Honolulu owes its existence to one crucial piece of geography – its harbor. It’s true that Native Hawaiians lived across Oahu for as much as a thousand years before the town began to take its shape. However, they lived in widespread communities whose centers changed according to where the Alii were at any one time.
That would change forever in 1793 when sea captain William Brown, a fur and gun trader, realized the harbor was deep enough for large ships to dock. Soon the land nearby was filled with shops and businesses catering to the whaling ships and trading vessels who increasingly stopped here. Neighborhoods sprang up quickly as well to house those attracted by the booming industry. A city had been born.
Honolulu’s harbor’s focus would change from whaling to the local sugar and pineapple products in the late 1800’s. The need for plantation workers brought men, and later women, from Asia and Europe, arriving through this same waterfront. Many of them would fulfill their obligations on the farms, then move to urban Honolulu to take advantage of the job opportunities there or start their own businesses.
The plantation economy was joined in the early 1920’s by the tourism industry, the cruise ships finding their berths in the piers near where ships loaded with goods were going in and out of Hawaii. The contents of the ships was changing, but the effects were the same. Though the plantations would become almost extinct before the end of the 20th Century, Honolulu was set in place.
Honolulu’s History by Neighborhood
Debate rages over how Aina Haina got its name. Some believe it is rooted in ‘Haina’ as the Hawaiian word meaning ‘sacrifice’. The presence of the ancient Kawauoha Heiau deep in the valley, believed to have been the site of human sacrifice, strengthens the case.
Another, more popular story, is that ‘Haina’ is also the Hawaiian translation for ‘Hind’, which was the name of the dairy farm, and its owner, that took up much of this district; Aina Hina = Hind’s Land.
Robert Hind established the Hind-Clarke Dairy on this real estate in 1924, the business continuing here until 1946. Robert died in 1938, but his family carried on, ultimately selling the dairy operation in the late 1940’s.
Aina Haina Beach
Kawaiku’i isn’t just the name of the park on the eastern side of Aina Haina Beach. It was also the name used by the ancient Hawaiians for an area that included both. Kawaiku’i, translated, means ‘the united water’. Some believe the name arises from the fact that so many came, both locals and passers-by, to get fresh water from the springs here. Another story says the name was given because the fresh and salt water met, or united, here.
Outside of fishermen, this was not a heavily populated area for hundreds of years. This condition extended into the 20th Century when Robert Hind bought a large acreage that took in all of Aina Haina, up to the ocean, for his Hind-Clarke Dairy operation. The dairy farm was well known in Honolulu and supplied much of the milk and dairy products for the town.
Declining fortunes and the devastation from the 1946 tsunami compelled the Hind family to sell the dairy business and switch to developing their real estate holdings. They chose the right time, with the post-World War II era setting off a demand for housing that was unprecedented.
Aina Haina Beach homes first went up at this time on the exquisite oceanfront lots that had been mostly bare all these years. Residents and visitors can still see freshwater springing up from the sands at times.
Before those Ala Moana condos towered over the equally imposing shopping mall, this was once a very different place. Not only did it have another name, ‘Kalia’, it was also mostly swampland with some scattered taro patches. A place that, for centuries, mainly fishermen lived.
In 1912 Hawaiian Dredging, owned by Walter Dillingham, bought land here for the dumping of coral, sand and dirt from their projects around Oahu. This filled in much of the wetlands and ponds, creating solid ground, much of which became Ala Moana Park. The area set aside for the park was officially dedicated in 1934, in part by President Roosevelt.
The next couple of decades saw small homes becoming more numerous nearby, but nothing that could be called a real neighborhood. It was purely a low-rise, low density district. That would drastically change with the coming of Ala Moana Center.
Envisioned as early as 1948 by Lowell Dillingham, Walter’s son, it wouldn’t be until 1957 that Hawaiian Dredging actually began building on what had been bare land. Ala Moana Center was finished and opened with great fanfare in 1959, coinciding with the advent of Statehood. The center’s impact on the surroundings was immediate.
Black Point real estate, like all of Hawaii, began life as a result of volcanic eruptions. Though it sits just beneath the famed Diamond Head, it came from a different eruption as that landmark, but around the same time.
