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557 Kupulau Dr, Kihei, HI 96753
$5,000,000
Home
for sale
4 beds
4 baths
3,447 sqft
Neighborhood:
Kihei
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.
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Home details
3,447 sqft interior area
- Year Built 1972
- Year Remodeled 2022
- Original list price $5,000,000
- Days on market 2
- Price per sqft $1,451/sqft
- Baths 4
- Beds 4
-
Address
557 Kupulau Dr, Kihei, HI, 96753
- Total area 3,447 sqft
- Interior area 3,447 sqft
- Land area 24,916 sqft
- nr.of parking places 4
- Frontage None
- Pool Above Ground
- Neighborhood Kihei | Maui Meadows
- City of Maui Kihei
- Region Maui Meadows
- Island Maui
- View Ocean
- Virtual Tour View (external link)
Open Houses
No upcoming open houses
Monthly payment
Calculate your monthly payments
Mortgage
$25,494
Taxes
$4,426
HOA dues
$0
Mortgage
Down payment
$1,000,000 / 20%
Interest rate
6.58%
Loan type
30 years
Your amount
$25,494 / month
Neighborhood: Kihei
Nearby & commute
Walkability
Coffee shops
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no data
Bus stop
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no data
Supermarket
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no data
Costco
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no data
Hospital
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no data
Park
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no data
Beach
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no data
Elementary school
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no data
Middle school
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no data
High school
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no data
Local airport
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no data
4.67 / 20
Car dependent
►
18-20
Most Walkable
15-18
Very walkable
10-15
Somewhat walkable
1-10
Car dependent
Walkability according to the National Walkability Index
Ohana
Ohana design
County Water, Telephone, TV Cable, Underground Electric
Ohana utilities on site
County Water, Telephone, TV Cable, Underground Electric
Amenities & Features
4 parking places
Utilities
Public, Photovoltaics Seller Owned, Underground
Kihei prices
Average price $551.6k
Neighborhood average sales price*
$551.6k
Neighborhood median sales price*
$575k
Number or sales*
45
Street median sales price*
$586.5k
*last 6 months
Schools
15 schools in this area
| School rating | Distance | |
|---|---|---|
|
Kamalii Elementary School
180 Kealii Alanui,
Kihei, HI 96753
Elementary School
|
1.509mi | |
|
Lokelani Intermediate School
1401 Liloa Dr,
Kihei, HI 96753
Middle School
|
3.261mi | |
|
Kahuahana Christian School
Po Box 532554,
Kihei, HI 96753
High School
|
4.339mi |
| School rating | Distance | |
|---|---|---|
|
Kamalii Elementary School
180 Kealii Alanui,
Kihei, HI 96753
|
1.509mi | |
|
Kihei Elementary School
250 East Lipoa St,
Kihei, HI 96753
|
3.372mi | |
|
Montessori Hale O Keiki
100 Kulanihakoi St,
Kihei, HI 96753
|
4.339mi | |
|
Kahuahana Christian School
Po Box 532554,
Kihei, HI 96753
|
4.339mi | |
|
Kihei Public Charter School
300 Ohukai Rd,
Kihei, HI 96753
|
5.07mi |
| School rating | Distance | |
|---|---|---|
|
Lokelani Intermediate School
1401 Liloa Dr,
Kihei, HI 96753
|
3.261mi | |
|
Montessori Hale O Keiki
100 Kulanihakoi St,
Kihei, HI 96753
|
4.339mi | |
|
Kahuahana Christian School
Po Box 532554,
Kihei, HI 96753
|
4.339mi | |
|
Kihei Public Charter School
300 Ohukai Rd,
Kihei, HI 96753
|
5.07mi | |
|
Haleakala Waldorf School
4160 Lower Kula Road,
Kula, HI 96790
|
7.912mi |
| School rating | Distance | |
|---|---|---|
|
Kahuahana Christian School
Po Box 532554,
Kihei, HI 96753
|
4.339mi | |
|
Kihei Public Charter School
300 Ohukai Rd,
Kihei, HI 96753
|
5.07mi | |
|
Kamehameha Schools Maui
270 Aapueo Parkway,
Makawao, HI 96768
|
10.323mi | |
|
King Kekaulike High School
121 Kula Hwy,
Pukalani, HI 96768
|
10.894mi | |
|
Maui High School
660 South Lono Ave,
Kahului, HI 96732
|
12.171mi |
School ratings provided by Greatschools.org
© 2023. All rights reserved.
Price history
New Listing May 22, 2026
| Date | Event | Price | $/sqft | Source |
|---|---|---|---|---|
| May 22, 2026 | New Listing | $5,000,000 +189.86% | $1,450.54 | MLS #409679 |
| Dec 2, 2019 | Sold | $1,725,000 +7.88% from last sold price | $500.44 | Public Record |
| Oct 4, 2019 | Pending | $1,599,000 | $463.88 | MLS #384378 |
| Sep 27, 2019 | New Listing | $1,599,000 +147.91% | $463.88 | MLS #384378 |
| Dec 23, 2002 | Sold | $560,000 | $162.46 | Public Record |
| Jan 1, 2002 | Expired | $645,000 | $187.12 | MLS #2103242 |
| May 27, 2001 | Price Decrease | $645,000 -7.19% | $187.12 | MLS #2103242 |
| Mar 31, 2001 | New Listing | $695,000 +24.11% | $201.62 | MLS #2103242 |
Tax & MLS details 557 Kupulau Dr, Kihei, HI, 96753
MLS #409679
Current Property Taxes p/month
$4,426
Property Tax Year
2025
TMK
2210151030000
Listed by
Keller Williams Realty Maui-Ki
Cell: 808-344-3584
Cell: 808-344-3584
MLS #
409679
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Frequently asked questions for 557 Kupulau Dr
What is 557 Kupulau Dr?
557 Kupulau Dr, Kihei, HI, 96753 is a single family home located in the Kihei neighborhood of the Maui Meadows region in the city of Kihei in zipcode 96753. This single family home has 4 bedrooms & 4 bathrooms with an interior area of 3447 sqft, on a 24916 sqft lot.
When was this home built and last sold?
This house was build in 1972.
What is the full address of this home?
557 Kupulau Dr, Kihei, HI, 96753.
Are there beaches near 557 Kupulau Dr?
No, there aren't.
Based on information from the Realtors Assoc. of Maui. Copyright 2026 by REALTORS® Association of Maui, Inc. Listing courtesy of Keller Williams Realty Maui-Ki. This information is believed to be accurate. It has been provided by sources other than the Realtors Assoc. of Maui and should not be relied upon without independent verification. You should conduct your own investigation and consult with appropriate professionals to determine the accuracy of the information provided and to answer any questions concerning the property and structures located thereon. Featured properties may or may not be listed by the office/agent presenting this brochure.
Listings last updated on May 22, 2026.
Hawaii House Last checked 2 years ago.
557 Kupulau Dr, Kihei, HI, 96753 is a single family home located in the Kihei neighborhood
of the Maui Meadows region in the city of Kihei in zipcode 96753.
This single family home has 4 bedrooms &
4 bathrooms with an interior area of 3447 sqft,
on a 24916 sqft lot. This house was build in 1972.
*Neighborhood & street median sales price are calculated over sold properties over the last 6 months.
Kihei & nearby Neighborhoods
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