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Diamond Head: A Guide

Diamond Head Crater, also known as Leahi in Hawaiian, is the iconic landmark and namesake of the Diamond Head area. With the hills of Saint Louis Heights to the west and the marine-protected area of Paiko Lagoon to the east, the Diamond Head area is known for its many neighborhoods and recreational activities. The Diamond Head area is convenient to downtown Honolulu and has a variety of schools, shops and restaurants, as well as community events. For those who work in downtown Honolulu, the commute from the Diamond Head area can range from five to 20 minutes, with many routes to choose from to avoid traffic delays. The Diamond Head area is enjoyed by long-time residents, celebrities and tourists alike.

What is the real estate market like in Diamond Head?

The Diamond Head area has many luxury single-family homes with lawns, as well as plantation-style homes, and condominiums along the Gold Coast and in the neighborhoods of Palolo and Kaimuki. There are remodeled and newly built homes, as well as homes dating back to the 1920s and 1930s. 

For-sale housing inventory in the Diamond Head area is typically low, so competition in the area is strong. When a house is listed for sale, it usually is under contract within a short time of being listed. The average single-family home and condo values in the Diamond Head area are some of the highest on Oahu. The Diamond Head neighborhoods of Kahala and Black Point are home to some of the most expensive real estate on Oahu

Iconic Diamond Head on the South Shore of Oahu

Diamond Head Fun Facts

From Livestock to Celebrities
  • Hawaiians once called the crater Leahi, which means “brow of the tuna.” Can you see the tuna’s dorsal fin shape on Diamond Head’s ridgeline?
  • Diamond Head was once home to roaming livestock and then Hawaii’s first military installation. Today, the Diamond Head area is known for its prime location near Waikiki and urban Honolulu.
  • In the 1970s, Diamond Head Crater once hosted a huge annual outdoor concert called the Sunshine Crater Festival that attracted more than 75,000 spectators.
  • Many celebrities have called the Diamond Head area home, including Jim Nabors, Daniel Dae Kim, Alex O’Loughlin and Hawaii waterman legend, Duke Kahanamoku.
Community Events
  • Diamond Head hosts numerous community events, including the weekly Kapiolani Community College Farmers Market.
  • The annual Honolulu Marathon route traverses the Diamond Head area, as do many other shorter races throughout the year.

Diamond Head Real Estate Drone Tour

Diamond Head Region Neighborhoods

The following breakdown of the Diamond Head regions sub neighborhoods were compiled by Locations agents who live and work in the area.

Diamond Head

Surrounding Diamond Head Road and including the landmark Diamond Head Lighthouse, this area contains several luxury homes, as well as homes in various conditions. Some homes along the beach have well-landscaped lawns fronting the beach. South of Diamond Head Road, the topography declines toward the ocean, giving homes near Diamond Head Road expansive ocean views. Diamond Head Road is a wide, busy street that is frequently used for races that occur throughout the year, including the Honolulu Marathon (the road is closed at least six times a year for events). View Diamond Head Homes for sale

Black Point

This outcropping of volcanic land, much higher than sea level, is adjacent to the ocean. Black Point has ​​two areas: The stretch of homes before the gated community along Black Point Road and the cluster of homes inside the gated community. ​​​The road is public up to the gated community. ​Homes on the public portion of Black Point Road are a mix of traditional Hawaiiana homes and large, luxury homes. Homes beyond the security gate are located on a peninsula that goes out into the ocean. Black Point contains a mix of a few large, modern homes and more traditional homes. This area is quite dense, and homes are mostly on smaller lots. ​Several homes have been restored. Homes have views of Koko Head and Maunalua Bay. ​​​​Homes in Black Point are either on septic tanks or cesspool, as connection to the public sewer system is not available, and there are overhead utilities and poles. Shore breezes are a factor, and salt spray will require constant maintenance of the property. ​At the far south point of Black Point is an undeveloped plot of volcanic land along the waterline that serves as a bird sanctuary for ​​Shearwater birds, who nest and raise chicks there. This volcanic rock area is about four to five acres, and it is a popular fishing spot, as the land rises 25 feet above sea level. View Black Point homes for sale

