269 Diamond Head Region Homes for Sale

Just listed
$6,988,000
506 Hakaka Place
4 Bd | 7 Ba | 4,575 sqft
Sun Open House 2-5pm
5343 Kahalakua Street
4 Bd | 3 Ba | 2,736 sqft
Sun Open House 2-5pm
738 22nd Avenue
5 Bd | 3.5 Ba | 2,515 sqft
4908 Kahala Avenue
6 Bd | 6.5 Ba | 6,625 sqft
Sun Open House 2-5pm
3616 Sierra Drive
7 Bd | 4 Ba | 4,244 sqft
4912 Poola Street
3 Bd | 2 Ba | 1,634 sqft
269 Kaialii Place
5 Bd | 8 Ba | 6,034 sqft
1176 Hind Iuka Drive
4 Bd | 2 Ba | 1,056 sqft
Sun Open House 2-5pm
1021 Iiwi Street
5 Bd | 3 Ba | 3,689 sqft
559 Moaniala Street
4 Bd | 5 Ba | 3,912 sqft
4612 Aukai Avenue
5 Bd | 5.5 Ba | 6,129 sqft
5216 Hao Place
3 Bd | 1 Ba | 1,328 sqft
1042 8th Avenue
3 Bd | 1.5 Ba | 1,168 sqft
Total 269 Diamond Head Region Homes - 15 loaded
Diamond Head Region Homes Overview
Note: This page displays homes for sale in the Diamond Head region, which is 1 of 3 regions in Honolulu. If you want to search all Honolulu, then visit our Honolulu homes for sale page.

When you hear the words 'Diamond Head homes', it's natural to immediately think of large and very exclusive oceanfront mansions sitting under the the iconic volcanic cone. Those are the houses that get the profiles in upscale magazines and tv shows that focus on the Other Half. The Diamond Head region, though, takes in a lot more and there's a lot of variety that spans the market.

In Honolulu real estate, the Diamond Head district takes in a few neighborhoods, stretching from its western borders of Kapahulu and Kaimuki, out to its eastern end that stops at Kuliouou and Paigo Lagoon. You'd be in good company if you didn't realize that the smaller homes sitting behind Diamond Head are just as much a part of this same overall district as Doris Duke's Shangri-La.

It all starts with those homes in the Kapahulu & Kaimuki districts, many of which are of the classic, wooden Plantation Style, Dickey roof and all. Intermingled you will find newer and, in some cases, architecturally very different houses. This wide variety of styles is because these are long established neighborhoods, rather than the result of planning or a developer's vision. It's a wonderful patchwork that sometimes find the homes almost cheek-to-cheek in many areas.

Above these, literally, are neighborhoods such as Wilhelmina Rise and St. Louis Heights where your outlook can be magnificent, taking in a huge sweep of Honolulu and even the ocean. The words 'Rise' and 'Heights' are very appropriate for the way these residences stretch far up the hills. A large percentage of them are still here from the original build up during the 1950's and 60's, along with some more recent additions. These are great places to settle for those who don't mind, or even prefer, a high perch to live on and take it all in.

Heading immediately east from Kaimuki takes you right into Kahala, a name immediately recognized, not only in the Islands but around the world. It's become almost a cliché to call it the Beverly Hills of Honolulu, but it's also accurate. From the design and look alone, many of the houses here probably do have counterparts back in California. The apex of the market are the homes found on Kahala Avenue, right on some of the most desirable coastline in Hawaii. They will be hard to see, though, behind the large gates and walls that front most of the properties.

Gates and walls continue to be a prevalent feature on the makai side of Kalanianaole Hwy as you continue east through Wailupe, Aina Haina Beach and oceanfront Niu Beach. Just as Kaimuki had its 2 neighborhoods looking over it, Wailupe has Waiale Iki and Hawaii Loa Ridge. Their high positioned homes are also higher in price and desirability, a product of the development boom in the 1980's that saw larger houses built in coveted climes like these. After seeing the views from here of the Pacific and the Honolulu city scape, you'll immediately understand why.

Back on street level, you'll come next to Aina Haina, famous for its low-rise ranch style homes as is Niu Valley, its neighbor. The latter is especially beautiful with the smaller vertical footprint of the homes giving you a Big Sky feeling with the backdrop of the awesome Koolaus. These are also products of the post-World War II construction surge and many families are the same ones who bought originally, as are the houses themselves, of course.

Overall, this is probably the highest cost real estate district in Hawaii. You can still find reasonable prices, for the Islands, in some Diamond Head region homes for sale, but this is always an in-demand area. Plenty of shopping, generally good schools and beautiful scenery, though it often leans to being very urban. Factor in places like the Gold Coast, Kahala and Black Point within its borders and that takes the price tags up into the stratosphere. It's a case of a lot of demand and not enough supply, but how many who live here have ever regretted the purchase? Let's face it. Not very many.

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Diamond Head Region Photos

Recently Sold in Diamond Head Region

Sold12/6/'19
$3,770,000 (Sold Price)
5581 Kalanianaole Highway
5 Bd | 3 | 3,605 sqft
Oceanfront
Sold12/6/'19
$1,080,000 (Sold Price)
6075 Keoki Place
3 Bd | 1.5Ba | 1,026 sqft
Year Remodeled: 2017
Sold12/5/'19
$975,000 (Sold Price)
871 Leighton Street
4 Bd | 3 | 2,163 sqft
Ocean view
Sold12/5/'19
$840,000 (Sold Price)
956 Hao Street
3 Bd | 1.5Ba | 1,230 sqft
Sold12/4/'19
$1,450,000 (Sold Price)
5396 Poola Street
5 Bd | 3.5Ba | 2,893 sqft
Ocean view
Sold12/2/'19
$1,400,000 (Sold Price)
4995 Waa Street
4 Bd | 2.5Ba | 2,214 sqft
Year Remodeled: 2016
Sold11/29/'19
$805,000 (Sold Price)
3 Bd | 1 | 1,076 sqft
Sold11/29/'19
$800,000 (Sold Price)
5404 Halapepe Street
4 Bd | 2.5Ba | 1,334 sqft
Ocean view
Sold11/27/'19
$605,000 (Sold Price)
1308 16th Avenue
3 Bd | 2 | 1,024 sqft
Sold11/27/'19
$2,420,000 (Sold Price)
946 Waiohinu Drive
4 Bd | 4 | 3,134 sqft
Built: 2012
Sold11/26/'19
$3,200,000 (Sold Price)
619 Kahiau Loop
4 Bd | 3.5Ba | 4,134 sqft
Ocean view
Sold11/26/'19
$1,170,000 (Sold Price)
4451 Sierra Drive
3 Bd | 2 | 1,964 sqft
Ocean view
Sold11/25/'19
$875,000 (Sold Price)
1936 10th Avenue
5 Bd | 2.5Ba | 2,600 sqft
Ocean view
Sold11/22/'19
$600,000 (Sold Price)
2237 Waiomao Road
4 Bd | 2 | 1,456 sqft
Sold11/22/'19
$1,404,800 (Sold Price)
714 16th Avenue
5 Bd | 4 | 2,624 sqft
Ocean view
Sold11/19/'19
$975,000 (Sold Price)
3625 Sierra Drive
3 Bd | 1 | 1,075 sqft
Ocean view
Sold11/19/'19
$4,350,000 (Sold Price)
1169 Ikena Circle
5 Bd | 4.5Ba | 5,595 sqft
Ocean view
Sold11/15/'19
$1,925,000 (Sold Price)
5608 Poola Street
5 Bd | 3.5Ba | 5,305 sqft
Ocean view
Sold11/14/'19
$1,180,000 (Sold Price)
402 Hind Drive
4 Bd | 2.5Ba | 1,300 sqft
Year Remodeled: 2019
Sold11/13/'19
$1,200,000 (Sold Price)
1358 Kalaniiki Street
3 Bd | 2 | 1,557 sqft
Ocean view
Sold11/12/'19
$900,000 (Sold Price)
4006 Iwalani Place
3 Bd | 1.5Ba | 1,452 sqft
Sold11/8/'19
$1,028,000 (Sold Price)
1439 9th Avenue
3 Bd | 2 | 1,608 sqft
Sold11/8/'19
$1,198,000 (Sold Price)
2049 Oswald Street
3 Bd | 2.5Ba | 1,752 sqft
Ocean view
Sold11/8/'19
$1,750,000 (Sold Price)
4957 Mana Place
6 Bd | 3 | 3,314 sqft
Ocean view
Sold11/7/'19
$1,100,000 (Sold Price)
429 Puamamane Street
3 Bd | 2 | 1,654 sqft
Year Remodeled: 2019
Sold11/7/'19
$1,400,000 (Sold Price)
4846 Analii Street
3 Bd | 3 | 2,445 sqft
Ocean view
Sold11/7/'19
$920,000 (Sold Price)
5126 Keikilani Circle
4 Bd | 1.5Ba | 1,488 sqft
Sold11/7/'19
$1,750,000 (Sold Price)
4454 Kilauea Avenue
3 Bd | 2 | 2,024 sqft
Year Remodeled: 2019
Sold11/6/'19
$1,190,000 (Sold Price)
1805 Bertram Street
3 Bd | 1.5Ba | 1,085 sqft
Ocean view
Sold11/6/'19
$2,400,000 (Sold Price)
3234 Noela Drive
8 Bd | 9 | 5,732 sqft
Year Remodeled: 2019
Sold11/1/'19
$1,625,000 (Sold Price)
386 Wailupe Circle
6 Bd | 3.5Ba | 1,395 sqft
Sold11/1/'19
$2,400,000 (Sold Price)
4208 Kaimanahila Street
3 Bd | 3 | 2,588 sqft
Sold11/1/'19
$1,550,000 (Sold Price)
4028A Keanu Street
5 Bd | 3.5Ba | 2,885 sqft
Ocean view
Sold11/1/'19
$1,817,000 (Sold Price)
3415 Kanaina Avenue
10 Bd | 15.5Ba | 4,604 sqft
Built: 2017
Sold11/1/'19
$1,310,000 (Sold Price)
5066 Poola Street
3 Bd | 2.5Ba | 1,824 sqft
Ocean view
Sold10/31/'19
$2,500,000 (Sold Price)
1922 Hawane Place
4 Bd | 3 | 4,622 sqft
Ocean view
Sold10/31/'19
$775,000 (Sold Price)
3460 Kalua Road
3 Bd | 2 | 970 sqft
Sold10/31/'19
$1,260,000 (Sold Price)
5362 Kilauea Avenue
3 Bd | 2 | 1,744 sqft
Sold10/31/'19
$2,350,000 (Sold Price)
915 Waiiki Street
4 Bd | 4.5Ba | 3,188 sqft
Sold10/30/'19
$1,690,000 (Sold Price)
4590 Waikui Street
4 Bd | 3 | 2,424 sqft
Year Remodeled: 2017
Sold10/29/'19
$1,500,000 (Sold Price)
5853 Haleola Street
6 Bd | 4 | 3,348 sqft
Ocean view
Sold10/28/'19
$1,608,750 (Sold Price)
3607 Trousseau Street
4 Bd | 4 | 2,474 sqft
Ocean view
Sold10/28/'19
$900,000 (Sold Price)
1490 Ainakoa Avenue
3 Bd | 2 | 1,416 sqft
Sold10/28/'19
$820,000 (Sold Price)
1520C Palolo Avenue
3 Bd | 2 | 1,167 sqft
Year Remodeled: 2015
Sold10/28/'19
$1,850,000 (Sold Price)
1549 Ipukula Street
4 Bd | 3 | 2,666 sqft
Ocean view
Sold10/28/'19
$1,700,000 (Sold Price)
1030 Pueo Street
4 Bd | 3 | 2,430 sqft
Sold10/25/'19
$1,652,000 (Sold Price)
316 Nenue Street
4 Bd | 3 | 2,617 sqft
Year Remodeled: 2018
Sold10/25/'19
$1,090,000 (Sold Price)
1341 16th Avenue
5 Bd | 2 | 2,056 sqft
Sold10/25/'19
$1,630,000 (Sold Price)
3873 Nikolo Street
2 Bd | 1.5Ba | 1,000 sqft
Sold10/25/'19
$967,000 (Sold Price)
3618 Trousseau Street
3 Bd | 1 | 932 sqft