25 Diamond Head Homes for Sale

More About Diamond Head
Diamond Head real estate has an inherent uniqueness - you own property next to not just a State Monument, but a beloved symbol of the tropical ideal. That brings prestige to your home just by proximity alone, as well as challenges you wouldn't face elsewhere, even in Hawaii.

Our belief is that the full picture is vital to an enduringly happy homebuyer experience, one that lasts for the entire time you own your residence. Believe it or not, there are issues to contemplate, as well as the obvious benefits, before you buy that home in the shadow of this great profile.

Cost is a factor present in every property transaction in the Islands. It's an often-cited fact that you pay more in Hawaii due to the land values in a high-demand, low supply market. When you're shopping for a residence in a neighborhood like Diamond Head, that truth is multiplied.

Entering this area between Waikiki and Kahala requires someone unafraid of sticker shock. It's not merely that entrance price, either. One has to keep in mind that property taxes are an annual bill that can be quite high, based as it is on the perpetually climbing Diamond Head real estate values. It's an expense that does not go down.

In addition, many who look at property here are unaware that this is a designated Special District. That brings an entirely different, and more restrictive, set of regulations overseeing any construction within it.

There are height limits, set architectural and landscaping design rules and other requirements that can make building your new home, or doing the renovations you were dreaming of, difficult. You'll face greater red tape here and may even have to adjust your plans to meet what the law says is allowed in this district.

Finally, due to the lay of the land there aren't any real beaches inside the strict limits of this region. A few small pockets of sand here and there, but a majority of this coastline is at the bottom of slopes that end in rougher terrain or just drop off to pure ocean. You can live oceanfront here, but rarely beachfront.

To be perfectly honest, we had to think long and hard to come up with any drawbacks to buying a home in Diamond Head. One of the reasons for the success of these properties is that there's 'not a lot not to love', as they say. It's much easier to tell you about the positive side of the equation, because there's so much of it.

Diamond Head Real Estate - A Lot of Upside
As ever-present as it is, the Diamond Head lifestyle is about much more than a prominent landmark. The calm serenity of the days you'll spend here are equalled few other places. Throughout this community there seems to be an unspoken law here that the the noise level is to be kept low. For many the sound of the waves hitting the shoreline is the loudest sound they hear from home.

With this kind of quiet, it's hard to believe you're living next to the busiest urban center in the Islands, where tourists make their presence very well known at all hours.

That proximity to Waikiki, as well as Kahala, means you have a lot of shopping and dining at the end of a five minute drive or maybe just an easy walk westward. It isn't just those man-made benefits of the tourism center that will bring their own joys to your life. It's also the long stretches of sand, from Kaimana Beach to the Royal Hawaiian sands and beyond. They're yours all year 'round.

Kapiolani Park is an even closer neighbor, a massive playground for almost any activity or exercise plus the perfect site to gather friends and family for a barbecue.

Though Diamond Head doesn't have extensive beach areas itself, it can claim ocean views that have the level of beauty to justify the prices these homes command. Many, like the houses on the slopes below Diamond Head Road, have uninterrupted vistas of these waters that can clinch a sale from one glimpse.

We could easily go on – and on - , but the message is clear. This is one of those neighborhoods that brings a certain peace and a particular enrichment to your soul, benefits far beyond any real estate 'location' bragging rights. It comes with a certain price tag, but that might be cheap in comparison to the what you get back every single day of living here.

The Future of Diamond Head Real Estate
There's no question that the price and value of Diamond Head real estate will continue to climb. The appeal of the world-class scenery, its often luxurious houses with the kind of privacy the well-heeled crave and an ocean view that has few equals are solid foundations that will remain in place forever.

In addition, the growing presence of Chinese and Korean buyers, attracted by the prominence of this place, along with the investment potential, is resulting in more well-funded competition for these properties, which will inevitably drive prices upward.

A very restricted supply, combined with an international allure, will produce new price-setting records being set here in the coming years. The future is bright for this section of Paradise.

Area Amenities
This region is rich in options and essentials, but keep in mind that many of them are not within the neighborhood itself. The regulations that come with the presence of a State Monument and treasured historic landmark like Diamond Head restrict commercial building even more than residential. You're still in a central location, though, with a lot to offer, even if you have to travel a little bit to reach some of these benefits.

Schools & Childcare
Diamond Head has schools nearby for all levels of education, beginning with preschool on up to the highest levels at the University of Hawaii. Most are not walking distance, though, but they are close enough that driving will get you there quickly. Busing is available for public schools as well, of course.

Unity School – Serves keiki ages 1 to 5. Church sponsored, but curriculum focus isn't religious. Aim is positive reinforcement and atmosphere, even in their discipline practices.

Waikiki Elementary – One of the highest rated schools in Hawaii. Keeps parents involved with weekly newsletters and many programs, including after-school A+, for the children. Sits right along Monsarrat Ave.

Kaimuki Middle School – Located behind Diamond Head where Kahala & Kaimuki meet. Teaches 6th to 8th graders. Ranked recently in the top 3% of Hawaii middle schools.

