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4219 Kaikoo Pl (Diamond Head)

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4219 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
4.9 164 Google reviews
We are expert real estate agents who have sold many homes in Diamond Head. We would be happy to assist you too.
Description
An exceptional mid-century residence offering sweeping ocean views in the prestigious Diamond Head area. Designed in 1959 by acclaimed architect Vladimir Ossipoff, this home seamlessly blends clean architectural lines with a strong connection to nature. Experience island living at its finest with panoramic views of the coastline and Diamond Head.This thoughtfully designed six-bedroom, seven-and-a-half-bath estate provides direct ocean views from nearly every room, enhancing its effortless indoor-outdoor lifestyle. French-inspired bathrooms and vibrant design elements add warmth and character throughout, while glass walls maximize light and airflow. The residence is one of only twenty-four homes on Kaikoo Place.With approx. 4,109 sq. ft. of interior living space on a 7,691 sq. ft. lot, there’s ample room for entertaining or relaxing in comfort. Located moments from Kaikoo’s surf breaks, Cromwell’s, and nearby sandy beaches — and just a short drive from Waikiki, Kahala, and Downtown Honolulu — this architectural gem embodies coastal elegance and timeless design.
Recent Activity
  • Dec 01, 2025 Price ↓ $4,775,000
  • Aug 04, 2025 Listed at $5,275,000
Recent Sales
(Diamond Head)
More Details
  • Owner, Tax & Resale History
  • Price / ft²: $1,162
  • Other Homes Price / ft²
  • Cash vs Financing Buyers
  • Year Remodeled: 2024
  • Zoning: 04 - R-7.5 Residential District
  • Flood Zone: Zone X
  • Elementary School: Kahala
  • Middle School: Kaimuki
  • High School: Kalani
  • View: Coastline, Diamond Head, Garden, Mountain, Ocean, Sunrise, Sunset
  • Furnished: Partial
  • Property Condition: Average
  • Security Features: Key
  • Amenities: Bedroom on 1st Floor, Entry, Full Bath on 1st Floor, Landscaped, Maids/Guest Qrters, Other, Patio/Deck, Storage, Wall/Fence
  • TMK: 1-3-1-41-47-0
  • Tax Assessed Land: $3,007,800
  • Tax Assessed Improvements: $932,800
  • Tax Assessed Total: $3,940,600
  • Courtesy: Compass / (808) 825-4277
  • MLS: 202512547
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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 05, 2025.Information is deemed reliable but not guaranteed.
Other Diamond Head Homes
$5,299,000
Save
3857 Poka St
3 Bds | 4.5 Ba
4,508 ft²
$5,999,900
Save
4131 Black Point Pl
3 Bds | 5 Ba
2,997 ft²
$3,499,000
Save
4316 Papu Cir
4 Bds | 3 Ba
2,300 ft²
$3,490,000
Save
4305 Kaikoo Pl
4 Bds | 3 Ba
2,305 ft²
Other Honolulu Homes
Kahala
$4,700,000
Save
4745 Aukai Ave
4 Bds | 5.5 Ba
3,704 ft²
Portlock
$4,700,000
Save
532 Portlock Rd
4 Bds | 4.5 Ba
3,798 ft²
Waikiki
$4,880,000
Save
287 Wai Nani Way
Multi-Family

Kaimuki
$4,895,000
Save
3427 Waialae Ave
12 Bds | 12 Ba
8,775 ft²
Portlock
$4,988,000
Save
31 Poipu Dr
4 Bds | 4.5 Ba
3,768 ft²
Niu Beach
$4,999,000
Save
5543 Kalanianaole Hwy
3 Bds | 2.5 Ba
1,622 ft²
All Honolulu homes for sale »
  • Asking Price: $4,775,000

    $500,000 price drop 4 days ago

Description
An exceptional mid-century residence offering sweeping ocean views in the prestigious Diamond Head area. Designed in 1959 by acclaimed architect Vladimir Ossipoff, this home seamlessly blends clean architectural lines with a strong connection to nature. Experience island living at its finest with panoramic views of the coastline and Diamond Head.This thoughtfully designed six-bedroom, seven-and-a-half-bath estate provides direct ocean views from nearly every room, enhancing its effortless indoor-outdoor lifestyle. French-inspired bathrooms and vibrant design elements add warmth and character throughout, while glass walls maximize light and airflow. The residence is one of only twenty-four homes on Kaikoo Place.With approx. 4,109 sq. ft. of interior living space on a 7,691 sq. ft. lot, there’s ample room for entertaining or relaxing in comfort. Located moments from Kaikoo’s surf breaks, Cromwell’s, and nearby sandy beaches — and just a short drive from Waikiki, Kahala, and Downtown Honolulu — this architectural gem embodies coastal elegance and timeless design.
    The MLS properties are based on information from the Multiple Listing Service of Hicentral MLS, Ltd. Listings last updated on December 05, 2025.Information is deemed reliable but not guaranteed.
    • Dec 01, 2025 Price ↓ $4,775,000
    • Aug 04, 2025 Listed at $5,275,000
    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
    $5,299,000
    Save
    3857 Poka St
    3 Bds | 4.5 Ba
    4,508 ft²
    $5,999,900
    Save
    4131 Black Point Pl
    3 Bds | 5 Ba
    2,997 ft²
    $3,499,000
    Save
    4316 Papu Cir
    4 Bds | 3 Ba
    2,300 ft²
    $3,490,000
    Save
    4305 Kaikoo Pl
    4 Bds | 3 Ba
    2,305 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.