Southport Homes for Sale

Welcome to Southport, a picturesque coastal gem nestled within Fairfield, Connecticut. Known for its charming New England aesthetic and vibrant community, Southport offers a serene escape while being conveniently close to urban amenities. This quaint neighborhood is characterized by its historic homes, tree-lined streets, and stunning waterfront views, making it a perfect place for families, professionals, and retirees alike.

One of Southport's most enchanting features is its rich history, evident in the beautifully preserved architecture that dates back to the 18th century. Stroll along the scenic streets and you’ll discover an array of delightful boutiques, artisanal shops, and cozy cafes. The Southport Harbor, with its sailboats and yachts, provides a picturesque backdrop for leisurely walks and outdoor activities. Residents enjoy access to pristine beaches, parks, and walking trails, perfect for soaking up the natural beauty of the area.

For those considering making Southport their home, you're in luck! The real estate market in this charming neighborhood offers a diverse selection of homes for sale. From elegant colonial-style houses to modern waterfront properties, there’s a perfect fit for every lifestyle. Whether you’re looking for a cozy single-family home or a luxurious estate with breathtaking views, Southport’s real estate options cater to various tastes and preferences.

With its idyllic setting, strong sense of community, and access to top-notch schools, Southport truly embodies the essence of Connecticut coastal living. Explore the homes for sale in this enchanting neighborhood and discover your dream home in Southport today!

Newest Southport Homes for Sale

$2,695,000

5 Beds ⋅ 5 Baths ⋅ 24201702 MLS

Discover exceptional waterfront living at 400 Bronson Road, a recently enhanced custom colonial overlooking scenic Mill River in sought-after Southport. Offering 4-5 bedrooms, 4.5 baths, and 5500+ square feet across four levels, this sophisticated residence seamlessly blends timeless design, modern luxury, and exceptional functionality. A newly finished 1,000-square-foot lower level adds extraordinary living space with a stylish family room, recreation/gym area, stone gas fireplace, remodeled bath, full workshop, abundant storage, and new HVAC. Brand-new sliders fill the space with natural light. A whole-house generator provides complete utility coverage. The home is elevated by a custom pantry and mudroom, double ovens, upgraded kitchen fixtures, built-in window seats, custom media room, imported Italian wallcoverings, designer lighting, and bespoke built-ins. The luxurious primary suite features a spectacular custom walk-in closet and spa-like en-suite bath. Outside, fully fenced front and rear yards, a new stone wall, flagstone walkway, and custom back-porch built-ins create an exceptional setting for entertaining and enjoying river views. Just minutes from Southport's beaches, golf, shops, and restaurants, this remarkable waterfront property offers an unparalleled combination of sophistication, wellness, privacy, and lifestyle.

400 Bronson Rd, Fairfield

$599,000

3 Beds ⋅ 3 Baths ⋅ 24217015 MLS

Highest & Best Offers need to be submitted by 5:00pm on Friday October 30th. Thank you for your interest. Amazing potential is found at this expanded Ranch style home that had an extensive renovation and addition in 2001. Located on a quiet cul-de-sac in Southport. Unbelievable space and floor plan shows the quality details found - expressing the love this home had at one time. Home is occupied and will be sold in "as is" condition. Subject to probate approval. Home will not qualify for conventional financing due to disrepair. Cash or rehabilitation loan only. Do not walk property as it is occupied - listing agent will accompany all limited showings.

54 Steep Hill Rd, Fairfield

$4,950,000

4 Beds ⋅ 5 Baths ⋅ 24206984 MLS

Set on 1.25 acres in the heart of historic Southport Village, 195 Old South Road offers something increasingly rare: the character and presence of an 1829 Federal/Greek Revival residence with an unusually expansive yard. Private and surrounded by mature plantings, the 4,254-square-foot home offers four bedrooms, three full and two half baths across three floors. A gracious Front Hall, anchored by a sweeping curved staircase, opens easily to the home's principal rooms. The sun-filled, 30-foot Living Room features 9-foot ceilings and connects to the Dining Room through a passage framed by arched openings and a built-in wet bar. An expansive Family Room/Sunroom is accessible from the Living Room, Dining Room and Kitchen, creating an easy flow for everyday living and entertaining. Three wood-burning fireplaces add warmth and character. The generous Primary Suite features a gas fireplace, dressing room and private bath. A separate Guest Suite, two additional bedrooms and unfinished upper-level space offer flexibility. A substantial historic barn/garage accommodates two cars, with potential for three, and offers a full second floor. A large, level lawn provides remarkable privacy in close proximity to Southport Harbor, Southport Beach and Metro-North. A rare combination of acreage, architectural character and Village location. 195 Old South Road can be enjoyed immediately while offering its next owners the freedom to make the home distinctly their own over time.

