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Middlebury is the best commute but hard on that budget and also it should be known that Middlebury has almost no commercial development so amenities are few.
As others noted that would be a tight budget for those towns. Not impossible but tight. Have you considered Southington? It is about 20 miles from Watertown (30 to 45 minutes) and would provide you access to job markets in Hartford, New Haven and Waterbury. The town has good schools and will give you a lot more home for your money than the other towns. There is plenty of shopping in town and a lot of family activities as well. Jay
With a job in Watertown, and a budget under $300k, I'd be looking at Prospect, Southington or Watertown itself. The other towns are very pricey and you likely won't get the kind of home you want.
I would generally not recommend living to the east of Waterbury if someone has to commute to Watertown. I commute through Waterbury in the morning and as bad as it is coming from the west, it is worse coming from the east.
I'd look in Prospect/Beacon Falls and Watertown itself with that budget. Middlebury/Southbury are doable on under $300K but will require significant compromises on house size and condition.
You could consider Oxford too. There are houses in the sub $300 range and it would be a reasonable commute both to Watertown and to points south like New Haven and Shelton.
I took a look at what 's on the market in Middlebury under $315K. If you are not OK with a house that either faces or corners a busier road, the possibility of airport noise, or having a smaller house (1200-1500 sq ft, ranch or raised ranch), scratch it off the list.
You could consider Oxford too. There are houses in the sub $300 range and it would be a reasonable commute both to Watertown and to points south like New Haven and Shelton.
I checked on Zillow. seems like Oxford is even more expensive. with same amount of money houses in Oxford are much smaller in size...
I do agree Prospect makes the most sense followed by Watertown. $300ish can get you into some of the nicer neighborhoods in Watertown. I figured I would toss Oxford into the mix because of its location and not knowing where OP would be needing to travel.
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