Diamond Head Real Estate

Diamond Head Real Estate

Welcome to Diamond Head, a stunning gem nestled on the southeastern coast of Oahu, Hawaii. Renowned for its iconic volcanic cone and breathtaking ocean views, this vibrant neighborhood offers a unique blend of natural beauty, rich history, and a laid-back lifestyle that perfectly embodies the spirit of island living.

Diamond Head is not just a picturesque landmark; it’s a thriving community filled with charming homes, lush landscapes, and a friendly atmosphere. The neighborhood is primarily residential, featuring a mix of historic cottages and modern homes, all set against the backdrop of the majestic Diamond Head State Monument. Here, residents enjoy easy access to scenic hiking trails that lead to panoramic vistas of the Pacific Ocean and the Honolulu skyline.

The area boasts a rich cultural heritage, with nearby attractions like the Kapiolani Park and the Honolulu Zoo, perfect for families and outdoor enthusiasts. The vibrant local scene includes a variety of dining options, from casual beachside eateries to upscale restaurants, offering a taste of Hawaii’s diverse culinary landscape.

For those who appreciate the arts, Diamond Head is also close to the Honolulu Museum of Art and the famous Waikiki Beach, where you can soak up the sun or catch a wave. With its ideal location, stunning scenery, and welcoming community, Diamond Head is more than just a place to live; it’s a lifestyle. Experience the magic of this enchanting neighborhood and discover why so many call it home.

Newest Listings in Diamond Head

$5,050,000
4 Beds ⋅ 3 Baths ⋅ 202614040 MLS ⋅ FS - Fee Simple Tenure
Nestled on the prestigious Diamond Head neighborhood, offers a large 15,000 sqft lot overlooking Kahala with ocean views. Bring your architect and contractor to design your home. Conveniently located near Kapiolani Park, Diamond Head, Kahala Mall, beaches, and Waikiki, making it an exceptional place to enjoy both tranquility and island living at its best.

633 Hakaka Place, Honolulu

Listing courtesy of Hawaii Resource Realty.

$12,500,000
5 Beds ⋅ 4 Baths ⋅ 202613905 MLS ⋅ FS - Fee Simple Tenure
TIMELESS DIAMOND HEAD BEACHFRONT LIVING. Tucked away at the end of a private drive on highly coveted Diamond Head Beach, this classic 5-BD, 4-BA beachfront residence presents a rare opportunity to own in one of Oahu's most iconic oceanfront enclaves. Situated on a 15,398 sq ft parcel, the home enjoys spectacular unobstructed ocean views, rolling surf, swaying coconut palms & the soothing sounds of the Pacific from an exceptionally private setting. A welcoming courtyard w/ tropical landscaping & signature plumeria tree leads to light-filled interiors w/ vaulted ceilings & an open floor plan showcasing the sparkling azure waters of the Pacific. Expansive living & dining areas flow seamlessly to the oceanfront lanai, grassy seaside lawn, and steps to the water's edge. The kitchen features granite countertops, abundant cabinetry, dine-in seating & a breakfast nook. The oceanfront primary suite enjoys breathtaking views & spa like bath. Four additional bedrooms offer flexibility for family/guests or office. Conveniently located near Kapiolani Park, Diamond HD hiking trails, golf, Farmers Market, Waikiki, restaurants & shopping. A truly rare opportunity to own on Diamond Head Beach.

3735 C Diamond Head Road, Honolulu

Listing courtesy of Coldwell Banker Realty.

$3,600,000
3 Beds ⋅ 3 Baths ⋅ 202612743 MLS ⋅ FS - Fee Simple Tenure
Looking for back up offer. Easy to show. Modern Luxury timeless in Diamond Head. Experience modern island luxury, Beautifully upgraded throughout, this elegant residence features 3 bedrooms, 1 office/ bedroom , and 3 full bathrooms with a spacious, open-concept design filled with natural light. Contemporary finishes, quality craftsmanship, and thoughtful details create a sophisticated yet comfortable living environment. Enjoy the open concept from the main living room open to yard areas while overlooking peaceful, lush gardens that provide exceptional privacy and tranquility. Located on a quiet cul-de-sac in one of Honolulu's most desirable neighborhoods, this move-in-ready home offers the perfect balance of luxury, comfort, and convenience—just minutes from beaches, shopping, dining, and schools.

3942 Kaualio Place, Honolulu

Listing courtesy of Central Pacific Properties Inc.

