Sandra Stanton transcribed and submitted the following Washington County Deeds in Feb 2007. I've added some comments.

Joseph Gray to William Cooley, 1795

Both Joseph Gray and William Cooley removed to Stewart County, Tennessee by 1806. -MC

Washington County Kentucky Deed Book A, Page 290

This Indenture made this 6th day of August one thousand Seven hundred and
Ninety five Between Joseph Gray of the County of Washington and State of
Kentucky of the one part and Wm Cooly of said County and State aforesaid of
the other Part  Whitnesseth that the said Joseph Gray for and in
consideration of the Sum of Fifty pounds to him in hand paid have granted
bargained and Sold   by these Presents do grant bargain and Sell unto the
said Wm Cooly and his Heirs and assigns forever one certain tract of Land
Containing fifty two acres Situate lying and being in the County of
Washington on the Waters of the North fork of the Rolling fork on the North
Side thereof and bounded as follows  (To Wit) Beginning at a honey locust
and runing north 58 East 31 poles to a honey locust tree on the bank of the
Rolingfork. Thence North 24 west 190 poles to two Dogwoods thence South 45
west 66 poles to a Dogwood and maple thence S 33 East 173 Poles to the
Beginning be the Same more or less  To have and to hold the said tract of
land and the appurtenances thereunto belonging unto the said William Cooly
his Heirs   assigns forever and the said Joseph Gray for himself and his
Heirs the aforesaid tract of Land with its appurtenances unto the said
Joseph Gray his Heirs   against the claim of Every other person whatsoever
will warrant and forever defend said Land In Witness whereof the said Joseph
Gray has hereunto set his hand   affixed his Seal the Day and date first
above written
TEST
Jno Caldwell
Jos. Gray     (SS)

At a Court of quarter Sessions held for Washington County the 6th day of
august 1795

This Indenture was acknowledged by the within named Joseph Gray to be his
act and Deed   ordered to be Recorded 

Testes: John Reed

Joseph Gray to Anne Cooley, 1803

Anne Cooley was the wife of William M Cooley, later of Stewart County, Tennessee. It's believed she was Joseph's daughter. So far as I know, proof of that has yet to be found but further evidence is found in the 1812 Stewart County deed, "Joseph Gray Sr., deed of gift to Joel Cooley, son of William Cooley" (see Stewart County Cooleys for more information). -MC

Knew all men by these presents that I Joseph Gray of Washington
County State of Kentucky for and in consideration of divers valuable
Services rendered & performed for me by Anne Cooley wife of William
Cooley of the County aforesaid and for the further consideration of five
shillings current money of the State aforesaid to me in hand paid by the
said Anne Cooley the receipt whereof I do hereby acknowledge Have Granted
Bargained and Sold and by these presents do give Grant bargain sell and
deliver unto her the said Anne Cooley and her heirs forever a certain negroe
Girl Slave named Betty and her future increase and I do hereby Warrant and
defend the Said Negro Girl Betty and her future increase unto the said Anne
Cooley her heirs and assigns forever free from the claim or demand of all
and every person or persons Whatsoever & Free and Clear from all
incumbrances of any Kind Whatsoever In Witness whereof I have hereunto Set
my hand and affixed my seal this 18th day of November 1803.  Joseph Gray
seal

William Cooley to Bird Lawless, 1804

Joseph Gray also sold land to Bird Lawless in 1804 [Link]. I'd surmise that the Grays and Cooleys were preparing for their removal to Stewart County, Tennessee. -MC

Washington County Kentucky Deed Book C

This Indenture made this sixth day of April eighteen hundred and four
between William Cooley of Washington County and State of Kentucky on the one
part and Bird Lawless of the County and State aforesaid of the other part.
Witnesseth that the said William Cooley for the consideration of the sum of
one hundred pound to him in hand paid have bargained and sold unto Bird
Lawless his heirs and assigns forever a Certain tract of land lying in the
County of Washington containing fifty two and one half acres of land being a
part of the tract of land Joseph Gray now lives and including the plantation
where William Cooley now lives and bounded as follows (To Wit) Beginning at
a honey locust and running North 58 East 31 poles to a honey locust tree on
the bank of the rolling fork thence North 24 West --- poles to two dogwoods
thence 45 West 66 poles to a dogwood and maple thence South 33 East 173
poles to the beginning To have and to hold the aforesaid tract of land and
the appurtenances thereunto belonging unto the said Bird Lawless his heirs
and assigns forever and he said William Cooley his heirs and assigns do
forever warrant and defend the above mentioned tract of land with every part
belonging thereto unto Bird Lawless his heirs and assigns forever from the
right title or claim of all person or persons whatsoever laying any claim
thereto In Witness whereof the said William Cooley hath hereunto set his
hand the day and year above written.

