The South End was Boston's first planned community, built almost entirely on landfill between 1800 and 1850, when dirt was piled on either side of the narrow neck of land leading to the Shawmut peninsula -- modern downtown Boston. The South End's earliest neighborhoods, including Union Park, were inspired by English cities like Bath. During the 19th century, developers built single-family homes as fast as they could to lure the affluent from Beacon Hill. The result was a cozy and dense character that contemporary urban planners have sought to duplicate across the country.

After a period of decline, gentrification began in the South End in the '60s and '70s, with gay men and lesbians, artists and architects leading the way. They fixed up the brownstones off Tremont Street and occupied mothballed manufacturing buildings and old piano factories. Atelier 505, a new condominium complex recently completed on Tremont Street, is testament to the area's continued vitality.

Many of the South End's bow-front rowhouses have come full circle, from single-family homes with servants' quarters, to apartments and rooming houses, to condos, and finally back to single-family townhouses again -- but going for well over $1 million this time around.

The South End is bordered on the North and West by the prestigious Back Bay area which has some of the best shopping as well as some of the most expensive property in the U.S. The technical border runs along the Southwest corridor park, which runs between Columbus Ave., with it's fabulous restaurants and beautiful St. Botolph Street with its lovely brownstone homes. St. Botolph is considered by many to be part of the South End, but is technically in Back Bay.

On the South and West is Massachusetts Avenue, which features Chester Square, with its huge brownstone homes and condominiums with some of the biggest footprints in the city.

On the North and East is Berkeley/East Berkeley St., beyond which is charming Bay Village and the Theater District.

In the late 1840's and early 1850's, the South End was filled in, and construction began on what was then the most upscale area in the city. After the Back Bay was completed, many of the City's elite built new homes there, and the South End became more of a blue collar area with lots of rooming houses.