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

$2,699,000

4 Beds ⋅ 4 Baths ⋅ 24191278 MLS

Welcome to Southport! 42 Anvil Rd is a truly custom home, distinctly different in quality and design from the neighboring Toll Brothers builds. Situated on a quiet cul-de-sac with only six homes and backing up to conservation-protected land, it offers exceptional privacy and a serene setting. Step out back to the elevated Brazilian Ipe deck which provides the perfect space for relaxing mornings and sunset dinners. Savor the quiet! Thoughtful details fill every room, from the handsome custom walnut Kitchen island to the stunning Family Room with soaring cathedral ceilings, plentiful windows and French Doors and unique custom finishes throughout. Work from home in the private Office on the main level with a view of your back yard. On the second level, the spacious Primary Suite features spa-inspired luxury with custom wood accents, while three additional Bedrooms accommodate your family and guests beautifully. Do not miss the extraordinary additional living spaces in the Walkout Lower Level including the 5th Bedroom with ensuite Full Bath, a Recreation Room, heated/cooled Full size Gym with 9+ foot ceilings and a heated/cooled two car Garage. 42 Anvil provides versatile living options with the ultimate thoughtful detail. This home is more than just a house, it is a peaceful sanctuary crafted for those who appreciate bespoke design and quality. Come see for yourself how 42 Anvil Rd redefines living in coveted Southport.

42 Anvil Rd, Fairfield

$950,000

3 Beds ⋅ 2 Baths ⋅ 24188073 MLS

Nestled on approximately 1.1 acres in Southport, this classic 1941 Colonial offers a rare opportunity to create something truly special. Set in a picturesque, lightly wooded setting, the property combines privacy with a beautiful natural backdrop. The gently sloping lot opens to a spacious backyard, providing plenty of room to enjoy the outdoors. Inside, you'll find three bedrooms and one full bath, with timeless character ready to be re-imagined. Whether you're looking to restore its original charm or renovate to suit your own style, this home presents an exciting opportunity to bring your vision to life. A peaceful setting, generous acreage, and endless potential make this Southport property one not to miss. Highest & Best by Tuesday July 21st 5pm.

600 Cedar Rd, Fairfield

$3,125,000

6 Beds ⋅ 7 Baths ⋅ 24188287 MLS

Nestled on a private lane, this Southport luxury estate offers a pin-drop quiet setting just minutes from Southport Village, Southport Harbor, the Southport train station, I-95, and the Merritt Parkway. Set on over two level acres, it blends tranquility and convenience. The home features six bedrooms, including a gracious first-floor primary suite with a fireplace, dual spa-like bathrooms, separate dressing areas, and French doors opening to landscaped gardens. A wood-paneled library with a wet bar and a guest suite with a private staircase and full bath add character and flexibility. The country kitchen features wide-plank pine floors, tiled countertops, and Traulsen and Wolf appliances. Outside, an expansive pool, stone terrace, outdoor fireplace, private lighted hardtop sport court, and nine-stall barn showcasing original architectural details complete the setting. Formerly owned by Hall of Fame quarterback Joe Namath.

420 Morehouse Ln, Fairfield

$1,495,000

5 Beds ⋅ 3 Baths ⋅ 24186094 MLS

Welcome to 85 Osborne Place - this beautifully updated 5-bedroom, 2.5-bath Colonial tucked away on a peaceful street, yet just a stroll from the train, shops, and dining is what makes Southport living so desirable. Step inside this turn-key gem to find a bright, flowing floor plan anchored by an updated kitchen that opens seamlessly into a spacious great room - perfect for everyday living and effortless entertaining. A formal dining room and separate living room with fireplace offer classic charm and flexibility, while a dedicated office makes working from home a breeze. The first-floor primary suite gives main-floor living its name with a layout for everyday ease that's hard to find. Upstairs you will find 4 additional bedrooms and an updated hall bath that provide room for everyone. Head down to the finished lower level, where a large rec/playroom awaits - easily reimagined as a home gym, media room, or man/she cave to suit your lifestyle. Outside, your own private retreat: a lovely, fenced yard offers space to play and garden, while the patio with option for shade by a charming awning - is made for morning coffee or evening unwinding. With its unbeatable location, versatile living spaces, and move-in-ready updates, this Southport Colonial checks every box. Don't miss your chance to make it home.

85 Osborne Pl, Fairfield

$599,000

3 Beds ⋅ 2 Baths ⋅ 24184740 MLS ⋅ Southport Woods BLDG.

Pristine 3 Bedroom, 2 Full Bath Main Level End Unit. Newer Kitchen. Private Patio off Kitchen and Living Room. Walk to Southport Village, Train, Harbor, Library. Great Complex that offers Underground Heated Pool & Clubhouse.

