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5 Beds
3 Baths
3,360 sqft

$5,300,000

3955 Round Top Drive, Honolulu HI, 96822

Price per sqft$1,577.38
Built in1937
Property size3,360 sqft
Property typeResidential

Overview

Active

Listed Oct 20, 2026

Updated 3h ago

Perched high above Honolulu on Round Top Drive, this extraordinary estate spans six parcels totaling 76,970 square feet and offers a rare combination of privacy, history, and unrivaled panoramic views stretching from Diamond Head and the Pacific Ocean across the Honolulu skyline to Manoa Valley and the surrounding mountains. Held by the same family for nearly a century, the property is anchored by a 5-bedroom, 3-bath residence with a total of 3,360 square feet of interior living space. Originally built in 1937 and later expanded with an addition designed by renowned architect Alfred Preis, the home retains distinctive midcentury features and character throughout. A separate downstairs living area with its own kitchenette offers flexibility for extended family, guests, or rental use. Decades of thoughtful landscaping have created lush, established grounds with mature koa and fruit trees and a remarkable sense of privacy. The estate also presents significant potential for additional residences, a multi-generational compound, or a thoughtful reimagining, subject to buyer due diligence. A rare opportunity to own a legacy property of this scale, setting, and character in Honolulu.

$35,261/mo

Est. mortgage payment based on a $5,300,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
202618721

Interior Features

Bedrooms
5
Bathrooms
3
Basement
No

Exterior Features

Lot Size
1.77 Acres

Other Property Details

Taxes
$1,020
Tax Frequency
Annually
View
Yes
MLS provider logo

 

Courtesy of Compass, Jason M Carey

Listing Contact: (808) 825-4277 

Based on information from the Multiple Listing Service of HI - Honolulu Board of REALTORS® / HiCentral (HBR) listings last updated on 10/21/2026 7:40 PM UTC. Information is deemed reliable but not guaranteed. Copyright: 2026 by the Honolulu Board of REALTORS®/ HICentral. Some of the active listings appearing on this site may be listed by other REALTORS®. If you are interested in those active listings, our company may represent you as the buyer's agent. If the active listing you are interested in is our company's active listing, you may speak to one of our agents regarding your options for representation. IDX information is provided exclusively for consumers' personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the MLS. The MLS may, at its discretion, require the use of other disclaimers as necessary to protect participants and/or the MLS from liability.

©2026 Honolulu Board of REALTORS®/ HICentral. All rights reserved. 

Data last updated 7:40 PM UTC, 10/21/2026

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