I wanted to stay within walking distance to all the beautiful shops and restaurants in downtown Winter Park and this location was perfect. Yes, the hotel is old but it has so much "character" between the vintage elevator, gift shop and treasures in the lobby. It's also wonderful to sit on the balcony, have a glass of wine or cup of tea while overlooking the Central Park or street.
The staff was very helpful with anything I needed. Be sure to ask if you have issues with getting on to the WiFi. Once I was shown how to do it, it was fine. There is a charge for the Valet Parking but it's worth the convenience in a place like this where parking is difficult and the drivers can be a little crazy.
I read some reviews that complained about the train or street noise. To me, that is part of the charm of staying in a place like this. It reminded me of the smaller hotels I stayed at when I've traveled in Europe or Canada. I prefer hotels like this to chain type places.
Having said that, a few minor touch-up repairs (i.e. like getting rid of the chipped paint in the bathroom) and a Continental Breakfast (with pre-wrapped items like croissants and muffins) could improve the value. My room and balcony were clean for the most part, but some aspects were a bit "run down." That would NOT deter me from staying again in the future.