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1055 Kaupakalua Rd, Haiku, HI, 96708
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1055 Kaupakalua Rd, Haiku, HI 96708

$3,950,000 Home for sale 5 beds 3 baths 4,550 sqft
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.
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Home details

4,550 sqft interior area
  • Year Built 1975
  • Original list price $3,950,000
  • Days on market 2
  • Price per sqft $868/sqft
  • Baths 3
  • Beds 5
  • Address

    1055 Kaupakalua Rd, Haiku, HI, 96708

  • Total area 4,550 sqft
  • Interior area 4,550 sqft
  • Land area 698,397 sqft
  • Frontage None
  • Pool In Ground
  • City of Maui Haiku
  • Region Haiku
  • Island Maui
  • View Mountain/Ocean
  • Virtual Tour View (external link)

Open Houses

No upcoming open houses

Monthly payment

Calculate your monthly payments
Mortgage
$20,140
Taxes
$0
HOA dues
$0
$20,140 per month
Mortgage
Down payment
$790,000 / 20%
Interest rate
6.58%
Loan type
30 years
Your amount $20,140 / month

Neighborhood:

Nearby & commute
Walkability
Coffee shops
no data
Bus stop
no data
Supermarket
no data
Costco
no data
Hospital
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Park
no data
Beach
no data
Elementary school
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Middle school
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High school
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Local airport
no data
3.83 / 20
Car dependent
18-20
15-18
10-15
1-10
Walkability according to the National Walkability Index

Amenities & Features

Utilities
Public

Schools

15 schools in this area
School rating Distance
NR
Haiku Elementary School
105 Pauwela Rd, Haiku, HI 96708
Elementary School
2.933mi
NR
Montessori School of Maui
2933 Baldwin Ave, Makawao, HI 96768
Middle School
3.247mi
NR
Seabury Hall School
480 Olinda Road, Makawao, HI 96768
High School
4.458mi
School rating Distance
NR
Haiku Elementary School
105 Pauwela Rd, Haiku, HI 96708
2.933mi
NR
Montessori School of Maui
2933 Baldwin Ave, Makawao, HI 96768
3.247mi
NR
St. Joseph School
1294 Makawao Ave, Makawao, HI 96768
3.523mi
NR
Makawao Elementary School
3542 Baldwin Ave, Makawao, HI 96768
3.532mi
NR
Paia Elementary School
955 Baldwin Ave, Paia, HI 96779
4.936mi
School rating Distance
NR
Montessori School of Maui
2933 Baldwin Ave, Makawao, HI 96768
3.247mi
NR
Samuel Enoka Kalama Intermediate School
120 Makani Rd, Makawao, HI 96768
4.233mi
NR
Seabury Hall School
480 Olinda Road, Makawao, HI 96768
4.458mi
NR
Doris Todd Christian Academy
519 Baldwin Avenue, Paia, HI 96779
5.472mi
NR
Clearview Christian Girl School
Po Box 880678, Pukalani, HI 96788
5.478mi
School rating Distance
NR
Seabury Hall School
480 Olinda Road, Makawao, HI 96768
4.458mi
NR
King Kekaulike High School
121 Kula Hwy, Pukalani, HI 96768
5.728mi
NR
Kamehameha Schools Maui
270 Aapueo Parkway, Makawao, HI 96768
6.263mi
NR
Kaahumanu Hou Christian School
777 Mokulele Highway, Kahului, HI 96732
11.264mi
NR
Maui High School
660 South Lono Ave, Kahului, HI 96732
12.116mi
School ratings provided by Greatschools.org © 2023. All rights reserved.

Price history

Sold Aug 20, 2019
Date Event Price $/sqft Source
Aug 20, 2019 Sold $2,115,000 -10% from last sold price $464.84 Public Record
Jun 3, 2019 Pending $2,350,000 $516.48 MLS #382284
Mar 26, 2019 New Listing $2,350,000 $516.48 MLS #382284
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Tax & MLS details 1055 Kaupakalua Rd, Haiku, HI, 96708

MLS #408773
TMK
2270130500000
Listed by
Hawaii Life (W)
Cell: 808-283-2222
MLS #
408773
Hawaii House tour report for this home
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Frequently asked questions for 1055 Kaupakalua Rd

What is 1055 Kaupakalua Rd?

1055 Kaupakalua Rd, Haiku, HI, 96708 is a single family home located in the  neighborhood of the Haiku region in the city of Haiku in zipcode 96708. This single family home has 5 bedrooms & 3 bathrooms with an interior area of 4550 sqft, on a 698397 sqft lot.

When was this home built and last sold?

This house was build in 1975.

What is the full address of this home?

1055 Kaupakalua Rd, Haiku, HI, 96708.

Are there beaches near 1055 Kaupakalua Rd?

No, there aren't.

Based on information from the Realtors Assoc. of Maui. Copyright 2026 by REALTORS® Association of Maui, Inc. Listing courtesy of Hawaii Life (W). 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.

Listings last updated on February 16, 2026.
Hawaii House Last checked 1 year ago.

1055 Kaupakalua Rd, Haiku, HI, 96708 is a single family home located in the  neighborhood of the Haiku region in the city of Haiku in zipcode 96708. This single family home has 5 bedrooms & 3 bathrooms with an interior area of 4550 sqft, on a 698397 sqft lot. This house was build in 1975.
*Neighborhood & street median sales price are calculated over sold properties over the last 6 months.

Home for sale $3,950,000 1055 Kaupakalua Rd, Haiku, HI, 96708 5 beds | 3 baths | 4,550 sqft Save House Remove from Saved