Westport, CT Real Estate
Just 50 miles northeast of New York City, Westport, Connecticut offers a rare blend of coastal elegance, New England charm, and modern luxury. With a history dating back to 1693, when it was first settled by the “Bankside Farmers” in present-day Greens Farms, Westport has long been a cultural and residential haven for artists, writers, and professionals seeking both tranquility and inspiration.
Real Estate Snapshot
The Westport real estate market is known for its variety and prestige—from waterfront estates to modern townhomes and low-maintenance condos. Buyers will find everything from classic Colonials to custom-designed luxury properties.
You can browse all homes currently for sale in Westport, or refine your search by category, whether you're interested in luxury listings, condominiums, townhomes, multi-family options, or commercial real estate.
Downtown and Local Culture
Westport’s walkable downtown is a vibrant hub lined with boutique and designer retailers, chef-owned restaurants, independent bookstores, and local art galleries. Residents also enjoy the recently updated Westport Library, a dynamic community space with award-winning architecture.
The town celebrates its creative roots through cultural landmarks like MoCA Westport, the Westport Country Playhouse, and the Levitt Pavilion, which hosts over 50 free concerts each summer.
Beaches, Recreation, and Nature
Westport is home to four beaches, including the ever-popular Compo Beach with its boardwalk, playgrounds, and sports courts. Outdoor recreation is a cornerstone of life here, thanks to Longshore Club Park, which offers golf, tennis, sailing, and a pool, all with stunning views of the Long Island Sound.
Schools and Commuting
Families are drawn to Westport for its nationally ranked public school system, highlighted by Staples High School, known for excellence in academics, arts, and athletics.
For those commuting to New York, Westport offers two Metro-North train stations—Saugatuck and Greens Farms—making it a practical and peaceful home base just over an hour from Grand Central Terminal.
Communities
What to Love
- Highly Acclaimed Schools
- Robust support of the arts
- Thriving downtown
- Top rated restaurants
- Several performance venues
- Many festivals and events
Living in Westport, CT
Out of all the cities and towns in Connecticut, Westport is perhaps home to the most creative and artistic residents in the entire state. It's teeming with an incredible background full of storytelling and the performing arts.
It is no wonder there are multiple playhouses and performance venues in the area. Not only that, Westport truly values its residents and their input on how to improve the town. When people move to Westport, it is often for life.
A large segment of the population are retirees and empty nesters who have lived here for years with no incentive to move anywhere else. It's also the perfect place for families, especially with burgeoning young artists in their midst.
Dining, Entertainment & Shopping
James Beard-Best Chefs In America nominee Bill Taibe is one of the most notable talents in Fairfield County and is considered a pioneer of the culinary arts, particularly within the community. The owner of The Whelk, Kawa Ni, and Don Memo, his restaurants are among the most sought-after for nightly reservations.
Breathtaking waterfront views, exquisite seafood dishes, and cocktails are all reasons to visit The Pearl Restaurant and Bar at Longshore Park. Locals love going to The Pearl for superb American cuisine. It is an excellent meeting spot to catch up with friends or conduct business lunches.
During the warmer months, or when you have a sweet tooth, Saugatuck Sweets is the best place for coffee, ice cream, fro-yo, shakes, and buying candy in bulk. They also sell special kits to let you make ice cream sandwiches and more, right from the comfort of your own home. This sweet retreat is also a great place to buy birthday cakes.
For upscale shopping, Mitchells is a beloved family-owned boutique known for their concierge level of personalized services. Here, you will find countless designer labels and luxury items that are perfect for any occasion. From Aquazzura, Brunello Cucinelli and Celine to Valentino, Veronica Beard and Zegna, Mitchells is the ultimate hotspot for men and women looking to freshen up their wardrobes.
If you are planning a whole day to shop then Bedford Square is where you will want to head. Locals love its charming architecture and variety of shops. Centrally located within the square are Williams & Sonoma, Anthropologie, Barbour, and Lillian August. Around the corner you will find Serena & Lily, Bungalow Decor and Kerri Rosenthal. Grab lunch or dinner at Spotted Horse Tavern once you are done shopping! For a more comprehensive look at our merchants, check out the Westport Downtown Merchants Association list.
There is no better time to shop-til-you-drop than during the annual Sidewalk Sale! Savvy shoppers can find incredible sales on Post Road, Main Street, and the surrounding areas. Most stores participate in the event, offering unbelievable bargains right on the sidewalk to make it easier for people to find.
Fun Things to Do in Westport
If you are looking for outdoor recreational spots in Westport, Compo Beach is a sprawling, 29-acre beachside park along the Long Island Sound. Near a concession stand, volleyball courts, a playground, and other activities, there is plenty to do for both adults and kids.
The same can be said for Longshore Park, which is home to one of the most prestigious municipal golf courses in Fairfield County, Longshore Ice Rink and The Longshore Sailing School. There is also the Westport Weston Family YMCA for swimming, aerobics, exercising at the gym, and more.
Performing arts are best attended at the Levitt Pavilion, an anchor for the vibrant downtown scene in Westport. You can also support the arts by visiting the Westport Country Playhouse, a not-for-profit theater that has been around since the 1930s. Many notable actors have performed at the playhouse over the years, including Paul Newman, James Earl Jones, Jessica Tandy, Olivia de Havilland, Jane Fonda, and more.
Of course, beyond places to visit, there are exciting annual festivals and events hosted in Westport and the surrounding county. The Blue & Views Festival has been a yearly tradition since 2008 and is typically held during Labor Day weekend. The festival is all about celebrating soulful musicians along the Saugatuck River with an incredible street party and delicious barbecue.
Supper & Soul is another live dinner and concert series event hosted by The Westport Library. In fact, the library hosts a number of events for adults, teens, and kids. They sponsor reading challenges, camps, lectures, and the beloved two-day StoryFest that celebrates literature in a fun and festival setting.
Westport School District
- Staples High School
- Coleytown and Bedford Middle Schools
- Kings Highway, Coleytown, Long Lots, Greens Farms and Saugatuck Elementary Schools
- Greens Farms Academy
- Pierrepont
