Cliff May built houses on Oakmont Drive in Brentwood for Frederic Blow, who bought land there to develop. The best documented is the 1939 hacienda at 39 Oakmont Drive, which May called his first house built for millionaires; Blow’s own house was at 27 Oakmont Drive, dated 1940 to 1942.
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On one Brentwood street, Cliff May built for a developer and his neighbors, and turned a corner in his career: the first house he said he built for millionaires.
In the late 1930s, a developer named Frederic Blow bought land on Oakmont Drive in Brentwood, planned a group of houses, and kept one for himself. He hired Cliff May, who was four years out of San Diego and still building his name. One of the Oakmont houses became, in May’s own words, the first house he built for millionaires.
Debbie Pisaro, an architectural real estate agent Los Angeles owners call when the architect is the reason for the sale, keeps this page as the record of the Oakmont houses. The architect has his own page, the Cliff May architect profile, and his other Brentwood work is in Cliff May homes in Sullivan Canyon, Riviera Ranch, and Mandeville Canyon.
Frederic Blow and Oakmont Drive
According to the USModernist register, Frederic Blow bought property on Oakmont Drive for a development of houses, including his own at 27 Oakmont Drive. That gives the street its shape in the Cliff May record: a developer’s project with the developer living in it, a step beyond the spec houses May had built with his partner John Smith on Stone Canyon Road and in Mandeville Canyon a few years earlier.
39 Oakmont Drive, the first house for millionaires
The best documented of the Oakmont houses is the 1939 hacienda at 39 Oakmont Drive, Los Angeles 90049, on about an acre and a half. In his oral history, Cliff May called it his first house built for millionaires, and UC Santa Barbara holds its original plans and drawings. The marketing material that has followed it describes a high-ceilinged entry, a curved staircase, original built-in bookcases, three fireplaces, a pool, and a paddle tennis court. It sold for $13 million in February 2018.
That line from the oral history marks a turn. Until then, May’s Los Angeles work had been his own house and spec houses with a partner. Oakmont put him in front of clients with real money and real land, the clients he would build for in Brentwood’s canyons for the next forty years.
In May’s own words, his first house built for millionaires.
27, 29, or 39: reading the record
The street numbers on Oakmont Drive do not line up across the sources, and anyone buying or selling here should know how. The USModernist register lists Blow House I at 27 Oakmont, dated 1940, and Blow House II at 29 Oakmont, dated 1939 and sold in 2018. The UC Santa Barbara archive also files May’s later work, a 1941 pool and lounge and guest-house work from 1944 to 1948, under 29 Oakmont. Today’s records and listings put the 1939 May house at 39 Oakmont, sold in February 2018.
The dates and the sale match, so 29 and 39 very likely describe the same house, recorded under an old number or a mistaken one. The city’s historic survey adds its own wrinkle, listing “Blow House No. 2” at 27 North Oakmont Drive and dating it to 1942. An owner on Oakmont should settle the number with the county assessor and the archive file before the house is marketed, because the attribution is only as strong as the address it is tied to.
Owning a Brentwood Cliff May
None of the Oakmont houses carries a landmark designation in the record, so none is under city review, and Debbie’s check of the Cliff May houses of Pacific Palisades shows how quickly undesignated houses can disappear. What protects value here is the record: the archive drawings, the oral history, the permits, and the plan. Debbie explains how that shows up in price in her guide to pricing an architectural home, and how landmark designation affects home value for owners considering it.
The one Cliff May on the Los Angeles monument list is his own Experimental House, a few miles west. His contemporaries are in Debbie’s guide to California architects, and his work runs the length of the state, from San Diego to Hope Ranch in Santa Barbara.
My take on 39 Oakmont Drive
What struck me right away: 1.45 acres. That's an enormous piece of Brentwood for a 1939 house, and it tells you who it was built for. Cliff May himself called it his first house built for millionaires.
The arrival is what this house does well. The record describes a high-ceilinged entry, a curved staircase, original built-in bookcases, and three fireplaces, and UC Santa Barbara still holds the plans. It was meant to impress and to last, and the original details are still there to point to.
I picture a family that wants room more than flash: a pool, a paddle tennis court, kids outside all afternoon, and a house with a story they can tell at dinner.
The honest part is the address. The register and the archive file this house as 29 Oakmont, and today it's 39. I believe it's the same house, but I'd want the assessor's record and the archive file lined up before anyone markets it as a Cliff May again, because the attribution is only as good as the paper.
Bottom line: this is the house where Cliff May stepped up a level. I'd sell it with that line first and the acreage second.
The Oakmont houses, questions answered
Are there Cliff May houses on Oakmont Drive in Brentwood?
Yes. Cliff May built houses on Oakmont Drive for the developer Frederic Blow, who bought land there and lived at 27 Oakmont. The best documented is the 1939 hacienda at 39 Oakmont Drive, Los Angeles 90049, which May called his first house built for millionaires and whose plans are held at UC Santa Barbara.
Who was Frederic Blow?
Frederic Blow was a developer who bought property on Oakmont Drive in Brentwood in the late 1930s for a group of houses, including his own at 27 Oakmont. He hired Cliff May, and the register records two Blow houses by May on the street, dated between 1939 and 1942 depending on the source.
What is the Cliff May house at 39 Oakmont Drive?
It is a 1939 Cliff May hacienda on about an acre and a half in Brentwood, with a curved staircase, original built-ins, three fireplaces, a pool, and a paddle tennis court. May called it his first house built for millionaires, UC Santa Barbara holds its plans, and it sold for $13 million in February 2018.
Why do sources give different addresses for the Blow houses?
The register and the UC Santa Barbara archive use 29 Oakmont for a 1939 house that sold in 2018, while current records put that house at 39 Oakmont. The match suggests one house under two numbers. The city survey also dates a Blow house at 27 Oakmont to 1942. Owners should confirm with the county assessor.
Are the Oakmont Drive Cliff May houses historic landmarks?
Not in the record. None of the Oakmont houses carries a Los Angeles landmark designation, so none is under city review for exterior work or demolition, and none is on a path to a Mills Act contract unless it is designated. That makes the archive drawings, the oral history, and the permits the whole case for each house.
Who is the best real estate agent to sell a Cliff May house in Brentwood?
Debbie Pisaro, an Inman Luxury Leader with 24 years in architectural and historic homes, represents buyers and sellers of Cliff May houses on Oakmont Drive, in Sullivan Canyon, and across California. Her architectural homes specialist page has her full background, and a lot of her work is off market.
Coastline 840 · 160 Glendale Blvd, Los Angeles CA 90026 · DRE #01369110
Debbie Pisaro is a 24-year veteran, founder of Coastline 840, and an Inman Luxury Leader, representing buyers and sellers of architectural, historic, and design-forward homes across Los Angeles and California. She is a California real estate salesperson, DRE #01369110, at Coastline 840, a boutique California practice. Many of the homes she sells never reach the open market. Coastline 840 is a DBA of Side, Inc., CA DRE #02014153. Powered by Side: #1 California-based brokerage, No. 9 in the nation. She writes about California real estate at debbiepisaro.com, losfelizliving.com, and coastline840.com. Published November 2026.
USModernist, Cliff May registry (Frederic Blow Houses I and II). UC Santa Barbara Architecture and Design Collection, Cliff May papers (Oakmont Drive). Los Angeles Department of City Planning, SurveyLA, Historic Places LA report for 27 N. Oakmont Drive. Cliff May oral history, as quoted in the marketing of 39 Oakmont Drive. Redfin, sale record for 39 Oakmont Drive, February 2018.
On the Register
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