diff --git a/libs/text-splitters/langchain_text_splitters/base.py b/libs/text-splitters/langchain_text_splitters/base.py
index b0fb33caa2d..bdf7ae7be2d 100644
--- a/libs/text-splitters/langchain_text_splitters/base.py
+++ b/libs/text-splitters/langchain_text_splitters/base.py
@@ -35,7 +35,7 @@ class TextSplitter(BaseDocumentTransformer, ABC):
         chunk_size: int = 4000,
         chunk_overlap: int = 200,
         length_function: Callable[[str], int] = len,
-        keep_separator: bool = False,
+        keep_separator: Union[bool, Literal["start", "end"]] = False,
         add_start_index: bool = False,
         strip_whitespace: bool = True,
     ) -> None:
@@ -45,7 +45,8 @@ class TextSplitter(BaseDocumentTransformer, ABC):
             chunk_size: Maximum size of chunks to return
             chunk_overlap: Overlap in characters between chunks
             length_function: Function that measures the length of given chunks
-            keep_separator: Whether to keep the separator in the chunks
+            keep_separator: Whether to keep the separator and where to place it
+                            in each corresponding chunk (True='start')
             add_start_index: If `True`, includes chunk's start index in metadata
             strip_whitespace: If `True`, strips whitespace from the start and end of
                               every document
diff --git a/libs/text-splitters/langchain_text_splitters/character.py b/libs/text-splitters/langchain_text_splitters/character.py
index 0f2ce97bcb0..6783f98363a 100644
--- a/libs/text-splitters/langchain_text_splitters/character.py
+++ b/libs/text-splitters/langchain_text_splitters/character.py
@@ -1,7 +1,7 @@
 from __future__ import annotations
 
 import re
-from typing import Any, List, Optional
+from typing import Any, List, Literal, Optional, Union
 
 from langchain_text_splitters.base import Language, TextSplitter
 
@@ -29,17 +29,25 @@ class CharacterTextSplitter(TextSplitter):
 
 
 def _split_text_with_regex(
-    text: str, separator: str, keep_separator: bool
+    text: str, separator: str, keep_separator: Union[bool, Literal["start", "end"]]
 ) -> List[str]:
     # Now that we have the separator, split the text
     if separator:
         if keep_separator:
             # The parentheses in the pattern keep the delimiters in the result.
             _splits = re.split(f"({separator})", text)
-            splits = [_splits[i] + _splits[i + 1] for i in range(1, len(_splits), 2)]
+            splits = (
+                ([_splits[i] + _splits[i + 1] for i in range(0, len(_splits) - 1, 2)])
+                if keep_separator == "end"
+                else ([_splits[i] + _splits[i + 1] for i in range(1, len(_splits), 2)])
+            )
             if len(_splits) % 2 == 0:
                 splits += _splits[-1:]
-            splits = [_splits[0]] + splits
+            splits = (
+                (splits + [_splits[-1]])
+                if keep_separator == "end"
+                else ([_splits[0]] + splits)
+            )
         else:
             splits = re.split(separator, text)
     else:
diff --git a/libs/text-splitters/tests/unit_tests/test_text_splitters.py b/libs/text-splitters/tests/unit_tests/test_text_splitters.py
index 3d88d786fb3..062f4d089d1 100644
--- a/libs/text-splitters/tests/unit_tests/test_text_splitters.py
+++ b/libs/text-splitters/tests/unit_tests/test_text_splitters.py
@@ -112,6 +112,50 @@ def test_character_text_splitter_keep_separator_regex(
     assert output == expected_output
 
 
+@pytest.mark.parametrize(
+    "separator, is_separator_regex", [(re.escape("."), True), (".", False)]
+)
+def test_character_text_splitter_keep_separator_regex_start(
+    separator: str, is_separator_regex: bool
+) -> None:
+    """Test splitting by characters while keeping the separator
+    that is a regex special character and placing it at the start of each chunk.
+    """
+    text = "foo.bar.baz.123"
+    splitter = CharacterTextSplitter(
+        separator=separator,
+        chunk_size=1,
+        chunk_overlap=0,
+        keep_separator="start",
+        is_separator_regex=is_separator_regex,
+    )
+    output = splitter.split_text(text)
+    expected_output = ["foo", ".bar", ".baz", ".123"]
+    assert output == expected_output
+
+
+@pytest.mark.parametrize(
+    "separator, is_separator_regex", [(re.escape("."), True), (".", False)]
+)
+def test_character_text_splitter_keep_separator_regex_end(
+    separator: str, is_separator_regex: bool
+) -> None:
+    """Test splitting by characters while keeping the separator
+    that is a regex special character and placing it at the end of each chunk.
+    """
+    text = "foo.bar.baz.123"
+    splitter = CharacterTextSplitter(
+        separator=separator,
+        chunk_size=1,
+        chunk_overlap=0,
+        keep_separator="end",
+        is_separator_regex=is_separator_regex,
+    )
+    output = splitter.split_text(text)
+    expected_output = ["foo.", "bar.", "baz.", "123"]
+    assert output == expected_output
+
+
 @pytest.mark.parametrize(
     "separator, is_separator_regex", [(re.escape("."), True), (".", False)]
 )