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.
For sale
Price cut: $500K (9/2)
$2,995,000
1055 Kaupakalua Rd, Haiku, HI 96708
5beds
3baths
4,550sqft
Single Family Residence, Residential
Built in 1975
16.03 Acres Lot
$3,170,200 Zestimate®
$658/sqft
$-- HOA
What's special
Pool houseMassage pavilionFive bedroomsSpacious commercial-type kitchenExtensive landscaped grounds
- 23 days
- 1,553
- 143
Zillow last checked:
Listing updated:
Listed 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
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: 4,874
- 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: $658/sqft
- Tax assessed value: $3,223,300
- Annual tax amount: $5,067
- Date on market: 8/21/2026
Estimated market value
$3,170,200
$3.01M - $3.33M
$6,103/mo
Price history
| Date | Event | Price |
|---|---|---|
| 9/2/2026 | Price change | $2,995,000-14.3%$658/sqft |
Source: | ||
| 8/21/2026 | Listed for sale | $3,495,000-11.5%$768/sqft |
Source: | ||
| 6/2/2026 | Listing removed | $3,950,000$868/sqft |
Source: | ||
| 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
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $5,067 +1% | $3,223,300 +10.8% |
| 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
Monthly payment
Est. payment



