Ralph Drees, president of Drees builders and developers, had a creative vision to develop a large housing community. Boone County's flat to gentle-rolling land made it ideal for residential development and this location was near the Florence Mall which opened in 1973. Land was purchased off route 18 bordering Gunpowder Creek, and the Oakbrook development was started. Development included apartments, condominiums, single family houses and the Oakbrook market place. Oakbrook Drive is the main street that links the many parts of the development and provides access to Pleasant Valley Road and SR18. The Oakbrook community is one of Drees' largest and most successful developments.

The picturesque community, located in a natural setting, was started in 1978. The first phase to be developed was "The Wynds", with the pool and clubhouse, followed by buildings on Cliffside Drive.  Brookview Drive, Windy Court and Gale Court were constructed over the next few years. The next phase of construction, "The Fairways", occurred off Wynds Drive.  Summerfield Drive, Green Leaf Court, Glendale Court, Linkview Drive, Greens Edge Drive, Trapside Place, Englewood Place, and Shady Cove Lane.  Shady Cove Lane was the last street to be developed in "The Fairways." Construction continued with the development of the final phase, "The Cliffs." The pool was constructed; then buildings followed on Sweetwater Drive , Cliffview Dr. and Cascade Drive.  The last building was completed in 1993. Collectively, this development is known as "Wynds at Oakbrook".

There are 101 residential buildings with 558 individual living units, 2 swimming pools and 2 tennis courts.  In 2001 a third tennis court was converted into a basketball court. The clubhouse is located in "The Wynds" on Cliffside Drive.  Members can rent the clubhouse for private parties.  A storage area for boats, campers, trailers, etc. is located off Oakbrook Drive near Wynds Drive, adjacent to Gunpowder Creek.

The Declaration of Covenants, Conditions and Restrictions of Ownership was signed on April 27, 1979, and the Wynds At Oakbrook Homeowners Association, a non-profit corporation, was formed. There are nine volunteer homeowners on the Board of Directors with three Directors elected each year at the annual meeting in February.

The annual meeting is held the third Thursday in February. The community publishes a newsletter and also maintains a website (www.wyndshoa.com).  The Association contracts a property management company, Towne Properties Asset Management Company, to manage the operations of the community.