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Welcome to 260 Willow Street-where timeless design meets modern luxury. Thoughtfully reimagined and meticulously executed, this exceptional Southport Village residence embodies architectural refinement and effortless elegance. Renowned architect Christopher Pagliaro's philosophy of "addition by subtraction" is evident throughout, resulting in a home that is both sophisticated and serene. Every space has been curated with an uncompromising attention to detail-from custom millwork to premium finishes-creating an environment that is as functional as it is beautiful. Set on one of the most coveted streets in Southport, this property offers the perfect balance of privacy and proximity. Just a short stroll to the harbor and Long Island Sound, the setting recalls the charm of Nantucket or the Hamptons while retaining the unmistakable character of Southport. The transformation of the entire estate-including the main house, guest house, pool, and pool house-is nothing short of remarkable. The extensive list of upgrades and enhancements is too comprehensive to list here; this is a home that must be seen to be fully appreciated. Experience 260 Willow Street-a residence that invites you to live beautifully, entertain effortlessly, and enjoy the best of coastal village life.

7 Beds ⋅ 7 Baths ⋅ 24109531 MLS

Welcome to 260 Willow Street-where timeless design meets modern luxury. Thoughtfully reimagined and meticulously executed, this exceptional Southport Village residence embodies architectural refinement and effortless elegance. Renowned architect Christopher Pagliaro's philosophy of "addition by subtraction" is evident throughout, resulting in a home that is both sophisticated and serene. Every space has been curated with an uncompromising attention to detail-from custom millwork to premium finishes-creating an environment that is as functional as it is beautiful. Set on one of the most coveted streets in Southport, this property offers the perfect balance of privacy and proximity. Just a short stroll to the harbor and Long Island Sound, the setting recalls the charm of Nantucket or the Hamptons while retaining the unmistakable character of Southport. The transformation of the entire estate-including the main house, guest house, pool, and pool house-is nothing short of remarkable. The extensive list of upgrades and enhancements is too comprehensive to list here; this is a home that must be seen to be fully appreciated. Experience 260 Willow Street-a residence that invites you to live beautifully, entertain effortlessly, and enjoy the best of coastal village life.

260 Willow St, Fairfield

$3,750,000

Step into history in the heart of Southport Village, where this location doesn't get any better! On Pequot Ave, and just a short stroll to the beach, harbor, village shops, dining, library, and train to New York City, this beautifully restored 1853 Colonial was once home to Miss Augusta Smith's Seaside Seminary. The residence has been reimagined for today with warmth, elegance, and every modern comfort. Behind its gracious front porch and classic lines, over 4,300 sf unfold with light-filled rooms, hardwood floors, and three wood-burning fireplaces that invite gathering. The home offers six bedrooms, including two primary suites--one on the first floor and one upstairs--each a private retreat with spa-like baths. A country kitchen with its own fireplace, banquette dining, and French doors to the terrace becomes the heart of the home, perfect for everyday living and entertaining. Outdoors, stone walls and sweeping lawns frame a terrace where privacy abounds, and that looks over the guest cottage, playhouse, and charming red barn. The 1,100 sf cottage, complete with living room, kitchen, and bedroom suite, is ideal for visitors or extended stays. This one-of-a-kind gem of a property blends history, charm, and convenience... an opportunity to live in one of Connecticut's most cherished seaside villages!

6 Beds ⋅ 6 Baths ⋅ 24132810 MLS

Step into history in the heart of Southport Village, where this location doesn't get any better! On Pequot Ave, and just a short stroll to the beach, harbor, village shops, dining, library, and train to New York City, this beautifully restored 1853 Colonial was once home to Miss Augusta Smith's Seaside Seminary. The residence has been reimagined for today with warmth, elegance, and every modern comfort. Behind its gracious front porch and classic lines, over 4,300 sf unfold with light-filled rooms, hardwood floors, and three wood-burning fireplaces that invite gathering. The home offers six bedrooms, including two primary suites--one on the first floor and one upstairs--each a private retreat with spa-like baths. A country kitchen with its own fireplace, banquette dining, and French doors to the terrace becomes the heart of the home, perfect for everyday living and entertaining. Outdoors, stone walls and sweeping lawns frame a terrace where privacy abounds, and that looks over the guest cottage, playhouse, and charming red barn. The 1,100 sf cottage, complete with living room, kitchen, and bedroom suite, is ideal for visitors or extended stays. This one-of-a-kind gem of a property blends history, charm, and convenience... an opportunity to live in one of Connecticut's most cherished seaside villages!

944 Pequot Ave, Fairfield

$3,700,000

Gracious and storied, this 1859 antique residence is set in the heart of coveted Southport Village and offers timeless character paired with a rare, walk-to-harbor lifestyle. Cherished by the same family since 1974, the home enjoys some views of Southport Harbor and is just steps from the village center, shops, dining, train, and waterfront. The interior showcases classic period details, including multiple fireplaces, wide-plank floors, and thoughtfully integrated modern conveniences such as an elevator. The expansive living room features a fireplace and built-in bookshelves and French doors that open to a screened-in patio-an ideal setting for outdoor dining and entertaining. The home offers four bedrooms, three of which are en-suite, providing comfort and privacy for family and guests. Set on a level, usable yard, the property also includes a barn with renovation potential, offering exciting possibilities for studio, workshop, or additional living space (subject to approvals). A rare opportunity to own a distinguished Southport Village antique with harbor views, provenance, and exceptional potential. Not in Historic District.

4 Beds ⋅ 5 Baths ⋅ 24150693 MLS

Gracious and storied, this 1859 antique residence is set in the heart of coveted Southport Village and offers timeless character paired with a rare, walk-to-harbor lifestyle. Cherished by the same family since 1974, the home enjoys some views of Southport Harbor and is just steps from the village center, shops, dining, train, and waterfront. The interior showcases classic period details, including multiple fireplaces, wide-plank floors, and thoughtfully integrated modern conveniences such as an elevator. The expansive living room features a fireplace and built-in bookshelves and French doors that open to a screened-in patio-an ideal setting for outdoor dining and entertaining. The home offers four bedrooms, three of which are en-suite, providing comfort and privacy for family and guests. Set on a level, usable yard, the property also includes a barn with renovation potential, offering exciting possibilities for studio, workshop, or additional living space (subject to approvals). A rare opportunity to own a distinguished Southport Village antique with harbor views, provenance, and exceptional potential. Not in Historic District.

