Southport Village

Southport Village

Southport is a coastal village that stretches about two miles inland from Long Island Sound, and part of the larger town of Fairfield, Connecticut.  Walking the paved streets and pebbled lanes, one is immediately surrounded by the hamlet’s physical beauty and meticulous historic preservation, something so rarely found today in a pint-sized, urban environment.

Living in Town, Fairfield Connecticut

Living in Town, Fairfield Connecticut

There’s a reason so many people are drawn to the energy of downtown Fairfield and the ease of true in-town living. It offers a rare blend of charm, convenience, and classic coastal New England character—walkable living at its absolute best. Tree-lined streets connect timeless Colonials, charming Capes, and thoughtfully updated homes, all woven seamlessly into established neighborhoods.

Close to Schools and So Much More

Close to Schools and So Much More

There’s something quietly exceptional about life in Westport’s Long Lots neighborhood, especially when your home sits close to Bedford Middle School (grades 6 - 8) and Staples High School. It’s not just about convenience—though there’s plenty of that—it’s about being woven into the everyday rhythm of one of Westport’s most family-centered, connected, and livable communities.

Snow days are a rite of childhood in Connecticut

Snow days are a rite of childhood in Connecticut

Kids have forever loved the possibility of a snow day. Watching closings scroll across the tv screen, listening for announcements on the radio, calling the snow line and today, waiting for the email/text alert. Snow days—sheer days of childhood joy—are alive and well in Connecticut. 

Yes, e-learning and remote working are entirely feasible, but there is something so delightful about an unplanned day off. We all have work to do, things to learn and days to fulfill, but the Connecticut lifestyle allows, even encourages, you to take a break every now and again.

The Allure of Old Hill in Westport

The Allure of Old Hill in Westport

One of the greatest pleasures of living in Westport’s Old Hill neighborhood is the ability to stroll into the vibrant, ever-evolving downtown. Restaurants, boutiques, the Westport Library, Levitt Pavilion, several schools, and places of worship are all within easy reach. Just as important is the Saugatuck River, the waterway that connects Old Hill’s current community to Westport’s rich, onion farming and sea-faring past.

Westport Bank & Trust Building — Compass' New Home

Westport Bank & Trust Building — Compass' New Home

As realtors we understand the importance of location, are intrigued by history, appreciate fine craftsmanship and admire architectural design. As we look forward to our 2026 move across the river into the historic Westport Bank & Trust building, we are in awe of those that had the foresight to create, maintain and improve the building and the town of Westport.

October 2025 Newsletter

October 2025 Newsletter

We like to say real estate is about people, not just houses. Getting to know our clients and understanding their needs, wants and aspirations is truly the best part of our job. Can AI help match your ideals with a potential home? Certainly, but that's not where the magic happens.

AI and automation are here to stay, and we value the tools they provide (see the Compass Way section below). However, some things—human connection, trust, understanding—cannot be replaced by a machine. Let's meet for coffee and chat. Email, text or call to arrange a convenient time.

Preschools

Preschools

Due to rising wages and change in birthdate requirements for kindergarteners, preschool in CT has gotten more complex, costly and competitive. Prior to 2024-5 school year, children attaining the age of 5 by January 1st could begin kindergarten in the fall, as a 4 year old.

Now, many children with September-January birthdates attend a "5s" program at a preschool. This change created additional staffing, space and resource needs for preschools, adding to already rising costs.