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Southport is a coastal enclave in Fairfield and has an identity all its own. It is one of the more affluent and desirable neighborhoods in Fairfield. Located along a beautiful stretch of Long Island Sound coastline and bordering Westport in the southwest part of town, Southport boasts a rich New England history that spans time since its settlement in 1639. Designated a local historic district, the neighborhood is protected by strict zoning laws designed to preserve its history for future generations. Southport homes, especially in the coastline area, display period architectural styles from the 18th and 19th century, including grand Federal and Greek Revival.

The seaport area, with its breath-taking views, is home to the private Pequot Yacht Club which offers a wide array of sailing programs. There is also access to Ye Yacht Yard a public marina on Harbor Road that accommodates 65 small boats, provides boat launch services to residents and access to moorings. Additionally, 20 kayak racks are available. Southport also has its own beach, two churches, boutique shops and antique stores, restaurants, and The Delmar Hotel – a luxury boutique hotel. The privately run Pequot Library hosts concerts and lectures throughout the year including the Southport garden stroll and summer book sale, one of the largest book sales in New England. Southport Congregational Church annual fundraiser “Rooms with a View” celebrates art and architecture raising money for the church, its missions, and charities within the greater Bridgeport area. Trinity Episcopal Church is also located in Southport.

Southport is home to the private Southport School, providing transformative educational experiences for students in kindergarten through 8th grade with language-based learning differences, such as dyslexia and ADHD/ADD. In addition, Southport is home to Mill Hill Elementary School. Some neighborhood areas in Southport that are outside the census tract attend Timothy Dwight Elementary School in Greenfield Hill. Both Mill Hill and Timothy Dwight primary schools feed into Roger Ludlowe Middle School and Tomlinson Middle School — both of which feed into Fairfield Ludlowe High School.

Smaller homes on streets closest to Interstate 95, which cuts through the heart of Southport, are attracting younger buyers. In addition to providing easy access to the interstate, Southport has its own train stop on Metro North railroad that offers one of the most convenient commutes into NYC.

With incredible views of Long Island Sound, historic architecture, charming town center, and a serene harbor area, Southport is one of the most sought-after neighborhoods in Fairfield.

Go to my Fairfield page to view other neighborhoods in Fairfield.
Neighborhoods in Fairfield

Southport Links:
The Pequot Yacht Club
Ye Yacht Yard
Pequot Library
Southport Congregational Church
Rooms with a View
Trinity Episcopal Church
The Southport School



Location, Location, Location!  Renovated Southport Beauty!  Walk to Southport Village, Train, Harbor, & Beach.  Tucked away behind Pequot Library this 3 bedroom, 2 1/2 bath classic colonial is situated on a flat quarter acre on a tree lined cul-de-sac.  Smashing kitchen renovation boasts Chef's kitchen and custom cabinetry by Christopoulos Designs.  A New Laundry and Mudroom were added off garage, along with a stunning half bath.  The Foyer opens up to a charming family room with a wood burning fireplace, and adjoining room that could be used as a possible 4th bedroom, office, or playroom.  The first floor Master Bedroom, currently used as a family room, has vaulted ceilings and another stunning bathroom renovation! Upstairs you be greeted by a spacious landing, 2 large bedrooms with generous closets and yet another renovated full bath ! The lower level offers ample storage space and other possibilities.  The backyard situated conveniently off the kitchen, is private and ready for family entertaining!  Renovations completed by local esteemed builder, Kaesmann Builders.  Nothing to do except unpack your bags and enjoy all that Southport has to offer! Schedule your tour today! Architectural plans available upon request For proposed additional bedroom.  
Refrigerator in Lower level is not included in sale. $699,000 Show

74 Westford Drive Fairfield, Connecticut

3 Beds 3 Baths 2,009 SqFt 0.250 Acres

Southport Classic in  "The Village". Charming Walk-to-Village Walk-to-Train Vintage home featuring Spacious and Bright Living Room, Formal Dining Room with built-ins and decorative fireplace, Kitchen with Granite counter-tops, Cherry Cabinets and SS Appliances. Oversized and Vaulted Family room with raise hearth fieldstone fireplace and additional Den/Office. Laundry and Powder Room off of Kitchen.
Sunny and Bright MBR on 2nd floor and two additional Bedrooms and full bath.  
Door from kitchen to back porch and lower flagstone patio. 
Lots of additional space in basement for storage, and overflow. Walkout to back yard.
Walk to all local amenities: Train Station, Harbor, Village, Post Road and shops. Easy access to Rt. 95. EASY TO SHOW!!!

411 Westway Road Fairfield, Connecticut

3 Beds 2 Baths 3,126 SqFt 0.330 Acres

It's the opportunity you've been waiting for! Updated and move in ready, this classic colonial is perfectly located in Southport/Fairfield and will not last! A beautiful new outdoor patio and flat lot offers a fun yard for outdoor entertainment. The large rooms boast high ceilings, updated windows and hardwood floors throughout. The kitchen offers a center island with great flow from the dining room to the living room. The family room, which could easily be converted to a first floor master or guest wing with a full bath, has vaulted ceilings and easy access to the back patio. This space is flexible enough to be an office or workout room as well! The finished lower level offers approximately 250 sq. ft. of additional living space and is bright, clean and offers a great area for all ages. From restaurants, shops, beaches, trains, and more, this location is conveniently located in the heart of Southport/Fairfield. Don't let this opportunity pass! $474,000 Show

217 Bronson Road Fairfield, Connecticut

3 Beds 2 Baths 1,632 SqFt 0.260 Acres

Affordable Southport Waterfront minutes from train and shopping. Enjoy the best of both worlds: A nature lover's retreat, perched above the river's edge at the rear of a 1/3 acre parcel -- yet close to most everything! Across the river sits Mill Hollow Park, a nine-acre "forever" nature preserve with walking trails. Birdwatch and fish from your deck or enjoy all of historic Mill River by canoe/kayak. Afterward, enjoy Fairfield's many near-by amenities and attractions (Long Island Sound, beaches, harbors, marina, parks, library, shopping and restaurants, etc.) OR easily catch a train to Manhattan from one of two nearby train stations. The house itself is a two and one half story home with three bedrooms and two full baths. The bedroom areas (which includes a 25'x14' MBR with cathedral ceiling, skylights and a full bath with W/D), total 1177SF and the common/community area downstairs (LR/DR/Kitchen) another 700+/- square feet. In addition, there is a one bay garage with loft, storage/wine cellar, both a patio and deck (and steps leading to the water’s edge). If you are looking for the best location for the money, welcome home. This setting, relationship to nature, is unique and cannot be duplicated. Also being sold as land/new construction. $449,000 Show

680 Bronson Road Fairfield, Connecticut

3 Beds 2 Baths 1,877 SqFt 0.300 Acres