La Pietra School – Stands on site right against Diamond Head beside Kapiolani Park. Exclusively for girls, grades 6 to 12, with strong focus on College Prep.

Kapiolani Community College – Campus is across the road from back of Diamond Head. Trade training programs, certifications in many areas plus academic classes. Learn new skills for the job marketplace or work toward your degree.

UH-Manoa – The predominant university in all Hawaii. Almost limitless areas of study, from Bachelor to Doctoral degrees.

Public Transportation
The Bus system has a few routes that serve both the west and south, side of Diamond Head, such as #23, as well as those that go around the front on Diamond Head Rd, like #22. The #23 travels between Waikiki and Sea Life Park, going up Monsarrat Ave and around the back side of Diamond Head.

#22 serves the same area, with some variations, including going around the face of Diamond Head, along the ocean. If you're going somewhere beyond their start and end points, you will have to transfer, but with Ala Moana Center as one of their stops, you have access to routes going all over Oahu.

Supermarkets & Groceries
Your grocery trips will take a little time in the car as there are no real options in the neighborhood itself. Still, they're not far away. Whole Foods at Kahala Mall has everything the eco-minded and healthy eater could want. Almost next door to the mall is Times Supermarket, which stocks the more traditional types of food and groceries.

Shopping Alternatives
There's a lot of great shopping nearby, but again, they will require some driving. Then again, you might have so much to bring home that the car will be the only way to get it all there.

Kahala Mall – An elegant mall that's not overly large, but has more than enough to keep almost any shopper happy. Macy's, Long's and even Ross are here, along with boutique clothing and accessory stores. For leisure pursuits, there's a movie theatre and more than a few eating choices to sample.

Waikiki – The place to go for designer stores and where you'll find high-end restaurants with ocean views. Kalakaua Ave is the Pacific's Rodeo Drive, with the most prominent names in luxury items. Many Diamond Head residents are not much more than a stone throw away.

Hospitals & Health Care
Diamond Head is not one of the central areas for healthcare on Oahu. However, you're still in reach of the main hospitals toward Downtown as well as many doctors and specialists who practice from offices in Kahala and Kaimuki. These are the main medical facilities that serve your neighborhood.

Diamond Head Health Center – Focus is on HIV/STD and TB testing as well as Mental Health issues and treatment. Stands next to KCC 2 blocks from the back of Diamond Head.

Leahi Hospital – Services dedicated to patients who can no longer live independently. Offers residential care along with Day Care for adults who reside with family, but require monitoring during the day.

Queen's Hospital – Just on Diamond Head (east) side of Downtown, the major hospital in Honolulu. Full In & Out-Patient departments serving all ages. Also has mental health facilities and treatment.

Straub Clinic & Hospital – Near Queen's, Straub also has extensive treatment for Adults & Children. Mental health treatment available here, but not on In-Patient basis.

Your Recreation & Leisure Options
Diamond Head Beaches
Diamond Head is not as much of a beach community as an ocean view one. The areas on the ocean are often at the bottom of the slopes below Diamond Head Rd and are unreachable or have a landscape unfriendly to visitors looking for a place to relax. That said, we do have a couple of suggestions that you'll love.

Kaimana Beach – Actually in the borders of Waikiki, it's the last large beach this direction for some distance. Less tourists, dog friendly and good swimming, so residents love it here. So will you.

Diamond Head Beach Park – Heading east, the entrance to the walkway down to this beach is just past the lighthouse. It's not an extensive area and isn't good for swimming, but it is quiet, uncrowded and the outlook from here is wonderful. Prime surf spots are offshore as well. Parking can be hard as it's along the sides of Diamond Head Road.

Other Recreation
Due to the small area of this neighborhood, there aren't as many recreation options within it. You're right beside the playground of Waikiki, however, along with places to the east, like the smaller, but delightful parks in Kahala or even out to Koko Head and Hanauma Bay. We've got some excellent options for you below that are guaranteed to have you making return trips.

Diamond Head Hike – Maybe the most popular hike in Hawaii. Hard in places, but you're rewarded with a breathtaking look out at Waikiki, the ocean playing below and much of this part of Oahu. Good exercise rewarded. $1 per person, $5 per vehicle if you drive in.

Diamond Head Theatre – Hawaii's 1st performing arts center, it has put on plays & musicals since 1915. Numerous productions each year plus classes in acting, singing and dancing. Popularly known as the 'Broadway of the Pacific'.

Kapiolani Park – Vast park where, on any given day, open spaces become soccer pitches, volleyball courts, baby luau parties, cultural fairs and one of the best places to exercise in Honolulu. Not a bad site to relax, too. Tennis Courts across the road. The showcase park in all Oahu.

KCC Farmer's Market – The fresh produce, numerous food booths and tasty treats have exploded the appeal of this market. It now attracts a line of buses bringing Waikiki tourists to experience a slice of local life at this twice weekly event. A definite must-do, but go early as possible for the Saturday version to avoid the crowds and find parking.

