diff --git a/bindings/pydrake/common/schema_py.cc b/bindings/pydrake/common/schema_py.cc
index b1b89eb74e87..b461be5d3e8e 100644
--- a/bindings/pydrake/common/schema_py.cc
+++ b/bindings/pydrake/common/schema_py.cc
@@ -2,6 +2,7 @@
 #include <vector>
 
 #include "pybind11/eigen.h"
+#include "pybind11/eval.h"
 #include "pybind11/pybind11.h"
 #include "pybind11/stl.h"
 
@@ -299,6 +300,47 @@ PYBIND11_MODULE(schema, m) {
     DefAttributesUsingSerialize(&cls, cls_doc);
     DefReprUsingSerialize(&cls);
     DefCopyAndDeepCopy(&cls);
+
+    // To support the atypical C++ implementation of Transform::Serialize, we
+    // need to support attribute operations on Rotation that should actually
+    // apply to the Rotation::value member field instead. We'll achieve that by
+    // adding special-cases to getattr and setattr.
+    cls.def("__getattr__", [](const Class& self, py::str name) -> py::object {
+      if (std::holds_alternative<Rotation::Rpy>(self.value)) {
+        const std::string name_cxx = name;
+        if (name_cxx == "deg") {
+          py::object self_py = py::cast(self, py_rvp::reference);
+          return self_py.attr("value").attr(name);
+        }
+      }
+      if (std::holds_alternative<Rotation::AngleAxis>(self.value)) {
+        const std::string name_cxx = name;
+        if ((name_cxx == "angle_deg") || (name_cxx == "axis")) {
+          py::object self_py = py::cast(self, py_rvp::reference);
+          return self_py.attr("value").attr(name);
+        }
+      }
+      return py::eval("object.__getattr__")(self, name);
+    });
+    cls.def("__setattr__", [](Class& self, py::str name, py::object value) {
+      if (std::holds_alternative<Rotation::Rpy>(self.value)) {
+        const std::string name_cxx = name;
+        if (name_cxx == "deg") {
+          py::object self_py = py::cast(self, py_rvp::reference);
+          self_py.attr("value").attr(name) = value;
+          return;
+        }
+      }
+      if (std::holds_alternative<Rotation::AngleAxis>(self.value)) {
+        const std::string name_cxx = name;
+        if ((name_cxx == "angle_deg") || (name_cxx == "axis")) {
+          py::object self_py = py::cast(self, py_rvp::reference);
+          self_py.attr("value").attr(name) = value;
+          return;
+        }
+      }
+      py::eval("object.__setattr__")(self, name, value);
+    });
   }
 
   // Bindings for transform.h.
@@ -326,8 +368,31 @@ PYBIND11_MODULE(schema, m) {
     // The Transform::Serialize does something sketchy for the "rotation" field.
     // We'll undo that damage for the attribute getter and setter functions, but
     // notably we must leave the __fields__ manifest unchanged to match the C++
-    // serialization convention.
-    cls.def_readwrite("rotation", &Class::rotation, cls_doc.rotation.doc);
+    // serialization convention and the setter needs to accept either a Rotation
+    // (the actual type of the property) or any of the allowed Rotation::Variant
+    // types (which will occur during YAML deserialization).
+    using RotationOrNestedValue = std::variant<Rotation, Rotation::Identity,
+        Rotation::Rpy, Rotation::AngleAxis, Rotation::Uniform>;
+    static_assert(
+        std::variant_size_v<RotationOrNestedValue> ==
+        1 /* for Rotation */ + std::variant_size_v<Rotation::Variant>);
+    cls.def_property(
+        "rotation",
+        // The getter is just the usual, no special magic.
+        [](const Class& self) { return &self.rotation; },
+        // The setter accepts a more generous allowed set of argument types.
+        [](Class& self, RotationOrNestedValue value_variant) {
+          std::visit(
+              [&self]<typename T>(const T& new_value) {
+                if constexpr (std::is_same_v<T, Rotation>) {
+                  self.rotation = new_value;
+                } else {
+                  self.rotation.value = new_value;
+                }
+              },
+              value_variant);
+        },
+        py_rvp::reference_internal, cls_doc.rotation.doc);
     DefReprUsingSerialize(&cls);
     DefCopyAndDeepCopy(&cls);
   }
diff --git a/bindings/pydrake/common/test/schema_serialization_test.py b/bindings/pydrake/common/test/schema_serialization_test.py
index 3aa812d9d97f..a7e8a057476f 100644
--- a/bindings/pydrake/common/test/schema_serialization_test.py
+++ b/bindings/pydrake/common/test/schema_serialization_test.py
@@ -5,6 +5,7 @@
 import unittest
 
 import numpy as np
+from numpy.testing import assert_allclose
 
 import pydrake.common.schema as mut
 from pydrake.common.yaml import yaml_load_typed
@@ -68,7 +69,7 @@ def test_rpy(self):
         rpy = RollPitchYaw(x.GetDeterministicValue())
         rpy_deg = np.array([math.degrees(z) for z in rpy.vector()])
         expected = np.array([10.0, 20.0, 30.0])
-        np.testing.assert_allclose(rpy_deg, expected)
+        assert_allclose(rpy_deg, expected)
 
     def test_angle_axis(self):
         data = "value: !AngleAxis { angle_deg: 10.0, axis: [0, 1, 0] }"
@@ -76,7 +77,7 @@ def test_angle_axis(self):
         self.assertTrue(x.IsDeterministic())
         aa = x.GetDeterministicValue().ToAngleAxis()
         self.assertAlmostEqual(math.degrees(aa.angle()), 10.0)
-        np.testing.assert_allclose(aa.axis(), [0.0, 1.0, 0.0])
+        assert_allclose(aa.axis(), [0.0, 1.0, 0.0])
 
     def test_uniform(self):
         data = "value: !Uniform {}"
@@ -95,6 +96,66 @@ def test_rpy_uniform(self):
         self.assertFalse(x.IsDeterministic())
 
