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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.

$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.

$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.

$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.

$6,995,000
5 Beds ⋅ 6 Baths ⋅ 202528401 MLS ⋅ FS - Fee Simple Tenure
A rare opportunity to own one of Diamond Head's most captivating oceanfront estates at a newly reduced rate; truly the best value Diamond Head. This Balinese-inspired masterpiece blends timeless island elegance with modern sophistication. Designed to embrace Hawaii's indoor-outdoor lifestyle, the residence opens seamlessly to panoramic ocean vistas and the rhythmic sound of the waves. This five-bedroom sanctuary showcases bespoke finishes, natural textures, and an architectural flow that evokes both serenity and grandeur. The primary suite offers breathtaking ocean views and a spa-like en-suite retreat, while a private guest apartment-complete with its own entrance-provides stunning views of Diamond Head and total privacy for family or guests. Outdoors, a private tropical oasis awaits. Surrounded by lush landscaping, the grounds feature a resort-style pool, elevated spa, fire pit, and tranquil koi pond, creating an atmosphere of peaceful indulgence. Gated and secure, yet minutes from Waikiki Beach and Diamond Head State Monument, this rare offering perfectly balances luxury, seclusion and convenience. it is the premier value in Diamond Head's pristine oceanfront enclave.

4240 Kaikoo Place, Honolulu

Listing courtesy of Coldwell Banker 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.

$8,000,000
5 Beds ⋅ 6 Baths ⋅ 202507863 MLS ⋅ FS - Fee Simple Tenure
It's all about the view...Rare 360-degree panorama that captures breathtaking vistas in every direction. One-of-a-kind retreat designed to immerse you in nature's beauty from glorious Koko Head sunrises to dramatic sunsets over Diamond Head... and mesmerizing wave breaks along the coastline stretch. Improved in 2018, Built in 2008,w/Geoffrey Lewis, Architect. Thoughtful formal, informal and quiet spaces including ground floor suite w/wet bar& separate zoned AC. Heated spa & infinity pool - a masterful design w/its edge seamlessly blending into the horizon as if it flows directly into the ocean below. Easy access to incredible surf breaks and stunning Association's saltwater pool carved in the lava cliff that defines Black Point's charm. Gated and secured community for privacy. This site carries a legacy of ingenuity and distinction, once home to George Hemmeter, renowned inventor whose visionary spirit is echoed in its unique character and reflects the extraordinary essence of his contributions. Once-in-a-lifetime opportunity to own a piece of a prestigious storied history and experience the luxury and serenity that only this exceptional residence can offer.

4125 Black Point Road, Honolulu

Listing courtesy of Coldwell Banker Realty.

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.