Grew up in Milford. It’s a wonderful city. Woodmont > Devon.

I recently got to visit Milford and I really liked it. There was a farmers market or something happening at the green and I remember seeing a couple around our age pushing a stroller and walking their dog and just thinking this is exactly what I'm looking for. I just got "that feeling" when I visited I guess I should say. Are there any "bad parts" of Milford or areas you'd avoid? Thanks!

Norwalk!

So Norwalk is interesting to me, I just got to visit there a couple weeks ago. Definitely more of a city feel, sort of reminded me of where I used to live in Baltimore but I did enjoy it. Only issue I've seen based on my research is the schools aren't rated very high, I've seen some areas the crime is pretty high(might be a reason I'm unaware of), but I would think the houses would be less in that area but they aren't. On the surface seems like much less bang for your buck is all.

Like any mid-sized city Norwalk is not without its crime, however it's generally very very localized and not a pervasive problem whatsoever. I've lived here almost my entire life and have always felt very safe.

My wife and I are both products of Norwalk public schools and we turned out just fine- both successful professionals with advanced degrees. The schools may not be as great as surrounding affluent towns like Darien/New Canaan/Wilton/Westport, but compared to other schools in the state they are about average, and on the national scale they are above-average.

Depending on where you are in the city, Norwalk can feel very urban/city-like, or very woodsy/suburban and even rural. It's a large city geographically so there is plenty to do, and each section of town has its own distinct feel to it.

Feel free to PM me with any specific questions, always happy to fill people in on Norwalk and how great it is. Definitely a great place to raise a family.

I appreciate this and will definitely be looking into Norwalk more. Are there any areas of Norwalk you would suggest?

Stratford is lovely.

No, there are no bad parts.

Stratford is next door and is FFC, but the taxes are much higher than in Milford and it’s arguably a more blue collar town. Lord$hip is on the water and beautiful, and there are great neighborhoods in the north end (check out Beaver Dam area). Everything in between is kind of meh, and parts of the south end (success village) suck. That said, I would not hesitate if you can afford one of its “nice” neighborhoods.

Then there’s Shelton and Trumbull if you want a more rural lifestyle.

Fairfield is beautiful if you can afford it.

So I've been to Stratford a few times, I actually went to look at a house that was on main street and no offense to anyone but let's just say main street wasn't what I was expecting. Someone told me that upper/northern Stratford is where you want to be.

Wilton has A plus level schools but is very expensive.

Norwalk gets a bit of a bad rap because it's constantly compared to school districts like Westport & New Canaan, which have some of the best schools in the country. However, Norwalk is still above average nationally. If you want a city feel, it's a great place. If you can swing it, Westport, Wilton, Weston are also fantastic and have great communities and an amazing place for young kids to grow up. So many young parents, too.

Inventory is still super low and the Norwalk real estate market is still hyper-competitive. I'd be more inclined to advise you against certain areas, but generally speaking if you're looking at single-family homes then most of the neighborhoods where those are located are generally safe. The socioeconomic dynamic in Norwalk is really geographically-dependent, sometimes even down to a block or two. SoNo and Wall Street are perfectly safe areas to visit for dining/entertainment, but I'd avoid any homes within those vacinities.

Cranbury, Silvermine, and West Norwalk are generally the safest but most expensive. Rowayton is technically a part of Norwalk but might as well be its own town, it's basically just an extension of the wealth/exclusivity you see just across Five Mile River in Darien. East Norwalk is really nice, but overpriced due to proximity to the water and the houses are all a bit smooshed together for my own liking. The neighborhoods off of Westport Ave., East Ave., West Rocks Road, and Newtown Ave/Chestnut Hill Rd. are all really great options for situation, but good luck finding anything right now haha.

If that is what you liked, I would definitely recommend one of the more walkable parts of Milford, like close to downtown/green, close to walnut beach, close to anchor beach (less happens there but it is pretty) or if you can afford it, similar vibes in parts of Westport, Darien, Greenwich (but double to triple the housing costs)

Yeah unfortunately our budget probably won't allow for a home in Greenwich or Westport haha. A lot of people suggested Shelton which I did visit but didn't get that warm and fuzzy feeling. We do like Newtown a lot also. I wouldn't mind Fairfield but my god the asking price for some of the homes in Fairfield is just laughable.

