Can you believe 2010 was the last time a home sold for more than $20 million on Oahu? It was 4653B Kahala Ave. purchased by Genshiro Kawamoto for $22 million.

Kahala Beach

Beach in Kahala where the last $20 home sale was in 2010

Back in the late 1980's to 1990 $20 million home sales were commonplace along Kahala Ave. at the peak of the Japanese Bubble. Here we are now in the year 2020. Last year, a home in Beachside got close with a $17.9 mil. sale.*

Will 2020 Be the Year for Another $20 million Sale? 

There are currently six homes on the market with asking prices over $20 million. With no surprise, all six homes are oceanfront and all six are in three areas that typically take out the top spot on Oahu for highest real estate sales. Diamond Head, Kahala and Kailua are sharing that load evenly with two listings in each respective neighborhood:

Diamond Head Offerings

3249 Diamond Head Road

3249 Diamond Head Road (MLS # 201913411) is asking $21.5 million

Situated on over a half acre off Diamond Head road, this 6 bed, 7.5 bath home has 7,500 sq. ft. under roof. It last sold for $10.4 million in 2006 and was previously owned by Jim Schuler - a local home builder/developer that sold his company to publicly traded DR Horton (who continues to develop homes all over Hawaii).

202 Kaikuono Place

202 Kaikuono Place (MLS # 201908386) is asking $23 million

Situated on a modest lot of 8,414 sq. ft., this 4 bed, 4.5 bath home has just over 4,800 sq. ft. under roof. It's orientated to have the trade winds at its back and has views along the Diamond Head shoreline that can produce nice sunsets during the winter. This home last sold for $14.2 million in 2015 and was previously owned by the late Lawrence Stupski, who once ran Charles Schwab.

Kahala Offerings

4679B Kahala Ave

4679B Kahala Ave (MLS # 201915741) is asking $23 million

Set on the largest parcel of all the offerings, this 6 bed, 6 bath home just under 5,000 sq. ft. is on over 1.7 acres. The current owner assembled 3 parcels that are included in the sale roughly 30 years ago and now is awaiting a new owner.

4505 Kahala Ave

4505 Kahala Ave. (MLS # 201914327) is asking $25 million (originally $30 million)

This one sold for $17 million in 2004 and is a 5 bed, 6.5 bath home just under 9,000 sq. ft. under roof. The lot is just under 1.3 acres. Some well known affluent families such as the Spaldings and Weinbergs have owned this trophy parcel over the years.

Kailua Offerings

1240 Mokulua Drive

1240 Mokulua Drive (MLS # 201930929) is asking $21 Million

This wold definitely take the cake for the highest Lanikai sale... Built in 2007, this 9 bed, 9.5 bath home is on .8 acres.It last sold for just over $5 million in the year 2000, so not a bad ROI for a 20 year hold if sold in this range.

145 Kailuana Loop

145 Kailuana Loop (MLS # 201926904) is asking $27.5 million

With the highest asking price for a single family home on Oahu, this 10 bed, 8 bath (+ 3 half baths) home is also the largest with over 14,000 sq. ft. under roof. Based on a price/sq. ft. of improvements, this would be the best buy of all six homes above $20 million. The owner paid $24 million back in 2006, so appears they're just looking to get their money out of it at this point.

* For a complete list of the highest single family home and condos sales on Oahu since 2001, visit our Luxury Real Estate Page