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Oahu Real Estate | Most Expensive Luxury Neighborhoods on Oahu - Top 15

The Top 15 most expensive neighborhoods on Oahu, Hawaii for 2017 single-family homes are island-wide, spanning Honolulu, Kailua, and the North Shore. Luxury homes on Oahu can be found mostly around the perimeter of Oahu, where there are beaches. Luxury homes on Oahu can also be found where there are great ocean views or mountain views. There are many luxury homes on Oahu and many expensive neighborhoods on Oahu, because beaches and views are not in short supply here! Some of Hawaii’s best homes are on Oahu, though stunning Hawaii luxury real estate can be found on all of the Hawaiian islands.

Oahu luxury real estate in lanikai

Topping the list for the most expensive neighborhoods on Oahu for 2017 are the following Oahu luxury home neighborhoods:


Honolulu is the largest and most populous city on Oahu, with over 750,000 residents. It is a cosmopolitan city, with both high-rise condominiums and single-family residential neighborhoods. In Honolulu, there are many schools, hospitals, universities, cultural activities, museums, theatres, shopping, restaurants, beaches, marinas, parks, recreational opportunites, and most anything else you might desire to live in Hawaii. You will have a multitude of choices for your Oahu real estate purchase, depending upon your needs and lifestyle.

Diamond Head, Honolulu (22 sold 2017)

Average sale price 2017 - $3,055,914 / Median $2,375,000 

Diamond Head luxury homes on Oahu can be beachfront or oceanfront, or they can have ocean or Diamond Head views. Home prices range to $20M+ for a few select properties. Some Diamond Head homes are historic, as Diamond Head is one of Honolulu’s oldest and most prestigous neighborhoods, favored by many Honolulu’s kama’aina families. Live in Diamond Head and you will get a better feel for “Old Hawaii.”

The Diamond Head neighborhood is home to many of the most stunning parcels of Oahu luxury real estate, with both fantastic mansions and estates, and charming beach cottages. Diamond Head also has many beautiful luxury condominiums on what is called the Gold Coast. This area is also home to recreational facilities, such as Kapiolani Park and the Waikiki Shell, the Outrigger Canoe Club and the Honolulu Elks Club, and upscale restaurant Michel’s, as well as the Hau Tree Lanai at the New Otani Kaimana Beach Hotel. Diamond Head is just south-east of Waikiki and south of Kapiolani park and the Diamond Head crater, before Kahala. 

Here are the Top 4 most expensive homes for sale (or in escrow) in Diamond Head now.

For all luxury homes for sale in Diamond Head click here.

Black Point, Honolulu  (0 sold 2017, 3 sold 2016) 

Average sale price for 2016 - $2,961,667  / Median $2,175,000 

Black Point is a small, somewhat older and elegant neighborhood of around 75 homes with stunning ocean views. The Oahu real estate here is in an oceanside area, tucked atop and behind an outcropping of black lava rock. Some of Oahu’s finest homes, ranging up to around $10M+ in price, these luxury homes do not come on the market often. Some of these luxury homes on Oahu’s Black Point are ocean front, or they can have ocean or Diamond Head views. There are two gated neighborhoods within Black Point: one on Royal Circle and one at the top of Black Point Rd. Black Point was once home to wealthly heiress, Doris Duke and is the location of her famed estate Shangri-La, now a Museum of Islamic Art. Black Point is an exclusive luxury neighborhood nestled between Diamond Head and Kahala neighborhoods, with many gorgeous Oahu homes. 

Here are the Top 4 most expensive homes for sale (or in escrow) in Black Point now.

For all luxury homes for sale in Black Point click here.

Paiko Lagoon, Honolulu (4 sold 2017)  

Average sale price 2017 $2,926,250 / Median $3,327,500 

Paiko Lagoon luxury homes are situated in a unique and lovely area. This magical and scenic spot is home to the protected Paiko Lagoon wildlife sanctuary, and connected to the Kanewai Fishpond. Homes may have frontage on either or both the lagoon and the ocean. Paiko Lagoon was once home to famed Honolulu architect Vladimir Ossipoff. Paiko Lagoon is between Kahala and Hawaii Kai on the Makai side of the Kalanianaole Hwy.

Here are the top 4 most expensive homes for sale (or in escrow) in Paiko Lagoon now.

For all luxury homes for sale in Paiko Lagoon click here.

