Homes stand in the distance on Winterhill and Plainview Avenues, as seen from Wenzell Avenue in Beechview, in 1913.
That's Brookline Boulevard (now Bodkin Street) going uphill to the right from West Liberty Avenue to Pioneer Avenue.

A great place to view vintage photos of Pittsburgh and it's many communities is through the University of Pittsburgh online digital archive. There are over 300 photos of Brookline, and most of them have been used on this website. There is also a zoom feature, which allows a more detailed glimpse of different locations in each photo. Shown here are the zoom-ins of images already posted on the Brookline Connection. One master photo can be made into multiple separate images. Shown here are the pictures within the pictures.

Residential development began to take hold in Brookline in the early 1900s. The first housing plans were the Fleming Place Plan, the Hughey Farms Plan and the Paul Place Plan. By the 1920s the neighborhood had grown considerably, and the need for better infrastructure and roads led the city to embark upon a massive project to upgrade it's outlying communities. Many of these photos show Brookline streets during this modernization effort. The photos give a good glimpse into what residential life was like in the early years of the 20th century.

Click on images for larger pictures

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Gallion Avenue

  
A view of Gallion between Pioneer and Beaufort Avenues (left), and a home at the corner of Gallion and Beaufort, in 1916.
The children to the left are standing in the Brookline Elementary School garden.

  
Beaufort Avenue rising from Gallion towards Berwin (left), and a home on the corner of Beaufort and Gallion, in 1916.

  
A Gallion Avenue home at the bottom of Wedgemere Avenue, and the walkway, "The Short Cut," that goes through
to Berwin Avenue (left), and a view of Gallion Avenue (to the right), as seen from Rossmore Avenue, in 1925.

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Glenarm Avenue

  
A two-car garage along Glenarm and the home at the corner of Berwin Avenue (left), and a view
of homes along Glenarm Avenue, across from the Berwin Avenue intersection, in 1930.

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Jillson Avenue

  
A view of Jillson Avenue and other streets in the Fleming Place Plan, as seen from Vodelli Street in Beechview,
in 1921 (left), and a view of homes at the corner of Jillson and Shawhan Avenue (right) in 1935.

  
Homes along Jillson Avenue in 1935.

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Kenilworth Avenue

  
Homes along Kenilworth Avenue, both inside the Boulevard Loop (left), and outside the loop (right), in 1935.
When the Boulevard was rerouted onto the trolley loop, Kenilworth Avenue was cut in two.
There is also third section of Kenilworth Avenue along Pioneer Avenue.

Some Kenilworth Avenue homes inside the Boulevard Loop, off of Jillson Avenue, in 1915.

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Lineal Avenue

  
Homes along Lineal Avenue, near Timberland Avenue, in 1909.

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Oakridge Street

  
The backyard of a Creedmoor Avenue home, as seen from Oakridge Street (left), and a view
looking uphill towards the intersection with Creedmoor Avenue, in 1919.

  
A manhole cover at the Oakridge/Chelton intersection (left), and a view of Oakridge Street
between Chelton Avenue and Creedmoor Avenue, in 1919.

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Pioneer Avenue

  
Train cars on the loading platform at the lower end of Pioneer Avenue in 1915.

  
Walking board sidewalks were commonplace along Pioneer Avenue in 1916.

  
Homes across from the Woodbourne Avenue intersection (left), and the home at the corner of Woodbourne, in 1916.

  
Homes across from the Berkshire Avenue intersection (left), and the home at the corner of Berkshire, in 1916.

  
A Pioneer Avenue home (left), and a view of the roadway between Kenilworth Avenue and Dorchester Avenue, in 1916.

  
Views from Kenilworth Avenue showing the McNeilly Road intersection (left), and the condition of the roadway between
Kenilworth and Waddington, in 1916. St. Pius parish church and BRC school are today located where the trees stand.

  
The walkway between Berkshire and Woodbourne in 1916 (left), and a home at the lower end of Pioneer Avenue in 1924.

  
A mailbox hangs on a telephone pole near Fordham Avenue in 1921 (left), and a view from Ray Avenue looking
towards Metz Way in 1924. The square building on the left is Pioneer Avenue's Little Store.

