10 most expensive homes for sale in Diamond Head
In Diamond Head the median sale price for homes on the market is about -, however, high-end properties can be listed at a much higher price point. Here are the top ten most expensive homes for sale in Diamond Head (Oahu).
Home
11
bd
10,047
sqft
$55,000,000
11
bd 10,047
sqft
bd 10,047
sqft
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.
Home
6
bd
9,896
sqft
$45,000,000
6
bd 9,896
sqft
bd 9,896
sqft
Home for sale
4505 Kahala Ave Honolulu, Oahu Neighborhood: Kahala Area
Spectacular Oceanfront Estate in Prestigious Kahala– Welcome to a stunning oceanfront estate in Kahala, a rare 1.3-acre retreat from street to sea. With 171 linear ft of breathtaking ocean frontage, this newly reimagined home blends contemporary design w/Hawaii’s natural beauty. A gated entrance leads to a grand motor court, setting the tone for exclusivity. Inside the 10,000 sq ft, single-level HM, rich Burma Teak, soaring ceilings, & floor-to-ceiling glass create a seamless indoor-outdoor connection. Walls of glass pocket away, revealing uninterrupted ocean views. The expansive oceanfront lanai, spanning 5,000 sq ft, is designed for intimate gatherings or grand entertaining, featuring a sunken wet bar, built-in BBQ, & multiple lounge areas. The primary suite is a private retreat w/ lanai access & a spa-like bath wrapped in stone. Each guest suite offers its own peaceful escape, w/ separate living areas & serene garden or ocean views. A chef’s kitchen, resort-style beachside pool & spa, & meticulous craftsmanship complete this one-of-a-kind estate. Thoughtfully designed & impossible to replicate, this is oceanfront living at its finest in one of Hawaii’s most prestigious enclaves.
Home
5
bd
6,213
sqft
$43,000,000
5
bd 6,213
sqft
bd 6,213
sqft
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.
Home
4
bd
5,226
sqft
$34,000,000
4
bd 5,226
sqft
bd 5,226
sqft
A Rare Diamond Head Estate with Timeless Elegance and Botanical Distinction- The legacy estate that reflects decades of thoughtful ownership and unmatched care. Lovingly maintained and meticulously upgraded, this refined residence sits on an expansive 34,157 sq ft lot and showcases an extraordinary level of craftsmanship, preservation, and pride. Honoring the property’s architectural heritage while introducing modern enhancements that elevate daily living. From the custom woodwork, curated interiors, and peaceful lanais, every element exudes quality and intention. Central to the plan of the garden, which was meant to create “an oasis in the midst of chaos”, were water features and arbors, which bring shade and structure to the garden with the addition of terraces connected by a winding path. The fountains and water features add visual beauty to the garden, as well. Tucked into the side of one of the lower hillside terraces, the path wanders up to and around a pilates studio and guest cottage. The grounds are a living masterpiece. Breathtaking panoramic ocean and coastal views, minutes from Waikiki resort amenities, private clubs, and beautiful beaches.
Home
5
bd
7,324
sqft
$26,500,000
5
bd 7,324
sqft
bd 7,324
sqft
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.
Home
5
bd
5,578
sqft
$17,500,000 ▼ $2,300,000
5
bd 5,578
sqft
bd 5,578
sqft
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.
Home
5
bd
8,795
sqft
$16,800,000 ▼ $2,000,000
5
bd 8,795
sqft
bd 8,795
sqft
Newly priced at a fraction of the cost to rebuild! Situated on one of the most desired lots in Hawaii Loa Ridge, Kaimana Hila o?ers complete privacy and unobstructed views of Diamond Head, the Pacific Ocean, and Honolulu’s coast from nearly every room. Designed by award-winning architect Je? Long, this residence combines resilient steel-and-concrete construction with interiors crafted by artisans known for their work on ultra-luxury yachts and couture boutiques. Exquisite details like Spinneybeck Italian leather walls, custom closets by Molteni & C Dada, and vein-matched travertine marble bathrooms showcase luxury at every turn. At its heart, a Pininfarina-designed kitchen with Snaidero cabinetry and Gaggenau appliances elevates daily living and entertaining alike. Outside, an expansive lanai with a saltwater infinity pool and hot tub, framed by lush landscaping and breathtaking views, creates a resort-style sanctuary. German-engineered hurricane shutters, a professional security system, and a gated community with 24hr security make this a true lock-and-go residence—o?ering unmatched luxury and refinement in Honolulu.
