Hawaii Living

4221 Kaikoo Pl (Diamond Head)

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Photo 1 of 4221 Kaikoo Pl, Honolulu
4221 Kaikoo Pl, Honolulu
Selling or Buying in Diamond Head?
Call/Text Tracy (808) 372-2274 or send a message using the form below.
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
Description
Magnificent panoramic views from this Seaview home overlooking Diamond Head and the azure ocean from every room! Situated on one of the island's most prestigious streets and sought after neighborhoods, this home is close to the sandy beach for swimming and the famous surfing spots of Brown's, Kaikoo's, and Cromwell's. Offering an elegant casual ambiance with a beachy modern vibe, this indoor/outdoor island home is inviting for relaxation or entertainment. Featuring two Primary Bedrooms on different floors, one with a Den, and each with an En-Suite Bathroom, there is also a third Guest Room/Den, and all open to a lanai. The Living room, Family room and Dining areas feature cathedral ceilings and generous spaces for entertaining and access the incredible ocean-facing covered deck with 180-degree views. The dining room features walls of windows to capture the emerald tropical greenery beyond and the refreshing cross breeze. Enjoy the "Endless Pool" with resistance jets for swimming against a current or for a refreshing dip. This residence come complete with a gas-powered generator and 2 car garage. This is your opportunity to own a home in Diamond Head. Enjoy the island lifestyle!
Past Activity
  • Mar 15, 2023 Sold for $3,300,000
  • Feb 17, 2023 Under Contract
  • Dec 13, 2022 Price $3,600,000
  • Nov 17, 2022 Listed at $4,000,000
More Details
  • Owner, Tax & Resale History
  • Price / ft²: $1,241
  • Other Homes Price / ft²
  • Cash vs Financing Buyers
  • Year Remodeled: 1989
  • Zoning: 04 - R-7.5 Residential District
  • Flood Zone: Zone X
  • View: Coastline, Diamond Head, Garden, Ocean
  • Property Condition: Excellent,Above Average
  • Security Features: Key, Video
  • Amenities: Entry, Patio/Deck, Wall/Fence
  • TMK: 1-3-1-41-46-0
  • Tax Assessed Land: $2,479,100
  • Tax Assessed Improvements: $172,500
  • Tax Assessed Total: $2,651,600
  • Courtesy: Coldwell Banker Realty / (808) 732-1414
  • MLS: 202223874
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 27, 2025.Information is deemed reliable but not guaranteed.
Other Diamond Head Homes
$3,330,000
4316 Papu Cir
4 Bds | 3 Ba
2,300 ft²
$3,300,000
3025 Diamond Head Rd
2 Bds | 2 Ba
1,378 ft²
$3,259,000
4305 Kaikoo Pl
4 Bds | 3 Ba
2,305 ft²
$4,775,000
4219 Kaikoo Pl
6 Bds | 7.5 Ba
4,109 ft²
Other Honolulu Homes
Kalihi
$3,600,000
1611 Kahai St
Multi-Family

Waialae Nui
$3,600,000
1947 Alaeloa St
7 Bds | 5 Ba
3,592 ft²
Hawaii Loa Ridge
$3,588,888
97 Moaniala Pl
5 Bds | 5 Ba
3,677 ft²
Manoa
$3,580,000
2626 Hillside Ave
8 Bds | 8 Ba
5,749 ft²
Wilhelmina Rise
$3,550,000
3865 Mariposa Dr
6 Bds | 5 Ba
3,864 ft²
Paiko Lagoon
$3,680,000
218 Paiko Dr
5 Bds | 2 Ba
1,636 ft²
  • Sold 3/15/23 at $3,300,000
    (List Price: $3,600,000)
Description
Magnificent panoramic views from this Seaview home overlooking Diamond Head and the azure ocean from every room! Situated on one of the island's most prestigious streets and sought after neighborhoods, this home is close to the sandy beach for swimming and the famous surfing spots of Brown's, Kaikoo's, and Cromwell's. Offering an elegant casual ambiance with a beachy modern vibe, this indoor/outdoor island home is inviting for relaxation or entertainment. Featuring two Primary Bedrooms on different floors, one with a Den, and each with an En-Suite Bathroom, there is also a third Guest Room/Den, and all open to a lanai. The Living room, Family room and Dining areas feature cathedral ceilings and generous spaces for entertaining and access the incredible ocean-facing covered deck with 180-degree views. The dining room features walls of windows to capture the emerald tropical greenery beyond and the refreshing cross breeze. Enjoy the "Endless Pool" with resistance jets for swimming against a current or for a refreshing dip. This residence come complete with a gas-powered generator and 2 car garage. This is your opportunity to own a home in Diamond Head. Enjoy the island lifestyle!
    The MLS properties are based on information from the Multiple Listing Service of Hicentral MLS, Ltd. Listings last updated on December 27, 2025.Information is deemed reliable but not guaranteed.
    • Mar 15, 2023 Sold for $3,300,000
    • Feb 17, 2023 Under Contract
    • Dec 13, 2022 Price $3,600,000
    • Nov 17, 2022 Listed at $4,000,000
    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
    $3,330,000
    4316 Papu Cir
    4 Bds | 3 Ba
    2,300 ft²
    $3,300,000
    3025 Diamond Head Rd
    2 Bds | 2 Ba
    1,378 ft²
    $3,259,000
    4305 Kaikoo Pl
    4 Bds | 3 Ba
    2,305 ft²
    $4,775,000
    4219 Kaikoo Pl
    6 Bds | 7.5 Ba
    4,109 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.