The formed land ended in black lava rock that sloped down to the ocean, giving it the name we know it by today. The ancient Hawaiians, however, called this area Kupikipikio, which means ‘Rough Sea’ for the waves that constantly crash against these slopes.
In 1910 the US Army placed a small battery here as part of their plans for Oahu’s defenses against invasion. The guns were intended to protect searchlights, in case of a night attack, as well as to provide other cover. They didn’t remain long due to changes in defenses and strategies.
From the early 1920’s, when homes on Black Point were first built, they were very exclusive residences. The ocean views and seclusion from the rest of the Island attracted the wealthy, as well as the famous, immediately. Most significantly, Doris Duke built her Shangri La estate here, an achievement of architecture and design that still dazzles present day visitors now that it is a museum.
Duke Kahanamoku, Tom Selleck and numerous other famous names have been residents over the years. When news columns cover a visiting celebrity, it’s often noted that they’re staying here, due to the privacy and luxury Black Point homes afford. It was noted recently that Johnny Depp was vacationing in the neighborhood, for example.
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.
The first residents of Honolulu were Polynesians who found a home here as early as the 11th Century. For generations they led a quiet agricultural life, interrupted periodically by conflicts between local chiefs. This existence was completely upended by the 1794 arrival of the 1st European ship in Honolulu Harbor, changing this place into a bustling international port.
In the early 1800’s, though, Honolulu lacked any real city structure or planning. Some felt the old land system wasn’t a solid basis for the growing economic activity. The Hawaiian concept of land use at the pleasure of the Ali’i was increasingly under attack as merchants & businessmen sought private ownership.
Under pressure, a Board of Commissioners was set up in 1844 to hear testimony and begin making land grants. It was through this process that Downtown Honolulu took solid shape with formal streets designated and lots laid out.
The district near the harbor grew quickly, taking on even more significance when this was made Hawaii’s capital in 1845. The Downtown area, especially around Fort St, was Oahu’s primary shopping district until the 1960’s, only losing that status with the opening of Ala Moana Center.
The accelerating population growth brought on by the end of World War II and Statehood produced a boom in building larger and larger commercial and residential buildings. The mounting demand for business space and new zoning are why you find today’s downtown Honolulu condominiums primarily on Nimitz Hwy or the mauka side of Beretania St.
Condos in downtown Honolulu are still in demand for the same reasons residents flocked here in the 19th Century. They sit in the business and government center for not only Oahu, but all Hawaii, while gazing out over a waterfront that never fails to fascinate.
The earliest settlers to come here are believed to be from the first great Polynesian migration around 947AD from the Marquesas, fleeing tribal conflict at home. For centuries following this time, life was very quiet on this part of Oahu. Fishing was the primary way of life until well into the 1800’s.
The family of Princess Bernice Pauahi Bishop were given ownership of all the land of Hawaii Kai under the Great Mahele division in 1848. Through that, the possession passed on to the Bishop Trust after the Princess’ death in 1884.
In 1900 cattle ranching was established here, becoming a primary industry, on land at least. For decades this was a prime mover of the local economy, but it met a sudden end that it never recovered from. The 1946 tsunami hit this area hard, wiping out houses, barns, fields and everything else in its path.
Hawaii Kai homes that did survive were abandoned and the land turned to swamp. The district became known mainly for a strong smell that motorists from downtown drove quickly through on their way to a popular spot called Lucky’s Tavern. That’s how it stood for 15 years.
Henry Kaiser signed the land lease with the Bishop Estate in 1961, breaking ground on the community that you see today on your way down Kalanianaole Highway. The marina was dug out, new real estate in Hawaii Kai went up and shopping malls opened, forming a charming waterfront neighborhood that erased the remains of desolation.
One thing hasn’t changed, though. The fishing in Hawaii Kai is still great!
Hawaii Loa Ridge
For a place where homes sell so easily, it’s been very difficult to get where they are now. The story of Hawaii Loa Ridge homes starts with Kamehameha I and his gift to Alexander Adams of large tracts of land that included these heights. Adams’ service as head of the Hawaiian Navy had won him this great honor.
