Southport Real Estate

Welcome to Southport, a picturesque gem nestled within the charming town of Fairfield, Connecticut. Known for its stunning coastal views and rich history, Southport offers a unique blend of serene suburban living and vibrant community spirit. This quaint neighborhood is characterized by its tree-lined streets, beautifully preserved historic homes, and a welcoming atmosphere that makes it a delightful place to call home.

One of Southport’s most alluring features is its proximity to the Long Island Sound. Residents can enjoy leisurely strolls along the sandy shores, or partake in various water activities such as sailing, kayaking, and fishing. The Southport Harbor, with its quaint marina and scenic views, serves as a perfect backdrop for those who appreciate the beauty of nature.

The neighborhood is also home to an array of charming boutiques, artisanal shops, and delightful eateries. Whether you’re in the mood for a cozy café or a fine dining experience, Southport has something to satisfy every palate. The community hosts various events throughout the year, fostering a strong sense of camaraderie among residents.

Families will appreciate the top-rated schools in the area, which are known for their commitment to academic excellence and extracurricular opportunities. With its blend of history, natural beauty, and community engagement, Southport is not just a place to live; it’s a place to thrive.

If you’re looking for a neighborhood that embodies the quintessential New England charm, look no further than Southport. Experience the warmth and beauty of this beloved Fairfield community, where every day feels like a vacation.

Newest Listings in Southport

$599,000

3 Beds ⋅ 3 Baths ⋅ 24217015 MLS

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

$5,995,000

4 Beds ⋅ 6 Baths ⋅ 24216271 MLS

Timeless luxury meets exceptional craftsmanship at 98 Banks Place, where a meticulous restoration & rebuild, completed in 2017, transformed an 1830 Greek Revival into a home offering the comfort of new construction while preserving the soul, warmth, & character only a home of this era can provide. Original floors, brick, timbers, custom windows, reclaimed hardware, & period details blend seamlessly with custom millwork, barrel ceilings, Belgian stone flooring, designer finishes, radiant-heated floors, & all-new systems. A chef's kitchen w/ concealed scullery anchors gracious living spaces, while an inviting family room & serene primary suite balance gathering & retreat. Set on nearly 5.5 private acres, the property is designed for indoor-outdoor living w/ a resort-style pool, year-round spa, expansive bluestone patio, outdoor kitchen, double-sided fireplace, & new pool house offering flexible space for guests, entertaining, an in-law suite, or future living accommodations. Sweeping lawns, formal gardens, an apple orchard, enclosed vegetable garden, & mature green screening create a private retreat unlike any other. Moments from Southport Village, Southport Harbor, Pequot Library, Southport Beach, dining, & the train, this is a rare opportunity to enjoy estate-like living in one of Fairfield County's most sought-after coastal communities, where old-world charm, modern ease, & a walkable coastal lifestyle come together in a truly one-of-a-kind offering.

98 Banks Pl, Fairfield

148 Southport Woods Dr Unit 148, Fairfield

$575,000

2 Beds ⋅ 2 Baths ⋅ 24215215 MLS ⋅ Southport Woods BLDG.

Live the Southport lifestyle at Southport Woods, where coastal charm meets resort-style living! This beautiful, freshly painted 2-bedroom, 2-bath first-floor condo new A/C offers the ease of single-level living in a sought-after community conveniently located near everything Fairfield, Southport, and Westport have to offer. The spacious, light-filled layout creates a warm and welcoming atmosphere, while the large, covered patio provides the perfect spot to enjoy your morning coffee, unwind in the evening, or entertain friends. Enjoy a carefree lifestyle with wonderful community amenities, including a heated swimming pool, clubhouse, and paddle tennis courts. Ideally situated just minutes from Southport Village, Southport Harbor, beautiful beaches, fine dining, shopping, and Metro-North, this move-in-ready home offers the perfect blend of comfort, convenience, and lifestyle. Whether you are looking to simplify your living, enjoy a relaxing retreat, or embrace all that coastal Fairfield County has to offer, Southport Woods is a wonderful place to call home!

148 Southport Woods Dr Unit 148, Fairfield

$1,799,000

2 Beds ⋅ 3 Baths ⋅ 24213940 MLS

Historic 1834 farmhouse located in the heart of Southport Village. From the moment you walk through the door you will feel like you are home. Thoughtful renovation of its iconic Pequot Avenue location in 2016 earned the Southport Conservancy Recognition for Restoration. The foundation was completely rebuilt and the home was elevated to FEMA height regulations. All new plumbing and electrical systems were installed. The original wide plank floors, brick and beams were restored to create an inviting open concept. Professionally designed gardens provide beauty and privacy in the outdoor spaces. A rare opportunity to be just steps away from charming Village shops, Southport Harbor and Metro North. This home offers everything from beauty, convenience and warmth. Welcome Home. Listing agent is related to seller.