130 Willow St, Fairfield

$3,205,000

144 Westway Road is that once-in-a-lifetime opportunity to be a part of the desirable lifestyle that is found in Southport Village. Located on Westway Road, this home is surrounded by historic homes dating back to era of a bustling shipping harbor providing a classic New England setting. This home has been signficantly renovated over the years creating living spaces that are optimal for todays buyers; new open-concept kitchen/family room with top-of-the-line appliances, finishes, fireplace and extensive built-ins, new master bedroom addition complete with walk-in closet and spacious bath, and much more. ALL 5 bedrooms are en-suite with newly renovated bathrooms. Outdoor space creates a beautiful oasis with mature landscaping, privacy trees and an expansive tiered bluestone patio. This convenient location is steps to Southport Harbor, walk-to train, and local shops. Don't miss this opportunity to be a part of life in the "Village".

5 Beds ⋅ 6 Baths ⋅ 24149388 MLS

144 Westway Road is that once-in-a-lifetime opportunity to be a part of the desirable lifestyle that is found in Southport Village. Located on Westway Road, this home is surrounded by historic homes dating back to era of a bustling shipping harbor providing a classic New England setting. This home has been signficantly renovated over the years creating living spaces that are optimal for todays buyers; new open-concept kitchen/family room with top-of-the-line appliances, finishes, fireplace and extensive built-ins, new master bedroom addition complete with walk-in closet and spacious bath, and much more. ALL 5 bedrooms are en-suite with newly renovated bathrooms. Outdoor space creates a beautiful oasis with mature landscaping, privacy trees and an expansive tiered bluestone patio. This convenient location is steps to Southport Harbor, walk-to train, and local shops. Don't miss this opportunity to be a part of life in the "Village".

144 Westway Rd, Fairfield

$2,875,000

Welcome to this exceptional newer Colonial nestled in a highly desirable Southport location, where timeless elegance meets modern luxury. Custom built with impeccable attention to detail, this stunning home offers three expansive levels of beautifully finished living space, perfectly designed for both everyday living and entertaining. Set on 1.68 acres of lush, manicured grounds, the property provides a private, serene retreat complete with a pool and inviting patio, perfect for summer gatherings. A gracious circular driveway enhances the home's impressive curb appeal. Inside, you'll find 4-5 spacious bedrooms, 4 full baths, and 2 half baths, all thoughtfully appointed. The gourmet kitchen is a chef's dream, featuring professional-grade appliances, custom cabinetry, and refined finishes. High ceilings and elegant sconces create a warm yet sophisticated ambiance throughout the home. Exceptional craftsmanship is evident at every turn, with custom built-ins, detailed moldings, and superior construction quality defining the interiors. A whole-house generator adds peace of mind, while the quiet, picturesque street offers tranquility without sacrificing proximity to town, shopping and dining. This remarkable property seamlessly blends luxury, comfort, and convenience-truly a standout offering in Southport.

5 Beds ⋅ 6 Baths ⋅ 24162393 MLS

Welcome to this exceptional newer Colonial nestled in a highly desirable Southport location, where timeless elegance meets modern luxury. Custom built with impeccable attention to detail, this stunning home offers three expansive levels of beautifully finished living space, perfectly designed for both everyday living and entertaining. Set on 1.68 acres of lush, manicured grounds, the property provides a private, serene retreat complete with a pool and inviting patio, perfect for summer gatherings. A gracious circular driveway enhances the home's impressive curb appeal. Inside, you'll find 4-5 spacious bedrooms, 4 full baths, and 2 half baths, all thoughtfully appointed. The gourmet kitchen is a chef's dream, featuring professional-grade appliances, custom cabinetry, and refined finishes. High ceilings and elegant sconces create a warm yet sophisticated ambiance throughout the home. Exceptional craftsmanship is evident at every turn, with custom built-ins, detailed moldings, and superior construction quality defining the interiors. A whole-house generator adds peace of mind, while the quiet, picturesque street offers tranquility without sacrificing proximity to town, shopping and dining. This remarkable property seamlessly blends luxury, comfort, and convenience-truly a standout offering in Southport.

127 Field Rock Rd, Fairfield

$2,755,000

Set along a storybook private drive, where a gently winding brook passes beneath charming stone bridges, this is a home defined as much by its setting as by the way it lives. There's a quiet magic here-a sense of privacy and calm that feels rare, yet a warmth that makes it easy to imagine putting down roots and staying awhile. Inside, the home unfolds with an easy, natural flow. The spaces are generous without excess, designed for real living and the moments that shape it. The kitchen and great room come together as the heart of the home-open, inviting, and filled with light-where everyday routines and gatherings blend seamlessly. Cathedral ceilings and a wood-burning fireplace add both scale and comfort, creating a place that feels equally suited for slow mornings and full evenings. Thoughtful flexibility is woven throughout, with spaces to work, create, and grow, along with a finished lower level that adapts as life evolves. Upstairs, the primary suite offers a sense of retreat, set apart for quiet and privacy, while several additional bedrooms provide room to expand, host, and settle in. Outdoors, the property invites a slower pace. Dining on the deck, tending to a garden, or simply enjoying the open yard feels effortless, with the soft sound of the brook never far away. Here, privacy and connection coexist-tucked away in a setting that feels like its own small world, yet just minutes from town, train, and shoreline. A place to grow into, and a place to stay.

5 Beds ⋅ 5 Baths ⋅ 24166236 MLS

Set along a storybook private drive, where a gently winding brook passes beneath charming stone bridges, this is a home defined as much by its setting as by the way it lives. There's a quiet magic here-a sense of privacy and calm that feels rare, yet a warmth that makes it easy to imagine putting down roots and staying awhile. Inside, the home unfolds with an easy, natural flow. The spaces are generous without excess, designed for real living and the moments that shape it. The kitchen and great room come together as the heart of the home-open, inviting, and filled with light-where everyday routines and gatherings blend seamlessly. Cathedral ceilings and a wood-burning fireplace add both scale and comfort, creating a place that feels equally suited for slow mornings and full evenings. Thoughtful flexibility is woven throughout, with spaces to work, create, and grow, along with a finished lower level that adapts as life evolves. Upstairs, the primary suite offers a sense of retreat, set apart for quiet and privacy, while several additional bedrooms provide room to expand, host, and settle in. Outdoors, the property invites a slower pace. Dining on the deck, tending to a garden, or simply enjoying the open yard feels effortless, with the soft sound of the brook never far away. Here, privacy and connection coexist-tucked away in a setting that feels like its own small world, yet just minutes from town, train, and shoreline. A place to grow into, and a place to stay.