Until the early 1900’s little was built up here due to the difficulty of traveling up and down these hills. One of the very few houses, put up in the 1930’s by Adams’ descendants, not only still stands today, it remains under family ownership.
The growth of the population led to a booming development era starting in the 1950s. Hawaii Loa Ridge, however, wasn’t eyed by builders until the 1970’s. An access road up the ridge was started with great optimism. Unfortunately, only partway up it became clear it was too expensive just to build this road. So plans came to a screeching halt.
The 80’s decade saw a new developer, HMF, step in to try their luck. They also stumbled as interest rates rose to double digits and the market went soft. The buyers who did remain saw their Hawaii Loa Ridge homes sit lonely, with empty lots all around them. It looked like another plan was unraveling.
Somehow HMF stuck it out. The Hawaii market did finally rebound and now this is an exclusive neighborhood known for incredible views and quiet contentment. Sometimes enjoying the fine life takes a lot of hard work.
When Kamehameha the Great made his assault on Oahu, many of his canoes made their landing at Kahala, beginning what would be his most famous campaign in uniting the Islands. That same year, 1795, Native Hawaiians began settling here, starting the first known communities.
Some agriculture activity did go on, but most concerns were pig and cattle farms throughout the 1800’s. Following the 1848 Great Mahele land division, all of Kahala came under the ownership of Princess Bernice Pauahi Bishop. Her death transferred those lands to the Bishop Estate Trust, where much of still remains.
The modern Kahala real estate is a product of the upper classes ‘discovering’ it after World War I. Ponds were filled in, farms were shuttered and mansions started to grow along the beachfront. One attraction may have been that Kahala is completely flat, a rarity on Oahu.
Homes in Kahala have since been the residences of many of the best connected kamaaina, but even they haven’t been able to control everything in their neighborhood. The building of the Kahala Hilton in the early 1960’s had much opposition from residents, including numerous high-profile families. The rezoning required was still approved by the City Council despite both a planning committee recommendation and a mayoral veto.
One short-term victory they did win was the ability to buy the land their houses stood on from the Bishop Estate. The last lots, all beachfront, were converted from leasehold to fee simple in November of 1986. The Kahala homes that have title to their land do so because of that window of opportunity.
Ultimately, this place is a true Cinderella story. The land once dominated by pig farmers, in a few short decades, turned into the playground of the world’s rich and famous. Quite a rise.
Most students of Hawaii real estate history, and its conflicts, forget that Kai Nani was actually part of one of the biggest fights of all. The struggle began when a hotel was proposed to go up in the quiet, and very upscale, neighborhood of Kahala. This was seen as nothing short of an enemy invasion to the well-heeled residents and they were ready to fight it.
Though victory seemed to be in their grasp, with a special committee recommending a rejection and a mayor prepared to veto any such measure, it was not to be. The City Council passed the rezoning needed and then overruled the mayoral veto.
The Bishop Estate, who owned all the land in Kahala at that time, then added salt to the wound by taking back land from the Waialae Golf Course, including oceanfront property that would now contain a resort. That wasn’t the end of it, either.
Waialae Golf Course would be completely reconfigured to fit the new layout. They would also relinquish a piece of land on the southeastern side in the bargain. Enough to fit 30 houses.
Kai Nani homes sit there now, complete with fairway and ocean views, a few on the oceanfront itself. Somewhere under those paved roads and the beautiful Kai Nani homes lie the remains of the 6th and 7th holes of the old Waialae Golf Course.
Stories abound from the old Hawaiians about Menehunes, a race of small beings who could build huge structures overnight. It was this part of Oahu that was believed to be where these magical people made their ti ovens, which in Hawaiian are translated as Kaimuki. So these lands were named.
Very little was done on or with this hilly property until 1887 when a man name Daniel Isenberg used a large area for a cattle ranch. He also raised racehorses here that ran at the Kapiolani Park track, a place very popular with King Kalakaua.
The turning point that made Kaimuki a true residential neighborhood, though, was the 1900 Chinatown fire. Many of the Chinese who were left homeless by that fire moved here to make a new start, creating what was Honolulu’s first major subdivision. There were more to come, however.
