About This Home

This 5-bedroom, 3-bathroom single family at 1055 Kaupakalua Rd in Haiku, HI is listed for $2,995,000 ($658 per sqft). the home offers 4,550 sqft of living space on a 16.03 acres lot.

Key Features

  • 16.03 acre lot

Property Details

3 full

Amenities

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Listing 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.

Monthly Cost Estimate

$16,018/mo

20% down · 6.5% · 30 years

Principal$2,166
Interest$12,978
Insurance$874

Estimates only. Actual payments may vary.

Location

1055 Kaupakalua Rd

Haiku, HI 96708

Property Details

Views

Ocean

Questions & Answers

This 5-bedroom, 3-bathroom single family at 1055 Kaupakalua Rd is listed at $2,995,000 ($658/sqft). The estimated monthly payment is $16,018 based on 20% down, a 30-year loan at 6.5% interest, estimated insurance.

Key features include: 16.03 acre lot.

This property is listed by Josh Jerman.

JJ

Josh Jerman

Agent at Hawaii Life Real Estate Brokers

Listed by Hawaii Life Real Estate Brokers · Broker phone: (800) 370-3848 · View on Broker Site · Broker website

MLS# 408773· Source: Realtors ® Association of Maui, Inc.· 257 days on PropertySimple

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.

1055 Kaupakalua Rd, Haiku, HI 96708

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