[JayCT]

Originally Posted by CYP3A4

Thank you all so much! Thanks for the links to the homes for sale too! We will be visiting in May and will definitely check out those areas.

My husband's office will be near Fairfield (can't remember exactly where), but he works from home the majority of the time and will only be driving to the office maybe once a week.

Thanks so much for all your help! This was way more information than I was expecting!

I am assuming you mean the Town of Fairfield. Any town north of there could be good. It just depends on how far he is willing to be and what you expect for your money. I would suggest Newtown as a starting point. It is a nice town with many more rural parts yet still has some shopping there or nearby. If that is not rural enough, I suggest heading further north into Litchfield county. Towns like Roxbury, Washington, Bridgewater and Woodbury may be more to your liking then. Jay

[NewJeffCT]

agree that Roxbury, Washington & Bridgewater would be a good place to look. The regional school district is above average in the state and you can probably get a good amount of land. You can find at least 15 homes in this area that have over 5 acres.

I'd look at Bethany, too, but I just did a quick search for under 600K and there is nothing in Bethany that is 5 or more acres at this time. Several places that are 3-4+ acres, but you need to get into the 600s-700s to find 5 or more acres. Bethany would be a much shorter commute to Fairfield and has excellent schools.

[hvexpatinct]

Originally Posted by Stratford, Ct. Resident

Something like this?

That's a beautiful neighborhood. Really limited cell service... not always a bad thing though!

[Stylo]

Originally Posted by NewJeffCT

agree that Roxbury, Washington & Bridgewater would be a good place to look. The regional school district is above average in the state and you can probably get a good amount of land. You can find at least 15 homes in this area that have over 5 acres.

I'd look at Bethany, too, but I just did a quick search for under 600K and there is nothing in Bethany that is 5 or more acres at this time. Several places that are 3-4+ acres, but you need to get into the 600s-700s to find 5 or more acres. Bethany would be a much shorter commute to Fairfield and has excellent schools.

I don't think you'll find anything in Roxbury/Bridgewater/Washington at their budget either

[NewJeffCT]

Originally Posted by Stylo

I don't think you'll find anything in Roxbury/Bridgewater/Washington at their budget either

I just found over 15 properties in the 3 towns that had at least 5 acres of land that were under $600,000. While they're not going to find Craftsman homes, some of them seemed pretty nice. In Bethany, there were 0, though there was one that was at $610,000, I believe.

168 Spencer Hill Rd, Winsted, CT 06098 is For Sale - Zillow

155 E Flag Swamp Rd, Roxbury, CT 06783 - Zillow

139 Laurel Way, Winsted, CT 06098 is For Sale - Zillow

52 Hinkle Rd Washington # 6793, Washington, CT 06793 is For Sale - Zillow

The last home in Washington has a barn, two fenced in pastures and an in-ground pool on almost 7 acres. The first home has 11.6 acres.

[Stylo]

The 1st and 3rd are Winsted, not Washington. The Roxbury one is not a bad find. That Washingon house is certainly, er, rustic .

Generally that area is fairly pricey

Still think Durham area will be most bang for buck plus proximity.

[NewJeffCT]

My bad - I confused Winchester (of which Winsted is a part) & Bridgewater

However, Winchester schools are still pretty good (Region 7, which includes Barkhamstead, New Hartford and a few others) and is also commutable to Fairfield, since you just go straight down Route 8. No real traffic until you hit Shelton.

The problem with Durham is that it's going to take you 20-30 or more minutes to get onto 95 going through Madison and Guilford, and then you still have to go through New Haven traffic. I saw 2 homes in Durham that were built in the 1700s, I liked the home at 300 Old Stage Coach, but google maps has you spending 25 minutes just to get into north Madison, and then you're going to need another 20 minutes to get onto 95 trudging through Madison. You could also go north from Durham into Middletown, drive up Main Street and then take 9 north into Cromwell, then swing down 91 south from Cromwell into New Haven, but you're going to be spending an hour just to reach New Haven...

[Stylo]

The OP only needs to be in Fairfield once a week, so I don't see Durham as being too inconvenient.

Also, from Durham you just take 15 instead of 91/95. It wouldn't make sense to go through Madison/Guilford as that's backtracking. It's quite easy actually:

https://goo.gl/maps/n6vP5

[willow wind]

You don't even have to do any of those backtracking routes to get to New Haven from Durham. Example, the Stagecoach Rd. area is not even a mile from the North Branford town line.

So you do what most people who live in Durham and work in the New Haven area do. Take Rt 17 into North Branford and follow it to 1-91. You pick up 1-91 at the Rt 80 intersection. It's about 10-12 minutes to 1-91 if that from Stagecoach. Then 1-91- obviously to 1-95 to to Fairfield.

If you only had to do it once a week, it's not all that a bad commute, generally under an hour.

[CTartist&musician]

My husband has friends and relatives in the Durham/Middletown area. In fact his uncle was a principle at schools in both towns. They love it up there. I do to. I live in Trumbull (right near Fairfield) and it only takes about 1 hour and 15 minutes. Once a week would not be bad at all to make that trip.