Search Listings Open Houses Buyer's 20% Rebate Sell for 2% Sell for $3,500 Statistics Help Tools Saved Searches Testimonials Blog Contact ☰

Oahu Real Estate Logo

We've sold 2,090+ listings for over $1.34 billion, saving our clients over $12 million. See our sales on Google Maps.

3955 Round Top Drive

Honolulu HI 96822 · Active · $5,300,000

Details · History · Additional Links

3955 Round Top Drive

See additional photos

Rebate20% Buyer's Rebate | $3,500 Flat Fee Selling | 2% Full Service Selling
DescriptionPerched 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.
StatusActive since 10-20-2026
MLS#202618721
Price$5,300,000
Original Price$5,300,000
Price Change (0.00%)
Beds / Baths / Half5 / 3 / 0
Parking Spaces10
Living Sq Ft3,360
Land Sq Ft76,970
Land TenureFS - Fee Simple
Address3955 Round Top Drive Honolulu HI 96822
RegionMetro
NeighborhoodTantalus
Days on Market12
Year Built1937
Year Remodeled2021
ConditionExcellent
ViewCity, Coastline, Diamond Head, Garden, Mountain, Ocean, Sunrise, Sunset
FrontageOther
PoolNone
Parking3 Car+, Driveway
Zoning61 - P-1 Restricted Preservatio
Flood ZoneZone X · See flood zone map · Explain flood zones
Monthly Tax$85
Assessed Land$378,600
Assessed Building$167,900
Assessed Total$546,500
Assessed Ratio970%
InclusionsCeiling Fan, Dryer, Microwave, Range/Oven, Refrigerator, Washer, Water Heater
AmenitiesBedroom on 1st Floor, Full Bath on 1st Floor, Landscaped
UtilitiesCesspool, Internet, Overhead Electricity, Telephone, Water Catchment
ConstructionAbove Ground, Wood Frame
Lot FeaturesClear, Irregular, Rim Lot, Wooded
FlooringHardwood
DisclosuresProperty Disclosure Stmt, See Remarks
Land RecordedRegular System
PossessionAt Closing
Sale ConditionsNone
TopographyDown Slope, Gentle Slope, Level, Steep Slope
Building StyleDetach Single Family
StoriesTwo
RoofingAsphalt Shingle
EasementsDriveway, Other
SecurityKey
Parcel #1-2-5-017-009-0000
Listing courtesy ofCompass
DateMLS#ChangeOld ValueNew ValueList PriceSold PriceAssessed TotalLandBuilding
10-20-2026202618721New ListingCSA$5,300,000$0$546,500$378,600$167,900
09-06-2021202023130ExpiredAX$4,750,000$0$328,900$242,900$86,000
09-05-2020202023130New ListingA$4,750,000$0$328,900$242,900$86,000
09-05-2020201926125ExpiredAX$4,750,000$0$385,700$320,500$65,200
11-27-2019201926125Price Decrease$5,000,000$4,750,000$4,750,000$0$385,700$320,500$65,200
10-02-2019201926125New ListingA$4,750,000$0$385,700$320,500$65,200
Photo 2 of 25

Photo 2 of 25 · Previous · Next or click photo · Top

Photo 3 of 25

Photo 3 of 25 · Previous · Next or click photo · Top

Photo 4 of 25

Photo 4 of 25 · Previous · Next or click photo · Top

Photo 5 of 25

Photo 5 of 25 · Previous · Next or click photo · Top

Photo 6 of 25

Photo 6 of 25 · Previous · Next or click photo · Top

Photo 7 of 25

Photo 7 of 25 · Previous · Next or click photo · Top

Photo 8 of 25

Photo 8 of 25 · Previous · Next or click photo · Top

Photo 9 of 25

Photo 9 of 25 · Previous · Next or click photo · Top

Photo 10 of 25

Photo 10 of 25 · Previous · Next or click photo · Top

Photo 11 of 25

Photo 11 of 25 · Previous · Next or click photo · Top

Photo 12 of 25

Photo 12 of 25 · Previous · Next or click photo · Top

Photo 13 of 25

Photo 13 of 25 · Previous · Next or click photo · Top

Photo 14 of 25

Photo 14 of 25 · Previous · Next or click photo · Top

Photo 15 of 25

Photo 15 of 25 · Previous · Next or click photo · Top

Photo 16 of 25

Photo 16 of 25 · Previous · Next or click photo · Top

Photo 17 of 25

Photo 17 of 25 · Previous · Next or click photo · Top

Photo 18 of 25

Photo 18 of 25 · Previous · Next or click photo · Top

Photo 19 of 25

Photo 19 of 25 · Previous · Next or click photo · Top

Photo 20 of 25

Photo 20 of 25 · Previous · Next or click photo · Top

Photo 21 of 25

Photo 21 of 25 · Previous · Next or click photo · Top

Photo 22 of 25

Photo 22 of 25 · Previous · Next or click photo · Top

Photo 23 of 25

Photo 23 of 25 · Previous · Next or click photo · Top

Photo 24 of 25

Photo 24 of 25 · Previous · Next or click photo · Top

Photo 25 of 25

Photo 25 of 25 · Previous · Next or click photo · Top