[JayCT]

Originally Posted by Raider111

Sounds like Ridgefield, Wilton, and Westport would all fit nicely, albeit Wilton has a much smaller downtown, but the others can be a short drive. Westport will be much more congested along the Post Rd, but the downtown/riverfront can't be beat on a warm summer evening with the Levitt mentioned by beerlover. There is a walkway behind some commercial buildings along Riverside ave over the bridge where you frequently see artists painting the riverscape on canvas.
Redding, Weston, and Easton are very rural with little to no commerce.
Outside of the Greenfield Hill section (and too far from NYC), Fairfield is basically a city in comparison, much more dense - urban/suburban.

Fairfield is not urban. It is suburban. It has a very nice downtown area, typical suburban strip shopping centers along the rest of Route 1 and Black Rock Turnpike and a lot of moderately dense neighborhoods. Homes sit on lots from about 5,000 square feet to 2 acres or more. There are no high rise buildings either so it is not close to what most people think is a city. Remember the OP is coming from Brooklyn so Fairfield Could feel positively rural. My sister had a friend in college from Brooklyn whose Doctor father thought the neighborhood we lived in was the country because we had trees in our yard. We lived on Tunxis Hill which is about the densest part of Fairfield.

Since the OP wants to be near a train into New York City and wants a more down to earth town, Fairfield may be a good choice for their second home. Ridgefield is beautiful but does not have a train that goes directly into New York. Another option for them may be Milford. Similar in size to Fairfield it has a lot of nice homes on or near the water. Might be worth a look. Jay

[lazylghtng]

Originally Posted by JayCT

Fairfield is not urban. It is suburban. It has a very nice downtown area, typical suburban strip shopping centers along the rest of Route 1 and Black Rock Turnpike and a lot of moderately dense neighborhoods. Homes sit on lots from about 5,000 square feet to 2 acres or more. There are no high rise buildings either so it is not close to what most people think is a city. Remember the OP is coming from Brooklyn so Fairfield Could feel positively rural. My sister had a friend in college from Brooklyn whose Doctor father thought the neighborhood we lived in was the country because we had trees in our yard. We lived on Tunxis Hill which is about the densest part of Fairfield.

Since the OP wants to be near a train into New York City and wants a more down to earth town, Fairfield may be a good choice for their second home. Ridgefield is beautiful but does not have a train that goes directly into New York. Another option for them may be Milford. Similar in size to Fairfield it has a lot of nice homes on or near the water. Might be worth a look. Jay

Ha ha! That's funny re: Doctor story. But I catch your drift as well the other poster's point of view. We are not full-on concrete jungle types so the Fairfield description was helpful distinction. But, again, I want to avoid a village that is full of chains or empty storefronts. Not sure if that applies to Fairfield (that is where Southport is, right?)

I am ok without a train station in Ridgefield since I can just get a lift to Goldens Bridge.

Need to do more recon on Milford and Woodbury. If it is indeed the ideal fit then I'll suck it up and buy a used car if absolutely necessary.

[hvexpatinct]

Woodbury has a couple of chain banks. Everything else in town is locally owned, from the coffee shops to the grocers (there are two and they are excellent) to the toy store.

It is an interesting town because of its linear town center. Everything is technically walkable from a center point, but very spread out.

Aesthetically - things are well taken care of, if a bit rustic in some ways (due to P&Z regulations - think handmade wooden signs for businesses). There are some unoccupied storefronts scattered through town, but they are typically very well maintained, freshly painted etc. It's one of the oldest towns in the state and preservation is a focus.

Milford is a very different place and not one I would think of for a country home (vs Guilford or Madison further east) but it is definitely vibrant and walkable. The town center aesthetics are fairly solid in my opinion too - the housing has a lot of aesthetic parallels to housing in Rhinebeck, but Milford has overall a more coastal, down to earth vibe.

