1,455 properties for sale in Southport, Fairfield town Fairfield County Connecticut

Enjoy Southport Woods - community lifestyle with pool, clubhouse, paddle tennis and beautifully landscaped grounds in the heart of Southport. Convenient to Fairfield and Southport train stations, I-95, shopping, restaurants, schools and miles of beautiful shoreline, this location offers much. Privately located end unit features slate patio/yard area, two bedrooms (primary with full bath), sizeable living room and dining area off of the galley style Kitchen. Newly painted, furnace replaced in 2024. Hot Water Heater replaced in 2023. Turn the key to care-free living in 2026. One reserved parking space- # 76

SOUTHPORT VILLAGE ITALIANATE VICTORIAN - The Legrand Sherwood William Northrop House - Circa 1872. Ideally located in Southport Village, this exceptional 3,163 square foot, four bedroom Italianate Victorian has been thoughtfully restored and sensitively updated, blending exceptional architectural elements with beautiful interiors. Designer finishes (marble, tiles, fixtures and hardware), complement the extraordinary original detailing, adding style and sophistication. Set on a beautifully landscaped.35 acre property, this sun-filled home welcomes with an expansive front porch spanning the facade - an inviting setting for quiet mornings or evening gatherings. Inside, graciously scaled rooms, high ceilings, and abundant natural light create an elegant and refined, yet very comfortable atmosphere throughout. The main level features a front-to-back living room with a gas fireplace, library lined with custom bookcases, and beautiful formal dining room - ideal for entertaining. The gorgeous

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 Le

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 c

First Time on the Market - A Southport Treasure with Endless Possibilities For the first time since 1912, this cherished Southport residence is being offered. Passed down through generations, this classic colonial has been a cornerstone of one family's legacy for over a century - and now it's ready for its next chapter. Set on nearly a half-acre in the heart of Southport, this property offers tranquil water views, timeless charm, and unmatched potential. Originally a four-bedroom single-family home, a thoughtfully designed in-law suite with its own private entrance, separate mechanicals, and utilities was added in 1991 - ideal for multi-generational living, guests, or rental income. While the home is being sold as-is and does require extensive updating, it offers solid bones and architectural character rarely found today. This is a rare opportunity for someone with creativity and passion - to revive, reimagine, and make this beloved home their own. With its premier location, historic r

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,

Timeless luxury meets exceptional craftsmanship at 98 Banks Place, where a meticulous restoration and rebuild, completed in 2017, transformed an 1830 Greek Revival into a home offering the comfort of new construction while preserving the soul, warmth, and character only a home of this era can provide. Original floors, brick, timbers, custom windows, reclaimed hardware, and period details blend seamlessly with custom millwork, barrel ceilings, Belgian stone flooring, designer finishes, radiant-heated floors, and all-new systems. A chef's kitchen with concealed scullery anchors gracious living spaces, while an inviting family room and serene primary suite balance gathering and retreat. Set on nearly 5.5 private acres, the property is designed for indoor-outdoor living with a resort-style pool, year-round spa, expansive bluestone patio, outdoor kitchen, double-sided fireplace, and new pool house offering flexible space for guests, entertaining, an in-law suite, or future living accommodat

Classic well-loved Southport Green Condo with well-proportioned rooms throughout is ideal for downsizers or someone looking for low maintenance living; convenience awaits you! Enjoy all that the quaint hamlet of Southport has to offer. The condo's perfect sunny layout provides privacy, as well as, plenty of space to socialize. Good-sized Living Room boasts Gas Fireplace. Home Office is located off Living Room, as is Half Bath. Well-designed Kitchen features excellent storage, Sub Zero and Wolf appliances, plenty of counter space and has 2 entry ways. Formal Dining Room is accessed off Kitchen. A lovely set of French Doors opens to cozy Den. Primary Bedroom Suite offers 2 Walk-in Closets, and roomy Bathroom with Stall Shower, Jacuzzi Tub and a 2-sink vanity. A second private en-suite Bedroom has ample-sized Closet space and Bathroom with Tub/Shower. Accessible Elevator provides much usefulness. Historic Southport features sweet, delightful shops and convenient dining. Along your stroll