I second this.

Fairfield has a lot for families and has good schools.

We really like Fairfield and that is where I've spent the most time because that's where our friends live. I realize inventory is still low but some of the asking prices for houses in Fairfield are just laughable.

Westport is nice, but more expensive. Overall in Connecticut since 1980, the population has grown about 25% but housing has not kept up, hence our housing shortage. I don’t expect it to go away for a while.

Yeah and unfortunately some people are taking advantage of that which is expected. Just yesterday I saw a house in Fairfield (06825) that needed a good amount of updates and they were asking like 950K. I wouldn't pay 500K for that house. Just gotta keep our fingers crossed. Seems like Newtown has a lot of nice homes in our price range as well.

Rowayton

Milford is my favorite one. One high school (Foran) is considered better than the other (Johnathan Law), but both are good. There's a train station to get you right to NYC, or to Bridgeport here in CT for events. I visited a lot growing up and I still do. Very nice city.

Shelton is close by. My current hometown. I love it here. You get the privilege of saying you live in Fairfield County for incredibly low taxes. I think the schools are seen as slightly less good than Milford, but they are still very good. There's a bunch of farms here. There's a also a train station to get you between Waterbury and Bridgeport. You can switch in Bridgeport for a train to NYC.

I grew up a town over in Trumbull. They have an amazing school system, a great music department, and great sports teams. The taxes are very high though, but if you want an expensive town with a great school system this is the one to choose. The really expensive ones such as Westport, Fairfield, Wilton, Darien, Greenwich, Easton, and so on are rip offs in my opinion. If it came down to it your kids would be able to apply to the agriscience program at Trumbull High someday. Milford high schools are good enough though. I know people with kids at Johnathan Law (the one seen as less good). No problems.

Overall I vote for Milford. Nice people, the mall, Dave & Busters at the mall, the movies, a train station with a train directly to NYC, but also stopping in Bridgeport for events, and a great downtown area.

This was super insightful, thank you very much

Agreed. I grew up in Trumbull, but visited a lot for family. I loved Milford. I know the Trumbull school system is seen as better, but overall I think Milford gives you more bang for your buck. A great downtown, the mall, the movies, a good school system for lower taxes than Trumbull, nice people, the train station, and beaches.

I grew up nearby and live in Shelton now. I visit a lot. There's no horrible section, but Devon is seen as less desirable. My grandparents lived there two years ago for a year though, and there were no problems. They got into an apartment by the beach which is obviously seen as better, but Devon still wasn't that bad.

I live in Shelton now after growing up in Trumbull. Shelton is great, but I think Milford is better as well. If you are looking at something like Fairfield try Trumbull. Slightly cheaper homes and better taxes than Fairfield.

Milford is my go-to recommendation for young families. I lived in the Devon section for a while but moved to a bigger house in Orange, which is also a great town.

Milford has lots of family activities and a great downtown. Unfortunately both Milford and Orange do not have much housing inventory. Good luck!

Are either you or your partner going to be commuting?

If you're not familiar with CT, some towns that are close together can be challenging to get between based on direction and time of day.

If you guys are remote, then I would just look for the town with the best school system you can afford. Can always drive to Milford or Norwalk or Stamford for that more urban feel.

I live in the next town over at my in-laws house. My wife and I just played "house" on Sunday wandering through Milford to feel it out for ourselves. Still trying to figure out where we want to settle. But we also enjoyed how Milford felt. We like the downtown feel of Milford but enjoy the lot spaces in Orange and Woodbridge more. Trumbull also has some nice spots.

Funny! When I was at Foran (early 2000s) it was considered worse than Law. I’m sure it shifts from time to time

Houses are worth what people will pay for them. If you think something is truly overpriced (I.e. it’s been sitting on the market for a while) you can always try to make a lower offer.

I mean neither one is bad so they could both move around academically by a few points.

I grew up in Trumbull and our middle schools did the same thing. I went to Madison and sometimes Hillcrest was better and sometimes it wasn't.

