Best towns for a childless, middle-aged couple?

Submitted by CatsNSquirrels t3_z5bjxn in Connecticut

Hi all. We’re super excited to finally be in Connecticut after escaping from Texas. We love it here. We have landed in Stamford in a rental, and are starting to think about where to settle permanently and buy a home.

Can anyone recommend some good towns for a childless, middle-aged couple to settle and find community? And also not be bored? I did a search but didn’t see any posts like that.

We owned a home in suburbia prior to relocating, and didn’t make any friends. We were surrounded by young families and retirees. There was literally nobody like us! We were also horribly bored because there was no culture, live music, events, sports, arts, nature, nothing. Dining was rather limited too and there were a lot of chains.

Note: we work from home so can live anywhere.

Thanks!!

Edit: Thank you SO much everyone! I deeply appreciate all of the comments. Sounds like the top recommendation is New Haven, so I’m definitely going to look at it more. But other popular recommendations are Middletown, Mystic (and nearby area/towns) and Norwalk. West Hartford was recommended by some and not by others.

We like the shoreline a lot, so will probably focus more on the shoreline recommendations. Thanks again!!

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Maverick8200 t1_ixv40p8 wrote

I am 36 and my wife 30, we have lived in CT for 9 years, we are 100 percent aggressively looking to move to Stonington/Groton area, aka Mystic. Amazing restaurants, awesome little town. Super convenient to highway. 20 minutes from casinos. We visit now almost every weekend just to get dinner and get some scenery in. Every time we go we try a new place and nothing has been a let down.

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Prestigious_Bobcat29 t1_ixv4spl wrote

New haven, Milford, Middletown, Willimantic..I have a soft spot for derby/ansonia and downtown Shelton too

12

BrutallyRational t1_ixv5drq wrote

New Haven may be a good option for you. Lots of great restaurants and cultural events, and you get a great mix of people (not just young families and retirees). Stamford is also a great city, but since you can work from anywhere and don’t need to pay a premium to be less than one hour from NYC, your money will go farther in the New Haven area. Metro-North will still get you to NYC from New Haven in under two hours when you want to visit.

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B00ZE_TAN t1_ixv75nb wrote

New Britain, up and coming! Get in now while prices are low. Buy buy buy

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LoveIsLove75 t1_ixv9tw7 wrote

We've been in CT for 12 years now. It's tough if you don't have kids or dogs to meet people in the burbs. We were in Norwalk for the first 11 and moved to Stratford in April. We had a lot better luck in Norwalk meeting other middle-aged childfree couples. So far, the Stratford/Shelton area is very isolating and the people are "different". We found our neighbors in Norwalk a lot more welcoming and friendly. The people in Stratford/Shelton are very standoffish. After being here half a year I have narrowed it down to Norwalk having a lot more immigrants / people not from CT than this area. Coming from Norwalk, it's very jarring. We are counting down the months until our lease expires. We hope to buy back into the Norwalk area, if possible.

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LoveIsLove75 t1_ixvg9my wrote

Replying to Time_Yam301 (#689,700)

Agreed. However, I'd rather have a smaller place in Norwalk than continue to live in Stratford after our lease is up. We REALLY don't like this area. It doesn't feel like home.

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CatsNSquirrels OP t1_ixvi2bs wrote

Replying to LoveIsLove75 (#688,897)

Great info. Thank you so much! I can’t tell you how many times my husband and I have expressed being unable to make friends because we don’t have kids or a dog! So I really felt that statement. We have two rescue cats.

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LoveIsLove75 t1_ixvjag0 wrote

Replying to CatsNSquirrels (#690,008)

Glad I could help. We lucked into a unicorn situation when we first moved up. Our next door neighbors were a few years older and childfree. Through them we met their other friends who are childfree, as well. We still hang out with them to this day. After we moved, we realized how lucky we were in meeting them. A few years later, the F45 Westport studio opened and we made friends there, as well. The studio has a lot of 40-60+ members vs other studios in the area which skew younger and transient. The studio does a good job of cultivating a community-like feel. The other gyms/group fitness places in the area that I went to before (Planet Fitness/Edge/OTF) you can feel like a ghost there.

