Search All Diamond Head Real Estate

The Diamond Head neighborhood is comprised of 650 or so homes that represent some of the finest and most sought after Real Estate in Honolulu.

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Newest Listings

$3,800,000

3 Beds ⋅ 4 Baths ⋅ 202320678 MLS ⋅ FS - Fee Simple Tenure ⋅ 2 DOM

Experience the beauty of island style living at this exquisite residence on highly coveted Aukai Avenue featuring 3 bedrooms plus den, 3 baths & 1 half bath sitting on a 11,250 sq ft lot. Feel the perfect blend of indoor/outdoor living as floor plan surrounds lush landscaped yard with saline pool & hot tub and large covered patio with outdoor seating/bar, perfect for entertaining! 2nd floor guest suite with deck overlooks expansive yard, gourmet kitchen includes stainless steel appliances/built-in kitchen nook sitting area, owned Photovoltaic system features 44 panels and gated driveway leads to 2-car carport in the back. End your day with a swim in the tranquil pool or spend time relaxing in the hot tub. Ideally located just 1 block from Kahala Beach access and short distance to the Kahala Hotel & Resort, Waialae Country Club/Golf Course, Kapiolani park & Kahala Mall. *Actual number of bathrooms and square footage does not match TMK records*

4579 Aukai Avenue, Honolulu

$1,175,000

5 Beds ⋅ 2 Baths ⋅ 202321214 MLS ⋅ FS - Fee Simple Tenure ⋅ 3 DOM

First time on the market. Enjoy the privacy and peacefulness of Kipona Place, tucked away on a quiet street in Palolo Valley. This 5 bedroom, 2 bath home can also be used as two living areas as a 3/1 and 2/1 which is great for extended families. Short drive to all the restaurants and shops that Kaimuki and Kahala Mall have to offer along with Chaminade and University of Hawaii nearby.

2310 Kipona Place, Honolulu

$4,950,000

5 Beds ⋅ 4 Baths ⋅ 202320653 MLS ⋅ FS - Fee Simple Tenure ⋅ 5 DOM

Located just one lot away from the blue Pacific Ocean, offering panoramic sunsets views as well as endless ocean activities this home allows one to enjoy all the benefits of effortless beachfront living. A deeded interest in a Private Beach Lane leads to the sandy beach “Cove Area” of Diamond Head. Kaalawai Place is off Diamond Head Road so less noise and traffic and a short walk across Diamond Head Road is Triangle Park, a great place for children to run and play in when they are not exploring the tide pools at the end of the beach area. Upstairs expansive primary suite boasts a generous sized office making “working from home” a breeze. Three additional bedrooms and a room for workouts or an additional office is adjacent to the formal living room, open kitchen/dining/living room, and outdoor lanai area with grill and dining area if needed. Front grassy lawn is perfect for that “four legged” family member or a pool.

223 Kaalawai Place, Honolulu

$585,000

2 Beds ⋅ 1 Baths ⋅ 202321788 MLS ⋅ FS - Fee Simple Tenure ⋅ 4 DOM ⋅ Diamond Head Hale Corp BLDG.

Nestled in the highly sought-after Pualei Circle, you'll find yourself just moments away from Kapiolani Park, Kaimanas beach, renowned surf spots, shopping, and dining. The relaxed lifestyle you've been looking for is within reach. Imagine waking up & heading out for a morning swim, surf or paddleboard. This home offers abundant natural light w/ windows on three sides & a perfect place for a dining room table or study. Enjoy the view of Diamond Head from your living & dining room. The property has lovely in-ground pool, perfect for leisurely afternoons on the loungers or lunch w/ friends around the outdoor table. You'll appreciate the tranquility & serenity the community offers & the well manicured grounds. This unit does not have a deeded parking space, but there is an option available. Home is ready for immediate occupancy, freshly painted & awaiting your personal touch. It's worth noting that the flooring in this condo requires replacement, providing you with the perfect opportunity to personalize and elevate this space. Some interior photos have been virtually staged to help you envision the incredible potential of this Pualei Circle home. Easy to see! Schedule a showing today!

3131 Pualei Circle Unit 13, Honolulu

$1,185,000

3 Beds ⋅ 2 Baths ⋅ 202321729 MLS ⋅ FS - Fee Simple Tenure ⋅ 6 DOM

SOLD WITH TMK: 1-3-3-015-044-0001 RARE grandfathered in vertical cpr consisting of 2 single family homes on lower Wilhelmina. Each with it’s own TMK, electric/gas meters, laundry facilities, trashcans, and mailboxes. Both homes have 3 bedrooms and 2 fulls baths. There is NO internal staircase and 2 entrance/exits to each home. Ocean and Diamond Head views from both homes. Large carport with long driveway. Storage large enough to fit a car or perfect for a workshop. PV-22 panels on upper home. 1 family owner and the pride in ownership shows. must see!

