For sale

$55,000,000

Est. $321,416/mo —

•

10,047

sq ft

3735 Diamond Head Rd, Honolulu, HI 96816

About this home

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.

Single-familyProperty Type

1967Year Built

2.05 acresLot Size

$5,474Price/Sq.Ft.

10 spacesParking

Listed by Noel Shaw • Hawaii Life

Contact: (800) 667-5028

Listing updated: Sep 16, 2026 at 03:54pm

Redfin checked: 2 minutes ago

•Source:HiCentral MLS #202520629

Redfin agents who toured

Rare Package Deal! As highlighted in the photos, this massive estate includes a stunning oceanfront home plus two additional lots offering prime development potential. The main residence sits elevated on the hillside, capturing panoramic views over...
1 year ago• May not reflect the current state of the home
Gill Mara (R)
Redfin agent

Payment calculator

$321,416 per month

Principal and interest$300,158

Property taxes

$6,592

HOA dues

Home insurance

$14,667

Utilities

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Next available date: Sunday, September 20

Open houses

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Around this home

Schools

K - 12
Preschool & daycare

Kahala Elementary School

Public PreK-5 • Assigned • 1.5mi

4/10

Kaimuki Middle School

Public 6-8 • Assigned • 1.0mi

10/10

Kalani High School

Public 9-12 • Assigned • 2.3mi

10/10

Provided by GreatSchools

About

Waialae-Kahala

Waialae-Kahala, located between Diamond Head and Hawaiʻi Kai, is a coastal and residential East Honolulu neighborhood with oceanfront parks and a polished retail corridor. The neighborhood’s character concentrates around the Kahala Mall and Waialae Avenue, where boutiques, local cafés, and everyday services keep sidewalks active. Kahala Theatre, Arancino at The Kahala, and Waiola Shave Ice act as familiar community pillars. Streets shift from mid-century ranch homes to gated estates, with palms and low lava-rock walls setting a calm streetscape. Kapiʻolani Community College’s Saturday Farmers’ Market adds a weekly ritual near the Diamond Head edge. Beach access points and pocket parks frame a lifestyle tied to trade winds and shoreline views.

Provided by Walk Score and Local Logic

Market insights

3735 Diamond Head Rd · $55,000,000

DAYS ON MARKET

The average home goes pending in 65 days.

SALE-TO-LIST

Most homes are selling 1% below list price.

LIST PRICE

Median list price in this area is $1,235,762. (98% lower than this home)

PRICE DROP

11% of homes in this area have had a price drop in the past month.

Property details

Interior
Exterior
Finance

Kitchen

Living

Dining

Interior features
Unfurnished
Bedroom on main level
Full bath on main level
Entry foyer
Guest quarters

Bedrooms
Guest quarters (separate room type noted)

Bathrooms
10 full bathrooms
1 half bathroom

Flooring
Ceramic tile
Hardwood

Sale and tax history for 3735 Diamond Head Rd

Sale History
Tax History

Date

Event

Price

HiCentral MLS #202520629

Oct 1, 2025

Listed

$55,000,000

$5,474/sq ft

HiCentral MLS #202520630

Oct 1, 2025

Listed

$43,000,000

$4,280/sq ft

Located on Diamond Head Road, Ho‘oluana Estate is one of Honolulu’s last remaining legacy estate-sized properties. Zoned R-7.5 and encompassing nearly 80,000 square feet, the estate features an expansive residences and several open lots, offering sweeping ocean views, private/deeded 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. Neighboring property located at 3735 Diamond Head Road A, is also available for sale, presenting a rare opportunity to establish a landmark estate in one of Honolulu’s most prestigious locations. Property details may not match tax records.

