I've been to the Edgewater Manor several times over the past few years. Excellent!
Aberdeen Tavern was a local go-to for me when I was living in the area. Fantastic menu, and not that pricey. The patio is really nice.
The French is another favourite (same owner as Aberdeen)
Visited Lo Presti's at Maxwell's before it closed. It will be missed.
Took my parents to the Purple Pear a while ago. Loved it.
Ancaster Mill is still fantastic.
I've never been to Quatrefoil but have wanted to try it.
Haven't been to Shakespeare's in about 15 years, but I find it hard to believe someone could spend $700 there for two unless there were multiple bottles of wine as part of the meal. It's not a cheap place, but their curbside menu has prices:
http://www.shakespeares.ca/curbside-dining
A bit further beyond, but Napoleon's in Burlington is an old-school steak house that was fantastic as of 7 or 8 years ago. And the wineries to the east have some really great restaurants: Peninsula Ridge and Redstone are two I've been to for dining. Oh, and Spencer's is another one not too far out of town. Inside or out on their "deck"
While I appreciate well prepared foods, price notwithstanding, most of these places have also featured FANTASTIC staff and that goes a long way for me.