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A prime Southport estate location at the Westport line is home to this gracious 5 Bedroom Colonial featuring a rarely found attached main level IN-LAW / AU PAIR APARTMENT with a private entrance, Living/Dining Room, Bedroom and a full Bath. Additionally appreciated, and perfect for today's work from home buyer, is an OFFICE/STUDIO over the barn style oversized detached two car garage. Approached by a long driveway this home is a nature lovers paradise offering complete privacy with the convenience of being approximately 2 miles to Southport Village center, train and harbor. Inside a welcoming Foyer introduces the front to back Living Room with fireplace, formal Dining Room and the charming Family Room with rustic beams, built in bookcases and impressive brick fireplace. This room is open to the Kitchen and the Breakfast Room with atrium door to a two tier deck to enjoy al fresco dining. The Kitchen impresses with abundant cabinetry and counter space including large breakfast bar perfect for gathering friends/family or food prep duties. Adjacent is a mudroom with side door access to the front walk, the laundry/storage room and if desired access to the attached apartment. Five ample Bedrooms occupy the second floor along with generous linen and cedar closet storage. The primary Bedroom offers a walk in closet, Bath with heated floor, double sink vanity and walk in steam shower. A truly private country home just minutes from Southport Village Center, Harbor, Beach and Train

6 Beds ⋅ 4 Baths ⋅ 24106320 MLS

A prime Southport estate location at the Westport line is home to this gracious 5 Bedroom Colonial featuring a rarely found attached main level IN-LAW / AU PAIR APARTMENT with a private entrance, Living/Dining Room, Bedroom and a full Bath. Additionally appreciated, and perfect for today's work from home buyer, is an OFFICE/STUDIO over the barn style oversized detached two car garage. Approached by a long driveway this home is a nature lovers paradise offering complete privacy with the convenience of being approximately 2 miles to Southport Village center, train and harbor. Inside a welcoming Foyer introduces the front to back Living Room with fireplace, formal Dining Room and the charming Family Room with rustic beams, built in bookcases and impressive brick fireplace. This room is open to the Kitchen and the Breakfast Room with atrium door to a two tier deck to enjoy al fresco dining. The Kitchen impresses with abundant cabinetry and counter space including large breakfast bar perfect for gathering friends/family or food prep duties. Adjacent is a mudroom with side door access to the front walk, the laundry/storage room and if desired access to the attached apartment. Five ample Bedrooms occupy the second floor along with generous linen and cedar closet storage. The primary Bedroom offers a walk in closet, Bath with heated floor, double sink vanity and walk in steam shower. A truly private country home just minutes from Southport Village Center, Harbor, Beach and Train

1135 Hulls Farm Rd, Fairfield

$1,365,000

Newly Renovated Colonial in Prime Southport Location. Beautifully updated colonial offering modern comfort and timeless style. Featuring a stunning new custom kitchen with a large center island, professional Thermador appliances, and separate butlers pantry, this home is perfect for both everyday living and entertaining. The open floor plan is filled with natural light and has 9ft ceilings throughout, creating a warm and inviting atmosphere. Upstairs, you'll find four spacious bedrooms, including a luxurious primary suite with a spa-like bath boasting a soaking tub and oversized shower. The finished lower level provides even more living space, including a large main room and an additional bonus room, ideal for a playroom, home gym, or office. Located in a convenient Southport neighborhood, just minutes to major highways, Southport Train Station, shops, and dining. Home is a must see. Nothing to do but move in.

4 Beds ⋅ 3 Baths ⋅ 24148793 MLS

Newly Renovated Colonial in Prime Southport Location. Beautifully updated colonial offering modern comfort and timeless style. Featuring a stunning new custom kitchen with a large center island, professional Thermador appliances, and separate butlers pantry, this home is perfect for both everyday living and entertaining. The open floor plan is filled with natural light and has 9ft ceilings throughout, creating a warm and inviting atmosphere. Upstairs, you'll find four spacious bedrooms, including a luxurious primary suite with a spa-like bath boasting a soaking tub and oversized shower. The finished lower level provides even more living space, including a large main room and an additional bonus room, ideal for a playroom, home gym, or office. Located in a convenient Southport neighborhood, just minutes to major highways, Southport Train Station, shops, and dining. Home is a must see. Nothing to do but move in.

153 Pease Ave, Fairfield

$1,350,000

Nestled on a prime Southport street, just over a mile from the vibrant Fairfield downtown, Southport Harbor, and main train station to NYC, this mid-century modern contemporary ranch offers a harmonious blend of timeless design and modern convenience. As you step into the foyer, your gaze is drawn to the living room's striking wall of glass, framing jaw-dropping views of Long Island Sound. A rustic, floor-to-ceiling, stone fireplace anchors the space, which also leads to an expansive private deck, complete with a shade-providing awning, perfect for outdoor relaxation or entertaining against a backdrop of a quiet, landscaped yard. The dining room, bathed in natural light from a large bay window, sets the stage for memorable gatherings, while the updated eat-in kitchen boasts crisp white cabinetry, granite countertops, and an effortless flow into the dramatic family room. With its vaulted ceiling, dry bar, expansive picture window, and deck access, the family room is a showstopper designed for seamless entertaining. The private bedroom wing includes a serene, large primary suite w/ a picture window overlooking the landscaped backyard, two additional bedrooms, and a spacious full bath with a walk-in shower. The lower level offers even more versatility offering a walk-out play/rec room w/cozy fireplace, large windows, spacious office/guestroom, full bath, and a private entry.

