Diamond Head Real Estate

Welcome to Diamond Head, a stunning gem nestled on the southeastern coast of Oahu, Hawaii, just a stone's throw from the vibrant city of Honolulu. This iconic volcanic crater, known in Hawaiian as Leahi, offers not only breathtaking views but also a unique blend of natural beauty and rich cultural history.

Diamond Head is renowned for its striking landscapes, featuring dramatic cliffs, lush greenery, and panoramic vistas of the Pacific Ocean. The area is a paradise for outdoor enthusiasts, with the famous Diamond Head State Monument offering a popular hiking trail that leads to the summit, rewarding trekkers with sweeping views of Waikiki and the sparkling ocean beyond. The trail is accessible year-round, making it a must-visit for both locals and tourists alike.

Beyond its natural allure, Diamond Head is steeped in history. The crater was formed over 300,000 years ago and has served various roles throughout Hawaiian history, including a military lookout during World War II. Today, remnants of these historical sites can be explored, adding a layer of intrigue to your visit.

Living in Diamond Head means embracing a lifestyle that harmonizes with nature. The neighborhood features charming homes with stunning ocean views, and the nearby beaches offer a serene escape for swimming, surfing, and sunbathing. With its proximity to Honolulu, residents enjoy easy access to world-class dining, shopping, and cultural experiences while still being able to retreat to the tranquility of this picturesque locale.

Experience the magic of Diamond Head, where every day is a celebration of Hawaii's natural beauty and vibrant culture. Whether you’re looking to buy a home or simply explore, this enchanting area is sure to leave a lasting impression.

Newest Listings in Diamond Head

$1,475,000

3 Beds ⋅ 3 Baths ⋅ 202615490 MLS ⋅ FS - Fee Simple Tenure

Discover island living in the heart of Kaimuki with this spacious 3-bedroom, 2.5-bathroom CPR single-family home. Located right across from Kapaolono Community Park, you'll enjoy a peaceful, private setting just moments from urban conveniences. The functional, open-concept floor plan seamlessly connects the living and dining spaces—perfect for gathering and entertaining. Highlights include generous closet space throughout, light-filled bedrooms, and a tranquil primary suite. Conveniently located minutes from kaimuki popular eateries, shops, top schools, and freeway access.

740 11th Avenue Unit B, Honolulu

Listing courtesy of Luxury Homes International.

$1,275,000

3 Beds ⋅ 2 Baths ⋅ 202609335 MLS ⋅ FS - Fee Simple Tenure

Vintage 1940's bungalow located in the super convenient Kapahulu area at the base of Diamond Head Crater. This charming home with many original features, that made it so cute, are intact and has been meticulously maintained throughout the years. Kitchen and bathrooms have been remodeled to todays standards... New fixtures, new appliances - including a gas range, AC's and ceiling fans in each room, new cabinetry, LVP flooring, fresh paint, lighting etc. makes this a perfect move-in ready home. Nicely landscaped exterior with full grassy areas, beautiful mango tree, fully fenced and gated yard, multiple tandem car parking with a laundry / storage room behind the carport are all features that make this a great property! There is a large concrete patio off the laundry room... possible future home office or additional bedroom? Usuable, landscaped yard with a large mango tree for cool shade. Definitely a classically adorable, move-in ready property on the outskirts of Waikiki!

3327 Catherine Street, Honolulu

Listing courtesy of REMAX Hawaii.

$5,200,000

4 Beds ⋅ 5 Baths ⋅ 202615535 MLS ⋅ FS - Fee Simple Tenure

Your own Kahala retreat on the secluded Ahina Street awaits with this expansive single level, 4 bedroom, 4.5 bath unit with pool. Rooms are split into 2 wings for privacy. Call your agent and take a look!

559 Ahina Street, Honolulu

Listing courtesy of Chaney Brooks Residential LLC.

$1,750,000

5 Beds ⋅ 3 Baths ⋅ 202615465 MLS ⋅ FS - Fee Simple Tenure

Built in 2016 and upgraded in 2026, this 5-bedroom, 3-bath home offers a flexible two-story layout, a spacious fenced grassy yard and parking for up to six vehicles, a combination that is increasingly difficult to find in town. The upper level features 3 bedrooms and 2 full baths, while the lower level offers 2 bedrooms and 1 full bath. Separate entrances provide added privacy and flexibility for a large or multigenerational household, extended family, guests, or potential rental income. Recent upgrades include brand-new luxury vinyl flooring throughout, fresh interior paint, new window AC units and split AC systems. Outside, the large fenced yard provides usable space for pets, entertaining or simply enjoying more outdoor space at home. Ample "off-street" parking accommodates up to six vehicles, and additional storage closets in the garage provide valuable space for tools, equipment and everyday storage. Conveniently located in Palolo with quick access to Kaimuki and Waialae Avenue, UH Manoa, Kahala and Waikiki, along with nearby shopping, dining, schools and freeway access. This rare home offers many options for buyers who need more space and flexibility.

