




1055 Kaupakalua Rd, Haiku, HI, 96708
Bedroom
5 Rooms
Bathroom
3 Baths
Square Foot
4550 Ft
Lot Size
16.03 Acres
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.
Contact Agent
Haiku Expert Agent
Additional Listing Details:
26 days on HouseJet
Last Refresh: 03/15/2026 06:00:03 PM UTC
MLS #: 408773
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.
Agents: Is This Your Listing?
2958 SW REDMOND HILL Rd, McMinnville, OR, 97128
1315 SW DOROTHY St, McMinnville, OR, 97128
1535 NW Tracy, McMinnville, OR, 97128
1518 NW Tracy St, McMinnville, OR, 97128
Listing Agent
Josh Jerman
License # RB-19728
Hawaii Life Real Estate Brokers
Phone: 800-370-3848