Tucked onto one of Kalaheo Hillside's most sought-after streets, 445 Iliwahi Loop is a fully reimagined 4-bed, 3-bath retreat blending timeless island architecture with a clean, considered renovation — vaulted ceilings, an open great room flowing to covered lanais, and walls of glass framing the pool, gardens and fountains. This generous lot sits against the conservation hillside adding to the peace and quiet of this location.
The chef's kitchen pairs a Viking range and Sub-Zero refrigeration w/a generous island open to the dining & living areas. Two primary suites suit multigenerational living or a guest wing, the spa-inspired primary bath w/a soaking tub and oversized shower. Two additional bedrooms w/shared bath PLUS 2 office/flex rooms
Outside is your own resort: a sparkling pool (plus spa hookup), mature landscaping, a garden gazebo and covered lanai seating for golden-hour gatherings. NEM metering, 2 Tesla Powerwalls, + a new GACO roof! Freshly painted inside & out, new flooring, lighting & fans throughout.
Minutes to Kailua Beach, a short hop to Marine Corps Base Hawaii, and moments from H-3, Pali and Likelike — with Aikahi Shopping Center and dining close at hand.
Active under contract
Price increase: $105K (7/4)
$2,300,000
445 Iliwahi Loop, Kailua, HI 96734
4beds
2,422sqft
Single Family Residence
Built in 1958
-- sqft lot
$2,144,700 Zestimate®
$950/sqft
$-- HOA
What's special
Sparkling poolVaulted ceilingsMature landscapingGarden gazebo
- 10 days |
- 3,169 |
- 243 |
Zillow last checked:
Listing updated:
Listed by:
Leanna Wolff 808-551-0039,
eXp Realty,
Sherine M Duncan 808-554-2262,
eXp Realty
Source: HiCentral MLS,MLS#: 202611972
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 3
- Full bathrooms: 3
Features
- Bedroom on Main Level, Full Bath on Main Level
- Flooring: Carpet, Ceramic Tile, Other
Interior area
- Total structure area: 2,682
- Total interior livable area: 2,422 sqft
Property
Parking
- Total spaces: 2
- Parking features: Boat, Carport, Driveway, Three or more Spaces, On Street
- Has carport: Yes
Features
- Levels: One
- Stories: 1
- Exterior features: Landscaping
- Pool features: In Ground, Tile
- Fencing: Fenced,Wall
- Has view: Yes
- View description: Garden, Mountain(s)
- Frontage type: Conservation,Other
Lot
- Features: Cleared, Other, Level, Steep Slope
- Topography: Level,Sloping,Terraced
Details
- Additional structures: Workshop
- Parcel number: 1440290800000
- Zoning description: 03 - R10 - Residential District
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Detached
- Property subtype: Single Family Residence
Materials
- Foundation: Slab
Condition
- Average Condition,Good Condition,Updated/Remodeled
- New construction: No
- Year built: 1958
- Major remodel year: 2019
Utilities & green energy
- Water: Public
- Utilities for property: Above Ground Utilities, Cable Available, Electricity Available, Other, Phone Available, Sewer Available, Water Available
Community & HOA
Community
- Features: Deck/Porch, Patio, Storage Facilities
- Security: Key Card Entry
- Subdivision: Kalaheo Hillside
Location
- Region: Kailua
Financial & listing details
- Price per square foot: $950/sqft
- Tax assessed value: $1,840,200
- Annual tax amount: $5,788
- Date on market: 6/23/2026
- Inclusions: AC Window Unit, Book Shelves, Cable TV, Ceiling Fan, Chandelier, Compactor, Dishwasher, Disposal, Dryer, Lawn Sprinkler, Photovoltaic – Leased, Photovoltaic - Owned, Range Hood, Range/Oven, Refrigerator, Smoke Detector, Solar Heater, Washer
Estimated market value
$2,144,700
$2.04M - $2.25M
$7,861/mo
Price history
| Date | Event | Price |
|---|---|---|
| 7/4/2026 | Contingent | $2,300,000$950/sqft |
Source: eXp Realty #202611972 Report a problem | ||
| 7/4/2026 | Listed for sale | $2,300,000$950/sqft |
Source: eXp Realty #202611972 Report a problem | ||
| 7/4/2026 | Contingent | $2,300,000+4.8%$950/sqft |
Source:  HiCentral MLS #202611972 Report a problem | ||
| 6/24/2026 | Listed for sale | $2,195,000+56.8%$906/sqft |
Source: HiCentral MLS #202611972 Report a problem | ||
| 6/21/2019 | Listing removed | $1,400,000$578/sqft |
Source: Coldwell Banker Pacific Properties - Diamond Head - Kahala #201907474 Report a problem | ||
| 3/28/2019 | Listed for sale | $1,400,000+226.3%$578/sqft |
Source: Coldwell Banker Pacific Prop. #201907474 Report a problem | ||
| 3/22/2000 | Sold | $429,000$177/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $5,789 -10.6% | $1,773,900 -10% |
| 2024 | $6,478 +2.2% | $1,970,800 +3.1% |
| 2023 | $6,340 -46.4% | $1,911,400 +12.5% |
| 2022 | $11,836 +41.8% | $1,698,700 +24.3% |
| 2021 | $8,348 +10.6% | $1,366,500 +5.9% |
| 2020 | $7,546 +107.2% | $1,290,100 +15.1% |
| 2019 | $3,641 +5.4% | $1,120,400 +5% |
| 2018 | $3,456 +7.6% | $1,067,300 +7% |
| 2017 | $3,210 +2.9% | $997,200 +2.6% |
| 2016 | $3,121 +9.6% | $971,600 +8.8% |
| 2015 | $2,847 +10.8% | $893,400 +3.8% |
| 2014 | $2,568 | $861,000 +8.4% |
| 2013 | -- | $794,300 +0.5% |
| 2012 | -- | $790,300 -2.9% |
| 2011 | -- | $813,800 -5.6% |
| 2010 | -- | $862,100 +1.3% |
| 2009 | -- | $851,200 -9.6% |
| 2008 | -- | $941,300 -4.7% |
| 2007 | -- | $987,300 +7.6% |
| 2006 | -- | $917,900 +16% |
| 2005 | -- | $791,400 +24.4% |
| 2004 | -- | $636,200 +30.5% |
| 2003 | $1,564 +23.1% | $487,600 +13.8% |
| 2002 | $1,271 | $428,600 |
| 2000 | -- | -- |
| 1999 | -- | $355,600 |
Find assessor info on the county website
Monthly payment
Est. payment$--/mo
Payment breakdown
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HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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Climate risks
Neighborhood: 96734
Nearby schools
GreatSchools rating
- 7/10Aikahi Elementary SchoolGrades: PK-6Distance: 0.5 mi
- 7/10Kailua Intermediate SchoolGrades: 7-8Distance: 2 mi
- 10/10Kalaheo High SchoolGrades: 9-12Distance: 0.8 mi
Schools provided by the listing agent
- Elementary: Aikahi
- Middle: Kailua
- High: Kalaheo
Source: HiCentral MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
A local agent can set up tours, give advice and negotiate with sellers.
- Hawaii
- Honolulu County
- Kailua
- 96734
- 445 Iliwahi Loop
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