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1920's, the upper story of the building was condemned as unsafe. The Board later determined to construct a new school on the site, had plans drawn, and advertised for contracts. Some advocated a plan to purchase the present (1988)brick office building, then Dr. J.L. Hanmer's home, across from the old Armory, demolishing it, and putting the new school in the center of the combined properties, but this idea was rejected. Bids for the school were opened by the Board April 27, 1927 and referred to the building committee. On May 2, however, all bids were rejected by the board, and the building committee directed to consult with the architects. In the meantime, a house adjacent to the school on Liberty Street was moved to Highland Avenue as the lot had been purchased by the board. Robert R. Graham, one of the architects announced certain cost-saving measures had been implemented to lower the cost of the school to the approved amount. New bids were sought which were reviewed May 26. Construction contracts were let May 31, and signed by Board President Leslie H. Prince the next day. Neilson Kinnear of Middletown was the general contractor, with other contracts going to P.C. D
P.C. Doherty (plumbing), Enterprise Electrical (electrical), and G.A. Swalm & Son, Co., Inc. (heating and ventilating). Architects were David H. Canfield and Robert R. Graham. Construction cost was $138,505. To avoid delays in demolishing the old school, arrangements were made to transfer pupils to the lower floor of the Linden Avenue School. The last classes in the old "yellow plaster-covered brick" building were held June 3, 1927. The present (1988) Liberty Street School opened April 16, 1928, although it was not "entirely completed" at the time.
On July 3, 1869, taxpayers voted to appropriate $2,000 to purchase property on which to build the 3rd Ward school. It was proposed to locate the school on the grounds of the Academy, but the board instead purchased a lot owned by James J. Mills opposite the residence of Benjamin Bennett for $1,500. This is now (1988) the site of Bennett Hill Park located at the south end of East Avenue, corner of Genung Street. By mid-July, 1869, the building contract had been awarded to Van Horn & Sloat, who at $5,630 were the lowest bidders. Van Horn & Sloat succeeded the firm of Van Horn & Son in early 1869. Cornelius J. Sloat would soon become one of Middletown's leading architects. Work on the school was begun about August 1, with Robert Lemon doing the masonry work. By early October, the walls were up and the roof was on. Bennett Hill School opened late in 1869 or early 1870. It was torn down in 1945.
In July of 1873, the Board of Education's Building Committee advertised for proposals to build a new 4th Ward school. The lot on which the school was built fronted on Prospect Avenue and ran back to what is now Ridge Street, with the structure itself sitting at the top of the hill "command[ingl a good view of the village." It was also called Beattie Hill School as the mansion of Israel O. Beattie stood nearby: about where the Tower Building of Horton Hospital now stands ( Beattie's home was later converted to the Children's Home). It was thought the 4th Ward School