Kahala

Home to The Kahala Resort and Hotel, the Kahala neighborhood has some of highest-valued properties on Oahu. With around 1,000 lots, Kahala offers close proximity to shopping and beaches. There are about 60 beachfront homes in the Kahala neighborhood, which have access to some of Oahu’s best surf breaks and beaches. The neighborhood is a mix of older homes and larger new or remodeled mansions. Some homes date back to the 1920s and 1930s, when Kahala was first settled. The Kahala neighborhood has larger lot sizes, wide streets with sidewalks and multiple beach accesses. View Kahala homes for sale

Kahala Kua

Kahala Kua is a mountaintop gated community with panoramic ocean views and large landscaped yards. Most of these homes are newer. There are approximately 130 single-family homes in this private neighborhood with views that span from Koko Head Cater in Hawaii Kai to Diamond Head. View Kahala Kua homes for sale

Puu Panini

Puu Panini is a small neighborhood with a private park that includes tennis and paddleball courts for residents’ use only. Homes in this neighborhood were built in the 1950s, and there are only 27 homes available. These homes have large lots, and many have been re-designed by famous architects. Some of the homes have original features, while others have been remodeled, and all homes have large lots. This neighborhood is convenient to Kahala Mall, schools, the H-1 freeway and downtown Honolulu.

Kaimuki

Kaimuki offers single-family homes, along with some condominiums on Waialae Avenue. Kaimuki is known for its eclectic “mom-and-pop" shops along Waialae Avenue, which include restaurants, yoga studios, crack seed stores and more. View Kaimuki homes for sale

Aina Haina

To the mountainside of Kalanianaole Highway, lies this residential community with original and remodeled single-family hillside homes. There is an Aina Haina Community Association for the benefit of new and long-time residents alike. View Aina Haina homes for sale

Aina Haina Beach

To the beachside of Kalanianaole Highway, Aina Haina Beach has expansive homes, many with pools and large manicured lawns. Only a few lucky people can call Aina Haina Beach home, as there are limited lots available. View Aina Haina Beach homes for sale

Hawaii Loa Ridge

With a reputation as one of the most luxurious ridge neighborhoods on Oahu, Hawaii Loa Ridge homes have lots ranging from 8,000 to 30,000 square feet. This secluded gated-community is 1,000 feet above sea level. View Hawaii Loa Ridge homes for sale

Kai Nani

The upscale neighborhood of Kai Nani, east of Waialae Country Club, consists of about 30 homes with beachfront and golf course views. View Kai Nani homes for sale

Kapahulu

Loaded with restaurants, including the famous Leonard’s Bakery, Kapahulu Avenue is one of the main streets on the western side of the Diamond Head area. Along this strip, small condominium housing options can be found along with smaller single-family homes. View Kapahulu Homes for sale

Kuliouou

This mountainside neighborhood between Nui Valley and Hawaii Kai has a number of single-family homes. View Kuliouou Real Estate and Homes for sale

Maunalani Heights

Past the intersection of Sierra Drive and Wilhelmina Rise, below the Maunalani Community Park at the apex, lies this hilltop neighborhood with ocean views. View Maunalani Heights homes for sale

Niu Beach/ Niu Valley

This beachfront neighborhood is located on a peninsula between the neighborhoods of Aina Haina and Kuliouou and has less than 100 homes. Nui Beach offers easy access to the ocean, and King Kamehameha the Great once called Niu Beach home!  View Niu homes for sale   View Niu Valley Homes.

