[olive03]

We're potentially interested in relocating from Chicago to CT. We would be coming from a very affluent area here with the best of the best schools in IL, however, the cost of living is knowingly higher out there. We have two school aged children and education + safety is the #1 priority. In looking at the prices in Greenwich/Darien, I don't think we're going to find what we want given our budget, nor would we probably fit in.

My question is, are there any other towns/cities in CT that have amazing schools outside of these areas? We would be working from home so commute is a non issue. My husband would like a smaller town/rural feeling, where I still need to be within a reasonable driving distance to somewhat of a metro area. He will fly on a frequent basis, both domestically and internationally, so a decent sized airport that isn't lightyears aways will also be needed.

Any guidance is appreciated.

Thanks!

[BlackRocker]

Maybe Weston

[JayCT]

It would help to know your budget, what you expect for it, what type of community you like, where you will be commuting to and how long of a commute you will tolerate. Generally the further east and north you go away from New York the cheaper homes get. I understand that schools are important but understand that schools here are among the very best in the country so your kids can still get an excellent education even in lower priced towns.

I assume that since Greenwich and Darien are too pricey, New Canaan would be too. Westport might be a good option next if you want to be on Metro Norths New Haven line but it too gets pricey. I would also suggest looking at Wilton and Weston which are inland and away from the train line.

If these too are too pricey, then consider Fairfield and Ridgefield. Fairfield is a larger more diverse town on Metro North but offers excellent schools while Ridgefield is inland and has one of the best school systems in the state. If you are commuting to Manhattan though, it would be a long commute. Again giving us more information would help us help you. Jay

[olive03]

Originally Posted by JayCT

It would help to know your budget, what you expect for it, what type of community you like, where you will be commuting to and how long of a commute you will tolerate. Generally the further east and north you go away from New York the cheaper homes get. I understand that schools are important but understand that schools here are among the very best in the country so your kids can still get an excellent education even in lower priced towns.

I assume that since Greenwich and Darien are too pricey, New Canaan would be too. Westport might be a good option next if you want to be on Metro Norths New Haven line but it too gets pricey. I would also suggest looking at Wilton and Weston which are inland and away from the train line.

If these too are too pricey, then consider Fairfield and Ridgefield. Fairfield is a larger more diverse town on Metro North but offers excellent schools while Ridgefield is inland and has one of the best school systems in the state. If you are commuting to Manhattan though, it would be a long commute. Again giving us more information would help us help you. Jay

Sorry, should have provided more information! Both my husband and I are will be working from home so can literally be any where there’s WIFI to get our jobs done. Our house budget is 800k - 1M and annual household income is 230k. That sets us up pretty well here but not sure how far it would take us there.

We’d like a single family house with a minimum of 2500 sf on a decent sized lot. I love historic houses and my husband daydreams about a small picturesque New England town where pace of life is slower than here. We also need to be in a location that is open to transplants as neither one of us are from the NE.

[BlackRocker]

I assumed you needed to be closer to NYC. I’d go for Guilford if this is not true.

[hvexpatinct]

I think Ridgefield would tick most of your boxes.

Be prepared to drive a bit to one of the major NYC airports for international travel, but it honestly isn't that bad - there also is a smaller commuter airport in White Plains, about 30 minutes away, with regular service to the major hubs as well as to FL.

[JayCT]

Originally Posted by olive03

Sorry, should have provided more information! Both my husband and I are will be working from home so can literally be any where there’s WIFI to get our jobs done. Our house budget is 800k - 1M and annual household income is 230k. That sets us up pretty well here but not sure how far it would take us there.

We’d like a single family house with a minimum of 2500 sf on a decent sized lot. I love historic houses and my husband daydreams about a small picturesque New England town where pace of life is slower than here. We also need to be in a location that is open to transplants as neither one of us are from the NE.

Since location it not important then I would go with Ridgefield or Fairfield. Fairfield has beaches on Long Island Sound and trains into Manhattan. It has a great downtown with tons of restaurants and shops. It is also a more diverse town with a wide range of housing options from modest apartments to mega estates. For charm, you can’t beat Southport and Greenfield Hill and Old Post Road and the Town Green.

Ridgefield is a smaller town and a bit quieter. The schools there are often considered the best in the state. Your housing budget will go far there.

Does it have to be in Fairfield County? As hvexpatinct suggests you might want to consider the beautiful shoreline towns east of New Haven. Guilford and Madison are beautiful towns with very good schools. They have a bit of a beach town feel but still offer a lot for families. Guilford has a very charming town green while Madison has the beautiful Surf Club town beach and park.

If being close to an airport is important, I would suggest considering living in the Hartford area. The Farmington River Valley, just west of Hartford is beautiful with a sort of Shang-ra-la feel to it because it is separated from metro Hartford by a line of small mountains. Farmington, Avon and Simsbury have excellent schools and just about everything you need within the valley itself. Plus it is very close to Bradley International Airport which is very convenient and easy to use. Might be a good option. Jay

[nico7]

I like Jay's recommendations and would add Orange, Woodbridge, and Bethany -- not that I think they are better choices, but they offer something different in being further away from NYC than Fairfield and Ridgefield, but also further from major airports. If you are looking for a slower pace, then you might want to look outside Fairfield County. Guilford and Madison would be about a 1 hour and 15 minutes drive to Bradley International Airport (BDL), but they are otherwise what you describe.

[olive03]

Thank you for the additional input! I will be looking into these recommendations!

Can anyone elaborate on the schools a bit more? We currently feed into a high school that is in the top 1% in the country and where the opportunities are endless, so I fully admit that our bar is set extremely high coming out of the gate. Also, are any of these districts known for their gifted programs?

Finally, I read that crime in Hartford is fairly high? What about the towns near it?

Thanks again!

[CTartist]

Originally Posted by olive03

We're potentially interested in relocating from Chicago to CT. We would be coming from a very affluent area here with the best of the best schools in IL, however, the cost of living is knowingly higher out there. We have two school aged children and education + safety is the #1 priority. In looking at the prices in Greenwich/Darien, I don't think we're going to find what we want given our budget, nor would we probably fit in.

My question is, are there any other towns/cities in CT that have amazing schools outside of these areas? We would be working from home so commute is a non issue. My husband would like a smaller town/rural feeling, where I still need to be within a reasonable driving distance to somewhat of a metro area. He will fly on a frequent basis, both domestically and internationally, so a decent sized airport that isn't lightyears aways will also be needed.

Any guidance is appreciated.

Thanks!

I am originally from Stamford so I have many relatives and friends in the area of lower Fairfield County. I have a friend whose husband needs to fly internationally for business. They bought a house in Newtown which is a town that would fit your criteria and it fit theirs too. My friend loved it there. The only problem was that it was a drain on my friends husband to get to the Kennedy Airport for frequent business travel so in the end they ended up in New Canaan.

I want to know from you why you don't think you would fit into Greenwich Darien or New Canaan. Here is the reason I ask. My friend doesn't feel like she fits into New Canaan and would rather be back in Newtown.

If your husband needs to fly frequently I would recommend being close to an airport that your husband can easily get to because the traffic in Fairfield County and the NYC is really bad. That is the problem.

How often does your husband fly out of the airports? He might have a better tolerance for the travel to the airport than my friends husband.