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Pruedrive t1_ixvl9q8 wrote

Middletown and Portland are awesome, and not super pricey.

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HorasLord t1_ixvnf9l wrote

Let me know if you guys need a great realtor reference!

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Beachynurse t1_ixvqbez wrote

Replying to B00ZE_TAN (#688,534)

Genuinely wondering if you're being sarcastic or if you have some good information. I have heard other people on the sub say the similar things about Bristol being up and coming.

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RedditZhangHao t1_ixvrocv wrote

Replying to jay_sugman (#688,865)

Narrow target: Augerville neighborhood along Whitney Ave, N of Skiff St up to Rt 15 in North Haven: Whitney Avenue, I91 and Rt 15 convenience to New Haven; near Canal bike trail; abuts higher tax Spring Glen and Centerville (without higher Hamden taxes); access to museums, cultural and sports (Yale and Quinnipiac), non-chain restaurants, pubs, coffee shops, Sleeping Giant State Park, etc.

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CommuteSleepRepeat t1_ixw1591 wrote

I think you’d like Niantic. It has that Mystic vibe but is easier to get around.

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husky429 t1_ixw36y9 wrote

Middletown for sure

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volanger t1_ixw4m2p wrote

Welcome to the civilized part of the us.

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draculasbitch t1_ixw4pnk wrote

Middletown. Houses are reasonable, downtown with restaurants, the CT river for boating, New Haven and Hartford 20 minutes each way.

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CTRealtorCarl t1_ixw7lua wrote

As others have mentioned, New Haven is probably your best bet. I think Westville could work really well if you are willing to drive/uber when going out.

Middletown great option too, nice downtown with unique shops/food but also close to other fun towns like West Hartford.

If looking for something a bit more rural but still "busy" with a good amount going on as far as community you may want to go take a drive through Canton/Collinsville.

Maybe take a look at some of the shoreline towns too like Milford and Branford (fairly family centric but good communities with a lot to do).

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krispzz t1_ixw9prj wrote

you might like west hartford. a lot of well-to-do middle aged folks dining and shopping in the center of town and blue back square. pretty decent for CT.

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beaveristired t1_ixwbdvl wrote

As one half of a childless, middle-aged couple, I heartily recommend New Haven. Lots of live music, arts, theater, dining, bars that don’t just cater to younger folks. Easy access to nature. On the commuter rail to NYC. Excellent community vibe. Recommended neighborhoods: Westville, Wooster Square, East Rock, Downtown, Beaver Hills between Goffee and Crescent, Morris Cove. Taxes are high but homes are often less expensive than suburbs. Nice old historic homes, most are well-maintained in the neighborhoods listed above. I’ve been a homeowner here for 10 years, free to dm me if you have any questions.

Also recommend Hamden (Spring Glen, Whitneyville, avoid Highwood).

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DropbeatsNotbombs t1_ixwbua5 wrote

Replying to krispzz (#693,622)

Not that great of an option unless you are using the public schools IMO. Taxes are insane, housing cost is insane. Definitely a nice town to live in, but unless you are using those public services, there’s much better options out there for your money.

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eggheadslut t1_ixwemf2 wrote

New haven. Lots and lots to do and lots of places to meet people. Stamford if you are looking for people who are business-like

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adultdaycare81 t1_ixwfc6u wrote

New Haven, Westbrook, any other shore town

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PikaChooChee t1_ixwgkxt wrote

How are you liking Stamford? I think it ticks a lot of your boxes.

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CompetitiveYak2311 t1_ixwhojr wrote

Who moves from Texas to CT. You’ll be scrambling back to Texas within 2 years

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ruthless_apricot t1_ixwki41 wrote

Why not Stamford? A big part of Stamford's appeal is it's proximity to NYC as it has the best trains to the city of anywhere in CT. For me that's a big deal, but it depends how much you like all the stuff New York has to offer.