Paiko Lagoon

In East Oahu, almost to Hawaii Kai, this quaint neighborhood includes 20 oceanfront homes and a little more than 20 other homes on the brackish water of  Paiko Lagoon. There are a number of surf spots off of this neighborhood, including Paikos, Tuna Bowls and Turtles. View Paiko Lagoon Real estate

Palolo

Palolo goes deep into the hillside between the neighborhoods of St. Louis Heights and Kaimuki. There are a number of shops and restaurants close by on Waialae Avenue. Most homes are older, and the neighborhood is popular with first-time buyers and investors. View Palolo Real Estate and homes

Saint Louis Heights

This neighborhood with about 600 single-family homes lies along the steep hills overlooking Honolulu. Many of the single-family homes are older with long-time residents, with some built as early as the 1920s. At the base of the neighborhood is the Regency Park condominium complex, which has 272 units and is next to Chaminade University. View St. Louis Heights Real Estate for sale

Waialae Iki

Construction of this ridge neighborhood began in the 1960s. Some single-family homes offer views of Diamond Head Crater and Waialae Country Club.  View Waialae Iki Homes for sale   View Waialae Iki Gold Course homes

Waialae Nui Ridge

Drive along Halekoa Drive, and you will be greeted by a twisting road with expansive views. Single-family homes range from 6,000 to 13,000 square feet and enjoy temperatures that are about seven degrees cooler than down the hill. Some homes were built decades ago, while others are newer builds. View Waialae Nui Ridge Homes

Waialae Nui Valley

Along the roads of Waialae Avenue, Kilauea Avenue and Hunakai Street, there are some million-dollar homes with lot sizes between 7,500 to 10,000 square feet. There are also a few condominium and townhouse options in Waialae Nui Valley, including the high-rise Kahala Towers, Tropic Gardens, Tropicana Village Makai and Waialae Gardens. View Waialae Nui Valley Homes for sale

Wailupe Pennisula and Wailupe Beach

With a little more than 20 beachfront homes and another 120 homes on the Wailupe Peninsula, this small neighborhood is on the oceanside of Kalanianaole Highway. Once one of East Oahu’s largest ancient Hawaiian fishponds, it was filled in to make way for homes in 1947. Home lots range from 6,000 to 30,000 square feet, and homes often sell for multiple millions of dollars. Some of the homes have private boat docks, and Wailupe homeowners can live the Hawaii lifestyle with a community pier and boat ramp. View Wailupe Pennisula Homes 

Wilhelmina Rise

Up steep Wilhelmina Rise toward Sierra Drive is this popular family community. Single-family homes—some with expansive views--are in a variety of sizes and conditions. View Wilhemina Rise Homes for sale

Iconic Diamond Head on the South Shore of Oahu

What is there to do around Diamond Head?

Diamond Head Events, Entertainment and Attractions

There is a lot to do in the Diamond Head area, with many nearby attractions, as well as weekly and annual events. Join a running or biking race or take part in a community event, like the weekly KCC Farmers Market. Living in Diamond Head makes it easy to stay active and enjoy various entertainment options.

  • Kapiolani Community College Farmers’ Market. 4303 Diamond Head Road. Every Saturday and Tuesday, locals and visitors alike gather to enjoy fresh-cooked food, flowers and produce. This is one of Oahu’s largest and most popular farmers markets.
  • Doris Duke Museum. 4055 Papu Circle. Also known as Shangri La Museum of Islamic Art, Culture and Design, this former home of heiress Doris Duke is operated as a museum by the Honolulu Museum of Art. Enjoy unique architecture and beautiful oceanfront views.
  • Diamond Head Lighthouse. 3399 Diamond Head Road. While this iconic structure is closed to the public, it can be viewed off Diamond Head Road. It was built in 1917 and stands 55 feet tall. It is on the U.S. National Register of Historic Places.
  • Diamond Head Theatre. 520 Makapuu Avenue. This theatre is tucked into the heart of Diamond Head neighborhood and is a popular place to enjoy live entertainment.
  • Honolulu Marathon. Taking place each December, this 26.2-mile race is the fourth-largest marathon in the U.S., attracting thousands of athletes from around the world. With no time limit, anyone can partake in the race, which cuts through the shoreline of the Diamond Head neighborhood.
  • Honolulu Zoo. 151 Kapahulu Avenue. Visit this popular zoo with diverse animals, both big and small, including lions, lizards, flamingos and more.
  • Waikiki Aquarium. 2777 Kalakaua Avenue. See a plethora of marine life along the oceanfront of Diamond Head. Take a look at the jellyfish, seals and tropical fish, and then visit the unique gift shop afterwards.
Shopping and Movies

