1055 Kaupakalua Rd , Haiku

$ 3,950,000
1055 Kaupakalua Rd, Haiku, North Maui

Overview

  • 5
  • Bedrooms
  • 3
  • Bathrooms
  • 408773
  • MLS #
  • 16.0 ac
  • Lot Acres
  • 4,550.0 ft2
  • Living Area
  • 1975
  • Year Built:

Description

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.

Property Id: 5498297
Price: $ 3,950,000
Living Area: 4,550.0 ft2
Lot Acres: 16.0 ac
Bedrooms: 5
Bathrooms: 3
MLS ID: 408773
Last Updated: 02-16-2026 03:56 pm
Has Pool: Yes
View: Mountain/Ocean
Year Built: 1975
List Office Phone: 800-677-5028
List Office: Hawaii Life (W)
List Office Email: JeffSimon@HawaiiLife.com

Interior Details
Ceiling Fans
Dishwasher
Dryer
Furnished
Kitchen Ware
Microwave
Range
Refrigerator
Sauna
Solar Hot Water
Parking
No Garage
Pool
In Ground
Security
Wall Fence
Utilities
Public Water Src

Address: 1055 Kaupakalua Rd
City:
Zip: 96708

Transport
Supermarkets
Schools
Restaurants
Pharmacies
Hospitals

$ 19,834.55
per month
  • Principal and Interest
  • Property Tax
  • HOA fee
$ 18,945.80

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© REALTORS® Association of Maui, Inc. All Rights Reserved. This information is believed to be accurate. It has been provided by sources other than the Realtors Assoc. of Maui and should not be relied upon without independent verification. You should conduct your own investigation and consult with appropriate professionals to determine the accuracy of the information provided and to answer any questions concerning the property and structures located thereon. Featured properties may or may not be listed by the office/agent presenting this brochure. The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed.

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