If I was going for somewhere more beautiful with less good access to NYC, I think Ridgefield is lovely.

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SometimesILaw t1_ixwm45k wrote

Definitely the Westville area of New Haven. There are families of all ages there, parks, a cute little town center with farmers markets, arts fairs and restaurants. Close enough to downtown that you can Uber or drive in but don’t have the hustle of downtown New Haven.

That being said - I currently live in West Haven on the beach and during the summer there is always something going on on the boardwalk but the winters are usually dead (which can be nice as well).

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mrnyeah t1_ixwmxam wrote

Replying to BrutallyRational (#688,252)

Fellow new haven resident here. It’s a great spot to live. As a homeowner, expect to get killed in property taxes. So much land is owned by Yale (hospital and university) so essentially they pay zero property taxes and homeowners have to pick up the tab. I live in a 2 family home. Property taxes are almost $19K a year.

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uselessinformation82 t1_ixwnkuf wrote

Replying to B00ZE_TAN (#694,268)

I’ll second this. Erin has done a nice job in NB and it’s really close to everything that you’d want living in Central CT(WeHa, Hartford, J Timothy’s, West Farms) and SUPER affordable. Plus the water is the best in the state!

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Sufficient_Mirror_12 t1_ixwomby wrote

Replying to CatsNSquirrels (#695,694)

Norwalk > Stamford.

Norwalk has more charm and a community vibe while having that NYC proximity as well in my opinion.

It's also in between NYC and New Haven so the best of all worlds as far as the arts and dining are concerned.

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Some-Construction-20 t1_ixwrola wrote

Middletown or new haven are both options I think you would enjoy. Middletown, small city big town feel located centrally, cute main street and lots of activities.

New haven has night life, culture and more fast paced environment. Music, bands, bars, art, New haven is the cultural and culinary capital of our state.

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doughbacca t1_ixwt3b3 wrote

Westport / Fairfield if you need to be on the train line otherwise West Hartford

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4thbookintheseries t1_ixwtyc6 wrote

Another vote for New Haven from half of a child-free couple.

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STODracula t1_ixwucv5 wrote

With no kids, and considering the state as a whole, New Haven and West Hartford would be the two best option. If you have to stick to Fairfield County though, then just try somewhere close to downtown Fairfield.

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ianm82 t1_ixww7k2 wrote

Redding. It's beautiful, quite and close enough to all the places you'd love to go eat and shop. You can buy a really nice home for an affordable price, which still gets you a nice chunk of property. It's got more parks and trails than any other town in Fairfield County.

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lizardRD t1_ixwyw8y wrote

Someone else mentioned it but Norwalk is what first came to mind. Lots to do there, strong community, cheaper than Stamford.

I would avoid places like Westport, Darien, new caanan and Fairfield (that’s where I live) because majority of people have children in my experience from there. Big “mom community” in those towns.

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Lithsdith t1_ixwzgfc wrote

West Hartford is a great community. There's a ton to do in Blue Back Square as well as the cute down town area.

I lived there as a single female. It felt very safe and welcoming.

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giant_toad42 t1_ixx2cle wrote

Biggest question: Whereabouts in Texas were you?

If you were from the city:

West Hartford. Lots of stuff going on. New Haven, maybe too. Supposedly pretty neighborly ; but not my thing.

Really, I think West Hartford is probably the coolest pick - as there's a LOT of walkability in the center + always something to do there.

If you're more on the rural side - Northwest or Northeast CT are pretty good. Manchester or Vernon are decent with lots of good stuff around. Ellington / East Windsor / Bolton - rural farm-ish towns.

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ZestyItalian2 t1_ixx57hu wrote

If you don’t need to worry about schools and you want a nice area with plenty of action and adjacency to culture and activities, I’d say the Black Rock neighborhood of Bridgeport, New Haven, or Norwalk. All are also pretty quick shots into New York as well.

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Squadbeezy t1_ixx58vj wrote

I’ve asked a similar question on this thread and got lots of answers here!!