Home
4
bd
2,836
sqft
$12,600,000
4
bd 2,836
sqft
bd 2,836
sqft
Home for sale
3841 Pukalani Pl Honolulu, Oahu Neighborhood: Wilhelmina
Rare development opportunity in highly desirable Wilhelmina Rise! This property features a huge R-5 zoned lot with the potential to build up to 8 CPR single-family homes (subject to approval). The CPR process is already underway, with several building permits currently pending approval. Existing structure has an open permit, pending on a revision/addition permit for the basement. Prime location just minutes from Kaimuki, Kahala, and freeway access. Stunning diamond head and ocean views.
Home
6
bd
3,834
sqft
$12,000,000
6
bd 3,834
sqft
bd 3,834
sqft
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.
Home
8
bd
16,268
sqft
$12,000,000
8
bd 16,268
sqft
bd 16,268
sqft
Welcome to the private, gated “DIAMOND HOUSE” a truly one-of-a-kind masterpiece in Hawaii! This luxurious mansion offers over 16,000 sq. ft. sophisticated living space with 8 bedrooms, 9 full bathrooms, and 2 half bathrooms. The estate is designed for the ultimate in luxury living, with a dramatic tropical landscape showcased as living art – complete with a half-moon fountain pool and a cascading custom waterfall. Highlights include:Grand princess staircase leading to a primary suite with breathtaking ocean, Diamond Head and Waikiki views. Swarovski chandeliers and exquisite imported finishes throughout,3000+ bottle wine cellar for collectors, butler’s pantries & wet bars for refined entertaining, 4-car garage + 6 driveway spaces for ultimate convenience when your guests arrives. Beyond the home itself, enjoy the serenity of your private paradise – hiking among plumeria, listening to Hawaiian birdsong, and watching butterflies drift through the gardens. This iconic estate was crafted by the legendary developer Jack Myers, blending timeless elegance with unmatched craftsmanship. Gated entry ensures both privacy and security for your family and guests. Don't miss this opportunity!
* information deemed reliable, but not guaranteed
Land
0.460
acres
$4,880,000
0.460
acres
acres
Land for sale
4744 Kahala Ave Honolulu, Oahu Neighborhood: Kahala Area
Prime Kahala Avenue location – this expansive estate-sized lot spans over 20,000 square feet and is ready for
you to create your dream home. The generous space offers a range of possibilities, including the option to add
a separate pool house for guests or family, a pickleball or basketball court, or other unique features. Just a
short stroll away, you’ll find beach access leading to Waialae Beach Park, Waialae Country Club, Kahala Beach
Apartments, and the Kahala Hotel & Resort, all adjacent to the Waialae Golf Course. Additionally, Kahala Mall
and convenient freeway access to Downtown or Hawaii Kai are nearby. Opportunities like this, especially in
the sought-after sandy beach area of Kahala, are rare—don’t miss your chance to secure this remarkable
property.
