Southport Homes for Sale

Welcome to Southport, a picturesque neighborhood nestled in the heart of Fairfield, Connecticut. Renowned for its charming coastal ambiance, Southport offers a delightful blend of historic charm and modern living. This idyllic community is characterized by its stunning waterfront views, tree-lined streets, and beautifully preserved 19th-century architecture. Residents here enjoy a serene lifestyle, complemented by the vibrant local culture and a strong sense of community.

Southport boasts an array of amenities, including boutique shops, gourmet dining, and inviting cafés, all within walking distance. The neighborhood is also home to the scenic Southport Harbor, where you can indulge in leisurely strolls along the shoreline or enjoy a day of sailing. The nearby Southport Beach offers a perfect spot for sunbathing, picnicking, and family gatherings, making it an ideal retreat for both relaxation and recreation.

For those considering a move, Southport presents an enticing selection of homes for sale. From charming historic residences to contemporary waterfront properties, the real estate options cater to diverse tastes and lifestyles. Whether you’re seeking a cozy cottage or a grand estate, Southport’s real estate market has something for everyone. The area’s strong schools, proximity to major highways, and easy access to the Metro-North train make it a desirable location for families and commuters alike.

Discover the beauty and charm of Southport, where coastal living meets community spirit. With homes for sale that reflect the character of this enchanting neighborhood, your dream home awaits in this captivating corner of Fairfield. Come experience the allure of Southport today!

Newest Southport Homes for Sale

$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

$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, 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.