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10 Amazing Streets In Diamond Head & Kahala

10 Amazing Streets in Diamond Head and Kahala
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One of our well-to-do Beverly Hills client is accustomed to a certain way a neighborhood should look. Occasionally he would go sightseeing in Honolulu and report when he discovered what he referred to as a more normal looking street. Inspired by his keen observations we compiled the following list of fine Diamond Head and Kahala streets. This list is subjective and each street made the list for a variety of different reasons. We hope you enjoy.


Noela Drive Arial Map

1.) Noela Drive & Noela Place – Royalty used to live here. Just below the western slope of Diamond Head some impressive Diamond Head grand estates are hidden behind security gates. Both Noela Dr and the short Noela Pl are unassuming gently sloped cul-de-sacs. Noela Dr does not even have a sidewalk. This is a remarkably quiet location considering the proximity to popular Kapiolani Park.

Many of the homes are sitting on half acre and larger lots. The upslope lots offer pleasant views of Kapiolani Park and ocean beyond.

Noela Drive Aerial Photo
Some notable Noela Dr and Noela St homes include:

3239 Noela Dr, formerly owned by developer Jack Meyers. Situated on more than an acre with a huge half moon shape pool and a 10,000+ sq ft mansion. The property sold for $8.75 Mill in 2009 during a soft real estate market.

3944 Noela Pl, formerly owned by Barbara Cox Anthony who was at one time the richest woman in Hawaii. This large Mediterranean inspired villa with pool and tennis court on a ~1.2 acre lot sold in 2008 at $7.8 Mill to my good friend and former boss Herb Conley.

3175 Noela Dr is currently (Nov 2016) listed for sale at $11.495 Mill. This is a gorgeous newer 2006 built 9,800 sqft home developed by Tom Nicholson situated on a ~29,000 sq ft lot.

2.) Diamond Head Circle Р North of Noela Dr and accessible only from Monsarrat Ave is Diamond Head Circle, a quiet street loop with several grand estates. Tucked away from traffic, Diamond Head Circle offers modest elevations and city views. Many lots are half an acre and larger.

Diamond Head Circle - Aerial Map

Some notable Diamond Head Cir homes include:

3692 Diamond Head Circle, a large 2 acre estate located in the interior section of the loop, originally built in 1938 with large pool and Hawaii’s longest private water slide designed by Olympic gold medalist and Tarzan legend Johnny Weissmuller. Hollywood celebrity Lana Turner and others used to frequent the estate. The property was listed for sale at $13.5 Mill in poor condition as recent as 2015.

3735 Diamond Head Circle is a gorgeously restored Hawaiian estate home at the highest elevation point on Diamond Head Cir. The 1.267 acre estate sold at $6.9 Mill in August 2016.

3.) Makalei Place

Makalei Place - Aerial Map

Often overlooked, with less than 20 custom homes on Makalei Pl this short winding cul-de-sac is easy to miss off Diamond Head Rd. Hardly anyone ascends this steep south western slope of Diamond Head Crater¬†with its¬†desirable privacy.¬†Here we find some of Diamond Head’s highest elevation residential homes. Seemingly located directly below the Diamond Head Crater summit, Makalei Pl homes enjoy impressive ocean views.

Makalei Luxury Estate - Aerial View

One notable Makalei Pl property is 2955 Makalei Pl with an impressive infinity pool and separate guest house sitting on half an acre of land, sold at $7.55 Mill in 2007.

4.) Pokapahu Place ‚Äď Pokapahu Pl is a short clean looking quiet cul-de-sac along the most eastern slope of Diamond Head Crater. Only about a dozen homes are situated here and every home enjoys good elevation with gorgeous sunrise views overlooking green Kahala coconut trees, the ocean and distant Koko Head and Koko Crater.

One notable Pokapahu Place home is 3868 Pokapahu Pl, designed by architect Jim Mc Peak and completed in 2012 with a stunning infinity edge pool. The property sold soon after completion at $6.3 Mill in November 2012.