4 Beds ⋅ 2 Baths ⋅ 24173368 MLS

Nestled on a prime Southport street, just over a mile from the vibrant Fairfield downtown, Southport Harbor, and main train station to NYC, this mid-century modern contemporary ranch offers a harmonious blend of timeless design and modern convenience. As you step into the foyer, your gaze is drawn to the living room's striking wall of glass, framing jaw-dropping views of Long Island Sound. A rustic, floor-to-ceiling, stone fireplace anchors the space, which also leads to an expansive private deck, complete with a shade-providing awning, perfect for outdoor relaxation or entertaining against a backdrop of a quiet, landscaped yard. The dining room, bathed in natural light from a large bay window, sets the stage for memorable gatherings, while the updated eat-in kitchen boasts crisp white cabinetry, granite countertops, and an effortless flow into the dramatic family room. With its vaulted ceiling, dry bar, expansive picture window, and deck access, the family room is a showstopper designed for seamless entertaining. The private bedroom wing includes a serene, large primary suite w/ a picture window overlooking the landscaped backyard, two additional bedrooms, and a spacious full bath with a walk-in shower. The lower level offers even more versatility offering a walk-out play/rec room w/cozy fireplace, large windows, spacious office/guestroom, full bath, and a private entry.

211 High Meadow Rd, Fairfield

$1,275,000

This sweet home is located on a desirable, convenient street nestled between Southport and Greenfield Hill. Enjoy an open first floor with a chef's kitchen featuring premium stainless-steel appliances, a waterfall quartz countertop, and a spacious eat-in area. A separate den/flex space behind a half wall provides a perfect spot for work or play, distinct from the living area. The first floor also includes a large dining area, cozy seating, and a gas fireplace. Two access points lead to an expansive deck and patio, ideal for outdoor entertaining. Upstairs, there are four bedrooms (one without a closet, so the tax card lists it as a three-bed), all with hardwood floors. The primary bedroom boasts a vaulted ceiling, a large picture window, a walk-in closet with custom built-ins, and a spa-like bath with a whirlpool tub and separate shower. The other bedrooms share an updated full bath. The finished third level offers versatile space for a workout room or office. The lower level houses the laundry and ample storage. An unfinished area above the two-car garage could become an art studio or guest suite. The private, level yard includes an irrigation system and a peaceful brook behind the fence. Conveniently located near shopping, schools, and commuting routes. Great walking options including an arboretum steps away. New assessment/taxes not reflected until July 2026.

4 Beds ⋅ 3 Baths ⋅ 24167893 MLS

This sweet home is located on a desirable, convenient street nestled between Southport and Greenfield Hill. Enjoy an open first floor with a chef's kitchen featuring premium stainless-steel appliances, a waterfall quartz countertop, and a spacious eat-in area. A separate den/flex space behind a half wall provides a perfect spot for work or play, distinct from the living area. The first floor also includes a large dining area, cozy seating, and a gas fireplace. Two access points lead to an expansive deck and patio, ideal for outdoor entertaining. Upstairs, there are four bedrooms (one without a closet, so the tax card lists it as a three-bed), all with hardwood floors. The primary bedroom boasts a vaulted ceiling, a large picture window, a walk-in closet with custom built-ins, and a spa-like bath with a whirlpool tub and separate shower. The other bedrooms share an updated full bath. The finished third level offers versatile space for a workout room or office. The lower level houses the laundry and ample storage. An unfinished area above the two-car garage could become an art studio or guest suite. The private, level yard includes an irrigation system and a peaceful brook behind the fence. Conveniently located near shopping, schools, and commuting routes. Great walking options including an arboretum steps away. New assessment/taxes not reflected until July 2026.

1482 Bronson Rd, Fairfield

$1,250,500

The Sherwood Farmhouse set in Southport's Mill Hill area, Circa 1720, is tucked away on a picturesque .48-acre lot in an enchanting country setting. This beautifully preserved and thoughtfully updated historic treasure blends 18th-century charm with modern comforts. Original features such as wide plank floors, hand-hewn beams, custom cupboards, and three working fireplaces speak to the home's rich heritage. Recent updates include a stunning new full bath, a stylish half bath, new wood shingle roof 2024, and a newly built barn with a three-car garage and spacious loft-ideal for a studio, office, or guest suite. Dimensions for the loft above the garage are 31 X 24'. The barn was built by the owner from 200 year old trees on the property. A rare and truly special offering in a truly exceptional Southport location. Close to trains, Southport and Fairfield Centers, schools, beaches, Pequot Library, restaurants and so much more! A hidden gem!

2 Beds ⋅ 2 Baths ⋅ 24119493 MLS

The Sherwood Farmhouse set in Southport's Mill Hill area, Circa 1720, is tucked away on a picturesque .48-acre lot in an enchanting country setting. This beautifully preserved and thoughtfully updated historic treasure blends 18th-century charm with modern comforts. Original features such as wide plank floors, hand-hewn beams, custom cupboards, and three working fireplaces speak to the home's rich heritage. Recent updates include a stunning new full bath, a stylish half bath, new wood shingle roof 2024, and a newly built barn with a three-car garage and spacious loft-ideal for a studio, office, or guest suite. Dimensions for the loft above the garage are 31 X 24'. The barn was built by the owner from 200 year old trees on the property. A rare and truly special offering in a truly exceptional Southport location. Close to trains, Southport and Fairfield Centers, schools, beaches, Pequot Library, restaurants and so much more! A hidden gem!