I recommend Trumbull over Fairfield though. Better taxes and just as good of schools.

Unfortunately Stratford public schools have gone downhill academically. You can go to magnet schools of course, but you can get the same priced house in Shelton with better schools attached.

The issue is the public schools have gone downhill. They have great magnet schools down there, but better public schools are available in other towns.

So no when we are in CT we will both be working from home but she will need to go back to her office out near Syracuse every so often which is why Milford is as far east as we would like to go.

You've mentioned Newtown a few times in your replies. I grew up nearby, and if you've seen houses in a good price range I think you should follow your instinct and check it out some more! A pretty main street (that goes hard for Halloween and Christmas lol), a pleasant walkable area in Sandy Hook, a handful of good restaurants, pleasant paved walking at Fairfield Hills, as much hiking nearby as you could want... My hometown is similar but all woods and I'm sometimes jealous of the relatively livelier center of Newtown. Then of course the convenience of these towns is just hard to beat. From Newtown you're a quick drive from the food and stores and recreation in Bethel (my favorite town 🥲--actually, move to Bethel), Danbury, Brookfield, Trumbull, Monroe... an hour and a half from NYC on 84, half hour from the train to NYC at Southeast (in NY state)... Seriously, you could also check out Bethel, though it's smaller-feeling than Milford. (I'd say Redding too, for maximum nature-convenience balance, but you specifically liked the sidewalk in Milford, and the housing market is maybe not great in Redding.)

In that case I stand by my advice to look for the best schools you can afford.

So my wife hasn't seen Newtown yet but I have and I really liked it. It feels like the sort of town I'd want to raise a family in. I'll have to check out Bethel too!!

But Fairfield has four beaches and two marinas and three yacht club. If you like water or sailing, it’s something to consider.

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   Lived in Milford for 10 years. Its an amazing town. Just be warned home prices have grown a lot over the last 3 years, more than most places in CT.  Its also over-crowded. If there's the tiniest lot available, someone will build on it. Parking downtown or at the beaches has become unbearable. 
   Some streets flood, including ones a mile away from the beach. There are some neighborhoods barely above sea level, so do your research. Those are obviously the ones on the water. 
  I still recommend it. Its got everything! But do your research. That can be said about any place.

I love woodmont, I launch my kayak off Belmont st right at the beach. I’m more inland (Brookfield,CT) but if I had to choose where to move to next, woodmont would be it for sure. Super nice people in that area.

We just bought a house in Milford last year (moving from NYC) and couldn’t be happier. Looked at basically everything between Stamford to New Haven and Milford checked off most of our boxes (affordability, schools, beaches, train station, dog park, etc)

Milford is awesome. I lived near Newtown in Bethel and it was a little too sleepy for me. Milford feels more vibrant if that makes sense. And friendlier. Also being near New Haven is a HUGE plus. So much culture, entertainment, food, cool areas to walk.

There’s a lot more areas than Devon and Woodmont though.

Newtown is very different from Milford. More wooded and quiet. Not as much going on and people tend to be less outgoing.

North of Route 1 in Milford has bigger lots.

Actually Trumbull taxes (mill rate) are higher than Fairfield’s.

I’d disagree with parking. If you know where to park it’s fine. I never have an issue and go to downtown almost daily, and beaches often.

Your assessment is correct. Great if you don’t have kids or can afford private school $$$. If you don’t have to commute to NYC, there’s no good reason to choose it over Milford.

Yeah I live in that area but I'm in Orange. Milford lots are still a little bit smaller over there than I personally like. Woodbridge is the ideal size. 1.5 acres minimum with plenty of trees between neighbors.

shelton lower taxes good schools

That's a good point about New Haven--I love New Haven and would spend a lot more time there if I lived 15-20 minutes away rather than 45.

Good point about the schools, I’m unfamiliar with them. I don’t like Shelton. But I don’t have a valid reason why, I just don’t.

Its not very built up. It's schools are comparable to Milford, but Milford has more to do and a train station that goes right to NYC, so more people move there, but Milford is more expensive.

My friend is on 1.5 acres in Milford near Orange but I get your point