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For sale
  • $5,000,000

    557 Kupulau Dr, Kihei, HI 96753

    4beds
    4baths
    3,447sqft
    : 
    $28,459/mo
    Get pre-qualified
    Single Family Residence, Residential
    Built in 1972
    0.57 Acres Lot
    $4,495,100 Zestimate®
    $1,451/sqft
    $-- HOA

    What's special

    Panoramic ocean viewsLush tropical landscapingUnforgettable sunsetsElegant finishesOpen-concept designPositioned above the coastlineExpansive indoor-outdoor living spaces
    Welcome to the Resort in Maui Meadows — an extraordinary private estate where jaw-dropping panoramic ocean views, unforgettable sunsets, and elevated island living converge in one of South Maui’s most coveted neighborhoods. Perfectly positioned above the coastline, this exceptional residence captures sweeping vistas stretching across the Pacific Ocean to the neighboring islands, creating a breathtaking backdrop from nearly every room. By day, enjoy sparkling turquoise waters and endless horizon views; by evening, experience Maui’s legendary sunsets illuminating the sky in spectacular color. Designed to live like a private luxury resort, the property is an entertainer’s dream. Expansive indoor-outdoor living spaces flow seamlessly onto oversized lanais and gathering areas curated for unforgettable sunset dinners, cocktail parties, celebrations, and relaxed evenings beneath the stars. The open-concept design invites effortless hosting while maximizing the stunning ocean vistas and cooling island trade winds throughout the home. The chef’s kitchen anchors the residence with premium appliances, generous prep and serving areas, and elegant finishes designed for both intimate dining and large-scale entertaining. Spacious guest accommodations provide comfort and privacy for family and friends, while the primary suite offers a tranquil retreat with spa-inspired luxury and mesmerizing ocean views. Surrounded by lush tropical landscaping and an atmosphere of complete serenity, the Resort in Maui Meadows delivers a rare sense of escape while remaining just moments from Wailea’s world-class beaches, golf courses, fine dining, and luxury resorts. This is more than a home — it is a destination, a retreat, and a lifestyle defined by breathtaking beauty, privacy, and unforgettable entertaining in the heart of South Maui.
    96 days
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    949
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    73
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    Zillow last checked:

    Listing updated:

    Listed by:

    Todd J. Hudson RB-21913 Cell:808-344-3584,

    Keller Williams Realty Maui-Ki

    Source: RAM,MLS#: 409679MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 4
      Primary bedroom
      • Level: Ground
      Appliances
      • Included: Dishwasher, Disposal, Dryer, Microwave, Range, Refrigerator, Solar Hot Water, Washer
      Features
      • Ceiling Fan(s), Storage, Remodeled
      • Windows: Blinds
      • Has basement: Yes
      • Has fireplace: No
      Interior area
      • Total structure area: 4,143
      • Total interior livable area: 3,447 sqft

      Property

      Parking
      • Total spaces: 4
      • Parking features: Garage, Garage Door Opener
      • Garage spaces: 4
      Features
      • Levels: One
      • Stories: 1
      • Exterior features: Lawn Sprinkler
      • Has private pool: Yes
      • Pool features: Above Ground
      • Spa features: Spa/Hot Tub
      • Has view: Yes
      • View description: Ocean
      • Has water view: Yes
      • Water view: Ocean
      • Waterfront features: None
      Lot
      • Size: 0.57 Acres
      Details
      • Parcel number: 2210151030000

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Single Family Residence, Residential
      Condition
      • Year built: 1972
      • Major remodel year: 2022

      Utilities & green energy

      • Electric: Photovoltaics Seller Owned, Underground
      • Sewer: Septic Tank
      • Water: Public
      • Utilities for property: Phone Connected, Cable Connected, Telephone, TV Cable
      Green energy
      • Energy generation: Solar

      Community & HOA

      Community
      • Security: Smoke Detector(s)
      • Subdivision: Maui Meadows
      Location
      • Region: Kihei

      Financial & listing details

      • Price per square foot: $1,451/sqft
      • Tax assessed value: $2,867,000
      • Annual tax amount: $4,425
      • Date on market: 5/22/2026
      • Electric utility on property: Yes

        Estimated market value

        $4,495,100

        $4.27M - $4.72M

        $7,961/mo

        Price history

        DateEventPrice
        5/22/2026Listed for sale$5,000,000+189.9%$1,451/sqft
        Source: RAM #409679 Report a problem
        12/2/2019Sold$1,725,000+7.9%$500/sqft
        Source: RAM #384378 Report a problem
        10/4/2019Pending sale$1,599,000$464/sqft
        Source: Maui Luxury Real Estate LLC #384378 Report a problem
        9/27/2019Listed for sale$1,599,000+27.9%$464/sqft
        Source: Maui Luxury Real Estate LLC #384378 Report a problem
        12/30/2013Sold$1,250,000+13.6%$363/sqft
        Source: Public Record Report a problem
        1/11/2006Sold$1,100,000+96.4%$319/sqft
        Source: Public Record Report a problem
        12/23/2002Sold$560,000$162/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$4,426 +9.2%$2,867,000 +18.1%
        2024$4,054 +22.9%$2,426,900 +21.4%
        2023$3,298 +19%$1,998,900 +27.6%
        2022$2,770 -12.3%$1,566,800 +5.1%
        2021$3,158 +13.4%$1,490,100 +0.9%
        2020$2,785 -60.6%$1,477,500 +27.3%
        2019$7,069 $1,160,200 -1.5%
        2018$7,069 +6.7%$1,178,100
        2017$6,624 +183.4%--
        2016$2,337 $1,065,600 +0.9%
        2015-- $1,056,300
        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: 96753

        Getting around

        16 / 100
        Car-Dependent
        14 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating

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