South Boston
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The South Boston peninsula is composed of several distinct sections, including the historic warehouses of Fort Point, the luxury towers of the Seaport, the West Side (including Andrew Square and the Polish Triangle), and the beach neighborhoods of the East Side (City Point and Dorchester Heights/Telegraph Hill).

The neighborhood has seen a remarkable and ongoing transformation, from "Southie" to "South Boston." The gritty neighborhood from Good Will Hunting, the former home of Irish mobster Whitey Bulger, and the opposition to de-segregating public schools in the 1970s has become a more affluent and diverse neighborhood. Today, South Boston is a patchwork of charming historic houses, former factories converted into lofts, and new luxury condo developments. But more than just the residences, it is the lifestyle – more restaurants and cafes, and the Lawn on D, as well as the Children’s Museum and the Institute of Contemporary Art.

(As an aside, in 1827 Edgar Allan Poe briefly served as a soldier at Fort Independence on Castle Island, which inspired the story of The Cask of Amontillado).

Beach neighborhood. South Boston is one of the beach neighborhoods of Greater Boston, with three miles of beaches (Carson Beach, M Street Beach, and Pleasure Bay) and parkland along Dorchester Bay.

Considerable parks and recreation. The neighborhood contains Castle Island, Marine Park, and the Strandway, part of Frederick Law Olmsted's 'Emerald Necklace' of parks. For runners, the Loop (formally known as the Head Island Causeway, but no one calls it that) ... And there are four yacht clubs built in 1899 along William Day Blvd: South Boston Yacht Club, Columbia Yacht Club, Puritan Canoe Club and The Boston Harbor Yacht Club).

Airport noise. The waterfront of South Boston is just half a mile across the water from East Boston's Logan Airport. As a result, it is one of the neighborhoods affected by airport noise issues.

A building boom from 1825 to 1860 has given much of South Boston its historic character. The dominant housing types include two-story wood-frame single-family houses, and after 1860, a mix of brick and frame rowhouses. By 1900, triple decker houses began to predominate.

Contains some of the most expensive real estate in Boston. Within South Boston, the Seaport is one of the most expensive neighborhood of Boston, on a per square foot basis. Although this is in large part because it is all ground-up construction of new, luxury condominiums, so there is not a range of housing types to bring down the average, as there is in historic neighborhoods. Other parts of the neighborhood --- historic, from 1820s-1860s, and triple-deckers from late 1800s and early 1900s.


Westside Within South Boston, Dorchester Street is the generally-accepted dividing line between the Westside and Eastside. The West Side (or “Lower End”) is closest to Financial District and the South End, and is close to two stops on the Red Line, Andrew Station and Broadway.

Andrew Square was originally part of Dorchester, and was previously known as Little Neck and Washington Village. While South Boston overall has changed considerably since 2000, Andrew Square has changed the least and is still regarded as comparatively industrial and gritty. The area is surrounded by several large public housing complexes, including Old Harbour Village, the first public housing in the United States when it was begun in 1936. The area is also affected by from the methadone clinics in the Newmarket section of South Bay. The Andrew Square Civic Association is working to increase diversity and improve quality of life in the neighborhood. That said, the average asking price in Andrew Square ($775/sq.ft. in Feb. 2018) is still higher than that of the Eastside ($688/sq.ft.).

As an aside, a portion of Fort Point was built on land excavated from Andrew Square, and used as infill – and in the process of moving the land from Andrew Square to Fort Point, it became considerably more valuable.

Widett Circle is the industrial western edge of South Boston, and is adjacent to the industrial Newmarket section of South Bay. These areas have been the focus of development interest for years, as they represent a large undeveloped area in the midst of densely-developed and desirable residential neighborhoods.

Polish Triangle is mostly in Dorchester, but a section extends into Andrew Square. The compact neighborhood is bordered by Boston Street, Dorchester Avenue, and Columbia Road. Once a foothold for Polish immigrants, the neighborhood is becoming more diverse, according to Curbed.


The East Side is further from the subway, and includes the beach neighborhoods of City Point and Dorchester Heights/Telegraph Hill.

City Point is the easternmost neighborhood of South Boston. It is surrounded by water, parkland, and beaches, with Castle Island to the north, M Street Beach to the south, Pleasure Bay to the east. Today, the neighborhood seeing considerable transformation through both renovations and new development. The City Point Neighborhood Association works to enhance quality of life for residents.

Dorchester Heights/Telegraph Hill is closer to the Westside. It contains a significant historic district, especially around Thomas Park. The oldest houses here date to the 1830s, and the hillside neighborhood overlooks the Old Harbor and M Street Beach. In 1776, this same elevation made it the site of a key battle in the American Revolution. The John Hawes Bird House (480-482 East 4th), built c.1830, is one of the oldest surviving houses here.

best blocks and notable buildings

The earliest buildings in South Boston date from its annexation in 1804, and these are modest-scale Federal houses. There is an impressive concentration of Greek Revival houses from the 1840s and 1850s. These include clusters on West 4th Street, between E and F; East 4th/C Street/Broadway; and 2nd Street between I and K.

John Hawes House (568 East 5th St.), built in 1805, is the neighborhood's earliest surviving building. It is a significant example of Federal style housing in South Boston.