790 Cedar Brook Ln, Fairfield

$2,730,000

Nestled on a picturesque cul-de-sac street in the heart of Southport, 70 Meadow Ridge Rd offers the perfect blend of classic charm and modern convenience. This custom home boasts 6 bedrooms and 5, Bathrooms providing ample space for comfortable living and entertaining. Step inside to discover sun-drenched living spaces featuring gleaming hardwood floors, a cozy fireplace, and an open-concept layout that seamlessly connects the kitchen, dining, and living areas. The chef's kitchen is a dream come true, complete with high-end appliances, quartz countertops, and a spacious island perfect for casual meals or hosting gatherings. The primary suite on both the first and second floors each featuring a spa-like ensuite bathroom and generous closet space. Outside, the meticulously landscaped yard offers a private oasis with a patio, spectacular gunite pool with hot tub, ideal for summer barbecues or quiet mornings with coffee. Located in one of Southport's most desirable neighborhoods, this home is just minutes from the vibrant downtown area, with its charming boutiques, award-winning restaurants, beaches and scenic harbor. Commuters will appreciate the proximity to Metro-North and major highways, while beach lovers will adore being so close to the shores of Long Island Sound. Whether you're looking for a forever home or a weekend retreat, 70 Meadow Ridge Rd delivers the lifestyle you've been dreaming of. Don't miss the opportunity to make it yours!

6 Beds ⋅ 6 Baths ⋅ 24156627 MLS

Nestled on a picturesque cul-de-sac street in the heart of Southport, 70 Meadow Ridge Rd offers the perfect blend of classic charm and modern convenience. This custom home boasts 6 bedrooms and 5, Bathrooms providing ample space for comfortable living and entertaining. Step inside to discover sun-drenched living spaces featuring gleaming hardwood floors, a cozy fireplace, and an open-concept layout that seamlessly connects the kitchen, dining, and living areas. The chef's kitchen is a dream come true, complete with high-end appliances, quartz countertops, and a spacious island perfect for casual meals or hosting gatherings. The primary suite on both the first and second floors each featuring a spa-like ensuite bathroom and generous closet space. Outside, the meticulously landscaped yard offers a private oasis with a patio, spectacular gunite pool with hot tub, ideal for summer barbecues or quiet mornings with coffee. Located in one of Southport's most desirable neighborhoods, this home is just minutes from the vibrant downtown area, with its charming boutiques, award-winning restaurants, beaches and scenic harbor. Commuters will appreciate the proximity to Metro-North and major highways, while beach lovers will adore being so close to the shores of Long Island Sound. Whether you're looking for a forever home or a weekend retreat, 70 Meadow Ridge Rd delivers the lifestyle you've been dreaming of. Don't miss the opportunity to make it yours!

70 Meadow Ridge Rd, Fairfield

$2,700,000

Gracious Southport Village/Southport Harbor 3Bedroom, 2 1/2Bath Colonial Home, with Water & 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 & Southport Beaches!

3 Beds ⋅ 3 Baths ⋅ 24179343 MLS

Gracious Southport Village/Southport Harbor 3Bedroom, 2 1/2Bath Colonial Home, with Water & 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 & Southport Beaches!

28 Center St, Fairfield

$2,699,000

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.

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

$2,625,000

Set on a crescent shaped quiet street with serene seasonal water views, this stunning 2023 built home offers the perfect blend of modern elegance and comfortable living. Featuring four spacious bedrooms, 4 1/2 baths, every detail has been thoughtfully designed for both style and functionality. This beautifully designed open floor plan offers an impressive chef-inspired kitchen with white quartz countertops that effortlessly flows into a spacious living room, creating the perfect environment for both every day living and entertainment. A tastefully appointed dining room, with a custom glass wine cellar by Wine Square. The primary bedroom suite feels like a private retreat, defined by its soaring vaulted ceilings and striking exposed wood beams that add warmth and architectural interest. The suite extends seamlessly into a spacious walk-in closet and an adjoining luxury bath that features a soaking tub, oversized glass shower, and dual vanities. The expansive basement provides incredible versatility, complete with a dedicated cinema room for the ultimate movie night experience. Situated on a meticulously landscaped 1 acre property, the home offers both privacy and space to enjoy. An inviting outdoor entertainment space, ideal for gatherings or quiet evenings, with ample room to add a pool. Finished 3 car garage. This is modern living at its finest; elegant, spacious and designed for both relaxation and entertainment. Close to town, beaches and train. Your dream home awaits!

4 Beds ⋅ 5 Baths ⋅ 24166637 MLS

Set on a crescent shaped quiet street with serene seasonal water views, this stunning 2023 built home offers the perfect blend of modern elegance and comfortable living. Featuring four spacious bedrooms, 4 1/2 baths, every detail has been thoughtfully designed for both style and functionality. This beautifully designed open floor plan offers an impressive chef-inspired kitchen with white quartz countertops that effortlessly flows into a spacious living room, creating the perfect environment for both every day living and entertainment. A tastefully appointed dining room, with a custom glass wine cellar by Wine Square. The primary bedroom suite feels like a private retreat, defined by its soaring vaulted ceilings and striking exposed wood beams that add warmth and architectural interest. The suite extends seamlessly into a spacious walk-in closet and an adjoining luxury bath that features a soaking tub, oversized glass shower, and dual vanities. The expansive basement provides incredible versatility, complete with a dedicated cinema room for the ultimate movie night experience. Situated on a meticulously landscaped 1 acre property, the home offers both privacy and space to enjoy. An inviting outdoor entertainment space, ideal for gatherings or quiet evenings, with ample room to add a pool. Finished 3 car garage. This is modern living at its finest; elegant, spacious and designed for both relaxation and entertainment. Close to town, beaches and train. Your dream home awaits!

