[AmyMacfreid]

After 20 years in California we are considering a move. I grew up in Ridgefield and like the home-town feel, but fear it maybe too rural for me after 20 years in California. My husband fears that Greenwich is too affected... too many gates, if you know what I mean. We have 4 kids. We will have two at boarding school, one in elementary and one in middle school.

So I guess I have two questions:

Which is more friendly....

.... and is it possible to live in Ridgefield and not drive 15 miles to Target or get a high-end services/products?

[Stylo]

Ridgefield has changed in 20 years. It's a bit more affluent even than it was. That's not to say it's gotten worse or anything, still a great town.

It's hard to say. I guess overall Ridgefield is a bit more down-to-earth, but Greenwich is a bigger town and has all sorts of people - though mostly affluent. Some neighborhoods in Greenwich are much more tightly knit which encourages more interaction with neighbors.

Greenwich is MUCH more expensive.

The closest Target to Ridgefield is in Bethel, which is about a 15 minute drive. What do you mean "high-end services/products"?

Where are you going to work? You might want to consider Fairfield.

[kidyankee764]

There are areas of Greenwich that are very family friendly. Old Greenwich and Riverside to name two. The "gates" are mostly north of Route 1, where you'll find some of the largest estates in the world. I really love Old Greenwich, but it's pricey. That said, it's close to Stamford so there is a Target 6 minutes in one direction, while you have all of the high end Greenwich Ave shopping 6 minutes in the other direction. If you're working in New York, go with Greenwich, absolutely. Even if you work in Stamford, I would pay the extra for a home to have a shorter commute (Fairfield County traffic can be horrid).

[AmyMacfreid]

Thanks for the local insite. My husband works from home, and I am a baker. So we are pretty flexible.

Ridgefield is on the list because of my family history in town, the walkability and the relative down-to-earth sensibility there.

Greenwich is on the list because we've gotten used to things like nice restaurants, stationary stores, markets, wine, shops like JCrew around the corner. It also seems nice to have the train to NYC just 40 minutes, as opposed to Branchville that is longer with a change in S. Norwalk.

In either case, we REALLY want to live within walking distance to town and school. Do you know if this is even possible in Greenwich?

[Stylo]

Down-to-earth sensibility? That's a new one. Greenwich is one of the most affluent towns in the country.

If you don't have to commute and don't mind a little longer trip to NYC (70 minutes direct), check out Fairfield. It's walkable in some parts (moreso than Ridgefield), down-to-earth for the most part, people are super friendly, schools are excellent, and it's MUCH cheaper than Greenwich. The beaches are also really nice, and there's lots of activity and things to do. There's also more shopping options than Ridgefield nearby, including a few Targets in nearby towns.

You may also want to check out Westport, though it is as expensive as Greenwich and I would not call it down-to-earth.

I also like the Wilton suggestion and it's a bit more convenient to amenities than Ridgefield.

Also, without your budget it's really hard to tell, but maybe you would like Bethel or Milford. Both have beautiful town centers that are walkable, convenient shopping (Target in-town along with many others within a short drive), lower real estate costs, good schools, train to NYC (though Milford's is more frequent/faster), etc. They are much more middle class than the other towns suggested, so they may have that down-to-earth sensibility you're looking for.

It's absolutely possible to be in walking distance of Greenwich center, although houses around there tend to be very expensive and are in limited supply. Also, you may not be lucky enough to be walking distance to school and town, that's a tall order in any CT town when the schools are all over the place.

[jax12479]

If you can comfortably afford it, I would say Greenwich hands down, but I'm biased

Ridgefield is a lovely town, but as you noted - it's quite rural. Greenwich is much more like a small city, but there are a lot of family neighborhoods that have more of a "small-town" feel. Most people LOVE Old Greenwich and Riverside because they are very family-oriented neighborhoods and are in walking distance to great schools and some local shops. They are also very close to the beach, which is a big draw.

Another alternative is downtown Greenwich, but that is a much busier part of town (lots of traffic and not very residential). You can look in the Bruce Park area -- that is somewhat walkable to Greenwich Ave and is more of a neighborhood than living right off Greenwich Ave itself.

[kidyankee764]

Originally Posted by AmyMacfreid

Greenwich is on the list because we've gotten used to things like nice restaurants, stationary stores, markets, wine, shops like JCrew around the corner. It also seems nice to have the train to NYC just 40 minutes, as opposed to Branchville that is longer with a change in S. Norwalk.

Hmm - have you looked at Westport?

[MikefromCT]

I definitely agree that Westport is worth a look. How about Fairfield, just to the east. It's really expensive but one's budget will definitely go further there. Also, they do have a nice Main Street and it shouldn't be too far from major shopping, I don't think. I know the OP specifically mentioned Target, which I'm not sure Fairfield has, but there's a Trader Joe's and other chain stores on Boston Post Road. Just a thought.

[JayCT]

I am not sure what you are looking for or what your price range is but I will say that the Southport section of Fairfield is the most stunningly beautiful area I know of. It is a charming waterfront village with a lot of beautiful old historic homes overlooking a picturesque harbor. It is pricey but if you can afford Greenwich you can likely afford Southport. Plus you will be near some great shopping and restaurants in Westport and Fairfield and New York is a little over an hour away. Just a thought. Jay

[Stylo]

Originally Posted by MikefromCT

I definitely agree that Westport is worth a look. How about Fairfield, just to the east. It's really expensive but one's budget will definitely go further there. Also, they do have a nice Main Street and it shouldn't be too far from major shopping, I don't think. I know the OP specifically mentioned Target, which I'm not sure Fairfield has, but there's a Trader Joe's and other chain stores on Boston Post Road. Just a thought.

There's 2 Target's within a quick drive from Fairfield

It's expensive, but wayyy cheaper than Greenwich and also less than Westport. It's on par with Ridgefield, but has better NYC train access in town.