The Diamond Head area offers a variety of retail and entertainment options for almost all of your needs. Shopping centers, movie theaters, Whole Foods and more making living in Diamond Head convenient, easy and fun. Here are the main shopping centers in the Diamond Head area and neighboring Waikiki:

  • Kaimuki Shopping Center. 3221 Waialae Avenue. Kaimuki Shopping Center has groceries and more for Diamond Head residents with banks, a Longs Drugs, Times Supermarket, restaurants, and more.
  • Kahala Mall. 4211 Waialae Avenue. Located in Kahala, this is one of the main malls on Oahu, with a Whole Foods, Macy’s, restaurants, boutiques, a movie theater and more.
  • International Market Place. 2330 Kalakaua Avenue. This shopping center in Waikiki has more than 80 restaurants and stores, including Anthropologie, Saks Fifth Avenue and more. Multiple events, such as lei-making, yoga and hula, add to the entertainment options of the enchanting center.
  • Royal Hawaiian Center. 2201 Kalakaua Avenue. Enjoy shopping with some of Hawaii’s most well-to-do tourists while exploring Royal Hawaiian Center’s restaurants and shops, which include from luxury brand shops to local Hawaii boutiques.
  • Ala Moana Center. 1450 Ala Moana Boulevard. Ala Moana is the Hawaiian Islands’ number-one shopping and entertainment destinations, and is rated as one of the best in the U.S. Ala Moana has department stores, trendy local boutiques, a bowling alley, a spa, restaurants, food courts and much more.
Parks

Diamond Head parks offer expansive fields, tennis courts, areas for dogs and more.

  • Diamond Head Bark Park. Diamond Head Road & 18th This park is a doggie paradise with a water fountain, well-maintained grounds, bags, mini park for small dogs and lots of parking.
  • Fort Ruger Park. 534 Paikau Street. Commonly known as Triangle Park, this quaint park with green grassy areas and large trees once served as the first military reservation in the Hawaiian Islands and is now a tranquil spot to rest.
  • Fort DeRussy Beach Park. 2161 Kalia Road. Open to military personnel and civilians, this park fronts popular Waikiki Beach and rents ocean supplies. The shallow and calm Waikiki water makes it a beautiful place for the whole family.
  • Kaimana Beach. 2863 Kalakaua Avenue. This Diamond Head beach park is a popular spot for BBQs and ocean fun.
  • Kaimuki Community Park. 3521 Waialae Avenue. Kaimuki Community Park is in the center of the of Kaimuki neighborhood and has basketball courts, an indoor gym, playground and more.
  • Kapaolono Community Park. 701 11th Kapaolono Community Park is a large park with a swimming pool, basketball courts, tennis courts, fields and facilities.
  • Kapiolani Park. 2840 Paki Avenue. This iconic Diamond Head park was once home to polo fields and loved by Hawaii royalty. There is plenty of parking, along with vast open fields, tennis courts, workout equipment and restroom facilities. Across the street from the park is the edge of Waikiki Beach.
  • Kilauea District Park. 4109 Kilauea Avenue. With a big gym, fields, tennis courts and more, Diamond Head residents can exercise in this park that’s adjacent to Diamond Head Memorial Park.
  • Petrie Community Park. 1039 20th Petrie Community Park has open fields, a playground and basketball courts, across from Waialae Elementary School.
  • Puu O Kaimuki Mini Park. 951 Koko Head Avenue. This quiet park has beautiful views of Kahala, Honolulu, Manoa and Hawaii Kai.
  • Waialae Beach Park. 4925 Kahala Avenue. This small oceanfront park is the perfect place to watch the sunset or enjoy a picnic. You might also see kayaking, fishing or surfing off the shores.
 Diamond Head crater and neighborhoods
Golf

The Diamond Head area offers a few golf courses.