Good luck! We are in a similar position Colorado/Texas born lived in Portland, Oregon for my twenties and now 31, looking for an exit strategy. I’d love to follow your progress! We are maybe 1.5- 2 years behind ya.

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ZestyItalian2 t1_ixx5mf9 wrote

Replying to Hendrix811 (#695,835)

Half the reason to live in Westport is the schools. If that’s not a consideration, you’re just paying insane property taxes to subsidize other people’s kids. Also, Westport isn’t really an option unless you’re prepared to buy at $1M+. Even if you buy an apartment or townhouse or find a great deal, fitting in in Westport is tough unless you’re seriously wealthy.

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ZestyItalian2 t1_ixx61hf wrote

Replying to doughbacca (#696,617)

A little weird to move to either of those towns if you have no kids. Major family communities with high property taxes to pay for good schools.

If you like that area, Black Rock (which is technically Bridgeport) is right next to Fairfield except way cheaper, and Norwalk is next to Westport at a fraction of the price.

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cdmf6f t1_ixx7b4k wrote

You moved from Texas to Connecticut lol!?!?!??

−7

STMBK73 t1_ixx7uvg wrote

Another vote for New Haven area. We're in the same boat as you and there is a ton going on, both during the day and at night. Lots of bands come through town if you like music, a few different theater options, great restaurants and several museums. Feel free to DM if you have any questions!

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MurphMurphyAK t1_ixx8dwv wrote

Ridgefield. Amazing place, welcoming people. I’ve been a resident for 6 months and love it. Great music and shows at the playhouse. Great restaurants and the community social calendar is packed with events. Highly recommend, thrilled with the decision

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Meagz4 t1_ixx9e26 wrote

Danbury. Great restaurants, close to theaters for live music, an hour from mid-town Manhattan. Parks, bike paths…lots to do.

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Malapple t1_ixxbjt8 wrote

Your money will go a lot farther east of the CT river.

I like New Haven as well - stuff to do and amazing food options but you may find you have a much smaller property than you'd like.

I was blown away at how much land I could buy in Eastern CT vs. Western CT.

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boomajohn20 t1_ixxd4x3 wrote

I hear Austin, TX has a vibrant cultural community

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mugi_chan_lila t1_ixxdfvb wrote

Replying to CTRealtorCarl (#693,074)

Just started discovering Middletown, the downtown is awesome. Businesses look a lot more fun and interesting than weha, which is basically full of gangs of well off suburban children who have no where to go except for the ice cream stores. So yeah, I’m done w weha, if I had a choice I’d move somewhere in Middletown.

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curbthemeplays t1_ixxdz2v wrote

Milford/New Haven area for sure. Relatively affordable, lots to do, shoreline, excellent culture/dining in NHV (best in the state by far).

New Haven is so much better than Stamford as a city with personality, things to do, music, art, food. Stamford is kind of sterile and corporate in comparison. Stamford of course has the huge advantage of being near NYC, but now that I live in Milford near New Haven, I get my great city fix on a smaller, easier scale and don’t need to go into NYC that often.

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gahgs t1_ixxgkqb wrote

Replying to B00ZE_TAN (#688,534)

Honestly wouldn’t be surprised if in the next 10 years this is the “spot to be”. Has a bad reputation but it does feel like it’s up and coming.

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Chaos744 t1_ixxgtq7 wrote

You escaped Texas? Yay!!!!! Move to Waterbury. Very Liberal and welcoming. Vote almost exclusively liberal for mayor and state and federal representatives. Very low crime rate and a great place to live. Hartford and New Haven are my second and third picks to similar reasons. Welcome to Connecticut! ❤️

−3

lizardRD t1_ixxh9ed wrote

Replying to doughbacca (#696,617)

Westport and Fairfield are not the towns to be child free. People move here for the schools. Huge “mom community” here. I live in Fairfield, everyone has kids around us (we have kids as well). Not the area for people looking for childfree friends.