177 High Meadow Rd, Fairfield

$2,505,000

Stunning in Southport! Nestled in a sought-after enclave of quiet streets and cul-de-sacs, lined with blooming Dogwood trees, this beautifully renovated 4 bed, 4.5 bath Colonial is ready to be enjoyed! The dream kitchen boasts a massive island, top of the line appliances, and a large sunny eating area with sliders to the deck! The open kitchen flows to the airy family room, living room and sunroom for gathering and play. Sunny formal dining room, dedicated office with deck access, a powder room, and the smartly designed mudroom round out the gracious first floor. Upstairs, the oversized primary suite features a cathedral ceiling, walk-in closets, and fully renovated cathedral ceiling spa ensuite, with double vanities and soaking tub. Three additional light-filled bedrooms upstairs, one with ensuite, and two share the hall bath. The gorgeous walk out LL has a spacious rec room, gym area, full bath, and ample storage. The fully private back deck is ready for grilling and enjoying the large backyard. Immaculately renovated kitchen and baths, refinished floors and paint, new indoor & outdoor lighting and more. Near Southport and Fairfield shopping, dining, beaches and town amenities!

4 Beds ⋅ 5 Baths ⋅ 24172901 MLS

Stunning in Southport! Nestled in a sought-after enclave of quiet streets and cul-de-sacs, lined with blooming Dogwood trees, this beautifully renovated 4 bed, 4.5 bath Colonial is ready to be enjoyed! The dream kitchen boasts a massive island, top of the line appliances, and a large sunny eating area with sliders to the deck! The open kitchen flows to the airy family room, living room and sunroom for gathering and play. Sunny formal dining room, dedicated office with deck access, a powder room, and the smartly designed mudroom round out the gracious first floor. Upstairs, the oversized primary suite features a cathedral ceiling, walk-in closets, and fully renovated cathedral ceiling spa ensuite, with double vanities and soaking tub. Three additional light-filled bedrooms upstairs, one with ensuite, and two share the hall bath. The gorgeous walk out LL has a spacious rec room, gym area, full bath, and ample storage. The fully private back deck is ready for grilling and enjoying the large backyard. Immaculately renovated kitchen and baths, refinished floors and paint, new indoor & outdoor lighting and more. Near Southport and Fairfield shopping, dining, beaches and town amenities!

276 Flintlock Rd, Fairfield

$2,450,000

Discover refined waterfront living at 400 Bronson Road. A beautifully crafted custom colonial set along the peaceful Mill River in Southport. This elegant waterfront home offers five generously sized bedrooms, four and a half bathrooms, and over 4,000 square feet of thoughtfully designed space across four levels. High-end finishes and timeless design details shine throughout, from the white oak accents and grand glass-railed foyer to the chef's kitchen featuring quartz countertops and premium appliances. The open layout is ideal for both everyday living and entertaining, featuring the floor to ceiling glass enclosed wine room and multiple balconies, inviting you to relax and take in the scenic river views. The luxurious primary suite offers a private retreat complete with a spa-like bathroom and its own balcony overlooking the water. Perfectly positioned just minutes from Southport's beaches, golf courses, vibrant shops and restaurants, this home blends sophistication and comfort, and natural beauty in one of Fairfield's most sought-after locations.

5 Beds ⋅ 5 Baths ⋅ 24124894 MLS

Discover refined waterfront living at 400 Bronson Road. A beautifully crafted custom colonial set along the peaceful Mill River in Southport. This elegant waterfront home offers five generously sized bedrooms, four and a half bathrooms, and over 4,000 square feet of thoughtfully designed space across four levels. High-end finishes and timeless design details shine throughout, from the white oak accents and grand glass-railed foyer to the chef's kitchen featuring quartz countertops and premium appliances. The open layout is ideal for both everyday living and entertaining, featuring the floor to ceiling glass enclosed wine room and multiple balconies, inviting you to relax and take in the scenic river views. The luxurious primary suite offers a private retreat complete with a spa-like bathroom and its own balcony overlooking the water. Perfectly positioned just minutes from Southport's beaches, golf courses, vibrant shops and restaurants, this home blends sophistication and comfort, and natural beauty in one of Fairfield's most sought-after locations.

400 Bronson Rd, Fairfield

$2,400,000

260 Range Road is a home that feels instantly timeless. An elegant Connecticut Colonial w/stately, time-softened brick exterior, set back at the end of a quiet cul-de-sac in one of Southport's most coveted neighborhoods. Peaceful & private yet minutes to downtown Fairfield, Westport, Metro North & everyday conveniences this home offers both serenity & connection. In a neighborhood where neighbors still ride bikes in the street, the home offers a rare sense of calm & community. Inside, soaring ceilings, oversized windows & abundant natural light define the interiors. Each room is generously proportioned w/9-foot ceilings & classic craftsmanship throughout. The main level balances elegance & comfort w/formal living & dining rooms, a handsome office & dramatic great room w/soaring double-height ceilings & wood-burning fireplace. The kitchen is both refined & inviting, featuring rich stone countertops, premium appliances, center island, sunny breakfast area w/door to expansive bluestone patio. Upstairs the primary suite offers a true retreat w/sitting area, office/nursery, 3 walk-in closets & en-suite bath. 3 additional bedrooms are generously sized, offering comfort & flexibility for family & guests. The finished walk-out lower level adds exceptional versatility w/space for a playroom, gym, media room or guest room all leading to a gorgeous flat lawn and backyard oasis. Laundry room, attached 3-car garage, abundant storage, gas, sewer. A rare Southport offering.

4 Beds ⋅ 4 Baths ⋅ 24161505 MLS

260 Range Road is a home that feels instantly timeless. An elegant Connecticut Colonial w/stately, time-softened brick exterior, set back at the end of a quiet cul-de-sac in one of Southport's most coveted neighborhoods. Peaceful & private yet minutes to downtown Fairfield, Westport, Metro North & everyday conveniences this home offers both serenity & connection. In a neighborhood where neighbors still ride bikes in the street, the home offers a rare sense of calm & community. Inside, soaring ceilings, oversized windows & abundant natural light define the interiors. Each room is generously proportioned w/9-foot ceilings & classic craftsmanship throughout. The main level balances elegance & comfort w/formal living & dining rooms, a handsome office & dramatic great room w/soaring double-height ceilings & wood-burning fireplace. The kitchen is both refined & inviting, featuring rich stone countertops, premium appliances, center island, sunny breakfast area w/door to expansive bluestone patio. Upstairs the primary suite offers a true retreat w/sitting area, office/nursery, 3 walk-in closets & en-suite bath. 3 additional bedrooms are generously sized, offering comfort & flexibility for family & guests. The finished walk-out lower level adds exceptional versatility w/space for a playroom, gym, media room or guest room all leading to a gorgeous flat lawn and backyard oasis. Laundry room, attached 3-car garage, abundant storage, gas, sewer. A rare Southport offering.

