Nestled along the picturesque Long Island Sound, Southport, Connecticut, is a charming coastal enclave that blends historic New England character with modern luxury. Known for its beautifully preserved 19th-century architecture, scenic harbor, and vibrant village center, Southport offers a unique mix of small-town charm and upscale living. Residents enjoy easy access to pristine beaches, top-rated schools, and a thriving arts and dining scene, all while being just a short train ride from New York City. Whether you're drawn to its waterfront beauty, rich history, or tight-knit community, Southport provides an idyllic setting for those seeking a refined yet relaxed lifestyle.
In recent years, Southport has emerged as a sought-after real estate market, and with the opening of BHS' new Southport office, we sat down with agents Annie Kruger, Andrew Whiteley, and Wendy Ryan to get their insights on this picturesque neighborhood.
What do you love most about Southport?
Annie Kruger: "Southport has such charm and pride. The shop owners are unique and community oriented, the homeowners speak proudly of their community, and together they support each other to make Southport a special enclave in Fairfield County. With events like the Turkey Trot at Thanksgiving, Santa’s arrival in December, Blessing of the Fleet in Spring, the annual book sale at Pequot Library, the community comes together all the time to create a community like no other."
Wendy Ryan: "Southport has been beautifully preserved with its 19th-century homes and businesses. You feel like you’re on a movie set driving through the village and down to the harbor. The scenery is truly unmatched."
Andrew Whiteley: "I believe Southport marks where New England begins and the bedroom communities of Manhattan end. It feels more relaxed and like a small country village."
What is your favorite local spot (dining, shopping, entertainment, etc.)?
Annie Kruger: "My husband and I love to sneak away whether it be during lunch or dinner to have a delicious meal at Martel's Restaurant. We often have mom’s night out at The Horseshoe. And my kids love Sammy’s Pizza. It’s hard to pick one!?"
Wendy Ryan: "So hard to choose, but I have to say the Fairfield Women's Exchange. I'm in there weekly for various gifts. It’s a non-for-profit shop run by volunteers, filled with everything you could ever need—children's clothes, antiques, jewelry, hostess gifts, etc. It's truly one of a kind."
Andrew Whiteley: "Nothing beats an afternoon walk through the Village along Harbor Road. It’s beautiful anytime of the year. You can enjoy the architecture, the gardens, the birds, the boats in the harbor…"
How would you describe the community vibe in Southport?
Annie Kruger: "Southport’s vibe is a coastal community filled with pride, togetherness and a flare for art whether it be beautiful offerings at Black Rock Galleries or the art you can see displayed in the yards of some homes in Southport. Nothing is cookie cutter here as the personality of the community shines through at every turn and with every residence.?"
Wendy Ryan: "The vibe is laid back. Many people have relocated here from New York City or various other cities and appreciate the slower pace."
Andrew Whiteley: "Relaxed. I always tell new arrivals that the Village affords you the opportunity to be as sociable or introverted as you care to be."
What's one hidden gem or little-known fact about Southport that more people should know?
Annie Kruger: "The Horseshoe Tavern and Cafe in Southport, known to the locals at “The Shoe” is truly the gem of Southport. Whether you are stopping in for a delicious burger, a cold beer or to catch a friend at Open Mic Night, it’s a guaranteed good time and a piece of Southport history. I’ve met up with other moms for a night out, gone there to toast a member of the community we have lost, snuck away on a low-key date night with my husband, and brought the kids for dinner on a night when cooking a meal wasn’t in the cards. It’s a crowd pleaser and you are sure to run into someone you know.?"
Wendy Ryan: "Southport was originally established as a critical shipping harbor in the late 1700s, specifically for the exporting of onions. Many of the larger homes were built by shipping magnates and included "widows walks" for owners to be able to watch their ships come and go."
Andrew Whiteley: "Willow Street in Southport owes its name to cuttings taken by local Sea Captains from a willow tree growing at Napoleon Bonaparte’s grave on Saint Helena Island."
What makes Southport a great place to buy a home?
Annie Kruger: "Southport is so rich in history. Being a homeowner gives you a chance to own your own little slice of history within the community and leave a mark for future generations. The values in Southport remain strong, the community prides itself in maintaining its personality and charm and the neighbors really look out for each other.?"
Wendy Ryan: "You get the best of both worlds. A small town, coastal community, yet close enough to NYC to hop on a train and experience the city for the day. It’s the ideal combination."
Andrew Whiteley: "Southport delivers the charm of Nantucket and the Hamptons—only it's a place you can truly call home, just an hour from Manhattan. Our real estate market is much more affordable compared to those summer resorts as well."
What advice would you give to someone considering moving to Southport?
Annie Kruger: "I would encourage you to come stay for the weekend and really dive into the culture. Enjoy a night at The Delmar hotel. Grab a coffee and a pastry at G Cafe Bakery (consider grabbing a loaf of their sourdough for later because it is divine!) and head on over to Southport Beach to enjoy the waves and sunshine. Grab a sandwich for lunch at Spic and Span and head to Southport Harbor to watch the boats come in and out. Meander through the village where you can admire the beautiful homes that are well cared for and each unique in their appearance. If you need a midafternoon pick me up, you can head to Organika for a delicious freshly made smoothie. Adventure to Martel's Restaurant for dinner and check out the evening scene at The Gray Goose. While it may be a small little slice of Fairfield County, it has so much to offer. And don’t forget to visit us in our office, right in the heart of Southport, so we can discuss the right house for you!?"
Wendy Ryan: "Don’t hesitate. All my clients who moved here wish they had done it sooner. And make sure to work with a local expert who knows the ins and outs!"
Andrew Whiteley: "Come and see it for yourself. For years, people moving out of NYC traditionally got as far as Westport and didn’t even know Southport existed. Our secret is out now!"
