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$55,000,000
11 Beds ⋅ 11 Baths ⋅ 202520629 MLS ⋅ FS - Fee Simple Tenure ⋅ 344 DOM
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
$43,000,000
5 Beds ⋅ 7 Baths ⋅ 202520630 MLS ⋅ FS - Fee Simple Tenure ⋅ 344 DOM
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
$37,500,000
5 Beds ⋅ 9 Baths ⋅ 202528159 MLS ⋅ FS - Fee Simple Tenure ⋅ 266 DOM
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
$26,500,000
5 Beds ⋅ 8 Baths ⋅ 202603726 MLS ⋅ FS - Fee Simple Tenure ⋅ 212 DOM
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
$19,800,000
202604171 MLS ⋅ FS - Fee Simple Tenure ⋅ 197 DOM
Discover a rare and extraordinary offering—over 45,000 square feet of prime buildable land along prestigious Kahala Avenue. This expansive oceanfront property, comprised of two parcels (TMKs: 1-3-5-006-014 & 1-3-5-006-009), boasts 126 linear feet of direct beachfront access, inviting you to experience breathtaking, sunsets, and over a mile of direct serene sandy shoreline. Recently improved with grading and new perimeter walls, this R-5-zoned property is an exceptional canvas for a grand estate, private compound, or luxury family residence. Short distance to the Kahala Hotel or Waialae Country Club, embrace the ultimate island lifestyle in one of Oahu’s most prestigious neighborhoods. Nestled down a private lane, this exclusive setting offers privacy, gorgeous ocean views, and an opportunity to craft an oceanfront legacy in one of Hawaii’s most coveted locations. Don’t miss this chance to build your dream home in Kahala.

4767 Kahala Avenue Unit B&D, Honolulu
$17,500,000
5 Beds ⋅ 7 Baths ⋅ 202609193 MLS ⋅ FS - Fee Simple Tenure ⋅ 126 DOM
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
$15,950,000
5 Beds ⋅ 7 Baths ⋅ 202615041 MLS ⋅ FS - Fee Simple Tenure ⋅ 35 DOM
Set on one of Hawaii Loa Ridge's most coveted lots, this five bedroom, six and one half bath residence delivers uninterrupted views of Diamond Head, the Pacific Ocean, and Honolulu's coastline from nearly every room, with complete privacy from neighbors and the street. Award-winning architect Jeff Long paired steel-and-concrete construction with interiors built by artisans whose past work spans ultra-luxury yachts and the ateliers of Chanel, Cartier, and Hermes. Book-matched travertine and marble carry through the home, alongside Spinneybeck and Holly Hunt Italian leather walls and Molteni closet systems. A pneumatic glass elevator connects the levels, and a private theater and wine cellar round out the entertaining spaces. The Pininfarina-designed kitchen centers on a Taj Mahal quartzite island, Snaidero cabinetry, dual Sub-Zero refrigerators, and Gaggenau appliances. Outside, a saltwater infinity pool and spa sit within a landscaped lanai framed by the same sweeping views. German-engineered shutters, a full security system, and 24-hour gated access make this a genuine lock-and-go estate.

360 Puuikena Drive, Honolulu
$15,000,000
202524575 MLS ⋅ FS - Fee Simple Tenure ⋅ 316 DOM
Kahala Avenue ocean front property. Opportunity to design/build your luxury residence. All Permits, Certifications, Assessments, Plans & Surveys have expired. Removal of Condominium Registration & Map, Chapter 5148, Declaration of CPR, Bylaws on 2/19/25. As-Is. Buyer to do own due diligence.

4607 Kahala Avenue, Honolulu
$13,800,000
5 Beds ⋅ 7 Baths ⋅ 202611456 MLS ⋅ FS - Fee Simple Tenure ⋅ 87 DOM
The Paiko Retreat stands as a true Architectural Masterpiece after a comprehensive restoration. Sitting on over an acre of mature landscaping, Kanewai Spring, waterfalls, and koi ponds, there’s no place quite like this home. A unique estate designed by John Hara in 1983, Hara brings an intentional, open-air feeling to this home like he built at the Honolulu Museum of Art, UH West Oahu, and Punahou School. Spanning 9,295 square feet, the interior is vast, yet warm and deliberate. A dedicated primary wing and private sitting room tucked away from the main entertaining areas, plus four guest bedrooms, each with its own ensuite bath and connected by a custom glass elevator. A media room, family room, and private offices provide space for everyone. The transition to the sweeping lanais is seamless. The grounds carry the calm of a private Japanese resort, with gardens and water features weaving through the property. You have direct frontage on Kanewai Spring feeding into Historic Paiko Lagoon. Because it’s a state wildlife sanctuary, the view is strictly nature—quiet and serene. Evenings here are best spent on the lanai watching shorebirds wade through the shallow waters.

