Genealogical researchers with ties to Chesterfield County, South Carolina do not have to be reminded of how difficult research is in that County. This posting will focus on Probate records and will be geared towards new researcher just beginning their search in Chesterfield County.
Availability of records is problematic; mostly due to the destruction of pre-Civil war records.
Here are a few sources for early genealogical information on inhabitants of Chesterfield County.
The first is a Book published by James C. Pigg in 2000. The title of this book is “Cheraw/Chesterfield District Wills, 1750-1865 & Abstracts from the Court of Common Pleas 1823-1869.” (C18)
This book consists of three sections:
Section 1, pages 1-35 – Colonial Will collected by Dr. Lloyd Johnson & James C. Pigg
Section 2, pages 36-114; WILLS from Chesterfield County, Will Book 1
Section 3, page 115-138; genealogical material extracted by Jim Pigg from the Court of Common Pleas Records.
Another source for pre-civil war genealogical information is another book by Mr. Pigg entitled “Miscellaneous Abstracts from Pre-Civil War Cheraw Newspapers”  (C6)
Mr. Pigg's books can be purchased from Old Darlington Genealogical Society.
Post Civil War probate records are available and those up to the early 1900 can be found on-line at: https://www.familysearch.org/
These files contain info on the personal property and inventories of goods for the estate, monies owed the estate, care of minor children, and in some case WILLS are included. Just because there is a probate file does mean it will contain a WILL.
These files on FamilySearch are in two groups.
The first group of records is the alphabetical index of all probate folder. They are filed alphabetically by Surname.
The second group is the Estate Folder themselves.
I wrote about access to these files back in January 2012. Please revisit this link:
Information of a social nature can be found in the “History of the Old Cheraws”; “Rambles in the Pee Dee Basin” and “Reminiscences of Early Life in South Carolina”.  
I am not aware of any other source for pre-civil war genealogical information on Chesterfield County families. I have been successful in finding additional information in the equity records. Information that was not previously published in the books or webpages listed above.
 James C. Pigg, Cheraw/Chesterfield District Wills, 1750-1865 &: Abstracts from the Court of Common Pleas 1823-1869 (Washington, D.C.: self-Published, 1995), 1.
 James C. Pigg, Miscellaneous Abstracts from Pre-Civil War Cheraw, South Carolina Newspapers (Tega Cay, South Carolina: James C. Pigg (self-Publish), 1998).
 Right Rev. Alexander Gregg D.D., History of the Old Cheraws (Columbia, South Carolina: The State Company, 1925).
 Harvey Toliver Cook, Rambles in the Pee Dee Basin South Carolina (Columbia, South Carolina: The State Company, 1926), 1.
 David Gregg McIntosh, Reminiscences of Early Life in South Carolina (Florence, South Carolina: Saint David's Society, 1985).
 Darlington County, South Carolina, Equity Records, Film #DA24 Second Section, Pages 0000-0014, Bill #13. Alex Melton and Edith Lundy alias Edith Wages, J. J. Evans, Defts Solc,; "Darlington Equity Records," digital images, South Carolina Archives & History (http://scdah.sc.gov: viewed and copied May 2000); filed February 12, 1821.