1135 Mill Hill Rd, Fairfield

$1,226,000

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.

2 Beds ⋅ 4 Baths ⋅ 24170989 MLS ⋅ Pequot Landing BLDG.

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.

70 Southport Pl, Fairfield

$1,190,000

Nestled in the heart of historic Southport, this beautifully updated Colonial blends timeless charm with chic modern sophistication. The 3-bedroom, 2.5-bath residence showcases a newly renovated primary suite and new bathroom with heated floors. The sun-filled kitchen, and thoughtfully updated bathrooms are all complemented by refinished hardwood floors and abundant natural light throughout. A covered porch with swing, sets the tone for relaxed coastal living, while the new wraparound deck overlooks a spacious, level, professionally landscaped backyard ideal for entertaining and outdoor enjoyment. Recent upgrades including a new roof and freshly painted exterior provide turnkey peace of mind. Perfectly positioned just moments from the train, Southport Village, Fairfield's beaches, and top-rated schools, this exceptional home offers the best of historic character and everyday convenience.

3 Beds ⋅ 3 Baths ⋅ 24160361 MLS

Nestled in the heart of historic Southport, this beautifully updated Colonial blends timeless charm with chic modern sophistication. The 3-bedroom, 2.5-bath residence showcases a newly renovated primary suite and new bathroom with heated floors. The sun-filled kitchen, and thoughtfully updated bathrooms are all complemented by refinished hardwood floors and abundant natural light throughout. A covered porch with swing, sets the tone for relaxed coastal living, while the new wraparound deck overlooks a spacious, level, professionally landscaped backyard ideal for entertaining and outdoor enjoyment. Recent upgrades including a new roof and freshly painted exterior provide turnkey peace of mind. Perfectly positioned just moments from the train, Southport Village, Fairfield's beaches, and top-rated schools, this exceptional home offers the best of historic character and everyday convenience.

26 Taylor Pl, Fairfield

$1,175,000

Welcome to Cedar Road, an exceptional opportunity in the exclusive Southport section of Fairfield. This custom-built 1991 colonial is perfectly positioned at the foot of Greenfield Hill, just moments from Southport Village, Westport, and Fairfield shopping. Surrounded by multimillion-dollar estates, this home is a true diamond in the rough with outstanding potential for renovation and value appreciation. A set of double entry doors welcomes you into a spacious foyer. The front-to-back living room features a stone fireplace and double sliding French doors. The formal dining room flows into the eat-in kitchen with sliding French doors to the terrace. A half bath and access to the oversized two-car garage complete the main level. Up the main staircase, a landing offers the perfect space for a home office or study area. The second floor includes two spacious bedrooms with a Jack-and-Jill bath, along with a primary bedroom featuring a full bath and plenty of closet space. A large family room with cathedral ceilings is accessible from both the second floor and a rear stairwell off the kitchen. The finished lower level provides additional living space, along with a dedicated laundry room. Notable features include a whole-house generator and central vacuum system. This is an estate property sold as-is. This home presents an outstanding chance to own a spacious Southport residence for an asking price under one million dollars. Click the link to view the virtual tour.

3 Beds ⋅ 3 Baths ⋅ 24142704 MLS

Welcome to Cedar Road, an exceptional opportunity in the exclusive Southport section of Fairfield. This custom-built 1991 colonial is perfectly positioned at the foot of Greenfield Hill, just moments from Southport Village, Westport, and Fairfield shopping. Surrounded by multimillion-dollar estates, this home is a true diamond in the rough with outstanding potential for renovation and value appreciation. A set of double entry doors welcomes you into a spacious foyer. The front-to-back living room features a stone fireplace and double sliding French doors. The formal dining room flows into the eat-in kitchen with sliding French doors to the terrace. A half bath and access to the oversized two-car garage complete the main level. Up the main staircase, a landing offers the perfect space for a home office or study area. The second floor includes two spacious bedrooms with a Jack-and-Jill bath, along with a primary bedroom featuring a full bath and plenty of closet space. A large family room with cathedral ceilings is accessible from both the second floor and a rear stairwell off the kitchen. The finished lower level provides additional living space, along with a dedicated laundry room. Notable features include a whole-house generator and central vacuum system. This is an estate property sold as-is. This home presents an outstanding chance to own a spacious Southport residence for an asking price under one million dollars. Click the link to view the virtual tour.

1213 Cedar Rd, Fairfield

$1,100,000

An Exceptional Southport Opportunity ~ Now complete and ready for immediate occupancy, this distinguished Southport residence has been meticulously renovated by Southport Construction LLC, delivering the level of craftsmanship, finish, and execution expected at the highest end of the market. The home presents as a refined, new-construction-quality offering within an established coastal setting. The interiors are designed with a restrained, timeless sensibility. A bespoke kitchen anchors the home, featuring custom cabinetry, full-height quartz surfaces, and a thoughtfully selected suite of Bosch appliances, including a 36" gas range, counter-depth French door refrigerator, integrated dishwasher, and concealed hood-balancing elegance with everyday function. Bathrooms are curated as serene, spa-inspired spaces with custom quartz vanities, elevated fixtures, and refined finishes. The primary suite offers a private retreat, defined by proportion, natural light, and subtle architectural detail. Beyond the finishes, the home has been comprehensively rebuilt with modern mechanical systems, energy-efficient construction, and high-performance materials-offering the comfort and peace of mind typically associated with new construction. Ideally located near the village, harbor, beaches, and Metro-North, this is a rare opportunity to secure a fully renovated, design-driven home by a trusted local builder-ready to be enjoyed immediately.