260 Range Rd, Fairfield

$2,210,000

Location, space and timeless design come together in this beautiful 5 Bedroom Colonial set on 1.48 acres in one of Southport's most desirable neighborhoods. This home offers the ideal balance of privacy and convenience. hardwood floors, custom moldings, and a coffered ceiling highlight the inviting main level. The Family Room with 9-foot ceilings and a gas fireplace opens to the Eat-In-Kitchen featuring a large center island, granite countertops, and stainless steel appliances - ideal for everyday living and entertaining. A formal Dining Room with raised paneling and a gracious Living Room with fireplace create elegant gathering spaces. Upstairs, the Primary Bedroom Suite offers cathedral ceiling, gas fireplace, Dressing Room, Full Bath. Four additional Bedrooms, Hall Bath and convenient 2nd floor Laundry complete the upper level. The screened porch overlooks a private backyard, perfect for relaxing or entertaining. A rare Southport Gem!

5 Beds ⋅ 3 Baths ⋅ 24160667 MLS

Location, space and timeless design come together in this beautiful 5 Bedroom Colonial set on 1.48 acres in one of Southport's most desirable neighborhoods. This home offers the ideal balance of privacy and convenience. hardwood floors, custom moldings, and a coffered ceiling highlight the inviting main level. The Family Room with 9-foot ceilings and a gas fireplace opens to the Eat-In-Kitchen featuring a large center island, granite countertops, and stainless steel appliances - ideal for everyday living and entertaining. A formal Dining Room with raised paneling and a gracious Living Room with fireplace create elegant gathering spaces. Upstairs, the Primary Bedroom Suite offers cathedral ceiling, gas fireplace, Dressing Room, Full Bath. Four additional Bedrooms, Hall Bath and convenient 2nd floor Laundry complete the upper level. The screened porch overlooks a private backyard, perfect for relaxing or entertaining. A rare Southport Gem!

320 Warner Hill Rd, Fairfield

$2,200,000

Welcome to 99 Acorn Lane, a desirable Southport address set on a quiet cul-de-sac just minutes to Westport, Southport Village, and Downtown Fairfield. This expanded Cape sits on 1.24 beautiful acres, offering privacy within a charming neighborhood and ample opportunity for expansion or a pool, subject to approvals. Thoughtfully upgraded, the home offers more than 3,000 square feet of flexible living space with 4 bedrooms, 3.5 baths, 2 fireplaces, and hardwood floors through most of the house. The main level is the heart of the home, with an inviting open layout, soaring ceilings, and an eat-in kitchen overlooking two spacious living areas with fireplaces. A pretty dining room, with oversized windows, is currently used as a study. A first-floor primary suite features a walk-in closet and full bath, while the second floor includes two additional bedrooms and a shared bath. Above the garage, a bonus bedroom with full bath offers flexible space for guests or work. A screened porch overlooks the property for enjoying warmer months. At the cul-de-sac, Aspetuck Land Trust's Acorn Lane Upland Preserve offers wooded trails connecting to Fairfield's Mill Hill Open Space. A rare Southport opportunity with space, charm, and convenience.

4 Beds ⋅ 4 Baths ⋅ 24160414 MLS

Welcome to 99 Acorn Lane, a desirable Southport address set on a quiet cul-de-sac just minutes to Westport, Southport Village, and Downtown Fairfield. This expanded Cape sits on 1.24 beautiful acres, offering privacy within a charming neighborhood and ample opportunity for expansion or a pool, subject to approvals. Thoughtfully upgraded, the home offers more than 3,000 square feet of flexible living space with 4 bedrooms, 3.5 baths, 2 fireplaces, and hardwood floors through most of the house. The main level is the heart of the home, with an inviting open layout, soaring ceilings, and an eat-in kitchen overlooking two spacious living areas with fireplaces. A pretty dining room, with oversized windows, is currently used as a study. A first-floor primary suite features a walk-in closet and full bath, while the second floor includes two additional bedrooms and a shared bath. Above the garage, a bonus bedroom with full bath offers flexible space for guests or work. A screened porch overlooks the property for enjoying warmer months. At the cul-de-sac, Aspetuck Land Trust's Acorn Lane Upland Preserve offers wooded trails connecting to Fairfield's Mill Hill Open Space. A rare Southport opportunity with space, charm, and convenience.

99 Acorn Ln, Fairfield

$2,150,000

Enjoy the summer at 161 Sherwood Drive, a beautifully expanded and extensively updated residence located in the desirable Southport neighborhood. Offering approximately 3,679 square feet of thoughtfully designed living space, this home blends comfort, functionality, and inviting indoor-outdoor living in a private setting. The home features 4 spacious bedrooms, 4 full baths, and 1 half bath, including a sought-after first-floor primary bedroom suite that provides convenience and flexibility. The impressive great room serves as a standout feature, complete with a mahogany bar, stone fireplace, mounted TV area, and ample room for billiards and table games-creating an ideal setting for relaxing or hosting guests year-round. Designed for both everyday living and entertaining, the home showcases expansive gathering spaces filled with natural light. The screened-in porch extends the living space outdoors and provides a comfortable place to enjoy the surrounding private yard in multiple seasons. Outside, the in-ground pool and landscaped grounds create a peaceful retreat with space for entertaining, recreation, and outdoor dining. **962 sqft is the finished walk out lower level and included in total sqft.**

4 Beds ⋅ 5 Baths ⋅ 24178764 MLS

Enjoy the summer at 161 Sherwood Drive, a beautifully expanded and extensively updated residence located in the desirable Southport neighborhood. Offering approximately 3,679 square feet of thoughtfully designed living space, this home blends comfort, functionality, and inviting indoor-outdoor living in a private setting. The home features 4 spacious bedrooms, 4 full baths, and 1 half bath, including a sought-after first-floor primary bedroom suite that provides convenience and flexibility. The impressive great room serves as a standout feature, complete with a mahogany bar, stone fireplace, mounted TV area, and ample room for billiards and table games-creating an ideal setting for relaxing or hosting guests year-round. Designed for both everyday living and entertaining, the home showcases expansive gathering spaces filled with natural light. The screened-in porch extends the living space outdoors and provides a comfortable place to enjoy the surrounding private yard in multiple seasons. Outside, the in-ground pool and landscaped grounds create a peaceful retreat with space for entertaining, recreation, and outdoor dining. **962 sqft is the finished walk out lower level and included in total sqft.**

