# 1055 Kaupakalua Rd, Haiku, HI 96708

> **TL;DR:** 5bd/3ba single family, $2,995,000 ($658/sqft), 4,550 sqft.
> View. Est. $16,018/mo. Listed 259 days.

## Property at a Glance

| Attribute | Value |
|-----------|-------|
| Price | $2,995,000 |
| Price/sqft | $658 |
| Bedrooms | 5 |
| Bathrooms | 3 full |
| Square Feet | 4,550 |
| Lot Size | 698,397 sqft (16.03 acres) |
| Property Type | Single Family (Other) |
| Status | Pending |
| Days on Market | 259 |

## Why This Home Stands Out

- **Views** - Ocean

## Estimated Monthly Costs

| Category | Amount |
|----------|--------|
| Principal & Interest (20% down, 30-year at 6.5%) | $15,144 |
| Estimated Insurance | $874 |
| **Total** | **$16,018** |

## Key Amenities

- View

## Property Highlights

- 16.03 acre lot

## Description

### Agent Description
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.

## Location

- **Address:** 1055 Kaupakalua Rd, Haiku, HI 96708
- **Coordinates:** 20.901768, -156.286898
- **Google Maps:** https://www.google.com/maps?q=20.901768,-156.286898

## Virtual Tour & Media

- **Video Tour:** https://player.vimeo.com/video/1169637989

## Listing Agent

- **Name:** Josh Jerman
- **Brokerage:** Hawaii Life Real Estate Brokers
- **Broker Phone:** (800) 370-3848
- **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/1055-Kaupakalua-Rd_Haiku_HI_96708_M86401-50345?f=listhub&s=RAMHI&m=408773&c=propsimple)

## Photos

![1055 Kaupakalua Rd - Photo 1](http://lh.rdcpix.com/03bee7be8ff29f2ded312f12f63729b9l-f3598245487r.jpg)

![1055 Kaupakalua Rd - Photo 2](http://lh.rdcpix.com/03bee7be8ff29f2ded312f12f63729b9l-f2435536452r.jpg)

![1055 Kaupakalua Rd - Photo 3](http://lh.rdcpix.com/03bee7be8ff29f2ded312f12f63729b9l-f332728004r.jpg)

![1055 Kaupakalua Rd - Photo 4](http://lh.rdcpix.com/03bee7be8ff29f2ded312f12f63729b9l-f3720562369r.jpg)

![1055 Kaupakalua Rd - Photo 5](http://lh.rdcpix.com/03bee7be8ff29f2ded312f12f63729b9l-f1526268509r.jpg)

![1055 Kaupakalua Rd - Photo 6](http://lh.rdcpix.com/03bee7be8ff29f2ded312f12f63729b9l-f3152006670r.jpg)

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![1055 Kaupakalua Rd - Photo 34](http://lh.rdcpix.com/03bee7be8ff29f2ded312f12f63729b9l-f1769656421r.jpg)

![1055 Kaupakalua Rd - Photo 35](http://lh.rdcpix.com/03bee7be8ff29f2ded312f12f63729b9l-f477899407r.jpg)

![1055 Kaupakalua Rd - Photo 36](http://lh.rdcpix.com/03bee7be8ff29f2ded312f12f63729b9l-f1015125323r.jpg)

![1055 Kaupakalua Rd - Photo 37](http://lh.rdcpix.com/03bee7be8ff29f2ded312f12f63729b9l-f4150122422r.jpg)

![1055 Kaupakalua Rd - Photo 38](http://lh.rdcpix.com/03bee7be8ff29f2ded312f12f63729b9l-f1815505716r.jpg)

![1055 Kaupakalua Rd - Photo 39](http://lh.rdcpix.com/03bee7be8ff29f2ded312f12f63729b9l-f1814069612r.jpg)

![1055 Kaupakalua Rd - Photo 40](http://lh.rdcpix.com/03bee7be8ff29f2ded312f12f63729b9l-f447400049r.jpg)

![1055 Kaupakalua Rd - Photo 41](http://lh.rdcpix.com/03bee7be8ff29f2ded312f12f63729b9l-f701584796r.jpg)

![1055 Kaupakalua Rd - Photo 42](http://lh.rdcpix.com/03bee7be8ff29f2ded312f12f63729b9l-f877068041r.jpg)

![1055 Kaupakalua Rd - Photo 43](http://lh.rdcpix.com/03bee7be8ff29f2ded312f12f63729b9l-f1318850868r.jpg)

![1055 Kaupakalua Rd - Photo 44](http://lh.rdcpix.com/03bee7be8ff29f2ded312f12f63729b9l-f3067517548r.jpg)

![1055 Kaupakalua Rd - Photo 45](http://lh.rdcpix.com/03bee7be8ff29f2ded312f12f63729b9l-f3973913264r.jpg)

![1055 Kaupakalua Rd - Photo 46](http://lh.rdcpix.com/03bee7be8ff29f2ded312f12f63729b9l-f3063065413r.jpg)

![1055 Kaupakalua Rd - Photo 47](http://lh.rdcpix.com/03bee7be8ff29f2ded312f12f63729b9l-f2640128498r.jpg)

![1055 Kaupakalua Rd - Photo 48](http://lh.rdcpix.com/03bee7be8ff29f2ded312f12f63729b9l-f999675503r.jpg)

![1055 Kaupakalua Rd - Photo 49](http://lh.rdcpix.com/03bee7be8ff29f2ded312f12f63729b9l-f1115002345r.jpg)

![1055 Kaupakalua Rd - Photo 50](http://lh.rdcpix.com/03bee7be8ff29f2ded312f12f63729b9l-f2703157721r.jpg)

---

**MLS#:** 408773 | **Updated:** 2026-10-31
**Source:** listhub

*Copyright © 2026 Realtors ® Association of Maui, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.*

[View on PropertySimple](https://www.propertysimple.ai/listing/1055-kaupakalua-rd-haiku-hi-96708-a9d0c5a39db240f7af0c7ff048daec3e)

---

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