Diamond Head Homes for Sale

Welcome to Diamond Head, one of Honolulu's most iconic and sought-after neighborhoods, where the breathtaking beauty of nature meets the vibrant spirit of island living. Nestled on the southeastern coast of Oahu, Diamond Head is renowned for its stunning volcanic crater, which offers panoramic views of the Pacific Ocean and the lush landscapes that surround it. This picturesque region is not only a haven for outdoor enthusiasts, with its hiking trails and pristine beaches, but also a cultural epicenter, boasting a rich history and a diverse community.

As you explore the homes for sale in Diamond Head, you'll discover a variety of architectural styles that reflect the area's unique charm. From luxurious oceanfront estates to cozy bungalows nestled among tropical gardens, there’s something for everyone in this enchanting locale. Many properties feature expansive windows that invite the warm Hawaiian sun and gentle ocean breezes into your living space, creating an atmosphere of tranquility and relaxation.

Living in Diamond Head means enjoying a lifestyle filled with adventure and leisure. Spend your days surfing the world-class waves at nearby beaches, indulging in local cuisine at charming cafes, or strolling through the vibrant neighborhood markets. With its close proximity to downtown Honolulu, residents enjoy easy access to shopping, dining, and cultural attractions, all while being surrounded by the natural beauty that makes Hawaii a paradise.

Don’t miss your chance to own a piece of this idyllic community. Explore the homes for sale in Diamond Head today and find your dream sanctuary in this tropical oasis!

Newest Diamond Head Homes for Sale

$898,000

3 Beds ⋅ 2 Baths ⋅ 202616024 MLS ⋅ FS - Fee Simple Tenure ⋅ 1 DOM

3 Bedroom, 1 bath upstair and below, similar to a studio style with 1 bathroom.Diamond Head, Waikiki and mountain views. Near busline, schools and stores, restaurant and banks. To be sold in "As Is" condition no repairs to do. No Seller Disclosure Statement to be provided. Sale of property is subject to finding replacement home for the Seller

1768 Palolo Avenue Unit H, Honolulu

$2,800,000

4 Beds ⋅ 3 Baths ⋅ 202615777 MLS ⋅ FS - Fee Simple Tenure ⋅ 1 DOM

Perched within the gated community of Hawaii Loa Ridge, 869 Ikena Circle captures sweeping ocean, coastline, and mountain views from an elevated East Honolulu setting. Expansive windows fill the home with natural light and showcase the blue Pacific from the spacious main living areas, which extend to a covered lanai for effortless indoor-outdoor living. Renovated in 2025, the thoughtfully designed floor plan offers a bedroom and full bath on the main level, along with a versatile office/den, while upstairs you'll find two generously sized en-suite bedrooms offering privacy and separation. Step outside to your own private pool surrounded by tropical greenery—the perfect setting to relax, entertain and take in the island surroundings. Additional highlights include 86 owned photovoltaic panels, a laundry room, and a 2 car garage with more covered parking in front. Residents of Hawaii Loa Ridge enjoy 24-hour gated security along with community tennis courts, a clubhouse, playground, BBQ areas and access to the Hawaii Loa Ridge hiking trail. A rare opportunity to enjoy privacy, space, security, and panoramic views in one of East Honolulu's most sought-after gated neighborhoods!

869 Ikena Circle, Honolulu

$2,000,000

3 Beds ⋅ 3 Baths ⋅ 202615383 MLS ⋅ FS - Fee Simple Tenure ⋅ 2 DOM

RARELY AVAILABLE - LOWER WAIALAE IKI NEXT TO THE PARK!! This renovated 3bed/3bath home is located in desirable Waialae Iki and features an open floorplan, panoramic ocean views, quartz counter tops, large designer kitchen, recessed lighting, custom cabinets, chandeliers, newer appliances, gas cooktop, laundry room, large jacuzzi, ample storage, split AC's, built-in shelves, Diamond Head/Ocean views, cool trade winds, mango tree, and a large rooftop space perfect for nightly sunsets & entertaining family, friends, & children! This home is located just steps from Waialae Iki Neighborhood Park, and is conveniently located near Kahala Mall, Waialae Country Club, Aina Haina Shopping Center, Kahala Beach, University of Hawaii, Chaminade, Diamond Head, Kaimuki restaurants, schools, grocery stores, parks, bus stops, beaches & more...Don’t miss this opportunity!!

4846 Analii Street, Honolulu

$2,275,000

5 Beds ⋅ 4 Baths ⋅ 202615526 MLS ⋅ FS - Fee Simple Tenure ⋅ 2 DOM

MUST SEE! This stunning Kapahulu residence offers a fresh, modern and cohesive living environment with thoughtful updates throughout - providing the peace of mind and feel of a truly renewed home. With an additional living space downstairs, this flexible two-story floor plan offers excellent versatility for multigenerational living, guests or a variety of lifestyle needs. Enjoy a newly landscaped yard, enhanced with exterior lighting and irrigation, creating a beautiful and functional outdoor space for relaxing or entertaining. Generous parking, including a covered carport and additional on-site parking. Walk to Safeway, Starbucks, dining and everyday conveniences with Waikiki, Diamond Head and beaches just minutes away. A rare opportunity to own a truly move-in-ready home in one of Honolulu's most convenient and sought after neighborhoods.

