Easton or Chestertown?? (Annapolis, Ocean City, Stevensville: house prices, college, pros and cons)

[macdebbie]

We are contemplating moving from the North (MA) a little further South to escape the long, cold winters, and extremely high cost of housing. It won't be for a few years yet as we are not that close to retirement.

Our first trip to MD we are staying in Easton (it sounds interesting) and visiting Chestertown and St. Michaels and Oxford.

St. Michaels and Oxford are too small for us, and St. Michaels too expensive.

But Chestertown sounded really interesting.

We're looking for a vibrant community - festivals, etc. going on, a nice downtown, safe, close to a good hospital, not super expensive (we are in the range of 350K - 400K), historic, aesthetically pleasing.

Would love to know the pros and cons of both places.

[macdebbie]

Does anyone know any nice subdivisions we could visit while we are in MD in March?

Cooke's Hope looks beautiful but it is too expensive for us.

We like planned communities with the trees still intact and houses not right on top of one another.

[Njrover0216]

Where do you plan on working? There other nice towns over there besides those two, di you consider Centreville,Greensboro, Denton and Stevensville. I would prefer to live in Chestertown over Easton, if you would like to know why feel free to PM me, I have friends that live in Easton and after what they told me we decided to stay on this side of the bridge.

[RavensFan0606]

Although a small community, Chestertown is a nice, quaint little town with a lot of history. I will be calling it my home for the next 4 years starting this fall, attending Washington College.

[MikeinMD]

I prefer Easton over Chestertown. Easton has more shopping, restaurants, and a nice downtown area. In Chestertown you get stuck on 2 lane Rt. 213 all the time. Easton does have more problems with traffic, especially on weekends in the summer but once you learn the other roads its no big deal. While Easton is small, I think Chestertown is just too small. However houses in Chestertown are much cheaper.

[theprez]

Both offer the historic downtown feel... Easton is right on Rt 50 (your main route to Ocean City in the summer) and Chestertown is about 45 mins off of rt 50.

I think Chestertown offers more of a secluded feel, since Easton is right on rt 50 and a lot more traffic.

[MSLauren]

Easton is more on the main highway so easier access to various places. Chestertown is a bit more historic and is right on the river. Why were you not interested in St Michaels? It seems to be everything you are looking for and is a gorgeous area. Also you might like to consider Kent Island, probably the Stevensville area. There isnt too much of a historic part to the island but there is plenty to do being that close to the bridge and Annapolis although house prices have gone up quite a bit. There are several small towns throughout the eastern shore that all have their own good and bad points.

[macdebbie]

Definitely interested in St. Michaels, but had read that it was outrageously expensive. It also is much, much smaller than we were looking for, but I guess it is near enough to other communities.

What is Oxford like?

Ditto for Stevensville. Plan on stopping there on our way over to Easton. Didn't know if being on an island would be a hassle getting places, or feel isolated.

We will have a better sense when we come out what we like.

Thanks all.

[bawlmer]

Chestertown

[desilu]

What happened in Easton?