Wailea’s Finest: A Guide to Maui’s Most Sought-After Communities

In Wailea, luxury living comes with a view — whether that’s the sparkle of the Pacific, a swath of emerald fairway, or a sunset framed by neighboring islands. This South Maui resort area blends world-class beaches, five-star resorts, championship golf, and refined dining with residential communities that cater to a range of lifestyles.

From modern townhomes to beachfront condos and gated estates, each neighborhood in Wailea has its own character — and its own devoted following. Here’s a closer look at some of the area’s most desirable addresses.

Kai Malu – Townhome Living with Resort Perks

What makes it unique
Kai Malu offers the rare combination of spacious townhome living and resort-style amenities in the heart of Wailea. This gated community is prized for its two-story floor plans, attached garages, and private yards — all while enjoying access to a stunning infinity-edge pool overlooking the ocean, a fitness center, sauna, and community pavilion. It’s designed for a low-maintenance lifestyle without sacrificing privacy or comfort.

Proximity to amenities

• Golf – Located along the Wailea Blue Golf Course, with quick access to Wailea’s other championship courses.

• Shopping & Dining – Just minutes to The Shops at Wailea and restaurants like Lineage, Wolfgang Puck, and Ruth’s Chris.

• Beaches – A short drive to Wailea Beach, Ulua Beach, and Mokapu Beach.

• Resorts – Near The Grand Wailea and Andaz Maui for spa treatments, dining, and events.

Basic facts

• Type: Gated townhome community

• Number of Residences: 150

• Layouts: Two-story, 3-bed / 3.5-bath floor plans (~1,750–1,850 sq ft)

• Views: Golf course, ocean, mountain, and garden views

• HOA: Covers common areas, landscaping, pool, spa, and security

12 Month Sales Activity

• Active (at time of writing): 1
• Pending: 1
• Sold: 7
• Average Sales Price: $2,780,357

🔗Kai Malu Listings and Info

Makali‘i – Contemporary Style with an Ocean View

What makes it unique
Makali‘i stands out for its sleek, modern architecture — a rare contemporary aesthetic in Wailea. These luxury townhomes feature high ceilings, floor-to-ceiling glass, and expansive lanais to maximize natural light and ocean views. The centerpiece of the community is the elevated clubhouse, complete with a fitness center, infinity pool, and panoramic ocean vistas.

Proximity to amenities

• Beaches – Across from Polo Beach and just down the hill from Wailea Beach Path.

• Shopping & Dining – Minutes to The Shops at Wailea and fine dining like Spago and Ferraro’s at Four Seasons.

• Golf & Tennis – Close to Wailea Gold and Emerald Golf Courses as well as Wailea Tennis Club.

Basic facts

• Type: Gated luxury townhome community

• Number of Residences: 68

• Layouts: 2- to 3-bedroom residences with ~1,500–1,800 sq ft interiors plus generous lanais

• Views: Primarily ocean and sunset views

• HOA: Includes clubhouse, pool, landscaping, and security

12 Month Sales Activity

• Active (at time of writing): 3
• Pending: 0
• Sold: 4
• Average Sales Price: $3,161,250

🔗Makali'i Listings and Info

Wailea Elua – True Beachfront Bliss

What makes it unique
Wailea Elua is one of the rare true beachfront condo communities in Wailea. With 24 acres of lush tropical landscaping, direct access to Ulua Beach, and low-rise buildings spread generously across the property, it offers a private, uncrowded feel. Its oceanfront pool pavilion is a favorite gathering spot for sunsets and beachside barbecues.

Proximity to amenities

• Beaches – Direct access to Ulua Beach and the Wailea Beach Path.

• Shopping & Dining – Short walk to The Shops at Wailea and restaurants like Tommy Bahama and Waikomo Shave Ice.

• Golf – Adjacent to Wailea Blue Golf Course and minutes to the Gold and Emerald Courses.