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CatsNSquirrels OP t1_ixxjzo0 wrote

Replying to Malapple (#699,331)

Honestly I want a smaller home. I had a large home in Texas and it was nice, but also sucked in so many ways. We aren’t consumers so not only do I not want to clean/maintain a large home, but I don’t want to try to fill it. Our TX home was more than half empty after almost 4 years there. We just don’t like to consume.

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Defelj t1_ixxkbhv wrote

Southington, west hartford

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AndrewJK99 t1_ixxli1t wrote

West Hartford is the best. Have lived here for 15 yrs with my wife. Mid thirties, no kids

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notgsxr t1_ixxmo8m wrote

I've lived in CT my whole life.... never would I expect to hear someone suggest New Haven... New Haven is the new Bridgeport.... and Waterbury? Well if you're super duper liberal I guess... and don't mind your car stolen once or 2x.. knock yourself out!

But in reality.. I love CT... just not what it's turning into... but it is home...

Danbury for the moment seems close enough to everything and yet... far enough away at the same time...

Best of luck!

−1

BoudiccasWrath79 t1_ixxp99j wrote

Replying to CatsNSquirrels (#698,176)

For the love of god don’t move to northeastern CT. Yeah it’s rural and pretty but if you say you escaped Texas you’ll find yourself right back in it if you move there. It’s a cultural black hole. I’ll put in another vote for the Mystic area as well as New Haven.

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ctusa73 t1_ixxqf4a wrote

Talk to a good realtor. We were looking rural low tax. The truth about CT is the more inconvenient the location the lower the taxes. But stacked side to side lower tax areas have better schools, less crime, because shit bags can't afford the entry price. There are sneaky low tax communities. Like 6 miles to a secondary state road and 25 minute round trip for milk. If you want closeness to anything price that. Want to live x minutes to blank... It's all taxes v. Service...

2

giant_toad42 t1_ixxxpc6 wrote

Replying to CatsNSquirrels (#698,176)

Sounds like NH/WH is your thing then.

Btw. Texas has the Right-leaning mindless zealots. We have the left leaning version of them. Anything that doesn't align 100% with their thinking and you're a fascist.

😔

Good news is if you have a professional job you probably will avoid the majority of the ignorant types.

−2

giant_toad42 t1_ixxxr47 wrote

Replying to BoudiccasWrath79 (#701,338)

Oh, you the one triggered by me describing the entirety of CT?

Way to be ignorant.

I ask "where are you from" because I understand not everyone is like me.

Also compared to Texas CT is tiny. Everything is close as hell here. Op can literally live wherever they want + be pretty close to everything we have to offer. Time to drive across Houston is the time it takes to drive from one end of CT to the other.

−2

LoveIsLove75 t1_ixyjbt8 wrote

Replying to Holl0wayTape (#697,747)

TLDR: Norwalk is a lot friendlier to transplants like myself than Stratford/Shelton.

I was thinking about this after I posted. I came to a realization that in Norwalk there were a lot more "transplants", while in the Stratford/Shelton area there were very little and most people that I met were from the area. I think transplants, like myself, go out and seek to make connections so we can be comfortable in our "home". Meanwhile, people that grew up in the area already have established social groups and aren't particularly open to new people. I don't think it's isolated to Stratford/Shelton. Any town that doesn't have a lot of transplants in it will probably be like this.

Picture going to work and you're used to saying good morning to each other as you walk by. Now picture your co-workers walking by you in the morning like you do not exist and only communicating with you if they need something from you. That's what I mean by "different". I feel like a "ghost" in this area.

I guess I am finally noticing the standoffishness that New Englanders are famous for which I never had to deal with in Norwalk.

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daisya257 t1_ixylm4h wrote

Replying to TrashPandaShire (#698,739)

It is and was designed by Olmsted, Vaux & Co, the same landscape architecture who famously designed Central Park. Is nationally listed as an historic park and is my favorite place in New Britain

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Aprilr79 t1_ixyvg9e wrote

1/2 of a childless couple here 😬I live in Hamden and really like it. Im in the Whitneyville section . Feel safe taking walks but love everything being close by. The playwright , coffee shops , stores etc .