Niu Beach, Honolulu (1 sold 2017, 3 sold 2016)

Average sale price 2016-2017 - $2,860,000 / Median $2,580,000 

Niu Beach luxury homes can be ocean or beach front, in an oceanside area of Honolulu protected by an outer reef. Niu Beach has less than 100 parcels and properties may be oceanfront and may also offer a deep draft for boat access from your backyard. Niu Beach is an unique and beautiful community, just West of Paiko Lagoon, between Kahala and Hawaii Kai on the Makai side of the Kalanianaole Hwy.

Here are the Top 4 most expensive homes for sale (or in escrow) in Niu Beach now.

For all luxury homes for sale in Niu Beach click here.

Hawaii Loa Ridge, Honolulu (24 sold 2017)

Average sale price 2017 - $2,887,312 / Median $2,430,000 

Hawaii Loa Ridge luxury homes have stunning ocean views, as they are on a hillside across from the ocean at Puuikena Street. Some of the best views on Oahu are found in this exclusive, private, gated neighborhood. Hawaii Loa Ridge homes can range in price to a hefty $20M+, but start at just under $2M. The homes are newer, most built between 1980-2010, and can be elegant and traditional, or even ostentatious.

There is a community recreation center, with tennis courts, for Hawaii Loa Ridge Association, as well as a park and hiking trails on top of the Ridge. There is another even more exclusive gated neighborhood within Hawaii Loa Ridge called The Pointe. Hawaii Loa Ridge is a favorite for part-time Oahu residents, due to the high level of security that the association provides. Hawaii Loa Ridge is on a ridge past Paiko Lagoon and Niu Beach, between Kahala and Hawaii Kai, but closer to Hawaii Kai.

Here are the Top 4 most expensive homes for sale (or in escrow) in Hawaii Loa Ridge now.

For all luxury homes for sale in Hawaii Loa Ridge click here.

Kahala, Honolulu (52 sold 2017)

Average sale price 2017 - $2,707,339 / Median $2,435,000 

Kahala is one of the premier luxury home neighborhoods on Oahu, with a wide variety of gorgeous homes, favored by some of the most weathly Oahu residents. Homes beachfront can range to over $20M. Some Kahala homes are beachfront mansions and some are simple ranch homes built in the 50s and 60s. There are many variations in between inlcuding many remodels and new builds. Many Kahala homes have neither a view or ocean/beach frontage; however, these homes are a very short and accessible distance to beautiful, sandy Kahala Beach, since Kahala has a flat terrain, with sidewalks.

Kahala also has protective covenants and zoning that prevents the neighborhood from becoming too dense. Kahala is home to the Waialae Country Club for golf and recreation, as well as the Kahala Hotel and Kahala Shopping Mall. Well-located for ease of getting around Honolulu, but not overly congested, Kahala is a favorite area of many of Honolulu’s well-heeled residents. Kahala perhaps is one of the most liveable areas of Honolulu, with the duo of both the natural beauty of a beach neighborhood and lifestyle convenience. Kahala is in the Diamond Head region of Honolulu.

Here are the Top 4 most expensive luxury homes for sale (or in escrow) in Kahala now.

For all luxury homes for sale in Kahala click here.

Portlock, Honolulu (5 sold 2017)

Average sale price 2017 - $2,690,000 / Median $2,650,000 

Portlock is a luxury real estate neighborhood that is in the Hawaii Kai region of Honolulu. Portlock was once the home to Henry J. Kaiser who built most of that area. About 1/3 of Portlock luxury homes are fronting the ocean and beach at Maunlua Bay. Others are set back a street or two, but they can still have stunning ocean, Diamond Head and city light views. Most lots are larger and the area is quiet and further East, away from downtown Honolulu, situated on Maunalua Bay. There are a multitude of recreational activities, shopping restuarants, etc. within less than a few miles, in the center of Hawaii Kai, but no businesses actually in this neighborhood. 

Here are the Top 4 most expensive homes for sale (or in escrow) in Portlock now.

For all luxury homes for sale in Portlock click here.

Wai’alae Golf Course, Honolulu (4 sold 2017)

Average sale price $2,565,031 / Median $2,510,000 

In the Wai’alae Golf Course neighborhood, many homes front the Waialae Golf Course and have golf course views. Others do not, and typically, these homes are not known for their ocean views, as they are on a flat area near Kahala. Many of these Oahu luxury homes are one-story ranch style, but those that are two-story many have golf course views. This neighborhood is a quiet residential neighborhood similar to and near Kahala, but further from Kahala Beach and closer to the Kalanianaole Highway. Wai’alae Golf Course is a neighborhood of luxury homes on Oahu in the Diamond Head region of Honolulu, at the base of the Waialae Iki neighborhood of view homes.

