Pineapple Hill
Pineapple Hill is the largest residential subdivision within Kapalua Resort, built in two phases that still shape how the community reads today. The original Pineapple Hill, completed in 1989 and 1990, laid out 99 homesites on roughly quarter-acre lots around six original floor plan options. Pineapple Hill Estates, the second phase, added 31 larger homesites on roughly half-acre lots for custom-built homes. Across both phases, homes typically run 3,350 to 5,100 square feet, with some current listings closer to 3,300 to 4,600 square feet, generally 3 to 4 bedrooms and 3 to 5 bathrooms, sized for full-time island living rather than a compact vacation condo.
The community is gated, with its own pool, tennis and pickleball courts, and entertainment area, and residents also carry access to Kapalua Resort's broader amenities, including its beaches, golf courses, and dining. Pineapple Hill sits well outside the area burned in the August 2023 Lahaina wildfire; Kapalua lost power and phone service for a few days afterward, along with the rest of West Maui, but no homes here were damaged. That combination, gated privacy plus resort-wide access, is a big part of Pineapple Hill's appeal to buyers who want a real house on the ground rather than a condo unit, without giving up the conveniences that make Kapalua one of Maui's most established resort communities.
The short version
- ✦Largest residential subdivision within Kapalua Resort
- ✦Phase 1 (Pineapple Hill): 99 homesites on roughly quarter-acre lots, built 1989 to 1990
- ✦Phase 2 (Pineapple Hill Estates): 31 homesites on roughly half-acre lots, custom builds
- ✦Homes typically 3,350 to 5,100 sq ft, 3 to 4 bedrooms, 3 to 5 bathrooms
- ✦Gated, with a private pool, tennis and pickleball courts, and entertainment area
- ✦Residents also access Kapalua Resort's broader beaches, golf, and dining
- ✦Outside the August 2023 Lahaina wildfire's burn path; no homes here were damaged
By the numbers
- Built
- 1989 to 1990 (Phase 1); Pineapple Hill Estates added later as custom builds
- Homes/lots
- 130
- Typical lot size
- Roughly 0.25 acres (Phase 1); roughly 0.5 acres (Pineapple Hill Estates)
- Typical home size
- 3,350 to 5,100 sq ft
- Gated
- Yes
In the neighborhood
Questions buyers ask
Where is Pineapple Hill located?
Pineapple Hill sits within Kapalua Resort on Maui's northwest coast, and is the largest residential subdivision inside the resort.
How big is Pineapple Hill and when was it built?
The original Pineapple Hill phase was built in 1989 and 1990 with 99 homesites on roughly quarter-acre lots. A second phase, Pineapple Hill Estates, added 31 larger homesites on roughly half-acre lots for custom-built homes. Homes across both phases typically run 3,350 to 5,100 square feet.
What amenities come with a home in Pineapple Hill?
The subdivision is gated with its own pool, tennis and pickleball courts, and entertainment area, and residents also have access to Kapalua Resort's broader amenities, including its beaches, golf courses, and dining.
Was Pineapple Hill affected by the August 2023 Lahaina wildfire?
No. Pineapple Hill and the rest of Kapalua Resort sit well outside the fire's burn path. Kapalua lost power and phone service for a few days afterward, like the rest of West Maui, but no homes here were damaged.
Current listings in Pineapple Hill
Live MLS search, pre-filtered to Pineapple Hill. Press Search inside the box to see current listings.