Kaimuki homes experienced even greater growth when the streetcar routes were extended out to this area of Honolulu in the 1920’s. The many who work downtown could now live further out and still commute every day to their jobs. A second, larger population wave now made its way here, buying up lots and settling down.
Residents established a small-town feel on these streets, lining the main drag of Waialae Avenue with many local business and restaurants. Take a walk around here and you’ll still find those awaiting you, along with charming homes that now hold the latest generations from those early 1900’s migrations. It’s that kind of community.
The Kakaako district is in the midst of a modernization that will leave it unrecognizable to its original inhabitants of old. Where towering Kakaako condos are going up was once a vast Native Hawaiian agricultural community that practiced terrace cultivation. Many of the ali’i had homes here, including Kamehameha I.
It was also the port site for foreign ships that came to Honolulu for trade and supplies. In 1850 those sailors brought with them smallpox, which decimated the nearby population. By this time the Kakaako community had grown due to the activity around the port, making the crowded district the perfect place for disease to spread. The bones of the tragic victims are often found whenever construction is done here.
Though the neighborhood experienced a resurgence that lasted into the 1950’s, things changed once the zoning was altered to allow more commercial activity, attracting more and more businesses that took the place of homes. Body shops and industrial work particularly stand out on these streets.
Times have changed once again as Kakaako condos have gone up, soon to be joined by many more. Though they are the future of this neighborhood, in many ways they bring back its past, when this was a truly thriving home to so many.
Translated, Kapahulu means ‘worn out soil’. Luckily that doesn’t truly describe this vibrant part of Honolulu. The land it sits on was part of the holdings given to King Lunalilo during the Great Mahele, which turned over land to private ownership for the very first time.
Though private residences are recorded as early as 1889, this area remained mostly undeveloped and untouched until the 1920’s when the streetcar system made it accessible for those who worked in town. The Japanese especially congregated here to affordably escape the crowded conditions downtown.
Due to the unplanned quality of this neighborhood, houses here were of a wide variety of styles, reflecting the tastes of individual owners. The UH History department has tried to document what are now historical structures here, finding everything from Art Deco & Moderne to even Tudor and Mission style buildings, alongside plantation homes, of course. So you often have a choice of genres when shopping for homes in Kapahulu.
Despite being next door to Waikiki, this neighborhood has held onto its local identity & history. Rainbow Drive Inn, Ono Hawaiian Foods and Leonard’s Bakery are just 3 of the institutions that have served generations of residents. Kapahulu homes and buildings remain defiantly low-rise, outside of a few condos on the Ewa (west) side of Kapahulu Ave.
Here the old Hawaii still lives, a place you can grab some real shave ice, get your surfboard repaired and talk a little story.
The Makiki neighborhood’s history is an intriguing mix of the Honolulu elite and the lower classes, specifically former plantation workers who had moved on to seek another livelihood. The community did not truly emerge until the early 1900’s as Japanese, Chinese & others finished their obligation to the plantations and began moving to this 2 mile area between Manoa & Downtown to start their own businesses or at least get better paying jobs. This wasn’t a place where just the aspiring classes owned real estate, though.
This same neighborhood was also the site of Punahou School, an institution that had taught the children of Hawaii’s political & economic elite since 1841. Many of the students’ families lived right nearby. Side by side, the residents of Makiki homes were a broad mingling of the classes that existed in few other places in Honolulu.
Today you still see these roots of this integration alive in Makiki’s plantation style homes that are still there or in the small, family run shops & businesses along School St. It is fitting that President Obama came from this neighborhood, attending the, still today, upper class Punahou School, though he came from a family that was not. His story is truly Makiki’s.
In Ancient Hawaii, Manoa lands were strictly divided between the Ali’i and the commoners. 2 hills, one at the head of the valley and the other above Punahou, were recognized as the borders between them. Interestingly, the waste from the ali’i lands were periodically taken to the commoner side and buried in secret.
The almost daily rainfall in this valley made it a prime agriculture area early on. Many crops were grown here by the Hawaiians and, in the 1800’s, it was the site of the Islands’ first sugarcane and coffee plantations.
The consistently cool weather also made it a prized retreat for royalty. Queen Kaahumanu, wife to King Kamehameha I, had a beloved home in Manoa. When she realized the end of her life was nearing, she insisted that she be taken there to spend her last days.
