Choosing the right town is one of the biggest decisions you’ll make when buying a home — especially if you’re a first-time buyer. Before you even start touring properties, you’re probably wondering which towns offer the best schools, what your commute might look like, and where you can get the most value for your budget. To help make things easier, I put together a breakdown of four popular shoreline towns that buyers often consider: Old Saybrook, Westbrook, Clinton, and Essex. Each town has its own personality, price point, and community feel, and depending on what you’re looking for, one may stand out as the perfect fit.
School ratings in each town
If you’re planning for the future or already raising a family, school quality is usually one of the first things you look at. Below is a simple overview of the public school ratings (using Zillow/GreatSchools-style scores) for each town and how they compare.
Old Saybrook
Kathleen E. Goodwin School (PK–4): 5/10
Old Saybrook Middle School (5–8): 7/10
Old Saybrook Senior High School (9–12): 8/10
Westbrook
Daisy Ingraham School (PK–4): 7/10
Westbrook Middle School (5–8): 8/10
Westbrook High School (9–12): 7/10
Clinton
Lewin G. Joel Jr. School (PK–4): 7/10
Jared Eliot School (5–8): 7/10
The Morgan School (9–12): 7/10
Essex
Essex Elementary School (PK–6): 6/10
John Winthrop Middle School (6–8): 3/10
Valley Regional High School (9–12): 7/10
Overall, Old Saybrook and Westbrook tend to come in a little stronger at the middle and high school levels. Clinton is pretty steady across the board with solid 7/10 ratings for all grades. Essex is still a really desirable town, but its school ratings are a bit more mixed, especially when you get to the middle school.
Commute convenience
When you’re comparing towns in this area, commuting is actually one of the easier decisions. All four towns sit close together along the Lower Connecticut River Valley, and you can drive from one town into the next in ten to fifteen minutes. That makes it convenient if you work nearby or want access to amenities in the surrounding towns.
For longer commutes, Amtrak stations are located in or near each of these towns, giving you direct or easy access to major cities like New York City and Boston. Whether you’re traveling for work or heading into the city for the weekend, commuting is straightforward no matter which of these towns you choose.
Affordability and median home prices
Home prices vary depending on the town, but here’s a quick look at the 2025 median sales prices and how they’ve changed since 2024. This helps give you a sense of affordability and market trends in each area.
Old Saybrook
2025 median: $737,500 (up from $700,000 in 2024)
Westbrook
2025 median: $755,500 (up from $650,000 in 2024)
Clinton
2025 median: $485,000 (down from $505,000 in 2024)
Essex
2025 median: $732,500 (up from $700,000 in 2024)
If affordability is your main priority, Clinton clearly stands out. It offers the most approachable price point of the four towns, with a slight price decrease year-over-year. Old Saybrook and Essex remain similar in price, while Westbrook has seen one of the biggest jumps. Part of that comes from increased demand for shoreline living over the past few years, which is something many first-time buyers are feeling across Connecticut.
Mill rates and yearly property taxes
Mill rates directly affect your annual property taxes, so they’re an important part of your budget. Here’s how the towns compare:
Old Saybrook: 15.2
Westbrook: 21.7
Clinton: 30.26
Essex: 18.05
Old Saybrook has the lowest mill rate on this list, which can make a meaningful difference in your long-term affordability. Clinton’s is the highest, though its lower home prices often help balance things out for buyers.
What each town offers
Beyond numbers and ratings, lifestyle is just as important. Each of these towns has its own character, and depending on what you’re looking for, one may feel more like home than the others.
Old Saybrook
If you want a lively but comfortable shoreline town, Old Saybrook is a top choice. The downtown area is one of the best in the region — walkable, full of boutique shops, and plenty of restaurants. Local favorites include The Monkey Farm, Aspen, and The Rabbit Hole. The town offers both public and private beaches, seasonal parades, street celebrations, farmers markets, and all the essential shopping you need, including grocery stores and Walmart. Old Saybrook also has a transfer station, which means curbside trash pickup isn’t required. The only downside is that activities for children are somewhat limited compared to larger towns, but the community feel is strong.
Westbrook
Westbrook offers both public and private beaches, making it a great option for anyone who loves shoreline living. While it doesn’t have as much shopping as the surrounding towns, everything you need is only a short drive away. The town uses a transfer station for recyclables and larger items like mattresses or wood, though residents do have required curbside trash pickup. A standout perk is the movie theater right in town — something you won’t find in the other nearby communities. And when it comes to food, two local favorites are close by: Cafe Routier, known as one of the best fine dining options in the area, and Turtle Cafe, a go-to spot for a great breakfast.
Clinton
Clinton gives you the best shopping options of all four towns. There are several grocery stores, a downtown area that’s a bit more spread out, and the biggest draw — the Clinton Premium Outlets, with more than 70 name-brand and designer retailers. Like the others, Clinton offers both public and private beaches. One local favorite is Lobster Landing — a hidden shoreline gem known for serving one of the best lobster rolls in New England. The town also has a transfer station, though residents do need to purchase dump passes if they want to use it.
Essex
Essex is arguably the closest match to Old Saybrook in terms of charm. Its downtown is highly desirable, walkable, and filled with shops and restaurants — just on a slightly smaller scale than Old Saybrook. If you’re looking for a top-notch sandwich, Bun on the Run has one of the best around, and if you’re craving Mexican food, Sayulitas is always my go-to. Essex is especially festive during the holidays and hosts several parades and community events throughout the year. Unlike the other towns on this list, Essex is a riverfront community, so there are no public beaches in town — but you can buy day passes for nearby shoreline beaches if that’s important to you. The town is made up of three distinct villages — Essex Village, Centerbrook, and Ivoryton — each offering its own unique vibe.
Choosing the right town comes down to what matters most to you. If walkability and community events are important, Old Saybrook or Essex may be the best fit. If you want the most affordable option without sacrificing shoreline access, Clinton is worth a closer look. And if you’re searching for a quieter beach town with solid schools, Westbrook might be exactly what you’re hoping for.
Whichever town you’re drawn to, exploring these communities in person is the best way to get a feel for what fits your lifestyle. When you’re ready to start touring, I’m here to help you compare your options and find the place that feels right for you.
Your Expert Guide to Life Along the Connecticut Shoreline 
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