diff --git a/Doc/whatsnew/3.14.rst b/Doc/whatsnew/3.14.rst
index 72abfebd46f2b9..36d50ef10e8296 100644
--- a/Doc/whatsnew/3.14.rst
+++ b/Doc/whatsnew/3.14.rst
@@ -210,6 +210,10 @@ configuration mechanisms).
 
 Other language changes
 ======================
+* Constant comparsion expressions are now folded and evaluated before runtime.
+  For example, expressions like: ``"str" in ("str",)`` or ``1 == 1.0 == True``
+  are now pre-evaluated.
+  (Contributed by Yan Yanchii in :gh:`128706`.)
 
 * The :func:`map` built-in now has an optional keyword-only *strict* flag
   like :func:`zip` to check that all the iterables are of equal length.
diff --git a/Lib/test/test_ast/test_ast.py b/Lib/test/test_ast/test_ast.py
index c268a1f00f938e..2bd8aadadfe31a 100644
--- a/Lib/test/test_ast/test_ast.py
+++ b/Lib/test/test_ast/test_ast.py
@@ -3180,7 +3180,8 @@ def create_unaryop(operand):
                 self.assert_ast(result_code, non_optimized_target, optimized_target)
 
     def test_folding_not(self):
-        code = "not (1 %s (1,))"
+        # use list as left-hand side to avoid folding constant expression to True/False
+        code = "not ([] %s (1,))"
         operators = {
             "in": ast.In(),
             "is": ast.Is(),
@@ -3192,7 +3193,7 @@ def test_folding_not(self):
 
         def create_notop(operand):
             return ast.UnaryOp(op=ast.Not(), operand=ast.Compare(
-                left=ast.Constant(value=1),
+                left=ast.List(),
                 ops=[operators[operand]],
                 comparators=[ast.Tuple(elts=[ast.Constant(value=1)])]
             ))
@@ -3201,7 +3202,7 @@ def create_notop(operand):
             result_code = code % op
             non_optimized_target = self.wrap_expr(create_notop(op))
             optimized_target = self.wrap_expr(
-                ast.Compare(left=ast.Constant(1), ops=[opt_operators[op]], comparators=[ast.Constant(value=(1,))])
+                ast.Compare(left=ast.List(), ops=[opt_operators[op]], comparators=[ast.Constant(value=(1,))])
             )
 
             with self.subTest(
@@ -3239,8 +3240,58 @@ def test_folding_tuple(self):
 
         self.assert_ast(code, non_optimized_target, optimized_target)
 
