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.
For sale
$3,950,000
1055 Kaupakalua Rd, Haiku, HI 96708
5beds
3baths
4,550sqft
Est.:
Single Family Residence, Residential
Built in 1975
16.03 Acres Lot
$3,040,800 Zestimate®
$868/sqft
$-- HOA
What's special
Accompanying pool houseTranquil massage pavilionPrivate expansive
- 6 days |
- 1,259 |
- 66 |
Zillow last checked: 8 hours ago
Listing updated: February 16, 2026 at 04:23pm
Listing Provided by:
Josh Jerman RB-19728 Cell:808-283-2222,
Hawaii Life (W),
Tim Stice RB-21556 808-268-8511,
Hawaii Life (W)
Source: RAM,MLS#: 408773
Tour with a local agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 3
Primary bedroom
- Level: Ground
Appliances
- Included: Dishwasher, Dryer, Microwave, Range, Refrigerator, Solar Hot Water
Features
- Ceiling Fan(s), Kitchen Ware, Sauna
- Has fireplace: Yes
- Furnished: Yes
Interior area
- Total structure area: 4,550
- Total interior livable area: 4,550 sqft
Video & virtual tour
Property
Parking
- Parking features: No Garage
Features
- Levels: One
- Stories: 1
- Has private pool: Yes
- Pool features: In Ground
- Fencing: Wall/Fence
- Has view: Yes
- View description: Mountain/Ocean
- Has water view: Yes
- Water view: Mountain/Ocean
- Waterfront features: None
Lot
- Size: 16.03 Acres
Details
- Parcel number: 2270130500000
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence, Residential
Condition
- Year built: 1975
Utilities & green energy
- Water: Public
Community & HOA
Location
- Region: Haiku
Financial & listing details
- Price per square foot: $868/sqft
- Tax assessed value: $2,909,200
- Annual tax amount: $5,018
- Date on market: 2/17/2026
Estimated market value
$3,040,800
$2.40M - $3.80M
$3,010/mo
Price history
Price history
| Date | Event | Price |
|---|---|---|
| 2/17/2026 | Listed for sale | $3,950,000+86.8%$868/sqft |
Source: | ||
| 8/20/2019 | Sold | $2,115,000+1.9%$465/sqft |
Source: | ||
| 7/29/2003 | Sold | $2,075,000$456/sqft |
Source: Public Record Report a problem | ||
Public tax history
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | $5,018 +10.5% | $2,909,200 +11% |
| 2023 | $4,540 +6% | $2,620,100 +14.5% |
| 2022 | $4,284 -11.1% | $2,287,400 +8% |
| 2021 | $4,819 -47.2% | $2,118,400 +4.9% |
| 2020 | $9,134 -2.3% | $2,019,000 +31.3% |
| 2019 | $9,349 | $1,537,700 -1.3% |
| 2018 | $9,349 +26.2% | $1,558,200 |
| 2017 | $7,410 +7% | -- |
| 2016 | $6,927 | $1,223,900 +6.3% |
| 2015 | -- | $1,151,900 |
Find assessor info on the county website
BuyAbility℠ payment
Est. payment
$20,864/mo
Principal & interest
$20370
Property taxes
$494
Climate risks
Neighborhood: 96708
Nearby schools
GreatSchools rating
- 6/10Haiku Elementary SchoolGrades: PK-5Distance: 2.9 mi
- 5/10Samuel Enoka Kalama Intermediate SchoolGrades: 6-8Distance: 4.1 mi
- 5/10King Kekaulike High SchoolGrades: 9-12Distance: 5.7 mi



