Home Buying in New Canaan>Question Details

Diane, Home Buyer in New Canaan, CT

family of three,has always lived in the city(MANHATAN), and never lived in a house. any cool, unique town, close to transportaion with good schools?

Asked by Diane, New Canaan, CT Sat May 22, 2010

and bit scare of the basements and attics,

Help the community by answering this question:


Sam’s answer
I like the Town of Fairfield.
- Great public schools, if that is in your consideration set
- Train service to Grand Central runs a little over an hour.
-Good mix of people, diverse, non-confrontational, very nice & welcoming
-family oriented & welcome club

-Most likely you would need a car for travel within in town
-Homes tend to be on the older side, 50+ years or older = higher yearly maintenance cost

Hope this information may spark some interest and more questions. Good Luck!
1 vote Thank Flag Link Sat May 22, 2010
Hi Diane - If I were you - I would pick a weekend and take a tour of each city/town within your commute distance - that is if you will be traveling daily to NYC ie: 45 min by train to GC then visit the towns that meet that qualification - after reviewing the distance, travel time and towns amenities you will get a better sense and understanding of what is available in each of the communities. Price points vary in each of the towns as well as schools but actually seeing and getting a feel of the community is the best way in my opinion to see what fits your family best. Happy to help assist you and your family make the right move. Call me - Kerri 203-219-1123
0 votes Thank Flag Link Mon Jan 24, 2011
A former Manhattanite myself, you should be aware of a few home maintenance items:

Replace the A/C filter every month..it'll helps to reduce dust and prolongs the life of the system.
Don't leave bread out on the counter like in NYC..the humidity speeds mold and little ants will find it.
Get a hurrican/storm guide from the grocery store and prepare a litlle safety kit..yo might not have to use it, but having it handy is a good idea.

0 votes Thank Flag Link Wed Oct 27, 2010
Westfield or Summit N.J. Both are nice small cities with great schools and less than an hour ride by rail into manhattan.
0 votes Thank Flag Link Wed Oct 27, 2010
Hi Diane -
All good responses from others; I might add that all towns within a reasonable commute to NYC (~ 1hr) are different – of course similar in many ways, but also very different. Isn't it the same in NYC? The East Side is not the same as the West Side, the Village or mid-town - right? The same is true here in the burbs. Anyone living in Greenwich would never compare their town to Darien or New Canaan, and vice versa. Like NYC, there are micro-markets within each town too. This means it comes down to lifestyle – your personal lifestyle preferences. My wife and I were in your sneakers nearly 18 years ago and would recommend experiencing each of these communities first hand. You can do this on your own or through a qualified real estate professional. So while the leaves are peak-gorgeous and the weather is still moderate, why not pack-up your herd in a car and head North to walk through each of the communities you are considering. You won’t regret the exercise and in the end, it will help you to decide which community to focus your search. Hope this helps – cheers.

Stephan von Jena
William Pitt / Sotheby’s International Realty
1057 Post Road
Darien, CT 06820
(W) 203-655-8234 ext# 303
(F) 203-655-4046
(M) 203-434-8472

Proudly servicing the Darien, Rowayton and New Canaan markets.

"Artfully uniting extraordinary homes with extraordinary lives!"
0 votes Thank Flag Link Wed Oct 27, 2010
Hi Diane,
I need more info on what YOU feel is "cool & unique" I have plenty of ideas, but to do a great job responding, I need to pick your brain a bit. I cover ALL of Lower Fairfield County and if you are not under contract with a Realtor, I would love to help you, so give me a call at 203-218-6664. Thanks!
0 votes Thank Flag Link Tue Oct 19, 2010
Hi Diane,

I have lived all my life in CT and spent much of my career commuting to NY. Here are some suggestions for towns: If you want to be on the CT coastline -- anything from Fairfield, Westport, Norwalk, Rowyaton, Darien, Greenwich are all great towns with train access to NYC. [homes are more expensive along the CT coastline; however the train ride can be shorter.]