    • Ala Wai Golf Course. 404 Kapahulu Avenue. This popular and economically priced public 18-hole golf course next to the Ala Wai Canal has club rentals.
    • Waialae Country Club. 4997 Kahala Avenue. Almost 100 years old, this breathtaking country club is home to the annual Sony Open. The beachfront course is well-maintained, and the private club offers a pool, restaurant, event space and more.

Surfing Diamond Head

What surf spots are at Diamond Head?  

  • Diamond Head. Off Diamond Head Road by Diamond Head Beach Park. Down Diamond Head’s slopes, there are several reef breaks, including Mansions, Cliffs, Lighthouse and others. Waves typically are best during south swells and north winds.
  • Cliffs.  Fun lefts and right directly down the Diamodn Head trail.    Very popular and easy surf spot.   Get windy in the afernoons every day almost.
  • Queens.  Past the Duke statue. This is a consistent wave that breaks both left and right. At Queens, you will find both professional surfers and beginners. It’s loved by longboarders.
  • Walls.  Park at the zoo. By the pier at the zoo-end of Waikiki. You will see experienced surfers and bodyboarders here.
  • Tongs. Through the neighborhood south of Diamond Head Road near Kapiolani Park. Breaking left and right; for intermediate to advanced surfers.
Hiking

The Diamond Head area has come of Oahu’s most popular hikes.

  • Diamond Head Trail. Parking at Diamond Head State Monument. Wear comfortable shoes and bring water. This two-hour hike offers a beautiful panoramic view of Oahu.
  • Lanipo and Mau‘umae Trails. A dirt path starts off Maunalani Circle. For advanced hikers, this ridge hike reaches high altitudes and has rough terrain.

Views from Diamond Head's Pillbox Hike with Kapiolani park below Diamond Head pillbox hike and KApiolani Park below


What is the History of the Diamond Head?

This iconic crater at the edge of Waikiki is known as Leahi (“brow of the tuna” in Hawaiian) and Diamond Head, a name it received in 1825. At that time, British sailors thought that they had found diamonds of the crater’s slopes, but these rocks were actually volcanic calcite crystals that shined in the sunlight. After being used as military reservation Fort Ruger, Diamond Head was named a U.S. National Natural Landmark in 1968. Its trails are now enjoyed by tourists and locals, but there still are some military uses in place, including U.S. government antennas on its slopes. Diamond Head Crater is also home to a National Guard emergency operation center and Hawaii State Civil Defense Headquarters.

In the inland hillier parts of Diamond Head, stories of Menehune, or small mythical creatures, who built tī leaf ovens overnight in the Diamond Head area are prevalent. In fact, the name Kaimuki, one of the larger neighborhoods in Diamond Head, originates from the Hawaiian words ‘ka imu kī,’ which together means 'tī oven.

The hills of Diamond Head were mostly undeveloped until the early 1900s. Kamehameha I used Diamond Head as a lookout to see enemies coming from the ocean. In 1884, Dr. Trousseau, King Kalakaua’s physician, won 324 acres in Diamond Head for a reasonable auction price of $2,325. In 1887, he gifted land to businessman Daniel Isenberg, who used it for his Waialae Ranch. Cattle and racehorses once walked what is now the Waialae Golf Course area for about ten years during that time.

