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I've been house hunting for the last several months and have been looking at the same areas as you. Out of the 3 areas you talk about, I think Oviedo has the least amount of charm. It's pretty much your standard suburb, fairly convenient to shopping/amenities. I think a lot of out of state folks with families pick Oviedo because of the lower price of homes the better public schools.
Buying into Heathrow and Tuskawilla is more buying into a lifestyle. We've looked into homes in Heathrow and the way my husband would describe it, is its like living in a different world from Centeral Florida. Everything is perfectly manicured. People seem to all know eachother. It's a select group of people that want sort of the same living environment. Once you get in the gates of Heathrow, there isn't the road rage, traffic, rude people that are often what people complain about in the Orlando area. It's not for everyone, but if that's what you're looking for, it would be a good match. It's also very convenient to all the shopping/dining/parks of Lake Mary, which in itself is very nice and upscale. Has some established companies like AAA Headquarters, Mitsubishi, Fox News. Close to I4 & 417.
I haven't looked as closely into Tuskawilla Country Club, but that area seems very nice as well. The homes seem to be a bit older and it doesn't seem like there are as many homes to chose from. The lots seem to be bigger than what's offered in Heathrow. To me, Winter Springs seems more of a suburb of Orlando, rather than it's own town, although they did build a very nice Town Center recently. I think the Tuskawilla folks tend to mix with Oviedo more, since the Oviedo Market Place is so close. It's convenient to UCF, Siemans. Just looking into the Winter Springs parks dept for my kids, the sports teams seems to sometimes combine with Oviedo teams or play at Oviedo facilities.
Probably a big thing to consider is where you will be working and figuring out the commute times. If you're working in Orlando, I think Heathrow will be a bit of a trek. I've heard I4 can be a nightmare. I don't think you can go wrong with any of them. It's mainly finding a home you like. You can probably get more for your money in Oviedo, which is good and bad. To me, it seems Oviedo has had slightly more problems with the housing bust. Heathrow and Tuskawilla are more established. Good luck!
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