If you prefer more of a country life style -- then I would suggest, Brookfield, Ridgefield, Newtown and Bethel. All have access to Metro North. Homes are less expensive in Northern Fairfield county; however the train ride is longer.

All of the above towns have great schools. I would encourage visiting the schools and contacting each school's PTA/ parent teacher association. There are also a number of private schools in Fairfield county.

Do not be scared of basements and attics --- they are just places to store stuff. I do not use my attic or basement!

Happy house hunting. PS. I currently live in Brookfield and my home is for sale -- 4 bedrooms, 2.5 baths, big, beautiful back yard for children, boating, hiking nearby. [We are retiring and relocating.] Check it out 19 obtuse rocks road, brookfield, ct.
0 votes Thank Flag Link Mon Jun 28, 2010
I lived in lower Westchester for about 8 years (part of a gradual movement north out of NYC) in a few of the Hudson River towns Irvington, Hastings, Dobbs Ferry-only 30 minutes north of Manhattan by train Metro North Hudson Line or car
I have lived in Pound Ridge NY- Northern Westchester -on the border of New Canaan CT and I have been selling real estate for a decade in Greenwich- New Canaan-Darien-Wilton-Westport-Weston-Fairfield CT area.
Sometimes a gradual move out of NYC is easier than an extreme move. The lower Westchester river towns are very artsy, relaxed & small town with great views and easy access back into NYC. You can look up the school information online.
CT TOWNS-Fairfield County CT -You can't go wrong with Fairfield County CT towns..CT has a much more suburban feel than the Hudson River towns. There are plenty of other cool location options depending on your search criteria
Call me if you want to talk about all of your options.
Hannelore Kaplan kaplanh@raveisre.com 914-450-3880
0 votes Thank Flag Link Sun May 23, 2010
Hi Diane,

The best place to reference Metro North train stations is the MTA website. The red line is the New Haven line. You can click on each station for more information.


Robin Lynch
Keller Williams Realty Group
0 votes Thank Flag Link Sun May 23, 2010
Diane: As a 16 year Darien resident, I must admit I am biased and very knowledgeable. I am a local realtor specializing in exceptional properties in Fairfield County and am familiar with all the surrounding towns. Darien offers great schools, an easy commute, and is central to most everything you need including beaches, parks, good hospitals, shopping, Manhattan, Vermont, Long Island, Rhode Island and Westchester airport. Darien has a wonderful school system which you can verify on greatschools.com and all our children have had good experiences thus far. Darien also offers a great athletic program for both boys and girls, as well as an arts program which includes band, orchestra and chorus. We also have ballet, drama and many options for artists. Darien is currently undergoing a resurgence in new business options, with seven new restaurants opening in the next few months along with a Whole Foods. Darien has a wide range of price points which makes it a wonderful diverse community for all. Please contact me at 203-554-0897 or mgmcg@aol.com and I will send you listings available in any community that meets your criteria and price point. I Look forward to working with. Sincerely, Deirdre McGovern
0 votes Thank Flag Link Sun May 23, 2010
I know a number of the agents who have answered your question and they are right on the money.As an agent in Darien I am partial to this town which offers what you are looking for.To get a feel for Darien,visit my blog,
0 votes Thank Flag Link Sun May 23, 2010
You have received some great advice. Although we as Realtors cannot speak about the quality of schools due to guidelnes we must adhere to by law, I would recommend typing in a search "Town Hall of (type town) CT." On all the town government sites are links to the schools including test scores, magnet schools, individual schools, etc. All schools have their individual strengths. For example if music is important, some schools may have more programs than others. There is also indepth information about ammenities under different departments such as Parks and Rec. Also, type in a search "Chamber of Commerce (type town) CT" and they will have much information about the businesses and activities in the area.
The following is a list of towns along the Metro North line including the spurs that lead to interior towns. First stop along the coastline is Greenwich, then Stamford, Darien, Norwalk, Westport and Fairfield. There is a spur that leads to New Canaan and from Norwalk there is the spur that leads to Wilton, Redding/Ridgefield. With each stop add about 10 minutes further for each town up the line.
As mentioned below, knowing your price point is most important.

