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I am currently working on an integration with other systems and I have the JSON coming back in the below format.

 "searchDocumentsResponse": 
 "documentsIndexInfo": [
 
 "contentElementsInfo": 
 "fileName": "test.pdf",
 "fileSize": 1010694,
 "indexNumber": 0,
 "mimeType": "application/pdf"
 ,
 "guid": "123456789-1234-1234-1234-92393300000",
 "majorVersion": 1,
 "minorVersion": 0,
 "objectStore": "09876543212-1234-4B53-8CC5-469444E92456",
 "pathName": "",
 "properties": [
 
 "multiValue": false,
 "name": "Document_Type",
 "type": "STRING",
 "value": "TEST"
 ,
 
 "multiValue": false,
 "name": "ScanTMSTMP",
 "type": "DATE",
 "value": "5/16/1920"
 ,
 
 "multiValue": false,
 "name": "f_DocNumber",
 "type": "STRING",
 "value": ""
 ,
 
 "multiValue": false,
 "name": "MimeType",
 "type": "STRING",
 "value": "application/pdf"
 ,
 
 "multiValue": false,
 "name": "DateCreated",
 "type": "DATE",
 "value": "5/31/2018"
 
 ]

 
 ],
 "numDocObjectsFound": 1,
 "numDocObjectsReturned": 1,
 "responseStatus": 
 "code": "OK",
 "message": ""
 ,
 "startingDocObject": 0
 

And I am trying to parse the response like below:

public class DocumentRetrievalResponse 

 public SearchDocumentsResponse searchDocumentsResponse get;set;
 public cecDocumentRetrievalResponse()
 

 public class SearchDocumentsResponse 
 public String numDocObjectsFound get;set;
 public String numDocObjectsReturned get;set;
 public ResponseStatus responseStatus get;set;
 public String startingDocObject get;set;
 public List<DocumentsIndexInfo> documentsIndexInfo get;set; documentsIndexInfo = new List<DocumentsIndexInfo>();
 public SearchDocumentsResponse()
 
 

 public class ResponseStatus 
 public String code get;set;
 public String messageget;set;
 public ResponseStatus()

 
 

 public class DocumentsIndexInfo 
 public String guidget;set; guid = null;
 public Integer majorVersionget;set; majorVersion = 0;
 public Integer minorVersionget;set;minorVersion = 0;
 public String objectStoreget;set;objectStore = null;
 public String pathNameget;set; pathName = null;
 public ContentElementsInfo contentElementsInfo get;set;
 public List<Properties> propertiesget;set; properties = new List<Properties>(); 

 

 public class ContentElementsInfo 
 public String fileNameget;set; fileName = null;
 public Integer fileSizeget;set; fileSize = 0;
 public Integer indexNumberget;set; indexNumber = 0;
 public String mimeTypeget;set;mimeType = null;
 


 public class Properties 
 public String name get;set;
 public String value get;set; 
 public String type get;set; 
 public String multiValue get;set; multiValue = 'false';
 

And to deserialize, I have the below lines:

System.Type resultType = System.Type.forName('DocumentRetrievalResponse');
DocumentRetrievalResponse deserializeResults = 
 (DocumentRetrievalResponse)JSON.deserialize(result, resultType);

When I run it, I get the JSON Exception as below. I might be overthinking and missing something here. Any help on this is appreciated.

FATAL_ERROR System.JSONException: Expected DocumentRetrievalResponse.ContentElementsInfo but found [line:1, column:2444]

PS: if I comment the declaration public ContentElementsInfo contentElementsInfo get;set;, the deserialize happens fine but without ContentElementsInfo.

You seem to have a typo in your class.

cecDocumentRetrievalResponse()

should be
DocumentRetrievalResponse()

If I use your same DocumentRetrievalResponse class, remove the cec and use your JSON I can run your lines and it works for me. I made no changes to your code.

String result = '"searchDocumentsResponse": "documentsIndexInfo": ["contentElementsInfo": "fileName": "test.pdf","fileSize": 1010694,"indexNumber": 0,"mimeType": "application/pdf","guid": "123456789-1234-1234-1234-92393300000","majorVersion": 1,"minorVersion": 0,"objectStore": "09876543212-1234-4B53-8CC5-469444E92456","pathName": "","properties": ["multiValue": false,"name": "Document_Type","type": "STRING","value": "TEST","multiValue": false,"name": "ScanTMSTMP","type": "DATE","value": "5/16/1920","multiValue": false,"name": "f_DocNumber","type": "STRING","value": "","multiValue": false,"name": "MimeType","type": "STRING","value": "application/pdf","multiValue": false,"name": "DateCreated","type": "DATE","value": "5/31/2018"] ],"numDocObjectsFound": 1,"numDocObjectsReturned": 1,"responseStatus": "code": "OK","message": "","startingDocObject": 0';
System.Type resultType = System.Type.forName('DocumentRetrievalResponse');

DocumentRetrievalResponse deserializeResults = (DocumentRetrievalResponse)JSON.deserialize(result, resultType); 
System.debug('deserializeResults ' + deserializeResults.searchDocumentsResponse.documentsIndexInfo[0].contentElementsInfo.fileName);