Hawaii Living

4240 Kaikoo Pl (Diamond Head)

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4240 Kaikoo Pl, 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
A rare opportunity to own one of Diamond Head's most captivating oceanfront estates at a newly reduced rate; truly the best value Diamond Head. This Balinese-inspired masterpiece blends timeless island elegance with modern sophistication. Designed to embrace Hawaii's indoor-outdoor lifestyle, the residence opens seamlessly to panoramic ocean vistas and the rhythmic sound of the waves. This five-bedroom sanctuary showcases bespoke finishes, natural textures, and an architectural flow that evokes both serenity and grandeur. The primary suite offers breathtaking ocean views and a spa-like en-suite retreat, while a private guest apartment-complete with its own entrance-provides stunning views of Diamond Head and total privacy for family or guests. Outdoors, a private tropical oasis awaits. Surrounded by lush landscaping, the grounds feature a resort-style pool, elevated spa, fire pit, and tranquil koi pond, creating an atmosphere of peaceful indulgence. Gated and secure, yet minutes from Waikiki Beach and Diamond Head State Monument, this rare offering perfectly balances luxury, seclusion and convenience. it is the premier value in Diamond Head's pristine oceanfront enclave.
Recent Activity
  • Dec 31, 2025 Price $5,999,000
  • Dec 31, 2025 Listed at $5,099,000
  • Dec 31, 2025 Off Market
  • Nov 06, 2025 Price $6,250,000
  • Oct 16, 2025 Price $6,698,000
  • Sep 11, 2025 Price $6,725,000
  • Jul 31, 2025 Price $6,750,000
  • Jun 11, 2025 Price $6,850,000
  • Apr 22, 2025 Price $6,999,000
  • Mar 13, 2025 Price $7,299,000
  • Dec 06, 2024 Price $7,498,000
  • Oct 25, 2024 Listed at $7,899,000
  • May 28, 2024 Off Market
  • Apr 26, 2024 Back to Active
  • Mar 25, 2024 Under Contract
  • Feb 12, 2024 Price $6,695,000
  • Jan 13, 2024 Price $6,950,000
  • Dec 05, 2023 Price $7,250,000
  • Nov 01, 2023 Price $7,995,000
  • Oct 05, 2023 Price $8,250,000
  • Sep 05, 2023 Price $9,000,000
  • Jul 24, 2023 Listed at $9,850,000
  • Jul 21, 2023 Off Market
  • May 09, 2023 Price $8,750,000
  • Apr 03, 2023 Listed at $9,995,000
  • Oct 14, 2022 Off Market
  • Aug 05, 2022 Off Market
  • Mar 05, 2022 Listed at $7,995,000
  • Mar 05, 2022 Off Market
  • Feb 10, 2022 Price $7,995,000
  • Nov 30, 2021 Price $7,500,000
  • Oct 05, 2021 Price $7,950,000
  • Sep 04, 2021 Price $8,750,000
  • Mar 05, 2021 Listed at $8,990,000
  • Oct 17, 2020 Off Market
  • May 14, 2020 Off Market
  • Jan 23, 2020 Price $8,500,000
  • Oct 18, 2019 Listed at $9,990,000
  • Oct 03, 2019 Off Market
  • Jul 01, 2019 Price $12,800,000
  • Mar 29, 2019 Listed at $14,800,000
  • Feb 21, 2019 Off Market
  • Jun 18, 2018 Off Market
  • Feb 22, 2018 Listed at $10,900,000
  • Apr 18, 2016 Sold for $5,250,000
  • Mar 18, 2016 Under Contract
  • Jan 11, 2016 Listed at $5,500,000
Recent Sales
(Diamond Head)
More Details
  • Owner, Tax & Resale History
  • Price / ft²: $1,159
  • Other Homes Price / ft²
  • Cash vs Financing Buyers
  • Year Remodeled: 2025
  • Zoning: 04 - R-7.5 Residential District
  • Flood Zone: Zone VE
  • View: Diamond Head, Ocean, Sunset
  • Property Condition: Excellent
  • Security Features: Key, Video
  • Amenities: Bedroom on 1st Floor, Entry, Full Bath on 1st Floor, Landscaped, Maids/Guest Qrters, Patio/Deck, Storage, Wall/Fence, Workshop
  • TMK: 1-3-1-41-21-0
  • Tax Assessed Land: $5,717,300
  • Tax Assessed Improvements: $571,100
  • Tax Assessed Total: $6,288,400
  • Courtesy: Coldwell Banker Realty / (808) 738-3904
  • MLS: 202528401
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 January 11, 2026.Information is deemed reliable but not guaranteed.
Other Diamond Head Homes
$5,999,900
4131 Black Point Pl
3 Bds | 5 Ba
2,997 ft²
$6,380,000
4218 Kaimanahila St
4 Bds | 5.5 Ba
4,832 ft²
$4,775,000
4219 Kaikoo Pl
6 Bds | 7.5 Ba
4,109 ft²
$7,680,000
3124 Noela Dr
5 Bds | 7 Ba
7,953 ft²
Other Honolulu Homes
Napali Haweo
$5,870,000
123 Waihili Pl
5 Bds | 5.5 Ba
5,082 ft²
Dowsett
$6,400,000
18 Homelani Pl
4 Bds | 4.5 Ba
4,825 ft²
Kahala
$5,250,000
4536 Kolohala St
6 Bds | 5.5 Ba
4,757 ft²
Kahala
$6,884,000
4363 Kilauea Ave
4 Bds | 4 Ba
3,860 ft²
Kapiolani
$6,888,000
Kapahulu
$5,100,000
2848 Date St
Multi-Family

  • Asking Price: $5,999,000
Description
A rare opportunity to own one of Diamond Head's most captivating oceanfront estates at a newly reduced rate; truly the best value Diamond Head. This Balinese-inspired masterpiece blends timeless island elegance with modern sophistication. Designed to embrace Hawaii's indoor-outdoor lifestyle, the residence opens seamlessly to panoramic ocean vistas and the rhythmic sound of the waves. This five-bedroom sanctuary showcases bespoke finishes, natural textures, and an architectural flow that evokes both serenity and grandeur. The primary suite offers breathtaking ocean views and a spa-like en-suite retreat, while a private guest apartment-complete with its own entrance-provides stunning views of Diamond Head and total privacy for family or guests. Outdoors, a private tropical oasis awaits. Surrounded by lush landscaping, the grounds feature a resort-style pool, elevated spa, fire pit, and tranquil koi pond, creating an atmosphere of peaceful indulgence. Gated and secure, yet minutes from Waikiki Beach and Diamond Head State Monument, this rare offering perfectly balances luxury, seclusion and convenience. it is the premier value in Diamond Head's pristine oceanfront enclave.
    The MLS properties are based on information from the Multiple Listing Service of Hicentral MLS, Ltd. Listings last updated on January 11, 2026.Information is deemed reliable but not guaranteed.
    • Dec 31, 2025 Price $5,999,000
    • Dec 31, 2025 Listed at $5,099,000
    • Dec 31, 2025 Off Market
    • Nov 06, 2025 Price $6,250,000
    • Oct 16, 2025 Price $6,698,000
    • Sep 11, 2025 Price $6,725,000
    • Jul 31, 2025 Price $6,750,000
    • Jun 11, 2025 Price $6,850,000
    • Apr 22, 2025 Price $6,999,000
    • Mar 13, 2025 Price $7,299,000
    • Dec 06, 2024 Price $7,498,000
    • Oct 25, 2024 Listed at $7,899,000
    • May 28, 2024 Off Market
    • Apr 26, 2024 Back to Active
    • Mar 25, 2024 Under Contract
    • Feb 12, 2024 Price $6,695,000
    • Jan 13, 2024 Price $6,950,000
    • Dec 05, 2023 Price $7,250,000
    • Nov 01, 2023 Price $7,995,000
    • Oct 05, 2023 Price $8,250,000
    • Sep 05, 2023 Price $9,000,000
    • Jul 24, 2023 Listed at $9,850,000
    • Jul 21, 2023 Off Market
    • May 09, 2023 Price $8,750,000
    • Apr 03, 2023 Listed at $9,995,000
    • Oct 14, 2022 Off Market
    • Aug 05, 2022 Off Market
    • Mar 05, 2022 Listed at $7,995,000
    • Mar 05, 2022 Off Market
    • Feb 10, 2022 Price $7,995,000
    • Nov 30, 2021 Price $7,500,000
    • Oct 05, 2021 Price $7,950,000
    • Sep 04, 2021 Price $8,750,000
    • Mar 05, 2021 Listed at $8,990,000
    • Oct 17, 2020 Off Market
    • May 14, 2020 Off Market
    • Jan 23, 2020 Price $8,500,000
    • Oct 18, 2019 Listed at $9,990,000
    • Oct 03, 2019 Off Market
    • Jul 01, 2019 Price $12,800,000
    • Mar 29, 2019 Listed at $14,800,000
    • Feb 21, 2019 Off Market
    • Jun 18, 2018 Off Market
    • Feb 22, 2018 Listed at $10,900,000
    • Apr 18, 2016 Sold for $5,250,000
    • Mar 18, 2016 Under Contract
    • Jan 11, 2016 Listed at $5,500,000
    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
    $5,999,900
    4131 Black Point Pl
    3 Bds | 5 Ba
    2,997 ft²
    $6,380,000
    4218 Kaimanahila St
    4 Bds | 5.5 Ba
    4,832 ft²
    $4,775,000
    4219 Kaikoo Pl
    6 Bds | 7.5 Ba
    4,109 ft²
    $7,680,000
    3124 Noela Dr
    5 Bds | 7 Ba
    7,953 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.