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For sale
  • $3,950,000

    1055 Kaupakalua Rd, Haiku, HI 96708

    5beds
    3baths
    4,550sqft
    : 
    Single Family Residence, Residential
    Built in 1975
    16.03 Acres Lot
    $3,040,800 Zestimate®
    $868/sqft
    $-- HOA

    What's special

    Accompanying pool houseTranquil massage pavilionPrivate expansive
    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.
    6 days
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    1,259
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    66
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    Zillow last checked: 8 hours ago

    Listing updated: February 16, 2026 at 04:23pm

    Listing Provided by:

    Josh Jerman RB-19728 Cell:808-283-2222,

    Hawaii Life (W),

    Tim Stice RB-21556 808-268-8511,

    Hawaii Life (W)

    Source: RAM,MLS#: 408773MLS Logo

    Tour with a local agent

    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 5
    • Bathrooms: 3
    Primary bedroom
    • Level: Ground
    Appliances
    • Included: Dishwasher, Dryer, Microwave, Range, Refrigerator, Solar Hot Water
    Features
    • Ceiling Fan(s), Kitchen Ware, Sauna
    • Has fireplace: Yes
    • Furnished: Yes
    Interior area
    • Total structure area: 4,550
    • Total interior livable area: 4,550 sqft

    Property

    Parking
    • Parking features: No Garage
    Features
    • Levels: One
    • Stories: 1
    • Has private pool: Yes
    • Pool features: In Ground
    • Fencing: Wall/Fence
    • Has view: Yes
    • View description: Mountain/Ocean
    • Has water view: Yes
    • Water view: Mountain/Ocean
    • Waterfront features: None
    Lot
    • Size: 16.03 Acres
    Details
    • Parcel number: 2270130500000

    Construction

    Type & style
    • Home type: SingleFamily
    • Property subtype: Single Family Residence, Residential
    Condition
    • Year built: 1975

    Utilities & green energy

    • Water: Public

    Community & HOA

    Location
    • Region: Haiku

    Financial & listing details

    • Price per square foot: $868/sqft
    • Tax assessed value: $2,909,200
    • Annual tax amount: $5,018
    • Date on market: 2/17/2026
    Get pre-qualifiedBe ready to make an offer.
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    Estimated market value

    $3,040,800

    $2.40M - $3.80M

    $3,010/mo

    Price history

    Price history
    DateEventPrice
    2/17/2026Listed for sale$3,950,000+86.8%$868/sqft
    Source: RAM #408773 Report a problem
    8/20/2019Sold$2,115,000+1.9%$465/sqft
    Source: RAM #382284 Report a problem
    7/29/2003Sold$2,075,000$456/sqft
    Source: Public Record Report a problem

    Public tax history

    Public tax history
    YearProperty taxesTax assessment
    2024$5,018 +10.5%$2,909,200 +11%
    2023$4,540 +6%$2,620,100 +14.5%
    2022$4,284 -11.1%$2,287,400 +8%
    2021$4,819 -47.2%$2,118,400 +4.9%
    2020$9,134 -2.3%$2,019,000 +31.3%
    2019$9,349 $1,537,700 -1.3%
    2018$9,349 +26.2%$1,558,200
    2017$7,410 +7%--
    2016$6,927 $1,223,900 +6.3%
    2015-- $1,151,900

    Find assessor info on the county website

    BuyAbility℠ payment

    Est. payment
    $20,864/mo
    Principal & interest
    $20370
    Property taxes
    $494

      Climate risks

      Neighborhood: 96708

      Nearby schools

      GreatSchools rating

      Local experts in 96708

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