Dining & Restaurants
This is undoubtedly one of the premier neighborhoods in the entire State, but one category it doesn't excel in is fine dining. That is due to the lack of available space, the cost, as well as zoning restrictions.

There is, however, Monsarrat Ave, where a whole collection of affordable and beloved eateries sit that you need to seek out. They may lack elegant place settings, but their flavors will keep you coming back. We've named some below, along with some places a little outside the district that are well worth the short trip, including a few high-end places.

South Shore Grill – Inexpensive and delicious. Diners love their mixed plates, the emphasis on fish, including fish tacos and mahi mahi, but chicken and beef dishes, too. Small, so take-out may be the way to go instead of waiting for a table to open.

Pioneer Saloon – Also on Monsarrat Ave. Despite the name it's all Japanese food. Sample the pork hamburger katsu and shiso rice, their most popular servings. Plate lunches, too, of course!

Diamond Head Cove Health Bar – Some say their prices are a little higher for the same offerings other places and service is sometimes slow, but no denying how much people love their acai bowls. Lots of healthy fare, like bee pollen, granola and other staples that go into different bowl items. The acai is the go-to, though.

Hawaii Sushi – One of the best deals in town. Not just for price, but the quality you get for it. The many different poke bowls are the main attraction, but there's a lot more to tempt you, too. Daily specials will keep you coming back.

Bogart's Cafe – Open from 6AM to 6:30AM, but can have lines anytime now due to its many fans. Early mornings are big here with many bagel breakfast sandwiches and distinctly local offerings like taro-banana pancakes. Lunch & Dinner focuses mostly on sandwiches as well as an excellent fried rice, but all meals are made of mostly or completely fresh ingredients. One Caution: Cash Only.

Diamond Head Market & Grill – Deli and restaurant in one, open from 6:30AM to 9PM. Come early and get their famous scones or stop by later in the day for the burgers and plate lunches that have an even bigger following. Fill up here and you'll thank yourself for stopping by.

Magoo's Burgers – Actually a food truck that's at 18th & Diamond Head Rd every day, 8:30AM – 4PM. Cheese and regular burgers are big and tasty, made for a post-DH hike meal. The shave ice is great for dessert or just cooling off the best way possible. Hiking or not, check this truck out.

Michel's – Found in the Colony Surf toward the DH end of Kalakaua Ave. Fine French cuisine served in their oceanside restaurant. A lot of the dishes are prepared by your table to add to the experience. Recommended highly for a sunset viewing with your special someone. Very high-end food and pricing.

Azure Restaurant (Waikiki) – Beachside restaurant at the Royal Hawaiian Hotel. Dine in your own cabana if desired on a primarily seafood menu, from lobster and mahi mahi to sashimi and ahi. Dress well and expect the royal treatment.

Yakiniku Hiroshi (Waikiki) – Top end place that some claim serves best beef in Hawaii. Full selection of different cuts and preparations, but waiters are glad to guide you. Some offerings not on the menu so ask what else is available. You cook it yourself at table and enjoy when ready!

Distances From Diamond Head to Other Parts of Oahu
Hanauma Bay: 8.5 miles
Hawaii Kai (Koko Head Shopping Center): 7.1 miles
Kahala Mall: 1.5 miles
Waikiki: 1 mile
Honolulu Airport: 10.6 miles 

Downtown Honolulu: 6.1 miles
Ala Moana Shopping Center: 3.4 miles
Pearl Harbor/Hickam: 12.5 miles
Pearlridge Shopping Center: 13.6 miles
Mililani: 24.2 miles
Kapolei: 25.9 miles
Kaneohe: 15.4 miles
Kailua: 17.2 miles
Lanikai: 17.2 miles
Waimanalo: 18.5 miles
North Shore
(Haleiwa): 34.8 miles
Sunset Beach: 42 miles

Diamond Head History
Diamond Head has always been considered sacred, in one sense or another, from the beginning. The old Hawaiians believed that Hiaka, sister of Pele, originally named the crater Pu'u Le'ahi because it resembled the head of a yellowfin tuna.

The Hawaiian priests later established a temple on its northwestern slope, called Papa'ena'ena Heiau. Fires lit here during rites could be seen from miles away. It was in this heiau that Kamehameha sacrificed Kiana, Oahu's Chief, after defeating him in the decisive Battle of Nuuanu. Kiana's skull was put on display here to underline that there was a new king in charge.

The heiau would be torn down in 1856 at the end of the kapu system and the ascension of Christianity in Hawaii. Yet the site's significance wasn't over. Beginning in the early 1900's wealthy kamaaina began building their homes in the Diamond Head district. One of the most wealthy and powerful, Walter Dillingham, erected his famous La Pietra estate on the very lands that Papa'ena'ena had inhabited. Change had certainly come.

The era of exclusive Diamond Head real estate arrived and has never looked back. Through 2 world wars, even as the crater's interior was carved into a military installation to ward off expected attack, the prosperous continued to erect real estate in Diamond Head that, though hidden from street view, were, and are, widely known for their luxury and beauty. It seems the threat of invasion isn't enough to keep out buyers of properties in Diamond Head.