Maui Meadows

Maui Meadows climbs the hillside above Piilani Highway in South Kihei, bordering the 18,000-acre Ulupalakua Ranch at its upper elevations. The extra few hundred feet of elevation compared to the coast below brings noticeably cooler evenings and open ocean views toward Kahoolawe, Lanai, and Molokini on clear days. Originally three separate subdivisions platted in the late 1960s and early 1970s and later consolidated under one name, the neighborhood today holds roughly 600 homes plus about 30 remaining vacant land parcels, most on half-acre-plus lots. Architecture ranges widely, from older plantation-style houses to newer custom builds, reflecting decades of individual owners building to their own taste rather than a single master developer's plan.

There's no gate and no traditional HOA here. Instead, a Neighborhood Association formed in 1999 (which absorbed the earlier Maui Meadows Homeowners Association in 2008) looks after community interests and maintains its own website at mauimeadowsna.com. Relaxed CC&Rs allow detached ohana units, private tennis courts, pools, boat parking, and even orchards on larger lots, though homesites bordering the ranch at the upper edge of the subdivision require cattle-proof fencing. Streets have no sidewalks and limited lighting, curbs, or gutters, giving the whole neighborhood a rural, unhurried feel that's hard to find this close to Kihei's beaches and restaurants. For buyers who want land, flexibility, and a real sense of community organization without resort-style rules, Maui Meadows is one of South Maui's most established choices.