Fairfield… I never thought I would become one, but today, I proudly say I am a “Townie.” I feel very lucky to have grown-up in Fairfield and my husband and I feel beyond grateful to raise our girls in this exceptional town. It’s a place that blends beauty, history, foward-thinking and community and I am so fortunate to live, and sell real estate in the very neighborhoods that make this town so phenomenal.
What truly sets Fairfield apart for me are the people. I am blessed to have friends and neighbors with kind hearts, strong values, and a shared sense of community. That deep connection makes it easy to share my enthusiasm for Fairfield when I’m showing clients the stunning homes and picturesque hot spots that define this area.
Beauty is All Around
When introducing clients to Fairfield, I like to bring them to some of the most scenic and treasured spots:
- Southport Southport is where the glory of the waterfront is on full display. The charm of the Harbor, historic streets lined with pristine antiques, and breathtaking gardens make this area unlike any other. Small mom-and-pop shops, high-end dining (L’escale and Paci), as well as casual options (Gray Goose), markets (Spic and Span) and of course a local watering hole (the Horseshoe, known to fellow townies as “The Shoe”) plus cute boutiques add to the village’s appeal. Southport embodies Fairfield’s elegance and history, wrapped in a coastal atmosphere that’s impossible to resist.
- Greenfield Hill The Greenfield Hill neighborhood, centered around Greenfield Hill Congregational Church, is like stepping back in time. Many of the homes are beautifully preserved estates and turnkey antiques that homeowners proudly maintain. The iconic Dogwoods and massive Copper Beech trees are landmarks, especially in spring when everything is blooming. There is a calm, timeless beauty in this neighborhood with another quaint shopping center.
- Downtown and the Beach Area Fairfield’s downtown area is always bustling with energy. It’s a nice mix of boutique shops (La Moda, The Beehive, Snappy Gator, Marea, BoHo Prep) and national storefronts. The restaurants are delicious (Martel, Nordic Fish, Quatro Pazzi, The Chelsea, Bodega, and Mecha Noodle are just a few of my favorites). Pre-teens and teens love meeting downtown to shop (Olive My Stuff, Apricot Lane, and Caio Bella) followed by a trip to Starbucks, Saugatuck Sweets, or 16- Handles (sometimes going to all three). The Beach Area is just a short drive past town and I always have fun showing the gorgeous new construction and well-maintained older homes that are all walking distance to our fun public beaches. The area is elevated but always laid back.
Something For Everyone
Fairfield offers a fulfilling lifestyle, striking the perfect balance between small-town America and big city allure. With over 63,000 residents and a median age of 41, there is truly something for everyone. There are great town amenities, senior center, night life, 2 Universities, a movie theater, parks, multiple libraries, Farmer's and pop-up markets, small businesses and national brand headquarters.
- Go-to Spots: I love the cute markets and boutiques where the owners and employees know you by name. Spic and Span Market, The Pantry, La Moda, Henry C. Reid Jewelers, BeeHive, Boho Prep and Outdoor & Design are just a few of my favorites.
- Community Spirit: Fairfield’s philanthropic heart shines through charity events like the Near & Far Aid Designer House Tour, Southport Garden Stroll, and the Turkey Trot. Adults, teens, and children unite to volunteer, participate, and inspire.
- Entrepreneurial Energy: Fairfield nurtures local businesses and startups from creative ventures like Floraco clean products and Haute Energy jewelry to printing shops like andHowGraphics. I love supporting and learning about my fellow residents’ diverse backgrounds and passions.
- Access & Proximity: Fairfield has three train stations. When you feel like a change of scenery, you’re an easy ride away to Manhattan or New Haven. With five public beaches - each with its own personality, lakes and countless nature trails (Mill River, Lake Mohegan, Audubon), Fairfield offers endless opportunities to unwind in nature. A spontaneous visit to Southport Beach is one of my favorite ways to pause, reflect, and re-energize and floating down Pine Creek is the most fun (IYKYK)!
Feels Like Home
From the scenic drives down Pequot Avenue and Sasco Hill Road to the meandering rivers, storybook meadows and open space, Fairfield offers beauty in every corner. Late Spring and mid Fall are my favorite times of year here. Spring brings excitement, warmer temps, gorgeous blooms (the busy real estate season!), happy neighbors out walking and biking. Fall brings the crisp air, the beauty of the changing leaves and the most vibrant sunset skies over Long Island Sound. It’s magical here. It’s a place that feels alive with promise.
My enthusiasm for Fairfield continues to grow as our town evolves and improves. With its boundless potential and community devotion, I am confident that Fairfield's best days are still ahead. I am proud to be a part of this town and will always share its unique and fabulous features with anyone interested in exploring it. Fairfield is not just my home; it’s where my heart is.
Specializing in the marketing, sale, and rental of unique and luxury properties in Fairfield County, Jaclyn is a top-producing Realtor with over 22 years of record-breaking success and a steadfast commitment to exceeding client expectations. Contact: 203-981-5012 and follow on Instagram @jaclyn_picarillo_realtor06880 Higgins Group | Forbes Global Properties | 30 Elm Street Westport, CT 06880 | Licensed in CT
I am proud to be a part of this town and will always share its unique and fabulous features with anyone interested in exploring it.