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If access to NY by car is a priority, you want to be closer to 84 than to 95, so inland vs on the coast. In addition to West Hartford, Bethel is a good choice for conveniences, municipal services (natural gas/public water/sewer)/access to NY, although the taxes are high.
Woodbury is nearly entirely oil/well/septic. I believe Woodbridge is as well. Woodbury has a large empty nester population and definitely has more going on than Woodbridge, but Woodbridge is closer to New Haven which opens up another world of social opportunities.
When you go to do major shopping as a resident of Woodbury do you go to the Danbury Mall or another mall? Is there major shopping near you there beside the Danbury Mall.
These towns might be good too. I think all of these town have houses on large lots too and they are not that far from the Danbury Mall. The op would have good access to Storrs and NYC to via car.
"Woodbridge is closer to New Haven which opens up another world of social opportunities"
I was thinking that someone from NYC might be bored in some of the more quiet towns like listed above. I like Trumbull because I am not far from the 1-95/Metro North/Route 1 (Post Road) corridor that has lots of shopping, restaurants etc. in all the towns it runs through in Fairfield County.
When you go to do major shopping as a resident of Woodbury do you go to the Danbury Mall or another mall? Is there major shopping near you there beside the Danbury Mall.
People who live in Woodbury or neighboring Middlebury/Southbury normally do basic shopping in town or in Southbury. The area has all of the basics - multiple grocery stores, Starbucks, fast casual places like Chipotle, TJ Maxx, the Gap, Old Navy, Talbots.. along with lots of indie restaurants, hardware stores, gift shops, farm stands.
For big box shopping many go to Brookfield or Bethel, although some people go to Costco or Target in Waterbury, or up to Torrington for Target/Walmart.
For more varied shopping, Danbury, Milford, and West Hartford are all roughly the same distance. If I have the choice I pick West Hartford for more major shopping - just easier to travel from store to store there.
For healthcare most people go to Southbury for outpatient care and Danbury/Waterbury/Yale for hospital care.
Given your situation, you probably wouldn't want to move to Cheshire. Our superintendent likes to say "no one moves to Cheshire for the nightlife." Families move here for the school system. We live in the northern area of the town near the prison and it really is a non-issue for everyone. Also the taxes will be going up soon since the town is getting ready to build new elementary schools.
Don’t be afraid of going farther east, the Red Sox and pats fans don’t bite. Glastonbury, only a tiny bit further east, is very nice, somewhat walkable, loaded with amenities and convenient to Hartford jobs.
That's a good point about Glastonbury. I feel like people sleep on the fact that there is a good chunk in and surrounding Glastonbury Center that is very walkable. Grocery store, many restaurants, liquor store, coffee shops, hardware store, pharmacy, medical offices, bank, library, etc. are all very conveniently located to each other and housing.
Because you plan on looking for a job, I think it would be wise to pick a town in between two major cities so you'll have better options for finding work. I think you should seriously consider Southington. It's more convenient to highways than Cheshire, so you could commute to New Haven or Hartford. Berlin is also a possibility, though I find Southington more appealing because it has more walkable areas.
You can also pick Simsbury or South Windsor, which are between Hartford and Springfield. Simsbury is more isolated because it's far from the highway. South Windsor has easier access to highways and would put you closer to UConn.
I don't know much about Fairfield County towns so I'll let others comment on that.
People who live in Woodbury or neighboring Middlebury/Southbury normally do basic shopping in town or in Southbury. The area has all of the basics - multiple grocery stores, Starbucks, fast casual places like Chipotle, TJ Maxx, the Gap, Old Navy, Talbots.. along with lots of indie restaurants, hardware stores, gift shops, farm stands.
For big box shopping many go to Brookfield or Bethel, although some people go to Costco or Target in Waterbury, or up to Torrington for Target/Walmart.
For more varied shopping, Danbury, Milford, and West Hartford are all roughly the same distance. If I have the choice I pick West Hartford for more major shopping - just easier to travel from store to store there.
For healthcare most people go to Southbury for outpatient care and Danbury/Waterbury/Yale for hospital care.
All that shopping up there requires some driving to get to a those places.
Down on the Metro North/I-95 corridor we have so many people shopping is more concentrated and we don't have to drive as far.
In Trumbull within a 5 minute drive I have the mall with JC Penny's, Macy's, Target etc. I also have the Home Depot and two gyms the grocery store banks, Town Hall area. Within a 10 minute drive I also have Kohls, another Target lol, Best Buy, Home Goods and more stores in another little Hawley Mall. In about 15 minutes I can be at the Post Road from Fairfield and then another mall in Milford. Milford has tons of shopping.
I have never been to Staten Island so it's hard for me to think of comparisons but I bet it is more like my area of more concentrated people and shopping than your area in Litchfield County or northern Fairfield County.
Have you considered Wilton? Buying a home can be expensive, usually in the 750-900K range. But if you could find one with less land attached to it than the prices easily drop down to the 400-600 Range. And pre-COVID, there were even some homes selling in the 300s.
With regards to activities, there isn't a whole lot of nightlife, primarily due to the fact that many businesses close by 9 PM. However there is still things to do during the day. Although our town center isn't that large (only about 5 streets) there's many activities there such as a movie theater, a library, a park, many restaurants, stores, and 2 banks. Then there is also a large commercial area along Danbury Road (Route 7) that comes in from Norwalk and continues up to Cannondale.
