Discover a truly magical retreat featuring 2 homes on 2.86 acres in the heart of Haiku. Privately positioned on a premium corner lot, this retreat is framed by lush tropical greenery and crowned with the elegance of solid copper roofing, a rare statement of craftsmanship and longevity. A short distance from the main home which is 4 bedrooms 2 Bath and sits a generous detached Ohana, complete with 1 bedroom, 2 baths, and spacious living areas that are ideal for multi-generational living, guests, or income potential. The grounds are truly remarkable. Breezy, peaceful, and full of natural beauty this property embodies the best of Upcountry Maui living.
For sale
$2,500,000
44 Kaupakalua Rd, Haiku, HI 96708
4beds
2baths
2,920sqft
Est.:
Single Family Residence, Residential
Built in 1977
2.86 Acres Lot
$2,385,200 Zestimate®
$856/sqft
$-- HOA
What's special
Natural beautyLush tropical greenerySolid copper roofingGenerous detached ohanaPremium corner lot
- 47 days |
- 547 |
- 28 |
Zillow last checked: 8 hours ago
Listing updated: November 18, 2025 at 10:20am
Listing Provided by:
Ashley Moniz RS-81995 808-829-6656,
Five Star Realty Inc.
Source: RAM,MLS#: 407795
Tour with a local agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 2
Interior area
- Total structure area: 3,920
- Total interior livable area: 2,920 sqft
Property
Parking
- Total spaces: 4
- Parking features: Carport, No Garage
- Garage spaces: 2
- Carport spaces: 2
- Covered spaces: 4
Features
- Patio & porch: Ohana Covered Lanai/Deck
- Has view: Yes
- View description: Mountain/Ocean
- Has water view: Yes
- Water view: Mountain/Ocean
- Waterfront features: None
Lot
- Size: 2.86 Acres
Details
- Parcel number: 2280060410000
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence, Residential
Condition
- Year built: 1977
Community & HOA
Location
- Region: Haiku
Financial & listing details
- Price per square foot: $856/sqft
- Tax assessed value: $1,638,100
- Annual tax amount: $11,294
- Date on market: 11/18/2025
Estimated market value
$2,385,200
$2.27M - $2.50M
$5,163/mo
Price history
Price history
| Date | Event | Price |
|---|---|---|
| 11/18/2025 | Listed for sale | $2,500,000$856/sqft |
Source:  RAM #407795 Report a problem | ||
Public tax history
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | $11,294 +57.5% | $1,638,100 +40.6% |
| 2023 | $7,169 +26.9% | $1,164,900 +20.7% |
| 2022 | $5,648 +18.5% | $965,500 +11.3% |
Find assessor info on the county website
BuyAbility℠ payment
Est. payment
$13,502/mo
Principal & interest
$12314
Home insurance
$875
Property taxes
$313
Climate risks
Neighborhood: 96708
Nearby schools
GreatSchools rating
- 6/10Haiku Elementary SchoolGrades: PK-5Distance: 3.7 mi
- 5/10Samuel Enoka Kalama Intermediate SchoolGrades: 6-8Distance: 5.8 mi
- 5/10King Kekaulike High SchoolGrades: 9-12Distance: 7.4 mi
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