Wailea Highlands: Information and Real Estate Insights

Overview of Wailea Highlands

Wailea Highlands is an exclusive residential community adjacent to the Hotel Wailea in Maui’s upscale Wailea resort area. Comprising approximately 24 homesites across 14 acres, this community offers stunning views of the Pacific Ocean, including Molokini and Lanai, and is ideal for whale watching in winter. Homes range from $4 million to over $10 million, featuring private pools, gourmet kitchens, and unique architecture.

The community features well-maintained landscaping, quiet streets, and cul-de-sacs. Residents enjoy proximity to beaches, golf courses, dining, shopping, and the scenic Wailea Beach Walk. Kihei town nearby provides additional recreational activities and entertainment, making it an ideal choice for those seeking luxury living in Maui.


Wailea Highlands Map

Neighborhood Configuration

The 14.5-acre development consists of 24 lots, making it the smallest gated neighborhood in Wailea. However, it distinguishes itself by offering the most extensive land cuts in the area. Each lot in this subdivision features custom-built homes. The lots vary in size, ranging between 20,000 to 30,000 square feet. These homes are equipped with amenities such as private pools, expansive square footage, and distinctive architectural designs.

What We Love

Wailea Highlands is exclusive. Homes do not turn over frequently, so when they do, it’s usually an attractive market offering.

What We Could Do Without

Nothing. I really love what the Highlands have to offer. The only complaint I hear from clients in Wailea subdivisions is that they wish there were more full-time residents to establish a social connection with.

sunset over the ocean in wailea maui

Onsite Amenities

  • Private Roads
  • 24-Hour Gated Security

Nearby Amenities

Some of the most well-known Maui golf courses are only around the corner. If shopping is your favorite pastime, The Shops at Wailea offers extensive options. Not to mention the proximity to some of the world’s most magnificent beaches (Big BeachLittle Beach, and Keawakapu Beach).

Wailea Highlands Sales Statistics

Please feel free to reach out directly for active listings, pending sales, specific sales data, or current price opinions.

The report below is real-time data sourced from the Realtors Association of Maui. The statistics include Wailea Highlands’ average sales price and average price per square foot. These graphs will update automatically with the most recent data.

3 Bedrooms

4 Bedrooms

Association Information

For up-to-date information on Homeowner Association (HOA) fees and related matters, don’t hesitate to reach out via call or email.

Primary Uses

Long-Term Rental

Long-term rentals are considered six months or longer here in Maui. This option does make it difficult to use the unit for owner stays, but it can help offset the cost of ownership.

Second Home

If your goal is not to maximize your ROI but to simply use the unit as you please, you can do so. You would pay the highest and best use for real property tax.

Owner Occupant

If Maui is where you want to call home, the owner-occupant is the one for you. If you spend 270 days out of the year on Maui and your unit is your primary residence, then you can apply for the Owner Occupant exemption (frequently asked questions).

South Maui Map

South Maui Map


The zoning for Wailea Highlands is R-3 Residential. As per Maui County Rules, vacation rentals are not allowed.


Taxes to consider when owning at Wailea Highlands:

  • General Excise Tax
  • Real Property Tax (This rate will change depending on your use. You may fall under short-term vacation rental, long-term rental, or the base zoning if your unit is an empty second home or owner-occupied.)


Wailea Weather

Helpful Weather Resources:

blue water and white sand beach

Why Tim Stice?

I love what I do and I’m here to offer my clients outstanding service. My team and I have seen almost every scenario imaginable (at least, we’d like to think). Through solution-based problem-solving, transparent communication, and unrivaled market knowledge, we have successfully navigated over a half billion in closed transactions. We care about our clients and are eager to earn the title of your real estate representative.

Give me a call or shoot me an email.

Tim Stice | 808.268.8511 |

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