3 Beds ⋅ 3 Baths ⋅ 24155163 MLS

An Exceptional Southport Opportunity ~ Now complete and ready for immediate occupancy, this distinguished Southport residence has been meticulously renovated by Southport Construction LLC, delivering the level of craftsmanship, finish, and execution expected at the highest end of the market. The home presents as a refined, new-construction-quality offering within an established coastal setting. The interiors are designed with a restrained, timeless sensibility. A bespoke kitchen anchors the home, featuring custom cabinetry, full-height quartz surfaces, and a thoughtfully selected suite of Bosch appliances, including a 36" gas range, counter-depth French door refrigerator, integrated dishwasher, and concealed hood-balancing elegance with everyday function. Bathrooms are curated as serene, spa-inspired spaces with custom quartz vanities, elevated fixtures, and refined finishes. The primary suite offers a private retreat, defined by proportion, natural light, and subtle architectural detail. Beyond the finishes, the home has been comprehensively rebuilt with modern mechanical systems, energy-efficient construction, and high-performance materials-offering the comfort and peace of mind typically associated with new construction. Ideally located near the village, harbor, beaches, and Metro-North, this is a rare opportunity to secure a fully renovated, design-driven home by a trusted local builder-ready to be enjoyed immediately.

279 Spruce St, Fairfield

$1,000,000

Enjoy everything that Southport has to offer!!! This beautiful home is situated on a peaceful cul-de-sac just around the corner from the Pequot Library, Southport Beach, the Harbor and of course, the quaint Village. Whether you sail, swim or simply beach, this spot is perfect for you! Enter the front foyer of this beautiful home, hang up your coat and now you can relax. Step into the comfortable living room with a wood burning fireplace and a quiet, sun-filled office on the side. This well maintained home is ready to move in with a beautifully renovated kitchen which opens to the dining room and there are two entrances to the living room, providing a wonderful flow for entertaining. If you enter from the garage, there's a spacious mudroom that provides a built-in seat and storage and a pantry, plus this is where you'll find a half bath and laundry room... all conveniently located steps from the kitchen. The large main floor primary bedroom with full bathroom is ideal for many homeowners and the large bedrooms and bathroom upstairs provide great space for children or guests. Enjoy the fully fenced backyard with intentional plantings to provide total privacy. You'll love it here, come take a look!

3 Beds ⋅ 3 Baths ⋅ 24132909 MLS

Enjoy everything that Southport has to offer!!! This beautiful home is situated on a peaceful cul-de-sac just around the corner from the Pequot Library, Southport Beach, the Harbor and of course, the quaint Village. Whether you sail, swim or simply beach, this spot is perfect for you! Enter the front foyer of this beautiful home, hang up your coat and now you can relax. Step into the comfortable living room with a wood burning fireplace and a quiet, sun-filled office on the side. This well maintained home is ready to move in with a beautifully renovated kitchen which opens to the dining room and there are two entrances to the living room, providing a wonderful flow for entertaining. If you enter from the garage, there's a spacious mudroom that provides a built-in seat and storage and a pantry, plus this is where you'll find a half bath and laundry room... all conveniently located steps from the kitchen. The large main floor primary bedroom with full bathroom is ideal for many homeowners and the large bedrooms and bathroom upstairs provide great space for children or guests. Enjoy the fully fenced backyard with intentional plantings to provide total privacy. You'll love it here, come take a look!

74 Westford Dr, Fairfield

$990,000

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.

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

$880,000

**Highest and Best by Tuesday 11/18 at 12** Set in the heart of Southport, this well-maintained 3-bedroom, 1.5-bath Colonial offers exceptional potential in one of Fairfield's most picturesque coastal communities. Loved by one family since it was built in 1955, the home features solid craftsmanship, hardwood floors, and a light-filled layout. The first floor includes a traditional center hall design with a front-to-back living room with a wood-burning fireplace, an eat-in kitchen with original mid-century details and pantry, a spacious dining room, half bath, and a bright sun porch overlooking the backyard, an ideal mudroom. Upstairs are three generously sized bedrooms, a full bath, and excellent storage. The front-to-back primary bedroom includes access to the walk-up attic, offering expansion potential for an office, family room, or future primary suite. The unfinished lower level provides additional storage or finishing possibilities. The home is set on a level .43-acre lot with mature trees and features a detached two-car garage and partially fenced yard. The location adds incredible value- walking distance to Mill Hill Elementary School and just over a mile to Southport Village's shops, restaurants, and train station. Surrounded by million-dollar homes, this property offers a rare opportunity for buyers or builders to create something truly special. **Buyers to do their due diligence**

3 Beds ⋅ 2 Baths ⋅ 24140193 MLS

**Highest and Best by Tuesday 11/18 at 12** Set in the heart of Southport, this well-maintained 3-bedroom, 1.5-bath Colonial offers exceptional potential in one of Fairfield's most picturesque coastal communities. Loved by one family since it was built in 1955, the home features solid craftsmanship, hardwood floors, and a light-filled layout. The first floor includes a traditional center hall design with a front-to-back living room with a wood-burning fireplace, an eat-in kitchen with original mid-century details and pantry, a spacious dining room, half bath, and a bright sun porch overlooking the backyard, an ideal mudroom. Upstairs are three generously sized bedrooms, a full bath, and excellent storage. The front-to-back primary bedroom includes access to the walk-up attic, offering expansion potential for an office, family room, or future primary suite. The unfinished lower level provides additional storage or finishing possibilities. The home is set on a level .43-acre lot with mature trees and features a detached two-car garage and partially fenced yard. The location adds incredible value- walking distance to Mill Hill Elementary School and just over a mile to Southport Village's shops, restaurants, and train station. Surrounded by million-dollar homes, this property offers a rare opportunity for buyers or builders to create something truly special. **Buyers to do their due diligence**

476 Mill Hill Ter, Fairfield

$865,000

First Time on the Market - A Southport Treasure with Endless Possibilities For the first time since 1912, this cherished Southport residence is being offered for sale. 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 roots, and flexible layout, this Southport gem is ready to be transformed into something truly extraordinary.