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lizardRD t1_ixyzlzm wrote

Replying to mrnyeah (#706,644)

Wow! If it makes you feel any better I looked up in Fairfield some of the biggest houses property taxes. There is a 4 million dollar house up for sale now that’s property taxes are 69k/year!

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gottausername t1_ixz0kuf wrote

Most people recommend towns by the shoreline. However, I prefer the Storrs area. There's a lot to do: hiking, kayaking, plays & concerts at Jorgenson (UCONN), tons of sports -some free (swimming). As for making friends, I recommend joining a club- play softball, take a class at the community center or take a day trip with the community center program.

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frepont t1_ixzci8r wrote

Replying to Maverick8200 (#688,022)

We moved here recently from Boston, and would recommend. One perk if you can afford it: it’s also right on the train line and can put you in either Boston or NYC in a coupe hours (regardless of traffic)

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lizardRD t1_ixzcnyh wrote

Replying to CatsNSquirrels (#708,781)

Good luck! FWIW I think Norwalk has a better shoreline and beaches compared to Stamford. Checkout calf pasture. Loved going there when we lived in Norwalk. Very walkable, clean beach, Water sport rentals, restaurants by the water, mini golf and they often have concerts there during the summer. The beach is free to all residents.

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CatsNSquirrels OP t1_ixze1t6 wrote

Replying to ZestyItalian2 (#698,453)

As a native Texan, I can say Texas has gotten pretty gross. I’m ashamed of it. And I never used to feel that way. I thought I was going to live out my days there and now I never want to go back.

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CatsNSquirrels OP t1_ixzeo1i wrote

Replying to Malapple (#700,695)

Ah! Sorry, missed that. Yes I’d love to have a garden. I don’t need a giant one, but I’d love some space and trees without being too far removed from civilization. I love nature and wildlife. :)

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CatsNSquirrels OP t1_ixzg3oh wrote

Replying to volanger (#709,379)

People seem less miserable here, probably because they’re paid twice as much for what now is nearly the same cost of living (min wage in TX is still $7.25 and waiters still get $2.13). There is an attempt to care about the environment here. Texas is drowning in plastic and styrofoam, and they pave over almost all natural areas. People are more educated here and seem to possess more critical thinking ability. The Texas education system is falling apart (I’m a former teacher). Also I have my reproductive rights here and that’s huge.

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CatsNSquirrels OP t1_ixzghub wrote

Replying to volanger (#709,751)

Texas is very focused on money. Whatever is cheaper is what they will do. Most restaurants and fast food places use styrofoam. It’s gross. And there is plastic ALL OVER THE PLACE in Texas. It’s stuck in trees and all over the sides of the road.

3

curbthemeplays t1_ixzh7qb wrote

Replying to CatsNSquirrels (#708,772)

You said you’re buying. I would absolutely not buy in Hamden. The schools appear to be in decline, and the town is not run well. It has what you could call a runaway property tax issue. The mill rate is 55.48, which is insane. In comparison, Milford’s mill rate is 26.65.

Milford and Branford are also coastal, have train access (Milford’s better on the main line, of course), more well defined downtown areas.

Hamden is fine, it has good access to New Haven and some nice areas, but I’d never recommend someone buy there.

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RedditZhangHao t1_ixzi0oz wrote

Replying to CatsNSquirrels (#708,894)

Exact profile used by agent who marketed uncle’s house sold to couple closely matching your interests, age bracket, etc. They also liked they could hop on bus to New Haven and also to Sleeping Giant State Park for hiking. Good luck.

2

curbthemeplays t1_ixzitv9 wrote

Replying to CatsNSquirrels (#709,497)

It depends what you’re comparing to. Compared to New Haven, yes, a bit more family oriented. Compared to any other suburb in CT we’ve lived in, not at all.