161 Sherwood Dr, Fairfield

$1,925,000

Welcome to Village at Southport, a 16-home gated enclave of luxurious, turn-key homes right in "The Village." Pure easy living in this 3800+ square foot, three level townhome with every amenity desired. Just a few minutes to the gorgeous beach & harbor, library, restaurants & shops, ideally located close to commute & downtown living, yet quiet & private. This end unit is ideally set abutting the 6-acres of open space, with a secluded backyard amidst the 11-acre property. Enter the main level to a versatile space that can be utilized as an office, great room, bedroom, flex space with a full bathroom, outdoor patio access & mudroom, with entry to the 2-car garage. On the main level, enjoy an open concept, with a gas-fireplaced living room with beautiful built-ins & coffered ceilings, a sizable dining room open to the high-end kitchen & oversized Quartz island with seating. The bright, white kitchen features a Sub-Zero & Viking with dishwasher, microwave & pantry with access to the back deck, half-bath & private office. The upper level boasts an enviable primary suite with huge walk-in closet & lavish en-suite bath with walk-in shower & double sinks topped with Quartz. The laundry room features storage, hanging racks & a sink for convenience. Completing this level is a Jack-and-Jill bathroom connecting two guest rooms, both with walk-in closets. Elevator ready! Just think of how lovely of a way of life, enjoying one of the most desirable & beautiful spots in Fairfield County.

3 Beds ⋅ 4 Baths ⋅ 24150618 MLS ⋅ Village At Southport BLDG.

Welcome to Village at Southport, a 16-home gated enclave of luxurious, turn-key homes right in "The Village." Pure easy living in this 3800+ square foot, three level townhome with every amenity desired. Just a few minutes to the gorgeous beach & harbor, library, restaurants & shops, ideally located close to commute & downtown living, yet quiet & private. This end unit is ideally set abutting the 6-acres of open space, with a secluded backyard amidst the 11-acre property. Enter the main level to a versatile space that can be utilized as an office, great room, bedroom, flex space with a full bathroom, outdoor patio access & mudroom, with entry to the 2-car garage. On the main level, enjoy an open concept, with a gas-fireplaced living room with beautiful built-ins & coffered ceilings, a sizable dining room open to the high-end kitchen & oversized Quartz island with seating. The bright, white kitchen features a Sub-Zero & Viking with dishwasher, microwave & pantry with access to the back deck, half-bath & private office. The upper level boasts an enviable primary suite with huge walk-in closet & lavish en-suite bath with walk-in shower & double sinks topped with Quartz. The laundry room features storage, hanging racks & a sink for convenience. Completing this level is a Jack-and-Jill bathroom connecting two guest rooms, both with walk-in closets. Elevator ready! Just think of how lovely of a way of life, enjoying one of the most desirable & beautiful spots in Fairfield County.

485 Westway Rd Unit 485, Fairfield

$1,913,022

Unbeatable location! A Southport classic awaits at the end of a quiet Cul de sac set on the most stunning & special 1+ acre lot - Welcome home to 147 Carriage Drive. This pristine, move-in-ready Colonial lives large & offers so much. Lovingly owned & featuring numerous key updates that will ensure maintenance free living include a newer furnace & roof, recent connection to town sewer, fresh exterior paint, new sunroom windows & sliders & professionally designed landscaping. The function, flow & privacy are ideal in this thoughtfully designed main level w/ multiple versatile living spaces - one of the homeowners' favorite things to love about this home.The living room w/ a cozy fireplace flows easily into the dining room & eat-in kitchen. In addition, there is both a spacious family room & a den to relax & enjoy + an all-season sunroom filled w/ natural light that opens to the exterior deck. Upstairs, you will find 4 generously sized bedrooms, including an expansive primary suite, all conveniently located on the same level. The unfinished lower level presents a fantastic opportunity for future expansion, whether you envision a gym, media room or additional living space or just need great storage. Once outside a private yard filled w/ colorful flowering trees & open space await. Ideally located w/in walking distance to the elementary school & local ball fields & just minutes from Southport Harbor, the train, dining & shopping while remaining so private. A rare Southport find!

4 Beds ⋅ 3 Baths ⋅ 24169137 MLS

Unbeatable location! A Southport classic awaits at the end of a quiet Cul de sac set on the most stunning & special 1+ acre lot - Welcome home to 147 Carriage Drive. This pristine, move-in-ready Colonial lives large & offers so much. Lovingly owned & featuring numerous key updates that will ensure maintenance free living include a newer furnace & roof, recent connection to town sewer, fresh exterior paint, new sunroom windows & sliders & professionally designed landscaping. The function, flow & privacy are ideal in this thoughtfully designed main level w/ multiple versatile living spaces - one of the homeowners' favorite things to love about this home.The living room w/ a cozy fireplace flows easily into the dining room & eat-in kitchen. In addition, there is both a spacious family room & a den to relax & enjoy + an all-season sunroom filled w/ natural light that opens to the exterior deck. Upstairs, you will find 4 generously sized bedrooms, including an expansive primary suite, all conveniently located on the same level. The unfinished lower level presents a fantastic opportunity for future expansion, whether you envision a gym, media room or additional living space or just need great storage. Once outside a private yard filled w/ colorful flowering trees & open space await. Ideally located w/in walking distance to the elementary school & local ball fields & just minutes from Southport Harbor, the train, dining & shopping while remaining so private. A rare Southport find!

147 Carriage Dr, Fairfield

$1,905,000

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 country kitchen, complete with dining area, opens seamlessly to expansive decking and a stunning circular brick terrace designed for effortless indoor-outdoor living and al fresco dining. The exquisite main staircase ascends to to second floor, offering four well-proportioned bedrooms, a cozy and versatile office or den, and convenient laundry area. Additionally, the "secret staircase" reveals a spectacular rooftop cupola, where arched windows frame sweeping 360-degree Village views.

4 Beds ⋅ 3 Baths ⋅ 24183260 MLS

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 country kitchen, complete with dining area, opens seamlessly to expansive decking and a stunning circular brick terrace designed for effortless indoor-outdoor living and al fresco dining. The exquisite main staircase ascends to to second floor, offering four well-proportioned bedrooms, a cozy and versatile office or den, and convenient laundry area. Additionally, the "secret staircase" reveals a spectacular rooftop cupola, where arched windows frame sweeping 360-degree Village views.

