While much of the country is layering up, Maui’s version of the season is defined by golden light, gentle trade winds, and days that naturally unfold outdoors. Morning coffee on the lanai. Afternoons by the pool. Evenings that end with a sunset and the soft sound of the ocean. Homes designed around infinity edge pools embody that rhythm. They frame the horizon, extend the living space outward, and create a feeling that blends comfort with resort style ease.
These three exceptional properties offer distinct interpretations of that lifestyle, each capturing a unique expression of island living. Different settings, unique architecture, but all connected by a shared experience: elevated indoor outdoor living anchored by views, privacy, and a pool that feels like it flows straight into the Pacific.
454 Wailau Place, Lahaina
A legacy estate where the pool meets the Pacific
Set across 52.775 acres, 454 Wailau Place is a private Maui retreat where the infinity edge pool melts seamlessly into the ocean beyond. Nearly 2,000 square feet of covered lanais create a true outdoor living room, with space to gather, dine, and relax while taking in panoramic views of the West Maui Mountains and the coastline.
In the winter months, the vantage point becomes even more special, with seasonal whale watching visible right from your own lanai. This is a home designed for those who value both craftsmanship and space. From koa wood details to Venetian plaster walls and a La Cornue range in the kitchen, every element is thoughtfully curated. Expansive acreage, flourishing fruit orchards, and a fully integrated solar system define this estate, offering luxury along with a sense of permanence and self-sufficiency that is increasingly rare.
Represented by: Ryan MacLaughlin and Tiffany Peralto
27 Kaulele Place, Lahaina
Contemporary Kaanapali living with panoramic views
At 27 Kaulele Place, modern design meets the best of West Maui’s coastal lifestyle. Located in Lanikeha at the Kaanapali Golf Estates, this newly built single-level home is thoughtfully positioned to capture sweeping views of the Pacific, Molokai, and Lanai, where sunsets unfold as a nightly spectacle. The open concept floor plan flows naturally onto covered lanais and an outdoor kitchen, making entertaining effortless.
The infinity edge pool is perfectly placed to frame the horizon, offering a true resort experience at home. Inside, European white oak flooring, quartz finishes, and Thermador appliances create a clean, refined look, while dual primary suites provide comfort and flexibility for hosting guests or extended stays.
Represented by: Courtney M. Brown
20 Kapuaimilia Place, Haiku
A lush North Shore retreat with infinity pool and ohana
On Maui’s North Shore, the feeling of resort living takes on a more tropical, grounded tone. At 20 Kapuaimilia Place, a gated 2 acre estate in Haiku, the infinity pool and spa are set within a landscape of mature palms, fruit trees, and vibrant greenery, creating a private sanctuary that feels both expansive and intimate.
The home’s design emphasizes flow and connection to the outdoors, with bright, open living spaces that lead directly to the pool and garden areas. A separate ohana adds flexibility for guests, extended family, or rental potential, while features like a photovoltaic system with Powerwalls support a lifestyle that is both comfortable and mindful.
Represented by: Ryan MacLaughlin and Tiffany Peralto
What connects these homes is more than the shimmer of an infinity pool spilling toward the horizon. Each residence is shaped around the rhythms of the island — light shifting across the water, trade winds moving through open rooms, the quiet line where indoors dissolves into landscape. Views stretch wide, privacy feels natural, and the architecture invites the outside in, creating an ease that lingers like an endless season of retreat.