-    def test_folding_comparator(self):
-        code = "1 %s %s1%s"
+    def test_folding_compare(self):
+        true = self.wrap_expr(ast.Constant(value=True))
+        false = self.wrap_expr(ast.Constant(value=False))
+
+        folded_cases = (
+            ("3 > 2 > 1", (ast.Constant(3), [ast.Gt(), ast.Gt()], [ast.Constant(value=2), ast.Constant(value=1)]), true),
+            ("3 > 4 > 1", (ast.Constant(3), [ast.Gt(), ast.Gt()], [ast.Constant(value=4), ast.Constant(value=1)]), false),
+            ("3 >= 3 >= 1", (ast.Constant(3), [ast.GtE(), ast.GtE()], [ast.Constant(value=3), ast.Constant(value=1)]), true),
+            ("3 >= 4 >= 1", (ast.Constant(3), [ast.GtE(), ast.GtE()], [ast.Constant(value=4), ast.Constant(value=1)]), false),
+            ("1 < 2 < 3", (ast.Constant(1), [ast.Lt(), ast.Lt()], [ast.Constant(value=2), ast.Constant(value=3)]), true),
+            ("1 < 0 < 3", (ast.Constant(1), [ast.Lt(), ast.Lt()], [ast.Constant(value=0), ast.Constant(value=3)]), false),
+            ("1 <= 2 <= 3", (ast.Constant(1), [ast.LtE(), ast.LtE()], [ast.Constant(value=2), ast.Constant(value=3)]), true),
+            ("1 <= 0 <= 3", (ast.Constant(1), [ast.LtE(), ast.LtE()], [ast.Constant(value=0), ast.Constant(value=3)]), false),
+            ("1 == 1.0 == True", (ast.Constant(1), [ast.Eq(), ast.Eq()], [ast.Constant(value=1.0), ast.Constant(value=True)]), true),
+            ("1 == 2 == True", (ast.Constant(1), [ast.Eq(), ast.Eq()], [ast.Constant(value=2), ast.Constant(value=True)]), false),
+            ("1 != 2 != 3", (ast.Constant(1), [ast.NotEq(), ast.NotEq()], [ast.Constant(value=2), ast.Constant(value=3)]), true),
+            ("1 != 1 != 3", (ast.Constant(1), [ast.NotEq(), ast.NotEq()], [ast.Constant(value=1), ast.Constant(value=3)]), false),
+            ("1 in [1, 2]", (ast.Constant(1), [ast.In()], [ast.List(elts=[ast.Constant(1), ast.Constant(2)])]), true),
+            ("1 in [2, 2]", (ast.Constant(1), [ast.In()], [ast.List(elts=[ast.Constant(2), ast.Constant(2)])]), false),
+            ("1 not in [1, 2]", (ast.Constant(1), [ast.NotIn()], [ast.List(elts=[ast.Constant(1), ast.Constant(2)])]), false),
+            ("1 not in [2, 2]", (ast.Constant(1), [ast.NotIn()], [ast.List(elts=[ast.Constant(2), ast.Constant(2)])]), true),
+        )
+
+        for code, original, folded in folded_cases:
+            left, ops, comparators = original
+            unfolded = self.wrap_expr(ast.Compare(left=left, ops=ops, comparators=comparators))
+            self.assert_ast(code=code, non_optimized_target=unfolded, optimized_target=folded)
+
+        # these should stay as they were
+        unfolded_cases = (
+            ("3 > 2 > []", ast.Compare(left=ast.Constant(3), ops=[ast.Gt(), ast.Gt()], comparators=[ast.Constant(2), ast.List()])),
+            ("1 > [] > 0", ast.Compare(left=ast.Constant(1), ops=[ast.Gt(), ast.Gt()], comparators=[ast.List(), ast.Constant(0)])),
+            ("1 >= [] >= 0", ast.Compare(left=ast.Constant(1), ops=[ast.GtE(), ast.GtE()], comparators=[ast.List(), ast.Constant(0)])),
+            ("1 < [] < 0", ast.Compare(left=ast.Constant(1), ops=[ast.Lt(), ast.Lt()], comparators=[ast.List(), ast.Constant(0)])),
+            ("1 <= [] <= 0", ast.Compare(left=ast.Constant(1), ops=[ast.LtE(), ast.LtE()], comparators=[ast.List(), ast.Constant(0)])),
+            ("1 == [] == 0", ast.Compare(left=ast.Constant(1), ops=[ast.Eq(), ast.Eq()], comparators=[ast.List(), ast.Constant(0)])),
+            ("1 != [] != 0", ast.Compare(left=ast.Constant(1), ops=[ast.NotEq(), ast.NotEq()], comparators=[ast.List(), ast.Constant(0)])),
+            ("1 is 1", ast.Compare(left=ast.Constant(1), ops=[ast.Is()], comparators=[ast.Constant(1)])),
+            ("1 is not 1", ast.Compare(left=ast.Constant(1), ops=[ast.IsNot()], comparators=[ast.Constant(1)])),
+            # invalid also should stay as they were
+            ("1 in 1", ast.Compare(left=ast.Constant(1), ops=[ast.In()], comparators=[ast.Constant(1)])),
+            ("1 not in 1", ast.Compare(left=ast.Constant(1), ops=[ast.NotIn()], comparators=[ast.Constant(1)])),
+        )
+
+        for code, expected in unfolded_cases:
