Diamond Head Real Estate

Welcome to Diamond Head, a stunning gem nestled on the southeastern coast of Oahu, Hawaii. Renowned for its iconic volcanic crater, Diamond Head is not just a breathtaking natural wonder; it’s also a vibrant community that offers a unique blend of island living and urban convenience.

As you explore this enchanting region, you’ll be captivated by its lush landscapes and panoramic ocean views that stretch as far as the eye can see. The famous Diamond Head State Monument, a must-visit for both locals and tourists, features a hiking trail that leads to the summit, rewarding adventurers with spectacular vistas of the Pacific Ocean and the Honolulu skyline. Whether you’re an avid hiker or simply seeking a leisurely stroll, the beauty of Diamond Head is sure to inspire.

Living in Diamond Head means embracing a lifestyle filled with outdoor activities, from surfing the world-renowned waves at nearby beaches to enjoying serene moments at Kapiolani Park. The area is also home to an array of charming cafes, boutique shops, and local eateries that showcase the rich flavors of Hawaiian cuisine.

Additionally, Diamond Head’s prime location in Honolulu offers easy access to the city’s bustling amenities, cultural attractions, and vibrant nightlife, all while maintaining a laid-back island vibe. With its stunning natural beauty, rich history, and welcoming community, Diamond Head is more than just a destination; it’s a place where dreams of island living come to life. Whether you’re looking to buy, sell, or simply explore, Diamond Head is waiting to welcome you home.

Newest Listings in Diamond Head

$2,275,000

5 Beds ⋅ 4 Baths ⋅ 202615526 MLS ⋅ FS - Fee Simple Tenure ⋅ 0 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

$50,000

2 Beds ⋅ 2 Baths ⋅ 202615775 MLS ⋅ LH - Leasehold Tenure ⋅ 1 DOM ⋅ Kahala Beach BLDG.

Enjoy the beauty and serenity of Kahala Beach from this spacious 1,555 sq ft, 2-bedroom, 2-bathroom ground-floor condominium at Kahala Beach Apartments. Ideally located on Kahala Avenue, this fully furnished residence is just steps from the beach and conveniently close to Kahala Hotel, Kahala Mall, restaurants, shopping, and easy access to Honolulu. The generous floor plan features an enclosed lanai that expands the living space and offers a peaceful garden setting. The unit is fully furnished with comfortable Hawaiian-style décor and includes a king bed in the primary bedroom, two queen beds in the second bedroom, and two sofa beds, providing ample space for family and guests. Enjoy the convenience of ground-floor living with easy access to the pool and recreation areas, plus the ability to bypass the elevator. The property also includes one covered garage parking stall and storage. A unique opportunity to own in one of Honolulu’s desirable beachfront communities. The lease term ends July 2027, but you can rent from Kamehameha schools after providing additional time to enjoy or utilize the property. Maintenance fee includes all utilities. Lease rent paid til October 2026!

4999 Kahala Avenue Unit 148, Honolulu

$2,395,000

5 Beds ⋅ 3 Baths ⋅ 202615817 MLS ⋅ FS - Fee Simple Tenure ⋅ 1 DOM

Built in 2022 and ideally positioned on lower Sierra Dr., this modern 5-bedroom, 3-bath home captures unobstructed, sweeping ocean, 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. All decks repainted.

3616 Sierra Drive, Honolulu

$2,050,000

6 Beds ⋅ 3 Baths ⋅ 202615523 MLS ⋅ FS - Fee Simple Tenure ⋅ 1 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 ⋅ 4 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 ⋅ 5 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

$1,475,000

3 Beds ⋅ 3 Baths ⋅ 202615490 MLS ⋅ FS - Fee Simple Tenure ⋅ 5 DOM

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

$1,275,000

3 Beds ⋅ 2 Baths ⋅ 202609335 MLS ⋅ FS - Fee Simple Tenure ⋅ 6 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 ⋅ 7 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 ⋅ 7 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

$675,000

3 Beds ⋅ 2 Baths ⋅ 202611462 MLS ⋅ FS - Fee Simple Tenure ⋅ 7 DOM ⋅ 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

$535,000

1 Beds ⋅ 1 Baths ⋅ 202614934 MLS ⋅ FS - Fee Simple Tenure ⋅ 7 DOM ⋅ 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

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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.