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$1,950,000 Sale Pending

  • For Sale
  • Pending
  • Multi-Family
  • 4 Total Beds
  • 2 Full Baths
  • Fee Simple
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RARE offering, a main residence plus a private detached Ohana on 2.86 acres in Haiku. Discover this truly magical retreat featuring 2 homes. 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.

Full Property Details for 44 Kaupakalua Rd

General

  • Price: $1,950,000
  • Taxes: $13,023
  • Status: Pending
  • Type: Multi-Family
  • Source: Honolulu_Board_Of_Realtors
  • MLS ID: 202526423
  • Updated: 6/29/2026
  • Added to Site: 268 day(s) ago

Interior

  • Furnishings: Unfurnished
  • Flooring: Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 4

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Carports: Yes
  • Total Spaces: 4
  • Parking Features: Carport, Garage, Two Car Garage, Two Spaces

Location

  • Area: Maui
  • County: Maui
  • Subdivision: MAKAWAO

School Information

  • Elementary School: Haiku
  • Middle School: Kalama
  • High School: Kekaulike

Community

  • Assoc. Fees Include: None

Utilities

  • Sewer: Cesspool, Septic Tank
  • Water: Public
  • Cable Available: Yes
  • Utility Description: Above Ground Utilities, Cable Available, Electricity Available, High Speed Internet Available, Phone Available, Septic Available, Water Available

Structural Information

  • Architectural Style: Multi-Family
  • Detached/Attached: Detached
  • Construction: Double Wall, Wood Frame
  • Stories/Levels: 2
  • Square Feet: 2,920
  • Living Area: 2,920 Sq. Ft.
  • Year Built: 1977
  • Property Condition: Excellent

Additional Structures

  • Other Structures: Workshop

Lot Features

  • Property View: Garden
  • Lot Size: 124669
  • Topography: Sloping
  • Lot Features: Corner Lot, Irregular Lot, Wooded
  • Zoning: 03 - R10 - Residential District

Financial Considerations

  • Assessment Amount: $1,831,700
  • Tax Amount: $13,023

Disclosures and Reports

  • Special Conditions: None
  • Land Tenure: Fee Simple
  • Inclusions: Cable TV, Dishwasher, Disposal, Dryer, Microwave, Range Hood, Refrigerator, TV Antenna, Washer, Water Heater
  • Disclosures/Reports: None
  • Disclosures/Rstr.: None
  • Property ID: 2-2-8-006-041-0000

Listed by Five Star Realty, Inc.

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Listing agent

— 44 Kaupakalua Rd —

  • Five Star Realty, Inc.

(808) 382-6871

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 44 Kaupakalua Rd

School District:Hawaii Department of Education
NameGradesDistance
Haiku Elementary School
105 Pauwela Rd, Haiku-Pauwela, HI 96708
PK-53.7 mi
Samuel Enoka Kalama Intermediate School
120 Makani Road, Makawao, HI 96768
6-85.7 mi
King Kekaulike High School
121 Kula Hwy, Pukalani, HI 96768
9-127.3 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 44 Kaupakalua Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
4/09/2026
Price Reduced
$1,950,000
-11.36%
MLS
2/05/2026
Price Reduced
$2,200,000
-12%
MLS
12/04/2025
Listed
$2,500,000
—
MLS
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 44 Kaupakalua Rd

Year
Property Taxes
Change
Tax Assessment
Change
2026
$13,873
7%
$1,847,000
1%
2025
$13,023
82%
$1,831,700
57%
2023
$7,169
27%
$1,164,900
55%
2022
$5,648
18%
$750,700
-13%
2021
$4,768
-8%
$867,400
-7%
2020
$5,175
-8%
$934,700
—
2018
$5,618
11%
$936,400
10%
2019
$5,060
126%
$851,800
-13%
2017
$2,240
9%
$983,100
3%
2016
$2,048
6%
$958,500
6%
2015
$1,930
13%
$901,800
5%
2013
$1,713
—
$862,900
8%
2013
$1,713
—
$796,800
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 44 Kaupakalua Rd

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Listed by Five Star Realty, Inc.

44 Kaupakalua Road, Haiku, HI 96708 (MLS# 202526423) is a Multi-Family property with units containing 4 bedrooms and 2 full bathrooms. 44 Kaupakalua Road is currently listed for $1,950,000 and was received on December 04, 2025. Want to learn more about 44 Kaupakalua Road? Do you have questions about finding other Multi-Family real estate for sale in Haiku? You can browse all Haiku real estate or contact a Coldwell Banker agent to request more information.

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