+            self.assertTrue(ast.compare(ast.parse(code), self.wrap_expr(expected)))
+
+    def test_folding_comparator_list_set_subst(self):
+        """Test substitution of list/set with tuple/frozenset in expressions like "1 in [1]" or "1 in {1}" """
+
+        # use list as left-hand side to avoid folding constant comparison expression to True/False
+        code = "[] %s %s1%s"
         operators = [("in", ast.In()), ("not in", ast.NotIn())]
         braces = [
             ("[", "]", ast.List, (1,)),
@@ -3249,11 +3300,11 @@ def test_folding_comparator(self):
         for left, right, non_optimized_comparator, optimized_comparator in braces:
             for op, node in operators:
                 non_optimized_target = self.wrap_expr(ast.Compare(
-                    left=ast.Constant(1), ops=[node],
+                    left=ast.List(), ops=[node],
                     comparators=[non_optimized_comparator(elts=[ast.Constant(1)])]
                 ))
                 optimized_target = self.wrap_expr(ast.Compare(
-                    left=ast.Constant(1), ops=[node],
+                    left=ast.List(), ops=[node],
                     comparators=[ast.Constant(value=optimized_comparator)]
                 ))
                 self.assert_ast(code % (op, left, right), non_optimized_target, optimized_target)
diff --git a/Misc/NEWS.d/next/Core_and_Builtins/2025-01-10-18-42-57.gh-issue-128706.4T2XSt.rst b/Misc/NEWS.d/next/Core_and_Builtins/2025-01-10-18-42-57.gh-issue-128706.4T2XSt.rst
new file mode 100644
index 00000000000000..1949a649d9f748
--- /dev/null
+++ b/Misc/NEWS.d/next/Core_and_Builtins/2025-01-10-18-42-57.gh-issue-128706.4T2XSt.rst
@@ -0,0 +1 @@
+Add constant folding for constant comparisons.
diff --git a/Python/ast_opt.c b/Python/ast_opt.c
index 01e208b88eca8b..06034f2d805832 100644
--- a/Python/ast_opt.c
+++ b/Python/ast_opt.c
@@ -639,6 +639,68 @@ fold_compare(expr_ty node, PyArena *arena, _PyASTOptimizeState *state)
             return 0;
         }
     }
+
+    static const int richcompare_table[] = {
+        [Eq] = Py_EQ,
+        [NotEq] = Py_NE,
+        [Gt] = Py_GT,
+        [Lt] = Py_LT,
+        [GtE] = Py_GE,
+        [LtE] = Py_LE,
+    };
+
+    if (node->v.Compare.left->kind == Constant_kind) {
+        PyObject *lhs = node->v.Compare.left->v.Constant.value;
+        for (Py_ssize_t i = 0; i < asdl_seq_LEN(args); i++) {
+            expr_ty curr_expr = (expr_ty)asdl_seq_GET(args, i);
+            if (curr_expr->kind != Constant_kind) {
+                /* try to fold only if every comparator is constant */
+                return 1;
+            }
+            int op = asdl_seq_GET(ops, i);
+            if (op == Is || op == IsNot) {
+                /* Do not fold "is" and "is not" expressions since this breaks
+                   expected syntax warnings. For example:
+                     >>> 1 is 1
+                     <python-input-0>:1: SyntaxWarning: "is" with 'int' literal. Did you mean "=="?
+                 */
+                return 1;
+            }
+            PyObject *rhs = curr_expr->v.Constant.value;
+            int res;
+            switch (op) {
+                case Eq:
+                case NotEq:
+                case Gt:
+                case Lt:
+                case GtE:
+                case LtE: {
+                    res = PyObject_RichCompareBool(lhs, rhs, richcompare_table[op]);
+                    break;
+                }
+                case In:
+                case NotIn: {
+                    res = PySequence_Contains(rhs, lhs);
+                    if (op == NotIn && res >= 0) {
+                        res = !res;
+                    }
+                    break;
+                }
+                default:
+                    Py_UNREACHABLE();
+            }
+            if (res == 0) {
+                /* shortcut, whole expression is False */
+                return make_const(node, Py_False, arena);
+            }
+            else if (res < 0) {
+                return make_const(node, NULL, arena);
+            }
+            lhs = rhs;
+        }
+        /* whole expression is True */
+        return make_const(node, Py_True, arena);
+    }
     return 1;
 }