Windsor Hills derives its name from the Windsor Mill, an 18th century grist mill that was located on the Gwynns Falls, probably at the Windsor Mill Road bridge. The site of this bridge was described in 1757 as "William Miller's Ford", implying the existence of a homestead that may have included a mill. The date of construction of this long-vanished mill is unknown, but first appeared in documents, as being for sale, in 1784. At about that time the Windsor Mill was described as a three story structure with three waterwheels. The mill was last mentioned in documents in 1818, and soon thereafter a mill downstream, in today's Rosemont area, took the Windsor Mill name. Windsor Mill Road obviously also derives its name for this mill, although it existed as a nameless local thoroughfare connecting farms west of today's Dickeyville area with the Garrison Road, as early as 1730.
Parts of today's Windsor Hills area were patented as land grants as early as the 1690's, with the enormous 2000 acre "Parishes Range" tract including the northern portion of Windsor Hill, and "Crowley's First Venture" including a southern portion adjacent to the Gwynn's Falls. However, due to the hilly terrain, Windsor Hills was unsuitable for farming, and early settlement in the area was very sparse. Other than the Windsor Mill, the only 18th century settlement of note in the area was the Tschudi Mill, constructed in 1770 along the Gwynn's Falls, upstream. This mill was closer to the Dickeyville area than to Windsor Hills, and the history of the Tschudi settlement is described in the Dickeyville neighborhood history.
By the mid-19th century all or part of the estates of several families included parts of the Windsor Hills area. West of today's Chelsea Avenue, north of Windsor Mill Road, Mrs. Adele Bujac and Mr. Alfred Bujac built adjoining schools -- "Monticello," for girls, and "Tusculum" its twin to the west, for boys. A southern portion of Windsor Hills was owned by Thomas Winans whose "Crimea" estate was located nearby, in today's Leakin Park just east of Franklintown. Much of the northern portion was part of Jesse Slingluff's "Oakfield" estate (not his primary country estate, which was "Beech Hill" in toady's Walbrook area). The middle portion approximately between today's Fairfax Road and Bateman Avenue as part of George Repold Vicker's "Mount Alto" estate. Most of the Slingluff and Vickers properties were later developed as Forest Park and Walbrook.
In the years following the Civil War, the Bujacs' schools were sold and converted to private residences -- Tusculum sold to Charles Hilgenberg and Monticello to William Prescott Webb. These estates continued to be owned by these families until well into this century. Tusculum was bought for residential development in 1911, and Monticello was bought by the City in 1925 and razed for the construction of Windsor Hills School.
In 1889 Edwin Tunis, the first pioneer of modern Windsor Hills, bought property in the area. Mr. Tunis both built his own residence in Windsor Hills and contributed greatly to the early development of the community. The North Avenue Land Company, and the Windsor Park Company, both of which Edwin Tunis helped found, were responsible for the early development of Windsor Hills.
In 1896 the Winans property just north of the Gwynn's Falls was bought, and by the end of the century the first few houses were constructed. The first house to be built in Windsor Hills was known as "The Cliffs," a large brown shingled Victorian house backing on the Gwynns Falls valley. Much of the foundation stone and terracing for The Cliffs came from an abandoned nearby 18th century grist mill, possibly the original Windsor Mill. By 1906 about twenty houses had been built, primarily along streets south of Queen Anne Road. Early streets, such as Queen Anne, Prince George, and Talbot Roads were named after Maryland counties.
As with much turn-or-the-century residential development in Baltimore City, the growth of Windsor Hills coincided with improvements and extensions to nearby public transportation lines. In 1870 the Baltimore, Calverton and Powhatan Railway started a horse-drawn streetcar service from the terminus of the Red Line, where connections could be made to and from the downtown, west through Walbrook, and along Windsor Mill Road to the mill village of Powhatan, which existed just outside today's Baltimore City limits at the site of Woodlawn Cemetery. The BC&P never provided more than marginal service, yet it was greatly missed by local residents when it discontinued its Windsor Mill Road route in the early 1890's. To compensate for this loss, affected patrons created in 1894 an electrical trolley line, the Gwynns Falls Railway, which ran about a mile along Windsor Mill Road from Walbrook Junction to the Gwynns Falls. This line was taken over by the (Baltimore?) Traction Company in 1897.
Other streetcar service was also available by the this time on Garrison Boulevard. The Tunis family was involved with the creation of the Gwynns Falls Railway, which was originally planned as a monorail, along the innovative designs of Howard Hansel Tunis, an engineer and nephew to Ed Tunis. An experimental circular-tracked monorail was eventually built about the turn of the century on Tunis property, near the intersection of today's Prince George and Lawina Roads. Howard Tunis and a son of Edwin each designed plats for Windsor Hills. Innovative for the time, there plans created lot lines that took advantage of the natural contours of the land.
As with Howard Park and Gwynn Oak Park to the northwest, Windsor Hills had in the 1890's the contemporary establishment of an amusement park and electric trolley service to the area. Ridgewood Park was a small park offering swings, a merry-go-round, and other amusement, and existed for a short time on the Windsor Mill Road in Windsor Hills. So short was its existence that its precise location is unknown today.
Development increased in Windsor Hills, especially north of Loudon Avenue and Alto Road, during the teens and 1920's, with almost all houses built in the single family detached, wood frame and shingle cottage style. A 1916 newspaper advertisement described cottage lots for sale in Windsor Hills as being "restricted against rows of brick buildings, saloons, and all nuisances." A few rowhouses were built in Windsor Hills, with a group of Daylight houses in the 4000 block of Clifton Avenue advertised for sale by James A. Bealmear and Son, in 1929. The Windsor Hills Improvement Association was formed during the early days of the community, and served primarily a social function for the somewhat isolated early suburban pioneers. After a dormant period, the association revived in the 1950's to fight undesirable zoning changes, to protect property owners from unscrupulous block busting real estate salesmen, and to promote orderly integration of the community.