Skip to main contentSkip to navigation
1 / 46
Images
Map
Street

Land with Home for Sale in Haʻikū, Hawaii

1055 Kaupakalua Rd, Haʻikū, HI 96708

$3,950,000
16 acres
Active
ago
Est $20,243/mo

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.

4,550
Sq feet
5
Beds
3
Full baths

Location

Street address
1055 Kaupakalua Rd
Elevation
908 feet
Coordinates
20.9004, -156.2866

Property details

Acreage
16.033 acres
MLS #
RAM 408773
Posted

Parcels

  • 227013050

Details and features

Listing

Type
Residential
Subtype
Single Family Residence

Lot

View
Mountain, Ocean

Interior

Rooms
Bathroom x 3, Bedroom x 5

Listing history

DateEventPriceChangeSource
Feb 17, 2026New listing$3,950,000RAM
Subscribe to listing updates

Payment calculator

This 16.033-acre property is located at 1055 Kaupakalua Rd in Haʻikū, HI 96708. The property is available for sale for $3,950,000. It has a 4,550 sq ft 5 bedroom, 3 bath house.

Checked 2 hours ago — Updated

Report listing issue

Copyright (C) 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.

Contact listing agent Rules
By submitting, I agree to the terms of use and to be contacted by real estate professionals. Message and data rates may apply.
Contact