Southport Real Estate

Welcome to Southport, a picturesque gem nestled within the vibrant town of Fairfield, Connecticut. Renowned for its charming coastal allure and rich historical heritage, Southport offers an idyllic blend of serene living and modern conveniences, making it a sought-after destination for families, professionals, and retirees alike.

One of Southport's most captivating features is its stunning waterfront. The Southport Harbor, with its tranquil waters and scenic views, beckons residents and visitors to enjoy leisurely strolls along the shoreline or partake in various water activities like sailing and kayaking. The area is also home to the historic Southport Beach, where families can bask in the sun, build sandcastles, or enjoy picnics while soaking in the beautiful surroundings.

Southport is steeped in history, with charming colonial architecture and quaint streets that tell the story of its past. The neighborhood is dotted with delightful boutiques, art galleries, and gourmet eateries, offering a vibrant local culture that encourages exploration. The Southport Arts Center hosts various events throughout the year, celebrating the community's artistic spirit.

For those who prioritize education, Southport boasts access to top-rated schools and a strong sense of community involvement. The neighborhood is also conveniently located near major highways and the Metro-North train station, making commuting to New York City a breeze.

With its stunning scenery, rich history, and welcoming community, Southport is more than just a place to live—it's a lifestyle. Discover the charm of Southport, where every day feels like a vacation.

Newest Listings in Southport

$5,625,000

5 Beds ⋅ 6 Baths ⋅ 24193624 MLS

*Offers Due 7/26 at 5PM* 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

$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

$795,000

24167494 MLS

This 1.02 acre parcel offers the rare combination of privacy and premier location. Tucked away in a quiet Southport neighborhood, yet just minutes to the harbor, beaches, train, restaurants, and charming village shops - it's the best of both worlds. The possibilities are endless - City water, City sewer and Natural Gas are available in the street. Whether you envision a timeless New England colonial, a modern coastal farmhouse - this land gives you the freedom to create exactly what you want. Please see attachments - regarding upgrades etc. Half +/- of the lot has been cleared - potential purchaser can clear more if they desire at their expense. Lot has been staked.

844 Mill Hill Ter, 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

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.