Here are the Top 4 most expensive homes for sale (or in escrow) in Waialae Golf Course now.

For all luxury homes for sale in Waialae Golf Course area click here.

Koko Kai, Honolulu (5 sold 2017) 

Average sale price $2,482,800 / Median $2,660,000 

Koko Kai is a small Oahu luxury real estate neighborhood of about 130 or so homes, that is in the Hawaii Kai region of Honolulu. Koko Kai is near Portlock but is more remote and private. Koko Kai is known for its clifftop homes with amazing ocean, sunset and city views. Koko Kai luxury homes are within a few miles of shopping and dining, and lots of water sporting activities in Maunalua Bay

Here are the Top 4 most expensive homes for sale (or in escrow) in Koko Kai now.

For all luxury homes for sale in Koko Kai click here.

Waialae Iki, Honolulu (39 sold in 2017)

Average sale price 2017 $1,749,741 / Median $1,662,500 

Waialae Iki is an Oahu luxury home neighborhood in the Diamond Head region of Honolulu, just above the Waialae Golf Course.

Here are the Top 4 most expensive homes for sale (or in escrow) in Waialae Iki now.

For all luxury homes for sale in Waialae Iki click here.


Kailua is a gorgeous no so little beach town in Windward Oahu about 15 miles from downtown Honolulu. As you make the scenic drive to Kailua over the Pali Highway, you automatically feel a sense of peace and ease, away from the hustle and bustle of Honolulu. Kailua has about 40,000 residents and all you could need in terms of shopping, restaurants, schools, hospitals, and of course, gorgeous beaches, parks, hikes, and numerous other recreational opportunites. Yet, from Kailua, it’s just a quick trip to “Town” (as Kailuans call Honolulu).

Lanikai, Kailua (24 sold 2017)

Average sale price 2017 -$3,117,069 /Median  $2,297,826 

Lanikai is a beach community in Kailua, just South of Kailua Beach Park, which is been regarded as having one of the best beaches in the world for decades. This is not suprising, as Lanikai means Heavenly Sea in Hawaiian. Pristine white sand with turquoise waters frame the iconic Mokulua islands, in the distance, perfectly. Beachfront and ocean front homes comprise about 20% of the approximately 500 homes in this neighborhood. There are also homes in “the flats,” a flat section of Lanikai, which is less a block or less from Lanikai Beach and its many beach/ocean access points. The flat terrain neighborhood is complemented by another section of homes on the Lanikai hillside which often have fabulous views. There are a few historic homes (1920-30’s) remaining in Lanikai, as it is one of Kailua’s oldest areas. Homes in Lanikai can range past $20M, but ocean/beachfront starts around $5M. Other properties range from over $1M for a teardown to about $3M+. Styles of homes range from historic beach cottages, to Balinese estates, to Tuscan-style mansions (and everything in between).

Despite the hefty price tags, there is a softer and more relaxed vibe in Kailua, as compared to Honolulu. This is a true beach community, without most of the trappings of the City. Can you already feel the soft sand between our toes? Can you smell the sea in the warm breeze? People, including Hawaiian royalty, have historically gone to Lanikai to relax. There is one road in and out of this exclusive luxury home neighborhood, with no sidewalks, affording relative privacy. Lanikai has a voluntary Community Association and Park, and lots of neighborhood activities. Kaohao Public Charter Elementary School, located nearby, serves Lanikai families. Watersports, such a outrigger canoeing, swimming, SUP, and any other water sports are big here. As is the Pillbox Hike, where you can view the homes below and surrounding ocean for miles. The Mid-Pacific Country Club, with golf course, pool, gym, and restaurant is the only business in the neighborhood. Shopping requires a 1-2 mile drive into Kailua Town. Lanikai is famous for having several celebrities who have lived and stayed there, such as Do Ho, Elvis Presley, Michelle Pfiefier, and more.

Here are the Top 4 most expensive homes for sale (or in escrow) in Lanikai now.

For all luxury homes for sale in Lanikai, Kailua click here.

Beachside, Kailua  (18 sold 2017)  

Average sale price 2017 - $2,455,222 / Median $2,094,000 

Continuing in Kailua, Oahu is the Beachside neighborhood. It has the same relaxed beach feel as Lanikai, but this neighborhood is less contained than Lanikai, as it spans almost the entire Windward side of Kailua, just makai of Kalaheo Ave, starting just North of Kailua Beach Park. As in Lanikai, Beachside luxury real estate in Kailua can range from small cottages on tiny lots to huge estates. The style of construction, again varies.

