Four Properties Worth Knowing About: An Honest Look
These four properties represent some of the most significant listings on Oahu right now. Different locations, different personalities, different buyers. Here's a straightforward breakdown of what each one offers — and what kind of life it actually asks of you.
01 — LIHIWAI Estate, Nuuanu
51 Kepola Place, Honolulu | $22,000,000 | MLS #202606611 6 bed / 9 bath | 24,899 sq ft | 1.81 acres | Built 1927–1929
The History
LIHIWAI was originally built for Territorial Governor George R. Carter between 1927 and 1929. The architect was Bertram Grosvenor Goodhue — the same architect behind St. Thomas Church in New York and the Nebraska State Capitol. It is, in the most literal sense, a piece of Hawaii's political and architectural history. The estate has recently undergone a museum-quality restoration by Welch & Weeks using original materials: ohia hardwood, old-growth redwood, bronze windows, and limestone.
What You Get
A legacy property that has been fully restored and genuinely cannot be replicated. Nearly two acres in Nuuanu Valley with a natural stream, auwai, dramatic waterfall, and heated saltwater pool and spa. A main residence plus two guest homes. The scale here — nearly 25,000 square feet — is essentially unheard of in a single-family home on Oahu.
This is for the buyer who: Wants ownership of something that matters historically. People who buy LIHIWAI aren't buying square footage — they're buying stewardship of a landmark.
Worth Knowing
Nuuanu sits inland, in the mist. It is quieter and cooler than the coastal neighborhoods — which for the right buyer is the entire point. It's not a beach-access property. And a 95-year-old restored estate, however beautifully maintained, will have a different relationship with upkeep than new construction. The scale demands it.
The lifestyle here is private, green, and genuinely removed from the energy of the rest of the island. If you want a home that announces itself the moment you arrive — this is it.
02 — North Shore Club Penthouse, Turtle Bay
57-275 Kamehameha Hwy Unit 3/15, Kahuku | $20,000,000 | MLS #202600680 6 bed / 7 bath | 6,029 sq ft interior + 1,321 sq ft lanai | New Construction (est. completion 2027)
The History
The North Shore Club is part of the broader Turtle Bay master-planned community, developed by Areté Collective on land adjacent to over 500 acres of protected conservation land near Kahuku Point. The Ritz-Carlton Oahu at Turtle Bay recently opened nearby. This is Phase I of a new residential development — 20 total residences — and this is the final beachfront penthouse available.
What You Get
Direct beachfront, new construction, private pool, floor-to-ceiling ocean views across Oahu's legendary North Shore. Pre-construction design selections are still available, meaning the buyer can personalize finishes. Access to championship golf, resort pools, spa, fitness, and curated dining within the development. The architecture is contemporary coastal — clean, intentional, indoor-outdoor.
This is for the buyer who: Wants the North Shore lifestyle without sacrificing the amenities. A second home buyer or someone making a genuine lifestyle pivot who is comfortable with a longer commute to urban Honolulu.
Worth Knowing
This is a pre-construction purchase with an estimated 2027 completion. The North Shore is roughly 40 miles from central Honolulu — beautiful in every direction, but a real consideration for anyone with frequent city obligations. The community is members-only and resort-integrated, which is a draw for some buyers and a different kind of lifestyle than the island's more private residential enclaves. The Flood Zone VE designation (direct coastal exposure) is standard for beachfront properties and worth factoring into insurance planning.
The pace of life here is fundamentally different from town. That's the draw — and the daily reality.
03 — The Mokulua Estate, Lanikai
1240 Mokulua Drive, Kailua | $31,000,000 | MLS #202600075 9 bed / 10 bath | 10,326 sq ft | Direct beachfront, Lanikai
The History
1240 Mokulua Drive sits on one of the most coveted stretches of Lanikai Beach — a neighborhood that has been attracting discerning buyers for decades precisely because it doesn't try to be anything other than what it is. Lanikai's serenity, its offshore Mokulua Islands views, and its consistently ranked-best-beach shoreline have made properties here some of the hardest to acquire on Oahu. This estate was built to honor that setting: unobstructed Mokulua Island views, sustainable features including 34 PV panels, Tesla Powerwalls, and an EV charger, and custom interior details including Koa doors and an elevator.
What You Get
Direct beachfront in Lanikai. Nine bedrooms across 10,000+ square feet. The Mokulua Islands as your permanent view — a sight that doesn't get old. This is a compound-level property suitable for multi-generational living, extended family, or a principal residence with serious guest capacity. The scale and the address together represent one of the rarest offerings on Oahu.
This is for the buyer who: Wants the best beach on the island and is prepared to pay for permanence. There is no equivalent address.
Worth Knowing
Lanikai is one of the most in-demand and least-available neighborhoods on Oahu — which cuts both ways. There is very little inventory here ever, which supports long-term value but also means the neighborhood doesn't move quickly. Properties of this scale and price point take time to find their buyer, and that's by design. Flood insurance and coastal maintenance are inherent to direct beachfront ownership anywhere in Hawaii. The buyer who appreciates this property understands that; it's part of the equation, not a surprise.
This is a generational purchase. The kind of thing you don't sell.
04 — Diamond Head Estate, Makalei Place
2955 Makalei Place, Honolulu | $34,000,000 | MLS #202523993 4 bed / 9 bath | 5,226 sq ft | 34,157 sq ft lot (0.78 acres) | Built 1941, renovated 2005–2006
The History
Built in 1941, this estate has been under the same ownership for the better part of two decades — last sold in 2007 for $7.55 million. The renovation completed in 2005–2006 honored the original architecture while introducing modern systems and finishes. The gardens were designed with a specific intention: an oasis, structured around water features, arbors, terraces, and a winding path — a considered composition rather than incidental landscaping. The setting within the Diamond Head neighborhood places it among Oahu's most consistently prestigious addresses.
What You Get
Nearly three-quarters of an acre at Diamond Head — that acreage alone is notable in this location. Ocean and coastal views. Custom woodwork, curated interiors, an infinity pool, central air, and a separate studio cottage with its own entrance off Diamond Head Road. Walking distance to Waikiki's resort amenities, five minutes to Kahala, ten minutes to the airport. The gardens here are a genuine differentiator — the kind of mature botanical composition that takes decades to achieve and can't be rushed.
This is for the buyer who: Wants Diamond Head prestige, meaningful land, serious privacy, and proximity to everything — without being in the thick of it.
Worth Knowing
This property is priced at $34M on a home that was assessed at significantly less and last transacted at $7.55M in 2007. The ask reflects the land, the location, and the vision the current owners have for the asset — which a buyer will need to share. At 5,226 square feet, the interior is intimate relative to the acreage and price; the value here is overwhelmingly in the land and address rather than the structure itself. For a buyer looking for a large-square-footage home, there are other options at Diamond Head. For a buyer who understands that a 34,000-square-foot lot at the base of Diamond Head crater is irreplaceable — this reads differently.
The gardens, the lot, and the address are the inheritance. The house is where you sleep.
Want to walk any of these? I'm happy to connect you with the right conversation.