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Charming Upper East Duplex

Upper East Charmer Near Mission

Address: 20-22 East Los Olivos Street | Status: On the market | Price: $3,250,000 | Credit: Jake Cryan

When I visited this lovely home near the Old Mission last week, I followed the signs and the parade of people. The rose garden was bustling with picnickers, kids chasing dogs, and dogs chasing frisbees. The whole scene felt like one big end-of-summer party. 

Several groups of people were walking in the same direction that I was, and sure enough, they were headed to my very destination: a grand vintage home located at 20 and 22 East Los Olivos Street. 

As I approached, I saw a sign indicating that my friend Michelle was the Realtor hosting the open house. Then, as I got closer, I saw another real estate sign with my friend Jessie’s name on it. Had Michelle borrowed Jessie’s sign? Or vice versa? I love both Jessie and Michelle, so I was looking forward to seeing either of them.

When I got to the appointed address, it turned out that both Jessie and Michelle were hosting this open house. Appropriately so, because this prestigious address showcases two houses in one.

20 and 22 East Los Olivos is a historic home that is actually a legal duplex. It made sense that both Michelle and Jessie were in attendance to shepherd the stream of visitors around the property and show them how the two spaces can function together and separately. 

Built in 1924, the property has a two-bedroom, two-bath home on one side and a larger four-bedroom, two-bath on the other. Both display the resplendent details of its historic era, while also boasting updated systems that provide modern convenience and efficiency.

Photo: Jake Cryan20-22 East Los Olivos Street

A traditional white stucco facade with red-tile roof announces the home’s quintessential Santa Barbara style. Bright bougainvillea spills over the top of a wrought-iron gate, set into a low white wall, and drought-tolerant specimen succulents grace the front entrance, furthering its native pedigree.

Walking up the front steps onto the broad entry patio, wide double doors lead into the living room of the larger 20 East Los Olivos, while a more subtle entry to the left leads into the smaller sibling at 22 East Los Olivos. 

One of the most enchanting elements of this duplex is its adaptability. The two units can function completely separately, or they can be combined into one grand residence. They can also be used in a flexible style: Think parents who visit often, separate but cozy guest accommodations, space for grandkids to come and stay awhile, or any number of reasons to have independent but intimate living situations.

I followed Jessie around the “big house” and then walked through the “small house” with Michelle, all the while imagining how the two sides could be used in tandem. 

The four-bedroom, two-bath side has a huge living room with a brick-fronted fireplace and double doors that lead out onto a sweeping terrace that runs the length of the house. This is one of the many features that blends the two homes and brings the outdoors in, or vice versa: letting the living space spill outside in perfect Santa Barbara fashion.

A kitchen/dining room combo is bridged by arched doorways and unified by gleaming hardwood floors that continue throughout. The kitchen has been modernized with quality cabinets and high-end appliances. One bedroom downstairs and three bedrooms above are graced by larger-than-expected closets and storage space, plus a balcony and sitting area upstairs that lend flexible options.

The left side of the house boasts two bedrooms and two full baths, one up and one down. Although it is the more modest half of the duplex, it still enjoys luxurious details throughout. The downstairs bedroom opens through French doors to also enjoy the backyard terrace.

This tiled back deck ​— ​accessible from several rooms on both sides ​— ​is part of what enables the home to function as two distinct abodes or be combined into one. It overlooks a lovely private backyard with a broad expanse of lawn that feels like a secret oasis in the middle of its neighborhood. A detached three-car garage sits in the far corner of the property, offering additional options.

This flexible duplex in the heart of the upper Eastside is poised for personalization. I walked through it feeling like it could easily be wrapped up into one large family compound, while many house-hunters will see extreme value in keeping it as two separate units.

However it gets situated and used by its next lucky owners, this home’s lovely location and splendid style offers the perfect Santa Barbara experience. Fortunately, I had both Jessie and Michelle there to help me see its options as single living or dual, and its treasured details both inside and out.


20-22 East Los Olivos Street is currently for sale in Santa Barbara, listed by Angela Moloney of Berkshire Hathaway HomeServices California Properties. Reach Angela at 451-1553 or
angelamoloney@bhhscal.com. For more information and photos, visit angelamoloney.com.

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