6 Hillcrest Kailua Homes for sale

1384 Aupupu Street
3 Bd | 3.5 Ba |  3,320 sf
Sun Open House 2-5pm
1312 Aupapaohe Street
3 Bd | 2.5 Ba |  1,950 sf
Ocean view
Sun Open House 2-5pm
1392 Aupupu Street
4 Bd | 3 Ba |  2,405 sf
Ocean view
1273 Aupupu Place
5 Bd | 5.5 Ba |  4,870 sf
Ocean view
Sun Open House 2-5pm
1384 Aupupu Street
4 Bd | 3 Ba |  2,778 sf
Ocean view
1255 Aupupu Place
3 Bd | 2.5 Ba |  2,624 sf
Ocean view
Total 6 Hillcrest Homes - 6 loaded
Hillcrest Homes Overview
See this aerial video of homes in Hillcrest.

The Hillcrest neighborhood of Kailua follows the pattern of the other upscale neighborhoods that line the heights of Oahu. Owners eagerly climb these rises to revel in the views they afford so beautifully. Depending on where you are, lots in Hillcrest can look out at the calm waters of Enchanted Lake, the active ocean depths of Kailua Bay, and the emerald greenery of the Koolau Mountains.

These abodes bring other benefits as well that are less dramatic, but equally important. Half of the streets in this neighborhood are cul-de-sacs, where owners can count on few cars besides theirs coming through, an environment that promotes valued privacy and a safe place for your kids to play. Keep in mind that this is truly a hillside community, with steep streets, so your home is terraced into the slope, making the vantage point for the expansive views possible.


The community is flanked by the larger areas of Kailua Bluffs and Keolu Hills, sitting not too far up from the favorite local beaches of Bellows. It's a more private corner of Kailua real estate, removed from where the growing number of tourists spend their time.

Hillcrest Real Estate – Large Homes, Large Lots
The first houses were built in the 1970's, with new homes added in the following decades by each original owner, rather than developers. That has meant large custom homes, many easily falling into the 'Luxury' category. This shouldn't be surprising in a neighborhood with these vistas, as well as an enduring serenity its location ensures and the very large lots.

With 7,000 to 12,000 sq ft, you can understand the attraction for those who want latitude to remodel or just maintain a substantial outside space to enjoy. The interiors are uniformly roomy as well, with an average of 2,500 sq ft inside their walls. This is not the place to shop for a starter home.

These attributes have resulted in recent homes for sale in the Hillcrest neighborhood to go for $900K to $1.5M. When they are sold, that is. Going by the listing rates of the recent past, you may see only 2 or 3 a year come up for sale. In short, this is an exclusive neighborhood, the openings few.

Desirable is the only way to describe this community that scales the heights above Kailua Bay. It is highly recommended you act immediately when a Hillcrest home does come on the market. You will have competition and it will be fierce, especially once the views are experienced in person.

More Details

Recently Sold in Hillcrest

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Sold6/22/'18
$1,422,500
1422 Auauki Street
6 Bd | 4 |  2,728 sf
Ocean view
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Sold6/4/'18
$1,295,000
1448 Aunauna Street
2 Bd | 1 |  2,044 sf
Ocean view
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Sold3/23/'18
$1,200,000
1326 Aupupu Street
4 Bd | 3.5Ba |  2,662 sf
Ocean view
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Sold2/22/'18
$1,585,000
1279 Aupupu Place
4 Bd | 3 |  4,200 sf
Ocean view
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Sold1/31/'18
$1,228,000
1366 Aupupu Street
4 Bd | 3 |  2,649 sf
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Sold10/6/'17
$1,269,000
1416 Auauki Street
3 Bd | 2.5Ba |  2,500 sf
Ocean view
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Sold5/4/'17
$1,200,000
1272 Auwaiku Street
3 Bd | 2 |  2,024 sf
Year Remodeled: 2015
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Sold12/14/'16
$1,295,000
1395 Aupula Place
5 Bd | 3 |  2,528 sf
Year Remodeled: 2016
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Sold9/21/'16
$1,050,000
1328 Aupupu Street
4 Bd | 2.5Ba |  2,427 sf
Ocean view
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Sold8/1/'16
$1,010,000
1382 Aupapaohe Street
4 Bd | 2 |  1,597 sf
Ocean view