44 Kaupakalua Rd

Haiku, HI 96708

$2,500,000
Price
4
Beds
2
Baths
2,920 Sq. Ft.
$856 / Sq. Ft.
2,920
Sq. Ft.
$856
per Sq. Ft.
Open: 2/12 09:00AM - 12:00PM
Open: 2/12 09:00AM - 12:00PM
a front view of a house with garden
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a living room with furniture and a flat screen tv
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a kitchen with stainless steel appliances granite countertop a stove and a refrigerator
a kitchen with stainless steel appliances granite countertop a table and chairs in it
a kitchen with stainless steel appliances granite countertop a sink a stove and a refrigerator
a kitchen with granite countertop a stove a sink a dining table and chairs
a kitchen with stainless steel appliances granite countertop a stove and a view of living room
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a bathroom with a toilet a sink and a mirror
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a bathroom with a sink and a mirror
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Description

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...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. Rare offering a main residence plus a private detached 'ohana on 2.86 acres in Haiku?
  1. Listed by Ashley Moniz • License #RS-81995 • Five Star Realty Inc.
    P: (808)-829-6656 ashley.moniz@fivestarrealty.org

Property Details for 44 Kaupakalua Road

View
Mountain/Ocean
Waterfront Features
None
Waterfront
No

Open Houses

Thursday, Feb 12th

9:00 AM - 12:00 PM

Public

LISTING UPDATED: 01/06/2026 01:46 PM

Property Details for 44 Kaupakalua Road

StatusActive
MLS #407795
Days on Market57
Taxes-
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / SF w/Det Ohana or Cottage
Year Built1977
Lot Size2.86 AC / 124,669 SF
CountyMaui County

Location

Listing Courtesy of Five Star Realty Inc., Ashley Moniz, License #RS-81995
Add your commute

Building Information for 44 Kaupakalua Road

Stories-Year Built1977Building Size-Lot Size2.86 AC / 124,669 SF

Payment Calculator

$13,270 per month

30 year fixed, 6.15% Interest

Principal and Interest

$12,185

Property Taxes

$1,085

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 44 Kaupakalua Road

Summary
Location and General Information
  • Coordinates: -156.265456, 20.917286
  • Latitude: 20.917286
  • Longitude: -156.265456
  • View YN: Yes
  • FIPS Code: 15009
  • Flood Zone: No
  • Multiple Address: 44 Kaupakalua Rd
Taxes and HOA Information
  • Tax Other Annual Assessment Amount: 0.0
Parking
  • Carport Spaces: 2.0
  • Carport: Yes
  • Covered Spaces: 4.0
  • Garage Spaces: 2.0
  • Garage: Yes
  • Parking Features: Carport, No Garage
Property Information
Lot Information
  • Building Area Total: 3920.0
  • Building Area Units: Square Feet
  • Living Area: 2920.0
  • Lot Size Units: Acres
  • MLS Area Major: Haiku
  • Carport Parking SQFT Hous: 448.0
  • CPR: 0000
  • Ohana Garage Parking SQFT: 418.0
  • Ohana Liv A SF: 1000.0
  • Ohana Year Built: 2002.0
Interior and Exterior Features
Exterior Features
  • Patio And Porch Features: Ohana Covered Lanai/Deck
Interior Features
  • Ohana Beds: 1.0
  • Ohana Baths: 2.0
  • Bathrooms: 2
  • Heating YN: No

Property History for 44 Kaupakalua Road

DateEvent & SourcePriceAppreciation
Dec 4, 2025

Listed (Active)

HICENTRAL #202526423

$2,500,000—
Nov 13, 2025

Listed (Active)

MAUIMLS #407795

$2,500,000—
DateEvent & SourcePrice
12/04/2025

Listed (Active)

HICENTRAL #202526423

$2,500,000
11/13/2025

Listed (Active)

MAUIMLS #407795

$2,500,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 44 Kaupakalua Road

Taxable ValueLand$1,306,500Additions$525,200Total$1,831,700
Tax Record2025$13,023 ($1,085 / month)
Home Facts
Beds4Baths4Total Finished SqFt1,920 SqFtAbove Grade Finished SqFt1,920 SqFtStories1Lot Size124,669 SqFtStyleSingle Family ResidenceYear Built1977ZoningAGRCountyMAUIAPN2-8-006-041

Schools near 44 Kaupakalua Road

This home is within Hawaii Department Of Education.
Rating
School
Type
Grades
Distance
Haiku Elementary School
Public - PK to 5
Samuel Enoka Kalama Intermediate School
Public - 6 to 8
King Kekaulike High School
Public - 9 to 12
Kulanihakoi High School
Public - 9
Rating
School
Distance
Haiku Elementary School
PublicPK to 5

Samuel Enoka Kalama Intermediate School
Public6 to 8

King Kekaulike High School
Public9 to 12

Kulanihakoi High School
Public9

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 44 Kaupakalua Road, Haiku, HI 96708

44 Kaupakalua Road is a single family home for sale in Haiku, HI 96708. This property was listed for sale on November 14, 2025 by Five Star Realty Inc., it's currently listed at $2,500,000. This listing's school district is Hawaii Department Of Education. Nearby schools include Haiku Elementary School, Samuel Enoka Kalama Intermediate School and King Kekaulike High School. 44 Kaupakalua Road is a 4-bed, 2-bath, 2,920 sqft single family home built in 1977.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Five Star Realty Inc., Ashley Moniz, License #RS-81995

Based on information from one of the following Multiple Listing Services: Hawaii HIS, MAUI MLS and Hi Central. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Hawaii HIS, MAUI MLS and Hi Central is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.