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$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.

$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.

$6,200,000
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.

$37,500,000
5 Beds ⋅ 9 Baths ⋅ 202528159 MLS ⋅ FS - Fee Simple Tenure
The Hemmeter Estate is a rare, oceanfront estate located at the end of Kaikoo Place on Black Point. Featuring an extraordinary 339.45 linear feet of ocean frontage, this property offers one of the most expansive coastal settings in Hawaii, with exceptional frontage in the heart of Kaikoo. Blending Hawaiian natural elements with European Renaissance–inspired design, the residence showcases exceptional craftsmanship throughout. Set on 35,870 sq ft of land, the estate offers approximately 21,266 sq ft of interior living, complemented by extensive covered and open lanais ideal for entertaining. Highlights include cast-bronze entry doors, coffered Venetian-inspired ceilings, Italian perlato marble staircases and flooring, carved and finished on-site, a two-story oceanfront living room, and refined Art Deco bronze detailing. Amenities include a private theater, library, entertaining lounge, and grotto pool. The expansive primary suite spans nearly 5,000 sq ft and features dual dressing rooms, a fitness area, and sweeping coastline views. The Hemmeter Estate is an irreplaceable oceanfront estate distinguished by scale, privacy, and architectural significance.

4324 Kaikoo Place, Honolulu

Listing courtesy of Compass.

$10,700,000
3 Beds ⋅ 3 Baths ⋅ 202525708 MLS ⋅ FS - Fee Simple Tenure ⋅ Kuu Makana@ Diamond Hd BLDG.
This turnkey luxury residence is a rare offering, now enhanced with further upgrades. Encompassing more than 4,000 sf of seamless indoor-outdoor living, the home sits at the foot of Diamond Head in the exclusive oceanfront enclave of Kuu Makana at Diamond Head. Within this private, gated community, the 3-bed + den/3-bath property exemplifies island elegance & refined sophistication. Rich, handcrafted woodwork flows throughout, elevating its timeless aesthetic. The gourmet kitchen is equipped for the discerning chef, showcasing Sub-Zero & Wolf appliances, custom Koa cabinetry & premium countertops. Generous living spaces incl a fireplace, creating a warm & tranquil setting. Expansive bedrooms offer peaceful retreats w/custom shelving, stunning Koa doors, and the convenience of an elevator. Every detail reflects exceptional craftsmanship and thoughtful design. Sustainable feats incl 34 PV panels, 3 TESLA Powerwalls and EV charger. Also features a large 2-car enclosed garage. With unparalleled ocean views, a premier location, and impeccably curated interiors, this home stands alone. This is a rare chance to own a piece of paradise in one of Hawaii’s most coveted coastal communities.

3165 Diamond Head Road Unit 4, Honolulu

Listing courtesy of Caron B Realty.

$43,000,000
5 Beds ⋅ 7 Baths ⋅ 202520630 MLS ⋅ FS - Fee Simple Tenure
Located on Diamond Head Road, Ho‘oluana Estate is one of Honolulu’s last remaining legacy estate-sized properties. Zoned R-7.5 and encompassing nearly 80,000 square feet, the estate features an expansive residences and several open lots, offering sweeping ocean views, private/deeded beachfront access, and exceptional flexibility for development or preservation. Perfectly positioned between Kahala and Waikiki, this property combines luxury, tranquility, and proximity to world-class surfing, shopping, dining, golf, hiking, and more. Neighboring property located at 3735 Diamond Head Road A, is also available for sale, presenting a rare opportunity to establish a landmark estate in one of Honolulu’s most prestigious locations. Property details may not match tax records.

3735- Diamond Head Road, Honolulu

Listing courtesy of Hawaii Life.

$55,000,000
11 Beds ⋅ 11 Baths ⋅ 202520629 MLS ⋅ FS - Fee Simple Tenure
Located on Diamond Head Road, Ho‘oluana Estate is one of Honolulu’s last remaining legacy estate-sized properties, spanning over two acres across two adjacent parcels. Zoned R-7.5 and encompassing nearly 89,120 square feet, the estate features two residences and an open lot, offering sweeping ocean views, beachfront access, and exceptional flexibility for development or preservation. Perfectly positioned between Kahala and Waikiki, this property combines luxury, tranquility, and proximity to world-class surfing, shopping, dining, golf, hiking, and more. Offered as a singular acquisition under TMKs 1-3-1-039-042-0000 and 1-3-1-039-005-0000, Ho‘oluana Estate presents a rare opportunity to establish a landmark estate in one of Honolulu’s most prestigious locations. Property details may not match tax records. Last four digits of the listing TMK do not exist, these are used only for MLS entry purposes.

3735 Diamond Head Road, Honolulu

Listing courtesy of Hawaii Life.

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.