$4,200,000
4 Beds ⋅ 4 Baths ⋅ 202611048 MLS ⋅ FS - Fee Simple Tenure
Get ready to find your dream home with this stunning Mid Century Modern home designed by Alfred Preis, the renowned Arizona Memorial Architect. Located just a stone's throw from Diamond Head beach, this fabulous home perfectly embodies the indoor/outdoor lifestyle, boasting a salt water pool, spa and an outdoor shower. Whether you love to host parties or prefer intimate gatherings, the multiple dining areas and a built-in bar are tailor-made for entertaining. The kitchen is a chef's paradise featuring dual sinks, Thermador appliances, a double oven and a gorgeous Heath Tile backsplash. Add a touch of green to your culinary endeavors with the accompanying herb garden. The house remains true to the mid-century aesthetic with smartly designed built-ins and offers abundant storage throughout. Convenient features such as upstairs/downstairs washer/dryers, and central AC in the bedrooms underline the thoughtful design. Hau trees provide privacy around the perimeter, with the added bonus of fruit trees including lime, fig and avocado. Don't miss the chance to live in a home that seamlessly blends style, luxury and comfort at Diamond Head.

4072 Kulamanu Street, Honolulu

Listing courtesy of Harcourts Island Real Estate.

$5,560,000
4 Beds ⋅ 4 Baths ⋅ 202604939 MLS ⋅ FS - Fee Simple Tenure
Located in the heart of one of Oahu's most desirable neighborhoods, this exceptional residence offers the Gold Coast lifestyle just one block from the beach. With Diamond Head just above and beautiful Makalei Beach park just steps away, this property offers an ocean lifestyle within a safe, secure and elegant atmosphere. A European-style estate blending elegance and island living, the house welcomes you with a beautiful waterfall, a sparkling pool and stunning Diamond Head and ocean views from the rooftop deck. Designed for intimate living and gracious entertaining, there are 4 generously sized ensuite bedrooms together with multiple patio areas perfect for gathering with family and friends. Inside the home you'll find tropical indoor outdoor living, tall windows inviting Diamond Head into the home as well as lots of natural light. A large Great Room showcases soaring ceilings, marble flooring, a formal dining area, custom gourmet kitchen and a dramatic staircase anchors the space with architectural beauty. Fully transformed with a remodel in 2000, the residence was upgraded with heavily insulted walls, double pane windows, steel construction and a copper tile roof and gutters.

3063 Diamond Head Road, Honolulu

Listing courtesy of Compass.

$17,500,000
5 Beds ⋅ 7 Baths ⋅ 202609193 MLS ⋅ FS - Fee Simple Tenure
This magnificent Diamond Head “Cove Area” beachfront masterpiece harmoniously fuses traditional Hawaiian architectural elements with an open modern lifestyle floorplan. Located on a quiet lane off Diamond Head Road, this home is truly a treasure to behold. The grand reception areas lead out to extensive wraparound lanai areas, a covered grill space, and a beachside seating area—perfect for enjoying sunsets and drinks while taking in the endless views of the Pacific Ocean. The upper level boasts a large primary ocean view bedroom, two additional en-suite bedrooms, elevator, gas generator and an unmatched office with ocean views that you’ll never want to leave. Refreshing pool, lush private landscaping, and unmatched location, style, comfort, and distinction define this Diamond Head gem.

218 Kaalawai Place, Honolulu

Listing courtesy of Coldwell Banker Realty.

$3,100,000
2 Beds ⋅ 2 Baths ⋅ 202607513 MLS ⋅ FS - Fee Simple Tenure
$200,000 PRICE DROP!!!!!!!Step into this historic Kamaaina home that has been upgraded and remodeled. The Koa wood flooring is spectacular and has been restored to its original lustrous beauty. Enjoy the many amenities of this home: Dip in the pool, luxuriate in the hammock, soak in the hot tub, dine on the spacious deck, or b-b-que. The main home can sleep four and the refurbished studio cottage with new bathroom, is private, with a separate entrance and sleeps two. A wonderful alternative to Gold Coast Condominiums that have high maintenance fees. Welcome Home! Shown with listing agent only. One hour notice required.

3025 Diamond Head Road, Honolulu

Listing courtesy of Hawaii Life.

$5,990,000
4 Beds ⋅ 6 Baths ⋅ 202604465 MLS ⋅ FS - Fee Simple Tenure
Experience refined island luxury living in this executive-style 4-bedroom, 5.5-bath residence ideally positioned on the slopes of iconic Diamond Head. Encompassing nearly 5,900 sq ft of interior space on an 11,752 sq ft lot, this impressive home captures beautiful ocean and sunset views while offering exceptional indoor-outdoor living. Expansive lanai areas, complemented by a heated pool and spa, create a private retreat designed for effortless entertaining. Soaring ceilings enhance the home’s grand scale and invite abundant natural light throughout. The chef’s kitchen anchors the main living spaces, while separate guest quarters with a private entrance provide flexibility and privacy. Remodeled by Jeff Long in 1995, this distinguished property blends timeless design with a premier location just moments from Kapiolani Park, the Gold Coast, world-famous beaches, and renowned shopping and dining of Waikiki. A rare offering in one of Honolulu’s most prestigious neighborhoods.

