Winter Garden is a very nice area. There is great shopping outdoor mall with shops,
Best Buy, Lowes, Super Target, Home Goods, and several restaurants.
The 429 has several new communities being built. Toll Brothers, Taylor Morrison, Ashton Woods, David Weekley, K Hovnanian, Lennar just to name a few. The added bonus of this area is you are a whole FIVE miles from Exit 8 pff the 429 which takes you straight into Disney.
Winter Garden does not border Pine Hills. You don't want Pine Hills (we call it crime hills)
Windermere will cost you more. Taxes will also be higher. If you were to live near downtown Windermere, it is not uncommon to have a huge house right next door to a little 1800 square ft cottage. Many buy houses, to tear them down and rebuild.
Dr. Phillips. Also known as D.P. The houses are older as most of the neighborhoods are close to 20 or more years old.
There is okay shopping, but the area around Sand Lake Rd gets congested from locals as well as tourists that are checking things out.
Clermont is about a 25 minute drive from Disney depending on how you go. The Florida turnpike to exit 272 is the best way to go. Get off the exit, turn left and you will be in Clermont in two minutes. There are several nice areas on either side of Hwy 27 in different price ranges. Clermont is in Lake county, just an eh on the Lake county schools imo.
About 20 minutes from WDW, right near the Orlando airport, is Lake Nona. This is also a very nice area. Lake Nona is really growing. There is more shopping centers going up and a lot of restaurant choices as well. Just hop on the 417 to exit 6 (or 3 if you prefer) and you are right in the thick of things at Disney.
If you have any other questions, I will be happy to answer them. I have lived in Florida 25 years+ and know the area well.