195 Old South Rd, Fairfield

$1,180,000

3 Beds ⋅ 2 Baths ⋅ 24211192 MLS

Welcome to this inviting move in ready three-bedroom home in a desirable Fairfield Southport, where comfortable living, thoughtful updates, and everyday convenience meet together. Set in a peaceful residential neighborhood, this home offers a wonderful balance of privacy and accessibility to both Fairfield's and Westport shopping, dining, parks. Fairfield's vibrant town amenities beaches, and train station all within easy reach. Step inside to bright, welcoming living spaces designed for both everyday life and entertaining. The open kitchen serves as the heart of the home, featuring granite countertops and a seamless connection to the adjoining living and dining areas. The open layout creates an easy flow for gatherings while allowing natural light to move throughout the main living spaces. Three comfortable bedrooms provide flexibility for family and guests. Radiant heat in both family room and sunroom. The finished basement adds valuable additional living space with playroom, home office, sunroom or media area-offering plenty of room to suitable lifestyle. Enjoy the outdoor patio with peaceful surroundings, providing a wonderful setting for dining, gardening, play, or simply relaxing. The combination of a comfortable interior, flexible finished lower level, and convenient Fairfield location makes this home a great opportunity for those looking to enjoy all that the Southport community has to offer.

228 Woodrow Ave, Fairfield

$1,599,000

3 Beds ⋅ 4 Baths ⋅ 24207194 MLS

Welcome to 'The Shire', where everyday life feels like a page from a classic New England novel. This enchanting home captures the timeless spirit of Southport, offering a lifestyle defined by character and the best of the gold coast. From the moment you arrive, the lush, mature grounds set a scene of total serenity, on a property anchored by history, all in an unparalleled location. While the aesthetic is pure vintage charm, the dwelling is equipped for modern peace of mind, including a chefs kitchen, updated bathrooms, and a generator to ensure comfort under any circumstance. Original posts and beams, oversized stone fireplaces, wide plank hardwood floors, and designer lighting all complement the warmth and wonder this antique saltbox exudes. The glass-walled greenhouse is a true sanctuary. Whether you're planting or enjoying your morning coffee, it's a space that brings nature near all year long. The grounds include a barn, offering more than just storage. Inside, you'll find two garage bays as well as a dedicated upstairs studio space, perfect for a secluded office, workshop, gym- the options are endless. Every corner of this estate tells a story, from the sun-dappled nooks to the expansive yard that feels worlds away from the hustle and bustle. This isn't just a house; it's a retreat, waiting for its next chapter to begin. If this one of a kind home feels familiar, it's probably because you've been dreaming about the opportunity to live here... and call The Shire yours.

845 Kings Hwy W, Fairfield

$2,349,000

4 Beds ⋅ 4 Baths ⋅ 24205683 MLS

Secluded Southport mini-estate built with character and attention to detail. Rarely do you find a home that needs nothing. Well loved and enhanced by the current owners including an upper level addition and expanded and renovated kitchen - the home and property have been improved and updated throughout their stewardship. Set on a gentle knoll at the end of a gated drive, enjoy sprawling lawns, professional landscaping and lighting, an inviting heated Gunite pool and enviable privacy. The exterior is further enhanced with a detached barn/garage, a treehouse featured in magazines and a sport court. Fall in love and watch the seasons change on your wraparound front porch. The recently renovated kitchen will delight every home chef. The kitchen and dining is open to a very spacious family room with fireplace, making entertaining a pleasure. Upstairs the romantic and secluded primary suite includes a full bath, plus a separate sitting room/study that is well suited for use as a home office, nursery or dressing room. There are now 3 additional family bedrooms plus two additional full baths. The finished lower level provides great play space and additional living area to enjoy. Gracious, tasteful finishes throughout with meticulous attention to maintenance and quality materials. This is an opportunity to truly have it all.

