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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.

$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.

$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.

$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.

$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.

$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.