Judith Bayle…, Both Buyer and Seller in Connecticut

Mt. Sterling vs. Winchester

Asked by Judith Bayless, Connecticut Thu Sep 25, 2008

We are planning on retiring to a small town in KY and have narrowed the list to possible Mount Sterling or Winchester. We want a cheap older home with potential. Potential is only possible if the neighborhood can take upgrades and not be over built for the area.

Any suggestions on the best place? Thanks!

Help the community by answering this question:


It depends on what's important to you. Both Winchester and Mt. Sterling are nice small towns with low crime rates and a nice atmosphere, so you've narrowed your choices well. One big advantage Winchester has over Mt. Sterling, however, is its proximity to major shopping and entertainment outlets in Lexington. One of the largest shopping areas in Lexington is situated just off I-64 on the Northeast side of Lexington, so it's literally 15 mins. from Winchester. In Mt. Sterling, you'd have to travel about 40 minutes to get to any major shopping/entertainment venues.

Also, you may find it easier to locate a home in Winchester because most homes for sale in that area are listed in the Lexington Area MLS, whereas many homes for sale in Mt. Sterling aren't listed in any central database (many agents in Mt. Sterling aren't members of the area MLS) so it's harder for you to get a true idea of everything that's on the market in Mt. Sterling, especially from far away.

Obviously, you can tell that as an agent, I favor Winchester, but having said that, both communities are nice smaller towns to live in and I don't think you could go wrong with either one.

If you'd like to search the MLS for homes for sale in Winchester, KY, just visit my website below.
1 vote Thank Flag Link Thu Sep 25, 2008
All of the historical areas in Mt Sterling can be upgraded if you get approval from the historical society.
0 votes Thank Flag Link Thu Feb 13, 2014
I lived in Mt. Sterling for many years and my sister in law just moved there after spending 14 years in winchester. Both places you can find nieghborhoods with lots of potential. They are both very nice places to live. Really in this case YOUR personality should be the deciding factor. Mt. Sterling is more of a laid back relaxing kind of city while Winchester is more for fast paced on the go kind of people. I hope this helps you with your decision. If there is anything else you wouldlike to know about this area you can get me at my email hedge.dana@yahoo.com. I would hate to see anybody move somewhere and then not be happy with thier decision.
Good luck with your hunt,
0 votes Thank Flag Link Sun May 10, 2009
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