245 Cedar Rd, Fairfield

$1,699,000

2 Beds ⋅ 2 Baths ⋅ 24205064 MLS

Welcome to 160 Cedar Road, a truly special farmhouse in Southport that has been thoughtfully renovated and reimagined. Filled with warmth, character, and modern updates, this unique property beautifully blends timeless charm with contemporary comfort. Privately set and abutting Aspetuck Land Trust property, the 2-bedroom, possible 3-bedroom, 1.5-bath home enjoys a beautiful natural setting on 4.45 acres while being conveniently close to all that Southport and Fairfield have to offer, including beaches, shopping, restaurants, I95 and the train. The property features a saltwater inground pool, pool cabana, tanning deck, and outdoor shower-creating an exceptional setting for relaxing and entertaining. Three barns, a fenced paddock, and riding ring, along with additional outbuildings and a partially fenced yard, offer tremendous versatility. Rarely does a property combine this much character, thoughtful renovation, privacy, and natural beauty with such a convenient location. 160 Cedar Road is a truly unique property offering a lifestyle unlike any other. Please no driving down driveway without a confirmed appointment- trespassers will be fed to the pigs!

160 Cedar Rd, Fairfield

$3,850,000

5 Beds ⋅ 5 Baths ⋅ 24181784 MLS

This is why so many people fall in love with Southport. Set on an extraordinary .83-acre parcel in the heart of the Village, this circa 1874 residence captures the charm, character, and lifestyle that have made Southport one of New England's most treasured coastal communities. Approached by a long drive and set well back from Harbor Road, the home enjoys a level of privacy rarely found in the Village. Hidden from the road, it offers a sense of seclusion that is increasingly difficult to find. Rich with period details and timeless architectural character, the 5 bedroom, 4 full and 1 half bath home sits at one of the highest points on Harbor Road, where cooling summer breezes are a welcome feature. The property also includes a classic antique barn, pool, pool house, attached one-car garage, and detached two-car garage, creating a setting ideal for both everyday living and entertaining. While the home presents an exceptional opportunity for renovation and enhancement, its greatest assets cannot be replicated: its setting, scale, history, and location. For the next steward, it offers the chance to reimagine a treasured Southport property while preserving its authenticity and charm. Enjoy a quintessential Southport lifestyle with easy access to the Village, train station, Pequot Yacht Club, and the soon-to-open Southport General Store and Rose Hill Kitchen. Last offered for sale in 1989, opportunities like this rarely come to market. A true Southport gem ready for its next chapter

406 Harbor Rd, Fairfield

$8,696,000

7 Beds ⋅ 8 Baths ⋅ 24160984 MLS

Set within artisan stone walls with curated flowering landscapes, this magnificent stone and stucco residence is a masterful tribute to Southport's enduring architectural legacy. Designed to blend seamlessly among the grand neighboring estates of this coveted enclave, 640 Hulls Farm strikes a rare balance: modern in execution, timeless in presence. Construction begins in April with Coastal Luxury Homes, Fairfield County's premiere creator of bespoke residential properties, this 8,560SF masterpiece will embody uncompromising craftsmanship, globally sourced materials, and state-of-the-art systems & technology. Expansive floor-to-ceiling glass invites natural light to cascade throughout the meticulously designed interiors, framing serene views of the manicured grounds and resort-style pool w/spa. The open floor plan is ideal for elegant entertaining and effortless daily living. A chef's kitchen of unrivaled distinction is complemented by a fully appointed scullery, seamlessly supporting both private gatherings and large-scale entertaining. The great room exudes warmth and architectural presence, while the handsome parlor/office opens to an oversized covered porch. The primary suite is a sanctuary unto itself, featuring a fireplace, private terrace, and spa-inspired bath designed for true indulgence. 6 addit'l bedrooms provide luxurious accommodations for family & guests alike. LL is exceptional w/media room, golf simulator, gym, etc. 4 car garage, elevator shaft & much more.

640 Hulls Farm Rd, Fairfield

Start Your Search

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.

Southport Homes for Sale

Newest Southport Homes for Sale

How much is your home worth?

How much is your home worth?