The modern neighborhood didn’t arise until the Honolulu streetcar system began running here in the 1920’s. Mid-Pacific School specifically chose the site they still occupy today because of the public transportation factor. Manoa real estate and residents followed suit, filling in what were mostly farming lands and empty lots up to that time.
Manoa homes are well-known for their refreshing breezes and greenery that grow freely from the rains. Coffee and sugar have vanished from the land, but the allure that drew the ali’i to the valley is as strong as ever.
Niu Beach real estate, like much of the surrounding land, was part of the grant by King Kamehameha to Scotsman Alexander Adams. This was a recognition of his service Hawaii as head of its Navy. It was clear that Kamehameha was showing special favor to Adams because the king himself had a summer home here next to the ocean.
This grant gave Adams control not only over the lands, but also the fishing rights in the waters immediately off of them. This was extremely important for areas like the Niu district, because of the fishponds built by the Native Hawaiians to provide a steady food source.
One of the largest on this side of Oahu, Kupapa fishpond, sat in this place, extending out into the ocean. It was walled in on 3 sides with the 4th marked by the shore. For hundreds of years it was tended and cultivated, well into the 1st half of the 20th Century. With modernization and new sources of food available, and affordable, the fishpond’s importance declined.
In the 1950’s Adams’ descendants decided to fill in the pond, using Hawaiian Dredging to do the job. Some small scale agriculture was briefly done on the newly created soil, but the intention was always to develop it for residential purposes.
Niu Beach homes were not long in coming. It’s not difficult to understand why Kamehameha the Great came here himself to unwind and relax. Simply said, own a Niu Beach home and you’ll live in a place fit for a king. Literally.
Most of today’s Niu Valley real estate originated from just one man – Alexander Adams. A Scottish sailor, he arrived in Hawaii around 1810, soon becoming friends with King Kamehameha I. The king recognized his nautical talents and soon made him the head of the kingdom’s navy.
Along with this charge he was given 2,000 acres in Niu Valley to both live on and farm. So he did. For the next 140 years Niu Valley was covered by vast cultivated fields as well as, for the first half of the 1900’s, a large dairy farm.
It was Adam’s granddaughter who decided to subdivide and sell the land finally in the 1950’s as the postwar Honolulu population began to boom. The ponds were filled in and the farms closed down in recognition of the changing times. Housing was needed and farming wasn’t as profitable any more.
Homes in Niu Valley quickly sprang up, both in the valley proper and on stunning oceanfront lots built over the site of an ancient Hawaiian fishpond. Adams’ estate today is a warm, close-knit neighborhood still watched over by the beautiful, green Koolau mountains just as they were when he first set foot on the Islands.
Pacific Heights real estate was originally the creation of a flamboyant man named Charles Desky in 1899. Newspapers noted that he had bought 450 acres of untouched land from Charles Booth and would be building houses immediately on it.
To promote the lots he established Hawaii’s first electric railway which took the curious from downtown Honolulu up 900 feet on Pacific Heights where a dance pavilion had been built. The idea was to entertainingly introduce potential buyers to the view from what could be their future home.
Unfortunately, Desky wasn’t a good businessman. Few houses were built when the original owner, Charles Booth, foreclosed in 1903. It seemed that mortgage payments hadn’t been made for 2 years. Some lot buyers actually lost their property in the process because Desky hadn’t recorded their deeds. Wisely, Desky soon left town for Shanghai, China.
Not until 1921, when the Honolulu government took over the hillside’s water system and automobiles were common, did Pacific Heights homes begin to take off. 20 years late, Desky’s vision of the upper class community finally became a reality. Vast mansions and estates sprang up on the land as the moneyed class saw the advantages of these properties.
The influential and successful continue to live on this rise, the home prices usually climbing along with the altitude as you drive upward. Somewhere out there, Charles Desky is saying ‘I told you so’.
Manuel de Pico did not start life with distinction. Born into a poor Portuguese family on the Azores Island of Pico, not much is known of his early history until he jumped ship in Hawaii from a whaler he was serving on sometime in the 1840’s.
