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Cheryle Harris is a pioneer — an unwitting one perhaps, but a pioneer nonetheless.

Last year, Harris decided to sell her three-flat apartment building in south suburban Riverdale and move to the city. She wanted to come back to the city because Harris, like a lot of the other people, prefers city life. She also wanted to be closer to her job.

But unlike many other home buyers, Harris didn’t look for a loft or condo in one of Chicago’s trendy near north or near south neighborhoods. Instead, Harris bought a new single-family home in Woodlawn, a community on Chicago’s South Side with a somewhat shaky reputation.

“I love this house,” said Harris, “Everyone here is concerned about their home. I love the community.”

Harris’ home is one of 45 new residences in the Kenwood Pointe development at 6400 S. Kenwood Ave., built on the same block that in the 1960s was occupied by the Blackstone Rangers street gang.

Harris represents the first wave of middle-class settlers in a movement to change Woodlawn from a community of last resort into a community of choice. And if local organizers have their way, more trailblazers like Harris will buy houses in Woodlawn.

“We want people to choose to live in Woodlawn,” said Leon Finney Jr., who heads The Woodlawn Organization, a grass roots community group spearheading the development of new houses in the neighborhood.

So far, about 60 new homes for middle-income families have been built in Woodlawn. Plans are under way for even more.

This spring, construction will begin on 200 new single-family homes on 63rd Street, previously dotted with vacant lots, shabby commercial buildings and an aging elevated track. The houses are earmarked chiefly for middle-income home buyers.

“We want this community open to all races, ethnic groups and economic classes,” said Finney. “The future of any community is directly tied to its ability to build houses and stimulate homeownership.”

Bounded by Lake Michigan at Jackson Park, Cottage Grove Avenue, 59th and 67th Streets, Woodlawn in recent years has been regarded as a community that didn’t have much of a future, at least not with the middle class.

For years, it has been notorious for its gangs and drug dealers, empty buildings and high crime rates. Woodlawn was a place for the poor and the disadvantaged.

The population of the community has fallen to an estimate 23,508 in 1998 from 36,323 in 1980. The 1998 median family income in the neighborhood was $17,822. Statistics from 1995 showed the area had about double the number of reported crimes as the state average, 114 per 1,000 residents versus 56 per 1,000 across Illinois.

The 1998 city statistics show the neighborhood posting 107 crimes per 1,000 residents, ahead of the citywide average of 91.

Problems aside, Woodlawn was never a community without hope.

Much of that hope has come from The Woodlawn Organization, a 40-year-old group whose roots go back to the activist days of the early 1960s. It was then that labor leader Saul Alinsky put together a group of religious and block club leaders to form The Woodlawn Organization.

From the outset, the philosophy of the group was to mobilize local citizens in order to improve conditions in the neighborhood.

“A resident would look out his window and wonder why a pothole wasn’t fixed,” said Finney, illustrating the kinds of basic services the group fought for.

Over the years, The Woodlawn Organization grew. Today the group, along with its affiliate Woodlawn Community Development Corp., has a staff of 157. The organization provides a wide range of social services to local residents, such as family counseling, day care and help with substance abuse problems.

The Woodlawn Organization is also in the real estate business. During its first 30 years, the group focused on building or rehabbing rental housing, primarily for low-income residents. New for-sale homes were hard to finance because lenders didn’t think property in Woodlawn was a good investment.

“We built about 120 units of rental housing a year,” said Finney, who has worked at The Woodlawn Organization for 34 years. “Anything we built had to be subsidized by the government.”

Because of its historical emphasis on rental housing, The Woodlawn Organization today manages 5,491 apartments throughout the city. Most of those units are low-income subsidized apartments, some of which are owned by the Chicago Housing Authority. About 1,000 of the units are in Woodlawn.

Finney said The Woodlawn Organization has no intention of abandoning its low-income apartments. But, he added, the group won’t ignore the development of new homes either.

“We need middle-income families,” Finney said.

Finney believes the community will thrive only if it has a mix of residents with a mix of incomes.

“The community cannot survive solely with low-income residents,” he said.

Woodlawn has several big advantages, urban planners say. It borders the south edge of Hyde Park, a prosperous and well-educated community dominated by the University of Chicago, which also wants to improve the area. Woodlawn adjoins the lakefront and the neighborhood isn’t far from downtown — attractive features to potential home buyers.

The improvements in Woodlawn come at a time when the South Side of Chicago, in general, is being revitalized. For instance, on the east side of the neighborhood plans have been announced to upgrade Jackson Park and expand La Rabida Hospital. And to the south, the land formerly occupied by the South Works steel mill along the lake is being redeveloped for industry and potentially homes.

Obviously, some home buyers have already recognized the merits of Woodlawn.

Between 1995 and 1998, about 60 for-sale homes were developed in the community. All the houses have been sold and are currently occupied.

“Nobody believed people would buy houses here for $150,000,” said Arthur M. Brazier, chairman of the Woodlawn Preservation and Investment Corp., an affiliate of The Woodlawn Organization that also develops houses. “We have been far more successful than anyone dreamed we could have been 10 years ago.”