  
The Lang home on the lower end of Pioneer Avenue, near the present-day intersection with Cadet Avenue (left), and a
view towards Capital Avenue and Dunster Street, in 1924. The Lang's were prominent landowners in the early
days and owned much of the land along lower Pioneer Avenue, which was once called Lang Avenue.

Pioneer Avenue between Gayly Way and Bellbrook Avenue, near the automobile, in 1924.

  
Looking from Chrylser Avenue towards Dunster Street (left), and a home near the Ray Avenue steps, in 1924.

  
A view from Ray Avenue towards Dabney Way (left), and homes between Gayly Way and Bellbrook Avenue, in 1924.

  
A view from Gayly Way towards Bellbrook Avenue (left), and a train car at the loading platform on lower Pioneer, in 1924.
The home on the hillside is the Miller homestead, located along Richter Street on the other side of the tracks.

  
A view of lower Pioneer Avenue (left), and a Marion steam shovel of the Booth and Flinn Company, in 1924.

  
A home near Capital Avenue (left), and a truck making it's way down lower Pioneer Avenue, in 1924.

  
A view of the lumber yard next to the Sauter Place homes below Pioneer Avenue (left), and the Miller homestead,
located near the lower end of Pioneer along Richter Street on the other side of the P&WVRR train tracks. The
lumber yard and Sauter Place homes stand on the present-day location of the Matthews Bronze complex.

Pioneer Avenue homes across from the intersection with Rossmore Avenue in 1925.

  
The Miller homestead on Richter Street, on the other side of the railroad tracks at the lower end of
Pioneer Avenue (left), and the busy intersection of Pioneer and Brookline Boulevard, in 1924.

  
The Hunter estate at the intersection of Brookline Boulevard and Pioneer (left), and a view from the boulevard to
Woodbourne Avenue, in 1935. Brookline Elementary School can be seen in the photo on the right. The Hunter
family were prominent landowners in the early days. Bodkin Street was once known as Hunter Avenue.

  
Women wait to cross Brookline Boulevard at Pioneer (left), and homes near the Jillson Avenue intersection, in 1935.

A view of Pioneer Avenue, near the intersection with Brookline Boulevard, in June 1936.

  
Cars parked in the Moore Park lot (left) and a roller on the field that will soon be the site of the playground, in 1938.
Moore Park was built between 1938 and 1940 by the Works Project Administration, which was one of
President Franklin Roosevelt's New Deal initiatives. The WPA built several parks in Pittsburgh.

A view of West Liberty Elementary School and homes along Pioneer, Plainview and Woodward Avenues,
as seen from Shiras Avenue in Beechview, in 1921.

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Queensboro Avenue

  
Homes along Queensboro Avenue, between Bayridge Avenue and Woodbourne Avenue, in 1924.

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Rossmore Avenue

  
Homes between Wedgemere Avenue and Flatbush Avenue (left), and a tree growing in the middle of the road, in 1925.

  
Rossmore Avenue as seen from Flatbush Avenue (left), and a home between Pioneer and Wedgemere Avenue, in 1925.

  
Homes near the intersection with Pioneer Avenue (left), and Glenarm Avenue (right), in 1925.

Homes along Rossmore Avenue, near the intersection with Wedgemere Avenue, in 1925.

  
Homes at the intersection with Wedgemere Avenue (left), and a view from Wedgemere towards Pioneer Avenue, in 1925.

  
A view of Rossmore Avenue, as seen from Flatbush Avenue (left) and Pioneer Avenue (right), in 1925.

  
Homes along each side of Rossmore Avenue, near the intersection with Flatbush Avenue, in 1925.

A Pontiac GTO convertible parked along the 800 block of Rossmore Avenue in 1967.

  
Homes near Rossmore Avenue in 1925. I haven't been able to pinpoint their location.

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Shawhan Avenue

  
The home at the corner of Jillson and Shawhan Avenues (left), and other Shawhan Avenue homes, in 1935.

  
Homes along Shawhan Avenue in 1935. Pioneer Avenue homes are also visible in the photo on the left.

A view of Shawhan Avenue homes, and Brookline Elementary School, as seen from Vodelli Street in Beechview, in 1913.
The homes and streets in this photo make up the Fleming Place Plan, one of the first housing developments in Brookline.