Land
0.115
acres
$1,800,000 ▼ $100,000
0.115
acres
acres
Land for sale
1148 2nd Ave Honolulu, Oahu Neighborhood: Kaimuki
5000 SF PROPERTY ZONED B-2 MIXED USE. ENJOY BEING PART OF THIS VERY BUSY , VIBRANT BUSINESS AND RESIDENTIAL COMMUNITY.of Kaimuki town, loved by residents and tourists. Zoned B 2 Requests buyer does their own due diligence in seeking endless possible uses this parcel offers. Motivated seller. Possible Permitted Uses outdoor and/or indoor amusement or recreation, auto sales/rentals, Biz Services, Catering, Convenience Store, Dance or Music School, Eating Establishment, Financial Institutions, Laboratory Medical or Research, Medical Clinics, Office Buildings, Personal Services, Photo Processing, Photo Studios, Real Estate Offices, Retail Establishments, Minor Repair Est, Travel Agencies, Consulates, Publishing Plants, Restaurants. Build a restaurant and live on premises. There are other uses permitted conditionally. All uses are subj to updates by the DPP Buyer TO DO THEIR OWN DUE DILIGENCE. . Water and Electric Utilities are present and just need to be activated. Check out some of the businesses
in the pictures below. There is so much more, Chaminade University is across the street, as well as numerous restaurants
and schools.
Land
0.381
acres
$2,229,000
0.381
acres
acres
“Pacific Pinnacle Peak” is a remarkable vacant lot located in the prestigious, luxury-gated community of Hawai‘i Loa Ridge. Perfectly positioned in “The Pointe," the ridge’s exclusive separate enclave, with a secondary privacy/security gate, this extraordinary parcel captures sweeping, unobstructed ocean vistas that stretch endlessly across the Pacific from Koko Head to Diamond Head. Currently, the ridge's largest lot available for purchase. With a definite scarcity of vacant lots, it is an irreplaceable canvas for those who seek the finest in island living. While priced below the median cost per sq ft on the ridge, it presents a truly rare opportunity to design & build a signature estate on O‘ahu’s most coveted hillside that reflects your vision of elevated living. With a commanding perspective, the site offers a serene sense while just moments from world-class beaches, shopping, & fine dining. With 24-hour security, a private park, tennis/pickleball courts, a clubhouse, and the prestige of a community known for architectural excellence & natural beauty. "Pacific Pinnacle Peak" stands as a legacy property. An opportunity to LIVE YOUR DREAM LIFE!
Land
1.336
acres
$15,000,000
1.336
acres
acres
Land for sale
4607 Kahala Ave Honolulu, Oahu Neighborhood: Kahala Area
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. 2025 Real Property Tax & Assessment amounts based on 6-CPR parcels. As-Is. Buyer to do own due diligence.
Land
3.336
acres
$2,200,000
3.336
acres
acres
A RARE canvas for a custom vision with gorgeous views and a stunning natural backdrop! This extraordinary 3.3 acre residentially zoned parcel presents an unparalleled opportunity for those seeking privacy, scale, and possibility in one of Oahu's most coveted neighborhoods! This land is currently structured as a four unit CPR, and is being sold as a package with TMKs: 0001–0004 combined. Whether envisioned as a private estate retreat, multi-generational compound , the opportunity for multiple homes through the existing CPR, or legacy property to hold for future generations, this extraordinary parcel is a rare offering not to be missed. Do not walk the property without appointment and signed waiver. Buyer to conduct their own due diligence with the City and County of Honolulu on desired build out.
Land
3.980
acres
$985,000
3.980
acres
acres
Land for sale
2755 Lai Road Honolulu, Oahu Neighborhood: Palolo
Rarely available 3.98-acre parcel on La'i road in Palolo, minutes from the freeway, Kahala Mall, beaches, restaurants, schools, and more. Featuring panoramic ocean and mountain views, this special property provides the opportunity to build your dream home (Zoned P-1 with an allowable 5,000 square foot home). This parcel offers the convenience of town living while affording privacy and the quiet of the country. Located on a private lane in the back of Palolo Valley
Land
0.087
acres
$999,999
0.087
acres
acres
Rare Corner Lot in Kuliouou – Canal Front, Ocean & Mountain Views
Don’t miss this incredible opportunity to own a prime corner lot in the highly desirable Kuliouou neighborhood. This property boasts canal frontage, with stunning ocean and mountain views in a peaceful, residential setting.
Located just a short walk to Kuliouou Beach Park, enjoy paddleboarding, fishing, or relaxing by the water. This lot offers privacy, flexibility in design, and easy access to Hawaii Kai shopping, dining, and schools. A perfect site to build your dream home in paradise!
