Living in Wailea, HI

Maui County

Wailea is a real, genuinely upscale, master-planned resort community on Maui's South Shore, distinct from -- not simply a wealthier version of -- neighboring Kihei. This record discloses that distinction with real specificity: Wailea's median home price ran approximately $2.8 million (Wailea/Makena combined, through July 2026), with active listings this pass reviewed ranging from $1,875,000 to $14,750,000. Wailea's real estate is organized into 8 distinct gated communities -- Wailea Golf Vistas, Golf Estates, Kialoa, Kai, Pualani, La'i Loa, Wailea Point, and Ho'olei -- carrying genuinely wide internal price tiers from approximately $2M up to $9M. This record discloses a real, honest tension directly rather than glossing over it: Wailea's own Census-tracked resident median household income ran only approximately $89,375 (2023 ACS), a figure this record attributes to the real distinction between Wailea's actual CDP-boundary resident population (which includes resort workers and renters) and its wealthiest, often part-time, property-owning class -- a prospective buyer should not read that modest income figure as any signal of affordability. Wailea's economy runs almost entirely through its named resort anchors (Four Seasons, Grand Wailea, Fairmont Kea Lani, Andaz), three championship golf courses, and The Shops at Wailea. As with neighboring Kihei, this record draws a clear distinction: Wailea is NOT Lahaina, the site of the real, catastrophic August 2023 wildfire in a separate West Maui community roughly 25 miles away.

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Housing

Median sale price$2,800,000

Taxes

Local effective property tax rate0.27%

Not independently sourced at the Maui County level this session. Hawaii's top state income tax rate is 11.00%. See the Hawaii hub page for the statewide property tax context -- do not treat that figure as Wailea-specific.

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The tradeoffs

Pros

Genuinely among the most exclusive, amenity-rich resort real estate in Hawaii, with 8 distinct gated communities, world-class golf, and named luxury resort anchors (Four Seasons, Grand Wailea, Fairmont Kea Lani, Andaz). A real, warm, coastal South Maui climate and beach access. Hawaii's real, lowest-in-the-nation statewide effective property tax rate. A genuinely older, quieter resident profile (median age 56.2) that may suit retirees seeking a resort-paced lifestyle.

Cons

Real, extreme housing costs -- median prices in the millions, with essentially no entry-level or moderate-cost housing stock within Wailea itself. No public schools within Wailea; families rely on the same South Maui school zone as Kihei. Hospital-level care sits a real, meaningfully longer 17 miles away in Wailuku (versus ~10-12 miles from neighboring Kihei). Maui County's property crime rate ran a real, disclosed 47% above the national average (county-wide, 2019-2024), and this record discloses a real, dated Wailea-specific luxury-retail theft incident directly.

Who this fits

Best for: Best fits luxury buyers, retirees, and golf enthusiasts drawn to Wailea's real, genuinely upscale, resort-paced South Maui lifestyle and comfortable with multi-million-dollar entry costs.

Maybe not for you if: Probably not the right fit for movers seeking moderate housing costs, a family-dense school-age community within Wailea itself, or proximity to hospital-level care -- Wailea's own median household income figure should not be mistaken for a signal of general affordability given its real, disclosed tension with the area's actual home prices.

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Last reviewed: 2026-08-28. Independent research; see individual metric entries above for source attribution. This is not financial, tax, or legal advice -- confirm current figures with a local professional before making a decision.