5.) Kaikuono Place ‚Äď This is where Doris Duke made her home with her Shangri La oceanfront estate. Only half a dozen homes are found on this short cul-de-sac offering privacy and ocean views. The street is narrow with minimal street parking. Only the two homes at the end of the cul-de-sac are on the ocean on top of a rocky cliff. However, for all other Kaikuono Place residents, a narrow gated footpath serves as ocean access to a small secluded sandy beach below.

One notable Kaikuono Place home is 202 Kaikuono Place. Featured in Architectural Digest Magazine, the home was stunningly remodeled and offers dramatic ocean and sunset views. Simply magical. The property sold at $14.2 Mill in December 2015.

Kaikuono Place and Kaikoo Place - Aerial Map

6.) Kaikoo Place ‚Äď Just east of Shangri La, Kaikoo Place is a cul-de-sac off Papu Cir, steeply descending towards the ocean. The street looks nice with sidewalks on both sides and interesting architectural home styles.

There are 8 Kaikoo Pl homes directly on the ocean. What makes the street special is, due to the unique topography, every Kaikoo Pl home has fabulous ocean views.

The ocean’s wave action can be dramatic and the shoreline here is rocky offering privacy in this coveted ocean front location. A public ocean access is at the bottom of the street mainly used by occasional surfers paddling out to the outer surf break.

Instead of a regular turn-around area at the end of the cul-de-sac, Kaikoo Pl splits up into a one-way street looping around a single large home with no neighbors.

Some notable Kaikoo Place homes include:

4324 Kaikoo Pl, formerly owned by visionary hotel developer Chris Hemmeter and is considered one of the largest single family home on Oahu. This impressive ocean front villa boasts over 21,000 interior sq ft, plus large decks for a total of 29,000 sq ft of living space sitting on a 0.823 acre oceanfront lot with a whopping 300 ft wide ocean frontage.

The property sold for $12.902 Mill in 1994 during a soft real estate market.

4310 Kaikoo Pl, another more modest ocean front property with 5,000+ sq ft interior living space on a 9,910 sq ft lot sold for $8.6 Mill in 2004.


7.) Royal Place & Royal Circle ‚Äď Oceanside of Kahala Ave without Kahala Ave‚Äôs busy traffic. Royal Place branches off Kahala Ave with 5 Royal Place homes situated directly on the ocean. Royal Circle is a short cul-de-sac going up the knoll offering excellent ocean views.

Half a dozen Royal Circle homes along a shared driveway enjoy the added security of a privacy gate.

Royal Circle & Royal Place - Aerial Map

Some notable Royal Place and Royal Circle homes include:

4377 Royal Place, developed by developer Don Eovino in 2006 represents one of the very few newer Kahala oceanfront homes. This gorgeous island style home includes 6,500 sq ft interior living space with additional decks and pool cabana for a total of 8,700+ sq ft living space sitting on half an acre on the ocean. Both, the home and the oceanfront setting are gorgeous. The property sold at $11.1Mill shortly after it was listed in 2006.

4375 Royal Place, immediately next door, built in 2001, sold for $19.8 Mill in late 2015.

100 Royal Circle, a remarkable property situated at the end of the private shared driveway behind the Royal Cir gate. Built in 1990 with 8,626 sq ft interior living area situated on an oceanfront acre with an impressive 200+ ft of linear ocean frontage. The property sold for $16.5 Mill in 2013.

114 Royal Circle, at one time owned by surf legend Duke Kahanamoku is located at the top of the non-gated section of Royal Circle. This special home was lovingly remodeled to perfection with infinity edge pool and awesome indoor outdoor space. Offering spectacular ocean views, the property sold for $8.35 Mill in August 2016.

Royal Circle Aerial Photo

8.) Kahala Ave Р Arguably Honolulu’s most famous street with large grand estate oceanfront lots, like no other real estate in Honolulu. There are only about 40 Kahala oceanfront homes and most of these are along Kahala Ave. Many of these estate lots are half an acre and some as large as 2 acres.