In 1995, first-time buyer Cassandra White moved into a new single-family home in Woodlawn. She paid $170,000 for the two-bedroom house, one of eight homes on a gated street.

“I wanted privacy and a secure neighborhood,” said White, whose house was recently appraised for $232,000.

White has seen a lot of changes on the blocks that surround her home since she moved there almost five years ago.

“The buildings on 62nd Street got cleaned up. I’m hoping to see even more improvement with the changes being made on 63rd,” she said.

On 63rd Street, The Woodlawn Organization plans to transform a run-down, 10-block commercial strip into a new residential community. Upon completion, the street will have several hundred new homes, mostly for middle-income buyers.

This spring, the city begins an $8 million upgrade of 63rd Street, with new sidewalks, light poles, curbs and landscaping. Eventually, The Woodlawn Organization would also like to build new schools, a library and health care facilities along the arterial street.

The Homes at Blackstone will be the first houses built on the street. Located at 63rd Street and Blackstone Avenue, the townhouses range in price from $225,000 to $269,000. Eight of the 13 homes have already been purchased. The second phase of the project will have 22 houses.

Victor Cacciatore, chairman of Lakeside Bank and a real estate developer himself, believes the Blackstone project can work. Cacciatore says he was one of the first private developers to build market-rate homes across the street from a CHA housing project near the University of Illinois at Chicago campus.

“People thought I was crazy,” he said.

But the success of that project 15 years ago convinced Cacciatore that Woodlawn was a good place to invest now. As a result, Lakeside Bank has provided a $1.3 million loan to The Woodlawn Organization for the construction of the Homes at Blackstone.

“The renaissance of Chicago marches on,” he said.

Allison S. Davis, a developer and Finney’s boyhood friend, will build 140 for-sale single-family homes on 63rd, between Kenwood and Ingleside Avenues. Construction of the new development, Woodlawn Park, should begin next month.

About 20 percent of the homes are earmarked for lower-income families and will sell for $99,000. The other homes are meant for middle-income home buyers. Home prices start at $185,000, though some of the homes cost as much as $345,000.

Woodlawn Park has five home designs, ranging from a house with 1,450 square feet to a duplex-style house with 3,200 square feet. Lot sizes at Woodlawn Park are 40-by-140 feet, larger than traditional city lots.

“The lot sizes are great. There are no comparable ones this size in the city,” said Davis, who heads the Chicago-based Davis Group. “It’s a great location. People will not recognize 63rd Street when the redevelopment is completed.”

Davis plans to pull residents from the nearby University of Chicago.

“We hope the staff there will be buyers in this project,” he said.

Proximity to the University of Chicago is a big plus for the neighborhood. Communities in transition that can draw support, and often residents, from a university have a good shot at remaking themselves, urban planners say.

“The redevelopment of Woodlawn has really been accelerating over the last five years,” said Hank Webber, vice president for community affairs at the University of Chicago. “The redevelopment of 63rd Street with market-rate housing has the potential to be transformative.”

Webber noted that university employees are already settling in Woodlawn as new houses are built there and old ones are rehabbed. The university encourages employees to buy homes in the area by offering a special mortgage program and low-interest loans to help cover the down payment and closing costs.

Community organizers are quick to point out that Woodlawn is not “gentrifying,” a word that often alarms long-time residents of poor neighborhoods who feel they might be displaced by richer counterparts.

“We are not giving up on low-income housing,” said Finney of The Woodlawn Organization. “We want 60 percent middle-income and 40 percent low-income residents. We don’t have to throw anybody out.”

But Woodlawn will need more than houses to attract middle-income home buyers, who also want good schools and a decent place to buy groceries.

“Schools anchor a neighborhood,” said Bill Hudnut, former mayor of Indianapolis and currently a senior resident fellow at the Urban Land Institute, Washington, D.C. Hudnut believes city schools must be competitive with suburban schools in order for a neighborhood to become one of “choice.”

Community organizers argue that local public schools have improved. They also say Woodlawn schools have gotten a big boost from programs provided by the University of Chicago.

For instance, neighborhood high school students attend special classes at the university in order to prepare them for college. About 100 university students currently work as teaching assistants in seven Woodlawn public schools. The university also has designed a literacy program for two Woodlawn elementary schools.

Schools weren’t much of a concern for home buyer Harris when she picked Woodlawn. Her nephew, who lives with her, attends the local public high school. Harris thinks it’s a good one.

Harris’s big problem is finding a good place to shop.

“I’d like to see more retail development in the neighborhood,” she said. “It would be nice to have a new grocery store nearby.”

With new houses being built on 63rd Street, Harris believes more retailers will want to open stores in Woodlawn.

“Retail is lagging,” said developer Davis. “We’d like to have the corner of 63rd and Cottage Grove become a major shopping area. We hope to attract a new supermarket and drug store.”

Finney believes construction of new houses will stimulate more commercial interest in the neighborhood.

“Add it up. We’re investing about $57.1 million in housing,” said Finney. He’s confident retailers will see the logic of a Woodlawn location, just like the pioneer home buyers.