Relevant Links:

This... is Westport Connecticut. We are going to explore the differences between the neighborhoods, so you can decide which area is a fit for you

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:

Westport Tour Overview:

This is a different kind of tour. We will take a look at the train stations and the beaches. We'll talk about home values in each neighborhood. We will explore the schools, shopping and the breathtaking waterfront. I’ll even throw in a few easter eggs along the way. 

If you are new to the website, blog or YouTube channel, my name is Charlie Vinci and I am a Westport CT realtor that helps people move here. If you are thinking about buying a home in lower Fairfield County feel free to sign up on our website or subscribe to our Youtube Channel as we are constantly creating new content for you!

In order to follow along, it will be helpful to have our Westport Neighborhood Map. To get the map, click here. Make sure to right click to save on your Mac/PC, or tap the image on your phone to save it.

Saugatuck Shores:

The island you see here is Cockenoe island. It’s open to the public so you can kayak or take a boat to its expansive sandy beach and calm bay. It’s a great place to unwind and feel like you are on vacation for the day. Let’s head to our first neighborhood which is identified as Saugatuck Shore on our neighborhood map.

The beaches you see here are exclusive to residents of the neighborhood associations or in some cases they are private beaches. This is a great location to launch your kayak from. As you can imagine, the views of the Long Island Sound and the neighboring islands just off shore are stunning. Most days, you can see all the way across the Sound to Long Island.

This neighborhood is divided into two parts, the area closer to the mainland is Saugatuck Shore, while the tip of the landmass is called Saugatuck Island.

This is a great location for boaters. Housing prices typically range from $790k to $3.2MM, with the most exclusive properties going for north of $4MM. As we head inland you will also notice the deep water lagoon. It’s well protected, and one of the best places for a private dock.

Next let's head over to the neighborhood of Saugatuck


Not to be confused with the Saugatuck Shore neighborhood that we just covered. Most of this neighborhood is located to the east of the Saugatuck river. Homes in the Saugatuck neighborhood typically range from $300k to $1.975MM, with the most exclusive homes selling for North of $4MM. 

This is an excellent location if you are looking for a waterfront home with easy access to the Westport train station. Taking the fast train will get you to Grand Central in about an hour. You can find more information on the train stations and parking permits in our Westport CT Buyer’s Guide.

Near the train station you will find many of Westport’s best restaurants. Some of my recommendations include: Tarantinos for Italian, Romanacci for their cannolis, Black Duck for their pub food, and Donut Crazy which is located on the northbound side of train tracks.

If you travel north up Riverside Ave from the train station, you will be treated with even more options. Nearly every restaurant in this area is top rated.

North of the station you will find Birchwood Country Club, it is a private 9 hole course that is considered to be one of the best in the country. It’s a par 36, with a rating of 37.3 and a slope of 131. 

To the north of the club you will find Saugatuck Elementary which is rated a 9 out of 10 by Right next door you will find Kings Highway Elementary. Which is also rated a 9 out of 10 by 

You can use our buyers guide to look up any address and find out what school your child will go to. I can tell you from personal experience that many of my clients move here primarily for the schools, although the low housing taxes and relatively short commute to Manhattan are also significant factors. 

If you are wondering how low the taxes are in Westport, I would suggest that you plan on $10k per year for each $1MM of purchase price. In other words, a $2MM home should be around $20k per year in property taxes.


Many consider this area to be the heart of Westport. This is the only place in Fairfield county where you will find a large quantity of high end waterfront shopping. Stores such as: Anthropologie, Patagonia, Tiffany, Peloton, William Sonoma and so many more.

There are many historic buildings in this area dating back to the early 1900s. As we wander down church lane you can see that the town is working hard to maintain the architectural integrity. This is a great place to grab a bite to eat and do some shopping, and should be on the top of your list when you come to visit Westport. 

Westport Library was built in 1986, but the origins of the Library association itself date back to 1886. It is considered one of the best public libraries in the country.