18 Southport Woods Dr Unit 18, 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

$1,825,000

3 Beds ⋅ 4 Baths ⋅ 24173387 MLS ⋅ Village At Southport BLDG.

Welcome to refined, like-new construction luxury in the heart of Southport Village. This private enclave is just minutes to the gorgeous beach & harbor, train, library, restaurants & shops, ideally located close to commute & downtown Village living. A lifestyle is what you find, with every high-end amenity, proximity, efficiency and easy, maintenance-free living, yet surrounded by 6-acres of open space and tranquil nature trails. This particular unit was customized from the ground up, with sophisticated, designer-curated finishes throughout. Elevator-ready on all levels. The main living level features a custom kitchen with inset cabinetry, a striking Hale Navy center island, and an abundance of storage, flowing seamlessly into elegant living and dining spaces highlighted by coffered ceilings, detailed focal walls, and oversized windows that flood the home with natural light. Three generously sized bedrooms including a spacious primary suite with a spa-inspired bath and walk-in closet. The finished lower level adds a versatile, apartment-style flexible space complete with a full bath, walk-in closet, and sliding barn doors, offering ideal accommodations for guests, a home office, or additional living area. Note the 2-bay garage and abundance of customized storage on every level. Quality abounds in this more than ready to move in, new energy/feel/vibe, all with location, location, location.

491 Westway Rd Unit 491, Fairfield

$505,000

2 Beds ⋅ 2 Baths ⋅ 24163133 MLS ⋅ Quincy At Southport BLDG.

This first-floor, 2BR, 2-bath unit is in a quiet Southport complex with in-ground pool. Just a short walk to the grocery store, shopping, train, public bus line, bank, and more. The updated unit features a living room with vinyl plank flooring, ceiling fan, wood-burning fireplace with raised marble hearth, plus attractive millwork. Sliding glass doors open to a covered porch with lawn space for gardening and grilling. Dining area has space for a table for 6 or 8. This unit features a full-sized washer and dryer (new in 2017), newer gas HVAC, and water heater in 2022, remodeled hall bath (2019), ample storage, and central air. Updated, fully-applianced eat-in kitchen with tile floor. If you are looking for a place to call home that is warm, inviting, tidy, with neutral paint colors, and ready to just move in- you have found it. Lots of visitor spaces near the unit. Pretty, well maintained grounds as well.

12 Hulls Highway Unit 12, Fairfield

$1,497,000

3 Beds ⋅ 4 Baths ⋅ 24161254 MLS ⋅ Pequot Landing BLDG.

Beautiful End Unit, Perfectly situated in Southport, this beautifully appointed 3-bedroom, 3.5-bath Colonial townhouse end unit offers an exceptional lifestyle just moments from village shops, restaurants, Southport Harbor, and the Metro-North train. Thoughtfully updated, the remodeled kitchen features quartz countertops, a sleek backsplash, and premium Bosch appliances, centered around a generous island-opening seamlessly to a private deck, ideal for entertaining. The open living and dining areas are anchored by a striking double-sided gas fireplace and hardwood floors. The walk-out lower level provides versatile additional space with a full bath and sliders to a private bluestone patio-ideal for relaxing or entertaining. Upstairs, the primary suite offers vaulted ceilings, a spacious walk-in closet, and a beautifully appointed marble bath. Recent updates include new carpet in the primary bedroom and freshly stained upper-level hallway floors. Extensive improvements include a brand-new Electrolux central vacuum system, new washer and dryer, new HVAC system, and a new hot water heater-delivering true turnkey living. Additional features include natural gas heat, central air, main-level laundry, and a 2-car attached garage, with the option to add an elevator. A rare opportunity to experience living in one of Fairfield County's most sought-after coastal communities.

71 Aberdeen Way Unit 71, 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, 688 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 9,422SF 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 & many more wows

688 Hulls Farm Rd, Fairfield

$2,200,000

3 Beds ⋅ 4 Baths ⋅ 24150747 MLS ⋅ Southport Green BLDG.

Rare opportunity in sought-after Southport Green-just steps to Southport Village and Metro-North. One of only two stand-alone residences in this 24-unit enclave, this home offers the privacy of a single-family lifestyle with the ease of condominium living. The townhouse-style residence spans three levels and features 3 bedrooms, 3 renovated full and 1 half baths, plus a coveted attached two-car garage. Thoughtfully designed with flexibility for a future elevator (quote available upon request), it also includes a private patio-an uncommon amenity within the community. Ideal for downsizers or anyone seeking a true "lock-and-leave" lifestyle, this property pairs luxury with everyday convenience. Enjoy dining, shopping, and wellness just moments away at the Delamar Southport, Gray Goose Tavern, and Equinox Health Club.

2 Elmwood Dr Unit 2, Fairfield

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