4 Beds ⋅ 3 Baths ⋅ 24168753 MLS

First Time on the Market - A Southport Treasure with Endless Possibilities For the first time since 1912, this cherished Southport residence is being offered for sale. 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 roots, and flexible layout, this Southport gem is ready to be transformed into something truly extraordinary.

647 Bronson Rd, Fairfield

$860,000

Welcome to this expanded ranch in the gorgeous Southport neighborhood. A sun-drenched living room with a cozy fireplace welcomes you into the home, creating the perfect space to relax or entertain. The main level features three bedrooms, including a primary suite, along with two full bathrooms. Convenience is key with a laundry room located on the main level. The expansive family room offers walls of windows that fill the space with natural light and provide beautiful views of the surrounding property. The kitchen has been updated with granite countertops and offers a functional layout ready for everyday living. Set on a gorgeous corner lot, this property offers wonderful outdoor space complete with deck and endless potential to make it your own. For those looking to build new, the home can also be purchased with approved plans for a 4-5 bedroom, 4 bathroom residence totaling over 3,400 square feet. The owner, a builder, has already completed the extensive groundwork for approval. The new construction would carry an address on Evelyn, with the driveway and main entrance facing Evelyn. Inquire with the listing agent for additional details and plans. SELLER WOULD LIKE TO HAVE ALL OFFERS IN HAND BY TUESDAY, MARCH 17TH AT 5PM.

3 Beds ⋅ 2 Baths ⋅ 24157226 MLS

Welcome to this expanded ranch in the gorgeous Southport neighborhood. A sun-drenched living room with a cozy fireplace welcomes you into the home, creating the perfect space to relax or entertain. The main level features three bedrooms, including a primary suite, along with two full bathrooms. Convenience is key with a laundry room located on the main level. The expansive family room offers walls of windows that fill the space with natural light and provide beautiful views of the surrounding property. The kitchen has been updated with granite countertops and offers a functional layout ready for everyday living. Set on a gorgeous corner lot, this property offers wonderful outdoor space complete with deck and endless potential to make it your own. For those looking to build new, the home can also be purchased with approved plans for a 4-5 bedroom, 4 bathroom residence totaling over 3,400 square feet. The owner, a builder, has already completed the extensive groundwork for approval. The new construction would carry an address on Evelyn, with the driveway and main entrance facing Evelyn. Inquire with the listing agent for additional details and plans. SELLER WOULD LIKE TO HAVE ALL OFFERS IN HAND BY TUESDAY, MARCH 17TH AT 5PM.

1120 Mill Hill Ter, Fairfield

$850,000

Welcome to this terrific, charming colonial home in Southport! This home offers an excellent combination of vintage charm along with updates for todays lifestyle! Sited on a corner lot with a classic white rail fence, this home welcomes you with a tradtional front porch. The entry foyer is a nice size and leads to the formal living room with cozy fireplace, hardwood floors and moldings. Adjacent to the living room, is what can be either a family room or den, as well as an updated full bathroom with tub. The formal dining room is great for entertaining and leads to the bright, updated kitchen with center island, stainless steel appliances and marble counters. A sunny mud room entrance completes the first floor and leads to the backyard patio. Upstairs, you will find three nice bedrooms, as well as another updated full bathroom. There is a nicely sized yard as well. A newer roof (2022) and tankless hotwater unit (2024) completes the picture! Such a great location, close to Southport Village, restaurants, shopping, as well as I-95 and the train station. A wonderful place to call your new home!

3 Beds ⋅ 2 Baths ⋅ 24170919 MLS

Welcome to this terrific, charming colonial home in Southport! This home offers an excellent combination of vintage charm along with updates for todays lifestyle! Sited on a corner lot with a classic white rail fence, this home welcomes you with a tradtional front porch. The entry foyer is a nice size and leads to the formal living room with cozy fireplace, hardwood floors and moldings. Adjacent to the living room, is what can be either a family room or den, as well as an updated full bathroom with tub. The formal dining room is great for entertaining and leads to the bright, updated kitchen with center island, stainless steel appliances and marble counters. A sunny mud room entrance completes the first floor and leads to the backyard patio. Upstairs, you will find three nice bedrooms, as well as another updated full bathroom. There is a nicely sized yard as well. A newer roof (2022) and tankless hotwater unit (2024) completes the picture! Such a great location, close to Southport Village, restaurants, shopping, as well as I-95 and the train station. A wonderful place to call your new home!