3237 Olu Street, Honolulu

$2,395,000

5 Beds ⋅ 3 Baths ⋅ 202615817 MLS ⋅ FS - Fee Simple Tenure ⋅ 3 DOM

Built in 2022 and ideally positioned on lower Sierra Dr., this modern 5-bed, 3-bath home captures unobstructed, sweeping coastline & city views from this perimeter lot. Thoughtfully designed to take advantage of the views and natural light, the home offers a flexible floor plan well suited for everyday living, entertaining, guests, or extended family. Entry level offers large glass sliding doors opening to a large lanai off the kitchen and living areas and a bedroom with full bath. Lower level features a second open living room with the additional 4 bedrooms, 2 baths, laundry and 2 additional lanai's, plus a landscaped Living wall off the bedroom glass sliding doors. High ceilings, sprinklers, ceiling fans and privacy make this home feel like it's perched on the edge of the world. Enjoy the benefits of newer construction in one of Honolulu's most established hillside neighborhoods, just mins from Kaimuki, Waialae Ave, dining, shopping, schools, and freeway access. The property includes a 2-car carport plus 2 additional guest parking stalls—a valuable convenience in the area. Driveway is shared. Lower yard grated and perfect for chairs, firepit and sunset views.All decks repainted.

3616 Sierra Drive, Honolulu

$2,050,000

6 Beds ⋅ 3 Baths ⋅ 202615523 MLS ⋅ FS - Fee Simple Tenure ⋅ 3 DOM

Views, convenience and privacy! Minutes from Kahala Mall, schools, medical clinics and H-1 freeway access, this lower Waialae Nui Ridge home offers views of the sparkling Kahala coastline, Diamond Head and Waikiki skyline. Flexible SINGLE LEVEL floorplan includes 6 bedrooms, 3 bathrooms and a spacious family room. Enjoy mornings and unwind in the evenings on the covered view lanai. A variety of mature fruit trees enhance the yard with room to garden. Wonderful corner location with driveway on Uhi Place.

1688 Halekoa Drive, Honolulu

$1,448,000

3 Beds ⋅ 2 Baths ⋅ 202615153 MLS ⋅ FS - Fee Simple Tenure ⋅ 6 DOM

A Timeless and Classic Home … Perched above Center Street in sought-after Wilhelmina, this beautifully updated vintage home blends timeless character with thoughtful modern enhancements. Originally built in 1928 and extensively renovated in 2015, the residence retains its distinctive charm while offering comfortable contemporary living. High ceilings, abundant windows, and beautiful wood flooring create a warm, inviting atmosphere filled with natural light. The flexible lower-level 3rd bedroom/studio space is a feature incorporating natural boulders into its design and offering its own wetbar and beautifully finished on-suite bath all add an elevated touch. On the main level, step outside to an expansive deck ideal for morning coffee, sunset gatherings, and entertaining which you’ll enjoy while taking in views from Palolo Valley, the city and ocean all adding to its appeal. Conveniently located near the entertainment of Kaimuki's dining, shopping and easy access to the freeway.

1439 Center Street, Honolulu

$1,400,000

3 Beds ⋅ 2 Baths ⋅ 202615578 MLS ⋅ FS - Fee Simple Tenure ⋅ 7 DOM ⋅ Kalani Iki Estates BLDG.

Tucked away in a cool, quiet & peaceful neighborhood, Kalani Iki Estates feels uniquely special as you arrive through the lush tree-lined community. This bright, modern 3-bedroom, 2-bath split-level home has been exceptionally maintained & thoughtfully updated. Soaring high ceilings & wrap-around floor-to-ceiling windows welcome you home to a contemporary floor plan, natural light & garden views throughout. Features & upgrades include a re-imagined kitchen with new quartz counter-tops & updated appliances, a dedicated dining space, luxury vinyl flooring, all-new windows & doors throughout, upgraded lighting, roller & zebra shades, two split A/C units & more. Three bedrooms are positioned on the upper-level for added privacy, plus a walk-in storage & walk-in laundry room. This home includes two covered parking stalls. Furnishings available for purchase to make this a turn-key package. Kalani Iki Estates includes landscaping & trash service, an on-site swimming pool, large covered entertainment space & a newly refurbished pickleball court. Minutes to Kahala, Hawaii Kai, urban Honolulu & beyond, this exceptional home in a truly special location is one you won't want to miss.

1500 Kalaniiki Street Unit 13, Honolulu

$1,275,000

3 Beds ⋅ 2 Baths ⋅ 202609335 MLS ⋅ FS - Fee Simple Tenure ⋅ 8 DOM

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, large mango tree for cool shade, 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 extension for a future home office or additional bedroom? Definitely a classically adorable, move-in ready property on the outskirts of Waikiki!

3327 Catherine Street, Honolulu

$5,200,000

4 Beds ⋅ 5 Baths ⋅ 202615535 MLS ⋅ FS - Fee Simple Tenure ⋅ 9 DOM

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

$1,750,000

5 Beds ⋅ 3 Baths ⋅ 202615465 MLS ⋅ FS - Fee Simple Tenure ⋅ 9 DOM

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

$1,295,000

5 Beds ⋅ 3 Baths ⋅ 202614648 MLS ⋅ FS - Fee Simple Tenure ⋅ 10 DOM

“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

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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.