The love for his newfound home compelled him to make a significant change. Somewhere along the line he altered his last name to make it more Hawaiian in tone, turning it into Paiko.
Through hard work and determination he made a success of himself in cattle raising on Oahu. One of the fruits of these profits were 400 acres of land he purchased past Diamond Head where he made his home.
The Paiko family continued to live here after Manuel died in 1890, their prominence & ownership recognized in naming the lagoon and the road nearby. The last Paiko, Joseph, Jr. died childless in 1947, bringing an end to the family’s vast landholdings.
Joseph’s passing opened up Paiko Lagoon real estate just as home construction boomed in Honolulu. The privacy, natural beauty and ocean views attracted wealthy buyers looking for a piece of true paradise. While other neighborhoods brag about having homes designed by Vladimir Ossipoff, only Paiko Lagoon can claim it is where the celebrated architect chose to build his own house.
Homes in Paiko Lagoon continue to carry top price tags, on the rare occasions they are for sale; but the wait, and the money, just might be worth it.
This part of Oahu was once the site of ancient Hawaiian fishing spots, which they kept secret and passed on through generations. Now it is an upscale neighborhood named for Nathaniel Portlock, a member of Captain Cook’s crew for his 3rd, and last, voyage. Portlock returned to Hawaii as the captain of his own ship, becoming the first European to sail into Maunalua Bay.
He only did some brief trading with the islanders, but did record that this part of Oahu was not well populated, probably due to a lack of freshwater sources.
Portlock has been prime real estate for some time due to the vista of both the bay & Diamond Head residents enjoy. Still, most of the original Portlock houses weren’t built until the 1940’s & 50’s. What put it truly on the map, though, was Henry Kaiser’s arrival in Hawaii during the later phase of that development.
Built to please Mrs. Kaiser, it featured a pink mansion plus 2 oval houses to hold her many pink poodles. In the greenhouse? Pink roses. The Kaisers entertained a constant stream of celebrities here, filling the society pages on a weekly basis. The Kaisers may no longer be with us, but the allure of Portlock’s real estate hasn’t diminished one bit. After them, this neighborhood had a new, high profile that it still enjoys.
St. Louis Heights
It’s obvious that this district got its name from St. Louis School, which sits on the lower end of the elevation. Created in 1846 to serve the Catholic community of Hawaiian kingdom, it counts Governor John Burns and the recently sainted Father Damien of Molokai as graduates.
The school moved to its present site from downtown Honolulu in 1928. 204 hillside acres were purchased from Bishop Estate, giving them not only enough for their school, but also to sell of as residential lots. 80 acres were sold on which the first St. Louis Heights homes were built. Streets were named for early members of the order who started the school – Bertram, Eugene, Felix and others.
The Pearl Harbor attack directly affected this community as the school was taken over as a hospital and offices for the military. The government quickly threw up even more buildings on the hillside, making it one of the busiest places on Oahu during World War II. President Roosevelt even visited the hospital at one point.
The end of the war brought a close to the military’s presence, but started an acceleration of home building on these streets. Homes on St. Louis Heights were well loved for their stunning views and easy access to both downtown and Waikiki.
Few today would ever guess that this quiet community was once a beehive of activity aimed at winning the war in the Pacific.
This mountain, actually an extinct cinder cone left by the Ko’olau Volcano, was originally called Pu’uohi’a by the Hawaiians. The name change was a result of an 1840’s Punahou school field trip. The schoolboys, looking for ferns, decided to call it Tantalus after the Greek mythology figure. Somehow the name stuck.
The intimidating climb, and lack of roads, left the upper reaches unsettled until the 1880’s when the first home was finally built on the slopes. Others began to follow, though most of these early Tantalus homes were summer housing for the elite families who wanted to escape the heat of lower Oahu.
The initial roads were made up of gravel laid down by Oahu prisoners, who also had the job of maintaining them. For the first few decades of settlement the Tantalus home owners had envious views, but lacked some modern conveniences.
Electricity didn’t arrive on Tantalus until the 1920’s, 30 years after some parts of Honolulu. Rainwater was collected in tanks for daily use. Few homes had telephones so the ones that did let neighbors without them use theirs. The community became close-knit, partly because they needed to be.