448 Pequot Ave, Fairfield

$2,695,000

3 Beds ⋅ 4 Baths ⋅ 24186935 MLS ⋅ The Enclave BLDG.

Introducing The Enclave, an exclusive new collection of eight luxury townhomes ideally situated along Old Post Road in the heart of Southport Village. Set within four intimate manor-style buildings, each housing just two residences, these four-level homes combine timeless coastal architecture with sophisticated modern living. Thoughtfully designed for both everyday living and entertaining, each residence features expansive open-concept living spaces, a private elevator servicing all four levels, chef-inspired kitchen, gas fireplace, two-car attached garage and exceptional private outdoor spaces, including a covered porch, rear deck and private fourth-floor roof terrace. A gated entrance provides an added sense of privacy and exclusivity. The Enclave offers a rare combination of privacy and village convenience, adjacent to Southport Park and just moments from Southport Village, Metro-North, the harbor, shops and dining. Currently under construction, with pre-construction opportunities now available.

204 Old Post Rd Unit 1, 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

$1,299,000

3 Beds ⋅ 4 Baths ⋅ 24208534 MLS ⋅ Pequot Landing BLDG.

Step into a lifestyle of effortless elegance at 50 Southport Pl, a stunning 3-story end-unit townhouse nestled w/i the coveted Pequot Landing enclave. Blt in 2004, beautifully refreshed 2021/23, this residence perfectly captures the timeless coastal charm of Southport while offering sophisticated, modern amenities today's discerning buyer craves. From the moment you enter, the quality of the recent upgrades is evident. The interior shines w/freshly painted walls, stylish light fixtures, custom wndw trtmnts & gleaming refinished hardwood floors that lead you through an open, airy layout. The refreshed EIK features a center island, granite countertops, premium SS appliances & w/in pantry. Entertainment flows naturally between the DR & LRs, anchored by a sophisticated double-sided gas fireplace that adds warmth & ambiance to both spaces. For those who work from home, the main-level office/library provides a quiet, refined retreat. Upstairs, the PBR suite serves as a true sanctuary, boasting dramatic vaulted ceilings, a generous walk-in closet, & a new in 2023, spa-like ensuite bath. 2 add'l well-appointed BRs ensure plenty of space for guests or creative uses. The versatility continues on the fin walkout LL, w/its own FBA & French doors leading to a private patio, this space is ready to become a high-end fitness studio, a second offic, or an add'l BR suite. The home also features direct garage access & a thoughtful design that is elevator-ready for future proofing lifestyle.

50 Southport Pl Unit 50, Fairfield

$1,645,000

3 Beds ⋅ 3 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

$1,495,000

3 Beds ⋅ 3 Baths ⋅ 24205674 MLS

SOUTHPORT CHARM, WALK TO EVERYTHING.... Ideally situated in the coveted town of Southport, this custom designer residence offers an exceptional opportunity to enjoy the very best that Southport has to offer. Thoughtfully designed for today's lifestyle to maximize both space, functionality and style, the home features an open-concept main level with seamless living offering gas fireplace, in-ceiling speakers, foyer w/glass staircase, Marvin floor to ceiling windows and KLAR steel doors. The bespoke kitchen features Aurea Stone island & floating display shelf, stainless Bosch appliances, induction range & wine cooler. The second floor is anchored by a fabulous primary suite featuring a custom walk-in closet and a beautifully appointed spa-worthy bathroom with soaking tub. An additional guest bedroom with ensuite bath and a light filled office complete the 2nd level. The 3rd floor loft space offers library/study space with custom built-in bookcases and bedroom with built-in bed. A fabulous light filled home with 6" white oak character hardwood flooring throughout. Work from home or work out at home with the temperature controlled detached office, gym or studio. Plentiful storage and large cedar closet in the finished lower level. Lovely outdoor entertaining space with evergreen privacy hedges, bluestone patio and outdoor speakers and wifi. An enviable location, timeless appeal, and the ease of having everything within reach make this a truly special offering. Agent Owned.

624 Center St, 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

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Southport Real Estate

Newest Listings in Southport

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