1379 13th Avenue Unit B, Honolulu

$1,185,000

3 Beds ⋅ 2 Baths ⋅ 202321722 MLS ⋅ FS - Fee Simple Tenure ⋅ 6 DOM

SOLD TOGETHER WITH TMK 1-3-3-015-044-0002 RARE grandfathered in vertical CPR consisting of 2 Single Family Homes (one atop the other) on lower Wilhelmina. Each with it’s own address, electric/gas meters, laundry facilities, and trashcans. Both homes have 3 bedrooms with 2 fulls baths. There is NO internal staircase and 2 entrances/exits for each home. Ocean and Diamond Head views from both homes. Carport with a long driveway. Storage large enough to fit a car or perfect for a workshop. 22-PV panels on the upper home. 1 family owner and the pride in ownership shows, must see!

1379A 13th Avenue, Honolulu

$14,200,000

5 Beds ⋅ 9 Baths ⋅ 202321533 MLS ⋅ FS - Fee Simple Tenure ⋅ 6 DOM

Introducing 4615 Kahala Avenue! Hidden from all with a grand gated entrance, you enter these solid and secure grounds finding yourself surrounded by thoughtful landscape architecture that leads you to the Main Home. One of the most picturesque oceanfront locations on Oahu, solidly positioned right in the heart of Kahala, this beautiful single-story oceanfront home rests on an impressive 40,380 sq. ft. lot. The centerpiece of this private paradise is a palatial home boasting 5 bedrooms & 8.5 bathrooms under 9,422 sq. ft. of luxurious covered living space. Upon entering the grounds on the mountain side of the property, a 3 car garage, together with spacious guest quarters offers a nice introduction to this sensibly designed property. The entire estate, from the entrance to the property, to the home and then flowing all the way to the sea, was built in consideration that thoughtful design, function and privacy are timeless attributes to good living. The crystal blue Pacific Ocean, cool tradewinds, lush palms, lavish greens & water features cocoon the property in serenity. Classic design, privacy, tranquility and premium oceanfront living awaits the buyer who appreciates the best.

4615 Kahala Avenue, Honolulu

$1,685,000

3 Beds ⋅ 4 Baths ⋅ 202321506 MLS ⋅ FS - Fee Simple Tenure ⋅ 9 DOM

Overlooking a peaceful stream with serene tropical surroundings, enjoy the allure of a quintessential Hawaiian country residence with the modern conveniences of a new home. Spacious 3000+ sqft flowing floor plan features soaring vaulted ceilings and expansive windows showcasing lush landscaping and flooding the home with natural light. The upstairs gourmet kitchen features premium stainless appliances, including Bosch gas range and Wolf convection steam oven. Wet bar was added on lower level to allow for an easy conversion to flexible multi-generational living. Benefit from the owned 22-panel PV system that features the old 'Net metering.' Nestled in the coveted 7-acre cluster community, Waiomao Stream, this home borders pristine preservation land ensuring tranquil privacy and no development behind you. Restore and relax in this meticulously maintained property while being close to the vibrant neighborhood of Kaimuki, filled with wonderful eateries and shops, plus easy access to H-1. Don't miss the chance to make this remarkable find your dream home.

2558 Makaulii Place, Honolulu

$1,300,000

3 Beds ⋅ 2 Baths ⋅ 202319687 MLS ⋅ FS - Fee Simple Tenure ⋅ 8 DOM

The “DIAMOND HEAD DARLING” is more than a property; It’s a piece of Hawaiian History that offers a unique blend of Craftsman style charm and an enviable location. With its proximity to Diamond Head, the beach, Waikiki, and University of Hawaii; it presents an opportunity to embrace the BEST of island living. The charm of this two bedroom/one bath main house is evident from the moment you enter with almost nine-foot ceilings, corner niche, beautiful crown, base and wall moldings and embellishments. The detached, separate, and cute one bedroom one bath, wet-bar cottage affords a super separate living area. Entertain your guests in delight under the beautiful, shady mango tree. Here’s your amazing opportunity to own a piece of Hawaii’s past and shape its future. This timeless gem is a rare find, waiting for the right owner to unlock its full potential and create new memories for generations to come.

753 6th Avenue, Honolulu

$14,975,000

202316128 MLS ⋅ FS - Fee Simple Tenure ⋅ 10 DOM

FABULOUS DIAMOND HEAD BEACHFRONT ESTATE PARCEL… Extremely rare opportunity to purchase the last remaining estate sized parcel in this highly coveted section of world renown Diamond Head, home to some of the most exclusive luxury real estate throughout all of Hawaii and the world. Experience gracious rolling lawns, swaying palms and legendary seascapes overlooking 105 linear feet of prime beachfront property and the azure waters of this magical shoreline. This exceptional parcel totaling nearly 32,000 square feet of land is zoned R-7.5 and presents a pristine blank canvas to design an extraordinary luxury residence. Envision waking each day to every imaginable watersport and some of Hawaii’s most favored surf spots accessible from the steps of your front yard. This prized and truly sought-after location provides the perfect haven coupled with wide open spaces, and the nearby convenience to restaurants, shops, parks, Waikiki, Diamond Head hiking trails, farmers market, golfing & more. Don’t miss this once in a lifetime opportunity…

3707 Diamond Head Road, Honolulu

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Based on information from the Multiple Listing Service of Hicentral MLS, Ltd. Listings last updated on . Information is deemed reliable but not guaranteed. Copyright: 2023 by HiCentral MLS, Ltd. IDX information is provided exclusively for consumers' personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.