[basehead617]

Originally Posted by lazylghtng

New Milford (new to me) looks like it has a lot going for itself in terms of vibrancy. On the other hand, the size of the town strikes me as (perhaps) being very suspect to inconsistency re: aesthetics. Recognizing that no town or village is without its fair share of desirable/less desirable streets, I am really hoping to find some consistency/uniformity as far as overall architectural appeal is concerned. Or at least in terms of presentation/upkeep if that makes any sense.

If you want upscale country without riffraff/bad aesthetics, but near New Milford's vibes, there's Bridgewater or Washington right next to it. Towns in CT are so small that focusing on living in one particular town for the town's amenities itself almost doesn't make sense. New Milford is so geographically large that you could be nearer the downtown of New Milford while living in Bridgewater/Washington than living in many places in New Milford itself. They are IMO very high on the list of best country home destinations in the world.

[lazylghtng]

You guys are amazing. Can't thank you enough for helping me expand and refocus my search.

So, it looks like I should consider:

- Ridgefield
- Southport?
- Milford
- New Milford
- Woodbury

[JayCT]

Originally Posted by lazylghtng

You guys are amazing. Can't thank you enough for helping me expand and refocus my search.

So, it looks like I should consider:

- Ridgefield
- Southport?
- Milford
- New Milford
- Woodbury

Southport is a section of Fairfield. It has one of the most charming villages in the country. Beautiful historic homes on charming streets and a beautiful little harbor with a yacht club full of beautiful boats. If I could afford it I would definitely consider living there. The only thing is I am not sure how down to earth it is.

Again you should note that New Milford, Woodbury and even Ridgefield does not give you a 10 to 15 minute ride to a train into New York or easy access into the city. Jay

[kidyankee764]

Originally Posted by lazylghtng

You guys are amazing. Can't thank you enough for helping me expand and refocus my search.

So, it looks like I should consider:

- Ridgefield
- Southport?
- Milford
- New Milford
- Woodbury

I would scratch Milford. While downtown has a few non-chains, much of the town is strip malls and filled with chains. It is, IMO, your typical middle class suburb and doesn't have nearly the charm found in other more rural, "getaway" towns. It's a nice place to live, but it wouldn't be my first choice for a weekend getaway.

Southport is beautiful but very expensive. Woodbury is also beautiful but is not near a train. You should definitely visit all these communities and see which feels like home to you.

[kidyankee764]

Originally Posted by JayCT

Monroe is not 10 to 15 minutes from a train station. Jay

Actually most of Monroe is 15 minutes to Bridgeport/Fairfield/Stratford stations. You can get to Bridgeport in 15 minutes easily from the center of Monroe. That being said, I don't view Monroe as a weekend destination. It's more of an upper middle class bedroom community.

[Raider111]

Originally Posted by lazylghtng

Ha ha! That's funny re: Doctor story. But I catch your drift as well the other poster's point of view. We are not full-on concrete jungle types so the Fairfield description was helpful distinction. But, again, I want to avoid a village that is full of chains or empty storefronts. Not sure if that applies to Fairfield (that is where Southport is, right?)

I am ok without a train station in Ridgefield since I can just get a lift to Goldens Bridge.

Need to do more recon on Milford and Woodbury. If it is indeed the ideal fit then I'll suck it up and buy a used car if absolutely necessary.

urban vs suburban whatever, Jayct likes to speak of and yearns for the Fairfield of yesteryear when it was a quiet suburb of Bridgeports manufacturing heyday. That town is long gone and been replaced by transient families relocating in and out to commute to jobs further south (NY-Stamford), not very quaint and definitely has it's fair share of building/apartment/condo cluster.
End of the day, the coast is more dense, hectic wherever (what I like and prefer so not being biased), Sounds like a Ridgefield type would be more to your liking.
If your considering Southport, then also check out the Rowayton section of Norwalk, similar vibe and waterfront affluence but closer to NY.
Milford doesn't fit here, the chain store/restaurant capital of CT.

[beer belly]

If I were a city dweller looking for a summer home, it would be New Fairfield or Brookfield waterfront on Candlewood Lake, but thats just my taste, nothing like sitting on your back porch watching the boats on the lake, or taking yours out for cruise on the water