Hawaii Living

269 Kailua Rd (Kailua Estates)

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Photo 1 of 269 Kailua Rd, Kailua
269 Kailua Rd, Kailua
Selling or Buying in Kailua Estates?
Description
Situated in Kailua Estates, this 5 bedroom 3 bath Hawaiian style home has separate living and garden areas perfect for multi-generational living or investor. Excellent position on the path to Kailua Beach and Kailua town to enjoy ocean sports or shopping and restaurants. The original 3/1 was recently remodeled and 2/2 addition was newly built in 2011. Home boasts underground utilities, owned Net Metering PV, solar water heater, outdoor showers, storage shed, and a lovely covered lanai. Relaxed outdoor living with lush tropical landscaping for your pleasure.
Past Activity
  • Sep 23, 2025 Sold for $2,250,000
  • Aug 25, 2025 Under Contract
  • Aug 01, 2025 Listed at $2,388,000
  • Aug 01, 2025 Off Market
  • Apr 25, 2025 Listed at $2,498,000
  • Sep 15, 2022 Off Market
  • Sep 15, 2022 Off Market
  • Sep 05, 2022 Listed at $2,375,000
  • Nov 16, 2018 Sold for $1,850,000
  • Oct 11, 2018 Under Contract
  • Aug 29, 2018 Listed at $1,950,000
More Details
  • Owner, Tax & Resale History
  • Price / ft²: $896
  • Year Remodeled: 2011
  • Zoning: 03 - R10 - Residential District
  • Flood Zone: Zone X
  • Elementary School: Kailua
  • Middle School: Kailua
  • High School: Kalaheo
  • View: Garden
  • Furnished: Full
  • Property Condition: Excellent
  • Amenities: Bedroom on 1st Floor, Full Bath on 1st Floor, Landscaped, Patio/Deck, Storage, Wall/Fence
  • TMK: 1-4-2-20-84-0
  • Tax Assessed Land: $1,080,000
  • Tax Assessed Improvements: $337,900
  • Tax Assessed Total: $1,417,900
  • Courtesy: Coldwell Banker Pacific Prop.
  • MLS: 201822425
About Kailua Estates
See this aerial video of Kailua Estate homes.

Kailua Estates could be called one of the old kamaaina communities, a label justified by the vintage houses dating from the 1940s and 50s that stand proudly here still. When the first owners moved in, Kailua was a small beachside town, isolated – some would say 'protected' - from Honolulu by the Koolaus in that pre-Pali Tunnel era.

Bordered on the south side by the Enchanted Lake canal, the easiest way to pinpoint this community's location is to stand in front of the Plantation store facade of Kalapawai Market, right at Kailua Beach Par  ... Read more
The MLS properties are based on information from the Multiple Listing Service of Hicentral MLS, Ltd. Listings last updated on December 30, 2025.Information is deemed reliable but not guaranteed.
Other Kailua Estates Homes
$2,499,000
409 Wanaao Rd
4 Bds | 3.5 Ba
2,483 ft²
Other Oahu Homes
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Keolu Hills
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Kalama Tract & Coconut Grove
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Enchanted Lake
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889 Akumu St
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Kaopa
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Alewa Heights & Kam Heights
$1,950,000
1313 Ahiahi St
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  • Sold 11/16/18 at $1,850,000
    (List Price: $1,950,000)
Description
Situated in Kailua Estates, this 5 bedroom 3 bath Hawaiian style home has separate living and garden areas perfect for multi-generational living or investor. Excellent position on the path to Kailua Beach and Kailua town to enjoy ocean sports or shopping and restaurants. The original 3/1 was recently remodeled and 2/2 addition was newly built in 2011. Home boasts underground utilities, owned Net Metering PV, solar water heater, outdoor showers, storage shed, and a lovely covered lanai. Relaxed outdoor living with lush tropical landscaping for your pleasure.
    The MLS properties are based on information from the Multiple Listing Service of Hicentral MLS, Ltd. Listings last updated on December 30, 2025.Information is deemed reliable but not guaranteed.
    • Sep 23, 2025 Sold for $2,250,000
    • Aug 25, 2025 Under Contract
    • Aug 01, 2025 Listed at $2,388,000
    • Aug 01, 2025 Off Market
    • Apr 25, 2025 Listed at $2,498,000
    • Sep 15, 2022 Off Market
    • Sep 15, 2022 Off Market
    • Sep 05, 2022 Listed at $2,375,000
    • Nov 16, 2018 Sold for $1,850,000
    • Oct 11, 2018 Under Contract
    • Aug 29, 2018 Listed at $1,950,000
    See this aerial video of Kailua Estate homes.

    Kailua Estates could be called one of the old kamaaina communities, a label justified by the vintage houses dating from the 1940s and 50s that stand proudly here still. When the first owners moved in, Kailua was a small beachside town, isolated – some would say 'protected' - from Honolulu by the Koolaus in that pre-Pali Tunnel era.

    Bordered on the south side by the Enchanted Lake canal, the easiest way to pinpoint this community's location is to stand in front of the Plantation store facade of Kalapawai Market, right at Kailua Beach Par  ... Read more
    Other Kailua Estates Homes
    $2,499,000
    409 Wanaao Rd
    4 Bds | 3.5 Ba
    2,483 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.
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