Just up the road from the Library and in-town shopping you will find the beloved Westport Country Playhouse. This non-profit organization produces thoughtful and creative works that are sure to impress anyone who loves theater. 

Many of my clients who love to live in a walkable environment choose to live in the in-town neighborhood. Homes here typically range from $476k to $1.8MM, with the most exclusive properties fetching northward of $3MM

Old Hill:

Across the bridge from the in-town neighborhood, you will find the neighborhood of Old Hill. The appeal of this area for many is the easy access to in town shopping, the Merritt parkway and Norwalk amenities, such as Stew Leonard’s, Whole Foods, Bed Bath & Beyond and many more.

Homes in the Old Hill neighborhood typically range from $785K to $3.275MM, with the most exclusive homes getting north of $4MM.

If you love wildlife and hiking with the family, check out Earthplace while you are in the area. This wildlife sanctuary is a blast for kids. It hosts a preschool, summer camp, and after school programs. Behind the building you will find many rescued birds. 

The area around Earthplace consists of sixty plus acres of hiking trails which are open to the public. If you are exploring the area, this is a great place to stop and let the kids blow off some steam.

Red Coat & Coleytown: 

As we head over to the neighborhoods of Red Coat and Coleytown, you will see the Merritt Parkway on the left side of the screen. In case you didn’t know, the Merritt Parkway turns into the Hutchinson Parkway in New York. These neighborhoods are mostly suburban with the exception of a few small commercial properties like the Westport astronomical observatory. The telescope is typically open to the public on clear Wednesday evenings

The appeal of this area for most buyers is a more rural feel. Homes in Coleytown and Redcoat neighborhoods typically range between $635k and $2.495MM with the most exclusive homes selling for north of $3MM.

In the area you will find Coleytown Elementary, which is currently rated 10 out of 10 by and right next door you will find Coleytown middle school which is currently rated 9 of 10 according to great Don’t forget to use the school lookup in our buyers guide to be sure which school your child will go to. 

Hunt Club:

Just south of Coleytown, you will find the neighborhood of Hunt Club. This neighborhood is home of the famed Staples high school that attracts so many families. Staples High has been consistently ranked amongst the best public high schools in the state. It’s currently rated a 10 of 10 by If you are like many of my clients who value easy school drop offs and pickups you may want to search for a home in this area. 

Right next door you will find Bedford Middle School. Which is currently rated a 9 out of 10 by If you choose a home that goes to both of these schools, along with long lots elementary or Greens Farms elementary, you will find that your school's pickups and drop offs take less time because of their close proximity. 

Homes in the Hunt Club neighborhood typically range from $800k to $2.945MM, with the most exclusive homes going for north of $3MM. If you are looking for a more rural, upscale feel, the east side of the neighborhood is a good fit.

Moving on! Just south of Hunt Club is the neighborhood of Long lots

Long Lots:

Some people may consider the neighborhood to go farther north than we have indicated on our neighborhood map, but we have chosen Long Lots road as the northern most border. 

Long Lots Elementary that I just mentioned is located in this neighborhood. It’s currently rated a 9 out of 10 on and as I mentioned before, it is in a great location to make picking up your kids from school a breeze. 

Adjacent to this school is the Boston Post Road. You will find that the Post Road is where much of the shopping is located outside of the in-town area I showed you earlier. The post road is also home to a number of great restaurants. If you get hungry while exploring the area and are looking for a sit down restaurant, I would recommend The Little Barn, for its interesting atmosphere and menu that will please just about anyone.

There are many other highly rated restaurants in the area too. If you are looking for a quick bite, I would recommend Ballduci’s fresh market, the prepared food section is excellent. 

Homes in the long Lots neighborhood tend to range between $700k and $2.5MM, with the most exclusive homes selling north of $3MM.

Alright, now we are going to head back towards the water.

