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3955 Round Top Drive, 
Honolulu, HI 96822

$5,300,000


5

Beds


3

Baths


3,360

Sq Ft


Single Family

Active

Listed by

Jason M Carey

, 

Ben Puccetti

Compass

Last updated:

October 22, 2026, 03:51 AM

MLS#

202618721

Source:

HI HBR

About This Home

3955 Round Top Drive

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.

Home Facts

Single Family

3 Baths

5 Bedrooms

Built in 1937

Subdivision & Development:

TANTALUS

Price Summary

5,300,000

$1,577 per Sq. Ft.

MLS #:

202618721

Last Updated:

October 22, 2026, 03:51 AM

Added:

2 day(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

5

Bathrooms

Total Bathrooms:

3

Full Bathrooms:

3

Interior

Living Area:

3,360 Sq. Ft.


Structure

Structure

Architectural Style:

Detached

Building Area:

3,360 Sq. Ft.

Year Built:

1937


Lot

Lot Size (Sq. Ft):

76,970


Finances & Disclosures

Finances

Price:

$5,300,000

Price per Sq. Ft:

$1,577 per Sq. Ft.

Source:HI HBR
Based on information from the Multiple Listing Service of HiCentral MLS, Ltd. listings last updated on October 22, 2026. Information is deemed reliable but not guaranteed. Copyright: 2026 by HiCentral MLS, Ltd.

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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.