Discover Wailea Fairway Estates
LISTINGS
Latest Homes for Sale in Wailea Fairway Estates
OVERVIEW

Luxury Homes for Sale in Wailea Fairway Estates, Wailea, HI
Wailea Fairway Estates is one of the most distinguished residential enclaves in South Maui, offering an intimate atmosphere with just 31 family residences. Established as an original Wailea residential community, it is known for its low-density feel and classic charm, spanning approximately 14 acres of prime coastal real estate. Those looking for Wailea Fairway Estates for sale will find a neighborhood where the homes are expertly positioned to maximize both privacy and the surrounding island beauty.
The neighborhood is characterized by a mix of mid-century modern influences and contemporary Hawaiian architecture. Many properties here feature direct golf course frontage, as the community is nestled along the 11th and 16th fairways of the renowned Wailea Blue Course. This positioning provides residents with expansive, manicured “backyards” and buffered views that extend toward the Pacific Ocean. This gated community sits directly across the street from white sand Ulua beach, an excellent snorkel and bodysurfing beach and steps away from the high-end amenities of the Wailea Resort. Its location is truly unmatched for convenience, offering a quiet retreat while remaining exceptionally close to the island’s best beaches and luxury hubs.
Top Reasons to Buy in Wailea Fairway Estates, Wailea, HI
Premier Golf Course Living
The community is uniquely designed to wrap around the lush greens of the custom homes Wailea Blue Course area, offering a serene backdrop for everyday living. Residents enjoy the prestige of direct golf course frontage, ensuring that sweeping views of the fairways remain unobstructed by future development. This proximity to the course provides a quiet, park-like atmosphere where the only sounds are the occasional breeze through the palms and the distant break of the ocean. For the avid golfer or those who simply appreciate manicured landscapes, the integration with the “Old Blue” course is a significant lifestyle benefit.
Unbeatable Pedestrian Access
One of the most practical advantages of living here is the ability to walk to Wailea Village and the nearby Shops at Wailea for world-class dining and retail. Unlike more remote hillside subdivisions, this community allows for a truly pedestrian-friendly lifestyle where morning coffee or evening fine dining is just a short stroll away. You are also within walking distance of some of Maui’s most celebrated shorelines, including Ulua and Mokapu beaches. This rare combination of a residential sanctuary and walkability to resort amenities makes it a top choice for active buyers.
Established Community Character
As an original Wailea residential development, this neighborhood possesses a mature landscape and a sense of permanence that newer subdivisions often lack. The oversized lots, ranging from 12,000 to over 18,000 square feet, provide ample room for private pools, lush tropical gardens, and expansive outdoor entertaining spaces. There is a palpable pride of ownership here, with many homes having undergone meticulous renovations to blend historic Wailea charm with modern luxury. Choosing a home in this established area means joining a community with a proven track record of long-term value and architectural integrity and being an owner in this community gives you “golf member” status, which provides access to special rates and tee times at the nearby Wailea Blue, Gold, and Emerald courses
Wailea Fairway Estates, Wailea, HI Real Estate Snapshot
- Price Range: Homes typically range from $3,500,000 to over $6,000,000 depending on golf course proximity and ocean view quality.
- Typical Year Built: Much of the community was established in the mid-1970s, with many homes featuring extensive modern updates.
- Interior Square Footage: Residences generally offer between 2,500 and 4,500 square feet of living space.
- Typical Lot Size: Expansive lots are a hallmark of this area, typically ranging from 12,000 to 18,500 square feet.
- Market Fact: The community consists of only 31 home sites, making inventory extremely rare and highly sought after when it hits the market.
DEMOGRAPHICS
Who Lives in Wailea/Makena
ENTERTAINMENT
Things to do around Wailea Fairway Estates
The Shops at Wailea
A premier destination for luxury retail, local boutiques, and upscale island dining.
Wailea Blue Golf Course
The "Old Blue" offers a classic resort experience with wide fairways and stunning views.
Ulua Beach Park
A beautiful crescent beach perfect for morning snorkeling and sunset walks along the
Wailea Tennis
Consistently ranked as one of the top tennis destinations in the country with 11 courts.
SCHOOLS
Schools near Wailea Fairway Estates
ON THE MAP
Wailea Fairway Estates on the Map
To reach the community from Kahului Airport, head south on the Airport Access Road and turn left onto Puunene Avenue, which becomes the Piilani Highway (Highway 31). Follow the Piilani Highway south for approximately 7 miles until it ends and curves right onto Wailea Ike Drive. At the first major intersection, turn right onto Wailea Alanui Drive. Continue past The Shops at Wailea and turn right onto Kalai Waa Street, where you will find the entrance to the estates nestled along the golf course.