 
-# TODO(jwnimmer-tri) Add serialization tests for schema.Translation. For now,
-# the weird C++ `MakeNameValue("rotation", &rotation.value)` is incompatible
-# with how our Python deserialization works.
+class TestTransformSerialization(unittest.TestCase):
+    """Serialization tests related to schema/transform.h"""
+
+    def test_deterministic(self):
+        data = dedent("""
+        base_frame: foo
+        translation: [1.0, 2.0, 3.0]
+        rotation: !Rpy { deg: [10, 20, 30] }
+        """)
+        x = yaml_load_typed(schema=mut.Transform, data=data)
+        self.assertEqual(x.base_frame, "foo")
+        assert_allclose(x.translation, [1.0, 2.0, 3.0])
+        assert_allclose(x.rotation.value.deg, [10, 20, 30])
+
+    def test_random(self):
+        data = dedent("""
+        base_frame: bar
+        translation: !UniformVector
+          min: [1.0, 2.0, 3.0]
+          max: [4.0, 5.0, 6.0]
+        rotation: !Uniform {}
+        """)
+        x = yaml_load_typed(schema=mut.Transform, data=data)
+        self.assertEqual(x.base_frame, "bar")
+        assert_allclose(x.translation.min, [1.0, 2.0, 3.0])
+        assert_allclose(x.translation.max, [4.0, 5.0, 6.0])
+        self.assertEqual(type(x.rotation.value), mut.Rotation.Uniform)
+
+    def test_random_bounded(self):
+        data = dedent("""
+        base_frame: baz
+        translation: !UniformVector
+          min: [1.0, 2.0, 3.0]
+          max: [4.0, 5.0, 6.0]
+        rotation: !Rpy
+          deg: !UniformVector
+            min: [380, -0.25, -1.0]
+            max: [400,  0.25,  1.0]
+        """)
+        x = yaml_load_typed(schema=mut.Transform, data=data)
+        self.assertEqual(x.base_frame, "baz")
+        assert_allclose(x.translation.min, [1.0, 2.0, 3.0])
+        assert_allclose(x.translation.max, [4.0, 5.0, 6.0])
+        assert_allclose(x.rotation.value.deg.min, [380, -0.25, -1.0])
+        assert_allclose(x.rotation.value.deg.max, [400,  0.25,  1.0])
+
+    def test_random_angle_axis(self):
+        data = dedent("""
+        base_frame: quux
+        rotation: !AngleAxis
+          angle_deg: !Uniform
+            min: 10
+            max: 20
+          axis: !UniformVector
+            min: [1, 2, 3]
+            max: [4, 5, 6]
+        """)
+        x = yaml_load_typed(schema=mut.Transform, data=data)
+        self.assertEqual(x.base_frame, "quux")
+        self.assertEqual(x.rotation.value.angle_deg.min, 10)
+        self.assertEqual(x.rotation.value.angle_deg.max, 20)
+        assert_allclose(x.rotation.value.axis.min, [1, 2, 3])
+        assert_allclose(x.rotation.value.axis.max, [4, 5, 6])
diff --git a/bindings/pydrake/common/test/schema_test.py b/bindings/pydrake/common/test/schema_test.py
index 8f21e903c9e1..9d795142d09c 100644
--- a/bindings/pydrake/common/test/schema_test.py
+++ b/bindings/pydrake/common/test/schema_test.py
@@ -211,6 +211,8 @@ def test_transform(self):
 
         dut.set_rotation_rpy_deg([0.1, 0.2, 0.3])
         np.testing.assert_equal(dut.rotation.value.deg, [0.1, 0.2, 0.3])
+        dut.rotation.value.deg = [0.4, 0.5, 0.6]
+        np.testing.assert_equal(dut.rotation.value.deg, [0.4, 0.5, 0.6])
 
         # Attributes.
         self.assertEqual(mut.Transform(base_frame="base").base_frame, "base")
diff --git a/bindings/pydrake/common/yaml.py b/bindings/pydrake/common/yaml.py
index 694a202dec27..ee9b544ccf41 100644
--- a/bindings/pydrake/common/yaml.py
+++ b/bindings/pydrake/common/yaml.py
@@ -211,6 +211,7 @@ def _merge_yaml_dict_item_into_target(*, options, name, yaml_value,
     writing the result to the field named `name` of the given `target` object.
     """
     # The target can be either a dictionary or a dataclass.
+    assert target is not None
     if isinstance(target, collections.abc.Mapping):
         old_value = target[name]
         setter = functools.partial(target.__setitem__, name)
@@ -372,6 +373,7 @@ def _merge_yaml_dict_into_target(*, options, yaml_dict,
     raw strings, dictionaries, lists, etc.).
     """
     assert isinstance(yaml_dict, collections.abc.Mapping), yaml_dict
+    assert target is not None
     static_field_map = _enumerate_field_types(target_schema)
     schema_names = list(static_field_map.keys())
     schema_optionals = set([