1055 Kaupakalua Rd, Haiku, HI

$3,950,000

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5

Beds

3

Baths

4,550

Square feet

16.03

Acres

About 1055 Kaupakalua Rd

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.

Features of 1055 Kaupakalua Rd

MLS® # 408773
Price $3,950,000
Bedrooms 5
Bathrooms 3.00
Square Footage 4,550
Land Tenure Fee Simple
Acres 16.03
Year Built 1975
Status Active

Additional Information

Date Listed February 16th, 2026
Days on Market 21
Land Tenure Fee Simple
Short Sale No
RE / Bank Owned No

Community Information

Address 1055 Kaupakalua Rd
City Haiku
State HI
Zip Code 96708

Amenities

Short Term Rental Allowed No
View Mountain/Ocean
Is Waterfront No
Waterfront None
Has Pool Yes

Interior

Interior Features Ceiling Fan(s), Furnished, Kitchen Ware, Sauna
Appliances Dishwasher, Dryer, Microwave, Range, Refrigerator, Solar Hot Water
Fireplace Yes
Stories One

Listing Details

OfficeHawaii Life (W)
Contact InfoCell: 808-283-2222

Listing Map

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