Compo Beach:

You will see the Longshore Golf Course. It’s a public course, and is open exclusively to residents from Friday through Sunday. It's a men’s Par 69, With a rating of 68.3, and a slope of 121 from the blue tee, and women's par 73, with a rating of 72.7, and a slope of 123, from the white tee. Most locals consider it to be an excellent course. Other public amenities at Longshore include a pool, an ice rink in the winter, and tennis courts. 

This area tends to command a premium from buyers who prefer to live in a beach community, with home prices typically ranging from $565k to $5.125MM, with the most exclusive properties going for north of $6MM. Let’s take a look at some of the homes in the area...

Hall Island:

Technically part of the Compo Beach neighborhood, this is the beautiful Hall Island. Homes typically sell here from $2.3MM-$5.45MM, with the most exclusive homes selling north of $6MM. That is, if you are lucky enough to get one. Only about one home per year sells here. As you can see, Many of the homes have a beach, and if a dock is on your short list, the neighboring Compo beach yacht club may be a fit. Hall Island also offers some breathtaking views of Long Island Sound. If you are looking for a waterfront home my team and I are constantly searching for our clients, and we may have something for you that is not publicly available online. 

The V shaped beach next to Hall Island is Compo Beach, this beach is the one favored by most town residents. Public amenities at compo beach include a softball field, basketball courts and a skate park. The beach is open year round although there is a daily parking fee from May through September. It is a great place to get some sun, enjoy a book, and just spend some time with the family. 

Some of these homes along compo beach have recently sold between $2.4MM to $5.3MM

As we head up the coastline you will see Old Mill Beach. This is a great spot if you are looking for a smaller, quieter beach than Compo.

Mill Cove:

There is a footbridge connecting Old Mill Beach to the community of Mill Cove. As you can see here, it consists of a strip of beautiful waterfront homes. The lack of cars will make it feel as though you have been transported back to simpler times. Homes in Mill Cove tend to go for between $1.4MM and $6MM. Only three homes have been sold here in the last 10 years. 

To the right of Mill Cove you will find a 235 acre park with an expansive beach. Officially established in 1914, Sherwood Island is also known for being Connecticut's first state park. In addition to the beach, Sherwood Island has an oceanfront pavilion, trails and nature center that attracts people from across the state, to spend the day unwinding here. 

Greens Farms:

If you’re looking for a smaller community beach in the Greens Farms neighborhood you should check out Burying Hill Beach. The limited parking tends to keep crowds to a minimum. 

Just inland is the private prep school, Greens Farms Academy. This school is known not only as a great academic opportunity, but also for its fantastic athletic programs, which include Baseball, Basketball, Tennis, Wrestling, Soccer, and even sailing!

Just beyond Greens Farms Academy is the Greens Farms train station. This station is a great option if you plan to live in the neighborhood. The fast train will get you to Grand Central in about sixty-five minutes.

Some of my clients prefer homes which go to Greens Farms Elementary, as well as Bedford Middle and Staples High because it will reduce the running around that is required when dropping your children off and picking them up for after school programs. Greens Farms elementary is currently rated a 10 of 10 at  

Homes in the Greens Farms neighborhood typically range from $605k to $3.4MM. With the most exclusive properties fetching North of $5MM. Let's go take a look at Westport’s magnificent waterfront estates. 

While we are on the way there I will take the time to tell you that historically, the majority of $10MM plus sales in Westport have been along the waterfront area of Greens Farms, although there are other exclusive properties along the shoreline that are definitely worth looking at.

Should you need guidance in finding your next home, whether it's a waterfront estate or a great family home, call my office and  I will personally assist you. 

My oceanfront clients are always concerned with the view. As you gaze out the windows of these homes, you look over  expansive lawns, sometimes with a pool or sea wall, and in many cases there is a groomed sandy beach just before the completely unobstructed view across the long island sound.  As you look off in the distance, you will see sailboats making their way across your horizon, the smell of salt is in the air, and Long island is faintly visible on a clear day. You should expect to pay between $15MM and $25MM for the finest examples of real estate here. 


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


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.

Relevant Links