On Olive Avenue, Lakiba Pittman is here to stay.

As a string of houses to the left and right of hers in Palo Alto's Ventura neighborhood have been bought out by two owners, the decision not to sell has rendered her one of three remaining independent homeowners on the block — as well as the last African-American resident on a street rooted in black history.

"I'm very committed to being able to keep my house and maintain the flavor of the neighborhood," said Pittman, an educator and former member of Palo Alto's Human Relations Commission. "It's based on a connection to the house, and not just the house — but the land and the memories."

Pittman's cozy 800-foot cottage, which is decorated with hanging plants and painted pale yellow, cradles her family's history as one of several African-American families who were able to buy homes in Palo Alto in the face of 1950s housing discrimination. Stretching from Park Boulevard to El Camino Real, part of Olive Avenue overlooks a lengthy parking lot; the building housing Fry's Electronics lies to its rear.

Now, as the city prepares for long-term revitalization of the Ventura area, Pittman and other Olive Avenue residents find themselves in the center of what could be a sweeping redevelopment of the neighborhood.

Longtime residents said that two families have been buying homes on the narrow road for years as people have moved away. According to Santa Clara County records, Boyd C. Smith owns nine of the 18 homes on the street; residents confirmed he is Boyd Smith Sr. of the Ash Street real estate firm WSJ Properties. Another six homes are listed under the name Peter Lockhart, who runs Peter Lockhart Landscape out of 405 Olive Ave.

Smith declined to confirm ownership of the homes or comment for this article, and Lockhart did not respond to repeated requests for comment.

Mike Harrison, whose parents first moved to their Olive Avenue house in the 1940s, said that members of Smith's family first broached the topic of buying his family's home in the 1990s. Harrison ultimately went through with the deal this year.

"Between then and now, they hadn't approached me about it at all," Harrison said. It wasn't until 2015 that Harrison felt ready to consider the offer, so his son followed up with the Smiths.

"(In 2015) I backed out at the last minute," Harrison said. "I got cold feet and decided not to sell until this year."

The street's unique history has kept Pittman from following in Harrison's footsteps. Olive Avenue, she said, provided a community for black residents during the '60s, when the rest of the city did not. Between Grant Avenue and Lambert Avenue — known today as the heart of the Ventura neighborhood — at least seven or eight black families owned homes, in addition to five to seven on Olive Avenue alone.

This contrasted with the widely documented practice of redlining and anti-black property clauses that shunted black families into the area that would later be incorporated as East Palo Alto. Harrison recalled that when his grandfather bought a home on Fife Avenue in the Crescent Park neighborhood in the 1920s, a friend had to transfer the property into his name for a dollar because it was illegal to sell to African-Americans.

"It became an entirely black-owned street, for the most part, anyway," Harrison said. "I think there's only two black families on the street now — but the whole street was black."

Lockhart's and Smith's plans for Olive Avenue, which is mostly populated by one-story homes, are not clear. In a 2010 letter to the city, Lockhart described his hopes for multifamily housing on the street to enhance the "viability" of the California Avenue shopping and create a "cohesive neighborhood," adding that Ash Street could be opened up to Page Mill Road.

"I strongly suggest that Olive Avenue is designated as Multi Family or PC (Planned Community) allowing up to 30 units per acre that is economically viable," the letter reads. "Both the Fry's property and Olive Avenue property would have the potential for much better development footprints."

Whether Lockhart's vision has changed since then remains to be seen. Over the next 18 months, the city will work with various neighborhood stakeholders to draw up a plan for the area stretching from Page Mill to Lambert; Pittman plans to apply to become a member of the working group.

The demographics of residents on the street have completely transformed in the nearly 70 years since Pittman's and Harrison's families bought their homes. Erin O'Donohue, a single mother who rented from the Harrisons from 2014 to 2016, said that the homes are in high demand as renters come and go.

Although she described the Smiths' ownership of the block as a "monopoly," she said she felt welcomed on Olive for the relative affordability of the property. In San Mateo, she had watched her rent go up by 33 percent She added that learning about the street's historic roots from her neighbors was "so impactful."

According to Pittman, the African-American families who lived in the neighborhood formed longstanding friendships. As recently as last year, a "South Palo Alto" reunion brought together residents from that era who are still in touch, though most have since moved to Stockton, Tracy and other areas that are more affordable.

Pittman's grandmother worked as a live-in maid downtown, and her father was a postman for 30 years. Olive Avenue allowed them to build their lives for the next three generations — all the way to Pittman's own grandchildren.

"It was a great accomplishment for my parents to save money for years before they were actually able to buy the house," Pittman said. "From my personal feeling, they worked really hard to get this little house ... so I am here to pass it on."