Beautiful waterfront homes and estates on large verdant lots, private beaches and docks in Southport, Fairfield, CT

Southport Neighborhood - Fairfield, CT

Historic charm, great schools, sailing tradition

Homes for Sale

10 active homes for sale

About

Historic charm, great schools, sailing tradition
Beautiful village, amazing waterfront

Nestled along the picturesque Connecticut coastline, Southport stands as one of Fairfield's most venerable neighborhoods, exuding an enduring historic charm and an air of aristocratic elegance. 

Its deep-rooted sailing tradition harks back to the mid-1800s when it thrived as a prestigious coastal port; a legacy that continues to infuse daily life, notably celebrated each June with the beloved Blessing of the Fleet and Southport Street Parade, drawing visitors from across the region. 

The heart of the neighborhood, a designated historic district, showcases a stunning collection of over 150 homes, their Greek Revival, Romanesque, and Federal architectural styles whispering tales of Southport's prosperous past.

Today, Southport retains its status as an affluent enclave for a multitude of compelling reasons. Magnificent waterfront estates, many boasting private beaches, line the shore, complemented by the neighborhood's pervasive historic allure and abundant green spaces that frame the stately residences. 

Residents enjoy access to a beautiful public beach and benefit from a distinguished sailing community and highly acclaimed schools, all contributing to Southport's reputation as one of the most desirable places to live along the esteemed Gold Coast.

The Homes

Steeped in historic charm and radiating a classical New England vibe, the residences of Southport offer a captivating glimpse into architectural elegance. While many of the grand estates, particularly those gracing the waterfront, draw inspiration from the romanticism of the Victorian era, the prevailing style for homes on the market is the timeless Colonial. This iconic design is complemented by a selection of charming Cape Cod houses and a few meticulously renovated Antique homes, each contributing to the neighborhood's distinctive character. For those seeking a different living experience, Southport also presents several condominium options, featuring both ranch-style units and thoughtfully designed townhouses.

The waterfront properties in Southport are truly exceptional, representing the pinnacle of coastal living. These amazing estates and houses frequently boast luxurious amenities designed to maximize their prime location. It's common to find properties equipped with in-ground pools for leisurely afternoons, private docks providing direct access to the water, and, in some instances, the ultimate indulgence of small private beaches, offering an unparalleled connection to the serene shoreline. This blend of historic architectural styles and impressive waterfront features solidifies Southport's reputation for distinguished homes.

Southport Lifestyle

Life in Southport offers a captivating blend of serene coastal living and engaging activity. Residents embrace a relaxed pace, often drawn to the water for sailing and various watersports, a lifestyle deeply ingrained in the community's fabric. The picturesque Southport Town Harbor, a short stroll from the village center, provides stunning vistas of the Country Club of Fairfield and the distinguished Pequot Yacht Club.

Sailing and boating are more than hobbies; they are a way of life, with the renowned private Pequot Yacht Club impressively fostering the next generation by hosting local high school sailing teams and offering world-class youth sailing instruction accessible to all, alongside the public Community Sailing of Fairfield which provides further instruction and racing opportunities. 

Amazing views, sailing adventures, community events!

Beyond the harbor, Southport unfolds with a wealth of cherished destinations and traditions. The annual Blessing of the Fleet and Southport Street Parade in June is a highlight, a vibrant event where fife-and-drum corps and the Governor’s Horse Guard lead a procession to the harbor for a ceremonial blessing of the boats. For leisurely days, Southport Beach offers a perfect seaside escape, while Ye Yacht Club provides a public boat launch, picnic spots, and kayak storage in a scenic park setting. Intellectual curiosity is well-served at the historic Pequot Library, renowned for its special collections and one of Connecticut's largest summer book sales, complemented by the neighborhood's inviting array of restaurants, fine dining, antique shops, and specialty stores.


Recently Sold Homes

71 homes sold / past 12 months

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