[antoluca]

My husband and I are considering a move to Wesport [or Weston or Wilton]. We started exploring and I fell in love with the whole area....the setting, the beauty, the shopping. I think I would love it but one never knows. We have been on LI for a while now and own a house in the Lloyd Harbor area. Here is my big dilemma. It seems that the schools in Westport are just as great as where I am now living. It seems to be just as much of an affluent area and yet I belive from what I have seen that you can get more for your money. We pay millions here and in Wesport or in Wilton its about 500,000 cheaper. Leads me to want to move and get a 5,000 square foot home [that I would have to pay 2.5 to 3 million in the area I am in now] in Westport or Weston!!! Why is Long Island's North shore sooooo expensive. Those parts of Fairfield county seem like a better deal to me. Is there something I am missing? Of course Greenwich or Darien would be more along the lines of where I live now but I am not looking for that. Can anyone shed some light.

[JayCT]

The cost differences has to do with the travel distance from New York City. In real estate it is location, location, location. It is easier to get into lower Manhattan from Long Island than it is from Westport and there is a larger pool of buyers for the number of homes available. That is why it is generally more expensive to buy in Greenwich than Darien or New Canaan and more expensive to buy in Darien or New Canaan than Westport, Wilton or Weston. Schools in Westport, Weston and Wilton are excellent and believe it or not, your property taxes will most likely be less here in Connecticut than on LI. This is because Connecticut does not have the mulit-layers of government to support that New York has. You may have some trouble adjusting to the less shopping that is available here since LI has many many of the great NYC stores, but the city is not far if you need something. I am glad you like the area and come on up! Jay

[yankeemom]

I currently live in Wilton, and agree the area is lovely. You would probably get more for your money in Weston, as compared to to Westport or Wilton, but I have friends who live in Weston and complain that their real estate taxes are higher because there is little commercial businesses to support the taxes, so private residences/cars are the only source of income to run the town and schools. Westport is the most expensive of the three towns, but it does have a great coastline, and a very nice downtown shopping area. In Wilton, there isn't nearly as much shopping, but I easily bop to Ridgefield, or Westport. Or Danbury or Westchester if my teens need a mall fix. We find it easy to use Metro North to get into the city for shopping or theater, and since Wilton's line runs less frequently, we just drive into S Norwalk or Stamford to get on the main line.
PS There are quite a few displaced New Yorkers here, and I would recommend joining a newcomers group as an easy way to make friends.

[jumper]

Having lived in Manhasset, and now in Ridgefield, I have an informed view.
You have these choices:
Quality of life..better in CT, mostly traffic issues deter me from choosing
NS, although Westport traffic can be positively brutal.
Schools...Ridgefield, Wilton and Weston compare favorably to
Manhasset. Personally, not impressed with Westport as much.
Amenities..restaurants, entertainment, etc. on par with the NS.
Housing...More bang for the buck, but the best barometer is the tax
rate and the rate of change.
All in all, our family loved Manhasset, and loves Ridgefield.
CT has everything that the "Gold Coast" offers, with somewhat less
stress.
Good luck. For more insights, you can e-mail me privately.
Dan

[JayCT]

Originally Posted by jumper

Personally, not impressed with Westport as much.

Dan - Why are you not impressed with Westport Schools? They consistantly rank near the top of all schools in the state and Staples High School is ranked one or two. Connecticut Mastery Test scores for Westport are higher than Ridgefield, as is most scores on the Connecticut Academic Performance Test. Class sizes are generally smaller in Westport than in Ridgefield as well.

Don't get me wrong, both towns have excellent school systems, but Westport is consistantly ranked at or very near the top. I am not sure why you would make a statement like that given what I have seen and know of the Westport School system. Jay

[jesse rivers]

There are some subtle differences between Long Island's North Shore towns and Fairfield County, as I have lived in both. New York is friendlier but most people are harried and hurried. CT people are more relaxed but not as warm. Shopping is sparser in CT, but their is less emphasis on the spoils of shopping, more on family and on the house itself. There are more upscale towns in Fairfield than on LI, fewer upscale towns left on LI. There are more actual towns to visit in Fairfield Cty, but LI has more strip malls -- too many in fact. Long Island has many roads to commute by, Fairfield really only has the Merritt and I95. LI has the ocean and the sound, and CT has some hills and countryside. Crime is very low in most parts of LI, lower than even in the lowest towns in CT. However, it is easier to own a gun in CT than in NY. The bad areas on LI don't compare to the bad areas in CT; CT is much worse! LI is more convenient to access all kinds of things, and less driving is required to run errands. Schools are terrific in both areas and there are really nice kids in both areas. But I suppose the deciding factor will have to do with your life's aspirations. What do you want to accomplish personally? What kinds of friends do you want to have? What are your causes, hobbies, and pursuits? Is your spiritual life an issue? And what do you feel may be lacking now, and is it realistically available elsewhere? Keep in mind that there is a certain percentage of transiency in both locations, so if long-term associations are important, you might need to google that info in both places of interest. There is more work on LI than in CT for young people, but that depends what type of occupations they are pursuing. But all in all I would have to say that the mood on LI is definitely more entrepreneurial and recreational, whereas in CT it would be more corporate and community oriented. That might be the key.