Discover Wailea Highlands
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Luxury homes for Sale in Wailea Highlands, Wailea, HI
Wailea Highlands stands as a pinnacle of residential luxury within the world-renowned Wailea Resort, offering an unparalleled level of privacy and prestige. As the boutique gated community in Wailea, this enclave consists of only 24 homesites sprawling across approximately 14.5 acres of prime hillside real estate. Because the neighborhood features the most extensive land cuts in the area, residents enjoy a sense of space and seclusion that is rare in resort living. The topography of the land is a defining characteristic, as the neighborhood is perched on a hillside that offers some of the steepest gradient views in South Maui.
From these elevated vantage points, homeowners are treated to sweeping, unobstructed panoramas of the Pacific Ocean, framed by the West Maui Mountains and the distant silhouettes of Molokini and Lanai. This exclusive gated community Wailea residents call home is bordered by the manicured fairways of the Wailea Blue Golf Course and is just a short stroll from the prestigious Hotel Wailea. Here, the focus is on individuality; unlike other developments with uniform designs, this neighborhood is comprised entirely of custom luxury estates, each reflecting the unique architectural vision of its owner. For those seeking Wailea Highlands homes for sale, the combination of massive half-acre lots and high-elevation perspectives creates an environment of quiet elegance and island sophistication.
Top Reasons to Buy in Wailea Highlands, Wailea, HI
Unrivaled Privacy and Exclusivity
Living in the boutique gated community in Wailea offers a level of intimacy and security that larger developments simply cannot match. With only 24 total lots, the neighborhood feels like a private sanctuary where neighbors value peace and quiet above all else. The gated entrance is strictly monitored to ensure that only residents and invited guests enter, maintaining the tranquil atmosphere of the hillside. Because these properties do not frequently change hands, acquiring a home here places you in a very select circle of South Maui homeowners.
Massive Estate-Sized Lots
While many resort communities in Maui utilize smaller lot footprints to maximize density, Wailea Highlands is known for having the largest land cuts in the resort. Most lots range from 20,000 to over 30,000 square feet, which is roughly double the size of the typical surrounding parcels. This extra space allows for sprawling single-level or multi-story floor plans that accommodate expansive lanais, private botanical gardens, and infinity-edge pools. The generous setbacks between homes ensure that your outdoor living spaces remain entirely private and unencumbered by neighboring structures.
Commanding Elevation and Ocean Vistas
The community’s location at the top of the Wailea resort provides a geographical advantage, resulting in some of the most dramatic views on the island. Due to the natural slope of the terrain, homes are tiered in a way that protects the view corridors of the properties behind them. You can spend your evenings watching the sunset over the “Auʻau Channel or spotting humpback whales during the winter months directly from your living room. The elevation also invites refreshing trade winds that naturally cool the homes, providing a comfortable climate year-round.
Wailea Highlands, Wailea, HI Real Estate Snapshot
- Price Range: Homes in this community typically range from $4,500,000 to $11,000,000, depending on the age of the structure and the directness of the ocean view.
- Typical Year Built: Development in the neighborhood began in the late 1990s, with most homes constructed between 1999 and 2005, though many have undergone significant modern renovations.
- Interior Square Footage: Residences are generously sized, typically ranging from 3,500 to over 9,000 square feet of living space.
- Lot Sizes: This community is distinguished by its large parcels, with average lot sizes hovering around 0.50 to 0.70 acres.
- Market Trend: The neighborhood is zoned R-3 Residential, which strictly prohibits short-term vacation rentals, ensuring a consistent and quiet residential atmosphere for long-term owners.
DEMOGRAPHICS
Who Lives in Wailea/Makena
ENTERTAINMENT
Things to do around Wailea Highlands
The Shops at Wailea
An upscale open-air center featuring luxury boutiques, local art galleries, and premier island dining.
Wailea Blue Golf Course
Known as the "Grand Lady of Wailea," this scenic course borders the community with lush fairways.
Wailea Beach
A world-class crescent of golden sand perfect for swimming, snorkeling, and sunset walks.
Hotel Wailea, Relais & Châteaux
An ultra-luxury adults-only retreat located adjacent to the community offering fine dining at The Restaurant.
SCHOOLS
Schools near Wailea Highlands
ON THE MAP
Wailea Highlands on the Map
To reach the community from Kahului Airport (OGG), head south on the Pi’ilani Highway (Highway 31) for approximately 14 miles until the road terminates into Wailea Ike Drive. Turn left onto Wailea Ike Drive, then make another right onto Kalai Waa St. then turn left on onto Kaukahi Street; follow the road down and you will find the gated entrance to the Highlands on your right-hand side.