Wm. Cooley seal
Amy Cooley seal

Witnesses present
Benja. Lawless
Andrew Given
Burton Lawless

Washington County Oct 1  John Read Clerk of he County Court for the County
aforesaid do hereby Certify that on the day of the date thereof This
Indenture was acknowledged before me in my office by the within named
William Cooley and Amy Cooley his wife (she being first privately Examined
as the law directs she relinquishing her right of dower) to be their act and
deed and thereupon admitted to record. In Testimony whereof I have hereunto
set my hand this --- day of October 1 04.

John Reed

Absalom Baker to Pyrin Cooley, 1810

Washington County Kentucky Deed Book 5, page 524

THIS INDENTURE MADE this day of June 1810 Between Absalom Baker of
Washington County and State of Kentucky of the one part and Pyrin Cooley of
the said State and County of the other part. Witnesseth that the said
Absalom Baker for and in consideration of the sum of one thousand Dollars to
him in hand paid the receipt whereof he doth hereby acknowledge hath given
granted bargained sold aliened and confirmed and by these presents doth give
grant bargain sell alien   confirm unto the said Pyrin Cooley and his
heirs forever one certain tract or parcel of land containing one hundred and
thirty seven acres be the same more or less situate lying and being in
Washington County on the waters of the Rolling forks and bounded as follows
To Wit Beginning at a white oak and sugar tree thence south 242 poles to a
white oak and beech thence East 100 poles to two white oaks thence North 197
poles to a red oak and Elm thence North 65 W 102 poles to the Beginning with
its appurtenances To have and to hold the said tract or parcel of land with
its appurtenances to the only use and behoof of him the said Pyrin Cooley
and his heirs forever and the said Absalom Baker for himself his heirs
Executors administrators and assigns the said land premises unto the said
Pryin Cooley and his heirs shall and will forever warrant and defend the
claim or claims of him the said Absalom Baker and his heirs or any person or
persons claiming under him or them. In Testimony whereof I have hereunto set
my hand and affixed his seal the day and year above written.

Absalom Baker      (seal)

Washington County Sct I John Reed Clerk of the County Court for the County
aforesaid do hereby certify that on the day of the date hereof This
Indenture was acknowledged before me in my office by the within named
Absalom Baker to be his act   Deed In Testimony whereof I have hereunto set
my hand this 10th day of June 1811
John Reed

A Copy Attest:  John M. Smother, Clerk Washington County Court.

Pyrin Cooley to John Condor, 1811

Perrin Cooley moved to Missouri with two of his brothers in 1811. This may be the same year that their father John died, probably in Casey County. -MC

Washington County Kentucky Deed book D, pages 94-95

This Indenture made on this twenty ninth day of September AD Eighteen
hundred   eleven between Pyrin Cooley of Washington County and State of
Kentucky of the one part and John Conder of Casey County and State aforesaid
of the other part  Witnesseth that for and in consideration of the sum of
four hundred dollars to him in hand paid the receipt whereof he doth hereby
acknowledged and himself therewith to be satisfied hath granted bargained
and sold and by these presents doth doth grant Bargained sell align and
forever Ratify unto the aforesaid John Conder his heirs   assign or assigns
one certain Tract of Land Containing 137 acres be the same more or less
situated lying and being in Washington County on the Waters of the Rolling
fork and bounded as follows (To Wit) Beginning at a white oak and sugar tree
thence South 242 poles to a white oak and beech Thence East 100 poles to two
white oaks thence north 197 poles to a red oak and Elm thence N 65 . W102
poles to the beginning with its appurtenance to have and to hold the said
Tract of land to the use   behoof of the said John Conder his heirs or
assigns forever and the said Pyrin Cooley doth by these presents and for and
in considerations of the about mentioned sum the payment and receipt whereof
__ is entirely satisfied with will ever warrant   defend the said parcel of
land against his heirs   or any person or persons whosoever claiming __
through or under them __  Witnesseth whereof the said Pyrin Cooley doth
himself set his hand and seal this day and date above written

     his
Pyrin X Cooley
     mark
                  
     her
Sarah X Cooley
     mark 
      
Signed sealed   delivered in presence of
William Bigger
Robert Russell
William Followell

Washington County Sct  I John Reed and Clerk of the County Court for the
county aforesaid do hereby Certify that on the day of the date hereof this
Indenture was proven before me in my office to be the act   deed of the
within named Pyrin Cooley   Sarah Cooley by the oaths of William Bigger
and Robert Russell two of the subscribing Witnesses thereto and thereupon
admitted to Record In Testimony whereof I have hereunto set my hand this 9th
day of March 1812 John Reed