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$55,000,000

  • For Sale
  • Active
  • Single Family
  • 11 Beds
  • 10 Full Baths
  • 1 Partial Bath
  • 13,626 Sq. Ft.
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Located on Diamond Head Road, Ho'oluana Estate is one of Honolulu's last remaining legacy estate-sized properties, spanning over two acres across two adjacent parcels. Zoned R-7.5 and encompassing nearly 89,120 square feet, the estate features two residences and an open lot, offering sweeping ocean views, beachfront access, and exceptional flexibility for development or preservation. Perfectly positioned between Kahala and Waikiki, this property combines luxury, tranquility, and proximity to world-class surfing, shopping, dining, golf, hiking, and more. Offered as a singular acquisition under TMKs 1-3-1-039-042-0000 and 1-3-1-039-005-0000, Ho'oluana Estate presents a rare opportunity to establish a landmark estate in one of Honolulu's most prestigious locations. Property details may not match tax records. Last four digits of the listing TMK do not exist, these are used only for MLS entry purposes.

Full Property Details for 3735 Diamond Head Rd

General

  • Price: $55,000,000
  • Taxes: $84,636
  • Status: Active
  • Type: Single Family
  • Source: Honolulu_Board_Of_Realtors
  • MLS ID: 202520629
  • Updated: 10/2/2025
  • Added to Site: 106 day(s) ago

Rental Information

  • Complex Features: Deck/Porch, Patio, Storage Facilities

Interior

  • Interior Features: Bedroom on Main Level, Full Bath on Main Level
  • Furnishings: Unfurnished
  • Flooring: Ceramic Tile, Hardwood, Other

Rooms

Bathrooms

  • Total Bathrooms: 11
  • Full Bathrooms: 10
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 11

Additional Information

  • Pool: Yes
  • Pool Description: In Ground
  • Security/Safety: Key Card Entry

Exterior

  • Exterior Features: Landscaping

Parking

  • Garage: Yes
  • Total Spaces: 10
  • Parking Features: Boat, Driveway, Garage, Three or more Spaces

Location

  • Area: DiamondHd
  • County: Oahu
  • Subdivision: DIAMOND HEAD

Utilities

  • Utility Description: Above Ground Utilities, Electricity Available, Water Available

Structural Information

  • Architectural Style: Detached, Multiplex
  • Detached/Attached: Detached
  • Construction: Double Wall, Concrete, Wood Frame
  • Stories/Levels: 2
  • Square Feet: 13,626
  • Living Area: 10,047 Sq. Ft.
  • Year Built: 1967
  • Property Condition: Average Condition, Updated/Remodeled

Additional Structures

  • Other Structures: Workshop

Lot Features

  • Property View: Coastline, Garden, Mountain(s), Ocean
  • Mountain views: Yes
  • Lot Size: 89125
  • Frontage: Private Road
  • Fence: Yes
  • Topography: Level, Sloping
  • Lot Features: Other, Level
  • Zoning: 04 - R-7.5 Residential District
  • Fencing (Description): Fenced, Wall

Water Features

  • Water Front: Yes

Financial Considerations

  • Assessment Amount: $15,367,400
  • Tax Amount: $84,636

Disclosures and Reports

  • Special Conditions: None
  • Inclusions: AC Split, Blinds, Book Shelves, Dishwasher, Drapes, Lawn Sprinkler, Range/Oven, Refrigerator, Security System, Smoke Detector, Washer, Water Heater
  • Disclosures/Reports: None
  • Disclosures/Rstr.: None
  • Property ID: 1-3-1-039-005-9999

Listed by Hawaii Life

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Listing agent

— 3735 Diamond Head Rd —

  • Hawaii Life

(800) 667-5028

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 3735 Diamond Head Rd

School District:Hawaii Department of Education
NameGradesDistance
Kahala Elementary School
4559 Kilauea Avenue, Honolulu, HI 96816
PK-51.6 mi
Kaimuki Middle School
631 18th Avenue, Honolulu, HI 96816
6-81 mi
Kalani High School
4680 Kalaniana?ole Highway, Honolulu, HI 96821
9-122.3 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 3735 Diamond Head Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
10/02/2025
Listed
$55,000,000
9900%
MLS
10/24/2018
Sold
$550,000
—
Public Record
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 3735 Diamond Head Rd

Year
Property Taxes
Change
Tax Assessment
Change
2025
$33,674
-8%
$10,525,800
9%
2023
$36,740
-2%
$9,621,000
-8%
2022
$37,308
—
$10,497,000
-2%
2022
$37,308
14%
$10,659,400
14%
2021
$32,616
—
$9,319,000
—
2021
$32,616
—
$9,278,300
-1%
2019
$32,764
3%
$9,361,000
3%
2018
$31,908
-12%
$9,116,500
-12%
2017
$36,153
-34%
$10,329,400
-34%
2016
$54,497
3%
$15,570,600
3%
2015
$52,887
90%
$15,110,500
37%
2013
$27,806
—
$11,063,100
—
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 3735 Diamond Head Rd

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

Listed by Hawaii Life

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3735 Diamond Head Road, Honolulu, HI 96816 (MLS# 202520629) is a Single Family property with 11 bedrooms, 10 full bathrooms and 1 partial bathroom. 3735 Diamond Head Road is currently listed for $55,000,000 and was received on October 02, 2025. Want to learn more about 3735 Diamond Head Road? Do you have questions about finding other Single Family real estate for sale in Honolulu? You can browse all Honolulu real estate or contact a Coldwell Banker agent to request more information.

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