Note: Townhouse with elevator to all three floors! Welcome to a lovely townhouse community walkable to the train and to Southport Village. Bikeable to Southport Beach! Walk to Equinox. Incredible location. This is a wonderful opportunity for so many people. The rooms are so well proportioned. Entertaining or just everyday living, this home handles both with ease! The lower level family room can easily accomodate over flow company with the adjacent full bath. Don't miss out on this chance to have it all! SUBJECT TO OWNER FINDING SUITABLE HOUSING

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

Gracious Southport Village/Southport Harbor 3Bedroom, 2 1/2Bath Colonial Home, with Water and Harbor views. Enjoy the convenience of walking to all that Southport Village has to offer; Shops, Markets, Restaurants, Pharmacy, Post Office, and Southport Train Station. View and stroll the beautiful streets and homes all overlooking the picturesque Southport Harbor, Long Island Sound and Southport Beaches!

THANK YOU FOR YOUR INTEREST IN 280 MILL HILL ROAD. SELLER IS REQUESTING HIGHEST AND BEST OFFERS TO BE SUBMITTED BY TODAY, MONDAY MAY 11TH AT 5PM. Picture perfect 1920s Colonial in the location we all covet. Welcome to 280 Mill Hill Road, a beautiful center hall colonial that blends timeless character with modern updates-all in an exceptional in-town location. Just a short stroll to Southport Village, this home offers the perfect balance of charm, convenience, and lifestyle. Inside, sun-filled living spaces showcase classic architectural details and a warm, inviting flow ideal. The newly renovated kitchen features stylish finishes and modern functionality, seamlessly complementing the home's historic appeal. The flexible layout includes a finished third floor, perfect as a fourth bedroom, home office, gym or flexible space to suit your needs. Step outside to enjoy an expansive patio overlooking the expansive fenced backyard, surrounded by mature landscaping-an ideal setting for outdoor

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-ne

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,

Enjoy Southport Woods - community lifestyle with pool, clubhouse, paddle tennis and beautifully landscaped grounds in the heart of Southport. Convenient to Fairfield and Southport train stations, I-95, shopping, restaurants, schools and miles of beautiful shoreline, this location offers much. Privately located end unit features slate patio/yard area, two bedrooms (primary with full bath), sizeable living room and dining area off of the galley style Kitchen. Newly painted, furnace replaced in 2024. Hot Water Heater replaced in 2023. Turn the key to care-free living in 2026. One reserved parking space- # 76

Timeless luxury meets exceptional craftsmanship at 98 Banks Place, where a meticulous restoration and rebuild, completed in 2017, transformed an 1830 Greek Revival into a home offering the comfort of new construction while preserving the soul, warmth, and character only a home of this era can provide. Original floors, brick, timbers, custom windows, reclaimed hardware, and period details blend seamlessly with custom millwork, barrel ceilings, Belgian stone flooring, designer finishes, radiant-heated floors, and all-new systems. A chef's kitchen with concealed scullery anchors gracious living spaces, while an inviting family room and serene primary suite balance gathering and retreat. Set on nearly 5.5 private acres, the property is designed for indoor-outdoor living with a resort-style pool, year-round spa, expansive bluestone patio, outdoor kitchen, double-sided fireplace, and new pool house offering flexible space for guests, entertaining, an in-law suite, or future living accommodat

Gracious Southport Village/Southport Harbor 3Bedroom, 2 1/2Bath Colonial Home, with Water and Harbor views. Enjoy the convenience of walking to all that Southport Village has to offer; Shops, Markets, Restaurants, Pharmacy, Post Office, and Southport Train Station. View and stroll the beautiful streets and homes all overlooking the picturesque Southport Harbor, Long Island Sound and Southport Beaches!

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

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-ne

Nestled on a level lot at the end of a peaceful cul-de-sac, this exceptional 5-bedroom, 5-bathroom home offers three levels of thoughtfully designed luxury living. With high-end finishes throughout, this residence perfectly balances modern elegance with everyday comfort. Step inside to discover a first floor featuring a spacious bedroom/offcie and full bath ideal for guests or multigenerational living. The kitchen showcases custom cabinetry, professional-grade appliances, quartz countertops, and a large center island. Entertain effortlessly in the adjacent living area, complete with a sleek gas fireplace and a glass-enclosed, temperature-controlled wine room. On the second level you'll find four generously sized bedrooms, including two that share a Jack-and-Jill bathroom, a third with a private en-suite, and an incredible primary suite. The primary bedroom is the pinnacle of luxury, boasting an expansive walk-in closet and a spa-like bathroom featuring a soaking tub and designer finish

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank