Located just a few miles from downtown Honolulu, the Diamond Head real estate market is the first high-end community east of town. With beautiful luxury houses and condos, Diamond Head is home to Oahu's CEO's and captains of industry. Within the Diamond Head area is Kahala, which is the pinnacle of East Oahu real estate.
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Real estate buyers have many fantastic Diamond Head homes to choose from. Custom-built oceanfront and ocean view estates in Kahala can command as much as $15 million, with the elegance and luxury that's only available in Diamond Head. Along this strip of coast are the best and the biggest; the rich, and the famous.
At the same time, there are plenty of regular-sized homes, condominiums, and small apartments that are grouped together along the inner areas of these two towns. The properties all seem to kind of blend together as you're driving along.
Though upscale and expensive, Diamond Head and Kahala are surprisingly quaint and welcoming communities, with an appeal that says 'Hawaii' in many ways. Diamond Head homes, though large and impressive, don't have the overwhelming feeling of opulence that some of California's most high-end neighborhoods like Bel Aire and Westlake Village have. With all its grandness, Diamond Head has managed to stay a true neighborhood, though your neighbors might be more influential than in other areas of the island.
Homes begin around $1.5 million for a small property, while Diamond Head condos begin very low for leasehold, and around $1 million for fee simple. Oceanfront condos on "the gold coast" can range from $1 million all the way up to $5 million, while Kahala real estate begins around $3 million.
Most Diamond Head and Kahala homes were custom-built, with many of them now ready for remodeling. A large number of homeowners in the area have already started the revitalization process, with construction happening nearly on every street.
The oceanfront properties in Diamond Head are truly world classwith views to the horizon and custom homes to satisfy any taste. The boom of the 90's created several mini mansions in Kahala, and the most recent boom has created even more custom oceanfront estates with the most opulent features. I recently visited an oceanfront home with 4 refrigerators, 4 dish washers, 2 sets of laundry machines, 2 master suites, and the list goes on. For a mere $9.5 million, you can have just about anything you want in a home!
If there is one landmark that everyone associates with Oahu, it's probably Diamond Head. No, there aren't any diamonds in it, but there is quartzite, which looked like diamonds to people visiting the island hundreds of years ago.
A few good schools call this part of Honolulu home, as does the Kahala Mall. This shopping center is about 1/10 the size of Ala Moana Mall, but is much closer for the residents of East Oahu.
I recommend driving Diamond Head road at least once, to see what a beautiful place it is, and to stop at one of the lookouts over the surf. A lot of beginners surf down below at Diamond Head, as the waves are a little mushy and slow. In the summer, the surf can reach about 5-7 feet on a big day, but it's usually a real slow ride.
In the winter, there is great diving in Kahala, with plenty of reef and fish. Kahala has some of the best coastline in the world, but unfortunately, you can't see most of it because there are huge gated homes taking up the view. But for $5 million, you would expect a little privacy too, right?
A beautiful little public beach is located just off Kahala Ave., and shares the same feel of any simple Oahu beachexcept for the gorgeous mansions across the street. While most beaches in Diamond Head are rocky instead sandy, there are a few little spots to rest your toes on the soft sand.
Oahu's best private golf course, Waialae Country Club, is located in Kahala, and hosts the Hawaiian Open every year. It's an exclusive golf club that costs about $40k to join, and another $5000/yr in membership fees. For the golf enthusiast and the super rich, it's the place to be.
The Waialae Country Club also features golf course real estate that is the best on the island. Some of the homes along the fairways also have an ocean view, making them the best of both worlds on Oahu.
The beautiful Kapiolani Park is one Diamond Head's best features. Its vast size and lush trees make it a great place to spend the day with friends and family. Even though it's just one block from Waikiki, it feels like a different world. Kapiolani Park is peaceful, quiet, and truly enjoyed by the area's residents. There are frequent events in the park, including concerts, craft fairs, and even NFL pro bowl events. Best of all is the opportunity to have a quiet picnic with friends, play a game of volleyball, or head across the street for a surf at Old Man's, Tongs, or Castles.
The Diamond Head Market has great lunches, but there are several small restaurants in the area as well. My family enjoys Mi Casa, which has nice Mexican food and an outdoor feel. The Kahala Mall also has several restaurants and stores, so you rarely need to make a trip to Ala Moana or Pearlridge Mall in town.
The weather in Diamond Head and Kahala is ideal year-round, with a nice cool breeze and moderate temperatures. It doesn't rain nearly as much in Diamond Head and Kahala as it does on the Windward side in Kailua or Kaneohe, and the winds are not as strong. Diamond Head is ideal for home buyers looking to live somewhere dryer than the Windward side of Oahu, and cooler than the west side of the island.
I could mention several other amenities in Diamond Head and Kahala, but the best reason to live in this wonderful area is its proximity to town (Honolulu). The longer you live in Oahu, the more you will appreciate being able to get in and out of town quickly.
Contact AlohaTony to learn more about Diamond Head condos or houses for sale.
Exceptional owner-user opportunity featuring a 4,480 SF two-story commercial building in a prime location just off Kapahulu Avenue. Designed for professional office use, ...
Listing courtesy of CBI Residential Advisory Svcs..
$975,000 per house! TRY COOPERATIVE ownership-buy w/friends . Each owner gets their own house + rent income from 2 other rentals! DIAMOND HEAD COTTAGES terrific Property ...
Listing courtesy of KleinCo, LLC.
Each House for less than $1.0M! TRY COOPERATIVE ownership-buy w/friend. Each owner has their own house + rent income from other 2 houses! DIAMOND HEAD COTTAGES terrific R...
Listing courtesy of KleinCo, LLC.
House of Bird of Paradise - a wonderful oasis in prestigious Kahala. Grand scale interior of over 6,000sq ft, 5 spacious bedrooms and the possibility to make 6th bedroom ...
Listing courtesy of Kaina Hale Hawaii Realty Inc..
Nestled in the prestigious hillside community of Maunalani Heights, this exceptional residence offers an ideal blend of contemporary luxury, expansive living spaces, and ...
Listing courtesy of Coldwell Banker Island Prop.
Rare opportunity to own a unique combined oceanfront residence in the iconic Colony Surf on Oahu's prestigious Gold Coast. Originally two oceanfront apartments (#603 and ...
Listing courtesy of Crossover Realty Hawaii LLC.
Sophisticated single level home with a beautiful ocean view. Perched on a prime corner lot within gated community of Waialae Iki 5. Meticulously maintained single level h...
Listing courtesy of Coldwell Banker Realty.
Looking for back up offer. Easy to show. Modern Luxury timeless in Diamond Head. Experience modern island luxury, Beautifully upgraded throughout, this elegant residenc...
Listing courtesy of Central Pacific Properties Inc.
Stunning direct ocean and Diamond Head views welcome you to this spacious 2BR/2BA residence offering 1,446 sq.ft. of interior living. Thoughtfully renovated with quality ...
Listing courtesy of Shimizu Gateways Inc.
Experience refined Gold Coast living in this beautifully crafted oceanfront residence at Coral Strand Ltd. Perfectly positioned above the canopy of Kapiolani Park, this e...
Listing courtesy of List Sotheby's Int'l Realty.
Spectacular ocean views!! Nestled within the private gated community of Kahala Kua, this elegant residence exudes sophistication and luxury. Soaring high ceilings and fl...
Listing courtesy of Coldwell Banker Realty.
Rim lot. Stunning view. Refrigerator, washer and dryer, dishwasher, two split air conditioner, salt water pool, two water heaters, two ceiling fans, remote controlle...
Listing courtesy of Young Hawaii Homes, Inc..
Welcome to 559 Moaniala Street, located in the prestigious gated community of The Pointe within Hawaii Loa Ridge for double the security gates and maximum protection. Thi...
Listing courtesy of Compass.
Exceptional custom-designed residence thoughtfully designed to capture unobstructed views of the Pacific Ocean, coastline, and iconic Diamond Head. A foyer with soaring c...
Listing courtesy of Coldwell Banker Realty.
Thoughtfully reimagined and beautifully appointed, the 2026 open-concept estate blends Hawaiian-inspired finishes with refined contemporary luxury, creating the ambiance ...
Listing courtesy of OahuRE.com.
Spacious 5 bedroom 4 bath home on Maono Place, a quiet interior street, within prestigious Hawaii Loa Ridge. This home features a covered lanai with beautiful sweeping o...
Listing courtesy of Hawaii Homes & Estates LLC.
Perched in the prestigious Waiale Iki neighborhood, this newly renovated 3-bed/2-bath residence offers an exceptional blend of modern elegance, flexible living and most o...
Listing courtesy of Hawaii Life.
Privately tucked away at the end of a peaceful cul-de-sac, this exceptional 4 bdrm/4.5 bath residence in the highly coveted Waialae Iki neighborhood offers breathtaking u...
Listing courtesy of REMAX Hawaii.
This beautifully remodeled single-family home offers stunning ocean views and is designed for both comfort and entertaining. Featuring 4 bedrooms and 4.5 bathrooms, the s...
Listing courtesy of Estates Royal Limited.
$200,000 PRICE DROP!!!!!!!Step into this historic Kamaaina home that has been upgraded and remodeled. The Koa wood flooring is spectacular and has been restored to its o...
Listing courtesy of Hawaii Life.
7 Units with good income. Good location convenient location bus line, Close to Kahala Mall, Diamond Head, and easy freeway access. Buyer to do their own due diligence.
Listing courtesy of Realty 2000, Inc..
Located in the heart of Kaimuki, 3513 Harding Ave. presents a rare opportunity to acquire a multi-cottageinvestment property on a 15,000 SF lot. The property consists of ...
Listing courtesy of CBI Residential Advisory Svcs..
Located in the heart of Kaimuki, 3513 Harding Ave. presents a rare opportunity to acquire a multi-cottage investment property on a 15,000 SF lot. The property consists o...
Listing courtesy of CBI Residential Advisory Svcs..
View! View! View! This spectacular view home in lower Hawaii Loa Ridge features large 12,631 square foot rim lot with 4,132 square foot home and big swimming pool. Walk...
Listing courtesy of Coldwell Banker Realty.
Spacious 2 bedroom 2 bathroom with 1 parking. Oceanfront unit at Diamond Head Apts Ltd.
Listing courtesy of List Sotheby's Int'l Realty.
Based on information from the Multiple Listing Service of Hicentral MLS, Ltd. Listings last updated on . Information is deemed reliable but not guaranteed. Copyright: 2026 by HiCentral MLS, Ltd. IDX information is provided exclusively for consumers' personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.