I have lived in Winchester since 1974 and pretty much what the above poster has said I agree with. But there are few things I have to add about Winchester and Frederick County...
For starters it is actually quite easy to find a place there. Not many places there do credit checks. My sister for example has HORRIBLE credit. Even been evicted from a few places. Yet she still had no problem finding a place to live in Winchester.
A married couple should have no problem finding a place in Winchester. Neither should a single person living by themself. However if a man/woman plans on moving to the area and plan to share a house with a bunch of their buddies, then they may have to consider moving elsewhere as both Winchester and Frederick County in recent months have put rules in to place that regulate how many unmarried adults can live in one home.
There is actually a debate as to why they are doing this. Some say its to target the growing number of hispanics moving to the area, others believe its a "gay" thing ( I have had many gay friends who have since left this area and they all swear Winchester is the most homophobic city out there, the local paper Winchester Star does shine some light on this ). And yet there are others who believe both the city and county want to control growth . I think the latter is the case.
As I said earlier I have lived in Winchester since 74, while it is a good area, it does have a few drawbacks. Winchester may very well have the worst public transportation system in the nation. For starters the buses dont travel into Frederick County which I believe is a major mistake.
In other threads I have read about the lack of traffic in Winchester. I beg to differ on this. For a town of 25,000 ( 40,000 if you add all the new developments that have been build around the city limits of Winchester ), Winchester does have it share of traffic woes. Enough so that most of the local radio stations there like WINC-FM were forced to start airing traffic reports.
Winchester is home of the Shenandoah Apple Blossom Festival. That is both good and bad. Good for all the money it brings to the area, bad if you have no interest in parades, carnivals, has-been celebrities ( Wayne Newton for example ), massive traffic or crowds. Banks, many retail stores and even schools shut down for this which makes Winchester a horrible place to do business for those few days in May.
Winchester area media is both good and bad. Winchester's radio scene is actually better than many large metro areas. The two newspapers, not so good. The Winchester Star is very ultra conservative while the Northern Virginia Daily tend to get graphic in their news coverage. Also forget getting a local Sunday paper there. Both papers refuse to publish on that "day of rest".
Televison in Winchester gets interesting. Last March Winchester got its first TV station. ABC 3 !!. There website is
TV3 - Home Winchester - tv3winchester.com After years of being ignored by the TV stations in DC, Baltimore and even Hagerstown, Winchester finally has a newscast to call its own. But as always with the good comes the bad. Last year the FCC approved plans as a result of the debut of Winchester's channel 3 of taking Winchester and Frederick County out of the DC TV market and place it into nearby Harrisonburg's. Once that happens one might as well forget about watching any television out of Washington or Baltimore. Unless of course one plans on installing an antenna on top of their roofs, but be warned many homeowners groups in Frederick County have gone after those who chose that route. But then again local TV is among the least of one's concerns when moving to a new area.
Retail and restaurants in Winchester...all of the main stores are already there, if not they are coming soon. Same with restaurants. Winchester does have a nice sized mall..Apple Blossom Mall. However the mall's owners Simon is planning to re-do the mall into a mix of a lifestyle center and keeping a much smaller part inside. Rumor has it that Macys is coming to Winchester, which I am sure will please many.
Neighborhoods in Winchester, most I found to be not that bad. Yes there are a few rough spots but not a whole lot of them. And if one can't find what they want in Winchester, I am sure one can find something in Frederick County.
On a scale of 1 to 10, I give this area an 7. There are problems here but the good outweighs the bad.