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Ok, have been house hunting for a year now -- looking mostly in Trumbull and Shelton. Shelton definitely gives you more value for your money, less taxes, but the school district is not as good as Trumbull, so my heart was set on Trumbull for that reason. But it seems every home we see, either we like the home but HATE the rocky/hilly property (my hubby is set on having a pool one day) or the property is ok and on the flatter side but house needs SO much work...more than we can afford. I'm getting really frustrated. Perhaps we need to rethink the town, and forget about Trumbull?
I'm from north shore Long Island (30 min from Manhattan, on the water, excellent school district, very family oriented, lots of shopping, walkable, and good restaurants). My husband is from Stratford originally but doesn't want to live there again -- and moved into NYC right after college -- he's more of a city person. I think if money was no issue, we would live in Westport, but we can't afford it. I would love to find a family-oriented town with lots of activities, great schools, sidewalks - I love to walk, shopping/restaurants/nightlife (this could be a few towns over...I think we would end up heading to New Haven for music, etc).
I am starting to think maybe Trumbull isn't really the right fit...might just be too rural or residential for us, maybe not diverse enough. My SIL lives in Milford and keeps telling us to look there -- but aren't the schools not so great? And Fairfield I love whenever we have driven through, but our realtor seems to keep telling us not to go there...something about the people? My other SIL & BIL live in Shelton and have only good things to say about it, but again is the school district any good? Would love to hear what locals think of these 4 towns. Thanks!!
Everyone I know from Fairfield and Milford Loves it. Close to the water, proximity to New Haven, convenient to Metro-North, decent shopping/restaurants, etc. I have friends in Shelton and they're dying to move out, there are not as many things to do there (according to them). Not sure about Trumbull -- I've always thought of it as rather rural, but only compared to the more bustling towns in lower FFC.
Your realtor may be steering you away from Fairfield because of the price. It is definitely more expensive than the other towns you are considering. And is the most desirable. Fairfield is a somewhat diverse upscale town with a large range of housing types and a lot of different types of people. If the realtor is saying that there is something wrong with the people in Fairfield, I would find a new realtor because they obviously do not know the town (another reason they may be steering you away from it). If you like Westport but can't afford it, then Fairfield would be the next best town for you to look at. I know many people who bought in Fairfield because it is less expensive and then stayed because they liked to town so much.
Milford too is a great town. The schools do not perform as well but they are still considered to be good. Your money will go further there but you will be further from New York.
Trumbull is very suburban in character. There is no walkable downtown. The schools are excellent though and there are a lot of family activities. Shelton is nice but IMHO, not as nice as Trumbull or Fairfield.
My advice is to look at both Fairfield and Milford and see which fits you and your husband best. Good luck, Jay
Milford and Fairfield seem like they would fit you best. Milford schools only test slightly above average on test scores, but I know people with kids in the system and they're very happy with them.
Jay -- so funny, our realtor actually grew up in Fairfield (prob why she hates it) and now lives in Stratford. I know Fairfield is more expensive, but I think we would sacrifice house size for quality of life and having things to do around town.
Also, I know a few people that went through the Milford school system and are VERY successful, went to top tiier/Ivy league schools, etc.
It's all about what you put into it. Sometimes more middle class communities have more kids that come from not as ambitious families and it's not the school's fault they test lower.
There's just as much going on around town in Milford than Fairfield. I personally prefer the restaurants and amount of shopping overall, and there's more of a variety of beaches and parks. Plus, Fairfield doesn't have a green like Milford which becomes an epicenter for town events year round. Downtown has a thriving nightlife scene too with 7 popular bars, if you're into that. I'm actually really impressed with the activity down here after moving from the Danbury area (which is comparatively dead). So there's really no sacrifice going to Milford and you'll get more house for your money.
That said, you can't go wrong with either town IMO. If I were you, my priority would be finding a house you like. I would live in Fairfield in a heartbeat, but chose Milford because I got more house for my money and was able to live near the water.
You really can't go wrong with any of those places. Now, you say you're from North Shore Long Island, 30 min out of Manhattan with a great school district and a walkable downtown. Now, you say you can't afford Westport, but all the info you gave there leads me to believe that you most likely live in a pretty expensive/affluent area of LI. Maybe I'm wrong, just seems that if you can afford an area like that you should be able to afford Westport/Fairfield.
Anyway, that's beyond the point. Fairfield is diverse, has a walkable downtown, is on the water and has a great school district. The next best town out of all that you have mentioned is Trumbull. Trumbull is the definition of Surburban as far as Connecticut goes in my mind, but compared to Long Island I can see why you feel it's a bit rural.
Shelton is nice, the Huntington and White Hills Sections are the most desirable but there school system does not rank near Trumbull or Fairfield. Milford's school district is fine, but like you said, compared to the other towns not as "desirable".
You say you don't want rural, but I think you should give Newtown a try. It is semi suburban/rural, but it's beautiful with great schools. It's kind a small downtown in Sandy Hook with offices and restaurants and Route 25/Main Street is lined with beautiful Victorian Homes, Town Hall a few Restaurants (The Inn), etc with sidewalks. Bethel, the next town over offers a downtown and New Haven is not that far. You'll still be somewhat close to NYC if you ever want to go in for an evening, etc.
but I think we would sacrifice house size for quality of life and having things to do around town.
This would indicate to me that Fairfield is your best bet. Trumbull is great. Very family oriented with lots of youth activities with very good schools. However, if you want more to do, better shopping, beach, etc, then Fairfield is a better bet. Fairfield schools are a tad better than Trumbull's and then town is full of restaurants, five beaches, and all the youth and family activities that Trumbull has... Plus direct access to the train to Manhattan
You say you don't want rural, but I think you should give Newtown a try. It is semi suburban/rural, but it's beautiful with great schools. It's kind a small downtown in Sandy Hook with offices and restaurants and Route 25/Main Street is lined with beautiful Victorian Homes, Town Hall a few Restaurants (The Inn), etc with sidewalks. Bethel, the next town over offers a downtown and New Haven is not that far. You'll still be somewhat close to NYC if you ever want to go in for an evening, etc.
I come from that area and honestly think the OP would grow bored with it, especially coming from the north shore near NYC. It feels more disconnected being away from the coast, which some people like - but not those looking for walkable shopping, restaurants and activity.
Btw, in terms of cost, 1. Fairfield, 2. Trumbull, 3. Milford, 4. Shelton. The gap between Fairfield and Trumbull is the biggest. Supply and demand drives price, which you can call desirability (although I find that to be subjective).
MetsNY - my husband commutes to NYC so I think Newtown would be far from the train...we are shooting for no more than 15 min drive to a train station. Also, yes I grew up in an affluent town, and we live here now but, we are renting!
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