3955 Round Top Dr , Honolulu, HI, 96822 in TANTALUS

3955 Round Top Dr , Honolulu, HI, 96822 in TANTALUS
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$5,300,000

3955 Round Top Dr , Honolulu, HI, 96822
5 beds3 baths3,360 sqft

5

Bedrooms

3

Bathrooms

3,360

Sqft

N/A

Floor

1937

Year Built

10

Parking

How do you feel about this one?

Description

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.

Views

CityCoastlineDiamond HeadGardenMountainOceanSunriseSunset

Features

Flooring - Hardwood
Parking - 3 Car+
Parking - Driveway
Construction - Above Ground
Construction - Wood Frame
Property Condition - Excellent

Amenities

Bedroom on 1st Floor
Full Bath on 1st Floor
Landscaped

Utilities

Cesspool
Internet
Overhead Electricity
Telephone
Water Catchment

Inclusions

Ceiling Fan
Dryer
Microwave
Range/Oven
Refrigerator
Washer
Water Heater

Lot & Legal

Frontage: Other
Topography: Down Slope, Gentle Slope, Level, Steep Slope
Stories: Two
Easements: Driveway, Other

Listing History

MLS 202618721
  1. Oct 20, 2026Active
  2. Oct 20, 2026Listedat $5,300,000

Includes all MLS listings of this same physical unit (matched by TMK).

Schedule Showing

Listing Details

MLS #202618721
StatusActive
First SeenOctober 20, 2026

Property Details

Property TypeSingle Family
StyleDetach Single Family
Land TenureFee Simple
Remodeled2021
Sub-TypeSingle Family
NeighborhoodTantalus
MLS AreaMetro
Lot Size76970 sqft
TMK1-2-5-017-009
Flood ZoneZone X· Minimal risk

Monthly Costs

All amounts are monthly

Property Taxes(-$120,000 exemption)$124
Total Monthly$124

MLS# 202618721

Listing Courtesy of: Compass

Agent: Jason M Carey

Co-listing agent: Ben Puccetti

Based on information from the Multiple Listing Service of HiCentral MLS, Ltd. Listing information last updated: October 26, 2026.

Information is deemed reliable but not guaranteed. All properties are subject to prior sale, change, or withdrawal.

All right, title, and interest in each copy of every MLS Compilation shall at all times remain vested in HiCentral MLS, Ltd.

© 2026 HiCentral MLS, Ltd. All rights reserved.

Equal Housing Opportunity