What makes Kahala Ave special is not just the size of these large oceanfront estate lots. It is the adjacent pristine south facing white sandy beach, plus Kahala’s deed restrictions ensuring a desirable low density with generous setbacks and a park like neighborhood feel.

Kahala Ave Beachfront Homes - Aerial Photo

Tour buses occasionally pass through Kahala Ave on their scenic circle island tours for visitors to see what Kahala is all about.

Between sprawling Kahala Ave estate homes, several lots remain vacant. Older homes had been torn down including some of Kawamoto’s 27 neglected Kahala Ave homes which sold to local developer A&B.

A&B’s bulk purchase, subsequent clean-up and sale of these properties is renewing Kahala Ave’s undisputed image as the most prestigious street for Honolulu homes.

Some notable Kahala Ave homes include:

4653B Kahala Ave, an address former president Mr & Mrs George W.H. Bush and Jackie Kennedy Onassis visited. This 1.5 acre private oceanfront estate with pool and tennis court sold for $22 Mill in 2010.

4663 Kahala Ave, the famous blue roof mansion situated on a 1.284 acre oceanfront lot formerly owned by Kawamoto has been known for its large marble statues that used to be displayed in the front yard. Kawamoto had paid $18 Mill in 2010. A&B paid $15 Mill in 2013, and the property was recently listed for sale at $22 Mill in August 2016, without the marble statues.

9.) Aukai Ave ‚Äď Aukai Ave runs parallel to grand Kahala Ave, just a short block further away from the beach. Aukai Ave‚Äôs narrow appearance including old wooden utility poles does not compare favorably to grand Kahala Ave. Yet Aukai Ave properties historically have been selling for higher $ / sq ft prices compared to non-oceanfront Kahala Ave properties.

This seems to contradict the golden real estate rule ‚Äúlocation, location, location‚ÄĚ which normally translates into higher property values the closer the proximity to the beach.

The secret to Aukai Ave’s special allure and value is its coveted feel and privacy without Kahala Ave’s traffic. Living on quiet Aukai Ave you are always within a short block to Kahala Beach. Public beach access is at Kala Pl, Hunakai St, Koloa St, Pueo St and a few more in between.

Kahala Ave, Aukai Ave and Kolohala Ave - Aerial Map

Some notable Aukai Ave homes include:

4707 Aukai Ave, developed with Don Eovino’s signature island style design, this 0.4 acre property sold for $6.505 Mill in August 2016.

4510 Aukai Ave, nicely remodeled in 2014, situated on a 0.25 acre lot sold for $5.4 Mill in Summer 2014.

10.) Kolohala St ‚Äď One block further away from the ocean, Kolohala Ave runs parallel to Aukai Ave. Especially the section between Elepaio St and Hunakai St has a sense of grandness. Remarkably few cars park in the street.

Kolohala Ave looks super wide with underground utility lines and has little through traffic. Pristine Kahala Beach is only two short blocks from here.

Some notable Kolohala St homes include:

4449 Kolohala St, developed in 2007 by Tim Gutierrez, with Pyramid Premier Properties, one of Hawaii’s respected custom home builder. Signature home features include huge disappearing pocket doors creating an indoor Рoutdoor space flowing seamlessly together on a 0.254 acre lot. The property sold for $3 Mill in 2009.

4743 Kolohala St, built in 2000, currently listed for sale at $3.198 Mill and as of Nov 14, 2016 scheduled to record soon.

Let us know what you think. Perhaps you have a favorite street in Diamond Head or Kahala that should be added to the list. We like to hear from you.

Please ‘Like’, ‘Share’ and ‘Comment’ below.


10 Amazing Streets In Diamond Head & Kahala was last modified: February 5th, 2018 by George Krischke
George Krischke
Principal Broker (R) Hawaii Living See my other articles
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