That closeness is still there, but you don’t need to ‘rough it’ any more. Today, buying a home on Tantalus means sacrificing nothing except hotter temperatures.
Waialae Golf Course
Waialae Golf Course’s existence, along with the Royal Hawaiian Hotel’s, owes itself to a tourism promotion campaign intended to tempt high-end visitors to Hawaii in the 1920’s. The flat land wasn’t the most desirable for a golf course, so they hired a legendary designer named Seth Raynor to work his magic. Raynor’s courses are eagerly sought out by today’s golfers, ready to pay exorbitant sums to challenge his fairways. Amazingly, the man never played a round of golf until after he had completed 4 of his famous courses.
The land was leased from the Bishop Estate and opened to welcome the first duffers on February 1, 1927. Territorial Hotel Co., who owned Waialae, got into financial troubles during the Great Depression and turned their holdings over to the Matson Company.
Though World War II saw the country club taken over by the military to establish coastal defenses, it was the 1960’s that saw the greatest incursion, at least from golf fans’ point of view. The building of the Kahala Hilton prompted the Bishop Trust to take back the oceanfront fairways and other land from the country club.
All of Raynor’s design was taken out as the golf course was moved inland and completely reconfigured. Online golf forums are still filled with fans weeping from this loss, over 50 years later. Waialae Golf Course homes are still a pleasure despite that, many of which enjoy a place right on the fairway. With the beach just steps away, a house here is guaranteed to erase all unpleasant memories.
Wiliwilinui was once the name for this entire ridge, given because of the wiliwili trees that bloomed here so beautifully. The famous trail at the top still bears that name, while the rest was later renamed Waialae Iki after the Waialae Springs.
The water from these springs was reserved for the chiefs only, watched over by trusted keepers who passed on the duty through generations. By the 1800’s they had been forgotten until Kamehameha III chanced to walk through the area and asked an elderly couple for some water.
He was astonished to learn that they were the current guardians of the springs, keeping alive the line that stretched far into their family history. They were still there specifically to serve the king water if and when the need arose.
The ridge did hold a small collection of residents, but didn’t see much activity until World War II. The fear of invasion prompted the US military to build Battery Willy at the ridge’s high point, using gun turrets from 2 aircraft carriers. They remained here until 1944, when there were no more threats to the Islands. The bunkers are a popular attraction for hikers today.
It took another 20 years for Waialae Iki homes to begin appearing, beginning at the bottom of the hillside. Streets and homes slowly emerged higher and higher on the ridge over the years, the topmost neighborhood, a gated, luxury enclave, finally coming to life in the 1980’s. Homeowners now enjoy not only tremendous views every day, but also free access to the water, royalty or not.
Like most homes in Honolulu built on the high ground, there were few residences on Waialae Nui Ridge until the 1900’s. The pre-automobile inaccessibility kept these heights almost completely uninhabited.
The land at the foot of the hills was used mostly for agriculture during this time. Taro, sweet potatoes, sugar cane and even tobacco were all grown there at one time or another.
The explosion of development in nearby districts during the 1950s filled in much of the lands between the hills and the ocean. The next step was to start building upward. Although some construction began in the mid-1950’s, it was the following decade that saw a huge acceleration in Waialae Nui Ridge real estate lining the rise. Most of this neighborhood was built during this time, predominantly by prolific developer Herbert K. Horita.
Horita took the wise step of having acclaimed architect Vladimir Ossipoff design some of the models. Horita then used these floor plans for many of other houses. This lineage created demand for these Waialae Nui Ridge homes that has only increased as time has passed. Many of the houses are held up as masterpieces of mid-century design.
Since then a few more streets and homes have been added further up the ridge on the eastern side. These larger, later houses may lack pedigree, but make up for it in modern luxury and even greater views from their seat at the very top. The only way to get a better view would be to take a long, hot hike even higher up the mountain. Why do that when you can enjoy it from the comfort of a beautiful home?
Had it been left untouched, Waikiki would today be swampland, just as it was hundreds of years ago. It was clear to Native Hawaiians, however, that this land had great agricultural potential due to its abundant freshwater springs. It’s believed that Oahu’s Chief Kalamakua created an irrigation system in the 15th Century to take advantage of these assets. Soon, taro farming was in place along with newly built fishponds to feed his people.
