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.
For sale
$5,000,000
557 Kupulau Dr, Kihei, HI 96753
4beds
4baths
3,447sqft
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
- 98 days
- 919
- 60
Zillow last checked:
Listing updated:
Listed by:
Todd J. Hudson RB-21913 Cell:808-344-3584,
Keller Williams Realty Maui-Ki
Source: RAM,MLS#: 409679
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
Video & virtual tour
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
| Date | Event | Price |
|---|---|---|
| 5/22/2026 | Listed for sale | $5,000,000+189.9%$1,451/sqft |
Source: | ||
| 12/2/2019 | Sold | $1,725,000+7.9%$500/sqft |
Source: | ||
| 10/4/2019 | Pending sale | $1,599,000$464/sqft |
Source: Maui Luxury Real Estate LLC #384378 Report a problem | ||
| 9/27/2019 | Listed for sale | $1,599,000+27.9%$464/sqft |
Source: Maui Luxury Real Estate LLC #384378 Report a problem | ||
| 12/30/2013 | Sold | $1,250,000+13.6%$363/sqft |
Source: Public Record Report a problem | ||
| 1/11/2006 | Sold | $1,100,000+96.4%$319/sqft |
Source: Public Record Report a problem | ||
| 12/23/2002 | Sold | $560,000$162/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax 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




