In the last four years (2019–2022), Winsor graduates have most often entered the following colleges and universities:
Amherst College (4)
Barnard College (6)
Boston College (13)
Boston University (8)
Brown University (8)
Carnegie Mellon University (3)
Colby College (4)
Columbia University (5)
Cornell University (3)
Davidson College (3)
Duke University (4)
Emory University (7)
Fordham University (3)
George Washington University (4)
Georgetown University (8)
Hamilton College (3)
Harvard University (15)
Johns Hopkins University (3)
Massachusetts Institute of Technology (6)
McGill University (3)
Middlebury College (3)
New York University (6)
Northeastern University (4)
Northwestern University (4)
Princeton University (3)
Stanford University (3)
Syracuse University (3)
Tufts University (9)
Tulane University (3)
University of Michigan-Ann Arbor (3)
University of Pennsylvania (5)
University of St Andrews (3)
Washington University in St Louis (9)
Wellesley College (7)
Yale University (7)
2 each to:
American University, Bates College, Bentley University, Bowdoin College, Brandeis University, Colorado College, Dartmouth College, Elon University,
Kenyon College, Mount Holyoke College, The University of North Carolina at Chapel Hill, Oberlin College, University of Richmond, Santa Clara University, University of Southern California, Southern Methodist University, University of Virginia, Wesleyan University, University of Wisconsin—Madison
1 each to:
The American University of Paris, Berklee College of Music, Bryn Mawr College, Carleton College, University of Chicago, Claremont McKenna College, University of Connecticut, Duke Kunshan University, Fashion Institute of Technology, Georgia Institute of Technology, Guildhall School of Music and Drama, Harvey Mudd College, Haverford College, College of the Holy Cross, Macalester College, University of Maryland-College Park, University of Massachusetts-Amherst, University of Massachusetts-Lowell, University of Notre Dame, Occidental College, Franklin W Olin College of Engineering, University of Pittsburgh, Pomona College, Rhode Island School of Design, Rice University, Salve Regina University, Scripps College, Smith College, Stonehill College, Trinity College, Vassar College, University of Vermont, Wells College, Wentworth Institute of Technology, William & Mary, Williams College, Worcester Polytechnic Institute