1633 10th Avenue Unit Apt B, Honolulu

Listing courtesy of Coldwell Banker Realty.

$675,000

3 Beds ⋅ 2 Baths ⋅ 202611462 MLS ⋅ FS - Fee Simple Tenure ⋅ Regency Park BLDG.

Welcome to Regency Park! Motivated and ready to sell this rarely available 3 bedroom 2 bath home with over 1200 sq ft of living with treetop views of the canal in the preferred Makai side of building! Unit offers comfort, value and convenience in one of Honolulu's most central locations. Freshly painted, with brand new carpeting in all the bedrooms, and includes two assigned covered parking stalls. Residents enjoy an array of amenities including a swimming pool, recreation room, tennis & pickleball courts, fitness center, private 2-acre park with basketball courts, bbq area and disc golf, onsite manager, 20 guest stalls and 24-hour security. Regency park is located near Waialae avenue restaurants and cafes, supermarkets, boutique shops and freeway access. This home is just minutes from University of Hawaii and walking distance to Chaminade University and Saint Louis School, making it an excellent opportunity for homeowners and investors alike. Building is pet-friendly, buyer to do their own due diligence to confirm the buildings pet policy. Competitively priced and offering exceptional value for the location and amenities, this is an opportunity you won't want to miss!

3138 Waialae Avenue Unit 226, Honolulu

Listing courtesy of eXp Realty.

$535,000

1 Beds ⋅ 1 Baths ⋅ 202614934 MLS ⋅ FS - Fee Simple Tenure ⋅ Ilima Apts BLDG.

Located at desirable Pualei Circle in the Diamond Head neighborhood, Ilima Apartments offer peaceful residential living with the best of Honolulu just minutes away. Waikiki Elementary School is within walking distance. Diamond Head, Kapiolani Park, Waikiki Beach, Kaimana Beach, Queen’s Surf and the Honolulu Zoo are all conveniently nearby. Enjoy easy access to some of Honolulu’s favorite cafes, restaurants, bakeries and local eateries along Monsarrat Avenue, Kapahulu and Kaimuki. Assigned storage locker has space for surfboards and bicycles. The condo was beautifully renovated in 2020, including updated plumbing, providing modern comfort and peace of mind. With its tranquil salt water pool, quiet neighborhood setting, walkable access to school, beaches, parks, dining, and everyday conveniences, Ilima Apartments at Pualei Circle offers an exceptional opportunity to enjoy the best of island living in one of Honolulu’s most sought-after locations.

3093 Pualei Circle Unit 208, Honolulu

Listing courtesy of Coldwell Banker Island Prop.

$1,295,000

5 Beds ⋅ 3 Baths ⋅ 202614648 MLS ⋅ FS - Fee Simple Tenure

“Own an original”: The original owner of these beautiful, classic homes in Palolo valley is ready for the next generation of owners, investors, or developers to call this place home. Nestled on the mauka (mountain) side of 10th Avenue, you feel like you are in a special retreat, away from the hustle and bustle of the urban core, yet only 1 mile from Wai’alae Ave in the vibrant neighborhood community of Kaimuki - close to locally owned restaurants, retail shops and bus lines. Two separately metered (water, sewer and electrical) single family homes with an enclosed 2 car garage on 10th Ave. Main home on 10th Ave is a 3 bd / 1.5 bath with an unfinished basement for extra storage or remodel potential and covered lanai. Upper home 2 bd / 1 ba with a spacious, terraced backyard of property with even more potential to extend or build; buyer to do their own due diligence regarding permitting and capacity to build. Conveniently located across from Palolo Elementary, two blocks from Honolulu Fire Dept Station and 4 blocks away from Palolo Community Center with swimming pool, basketball courts and baseball field.

2077 10th Avenue, Honolulu

Listing courtesy of Koi Realty.

$985,000

2 Beds ⋅ 2 Baths ⋅ 202615363 MLS ⋅ FS - Fee Simple Tenure ⋅ Kuliouou Kai Villa BLDG.

Rarely available WATERFRONT residence at Kuliouou Kai Villa, just steps from the beach! Corner unit offers exceptional privacy. Inspiring views over Paiko Lagoon & the Pacific set the backdrop for this stylish and beautifully maintained townhome. An airy living room takes full advantage of the oceanfront setting, with soaring vaulted ceilings and sweeping views. Contemporary kitchen opens to a spectacular private garden, where a travertine patio is surrounded by immaculate landscaping, two fountains, and a bird bath, all fully irrigated. The split-level layout offers two spacious bedroom suites, each with a walk-in closet. Unwind in your primary suite with panoramic views and ample room for a home office and sitting area. Kuliouou Kai Villas is a resort style community with a private pool and beautiful walking paths overlooking a bird sanctuary, and Kuliouou Beach Park. Two parking stalls & storage included.

