In 2003, when Jack Walker acquired the land where a local developer is planning to build new homes, most people said he was crazy. 

Later this year, the 24 acres off Southeast Loop 410 and Roosevelt Avenue will start to take the shape of a new Southside residential neighborhood in an area where the number of retailers, restaurants, major employers, and other institutions has grown in recent years.

“I consider myself an entrepreneur,” said Walker, a landowner and real estate developer. “As such, my job as an entrepreneur is to see things that other people don’t see.”

What he saw 18 years ago was an area other investors “looked down upon,” he said, “But at the same time, as you drove around the area, you saw nice cars, and you saw well-kept homes, and that said to me, these people are being underserved.” 

Shortly after, Toyota opened a plant in South San Antonio, and Texas A&M San Antonio decided to put its campus on the South Side. TJX Companies built a 1.7 million-square-foot distribution center. In 2009, the City designated the 5.8-mile Roosevelt Corridor for improvements that would spur economic development.

Confident there would be demand for developable land, the former chief financial officer for a supermarket group quietly assembled 120 acres, one acre at a time. In most cases, the land already was zoned for commercial development or he had it rezoned. 

The 24 acres of land slated to become a housing development is adjacent to a small strip mall and a Valero gas station overlooking Southeast loop 410.
The 24 acres of land slated to become a housing development are adjacent to a small strip mall and a Valero gas station overlooking Southeast Loop 410. Credit: Bria Woods / San Antonio Report

Walker sold the first corner parcel to Valero for a gas station, then built a retail strip center. In 2016, he sold 25 acres to residential builder KB Home for the Loma Mesa development and, a year later, another 25 acres to H-E-B, which was expected to start building in 2020.

Laddie Denton, CEO and co-founder of residential and commercial developer Bitterblue, also saw value in the area. “We consider the South Side to be a very viable market and a significant part of our development portfolio,” he said. 

The project team of Bitterblue, Walker, and Pape-Dawson Engineers will break ground on the Roosevelt Heights development in late summer or fall, the plans having moved a step closer to reality in April when the board of the Mission Drive-In Tax Increment Reinvestment Zone approved a grant agreement that will reimburse Bitterblue up to $4 million for infrastructure costs. 

City Council approved the reimbursement this month. “We’re very excited because we know that we do need more new housing stock in the southern sector,” said District 3 Councilwoman Rebecca Viagran.

A homebuilder hasn’t been identified, Denton said, but the target price for homes in Roosevelt Heights will be in the low- to mid-$200,000s, with 54 homes available to households making up to 120% of the area median income ($52,455). Plans call for a neighborhood park and recreation area. 

Survey work has already begun, and construction is expected to be complete in late 2026. 

Walker said he’s in talks with various commercial developers that will bring to the area Burger King, Taco Bell, and KFC restaurants, an auto parts store, and a rehabilitation hospital. In March, the Harlandale Independent School District sold a sizable parcel adjacent Roosevelt Heights to KB Home. 

“Five years from now you will see all the retail [properties] sold and most of this built out, which is the developer’s dream to be able to see the buildings rising from the dirt and people enjoying their facilities,” Walker said.

He does not know when H-E-B will follow through on building a store at the intersection, plans that were delayed by the pandemic in 2020, but expects it to happen.

“When you imagine the thousands of new homes that are going to be built, it’s a must because their stores up on our Military [Highway] are already too busy,” Walker said. 

Despite the potential growth, Walker is not planning additional land purchases on the South Side.

“I think the land prices already outstripped me, and I think I want to be somewhere between San Antonio and Austin because it’s going to be like Phoenix and Scottsdale or Denver and Boulder,” Walker said. “Those areas are destined to expand in the future.”

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Shari Biediger

Shari Biediger is the development beat reporter for the San Antonio Report.