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For sale
  • Price cut: $500K (9/2)
    $2,995,000

    1055 Kaupakalua Rd, Haiku, HI 96708

    5beds
    3baths
    4,550sqft
    : 
    $17,787/mo
    Get pre-qualified
    Single Family Residence, Residential
    Built in 1975
    16.03 Acres Lot
    $3,170,200 Zestimate®
    $658/sqft
    $-- HOA

    What's special

    Pool houseMassage pavilionFive bedroomsSpacious commercial-type kitchenExtensive landscaped grounds
    Set across 16 fully fenced and gated acres in Ha'iku, this expansive Maui estate offers privacy, substantial infrastructure, multiple structures, and considerable flexibility. The property is served by a County of Maui 5/8-inch water meter and a high-capacity well nearing completion, and is potentially subdividable subject to applicable County approvals. More than 20 varieties of mature exotic fruit trees and flowering plants are established throughout the grounds, with walking paths connecting the residences and amenities. At the center of the property is a 5,000+ square-foot main residence with five bedrooms, three bathrooms (two are large/bathhouse style), and a spacious commercial-type kitchen. The primary suite is surrounded by walls of glass overlooking the tropical landscape. The living room features a fireplace and concealed projection screen, while a large screened lanai provides additional space for dining and entertaining. A landscaped courtyard with a cascading waterfall and koi pond leads to trails winding throughout the property. A separate commercial-grade kitchen, adjoining screened gathering area, and dedicated men's and women's bathhouses reflect the property's history as a retreat destination and provide additional flexibility for larger gatherings. Additional structures include a two-room cottage currently used as an office, an upper guest cottage with a private outdoor shower house, and a separate two-story building tucked toward the rear of the acreage. These spaces provide options for guests, offices, studios, workshops, storage, or other uses. Outdoor amenities include a resort-style swimming pool with a waterfall and slide, pool house, massage pavilion, and extensive landscaped grounds. The estate is offered fully furnished, including more than $150,000 in furnishings, artwork, and antiques, with appraisals available. With 16 acres, multiple structures, established infrastructure, extensive landscaping, and potential subdivision opportunities, this Ha'iku property offers a range of possibilities as a private estate, multigenerational compound, creative retreat, or long-term Maui investment.
    23 days
    1,553
    143

    Zillow last checked:

    Listing updated:

    Listed 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

      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: 4,874
      • 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: $658/sqft
      • Tax assessed value: $3,223,300
      • Annual tax amount: $5,067
      • Date on market: 8/21/2026

        Estimated market value

        $3,170,200

        $3.01M - $3.33M

        $6,103/mo

        Price history

        DateEventPrice
        9/2/2026Price change$2,995,000-14.3%$658/sqft
        Source: RAM #408773 Report a problem
        8/21/2026Listed for sale$3,495,000-11.5%$768/sqft
        Source: RAM #408773 Report a problem
        6/2/2026Listing removed$3,950,000$868/sqft
        Source: RAM #408773 Report a problem
        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
        2025$5,067 +1%$3,223,300 +10.8%
        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

        Payment breakdown

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        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
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        Climate risks

        Neighborhood: 96708

        Getting around

        5 / 100
        Car-Dependent
        3 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating

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