In terms of commuting, you can easily commute to Norwalk, Stamford, or Danbury. And there's also a large ASML plant in South Wilton that employs about 1200 people.
If you're wondering about character of the town, it's something that can only be described as "sparse suburban". It's not really that rural anymore. I know it looks rural compared to the coastal/panhandle towns, but it's actually very suburban. Although there are still established rural neighborhoods in North Wilton and certain areas close to the Weston border. There is also some very large wooded areas in the western side of town. The densest part of town is South Wilton, closer to the Westport Border.
Wilton is a very nice place to live if you can afford all the extra land that comes with homes.
Wow! That's a bunch to sort through and I appreciate all of it.
I had looked into Bethel as Stylo suggests but thought it might not be great to be near Danbury. (Not sure why I have that bias; I could be way off base).
We are going to try to hit some of these towns on our way home from seeing my daughter off to school.
Thank you all very much.
Nothing wrong with living near Danbury, just might be a little dull if you expect a city with things to do.
All that shopping up there requires some driving to get to a those places.
Down on the Metro North/I-95 corridor we have so many people shopping is more concentrated and we don't have to drive as far.
In Trumbull within a 5 minute drive I have the mall with JC Penny's, Macy's, Target etc. I also have the Home Depot and two gyms the grocery store banks, Town Hall area. Within a 10 minute drive I also have Kohls, another Target lol, Best Buy, Home Goods and more stores in another little Hawley Mall. In about 15 minutes I can be at the Post Road from Fairfield and then another mall in Milford. Milford has tons of shopping.
I have never been to Staten Island so it's hard for me to think of comparisons but I bet it is more like my area of more concentrated people and shopping than your area in Litchfield County or northern Fairfield County.
It’s not like we are constantly in the car going to and from Danbury. We have everything we need locally, just not in big box format. Up here the typical resident has three great coffee shops, two or three bakeries, four banks, several package stores, two pharmacies, three hardware stores, three excellent local grocery stores, probabky 20 restaurants, and a post office/library within a 5-10 minute drive. If I need hardware I go to Ace, if I need plants I go to the garden center, and if I need clothes I go to Marshall’s or TJ Maxx. I don’t do malls or HD type shopping often enough to value proximity. I will say that with very small children I did miss having better access to big box stores although that’s not been an issue with school aged kids.
It’s all moot if the OP wants access to municipal utilities, but southern Litchfield/northern New Haven counties arent super rural and are hardly isolated in the way that more rural Litchfield County towns like Norfolk, Sharon, Kent, etc are.
To me this seems to be a balance of how far you want to be from the city verses the house you get for your money. Generally the closer to New York City, the pricier the home. Coming from State Island, some towns may seem positively rural to you which is why I’d be careful in what I’d recommend to you.
Also note that it also depends what you expect for your budget. In Fairfield County your budget might get you a condo or a modest home. In Hartford County you’d get a nice 2,000 to 3,000 square foot home.
Since schools are not important, I’d start in Stamford and Norwalk. Both are closer to New York to make trips there easy. Though considered cities by Connecticut standards, they would be considered suburban like you find on Staten Island standards. What’s nice about is that both offer a wide range of neighborhoods to choose from large private lots to higher density apartment and condos. It all depends what you want.
The next step out from the city would be Fairfield. It’s a great town with tons of shopping and restaurants but you pay a premium because of the good schools. Again this is personal choice. Another option you may like would be the Black Rock section of Bridgeport. It’s a attractive waterfront urban village that some people love. You get more for your budget there but taxes are on the high side.
The next step would be Trumbull. As CTartist noted, it’s a beautiful suburban town with a lot of great stores and restaurants and a nice regional shopping mall. I do think you might find Monroes to be too quiet. Though very nice, coming from SI it will feel very rural.
Then you get to Milford. Because it’s further from the city, your budget goes a lot further. Milford has some of the state’s best shopping, dining and entertainment options in the state. It has a wide range of housing options from modest apartments to lavish waterfront homes. You are in between New Haven and Bridgeport so you are close to all that those cities have to offer. It’s a very nice balance you might like.
In greater New Haven, outside of Milford you might want to look at Wallingford. It’s a nice town with a wide range of housing options. It has low taxes and low electricity rates because it electric utility is operated by the town.
The next town I’d consider for you is Middletown. It has a great downtown with lots of restaurants and shopping including a branch of one of the best bookstores in the state, RJ Julia Bookstore. It is also the home of Wesleyan University so you have a lot of great activities a college town offers.
I do not think that you will like Cheshire. It’s pricey because of the schools and lacks a denser town center. Woodbury would be very rural so I would not suggest it.
In greater Hartford, West Hartford is hard to beat but as you note taxes are higher. For lower taxes yet still close to the amenities of West Hartford, you might consider Farmington. Taxes are less there yet it’s still a beautiful desirable community.
Glastonbury is a great town but you are paying a premium on home prices and taxes because of its schools. Instead I would recommend Manchester. I have good childless friends that live there and they love it. Their neighbors are former New Yorkers who moved to be closer to their kids in Glastonbury and West Hartford. It has great restaurants and shopping with another of the state’s largest regional shopping districts in the state, if not New England. There’s a wide range of housing choices and your budget will go a LOT further than other towns. Again this is your choice. Good luck with the decision. Jay
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