26 Spruce St, Fairfield

$1,885,000

Enjoy the privacy of a stand-alone home with the effortless convenience of condominium living in coveted Southport Green. One of only two detached residences in this desirable 24-home community, the three-level property offers three bedrooms, three renovated full baths, a powder room, and an attached two-car garage. A private patio-an uncommon amenity within the enclave-provides a peaceful setting for outdoor dining and entertaining. Ideally suited for downsizers, commuters, or those seeking an easy lock-and-leave lifestyle, it is just moments from Southport Village, Metro-North, the Delamar, Gray Goose Tavern, Equinox, and all the conveniences that make this location so appealing.

3 Beds ⋅ 4 Baths ⋅ 24195971 MLS ⋅ Southport Green BLDG.

Enjoy the privacy of a stand-alone home with the effortless convenience of condominium living in coveted Southport Green. One of only two detached residences in this desirable 24-home community, the three-level property offers three bedrooms, three renovated full baths, a powder room, and an attached two-car garage. A private patio-an uncommon amenity within the enclave-provides a peaceful setting for outdoor dining and entertaining. Ideally suited for downsizers, commuters, or those seeking an easy lock-and-leave lifestyle, it is just moments from Southport Village, Metro-North, the Delamar, Gray Goose Tavern, Equinox, and all the conveniences that make this location so appealing.

2 Elmwood Dr Unit 2, Fairfield

$1,840,000

Situated on 2 manicured acres in Southport and surrounded by multi-million-dollar estates, this gated, European-inspired country home blends timeless charm with modern elegance. A white-pebble drive, stone walls, and sweeping lawns with mature trees create a private estate feel. Inside, the home balances warmth with sophistication. Offering 3 bedrooms on the main level and a 4th bedroom option in the lower level with full bath ensuite. Hand-hewn beams, slate entry, and a fieldstone fireplace pair seamlessly with crisp white walls, bold black accents, and striking designer lighting. The open yet defined layout features multiple entertaining areas, a sleek eat-in kitchen, and beautifully renovated baths. More than a home, this is an experience-an extraordinary Southport estate where modern luxury, historic charm, and a setting of rare beauty come together.

3 Beds ⋅ 4 Baths ⋅ 24123202 MLS

Situated on 2 manicured acres in Southport and surrounded by multi-million-dollar estates, this gated, European-inspired country home blends timeless charm with modern elegance. A white-pebble drive, stone walls, and sweeping lawns with mature trees create a private estate feel. Inside, the home balances warmth with sophistication. Offering 3 bedrooms on the main level and a 4th bedroom option in the lower level with full bath ensuite. Hand-hewn beams, slate entry, and a fieldstone fireplace pair seamlessly with crisp white walls, bold black accents, and striking designer lighting. The open yet defined layout features multiple entertaining areas, a sleek eat-in kitchen, and beautifully renovated baths. More than a home, this is an experience-an extraordinary Southport estate where modern luxury, historic charm, and a setting of rare beauty come together.

1001 Hulls Farm Rd, Fairfield

$1,812,500

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.

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

$1,750,000

Set along one of Southport's most picturesque residential cul-de-sac's, 264 Half Mile Road embodies the quiet sophistication and understated elegance that define this coveted coastal enclave. Privately sited on just over an acre, this classic Colonial residence offers a rare blend of space, serenity, and enduring charm in a setting known for its natural beauty and refined lifestyle. With approximately 2,900 square feet of living space, the home is thoughtfully scaled with four bedrooms and two and a half baths, creating a layout that is both functional and inviting. Built in the early 1970s, its architecture reflects timeless New England character-graceful proportions, warm wood elements, and a sense of quiet permanence. Mature trees, open lawn, and the gentle rhythm of the surrounding landscape create a private, park-like atmosphere-ideal for outdoor entertaining, future enhancements, or simply enjoying the tranquility that defines life on Half Mile Road. Located just minutes from Southport Village, residents enjoy effortless access to shopping, harbor views, beaches, and the Metro-North Railroad for a seamless connection to Manhattan. The neighborhood itself is celebrated for its peaceful, established feel, beautifully maintained homes, and a strong sense of community. Seller will review all offers on Tuesday, May 5th. Please submit all offers by 5:00 PM on Monday, May 4th. Seller reserves the right to accept an offer before this time."

4 Beds ⋅ 3 Baths ⋅ 24162941 MLS

Set along one of Southport's most picturesque residential cul-de-sac's, 264 Half Mile Road embodies the quiet sophistication and understated elegance that define this coveted coastal enclave. Privately sited on just over an acre, this classic Colonial residence offers a rare blend of space, serenity, and enduring charm in a setting known for its natural beauty and refined lifestyle. With approximately 2,900 square feet of living space, the home is thoughtfully scaled with four bedrooms and two and a half baths, creating a layout that is both functional and inviting. Built in the early 1970s, its architecture reflects timeless New England character-graceful proportions, warm wood elements, and a sense of quiet permanence. Mature trees, open lawn, and the gentle rhythm of the surrounding landscape create a private, park-like atmosphere-ideal for outdoor entertaining, future enhancements, or simply enjoying the tranquility that defines life on Half Mile Road. Located just minutes from Southport Village, residents enjoy effortless access to shopping, harbor views, beaches, and the Metro-North Railroad for a seamless connection to Manhattan. The neighborhood itself is celebrated for its peaceful, established feel, beautifully maintained homes, and a strong sense of community. Seller will review all offers on Tuesday, May 5th. Please submit all offers by 5:00 PM on Monday, May 4th. Seller reserves the right to accept an offer before this time."

264 Half Mile Rd, Fairfield

$1,750,000

Charming Pied-a-terre in Connecticut's alluring Southport Village! Whether you're looking for a permanent residence or your home away from home, this is a perfect vacation home or condo alternative. Leave without a care or immerse yourself in this historic maritime enclave. A rare find in the heart of the Village, this home is steps from the neighborhood eateries, shops, metro, pub, bakery, post office, Equinox, Southport Harbor, and Southport Beach. -All an hour from NYC! Cherished outdoor spaces are part of what makes this home so special. From the covered front porch, to the hidden garden terrace beneath, and the enchanting rear stone patio among lush gardens, there's always a picturesque and private retreat to enjoy. Inside, elegant interiors unfold. An inviting Living Room with hardwood floors, hidden TV, and a gas fireplace opens to the Dining Area. The renovated Chef's Kitchen features a Caesarstone island, stainless appliances, and a light-filled eating area with built-ins and a banquette overlooking the garden. Upstairs, is a serene Primary Suite and stunning spa bath, hardwood floors, and 9-foot ceiling. A Guest Bedroom, hall bath, laundry, and access to Attic Storage complete the 2nd floor. The Walk-out Lower Level offers another charming room with a second gas fireplace. It connects to a project area with a porcelain sink, storage, & separate entrance, offering guest-suite potential. Character, convenience, and privacy in a cherished seaside village!