6015 Kalanianaole Highway, Honolulu
$12,500,000
5 Beds ⋅ 4 Baths ⋅ 202613905 MLS ⋅ FS - Fee Simple Tenure ⋅ 53 DOM
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
$12,000,000
6 Beds ⋅ 4 Baths ⋅ 202520628 MLS ⋅ FS - Fee Simple Tenure ⋅ 344 DOM
Exceptional Beachfront Luxury on Honolulu’s Iconic Diamond Head! A rare gem on one of Honolulu’s most coveted stretches of beach, this stunning beachfront estate offers an unparalleled lifestyle. Nestled on the prestigious Diamond Head coastline, this exquisite residence sits directly on a pristine white sand beach with crystal-clear waters perfect for snorkeling and a variety of ocean activities. This turnkey home is a true Kama'aina re-treat, offering a balance of comfort and coastal beauty. The property boasts a meticulously manicured lawn, lush tropical landscaping, and an elevated private yard that ensures both serenity and seclusion. Gated entryways provide ultimate privacy and security, making this an ideal retreat. This rare opportunity is exclusively available for purchase either in conjunction with the neighboring property at 3735 Diamond Head Road OR after the larger estate has sold.

3735 Diamond Head Road Unit A, Honolulu
$11,250,000
202613400 MLS ⋅ FS - Fee Simple Tenure ⋅ 63 DOM ⋅ Kapahulu Vista Apts BLDG.
$11,250,000 or Best Offer! 567 Kapahulu is prominently located in the heart of the Kapahulu Corridor, at the corner of Kapahulu and Campbell Avenue. It is amongst a high concentration of neighborhood amenities, restaurants, grocery stores, and residences. Minutes away from Waikiki and less than one mile from the H1 freeway, this property is easily accessible for both locals and tourists. 567 Kapahulu had a comprehensive makeover in 2019 with a new section that was rebuilt. It's very well maintained and has the potential to add more SF on the 2nd floor and a possible addition of sidewalk seating fronting Kapahulu Avenue. Currently, 567 Kapahulu is 100% occupied with a majority of tenants on long-term leases and holds a solid NOI. In addition to the on-site & street parking, a 55-stall public parking lot directly across the street ensures plenty of convenience for customers. Don't let this investment slip by! Contact us today for further details!!

567 Kapahulu Avenue, Honolulu
$10,700,000
3 Beds ⋅ 3 Baths ⋅ 202525708 MLS ⋅ FS - Fee Simple Tenure ⋅ 297 DOM ⋅ 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
$10,700,000
3 Beds ⋅ 3 Baths ⋅ 202525685 MLS ⋅ FS - Fee Simple Tenure ⋅ 297 DOM ⋅ 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
$10,500,000
5 Beds ⋅ 7 Baths ⋅ 202608794 MLS ⋅ FS - Fee Simple Tenure ⋅ 98 DOM
Introducing a rare new luxury construction in the heart of Kahala, where no detail has been overlooked. This stunning estate features a primary residence and guest cottage/gym, both crafted with the finest materials, including custom cedar ceilings, copper gutters, high-quality composite roofing, and lava rock accents throughout. Designed for the discerning buyer, the property boasts a resort-style pool, whirlpool, koi pond, custom cedar gazebo, and expansive lava tile patios and walkways. Inside, you will find a marble primary bath tub, custom wood ceilings, lava tile feature walls, acoustic wall paneling, vanities, and interior tiling of the highest caliber. A true one-of-a-kind opportunity to own a brand new, thoughtfully designed luxury home.

4561 Aukai Avenue, Honolulu

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.