These farmlands would be overrun 3 centuries later when King Kamehameha’s armies landed here in 1794 on their way to conquering Oahu. His victory resulted in Waikiki becoming one of the new Kingdom’s primary Royal Retreats, not only for Kamehameha, but also his successors on the throne. The beautiful beaches and waters of this district became the preferred hideaway for every ruler up to the last Queen, Liliuokalani.
The increasing importance of tourism in the early 1900’s required firm land for building. For this reason the Ala Wai Canal was dug out in 1928 by Hawaiian Dredging. This drained the remaining swampland, creating the new, solid real estate that was needed.
The years following the Canal’s building saw new buildings spring up to serve the visitor industry. This was slowed down only by the attack on Pearl Harbor. That event altered the neighborhood from a resort to something resembling a military base. Until the end of World War II the famous beaches were strung with barbed wire and the Royal Hawaiian Hotel was converted to soldiers’ barracks.
Up into the early 1950s, there were still private homes on Kalakaua Ave and other beachfront streets. They’d all eventually give way to tourism properties. One exception was the 1st high-rise Waikiki condo, Ilikai Apartment Building, which went up on in 1965.
By the late 1960’s the streets between Kuhio Ave and the Ala Wai had become widely known as ‘The Jungle’. Due to deteriorating structures, crowded conditions and many colorful residents, this area had a reputation as a good place to avoid.
A solution was needed, especially in light of rising land values. This resulted in the demolishing of most of the old wooden homes, replaced by the condos that you see today in Waikiki.
Over 200 years after Kamehameha’s landing, this land is now under siege by those looking to conquer their own slice of this part of Honolulu. We call them Waikiki condo buyers.
Wailupe Beach neighborhood sits on the ocean side of Kalanianaole Hwy. Like a lot of places around Oahu, it was once the site of an ancient Hawaiian fishpond. Yet Wailupe fishpond was unique for 2 reasons. First, it was extremely large, taking up 41 acres in all. The entire present day neighborhood stands on what was once water.
Second is the fact that it survived longer than many other ancient fishponds on this side of Oahu. In fact, it’s conceivable that it might be there even now if not for the 1946 tsunami. The impact of this event left the pond walls severely damaged and the surrounding area devastated. The large dairy farm based nearby was put out of business and the owner, whose holdings included the pond, sold his land to Walter Dillingham in 1947.
Dillingham owned Hawaiian Dredging and saw the possibilities for the area. His company dug out the channel that sits by the peninsula now, moving over the earth dug up to fill in the fishpond. At the time, Wailupe was one of only 3 ancient Hawaiian fishponds remaining on Oahu’s eastern shores.
Wailupe Beach homes were soon added on top of the new grounds, creating a neighborhood right on the ocean. Some vestiges still exist that mark the old pond which once sat across from the current fire station. Everywhere else you’ll find the modern homes of Wailupe Circle, sitting on prime real estate that didn’t even exist less than a hundred years ago.
Wilhelmina Rise is the prime example of a neighborhood that couldn’t exist until the 20th Century. Up until the early decades of the 1900’s transportation was dependent on the horse. There was no way anyone could get their daily business done living up there. The commute just wasn’t possible on that incline.
That changed when automobile use became widespread, allowing people to live on these heights. Surprisingly it was the Matson Company who seized the opportunity to develop this area in the 1920’s, carving out the notorious mile long road that goes up the hillside. The new Wilhelmina Rise homes were placed on a steep slope, but they enjoyed an outlook over the city that was difficult to beat.
Though they didn’t stay long in the building business, Matson did leave a legacy behind. Many of the streets are named for their famous ships, such as Lurline, Mariposa and Monterey. Most importantly, that main road, and the neighborhood, got its name from yet another Matson ship, the Wilhelmina.
Wilhelmina Rise has only gained notoriety since it was first paved, attracting people who drive up the steep road, just for the experience. Extreme athletes are even known to challenge themselves, and each other, to walk or even run up the entire mile. Little did Matson know, they were building not only a neighborhood, but a fitness course.