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3735- Diamond Head Rd (Diamond Head)

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3735- Diamond Head Rd, Honolulu
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Tracy Yamato

Tracy Yamato

Certified Residential Specialist
Realtor, RS-51972

Mobile: (808) 372-2274

Email: Tracy@HawaiiLiving.com

"Let my over 33 years of experience work for you."
Client Testimonials
We are expert real estate agents who have sold many homes in Diamond Head. We would be happy to assist you too.
Description
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.
Recent Activity
  • Oct 02, 2025 Listed at $43,000,000
  • Oct 02, 2025 Off Market
  • Mar 17, 2025 Listed at $43,000,000
Recent Sales
(Diamond Head)
More Details
  • Owner, Tax & Resale History
  • Price / ft²: $6,921
  • Other Homes Price / ft²
  • Cash vs Financing Buyers
  • Zoning: 04 - R-7.5 Residential District
  • Flood Zone: Zone X
  • View: Coastline, Diamond Head, Garden, Mountain, Ocean
  • Furnished: None
  • Property Condition: Average
  • Amenities: Bedroom on 1st Floor, Entry, Full Bath on 1st Floor, Landscaped, Maids/Guest Qrters, Patio/Deck, Wall/Fence, Workshop
  • TMK: 1-3-1-39-5-0
  • Tax Assessed Land: $9,351,700
  • Tax Assessed Improvements: $1,174,100
  • Tax Assessed Total: $10,525,800
  • Courtesy: Hawaii Life / (800) 667-5028
  • MLS: 202520630
Ask Tracy a Question
About Diamond Head
Come where Royalty spent their days of pleasure. The 650 or so exclusive Diamond Head homes represent some of the finest, most sought after real estate in Honolulu. Just south of Waikiki past the Honolulu Zoo, the Diamond Head neighborhood wraps around Diamond Head Crater and includes the Gold Coast along Kalakaua Ave and Kapiolani Park.

Further circled by Monsarrat Ave and Diamond Head Rd, it also includes Fort Ruger Park - aka Triangle Park - and some of the surrounding streets such as Kaimanahila, Hakaka as well as Papu Circle and Kaikoo Pl. See this brief video flying over the Diamond H

  ... Read more
The MLS properties are based on information from the Multiple Listing Service of Hicentral MLS, Ltd. Listings last updated on December 26, 2025.Information is deemed reliable but not guaranteed.
Other Diamond Head Homes
$37,500,000
4324 Kaikoo Pl
5 Bds | 9 Ba
21,266 ft²
$34,000,000
2955 Makalei Pl
4 Bds | 9 Ba
5,226 ft²
$55,000,000
3735 Diamond Head Rd
11 Bds | 10.5 Ba
10,047 ft²
$26,500,000
213 Kaalawai Pl
5 Bds | 7.5 Ba
7,324 ft²
Other Hawaii Homes
Kahala
$45,000,000
4505 Kahala Ave
6 Bds | 8 Ba
9,896 ft²
Kailua Beachside
$50,000,000
508 N Kalaheo Ave
12 Bds | 15 Ba
12,005 ft²
Waimea (Kamuela)
$47,000,000
68-1023 Pauoa Way
7 Bds | 11 Ba
7,874 ft²
Kona
$49,000,000
75-5530 Kona Bay Dr
10 Bds | 13 Ba
12,528 ft²
Hana
$35,000,000
5670 Hana Hwy
2 Bds | 2 Ba
1,828 ft²
Wailea
$33,000,000
7505 Makena Rd
7 Bds | 8 Ba
10,500 ft²
  • Asking Price: $43,000,000
Description
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.
    The MLS properties are based on information from the Multiple Listing Service of Hicentral MLS, Ltd. Listings last updated on December 26, 2025.Information is deemed reliable but not guaranteed.
    • Oct 02, 2025 Listed at $43,000,000
    • Oct 02, 2025 Off Market
    • Mar 17, 2025 Listed at $43,000,000
    Come where Royalty spent their days of pleasure. The 650 or so exclusive Diamond Head homes represent some of the finest, most sought after real estate in Honolulu. Just south of Waikiki past the Honolulu Zoo, the Diamond Head neighborhood wraps around Diamond Head Crater and includes the Gold Coast along Kalakaua Ave and Kapiolani Park.

    Further circled by Monsarrat Ave and Diamond Head Rd, it also includes Fort Ruger Park - aka Triangle Park - and some of the surrounding streets such as Kaimanahila, Hakaka as well as Papu Circle and Kaikoo Pl. See this brief video flying over the Diamond H

      ... Read more
    Other Diamond Head Homes
    $37,500,000
    4324 Kaikoo Pl
    5 Bds | 9 Ba
    21,266 ft²
    $34,000,000
    2955 Makalei Pl
    4 Bds | 9 Ba
    5,226 ft²
    $55,000,000
    3735 Diamond Head Rd
    11 Bds | 10.5 Ba
    10,047 ft²
    $26,500,000
    213 Kaalawai Pl
    5 Bds | 7.5 Ba
    7,324 ft²
    You do not own the land, but have the right to use the land until an expiration year. At expiration the ownership typically reverts back to the land owner.
    Buyer and Seller have reached an agreement and are under contract. The sale may be subject to one or more contingencies.
    We have handled many transactions for clients who purchase Hawaii real estate without visiting. By request, we can prepare thorough property videos to ensure you are familiar with every detail necessary. All documents can be signed remotely.
    Buyer and Seller have reached an agreement and are under contract. The sale is expected to close / record soon.
    We will be happy to work with you as a Buyer's agent. Call us to learn more: 808-943-9000.
    Note: A Seller's agent has a fiduciary responsibility towards the Seller. Working with a Buyer's agent objectives and goals are aligned, at no cost to you, the Buyer.
    Other fees could be a special assessment, reserve contributions etc.
    DOM = Days On Market. Our site shows listings immediately. A brand new listing may show DOM 2 or 3 days, if listing agent did not upload the same day listing agreement was executed.
    Includes estimated monthly mortgage payment, maintenance / HOA fees & property taxes. The estimate does not include insurance premiums.
    Learn about property tax rates.