Beachside has arguably become more popular than Lanikai, lately, among some residents, since it is more convenient to Kailua Town, not having the constricted one-road-in/one-road-out issue that Lanikai can have. Also, while the beaches in Beachside are extraordinaily beautiful, they are often not as crowded by tourists as in Lanikai. However, as a Kailua resident myself, It seems that Beachside does not have the same sense of community that Lanikai has. There is a tradeoff there in a few aspects of the two communities and there will be differences of opinion on which neighborhood will suit you the best. 

Beachside is comprised of several smaller beach lanes, some of which are private, and various loop streets, as well as the most upscale Kailuana subdivision, which has sidewalks and underground utilities. Some of the Kailuana homes may also front the Kawainui Canal which leads to the ocean. This area is frequented by former President Obama for vacations. 

Beachside homes are either on or less than a block from the 3 mile long sandy white stretch of Kailua Beach and the turquoise waters Kailua Bay, with activites including windsurfing, kitesurfing, surfing, SUP, kayaking, swimming and fishing. Kailua Bay is fairly calm and protected by an outer reef. Sunrises and beachwalks from the Beachside neighborhood are absolutely fantastic! 

Here are the Top 4 most expensive homes for sale (or in escrow) in Beachside now.

For all luxury homes for sale in Beachside, Kailua click here.


The North Shore of Oahu is the spot to be if you are an accomplished surfer, or if you want to relax with a more more country feel. There is not much in the way of commerce on Oahu’s North Shore, but the few small towns, Haleiwa and Waialua, with their small shopping and restaurant districts, have a unique charm of their own. This is where you can get away and refresh your body, mind, and spirit, along with beautiful scenery, good people, and plenty of watersports.

Kawailoa, North Shore (4 sold 2017)

Average sale price $3,437,500 / Median $2,475,000 

Kawailoa is regarded by some as the premiere location for luxury real estate on the North Shore of Oahu. This small and exclusive area is located just between Waimea Bay and Haleiwa Town, making it convenient for both water activities, big wave watching or surfing, as well as for shopping and dining. At the lower end, prices in this neighborhood start just under $1M, but the beautiful beachfront home on Papailoa Rd can range up to $8M. While carrying a hefty price tag, great properties don’t come up here as often or often sit as long, as some other areas, so make sure to snap one up if you can.

Here are the Top 4 most expensive homes for sale (or in escrow) in Kawaialoa now.

For all luxury homes for sale in Kawailoa click here.

Mokuleia, North Shore (9 sold 2017)

Average sale price 2017 $2,296,444 / Median $2,200,000 

Mokuleia is a small quiet beach community in Waialua, at the Western end of the North Shore stretch of beaches. Mokuleia Beach Park is here in this area, as well as the Hawaii Polo Club. Look for luxury real estate in Mokuleia if you want to get a bit further away from the main surf action and have a more peaceful setting. The most expensive homes here are generally large and upscale, in a beachy, plantation-style way, with gorgeous views of the beach and ocean. However, there are also smaller homes, as well as homes are in a more agricultural setting, which may provide acreage. Prices will vary from just under $1M up to about $5M. Mokuleia is about as close to heaven as you can get on Oahu!

Here are the Top 4 most expensive homes for sale (or in escrow) in Mokuleia now.

For all luxury homes for sale in Mokuleia click here.

Sunset, North Shore (12 sold 2017)

Average sale price 2017 $1,874,167 / Median $1,500,000 

The most expensive Oahu, Sunset Area homes are in Haleiwa on the North Shore, close to both Haleiwa Town and Waimea Bay. These homes are often beachfront or ocean view and near or in front of some of the best surf spots on Oahu - perfect for big wave watching or relaxing, enjoying the sunset. Homes range in style from modern to beachy plantation or even Bali-style homes. Prices here start under $1M for a shack away from the beach, but top around $5M, some on expansive lots! While a fantastic location, best to watch out for homes with beach erosion problems here, as this has been a worsening issue over the years.

Here are the Top 4 most expensive homes for sale (or in escrow) in Sunset now.

For all luxury homes for sale in Sunset click here.

If you would like more information or assistance with finding a home in a luxury neighborhood on Oahu, please don’t hestate to call Yvonne Jaramillo Ahearn, Esq. at 808-721-8088

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