Basic facts

• Type: Gated beachfront condominium community

• Number of Residences: 152

• Layouts: 1- to 3-bedroom floor plans (891–1,749 sq ft)

• Views: Oceanfront, ocean view, and garden view

• HOA: Includes pools, fitness center, security, and landscaping

12 Month Sales Activity

• Active (at time of writing): 5
• Pending: 0
• Sold: 1
• Average Sales Price: $4,465,000

🔗Wailea Elua Listings and Info

Wailea Kai-Walk To It All

What makes it unique
Wailea Kai blends the charm of an established neighborhood with the convenience of resort living. As one of Wailea’s original planned communities, it’s known for mature landscaping, tree-lined streets, and a welcoming, walkable layout. The real standout feature is its location and access to Keawakapu Beach — one of Maui’s most beloved stretches of sand — making early morning swims or sunset strolls an effortless part of daily life.

Proximity to amenities
Residents of Wailea Kai enjoy one of the most central locations in Wailea:

• Beaches – Across the street access to Keawakapu Beach; minutes to Mokapu and Ulua Beaches.

• Shopping & Dining – Less than five minutes to The Shops at Wailea, featuring fine dining at Tommy Bahama, Ruth’s Chris Steak House, and boutique shopping.

• Golf & Tennis – Quick access to Wailea’s three championship golf courses and Wailea Tennis Club.

• Resorts – A short drive to Andaz Maui, Wailea Beach Resort, and other five-star properties for spa days or special dinners.

Basic facts

• Type: Gated single-family residential community

• Number of Homesites: 100+

• Lot Sizes: Approximately 7,500 to 12,000 sq ft

• Architecture: Primarily single-family homes with varied designs, many featuring open lanais and private pools

• Views: A mix of ocean, mountain, and garden views

• HOA: Oversees common areas, gated entries, and beach access path

12 Month Sales Activity

• Active (at time of writing): 2
• Pending: 0
• Sold: 2
• Average Sales Price: $2,362,500

🔗Wailea Kai Listings and Info

Wailea Golf Estates – The Height of Prestige

What makes it unique
Wailea Golf Estates is one of the most prestigious gated single-family home communities in Wailea, set within the Wailea Blue Golf Course. With large custom homes on spacious lots, residents enjoy privacy, sweeping ocean views, and the prestige of living at one of Wailea’s top addresses. The elevation within the resort means stunning sunsets and sightlines over neighboring islands.

Proximity to amenities

• Golf – Surrounded by Wailea Blue Golf Course and close to Gold and Emerald courses.

• Beaches – Less than five minutes to Wailea Beach, Polo Beach, and Ulua Beach.

• Shopping & Dining – Minutes to The Shops at Wailea and Wailea Gateway Center.

• Resorts – Near Four Seasons, Grand Wailea, and Wailea Beach Resort for spa and dining options.

Basic facts

• Type: Gated single-family home community

• Number of Homesites: 61

• Lot Sizes: ~12,000 to 20,000+ sq ft

• Views: Ocean, golf course, and mountain

• HOA: Oversees common areas and security

12 Month Sales Activity

• Active (at time of writing): 6
• Pending: 1
• Sold: 3
• Average Sales Price: $5,725,000

🔗Wailea Golf Estates Listings and Info

Living in Wailea

Choosing a home in Wailea means more than just buying real estate — it’s about embracing a lifestyle. Morning walks on the beach path, afternoons on the golf course, and sunset dinners overlooking the Pacific are everyday luxuries here. Whether you’re seeking the lock-and-leave convenience of a condo, the contemporary elegance of a townhome, or the privacy of a luxury estate, Wailea has a community designed for you.

Interested in exploring Wailea real estate?
As a Coldwell Banker Global Luxury agent on Maui, I offer insider knowledge of Wailea’s most sought-after communities, along with access to the latest MLS listings.

🔗 Browse Wailea homes and condos for sale

Discover Your Investment Opportunity in Wailea, HI

Investing in Wailea, HI, offers a unique opportunity to be part of a thriving community with stunning landscapes and a promising real estate market. Whether you're looking to buy a vacation home or a long-term investment property, Wailea has neighborhoods that cater to diverse needs and preferences. To make the most informed decision, consider reaching out to local experts who can guide you through the process. For personalized advice and insights, contact Harrison McCandless today to explore the best investment opportunities in Wailea.