2999 Makalei Place, Honolulu

Listing courtesy of REMAX Hawaii.

$6,900,000
7 Beds ⋅ 8 Baths ⋅ 202601735 MLS ⋅ FS - Fee Simple Tenure
PRICE REDUCED! MOTIVATED SELLER. This luxury home was taken nearly to the studs and rebuilt a few years ago, and it shows. Unobstructed ocean views are framed by 30-foot windows and ceilings spanning the entire front of the house, opening to oversized decks. A rooftop deck adds sweeping views of the coastline, Diamond Head, and the ocean. Quiet, private setting two blocks from Diamond Head Road and a short distance to the beach. Seven bedrooms and six full baths plus two half baths. Includes a separate studio with its own private entrance — one bedroom, one bath, full kitchenette — ideal for multigenerational living, guests, or rental income. Owned 27-panel photovoltaic system keeps energy costs low. Seller financing may be available.

3849 Poka Street, Honolulu

Listing courtesy of Keller Williams Honolulu.

$26,500,000
5 Beds ⋅ 8 Baths ⋅ 202603726 MLS ⋅ FS - Fee Simple Tenure
Experience unmatched sophistication in this one-of-a-kind, award-winning home by Nicholson Companies, now available at an exceptional value—priced below the 2024 appraisal! This modern masterpiece, nestled in the prestigious Cove Area of Diamond Head, offers over 7,465 square feet of living space that seamlessly blends cutting-edge design with island inspiration. From the expansive living areas that capture breathtaking views to the advanced whole-house automation and security systems, this home is a true technological marvel. The chef's kitchen, featuring professional-grade appliances and a spacious butler’s pantry, is a culinary dream. Every corner reveals something extraordinary, from the exquisite interior finishes to the stunning outdoor oasis. This beachfront home represents the pinnacle of island living, now available at an exceptional price that underscores its unmatched quality and prestige. Seize the opportunity to own this extraordinary residence and make it your own private paradise.

213 Kaalawai Place, Honolulu

Listing courtesy of Coldwell Banker Realty.

$6,888,000
6 Beds ⋅ 7 Baths ⋅ 202603331 MLS ⋅ FS - Fee Simple Tenure
BREATHTAKING OCEAN VIEWS take center stage from the moment you step through the front doors of this elevated Spanish-style retreat at the base of world-renowned Diamond Head. Perched above neighboring homes, the property offers rare privacy, open sightlines, and the feeling of a private villa. Inside, graceful arched doorways, soaring ceilings, rich ohia wood floors, and beautiful carpentry reflect the home's timeless character. The layout features multiple living areas, a commercial-style kitchen with stainless steel counters, and three ocean-view bedroom suites with vintage bathrooms, and cedar-lined closets- offering a wonderful opportunity to update and personalize while honoring the home's original charm. Originally built by the Magoon family as a gathering space, the lower level includes two one-bedroom units and a studio, each with separate entrances and access to a shared laundry area. These spaces open to a lush, enclosed garden with fruiting trees and greenery, adding flexibility, income potential, a serene outdoor setting in one of Honolulu's most iconic locations.

3647 Diamond Head Road, Honolulu

Listing courtesy of Marcus Realty.

$6,200,000
3 Beds ⋅ 4 Baths ⋅ 202524260 MLS ⋅ FS - Fee Simple Tenure
This three-story, fairy tale of a home, is your dream come true! Divinely placed on the slopes of Diamond Head, this luxurious, custom built, real life fantasy home, overflows with 3,200 square feet of gorgeous living space; with an additional 745 square feet of purposeful, covered lanai areas. The unforgettable finishes throughout the home, will have you living like royalty with the featured high ceilings to the heavens, and thoughtful layout on every floor. You won’t be able to ignore the newly installed engineered, wood flooring, the newly installed carpet, and you’ll be magnetized by the presentation of the newly painted, interior and exterior. Custom cabinetry made from mahogany wood, teak, and koa, partners perfectly with the home’s gourmet kitchen featuring top-of-the-line appliances, and ample counter space. You may feel the need to pinch yourself because of the options you’ll have to enjoy the majestic Pacific Ocean sunsets and views from your private office, or your panoramic outdoor terrace, or from your refreshing pool or hot tub. This is an extraordinary dwelling that redefines luxury, comfort, and convenience, in Honolulu's most exquisite neighborhood.

3210 Diamond Head Road Unit 4, Honolulu

Listing courtesy of eXp Realty.

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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.