As 2026 begins, Oahu’s luxury real estate market continues to set the bar for ultra-high-end living in Hawaii. Limited inventory, irreplaceable oceanfront land, and legacy estates in premier neighborhoods have pushed prices to historic levels—particularly along Diamond Head and Kahala.
Oahu Luxury Real Estate Market at the Start of 2026
Below are the five most expensive homes currently for sale on Oahu, showcasing the pinnacle of luxury, privacy and location.
#1 Most Expensive Home for Sale on Oahu: Hooluana Estate
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Oceanfront Estate on Diamond Head Road
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Legacy Property with Development Potential
3735 Diamond Head Road | $55,000,000
At the top of the market is Hooluana Estate, one of Honolulu’s last remaining legacy, estate-sized properties. Spanning more than two acres across two adjacent parcels, this 3735 Diamond Head Road offering includes two residences and an open lot totaling nearly 89,000 square feet of land. With sweeping ocean views, beachfront access, and R-7.5 zoning, the estate offers exceptional flexibility for preservation or future development. Ideally located between Kahala and Waikiki, Hooluana Estate represents a once-in-a-generation opportunity in one of Hawaii’s most prestigious coastal corridors.
MLS#202520629 | 3735 Diamond Head Road, Honolulu 96816 is listed Courtesy of Hawaii Life (800) 667-5028
#2 Oceanfront Estate for Sale in Kahala
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Luxury Home on Kahala Avenue
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Single-Level Oceanfront Living
4505 Kahala Avenue | $45,000,000
This newly reimagined oceanfront estate at 4505 Kahala Avenue spans 1.3 acres from street to sea, featuring 171 linear feet of ocean frontage. Designed as a single-level residence, nearly 10,000 square feet of interior living space flows seamlessly to expansive outdoor lanais through walls of floor-to-ceiling glass. A 5,000-square-foot oceanfront lanai, resort-style pool and spa, and refined contemporary finishes make this home a standout in one of Oahu’s most exclusive neighborhoods.
MLS#202506837 | 4505 Kahala Avenue, Honolulu 96816 is listed Courtesy of Coldwell Banker Realty (808) 596-0456
#3 Diamond Head Oceanfront Estate with Beach Access
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Adjacent Parcel to Hooluana Estate
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Rare Large-Land Offering on Oahu
3735 Diamond Head Road (Parcel A) | $43,000,000
Offered separately, this adjacent Diamond Head Road parcel is part of the greater Hooluana Estate opportunity. Encompassing approximately 80,000 square feet, the property includes an expansive residence, open lots, sweeping ocean views, and private or deeded beachfront access. Available individually or alongside the $55 million offering, this parcel provides rare scale and long-term value in a location where comparable opportunities simply no longer exist.
MLS#202520630 | 3735 Diamond Head Road (Parcel A), Honolulu 96816 is listed Courtesy of Hawaii Life (800) 667-5028
#4 The Hemmeter Estate on Black Point
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Iconic Oceanfront Estate in Hawaii
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Architecturally Significant Luxury Home
4324 Kaikoo Place | $37,500,000
Situated at the end of Kaikoo Place on Black Point, in the Kahala nieghborhood, 4324 Kaikoo Place (also known as The Hemmeter Estate) boasts an extraordinary 339 linear feet of ocean frontage—making it one of the most significant oceanfront properties in Hawaii. With more than 21,000 square feet of interior living space, the estate blends European Renaissance inspiration with Hawaiian natural elements. Highlights include a two-story oceanfront living room, Italian marble staircases, private theater, grotto-style pool, and a nearly 5,000-square-foot primary suite. This is a truly irreplaceable estate defined by scale, privacy, and architectural significance.
MLS#202528159 | 4324 Kaikoo Place, Honolulu 96816 is listed Courtesy of Compass (808) 825-4277
#5 Diamond Head Estate with Botanical Gardens
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Luxury Home Near Waikiki
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Legacy Estate with Panoramic Ocean Views
2955 Makalei Place | $34,000,000
This rare Diamond Head estate at 2955 Makalei Place reflects decades of thoughtful ownership, meticulous care, and timeless design. Set on more than 34,000 square feet of land, the residence offers panoramic ocean and coastal views just minutes from Waikiki. Beyond the home itself, the property’s botanical garden setting—complete with fountains, arbors, terraces, and winding paths—creates a private oasis unlike any other. A guest cottage and pilates studio further enhance this refined legacy property.
MLS#202523993 | 2955 Makalei Place, Honolulu 96815 is listed Courtesy of Compass (808) 825-4277
Explore Luxury Homes for Sale on Oahu
Looking for more exclusive opportunities? Explore more luxury homes for sale on Oahu or connect with a Locations agent for private showings and market insight.
