1055 Kaupakalua Road is a 5-bed, 3-bath, 4,550 sqft single family home built in 1975.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Hawaii Life (W), Josh Jerman, License #RB-19728; Hawaii Life (W), Tim Stice, License #RB-21556

Based on information from one of the following Multiple Listing Services: Hawaii HIS, MAUI MLS and Hi Central. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Hawaii HIS, MAUI MLS and Hi Central is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.