Haiku
1055 Kaupakalua Rd, Haiku, HI
Listing Price: $2,995,000
5
Beds
3
Baths
4,550
Square feet
16.03
Acres
About 1055 Kaupakalua Rd
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.
View Similar Properties For Sale
Haiku Real Estate1055 Kaupakalua Rd
This property for sale at 1055 Kaupakalua Rd is listed for $2,995,000.00 and has been on the market for 212 day(s). It is a Fee Simple property located in Haiku on Maui. It features 5 bedroom(s) and 3.00 bathroom(s) with 4550 square feet of living space. To ask a question or to schedule a showing of this property or any other property on Maui, please contact Evan Harlow with Coldwell Banker Island Properties at 808-214-4799 or email Evan directly at evan@mauieliteproperty.com.
Facts & Features
| MLS® # | 408773 |
|---|---|
| Price | $2,995,000 |
| Bedrooms | 5 |
| Bathrooms | 3.00 |
| Square Footage | 4,550 |
| Land Tenure | Fee Simple |
| Acres | 16.03 |
| Year Built | 1975 |
| Type | Residential |
| Sub-Type | SF w/Det Ohana or Cottage |
| Status | Active |
| Property Tax | View Records |
| Short-Term Rental Allowed | No |
Price History For 1055 Kaupakalua Rd
| Date | Details | Change |
|---|---|---|
| Date: 07/08/2026 | Details: Price decreased from $3,950,000 to $3,495,000 | Change: ↓ $455,000 |
| Date: 09/01/2026 | Details: Price decreased from $3,495,000 to $2,995,000 | Change: ↓ $500,000 |
Community Information
| Address | 1055 Kaupakalua Rd |
|---|---|
| Area | Haiku |
| City | Haiku |
| State | HI |
| Zip Code | 96708 |
Amenities
| Parking | No Garage |
|---|---|
| View | Mountain/Ocean |
| Is Waterfront | No |
| Waterfront | None |
| Has Pool | Yes |
| Pool | In Ground |
Interior
| Interior Features | Ceiling Fan(s), Furnished, Kitchen Ware, Sauna |
|---|---|
| Appliances | Dishwasher, Dryer, Microwave, Range, Refrigerator, Solar Hot Water |
| Fireplace | Yes |
| Stories | One |
Additional Information
| Date Listed | February 16th, 2026 |
|---|---|
| Days on Market | 212 |
| Short Sale | No |
| RE / Bank Owned | No |
| Tax Map Key | 2270130500000 |
Listing Details
| Office | Hawaii Life (W) |
|---|---|
| Office Contact | Cell: 808-283-2222 |
