Part of what the Roland Park Company called "The District" in a 1928 sales book, Homeland was laid out by the Boston firm of the Olmstead Brothers, who had earned much praise for the design of New York's Central Park. Streets meander, and street vistas are open, unobstructed by fences and hedges. Utilities and services are brought in from the rear to avoid unsightly poles and lines marring the open view.

As the third community developed by the Roland Park Company, emphasis was placed on landscape design integrated into the house plan. Covenants were more restrictively written, apparently to correct what the Roland Park Company saw as design flaws in their earlier deeds.

The major highlight of the community is the open space, owned by all dues-paying Members of the Association. These open spaces include the historic lakes in the center of the community, originally spring-fed and dug by the original owner of the estate. Additionally, meandering streets and lanes and large specimen trees take you back to a more gracious time. Houses of all types, built only with natural materials to blend with the landscape, abound. Spring provides a vista of flowering shrubs and trees throughout the neighborhood. The placing of the utilities, services and garages in the lanes opened up the vistas of lawns, gardens, patios and terraces in the front, while hedges and fences add to privacy in the rear. Neighborhood events such as the Resident Picnic in the summer, the Halloween Parade at the Lakes and the Homeland Children's Choir Christmas Eve at the Lakes help to keep residents involved. Homes currently range in price from the mid-$200,000s for smaller or duplex homes to more than $1,500,000. In 2005, the average sale price was about $570,000.

There is a great diversity of architectural styles and materials in Homeland. Styles include Norman, Tudor, French Country, Spanish Revival, Early American and Colonial. Then, as now, plans had to pass a severe test in front of the Architectural Committee. To quote the sales brochure "the Roland Park Company's architectural committee prevents freakish, or even extreme manifestations of taste, not only in regard to lines and mass but color." Thus, the majority of homes in the Community today are as lovely as when they were originally built. The Roland Park Company ensured that their vision would be maintained by hiring the well know architect, William Lamdin, to design several "spec" houses. The firm of Palmer & Lamdin is thus very well represented in Homeland. Other famous architects were William Gordon Beecher, Cyril H. Hebrank, Fournoy and Fournoy, Machen and Dixon, Addison F. Worthington. Because it was felt that the landscape was equally important in the design of a home, there were "spec" landscape plans executed as well. In fact, the Roland Park Homeland Company maintained a garden lot in the 100 block of Enfield Road for a number of years to show what was expected of new homeowners.

The neighborhood currently known as Homland can be traced to a tract of land called "Job's Addition" surveyed by Job Evans in 1695. Further land was added in 1778. David Maulden Perine purchased the original property and added to it, so that by 1875 it finally reached its present size.

One of the original planned communities in the U.S., Homeland was developed by the Roland Park Homeland Company who purchased the 391 acre parcel, then know as the Perine Estate of Homeland, in 1924 for the sum of $1,000,000. The advantages of the location of the property included the fact that its highest point sat more than 400 feet above sea level, thus making it one of the more elevated sections of Baltimore. Additionally, the rolling terrain (and subsequent naming of the streets) evoked the English flavor the Company wished to portray. The new development of Homeland was advertised in the Sunday Sun in 1924, with the sale opening at 8:00 a.m. on Sunday, 11th October 1924. At that time everything was still in the paper stage. Despite that, at the end of the first day, 89 lots had been sold. At the termination of the sale 16 days later, the number rose to 248. The first house approved by the Company was in 1924, built in 1925 - 5108 Springlake Way. In 2001, Homeland was entered into the National Register of Historic Places. Not only does this acknowledge Homeland as a premier example of American suburban development, it provides residents with tax credits to restore their homes with historically appropriate materials.