No. 11110 Bailey Street School, photograph published in 1902 School Dept report. The city acquired the houble house on the right in December 1898. The property at the left, 63 Bailey Street, became a VFW post, and the property at the now has a one-story brick former school house, owned and used by Mental Programs as housing for transitional residents.


Date of construction: the one-story brick school building at 65R Bailey Street appeared between the 1918 and 1933 atlases.
Bailey Street Schools
The maps from 1884 through 1918 show the building on the left usually as wood-frame construction, but in 1889 it was shown as masonry. Perhaps the confusion is that the first floor seems to be clad in masonry and the upper floor in wood. In the early years the school was known only as Primary School. From 1884 to 1898 the building at the left (where the VFW post is located today) is the only school building. The 1904 map shows that the city had acquired the double house on the right to serve as a school. By 1910 the house had been demolished. The 1904, 1910, and 1918 maps show the name of the school as the Bailey Street School. The 1933 map shows that the brick building that was later the Thomas Francis Leen School is in place (where the house used to be), but its name was the Helen Burgess School in that year. The original school building still existed in 1933. I don’t know when it was removed and replaced with the concrete block VFW building that stands there today. The VFW post is slated for redevelopment. The Leen School was surplus property in the 1980s, and the City turned the building into a residential facility.
Charlie O’Hara, who was in elementary school there from kindergarten in 1936 until 1942, says: When I moved here in 1935 the schools were called the Bailey Street Schools, although the official names were the Helen F. Burgess on the left (older building) and the Thomas F. Leen on the right, where the mansard house was located. To my knowledge the Leen was never called the Burgess. I attended the Burgess (old building) in 1936 and the Leen from 1937-1942.
The Burgess was a fine old building with two classrooms on the first floor and two on the second. The first floor was of brick construction with a wooden framed second floor. I believe that the second floor wooden structure was removed and the brick first floor retained when the VFW Post took possession. Although the present VFW building has been painted white, upon close inspection the original brick first story is intact with a cement block addition on the right side and rear.
Bailey Street School, Helen Burgess School, Thomas Francis Leen School
from maps and atlases:
1874 Manuel Silva owned the double house, each side sitting on 5,250 sf and two vacant lots (10,635 sf and 11,203 sf) to the east plus two vacant lots to west of 10,500 sf each.
The two vacant lots to the east later held the school house in the photograph.
1884 63 Bailey City of Boston Primary School – wood-frame
65 Bailey owned by William F. Keal
1889 63 Bailey City of Boston Primary School – brick
65 Bailey owned Mary R. Cleaves on the right, and Michl Barrett on the left (east side)
1894 63 Bailey City of Boston Primary School
65 Bailey Mary R. Cleaves
1898 Primary School – wood-frame
1904 Bailey Street School – 2 wood-frame buildings (took over the lot & building at 63-65 Bailey)
1910 same
1918 Bailey Street School – shows on the map as a wood-frame building
1933 Helen Burgess School includes brick school building and wood-frame building (where the VFW post is today)
Deed
Re: 65R Bailey
December 21, 1898 from Stephen A. Cleaves and Mary R. Cleaves of Quincy to City of Boston 2574.619
consideration $9,250
September 24, 1890 from Henry M. Snell to Mary R. Cleaves 1957.581 lot A plan at 1599.436
so Mary owns both sides of the house
June 15, 1889 from Matthew Dalton to Henry M. Snell 1883.311
June 14, 1889 foreclosure auction from Henry M. Snell assignee of mortgage to Matthew Dalton
mortgage September 25, 1883 from Frederick J. Berry and Emma A. Berry to Joshua W. Clapp 1612.61
May 8, 1889 from William H. Keal to Mary R. Cleaves, wife of Stephen A. Cleaves, 1875.556 part lot 53
June 2, 1883 from Austin D. Collins to Mary R. Cleaves 1599.436 lot B
consideration $3,000 for the west half of the house
June 1, 1883 from Austin D. Collins to Emma A. Berry 1599.435 the east side of the house
from William H. Keal to Austin D. Collins
Deeds re: 63 Bailey
how did the property transfer to the City of Boston?
September 18, 1873 from Manuel Silva to Moses Williams Jr of Brookline 1177.103 lots 50, 51, 52, 53
lots 50 and 51 became the VFW property
lot 52 became the one-story brick school house
September 22, 1871from Benjamin B. Newhall to Manuel Silva 1070.277 lots 24, 50, 51, 52, 53, 54
consideration $16,868.40 part of the premises conveyed to Newhall by the executors of the John Bailey estate conveyed December 1, 1869 Suffolk 990.69
The school property on the 1894 map had 21,800 sf adjacent to 65 and the lot where Chip Canty owned
63 Bailey was lots 50 & 51 on plan in 1870 1008.212
65R Bailey was part lot 52 and all of lot 53