Any one of the agents who answered below are very qualified to advise you as well as I hope myself. I also recommend you network with friends, family and colleagues. They will give you even more insight.
So do your due diligence and happy exploring.

Candy Lipira

Candace Lipira, Realtor
Keller Williams Platinum Properties
0 votes Thank Flag Link Sun May 23, 2010
The best advise I can offer based on your wish list is Darien and New Canaan. Both rate high in Education,and very close to transportation. Small Town feel without being rural. Check out their Town Web Sites.http://www.darien.org/ , http://www.darienps.org/current/ , http://www.newcanaan.info/

Joan Gallagher (Realtor)
Darien, New Canaan, Rowayton
0 votes Thank Flag Link Sun May 23, 2010
Diane, another thing that may help you make a decision as far as town goes is to nail down a price range. Although many towns have a range of prices, there may be some where you will be more likely to get what you want for your money than you can in others. If you want to talk about that, please feel free to contact me and I would be happy to go over it.
On another note, defining what you mean as cool and unique is in your own eyes. You are not going to be able to replicate a Manhattan feeling in any of the suburbs, as much as they might try. You can make a nice life there for your family, and enjoy each town for it's own plusses. Even if you are not quite as close to the city as you might like, there is a lot to offer. My company's main office is in Stamford, and I pass by 2 theatres on the way between 95 and the office. There are also loads of restaurants of all kinds. Not that I would suggest living in downtown Stamford, but it is close enough to take advantage of from any of the towns that have been mentioned.
0 votes Thank Flag Link Sun May 23, 2010
Hello Diane,
You've gotten some very good information. Originally from NY, I am happy to share some deeper insight into Darien you may find helpful. Darien’s a great small town with many advantages; top-notch schools, low taxes, 2 public beaches, 6 public parks with ball fields, soccer fields, tennis courts, and multiple YM & YWCAs. With a short direct commute to NYC it's preferred by many who move to the area since most of us come from other parts of the country.

I hope you don’t get sticker shock, but real estate in this area is a very good investment. Here's a neighborhood video tour of Darien http://www.halstead.com/properTV.aspx?video=057B4937E3 and if you would like to learn more or schedule time for a tour just give me a jingle.

Samuel Gabe
Halstead Property
Licensed Realtor®
Halstead Property Connecticut, LLC
671 Post Road, Darien, CT 06820
t: 203.656.6518 | c: 203.856.8399 | f: 203.655.9857
sgabe@halstead.com I halstead.com
My blog: http://www.trulia.com/blog/samgabe
Web Reference: http://www.halstead.com
0 votes Thank Flag Link Sun May 23, 2010
Hi Diane,
You're starting to assemble a good list of criteria. What I hear from your basement/attic comment is you might have a preference for newer construction, with a finished basement. If you've always lived in the city, how important is a town center to you? As a former city commuter, I can answer your questions about the train, parking and pro/cons of towns' stations. I'd be happy to probe further into what is "Cool and Unique" to you and help you further define your "wish list" into your dream home.

Carol Barbour,
0 votes Thank Flag Link Sun May 23, 2010
Darien, New Canaan, Westport. It depends on your budget. Darien and Westport has beaches, New Canaan has the town center and you can still visit the beaches. All have good schools, Darien and Westport are more populated. All have train schedules into the city. In recent Connecticut Mag rating of small towns 10,000-15,000 New Canaan ranked 1 in schools
0 votes Thank Flag Link Sun May 23, 2010
Westport, New Canaan are good possibilities, depending on budget.
Wilton is a little smaller and quieter.
Web Reference: http://www.marionfilley.com
0 votes Thank Flag Link Sat May 22, 2010
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