180 Oxford Rd, Fairfield

$835,000

Welcome to 157 Hulls Highway Southport Charmer! This 3 bedroom, 2 bath is the perfect blend of warmth, comfort and timeless charm with thoughtful modern updates. The open floor plan is designed for the way we live today. The heart of the home is the updated kitchen, featuring quartz countertops, S/S appliances, a center island with breakfast bar, perfect for morning coffee, quick dinners, homework nights, and gathering with family and friends. The kitchen opens to the cozy family room, while the separate dining room provides an elegant setting for holiday celebrations and memorable dinners. Sliding doors lead to a private deck and fully fenced backyard, an ideal extension of the home for summer barbecues, lawn games, and relaxed evenings under the stars. A side entrance creates a practical drop zone for coats, backpacks, and shoes. The first floor offers a spacious bedroom and renovated full bath, providing flexibility for guests, a home office, or convenient one level living. Upstairs, you'll find two oversized bedrooms, including the serene Primary Suite and a spa like bath with Carrara marble finishes. The second bedroom also enjoys access to this beautifully updated bathroom. The finished lower level offers versatile space for a family room, playroom or office. Just minutes to Southport Village, Southport Station, local beaches, Westport, shopping and restaurants.

3 Beds ⋅ 2 Baths ⋅ 24174783 MLS

Welcome to 157 Hulls Highway Southport Charmer! This 3 bedroom, 2 bath is the perfect blend of warmth, comfort and timeless charm with thoughtful modern updates. The open floor plan is designed for the way we live today. The heart of the home is the updated kitchen, featuring quartz countertops, S/S appliances, a center island with breakfast bar, perfect for morning coffee, quick dinners, homework nights, and gathering with family and friends. The kitchen opens to the cozy family room, while the separate dining room provides an elegant setting for holiday celebrations and memorable dinners. Sliding doors lead to a private deck and fully fenced backyard, an ideal extension of the home for summer barbecues, lawn games, and relaxed evenings under the stars. A side entrance creates a practical drop zone for coats, backpacks, and shoes. The first floor offers a spacious bedroom and renovated full bath, providing flexibility for guests, a home office, or convenient one level living. Upstairs, you'll find two oversized bedrooms, including the serene Primary Suite and a spa like bath with Carrara marble finishes. The second bedroom also enjoys access to this beautifully updated bathroom. The finished lower level offers versatile space for a family room, playroom or office. Just minutes to Southport Village, Southport Station, local beaches, Westport, shopping and restaurants.

157 Hulls Hwy, Fairfield

$685,000

Welcome to this charming Cape Cod-style home, offering an inviting entry into the quaint, historic village of Southport. Recently refreshed with a full interior repaint in a crisp, clean white palette, the home feels bright, open, and thoughtfully updated, with sparsely furnished spaces that highlight the light, flow, and flexibility. Recent improvements include a brand-new furnace, a new above-the-range microwave, and a Bosch dishwasher, while the roof carries a transferable warranty for added peace of mind. The home opens to a deck overlooking a naturally sloped backyard, creating a comfortable outdoor space for relaxing or entertaining without the burden of heavy yard maintenance. Set within an excellent school district, this property also offers exceptional walkability, just minutes to the harbor, train station, and charming village shops. A move-in-ready opportunity to enjoy classic New England charm, fresh updates, and one of Fairfield County's most desirable coastal communities.

3 Beds ⋅ 2 Baths ⋅ 24130595 MLS

Welcome to this charming Cape Cod-style home, offering an inviting entry into the quaint, historic village of Southport. Recently refreshed with a full interior repaint in a crisp, clean white palette, the home feels bright, open, and thoughtfully updated, with sparsely furnished spaces that highlight the light, flow, and flexibility. Recent improvements include a brand-new furnace, a new above-the-range microwave, and a Bosch dishwasher, while the roof carries a transferable warranty for added peace of mind. The home opens to a deck overlooking a naturally sloped backyard, creating a comfortable outdoor space for relaxing or entertaining without the burden of heavy yard maintenance. Set within an excellent school district, this property also offers exceptional walkability, just minutes to the harbor, train station, and charming village shops. A move-in-ready opportunity to enjoy classic New England charm, fresh updates, and one of Fairfield County's most desirable coastal communities.

53 Hilltop Dr, Fairfield

195 Southport Woods Dr Unit 195, Fairfield

$637,555

Rare to find - a renovated & sun filled end unit. 2brs 2bths, exceptional condo with deck & large garage with locked storage. Engineered open floor plan from living room to kitchen and dining area - perfect for entertaining & bright sunshine. All NEW windows, GE SS appliances, quartz counters, hardwood laminate floors & new 2026 water heater, quiet on 2nd floor. white kitchen boasts convection oven/air fryer, microwave, roll out in cabinets and in tall pantry, E-disposal and E-chargers. Large & beautiful primary suite with volume ceilings and paddle fan with light, exceptional 4 inch crown molding. Enjoy custom walk in closet & built-ins, new marble floor & walk in shower with square rain heads. W/D tucked away, high hats galore and California dimmers. Amazing deck to dine al fresco or gaze at the stars - 28' x 10' with solar lights, humming birds & views of pink dogwoods. Across from heated pool. Wine refrig to transfer with unit. More built-ins in hall for storage, new garage lift & keypad with tremendous locked storage. All bids to be submitted before May 25th. Flexible close possible, all furniture for sale less art & sold as is. Close to beach, train & restaurants. Lower Greenfield Hill & Southport at its absolute finest.

