Wailea Fairway Estates
Wailea Fairway Estates is a compact enclave of 31 custom homes on about 14 acres off Wailea Alanui, in the heart of Wailea Resort. Most homes were built between 1977 and 1985, making this one of the earliest subdivisions in Wailea and, by some accounts, the first completed gated enclave in the resort. Lots run 12,000 to 18,000 square feet, with homes typically between 2,300 and 3,500 square feet, and some of the larger custom homes reaching 5,000 square feet or more. Several homes have private pools and spas. There's no shared community clubhouse here the way some of Wailea's condo complexes have one.
One detail sets Fairway Estates apart from much of Wailea's for-sale inventory: short-term vacation rentals are not allowed. The subdivision isn't on Maui County's Minatoya or hotel-zoned rental lists, and listing material consistently describes it as long-term and full-time residential use only. That makes it a residential pocket within a resort otherwise built around short-term rental income, appealing to buyers who want a full-time or long-term second home in Wailea without a rotating cast of vacationing neighbors. Buyers counting on rental income should confirm current rules with the HOA and county before writing an offer. Its early construction dates mean many homes have been renovated over the decades, and its location near the golf courses and resort amenities keeps it a sought-after address for buyers prioritizing quiet over rental yield.
The short version
- ✦31 custom homes on roughly 14 acres off Wailea Alanui, in the resort core
- ✦Built mostly 1977 to 1985, among the earliest subdivisions in Wailea
- ✦Historically marketed as the first completed gated enclave in Wailea Resort
- ✦Some homes have private pools and spas; no shared community clubhouse
- ✦Short-term vacation rentals not allowed; long-term and full-time residential use only
- ✦Lots 12,000 to 18,000 sq ft, homes 2,300 to 3,500 sq ft, some larger custom homes up to 5,000 sq ft or more
By the numbers
- Built
- 1977 to 1985
- Homes/lots
- 31
- Typical lot size
- 12,000 to 18,000 sq ft
- Typical home size
- 2,300 to 3,500 sq ft
- Gated
- Yes
In the neighborhood
Questions buyers ask
Where is Wailea Fairway Estates located?
It's off Wailea Alanui in the heart of Wailea Resort, among the resort's earliest built neighborhoods.
How many homes are there and when were they built?
There are 31 custom homes on about 14 acres, most built between 1977 and 1985. It's often described as the first completed gated enclave in Wailea Resort.
Can homes in Wailea Fairway Estates be used as vacation rentals?
No. Short-term vacation rentals aren't allowed here. The subdivision isn't on Maui County's short-term rental lists, and it's used for long-term and full-time residency, which keeps it a quieter, more residential pocket than much of Wailea's condo and home inventory. Confirm current rules with the HOA and county before assuming a rental scenario.
Current listings in Wailea Fairway Estates
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