3735 Diamond Head Road

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.

11
beds

11
baths

10,047 Sq.Ft. LIVING AREA

2.05 Acres lot

Features & Amenities

Interior

total bedrooms11
Total bathrooms11
full bathrooms10
half bathroom1
Flooring Ceramic Tile, Hardwood, Other
other interior Features Bedroom on Main Level, Full Bath on Main Level

Area & Lot

Status For Sale
Living Area10,047 Sq.Ft.
Total Area13,626 Sq.Ft.
Lot Area2.05 Acres
MLS® ID202520629
TypeResidential
YEAR BUILT1967
Architecture StylesDetached, Multiplex
View DescriptionCoastline, Garden, Mountain(s), Ocean

Exterior

STORIES2
utilitiesAbove Ground Utilities, Electricity Available, Water Available
PoolIn Ground
lot featuresOther, Level
parkingBoat, Driveway, Garage, Three or more Spaces
security FeaturesKey Card Entry
other exterior FeaturesLandscaping

Financial

Sales Price$55,000,000
Real Estate Tax $84,636/yr

Courtesy of Noel Shaw

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Work With Rochelle

When it comes to buying or selling a luxury property, you deserve a strategic partner who understands the market, negotiates fiercely on your behalf, and delivers an exceptional experience at every turn. Led by nationally ranked broker Rochelle LeCavalier and her expert team at Douglas Elliman, with over $1 billion in career sales, we offer a rare combination of industry expertise, white-glove service, and proven results. From seasoned buyer specialists to sharp marketing minds and meticulous operations support, every member of our team is committed to one goal: helping you achieve yours with confidence and ease. Whether you’re seeking your dream home or maximizing the value of your property, the full support of her team, working seamlessly to ensure a results-driven, elevated experience. Ready to make your next move? Contact us today for a confidential conversation about your real estate goals.

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3735 Diamond Head Road

$55,000,000

Rochelle LeCavalier