Fairfield and Westport CT Real Estate Guide

Local insights on buying, selling, and living in Fairfield County

Martel

Fairfield’s Super Seven for Supper 2024

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Hands down, one of the most fabulous features of Fairfield is the wide selection of chic eateries downtown. So, I thought I would share seven of my favorite picks for dining and ambiance.
 
The Chelsea is a funky and somewhat rustic place to have a drink and enjoy a meal.  Rough wood accent walls and ornate wrought iron design elements are contrasted with neon green metal chairs. The cozy bar hosting stylish guests (the women always seem to wear great shoes, just saying) pulls it all together! Mark says that no one else in town can beat the Chelsea Burger.  I personally cannot live without their octopus appetizer, a dish they tend to vary from time to time.  It doesn’t look huge when it arrives, but there is so much protein in it, you are sure to be full when you finish. The flavors in my favorite version are spectacular! Large tentacles come with potatoes, greens, onions, and a pickled vegetable that adds a perfect punch!  It’s a must-have in my book, with all the goodness and none of the guilt. Their Cobb Salad is fantastic too
 
Gabagool Wine BarOne local favorite where regulars are made to feel like family is Gabagool. The owner, Antonio and his team always greet you with a warm welcome and seem genuinely thrilled you have arrived. The ambience is stylish, glamorous, cozy with plush chairs to relax in, and funny. Poking fun on the Soprano’s TV series, the restaurant is complete with The Family portrait and a mugshot backdrop where you can get an instant photo of your own! The covered patio is fully heated and decorated for service most of the year. The eatery offers gregarious people and fun food with a flare, featuring “bawls” of all flavors on their appetizer menu, a fabulous antipasto, and their signature Gabagool Pizza with spicy oil! The Crispy Calamari Salad is the best I’ve had anywhere, and for the must-have drink with cucumber tequila, ask about “Howyoudoin”!
 
Old Post Tavern
 
For your classic tavern feel, visit the Old Post Tavern right on the corner of the Post Road and Unquowa.  They have been known to have a fun band during happy hour, and the patio is lovely during the warm season.  If you are a fan of French Onion Soup, look no further. Something about their blend of cheeses as well as some magic ingredients in the broth makes theirs unbeatable!
 
 
BodegaIf it’s gourmet Mexican food in a festive atmosphere you’re after, Bodega is the place to go. There’s a location in Fairfield and Darien. Since it’s another tiny place, you may have to sample their top notch margaritas or other specialty drinks while you wait for your table or seat at the bar.  One of Bodega’s delectables is the Ceviche, a deceivingly filling dish posing as an appetizer. The fish, in a specialty cocktail sauce, has a fantastic flavor and comes with some toasted plantains, that in my opinion, make a complete meal.  If you prefer something hot, their Chicken Soup is hearty and delicious.  You can have it mild or spicy depending on whether you opt to dump in the hot peppers served on the giant turquoise spoon.  Burrito Tinga is Mark’s tasty favorite, and my daughter loves the Gombos Tacos. Bodega's Festive Atmosphere
 
Martel is on the Post Road in Southport and is a cozy place with a bit of a steakhouse feel. The ceilings are high, yet ornate, and there is always an art gallery Marteladorning the walls. Always bustling, the place serves a warm, upbeat atmosphere.  Although there are many excellent dishes here, my husband and I have gravitated toward sharing the Fondue for Two followed by Martel’s House Salad. The salad features marinated tomatoes and an aged Danish Blue Cheese that are fabulous together. If the fondue is off-menu for the summer, an equally rich and yummy alternative is the side order of creamed spinach!  I have it as a meal, with wine, of course.
 
Last, but not least, we love the Grey Goose, also in Southport, where we once stood elbow to elbow with John Mayer before being seated. The atmosphere can be described as rustic and cozy with an eclectic crowd. Some folks go to hang out, others go for dinner. There’s always a flat screen at the bar featuring a sporting event as well as a crackling fireplace on the opposite wall. Penne ala Vodka, Grey Goose Style is Mark’s staple, while I go back and forth between the Grey GooseLobster Macaroni and the Steak Tips small plate.  The Lobster Macaroni is the absolute best here, with the secret ingredient of truffle oil to enhance the generous chunks of lobster and the crispy cheese topping. The Steak Tips are equally fantastic. Cooked to perfection, they come with a corn salsa and chipotle mayo dip that together, absolutely melt in your mouth!
 
The Sinclair commands space and attention downtown in the Brick Walk. The patio is great during the summer, surrounded by thick trees and protected by a multi-settings awning. The Mussels in a Pot Thai Style (5 additional styles to try!) are delicious, and Mark gave two thumbs up to the Steak Sandwich.  Sometimes on a Thursday night, you can dance and sing along to the live music of the fabulous Tangled Vine!

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All this talk is making me hungry!  Be sure to try out Fairfield’s fabulous eateries. Thinking of moving to the Fairfield and Westport area?

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Author: Luxury Coastal CT Real Estate Specialist Linda Raymond at William Raveis Southport

Luxury Coastal Real Estate Specialist | Fairfield Beach, Southport & Westport CT | Waterfront & Lifestyle Transitions | William Raveis Real Estate Buying or selling a home can feel overwhelming, or exciting. It is one of life’s biggest transitions — and it often comes with more questions than answers. How do I price my home for top dollar? What upgrades matter most to buyers? How can I compete for Fairfield Beach or Westport CT homes for sale without overpaying? I’m Linda Raymond, a Fairfield County Realtor with William Raveis, and I'm here to guide you to make informed decisions so your move is smooth, strategic, and successful! As a lifelong Connecticut resident who has lived and worked in Westport, Fairfield, Southport, and neighboring towns, I bring deep local knowledge and community connections. My clients trust me for personalized service, innovative marketing, and results-driven strategies that help sellers achieve the best price and buyers find the right fit — whether that’s a luxury home in the Fairfield Beach Area or Westport or a first home in a welcoming neighborhood. With nearly 100 five-star reviews and recognition as a Luxury Property Specialist, Chairman’s Elite Club member, and Connecticut Magazine’s Five-Star Professional Award winner, my track record speaks for itself. But what I value most are the long-term relationships I’ve built. Many of my clients return — or refer friends and family — because they know I’ll put their goals first. Whether you’re upsizing, downsizing, or relocating to Fairfield County, I’ll start by listening closely to your needs and priorities. Then, I’ll create a custom plan to help you move forward with confidence. Let’s make your next move rewarding — and even exciting. Call or text me today at 203.912.4440 to connect with a trusted Fairfield and Westport CT Realtor.