318-324 E Street are four brick rowhouses with arched, recessed entries, also from the Federal period.

92-94 B Street is a double frame house with period sidelight and transom, also from the Federal period.


The western section of South Boston is well-served by subway options, with Red Line stops at Andrew Square and Broadway. Those in the southern part of the neighborhood, by Andrew Square, are close to the JFK/UMass station for the Red Line and the Commuter Rail.


South Boston is a large neighborhood (over 1,700 acres) with multiple sub-neighborhoods, including Fort Point and the Seaport.

To the north and east is Boston Harbor, and across the water are the Jeffries Point and Logan Airport sections of East Boston. To the west are the South End, Financial District, and Waterfront.
And to the south is Dorchester, specifically the Harbor Point, Polish Triangle, Savin Hill, and South Bay neighborhoods.

South Boston was originally a peninsula of about 579 acres that was once part of Dorchester – which it why it contains a section called Dorchester Heights. Today, it is over 1,300 acres as a result of filling which expanded the original shoreline.

South Boston is one of many Boston neighborhoods that have been expanded using infill. The flat industrial land northeast of First Street was largely created in the late 1800s, and Marine Park was created to link Castle Island to the peninsula. The narrow Fort Point Channel is all that remains of South Boston Bay.

In the 1600s and 1700s, South Boston was primarily rural and was used as pasture. In 1674, James Foster built the first house on the peninsula, and the Blake House was built at City Point in 1680 (since moved to ___________). For most of the 1600s, it remained scattered houses and large farmsteads.

The annexation of South Boston in DATE was a result of real estate speculation on the part of Harrison Gray Otis, Joseph Woodward, and others – the same people who were involved in the Mount Vernon Proprietors, the first real estate development company which developed Beacon Hill.

After acquiring land at Dorchester Neck, the narrow strip of land around today's Andrew Square, Otis and company petitioned the General Court to annex the whole area to Boston. In 1804, over the opposition of the Dorchester residents, the General Court [approved the annexation]. The next year, the South Boston Bridge Proprietors opened the first direct link from the peninsula to Boston, a bridge at the site of today's Dover Street Bridge.

In 1805, a plan for a street grid was established, laying out the blocks from A through Q streets, and First through Eighth streets. South Boston was originally a disappointment to the real estate speculators – by 1825, growth was limited. But it grew rapidly between 1825 and 1861, when the Civil War interrupted residential development but boosted industrial production. Indeed, between 1835 and 1845, land values in South Boston rose 450% as its industrial potential was recognized.

During the 1850's, South Boston was industrially dominated by iron foundries and machine shops. At this time, the South Boston Iron Works was the largest foundry in the country, and the Bay State Iron Company at City Point was
the largest manufacturer of railroad track in New England. Ship yards in South Boston shared the prominence of those in the East Boston, and Harrison Loring's City Point works were in successful operation through the 1890's. The South Boston Gas Works began operation in 1852, and in 1861, the first petroleum refinery in Boston was established as the Stephen Jenney and Company.

Driving the British from Boston had required months of grueling work on the part of colonists in New York and Massachusetts Bay. In November of 1775, Washington had dispatched Bostonian Henry Knox to retrieve badly needed cannon from Fort Ticonderoga, New York. Teamsters with eighty yoke of oxen made the three hundred mile journey, bringing 59 cannon for the colonial army then encircling Boston. Once they neared the city, the rebels faced a new challenge. How would they roll the guns into place without tipping their hand to the British? On the night of March 4, 1776, colonial militia and local volunteers stealthily fortified the summit of Dorchester Heights.

Wrapping their wagon wheels with straw to deaden the sound, they moved the cannon from Roxbury and entrenched them on these hills south of Boston. British General Howe planned an attack, but a violent storm prevented his soldiers from landing. Within a few days, Howe, his troops, and a thousand colonial loyalists set sail for Nova Scotia, abandoning the city to Washington's forces and its jubilant citizens. The army improved the fortifications and again stationed troops on Dorchester Heights during the War of 1812. After 1814, however, the twin hills declined in military importance.

Since Boston had annexed Dorchester Neck in 1804, developers eyed the Heights as a source of raw material for the expanding city. During the second half of the nineteenth century the hills of South Boston underwent the same excavation that lowered Mount Vernon and Pemberton and Beacon Hills, the "tri-mountains" of the Boston peninsula. In 1898, the General Court of Massachusetts commissioned a monument to stand on the remaining hill of the Heights. Designed by the architectural firm of Peabody and Stearns, the white marble Georgian revival tower commemorates the 1776 victory. In 1966 the Heritage Conservation and Recreation Service added Dorchester Heights to the National Register of Historic Places. Twelve years later the National Parks and Recreation Act authorized the City of Boston to transfer the site to the National Park Service. At that time, it joined the eight other sites which comprise Boston National Historical Park, established in 1974.

Dorchester Heights adds a valuable dimension to the Park. Its historical significance and the development of the surrounding community vividly reflect the history and growth of the city of Boston. With the fortification of its summit in 1776, Dorchester Heights contributed significantly to one of Boston's major victories and demonstrated the integral connection between the Boston peninsula and her neighboring community. The annexation of Dorchester Neck to Boston in 1804 strengthened that link. Building and landfilling operations cemented the tie by facilitating travel between the two areas.