The Chinatown fire in 1900 spurred for the development of the Diamond Head neighborhood. The fire left many immigrants homeless, and many headed to the Diamond Head area for a new start. In 1898, Theodore Lansing and A.V. Gear purchased the land from Dr. Trousseau and sold small lots, which created Honolulu’s first subdivision. Into the 1920s, more people moved to the Diamond Head area and purchased plantation-style homes on Waialae Avenue and up into the mountains.


Restaurants

Restaurants in Diamond Head include options from almost any cultural cuisine you could imagine, as well as trendy local eateries.

  • Diamond Head Grill. 3158 Monsarrat Avenue. A long-time Honolulu favorite, Diamond Head Grill serves local-inspired plate lunches and dinners, along with delicious desserts. 
  • Arancino at The Kahala. 5000 Kahala Avenue. Located in The Kahala Hotel and Resort, Arancino is a chic Italian restaurant, serving refined lunches and dinners.
  • Koko Head Café. 1129 12th A café serving decorative and delicious brunch dishes. Popular dishes include the banana Chantilly pancakes and the short rib loco moco.
  • Rainbow Drive-In. 3308 Kanaina Avenue. Open since 1961, this iconic restaurant serves local plates from 7 a.m. to 9 p.m.
  • Mud Hen Water. 3452 Waialae Avenue. With a hip, trendy vibe, this restaurant serves small dishes with local ingredients and mouthwatering cocktails.
  • Saigon’s Restaurant. 3624 Waialae Avenue. This popular spot serves both eat-in or take-out Vietnamese food, including spring rolls, pho and other popular Vietnamese dishes.
  • Hawaii Sushi. 3045 Monsarrat Avenue, Ste 1. Located near Kapiolani Park, this restaurant serves a variety of 'ono sushi options along with sashimi, udon, tempura and more.
  • Tenkaippin Ramen. 617 Kapahulu Avenue. Open for dinner, this vibrant ramen shop is a great place to satisfy cravings and relax by the bar.
  • Asuka Nabe + Shabu Shabu. 3620 Waialae Avenue. Select your soup and then add your vegetables, meats, noodles, rice and sauces for a unique dinner.
  • Shaloha Pita. 3133 Waialae Avenue. This is a popular Middle Eastern food place with falafel, pita, tabbouleh and other favorite dishes.

Recently Sold

  • Sold on 5/23/2024 for $1,250,000 5974 Kalanianaole Highway 6 Bd | 5 Ba | 2,724 sqft
  • Sold on 5/22/2024 for $2,995,000 1029 Makaiwa Street 4 Bd | 3 Ba | 2,477 sqft
  • Sold on 5/22/2024 for $2,650,000 5119 Palaole Place 5 Bd | 4 Ba | 2,283 sqft
  • Sold on 5/22/2024 for $5,350,000 4921 Kalanianaole Highway 4 Bd | 4 Ba | 3,714 sqft
  • Sold on 5/20/2024 for $1,170,000 2252 Palolo Avenue 4 Bd | 2 Ba | 1,584 sqft
  • Sold on 5/17/2024 for $3,117,000 629 Ulili Street 5 Bd | 5 Ba | 4,476 sqft
  • Sold on 5/17/2024 for $999,999 2957 Kalakaua Avenue, 418 1 Bd | 1 Ba | 425 sqft
  • Sold on 5/17/2024 for $1,540,000 1904 Iwi Way 3 Bd | 2 Ba | 1,196 sqft
  • Sold on 5/15/2024 for $495,000 2877 Kalakaua Avenue, 202 0 Bd | 1 Ba | 351 sqft
  • Sold on 5/15/2024 for $570,000 3731 Kanaina Avenue, 341 1 Bd | 1 Ba | 483 sqft
  • Sold on 5/14/2024 for $3,290,000 931 Onaha Street 4 Bd | 3 Ba | 3,082 sqft
  • Sold on 5/14/2024 for $2,429,000 1431 Kamole Street 4 Bd | 3 Ba | 2,339 sqft
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