We are a childless couple, in our late 30’s. We have other childless couples or singles in town we are friends with. Many I previously worked with who chose the town. The town is very popular for first time homebuyers, and is having a small apartment boom right now. It’s appealing to Millennial buyers because it’s relatively affordable for a southwestern coastal town (much cheaper than Fairfield), has good schools (unlike nearby Stratford and West Haven), has low taxes (unlike nearby Stratford and West Haven), low crime, good walkability (great downtown, and other walkable centers). There’s 3 breweries in town, independent coffee shops, good food. I was talking to a restaurant owner that had their location in Branford previously, and they mentioned how much more buzzing and young the town feels.

There’s also a lot of beaches, parks, a boardwalk, a nature sanctuary, tons of sporting facilities (tennis courts, pickle ball, etc). People are always out in the warm months jogging, biking, walking their dogs.

We are a 15 minute drive to New Haven. So we go 1-2 times a week to eat out, walk around, visit coffee shops, take in culture, see a show. Could also take the train just as easily, which, is super easy to access downtown.

Again, compared to most CT suburbs, this isn’t one of the dead ones full of homebodies.

New Haven is great. You should definitely consider buying in East Rock. But if you want a lower tax sibling on the coast that’s got some liveliness, it’s Milford. In fact, while I love Westville, it’s not super convenient to the rest of New Haven and I’d probably recommend Milford over that.

This site is a great summary: https://discovermilfordct.com

Also, I see you edited your original post to include West Haven. West Haven is great for those on a tight budget. The area of West Haven near Milford, West Shore, is a bargain. The rest of West Haven is fine, but a little rough around the edges. The city has serious financial issues, now the state is having to get involved. Again, it’s a good bargain. Taxes are high. Schools aren’t great, which affects resale. I’m not sure I’d ever recommend it over Milford, unless you were looking for cheap coastal housing in West Shore.

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Unhappy_Paramedic_41 t1_ixzma8p wrote

Stamford! I love it here. My fiancée is moving from NY,and we are buying a house in Stamford. I been here for about 40 years and always feel safe.

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curbthemeplays t1_iy00j9t wrote

Replying to CatsNSquirrels (#712,758)

Ohh, makes sense. Yeah, weirdly West Hartford feels a bit more family-ish than Milford. But still more diverse than other suburbs. West Hartford is a nice town though, depends how much you want access to shore/NYC as it’s a schlep to both.

1

ZestyItalian2 t1_iy026kv wrote

Replying to curbthemeplays (#712,985)

Fairfield is less expensive than Westport (though still quite pricy- Westport is the 9th wealthiest zip code in the country) but I’d say if anything Fairfield is more parent-y than Westport. You can be a rich single childless investment banker in Westport, but FF is wall to wall moms.

1

curbthemeplays t1_iy02dxf wrote

Replying to ZestyItalian2 (#713,106)

I guess my perspective is different, as several former colleagues and friends live in Fairfield without kids. On the other hand, the only singles or childless people that I know that lived in Westport hated it and didn’t last long.

1

DangerClose567 t1_iy1gdx9 wrote

My vote is Middletown and Mystic I agree. Middletown has really boomed lately and you're literally in the middle of everything haha

1

eggheadslut t1_iy1up8q wrote

Replying to CatsNSquirrels (#709,089)

I personally like westville. It has a lot of working class families and isn’t full of college aged kids as much as downtown is. But it’s also less than 10 minutes to downtown which is a plus

1

beaveristired t1_iy9hut6 wrote

Replying to curbthemeplays (#701,581)

Agree Branford and Milford are “nicer” and Hamden taxes are insane (worse than New Haven) - but OP doesn’t have kids. My impression is that there are fewer childless middle aged couples in especially Branford as well as Milford, but could be wrong. They’re also further out from downtown New Haven, 95 can be a barrier sometimes. And school quality doesn’t matter as much (although a well-run town is a bigger deal and agree that Hamden is struggling right now in that area) But yeah, Branford and Milford are also good choices. Personally, if I wanted to buy in the suburbs, I’d rent in New Haven first, get some friends, then buy in the surrounding areas.

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