We would feel safer at Windsor Hills than the Old Towne area. The resort itself is 24 hour manned gated and very secure. We love taking walks there. Never had any concerns. Never had any concerns on the 192 area for shopping, etc., lots of restaurants and Super Target, Walmart, etc. Of course you would need to drive to shopping, restaurants, etc. There is a small store in the resort that sells items, sandwiches, quick meals, wine and beer and a bar area right outside the pool where you can sit and have your meal/drink/etc. There are lots of posts on here about Windsor Hills, never heard of any saying area was not safe. You of course are tourists and should take precautions wherever you stay and in any shopping area.
Sandy