Wailea Highlands: Maui’s Most Exclusive Gated Enclave

Tucked atop a hillside near Hotel Wailea, Wailea Highlands is the most elite residential subdivision within the Wailea Resort. With just 24 generous homesites spread over approximately 14 to 14.5 acres, this private community offers unmatched elevation, sweeping ocean views, and enduring privacy—making it a trophy address for the discerning few. 

At a Glance: Wailea Highlands

• Location: Adjacent to Hotel Wailea, perched above the Wailea Blue Golf Course

• Community Size: 24 gated custom homesites on ~14–14.5 acres 

• Lot Sizes: Approximately 20,000 to 30,000 sq ft (nearly half-acre minimum) 

• Home Sizes: Typically 3,500 – 9,000 sq ft of customized luxury living 

• Entrance: Secure, gated access off Kaukahi Street or near Hotel Wailea

• Zoning: R-3 Residential—no short-term vacation rentals allowed 

• Notables Nearby: Wailea golf courses, The Shops at Wailea, Mokapu & Ulua beaches, Grand Wailea, Fairmont Kea Lani, Andaz Maui, and Wailea Beach Path

Hillside Homes, Million-Dollar Views

The elevated terrain of Wailea Highlands provides one of the most dramatic outlooks in the resort. Panoramic vistas span the Pacific Ocean, Moloka‘i, Lāna‘i, and the West Maui mountains, with rich sunset views and seasonal whale-watching right from your lanai. 

Homes are thoughtfully sited to preserve privacy and maximize scenic finishes. The mature landscaping, quiet cul-de-sacs, and architectural diversity—from modern retreats to island-inspired estates—lend the neighborhood a timeless elegance. 

Resort-Side Access, Elevated Living

Living at Wailea Highlands means enjoying effortless access to the best of Wailea without being in the thick of resort activity. Hit the fairways at Wailea Golf Club, stroll upscale shops and enjoy fine dining—with Ferraro’s, Nobu, Spago, or The Restaurant at Hotel Wailea just minutes away. Nearby beaches offer snorkeling, paddle boarding, and scenic walks along the Wailea Coastal Path. 

Why Wailea Highlands Stands Apart

• Prestige Rarity: With only 24 private homesites, properties here change hands infrequently, reinforcing its exclusive legacy status. 

• Generous Lot Sizes: The lots are among the largest in Wailea, offering both scale and golfing adjacency. 

• Custom Luxury: Architecturally distinctive homes, high-end finishes, pools, and open-living design are common. 

• Scenic Calm: Elevated position means quiet sanctuary with spectacular views. 

What Owners Love About Wailea Highlands

• Expansive Ocean & Island Views
  Panoramic vistas of Moloka‘i, Lāna‘i, and the Pacific define the daily experience. 

• Secluded Yet Accessible Location
  Elevated privacy that's minutes from top-tier golf, dining, and resort amenities.

• Large, Thoughtfully Designed Lots
  Generous spaces (20k–30k sq ft) ideal for privacy, gardens, or custom builds. 

• Legacy Neighborhood
  Limited turnover and longstanding ownership create an emotionally rooted, tight-knit community.

Exploring a Home Here?

If you're drawn to legacy living in Wailea and want a blend of seclusion, views, and thoughtful architecture, Wailea Highlands is rare and compelling. I can guide you through available inventory — both in MLS and private off-market options — to align your vision with what becomes available.

Considering a Sale in Wailea Highlands?

Marketing a property here requires meticulous presentation and a global stage. With Coldwell Banker Global Luxury, I deliver a boutique approach—from custom photography and storytelling brochures to luxury syndication and virtual showings that reach well-credentialed buyers worldwide.

King of the Hill

Wailea Highlands isn’t just a location—it's a legacy address in the truest sense. With its sweeping views, oversized lots, and quiet architecture, it offers a rare balance of prestige and peace. In this tiny gated enclave, the island’s natural elegance becomes your daily backdrop.