Skip main navigation
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
    $3,615,700 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.
    57 days
    |
    970
    |
    58
    |

    Zillow last checked:

    Listing updated:

    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.
      Connect with an agentGet info on this home, tour, and more.
      Calculate monthly paymentSee if you can afford this home.

        Estimated market value

        $3,615,700

        $3.43M - $3.83M

        $5,156/mo

        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

        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

        Monthly payment

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

          Climate risks

          Neighborhood: 96708

          Getting around

          5 / 100
          Car-Dependent
          3 / 100
          Somewhat Bikeable

          Nearby schools

          GreatSchools rating

          A local agent can set up tours, give advice and negotiate with sellers.

          A local lender can help you make sure your offer is ready when you are.

          Browse local experts

          Similar homes

          Skip to the end of the carouselSkip to the beginning of the carousel