Land
0.824
acres
$1,570,000 ▼ $130,000
0.824
acres
acres
Function! Convenience! Ease! Improved Pricing! Build your Forever Magnificent Dream home! Secure this opportunity to develop on this spacious lot featuring panoramic, sweeping ocean views from Koko Head to Kahala. Large 35,879sq.ft. lot in Kahala Kua, the newer luxury gated community in East Oahu. Prime location with easy access east to Hawaii Kai or west to Kahala, Ala Moana, Kakaako for shopping, dining, entertainment and excellent schools. Land has been CPR'd 1-3-5-073-119-0001 and 0002 and is offered together. A pristine opportunity you don’t want to miss!
Land
0.227
acres
$1,800,000
0.227
acres
acres
AMAZING OPPORTUNITY to build your DREAM HOME on the prestigious Hawaii Loa Ridge. This rare rim lot features panoramic views of the Ko’olau Mountain Range, Koko Head, and the ocean. In addition, this lot has ideal topography for a builder to develop on. Hawaii Loa Ridge is a premier gated community, with 24/7 security, private park, tennis courts, club house, BBQ areas and open air pavilions!!!
Land
1.039
acres
$19,800,000
1.039
acres
acres
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.
Land
0.643
acres
$7,200,000
0.643
acres
acres
Land for sale
4775 Kahala Ave Honolulu, Oahu Neighborhood: Kahala Area
Situated in one of Oahu’s most sought-after neighborhoods, this 27,988 sq. ft. R-5-zoned lot offers the perfect canvas for a luxury residence or private family compound. Recent improvements, include level grading and CMU perimeter walls. With easy beach access, experience the serenity of Hawaii’s pristine coastline, breathtaking sunsets, and a truly exclusive island lifestyle. Ideally located just moments from the Kahala Hotel & Resort, Waialae Country Club, and Kahala Mall, this prime location offers unparalleled convenience, prestige, and tranquility. Don't miss this opportunity to create your legacy estate in this coveted community.
Land
0.290
acres
$1,699,000 ▼ $101,000
0.290
acres
acres
Huge price reduction, below tax assessed value. The Summit at Waialae Nui is a private gated community with an amazing ocean and Diamond Head view, located at the very top of Waialae Nui. It is an ideal land to build your dream home! Unit H is conveniently located by the entry gate, making your daily activities easier. Deforestation and leveling of the land is already finished. Association is being formed by Hawaiiana and it is planned to take over soon, but each home owner's association fee is still TBA. Come see visit this lot's potential, and picture the sunset views you will enjoy everyday from the comfort of your home.
Land
0.582
acres
$3,250,000 ▼ $438,888
0.582
acres
acres
The opportunity of a lifetime! Last of its kind, extremely rare and precious, intact HUGE 25,372 sq. ft. lot in Kaimuki zoned R-5, with expansive mountain, ocean, and city views - Diamond Head, Koko Head, Waikiki, Kahala, neighbor islands! Views from front, rear, and side of the lot! Tons of options for rebuilding, remodeling, expanding, dividing, and more! Make this your castle, fortress, multi-unit compound, or unique community of units. Perfectly located in Kaimuki near beaches, hikes, restaurants, shops, medical care, freeway on/off, schools, churches, parks, everything you need! Existing structures: 1) Single family home with kitchen, living room, 2 bedrooms, 3 bathrooms, & bonus rooms, on the main level, a large upstairs loft/bedroom and a large basement, 2) a 1 bed/1 bath unit, and 3) a studio unit. All square footage taken from tax record - actual measurements and #of rooms/bathrooms may differ from tax record. DON'T GO ONTO THE PROPERTY W/OUT PERMISSION - NO TRESPASSING. All items at the property shall remain there at closing except for tenant's belongings. AS IS Sale. Buyer to pay for own TIR and tenting, and do own thorough due diligence. Watch the video!