HiCentral MLS #202506223

Sep 30, 2025

Listing Removed

—

Mar 16, 2025

Listed

$43,000,000

$4,280/sq ft

HiCentral MLS #202421173

Sep 30, 2025

Listing Removed

—

Dec 8, 2024

Listed

$55,000,000

$5,474/sq ft

RENT. #1

Jul 8, 2022

Price Changed

$16,000

$2/sq ft

Public Records

Oct 24, 2018

Sold

$550,000

$55/sq ft

Year

Property tax

Land + Additions

Assessment*

2022

$37,308 (+14.4%)

$8,208,700 + $2,450,700

$10,659,400

2021

$32,617 (+0.4%)

$8,208,700 + $2,450,700

$10,659,400

2020

$32,474 (−0.9%)

$6,857,900 + $2,461,100

$9,319,000

2019

$32,764 (+2.7%)

$7,221,600 + $2,056,700

$9,278,300

2018

$31,908 (−11.7%)

$7,533,300 + $1,827,700

$9,361,000

2017

$36,153 (−33.7%)

$7,325,500 + $1,791,000

$9,116,500

2016

$54,497 (+40.7%)

$8,858,100 + $1,471,300

$10,329,400

2014

$38,720 (+39.3%)

$13,699,900 + $1,410,600

$15,110,500

2013

$27,806 (−8.0%)

$9,510,600 + $1,552,500

$11,063,100

2012

$30,224

$6,827,100 + $1,117,500

$7,944,600

Public record

Public record
Permits

Beds

Baths

5.5

Stories

Lot width

—

Lot depth

—

Lot size

1.84 Acres

Year renovated

—

Finished Sq. Ft.

6,213

Unfinished Sq. Ft.

—

Total Sq. Ft.

6,213

Year built

1967

Style

Single Family Residential

County

Honolulu County

APN

1 3 1 039 005 0000

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Mar 7, 2023.

Jun 7, 2023 • Final

Building

Construct a new exterior staircase and a retaining wall at the rear of the property.

ADU

Grading

Oct 13, 2021 • Final

Building

Reinforce an existing masonry retaining wall. Relocate a utility pullbox with conduits.

Electrical

Grading

Permit history is from public records and may be incomplete or inaccurate. Redfin and its agents make no representations about the property condition or permit status. Buyers should independently verify all information.

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

Fire Factor

We're working on getting current and accurate fire risk information for this home.

Heat Factor

We're working on getting current and accurate heat risk information for this home.

Wind Factor

We're working on getting current and accurate wind risk information for this home.

1/10 Air Factor

Minimal risk of unhealthy air over next 30 years

Provided by First Street

Historical weather

Honolulu, HI • 96816

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

53/ 100

Moderate sunlight

Sunscore

There appears to be some shading by surrounding buildings, terrain, and vegetation.

5.7 hrs

4.6 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 3735 Diamond Head Rd

$46,347,416

$8.7M under list price of $55.0M

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $3.0M to $16.5M.

SOLD SEP 11, 2026
$16,500,000 Last sold price
5 beds6 baths5,578 sq ft
218 Kaalawai Pl, Honolulu, HI 96816
$2516/sq ft
smaller lot
31 years newer
SOLD AUG 26, 2026
$6,377,000 Last sold price
5 beds6 baths7,953 sq ft
3124 Noela Dr, Honolulu, HI 96815
$4672/sq ft
smaller lot
22 years newer
SOLD JUN 12, 2026
$5,725,000 Last sold price
4 beds5.5 baths4,832 sq ft
4218 Kaimanahila St, Honolulu, HI 96816
$4289/sq ft
smaller lot
47 years newer
SOLD JAN 23, 2026
$3,100,000 Last sold price
6 beds7 baths5,798 sq ft
736 Ulili St, Honolulu, HI 96816
$4939/sq ft
smaller lot
30 years newer
SOLD MAR 9, 2026
$3,038,000 Last sold price
4 beds3 baths2,305 sq ft
4305 Kaikoo Pl, Honolulu, HI 96816
$4156/sq ft
smaller lot
11 years older
SOLD MAR 16, 2026
$8,250,000 Last sold price
8 beds10.5 baths16,268 sq ft
3239 Noela Dr, Honolulu, HI 96815
$4967/sq ft
smaller lot
22 years newer

Rental earnings

Est. $8,469 per month, based on comparable rentals

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