2 Beds ⋅ 2 Baths ⋅ 24163665 MLS ⋅ Southport Woods BLDG.

Rare to find - a renovated & sun filled end unit. 2brs 2bths, exceptional condo with deck & large garage with locked storage. Engineered open floor plan from living room to kitchen and dining area - perfect for entertaining & bright sunshine. All NEW windows, GE SS appliances, quartz counters, hardwood laminate floors & new 2026 water heater, quiet on 2nd floor. white kitchen boasts convection oven/air fryer, microwave, roll out in cabinets and in tall pantry, E-disposal and E-chargers. Large & beautiful primary suite with volume ceilings and paddle fan with light, exceptional 4 inch crown molding. Enjoy custom walk in closet & built-ins, new marble floor & walk in shower with square rain heads. W/D tucked away, high hats galore and California dimmers. Amazing deck to dine al fresco or gaze at the stars - 28' x 10' with solar lights, humming birds & views of pink dogwoods. Across from heated pool. Wine refrig to transfer with unit. More built-ins in hall for storage, new garage lift & keypad with tremendous locked storage. All bids to be submitted before May 25th. Flexible close possible, all furniture for sale less art & sold as is. Close to beach, train & restaurants. Lower Greenfield Hill & Southport at its absolute finest.

195 Southport Woods Dr Unit 195, Fairfield

$620,000

Welcome home to 28 Mill Hill Road #28! This first-floor ranch style condo in Southport Woods East presents a great opportunity to enjoy living in a sought-after community. Designed for effortless one level living, this move-in ready home offers both a gracious front entrance and a private exterior entry, providing comfort, privacy and ease. The interior has been updated with fresh paint and newer full baths, is bright and spacious with an open layout that flows beautifully for both everyday living and entertaining. Three well sized bedrooms offer flexibility, including a primary suite with a walk-in closet and a private bath. The kitchen opens to the dining and living areas, complemented by new flooring and clean, fresh paint and modern finishes throughout. A private storage room adds a level of convenience. Relax during the warmer months with your association private pool. Southport Village is just a short walk away with its charming shops, cafes, restaurants and harbor. The train station is nearby for easy commuting, Southport Beach is less than two miles away, and Fairfield town center is only minutes away. Opportunities like this are hard to find. Enjoy the chance to live in the heart of Southport, where one level comfort, style and location come together effortlessly.

3 Beds ⋅ 2 Baths ⋅ 24153185 MLS

Welcome home to 28 Mill Hill Road #28! This first-floor ranch style condo in Southport Woods East presents a great opportunity to enjoy living in a sought-after community. Designed for effortless one level living, this move-in ready home offers both a gracious front entrance and a private exterior entry, providing comfort, privacy and ease. The interior has been updated with fresh paint and newer full baths, is bright and spacious with an open layout that flows beautifully for both everyday living and entertaining. Three well sized bedrooms offer flexibility, including a primary suite with a walk-in closet and a private bath. The kitchen opens to the dining and living areas, complemented by new flooring and clean, fresh paint and modern finishes throughout. A private storage room adds a level of convenience. Relax during the warmer months with your association private pool. Southport Village is just a short walk away with its charming shops, cafes, restaurants and harbor. The train station is nearby for easy commuting, Southport Beach is less than two miles away, and Fairfield town center is only minutes away. Opportunities like this are hard to find. Enjoy the chance to live in the heart of Southport, where one level comfort, style and location come together effortlessly.

28 Mill Hill Rd Unit 28, Fairfield

$613,300

Reduced!! Location, location and Location! Here is a chance to build some sweet equity that you have been waiting for! With 4 Bedrooms and 3 full bathrooms there is room for all. Living room with a fireplace along with two additional sitting room to accommodate all your guests. Partially fenced in yard, detached garage. Central air, gas heat, tankless hot water heater , 2 car detached garage, drive way long enough to accommodate all your cars and much more. Connecticut Choice Realty LLC and Raine company makes no representing of the condition of the home and the MLS information supplied. Please do your diligence. Please visit www.Hudhomestore.com and follow the directions to make an offer. Close to all amenities and highways. This is a HUD Home and sold in AS-IS condition. Make it your home today!

4 Beds ⋅ 3 Baths ⋅ 24163349 MLS

Reduced!! Location, location and Location! Here is a chance to build some sweet equity that you have been waiting for! With 4 Bedrooms and 3 full bathrooms there is room for all. Living room with a fireplace along with two additional sitting room to accommodate all your guests. Partially fenced in yard, detached garage. Central air, gas heat, tankless hot water heater , 2 car detached garage, drive way long enough to accommodate all your cars and much more. Connecticut Choice Realty LLC and Raine company makes no representing of the condition of the home and the MLS information supplied. Please do your diligence. Please visit www.Hudhomestore.com and follow the directions to make an offer. Close to all amenities and highways. This is a HUD Home and sold in AS-IS condition. Make it your home today!

329 Bronson Rd, Fairfield

18 Southport Woods Dr Unit 18, Fairfield

$602,000

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.

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

103 Southport Woods Dr Unit 103, Fairfield

$580,000

Live the Southport lifestyle at Southport Woods, where coastal charm meets effortless living.This beautifully refreshed 2-bedroom, 2-bath residence offers rare, single-level living in one of Fairfield County's beautiful communities. The spacious layout is filled with natural light and opens to a large covered patio- perfect for morning coffee, quiet evenings, or effortless entertaining. Freshly painted throughout with updated kitchen and baths. Enjoy resort-style amenities including a sparkling pool, clubhouse, and paddle tennis courts, all within a pet-friendly setting. Just minutes from Southport Harbor and the storybook streets of Southport Village-with beaches, fine dining, shopping, and Metro-North.

