Hawaii Living

1255 Aupupu Pl (Hillcrest Kailua)

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Photo 1 of 1255 Aupupu Pl, Kailua
1255 Aupupu Pl, Kailua
Selling or Buying in Hillcrest Kailua?
Description
Open on Saturday 10/16 and Sunday 10/17 from 2-5 PM each day. Seller requests highest & best offers by 10:00 AM on Tuesday 10/19. Breathtaking views from every level. This beautiful home is perched on the most desired side of Hill Crest with picture windows that frame Kailua bay, Lanikai Mountain and Bellows. The home encompasses 3 large bedrooms and 2 large lanai's, high vaulted ceilings, cedar interiors, and an open floor-plan. Landscaped yard with sprinkler system. New, heat-reflective roof with 50 year warrantee against defects installed in 2021.
Past Activity
  • Nov 29, 2021 Sold for $1,665,000
  • Oct 21, 2021 Under Contract
  • Oct 11, 2021 Listed at $1,495,000
  • May 24, 2019 Sold for $1,190,000
  • Apr 14, 2019 Under Contract
  • Apr 05, 2019 Listed at $1,200,000
  • Jan 19, 2019 Off Market
  • Aug 28, 2018 Listed at $1,260,000
  • Aug 06, 2018 Off Market
  • Jul 10, 2018 Back to Active
  • May 19, 2018 Under Contract
  • May 16, 2018 Listed at $1,260,000
  • Mar 16, 2018 Off Market
  • Jan 31, 2018 Price $1,298,000
  • Oct 17, 2017 Listed at $1,340,000
More Details
  • Owner, Tax & Resale History
  • Price / ft²: $635
  • Zoning: 05 - R-5 Residential District
  • Flood Zone: Zone X
  • View: Coastline, Mountain, Ocean, Sunrise
  • Furnished: None
  • Property Condition: Excellent
  • Security Features: Key
  • Amenities: Bedroom on 1st Floor, Entry, Full Bath on 1st Floor, Landscaped, Patio/Deck, Storage
  • TMK: 1-4-2-96-35-0
  • Tax Assessed Land: $899,300
  • Tax Assessed Improvements: $453,700
  • Tax Assessed Total: $1,353,000
  • Courtesy: Compass
  • MLS: 202124709
About Hillcrest Kailua
See this aerial video of homes in Hillcrest.

The Hillcrest neighborhood of Kailua follows the pattern of the other upscale neighborhoods that line the heights of Oahu. Owners eagerly climb these rises to revel in the views they afford so beautifully. Depending on where you are, lots in Hillcrest can look out at the calm waters of Enchanted Lake, the active ocean depths of Kailua Bay, and the emerald greenery of the Koolau Mountains.

These abodes bring other benefits as well that are less dramatic, but equally important. Half of the streets in this neighborhood are cul-de-sacs, where owne  ... Read more
The MLS properties are based on information from the Multiple Listing Service of Hicentral MLS, Ltd. Listings last updated on January 20, 2026.Information is deemed reliable but not guaranteed.
Other Kailua Homes
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29 Alala Rd
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1233 Keolu Dr
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1209 Mokapu Blvd
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1205 Kupau St
4 Bds | 3 Ba
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Multi-Family

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  • Sold 11/29/21 at $1,665,000
    (List Price: $1,495,000)
Description
Open on Saturday 10/16 and Sunday 10/17 from 2-5 PM each day. Seller requests highest & best offers by 10:00 AM on Tuesday 10/19. Breathtaking views from every level. This beautiful home is perched on the most desired side of Hill Crest with picture windows that frame Kailua bay, Lanikai Mountain and Bellows. The home encompasses 3 large bedrooms and 2 large lanai's, high vaulted ceilings, cedar interiors, and an open floor-plan. Landscaped yard with sprinkler system. New, heat-reflective roof with 50 year warrantee against defects installed in 2021.
    The MLS properties are based on information from the Multiple Listing Service of Hicentral MLS, Ltd. Listings last updated on January 20, 2026.Information is deemed reliable but not guaranteed.
    • Nov 29, 2021 Sold for $1,665,000
    • Oct 21, 2021 Under Contract
    • Oct 11, 2021 Listed at $1,495,000
    • May 24, 2019 Sold for $1,190,000
    • Apr 14, 2019 Under Contract
    • Apr 05, 2019 Listed at $1,200,000
    • Jan 19, 2019 Off Market
    • Aug 28, 2018 Listed at $1,260,000
    • Aug 06, 2018 Off Market
    • Jul 10, 2018 Back to Active
    • May 19, 2018 Under Contract
    • May 16, 2018 Listed at $1,260,000
    • Mar 16, 2018 Off Market
    • Jan 31, 2018 Price $1,298,000
    • Oct 17, 2017 Listed at $1,340,000
    See this aerial video of homes in Hillcrest.

    The Hillcrest neighborhood of Kailua follows the pattern of the other upscale neighborhoods that line the heights of Oahu. Owners eagerly climb these rises to revel in the views they afford so beautifully. Depending on where you are, lots in Hillcrest can look out at the calm waters of Enchanted Lake, the active ocean depths of Kailua Bay, and the emerald greenery of the Koolau Mountains.

    These abodes bring other benefits as well that are less dramatic, but equally important. Half of the streets in this neighborhood are cul-de-sacs, where owne  ... Read more
    Other Kailua Homes
    $1,495,000
    29 Alala Rd
    2 Bds | 2 Ba
    636 ft²
    $1,490,000
    1233 Keolu Dr
    5 Bds | 3 Ba
    1,644 ft²
    $1,520,000
    1209 Mokapu Blvd
    3 Bds | 3 Ba
    1,808 ft²
    $1,465,000
    1205 Kupau St
    4 Bds | 3 Ba
    2,440 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.