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Our History

Note...The following article was written by Mr. Irv Denton, and appeared in the Sleepy Hollow Woods year 2000 Directory.  It has been slightly edited.

Sleepy Hollow Woods by Irv Denton

"Facts" offered in this history come from Fairfax County publications, newspaper articles old and new, interviews with knowledgeable individuals, and hearsay from trustworthy sources. The third floor of the Fairfax County Regional Library in downtown Fairfax City contains the Fairfax County Historical Society’s collection of reference material.

Since Sleepy Hollow Woods occupies land, its ownership must be traced back to original "legal" land records. The Atlantic coastline was claimed by earlier explorers for the then King or Queen of England. Charles II, in 1649, granted some five million acres of Northern Virginia to a "proprietorship" of seven English noblemen, one of whom was Lord Fairfax. The seven "proprietors" could build or establish any normal activities upon the land and could legally sell it. The colonial government at Jamestown in 1660 began contesting Northern Neck land ownership and issued land grants for some of the same acreage.


None of the proprietors paid much attention to their unsettled and undeveloped land until about 1719. By this time, Thomas, the sixth Lord Fairfax, owned all the shares of King Charles’ original land grant and had appointed his cousin, William Fairfax, as customs collector and land grant agent for the South Potomac River area. The Virginia government at Jamestown still contested the Northern Neck land ownership. To settle the controversy, the sixth Lord Fairfax came to northern Virginia, had his land surveyed, and selected for his own retention some 12,588 acres of land near Great Falls. Lord Fairfax moved to Virginia, lived with his cousin William at Belvoir for a while, then moved to Frederick County in 1761. When he died in 1781, all his land sales and grants were declared legal and the remainder reverted to the Commonwealth of Virginia.

The land in northeastern Virginia was possibly the least fertile in Virginia and was among the last to be cultivated and developed. Being in the Potomac watershed the topsoil was thin and rocky: deep ravines were numerous. Not until tobacco became popular in Europe could local land support a cash crop sufficient for clearing, cultivating, settlement, and development.


Tobacco crops soon depleted the local cropland and it was sold and resold in ever-smaller plots for small, subsistence farms. During the World War I period, dairy farming became profitable and popular. The immediate Sleepy Hollow area is badly scarred with deep ravines. Level areas for pasture and crop fields were scarce and difficult to develop. The Barcroft area ravines were dammed at Columbia Pike and the resulting lake served as Alexandria’s water reservoir until after World War II.


During the following decades, federal government activities generated crowded housing conditions in the District of Columbia, and the Annandale area became popular for "suburban" living. Family homes for former Alexandria, Arlington, and D.C. residents were built on one- to five- acre lots. Residential area roads were scarce, narrow, and dirt!

In the early 1950’s, residential developers became active in Annandale. The McWhorter family bought twenty acres of jungle from a Mr. Chatelain, built the Annandale Shopping Center on the front six acres, and sold the remainder to the Chatelain Village developers. The Oliver family sold their 32- acre dairy farm for the Broyhill Crest development. Columbia Pine was developed from an assemblage of large lots, as was Sleepy Hollow Woods. A "holdout" from Columbia Pines was the Webb family home-place on top of the hill at the intersection of Gallows Road and Columbia Pike. Until a very few years ago the old house, yard, and the old fruit trees remained invisible to passer-byes because of its hilltop site. Now we notice twelve highly visible homes known as "Webbmont."


Those of us who have researched our land deeds in the Fairfax County Land Records Office will find several family names listed as having transferred their multi-acre lots to the Sleepy Hollow Woods developers. Although initial construction of model homes were on Moss Drive and not built and occupied until 1959, a U.S. Geological Survey Map dated 1945, shows an Annandale street plan which includes most of Sleepy Hollow Woods’ streets and courts. Some of the latter are unnamed, and some are not shown at all.

The Dewberry & Davis architects designed four different Sleepy Hollow Woods floor plans and assigned them to appropriate lots. The lots were sold to various construction firms for actual building. The several construction firms were represented "on-site" by Community Builders and I.L. Lewis Realtor Associates at "816 Moss Drive." (Lots have since been renumbered).


The home designs were named RALEIGH, WAKEFIELD, YORKTOWN, and WINCHESTER. Residents today identify them, in sequence, as Rambler, Bi-Level, and Split-Level. The Yorktown and Winchester both are "split-level" and look much the same but with different floor plans. (The Winchester front entrance is flush with the outer wall; the Yorktown entrance is recessed.) Selling price for the Yorktown was $24,990, for the Winchester, $24,490, for the Raleigh, $23,990, and for the Wakefield, $22,490. Maximum down payment was $3,790; maximum monthly payment was $138. Carports could be added for $700 extra.

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