2 Beds ⋅ 2 Baths ⋅ 24157082 MLS ⋅ Southport Woods BLDG.

Live the Southport lifestyle at Southport Woods, where coastal charm meets effortless living.This beautifully refreshed 2-bedroom, 2-bath residence offers rare, single-level living in one of Fairfield County's beautiful communities. The spacious layout is filled with natural light and opens to a large covered patio- perfect for morning coffee, quiet evenings, or effortless entertaining. Freshly painted throughout with updated kitchen and baths. Enjoy resort-style amenities including a sparkling pool, clubhouse, and paddle tennis courts, all within a pet-friendly setting. Just minutes from Southport Harbor and the storybook streets of Southport Village-with beaches, fine dining, shopping, and Metro-North.

103 Southport Woods Dr Unit 103, Fairfield

$552,000

Welcome to this beautifully maintained first-floor ranch-style condominium in the highly sought-after Southport Woods East community. This inviting home offers the perfect combination of comfort, convenience, and coastal charm. Enjoy the ease of single-level living with both a welcoming front entry and a private exterior entrance. The spacious floor plan features three generous bedrooms, including a primary suite with a walk-in closet and updated en-suite bath. The open-concept layout seamlessly connects the kitchen, dining, and living areas, creating an ideal space for both everyday living and entertaining. Recent updates include a modernized kitchen, new flooring, and fresh finishes throughout. A private storage room adds extra convenience. Residents of Southport Woods East enjoy access to a sparkling community pool, perfect for relaxing and socializing during the warmer months. The location can't be beat - just a half-mile stroll to Southport Village, where you'll find charming shops, cafes, restaurants, and the picturesque Southport Harbor. Commuters will appreciate the proximity to the train station, while Southport Beach is only 1.5 miles away, offering easy access to sun, sand, and seaside serenity. In just minutes, you can explore Fairfield's vibrant town center, known for its diverse dining, shopping, and entertainment options. Experience the best of easy coastal living-all within 50 miles of New York City. Schedule your private showing today!

3 Beds ⋅ 2 Baths ⋅ 24138856 MLS ⋅ Southport Woods - East BLDG.

Welcome to this beautifully maintained first-floor ranch-style condominium in the highly sought-after Southport Woods East community. This inviting home offers the perfect combination of comfort, convenience, and coastal charm. Enjoy the ease of single-level living with both a welcoming front entry and a private exterior entrance. The spacious floor plan features three generous bedrooms, including a primary suite with a walk-in closet and updated en-suite bath. The open-concept layout seamlessly connects the kitchen, dining, and living areas, creating an ideal space for both everyday living and entertaining. Recent updates include a modernized kitchen, new flooring, and fresh finishes throughout. A private storage room adds extra convenience. Residents of Southport Woods East enjoy access to a sparkling community pool, perfect for relaxing and socializing during the warmer months. The location can't be beat - just a half-mile stroll to Southport Village, where you'll find charming shops, cafes, restaurants, and the picturesque Southport Harbor. Commuters will appreciate the proximity to the train station, while Southport Beach is only 1.5 miles away, offering easy access to sun, sand, and seaside serenity. In just minutes, you can explore Fairfield's vibrant town center, known for its diverse dining, shopping, and entertainment options. Experience the best of easy coastal living-all within 50 miles of New York City. Schedule your private showing today!

28 Mill Hill Rd Unit 28, Fairfield

$552,000

Nestled in the serene enclave of Quincy Condominiums in Southport, this two-bedroom, two-bath end unit offers the perfect blend of tranquility and convenience. Just minutes from Southport Village, Westport shopping, and Fairfield Center, the location provides easy access to everything while maintaining a serene, private setting. This boutique community of only 40 units is surrounded by beautifully manicured grounds and features an inviting in-ground pool for summer relaxation. Inside, the residence welcomes you with warmth and charm. The spacious living room boasts a wood-burning fireplace and opens to a screened porch overlooking the landscaped grounds. An updated kitchen with space for a breakfast table connects seamlessly to the dining area, ideal for entertaining. The primary bedroom offers an ensuite bath and generous storage, while the second bedroom is served by a full hall bath. Additional highlights include a private garage with storage (#11) and a reserved parking space (#60). Community details: dogs are not permitted, but up to two cats are welcome. Rentals are allowed after one year of owner occupancy. Click the virtual tour to explore this home and move right in to enjoy all that Quincy Condominiums has to offer!

2 Beds ⋅ 2 Baths ⋅ 24130955 MLS ⋅ Quincy At Southport BLDG.

Nestled in the serene enclave of Quincy Condominiums in Southport, this two-bedroom, two-bath end unit offers the perfect blend of tranquility and convenience. Just minutes from Southport Village, Westport shopping, and Fairfield Center, the location provides easy access to everything while maintaining a serene, private setting. This boutique community of only 40 units is surrounded by beautifully manicured grounds and features an inviting in-ground pool for summer relaxation. Inside, the residence welcomes you with warmth and charm. The spacious living room boasts a wood-burning fireplace and opens to a screened porch overlooking the landscaped grounds. An updated kitchen with space for a breakfast table connects seamlessly to the dining area, ideal for entertaining. The primary bedroom offers an ensuite bath and generous storage, while the second bedroom is served by a full hall bath. Additional highlights include a private garage with storage (#11) and a reserved parking space (#60). Community details: dogs are not permitted, but up to two cats are welcome. Rentals are allowed after one year of owner occupancy. Click the virtual tour to explore this home and move right in to enjoy all that Quincy Condominiums has to offer!

60 Hulls Highway Unit 60, Fairfield

$475,000

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.

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

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