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Living in Westport CT is amazing.. but it's not all roses here. Today we are going to talk about some of the good things, and some of the not so good things, for people who are considering moving here. Let's go.

Hi, my name is Charlie Vinci. I am a Westport CT Realtor, and my realty team and I specialize in helping buyers understand what living in Westport CT entails and how to relocate to the area.

Let me show you why you might want to move here, AND a few reasons why you might not..

Table of Contents:

Pro: Lower Housing Prices Compared to Greenwich & New York

Con: Higher Housing Prices Compared to Other Towns in Fairfield County

Alright, let's talk about the elephant in the room. Relative to most of Connecticut, prices are high here. The average home price is north of $1.7MM and increasing as we are filming this video. 

You can move to Norwalk, Stamford, Fairfield or Wilton, and get more home for the money, and this is going to be a good option for some people. 

The challenge with Norwalk and Stamford specifically, are that the public school ratings are much lower according to and every other site I have seen. Now, you could send your children to private school, and have a smaller mortgage in these towns, and this does work for some people, but there are some financial disadvantages to this approach which I'll explain in a minute. 

On the other hand you might consider Wilton or Fairfield If schools are important, because they have better school ratings than Norwalk or Stamford.

PRO: Only About 60 Minutes to Grand Central

CON: Commuter Traffic

If you are commuting to New York City by car, the traffic can be very heavy during rush hour. So plan for the extra time or shift your commute time if possible. But Westport will have a shorter train commute to Grand Central Terminal. 

PRO: Excellent Public School Ratings

Financially savvy people like to buy homes in towns with high school ratings because they help keep real estate values high.

PRO: Low Taxes

Another thing that financially savvy people like are low taxes. Nothing sucks the life out of an investment like fees, and well, taxes are just a fee. Westports taxes are some of the lowest in the state. 

PRO: Low Violent Crime Ratings (According to

If low taxes and high school ratings didn’t encourage the wealthy to invest their money here, then the low violent crime ratings would. Living in Westport you are 27.1 times less likely to be involved in a violent crime compared to an average town.

PRO: Excellent Real Estate Investment

I have noticed that many of my buyers have clued into the fact that it makes better financial sense to pay more for your home, and less for your taxes, because your home can appreciate in value, while taxes are a liability.

To maximize the return on your property taxes, Westport’s excellent school ratings (According to better than many private schools, and you can write off a portion of your property tax.

Throw in the low violent crime rating and you have an excellent investment in a town that other financially savvy people want to live in. I know, I know...You can thank me by inviting me to your Boca Raton estate when you retire.

CON: Poor Walkability 

If you are moving from the city and are used to walking or using public transport, life in the Westport is going to take an adjustment. Outside of the in-town area, and perhaps near the Westport Train Station, walkability in Westport isn’t amazing. You will have to get used to driving everywhere, most of your neighbors will have two cars. Check out our walkable areas video for more information.

Pro: Suburban Lifestyle

If you want the ability to step out of your back door into your own private park, well, Suburban living is hard to beat. Plus, You will be minutes from beaches, golf, boating, hiking, farmers markets, waterfront shopping, theatre, top notch dining, you get the idea.

And you are going to be able to choose anything from a secluded estate, to a small community where the kids play in the street.


If you are still exploring, check out my website where you will find my raved about local buyers guide, neighborhood maps, and all of the homes listed for sale in Westport.

I hope you enjoyed this tour as much as I enjoyed making it for you. When you are ready to start shopping, call me, I’ll help you find a great home.

I look forward to hearing from you!


Charlie Vinci


Westport CT Realtor

About the Author:

Charlie Vinci, the Founder and Lead Agent of the Charlie Vinci Team has become a mainstay in Connecticut’s real estate market, earning accolades as one of the top 3% of realtors within the state. Fueled by a dedication to the success of his clients and an ever-growing assortment of area-specific resources, the business continues to thrive in the constantly evolving real estate marketplace. An informative YouTube presence has been the primary driver/focus for the team, as it has allowed Charlie to engage directly with his audience and provide a consultative approach to an often ambiguous process. Whether an international client seeking relocation to the US or a local homeowner considering the sale of their property, The Charlie Vinci Team has the market knowledge, resources, and expedient level of service that clients not only desire, but deserve.

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