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Templeton Avenue

A view of new homes along Templeton Avenue, and the Hughey estate, as seen from Wenzell Avenue in Beechview, in 1913.

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Timberland Avenue

  
Homes on Timberland Avenue, along Saw Mill Run, in 1909, behind the present-day Red, White and Blue Thrift Store.

  
A wagon along Timberland Avenue (left), and homes next to the Timberland Bridge, in 1909. The bridge connected
Timberland Avenue with homes along Cadet and Lineal Avenues on the other side of the train tracks.

  
The Timberland Avenue Bridge and the road leading down towards Saw Mill Run in 1909.

  
A home along Timberland Avenue (left), and the attached family dairy buildings (right), in 1909.

  
A field close to Timberland Avenue, along Saw Mill Run (left), and the Timberland Avenue Bridge, in 1909. The photo
on the right shows the Saw Mill Run valley, the dirt roadway and the Pittsburgh and Castle Shannon Railroad line.

  
The P&WVRR tracks pass under the Timberland Avenue Bridge in 1918 (left), and Timberland Avenue homes in 1925.

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Wedgemere Avenue

  
Kids playing along Wedgemere Avenue (left), and a view of the Rossmore Avenue intersection, in 1925.

  
Front porches of homes along Wedgemere Avenue in 1925.

  
Homes along Wedgemere between Rossmore and Gallion (left), and the intersection of Wedgemere and Rossmore, in 1925.

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Wenzell Avenue

  
A view of Wenzell Avenue, as seen from Pioneer Avenue (left), and the Kerr family mansion near West Liberty, in 1909.

  
The intersection of West Liberty Avenue and Wenzell in 1913 (left), and a wagon of the
South Hills Ice Company being repaired at Kerr's Wagon Repair shop, in 1915.

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Whited Street

This is the home at 2306 Whited Street, the third house up from Marloff Place. Shown here in 1941, the house
was constructed in 1939. It was the first home built along this section of Whited. The plot of land
was purchased from the Marloff family, who owned the farm house in the distance to the right.
Other homes followed as the Marloffs sold off lots for development.

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Winterhill Avenue

Homes at the corner of Winterhill Avenue and Pioneer Avenue in 1935.

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Woodbourne Avenue

  
Homes along Woodbourne Avenue, as seen from Brookline Boulevard (from present-day Gordon's Bar), in 1916.

  
A view from Sussex Avenue towards Queensboro Avenue (left), and Woodbourne Avenue homes near Sussex, in 1924.

  
Homes along Woodbourne Avenue near Oakridge Street (left), and a view from Sussex to Oakridge, in 1924.

  
An automobile parked across from Freedom Avenue (left), and a view of Woodbourne from Sussex to Pioneer, in 1924.

A view of Woodbourne Avenue, from the intersection with Freedom Avenue looking towards Oakridge Avenue, in 1924.

  
Homes along Woodbourne Avenue, near the intersection with Oakridge Street in 1924.

  
Homes along Woodbourne Avenue, between Freedom Avenue and Oakridge Street, in 1924.

  
Homes along Woodbourne Avenue, near the intersection with Cedric Avenue (left) and Oakridge Street (right), in 1924.

  
The intersection of Woodbourne and Queensboro Avenue (left), and homes between Sussex and Queensboro, in 1924.

  
Road conditions along Woodbourne Avenue in 1924. A sewer line had been run and the street would soon be paved in brick.

A family in their horse and buggey approach the intersection with Sussex Avenue in 1924.

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Woodward Avenue

  
A street sign stands at the intersection of Woodward Avenue and Brookline Boulevard (Bodkin Street) in 1909 (left),
and homes along Woodward Avenue, as seen from West Liberty Avenue at Stetson Street, in 1912.

  
Homes along Woodward Avenue, as seen from Saranac Avenue in Beechview, in 1921 (left) and 1922.

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In the late 1800s and early 1900s, Brookline had mining operations scattered throughout the valleys. There were several
mines along Edgebrook, McNeilly (Elwynn) and Saw Mill Run. This could be a a mine along Elwynn Street, shown in 1910.