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Living in Greenwich CT is an incredible experience.. But how does it compare to living in Westport CT? We are going to explore living in both towns and provide you with some pros and cons of each, so you can decide which area is a fit for you!

Hi! If you are new to the blog my name is Charlie Vinci. I’m a Fairfield County Connecticut realtor covering Connecticut’s “Gold Coast”, and my team and I specialize in helping people move to the area.

Be sure to check out our other guides for different price brackets, as well as upcoming waterfront and luxury buyer’s guides. Check out our YouTube channel for those videos and our blog for the articles. You can also find the associated maps and guides mentioned in this article on our website!

Table of Contents:

General Overview:

Our clients are often wondering if living in Westport CT is a good alternative to living in Greenwich CT, and this usually leads to a discussion about what matters most to them.

You can do a quick search and see that you generally get more home for your money in Westport than in Greenwich, but what are the trade-offs? Is one town a better fit for you? How much more home do you actually get? Let’s take a look and find out.

If you are going back to work in the city daily, you might want a shorter commute and Greenwich may be a better fit. But for my clients who are planning on working more from home, the extra twenty minutes on the train from Westport might not be a big deal.

More often than not, the main attraction to Westport real estate for my clients is Staples High School, which often gets ranked as one of the best high schools in the Connecticut. We have more information about the schools in our buyers guide which you can find at the link on the screen.

If you love the low taxes in Greenwich, you will find Westport taxes to be slightly higher. However, I don’t believe I have ever had a client who elected not to go to Westport because of this small difference. 

According to, the crime ratings are very low in both towns, compared to Connecticut and the United States as a whole, and none of our clients have said that this was their reason to choose one town over the other either.

Lifestyle & Amenities:

One thing that may be a deciding factor for you is the “vibe” of the town. While both towns are similar in many ways, and we do our best to highlight each town in our neighborhood tours, we highly recommend that you visit each of them to see for yourself. When you decide to make the trip, we have also created a self guided tour, in addition to the video tour to make this easier.

Greenwich does have more amenities like parks, shopping and golf courses if this is important to you. It also has better walkable areas like Old Greenwich and the downtown area that seem more fitting for our clients that want walkable areas. Although, I am sure Westport residents would argue that the waterfront shopping area is highly walkable, and they would be right. Compo Beach in Westport isn’t too shabby either.

Property Expectations:

Compared to Greenwich CT real estate, you should expect to get a noticeably larger home with better finish details in Westport for the same money, with the difference being more obvious as your price point increases. What most people don’t notice are that the lots are typically smaller and the housing stock is newer in Westport. If you are looking for a cul-de-sac, your odds of finding a suitable home are better in Westport because the design of the town’s road network leads to an abundance of dead end roads. 

For our clients who are considering expanding their search beyond Greenwich, Westport is the most common choice.


If you are thinking of moving to Connecticut's “Gold Coast”, I would like to work with you. If you aren't ready to call us yet, check out the rest of our website: and grab one of the many guides, maps and checklists that we have created for you. They will save you hundreds of hours of research, and help you make a better choice for you and your family.

I look forward to hearing from you!


Charlie Vinci

Lower Fairfield County 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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