6109-A Summer Street Unit 6109A, Honolulu

Listing courtesy of Coldwell Banker Realty.

$1,399,000

4 Beds ⋅ 3 Baths ⋅ 202614936 MLS ⋅ FS - Fee Simple Tenure

Rare Opportunity! This unique property features two separate dwellings on a spacious 4,500 sq. ft. lot, offering exceptional flexibility for extended family, guests, or rental income potential. The back residence (approx. 1,008 sq. ft.) includes a versatile 2-bed/2-bath layout, while the front residence (approx. 528 sq. ft.) includes 2-bed/1-bath. Adding further value is an owned photovoltaic system with 25 panels, offering energy efficiency and potential long-term utility savings. Ideally located in the desirable Kapahulu neighborhood, just minutes from Diamond Head, Waikiki and world-class shopping, dining, beaches, and more. Don't miss out on this exceptional opportunity!

3473 Winam Avenue, Honolulu

Listing courtesy of Locations LLC.

$1,825,000

5 Beds ⋅ 3 Baths ⋅ 202614839 MLS ⋅ FS - Fee Simple Tenure

Most homes trade elevation for the view—climb higher, live farther from everything. This Halekoa Drive home rewrites that story: nearly 180 degrees of open ocean and Diamond Head from every level, perched low enough to keep daily life close. Four bedrooms sit upstairs; below, a detached rental unit with its own entrance, bath, and wet bar gives you a flexible lower level - an income offset, a guest suite, or extra room for your Ohana. Sixteen owned solar panels and solar hot water run on net metering, putting the energy math in your favor. A neighborhood park sits just a few blocks off, and the address lands in some of Honolulu's most sought-after public school districts. This house is built for the buyer who wants the unobstructed views without the climb. The home has been tastefully maintained with contemporary flooring, spacious bedrooms, and an EV equipped garage you can pull into after a long day at the beach. You can count on one hand how many homes on the hill like this come to market. Don't miss your chance to stand in this space and feel the tranquility it holds. Call your favorite realtor today for a private showing, and welcome home.

1492 Halekoa Drive, Honolulu

Listing courtesy of Real Broker.

$1,088,000

2 Beds ⋅ 3 Baths ⋅ 202614149 MLS ⋅ FS - Fee Simple Tenure ⋅ Kahala View Estate BLDG.

Tucked among lush tropical greenery, this beautifully upgraded home offers the perfect blend of elegance, privacy, and comfort. Soaring vaulted ceilings and expansive windows fill the interior with natural light, creating a bright and inviting atmosphere. The open-concept living and dining areas flow seamlessly into a custom kitchen featuring Delicatus granite countertops, abundant pantry cabinetry, and a breakfast bar. Commercial-grade Wilsonart flooring, split AC, and an owned 18-panel photovoltaic system provide exceptional style, comfort, and energy efficiency. Two private lower-level bedroom suites offer a peaceful retreat. Move-in ready and located in the gated Kahala View Estates, just minutes from Kahala Mall, beaches, and downtown Honolulu.

1487 Hiikala Place Unit 28, Honolulu

Listing courtesy of Starts International HI, Inc..

$1,050,000

3 Beds ⋅ 2 Baths ⋅ 202614650 MLS ⋅ FS - Fee Simple Tenure

Welcome to this hidden gem, 1878A Mahana Street. Tucked away down a flag lot in the heart of Palolo Valley, this well-maintained, single level, 3-bed, 2-bath home is ready for its next chapter. Whether you're looking to move right in or bring your vision to life, the possibilities are endless. The property enjoys a quiet retreat from the street allowing you to curate your own private oasis while still remaining conveniently close to everything Honolulu has to offer. Inside, the thoughtfully designed 1,445 sq. ft. floor plan features 2 living spaces, perfect for entertaining and hosting your favorite people. A natural cross breeze and tons of natural light move through the home, creating a comfortable living environment year-round. The flexible indoor-outdoor space is great for gardening, grilling, or simply relaxing after a long day. With 2 carports and a driveway, this home can hold up to 4 cars with additional parking on the street. Opportunities like this are becoming increasingly rare, especially in a desirable & convenient area like Palolo.

1878-A Mahana Street, Honolulu

Listing courtesy of Keller Williams 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: 2026 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.