Haiku
1055 Kaupakalua Rd, Haiku, HI
Listing Price: $3,950,000
5
Beds
3
Baths
4,550
Square feet
16.03
Acres
About 1055 Kaupakalua Rd
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.
View Similar Properties For Sale
Haiku Real Estate1055 Kaupakalua Rd
This property for sale at 1055 Kaupakalua Rd is listed for $3,950,000.00 and has been on the market for 25 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 | $3,950,000 |
| Bedrooms | 5 |
| Bathrooms | 3.00 |
| Square Footage | 4,550 |
| Land Tenure | Fee Simple |
| Acres | 16.03 |
| Year Built | 1975 |
| Type | Residential |
| Sub-Type | Single Family Residence |
| Status | Active |
| Property Tax | View Records |
| Short-Term Rental Allowed | No |
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 | 25 |
| Short Sale | No |
| RE / Bank Owned | No |
| Tax Map Key | 2270130500000 |
Listing Details
| Office | Hawaii Life (W) |
|---|