2 Beds ⋅ 3 Baths ⋅ 24158567 MLS

Charming Pied-a-terre in Connecticut's alluring Southport Village! Whether you're looking for a permanent residence or your home away from home, this is a perfect vacation home or condo alternative. Leave without a care or immerse yourself in this historic maritime enclave. A rare find in the heart of the Village, this home is steps from the neighborhood eateries, shops, metro, pub, bakery, post office, Equinox, Southport Harbor, and Southport Beach. -All an hour from NYC! Cherished outdoor spaces are part of what makes this home so special. From the covered front porch, to the hidden garden terrace beneath, and the enchanting rear stone patio among lush gardens, there's always a picturesque and private retreat to enjoy. Inside, elegant interiors unfold. An inviting Living Room with hardwood floors, hidden TV, and a gas fireplace opens to the Dining Area. The renovated Chef's Kitchen features a Caesarstone island, stainless appliances, and a light-filled eating area with built-ins and a banquette overlooking the garden. Upstairs, is a serene Primary Suite and stunning spa bath, hardwood floors, and 9-foot ceiling. A Guest Bedroom, hall bath, laundry, and access to Attic Storage complete the 2nd floor. The Walk-out Lower Level offers another charming room with a second gas fireplace. It connects to a project area with a porcelain sink, storage, & separate entrance, offering guest-suite potential. Character, convenience, and privacy in a cherished seaside village!

494 Pequot Ave, Fairfield

$1,700,000

Nestled along the picturesque Connecticut coastline, 127 South Gate Lane places you in the heart of Southport's Harbor & Beach area-a storybook setting where classic New England charm meets coastal elegance. Imagine a historic harbor adorned with graceful sailboats gliding on tranquil waters, framed by stately colonial homes and streets shaded by towering trees. It's the kind of place where every stroll feels like stepping into a postcard. Stroll to Southport's charming boutiques, sip coffee at a cozy cafe, or savor a meal crafted from the finest local ingredients at one of the celebrated restaurants nearby. At first glance, you may see a traditional colonial, but this is not just a classic home; it's located in one of the most sought-after areas of Connecticut. Just a short walk to the Beach and Southport Harbor shops & restaurants, the Equinox health club, Pequot Yacht Club, and Metro North Train Station to NYC. This lovely classic center hall colonial features 4 bedrooms, 2.5 bathrooms, a spacious living room with great symmetry and a wood burning fireplace, large dining room with wet bar and built ins, family room with built ins, first floor laundry & mudroom room, eat in kitchen with new appliances, refinished light hardwood floors, a large two car garage, and a lovely porch with screens and glass for three season enjoyment. Sited on a cul-de-sac with significant homes, move right in or renovate when you are ready. Serviced by natural gas & city water.

4 Beds ⋅ 3 Baths ⋅ 24160009 MLS

Nestled along the picturesque Connecticut coastline, 127 South Gate Lane places you in the heart of Southport's Harbor & Beach area-a storybook setting where classic New England charm meets coastal elegance. Imagine a historic harbor adorned with graceful sailboats gliding on tranquil waters, framed by stately colonial homes and streets shaded by towering trees. It's the kind of place where every stroll feels like stepping into a postcard. Stroll to Southport's charming boutiques, sip coffee at a cozy cafe, or savor a meal crafted from the finest local ingredients at one of the celebrated restaurants nearby. At first glance, you may see a traditional colonial, but this is not just a classic home; it's located in one of the most sought-after areas of Connecticut. Just a short walk to the Beach and Southport Harbor shops & restaurants, the Equinox health club, Pequot Yacht Club, and Metro North Train Station to NYC. This lovely classic center hall colonial features 4 bedrooms, 2.5 bathrooms, a spacious living room with great symmetry and a wood burning fireplace, large dining room with wet bar and built ins, family room with built ins, first floor laundry & mudroom room, eat in kitchen with new appliances, refinished light hardwood floors, a large two car garage, and a lovely porch with screens and glass for three season enjoyment. Sited on a cul-de-sac with significant homes, move right in or renovate when you are ready. Serviced by natural gas & city water.

127 S Gate Ln, Fairfield

$1,675,000

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 & 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 to the Harbor, embrace the many interesting, legendary homes with beautifully mature landscaping. Sasco Beach provides a glorious setting as does, the Country Club of Fairfield's scenic golf course. Stately Southport Harbor is a true New England treasure! A stone's throw to I-95 and Fairfield's other beaches, enjoyable shopping and exciting dining.

2 Beds ⋅ 3 Baths ⋅ 24186343 MLS ⋅ Southport Green BLDG.

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 & 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 to the Harbor, embrace the many interesting, legendary homes with beautifully mature landscaping. Sasco Beach provides a glorious setting as does, the Country Club of Fairfield's scenic golf course. Stately Southport Harbor is a true New England treasure! A stone's throw to I-95 and Fairfield's other beaches, enjoyable shopping and exciting dining.

44 Elmwood Dr Unit 44, Fairfield

$1,600,000

Expanded and renovated Cape in a coveted Southport location on a quiet cul de sac. 230 Barberry Road offers a flexible floor plan with up to 5 bedrooms and 3 full baths, with beautifully updated living space designed for today's lifestyle. The inviting living room features a wood burning fireplace, while the spacious family room offers a gas fireplace for relaxed everyday living. The eat in kitchen opens easily to the main living areas, creating a warm and functional flow for both daily life and entertaining. Thoughtful expansion and improvements over the years add versatility and comfort, with room for guests, home office space, or multigenerational living. Set on a lovely neighborhood property in a sought after Southport setting, this home combines charm, convenience, and modern updates in one desirable package. A rare opportunity to own an expanded home in a prime cul de sac location close to town, train, shopping, and beaches.

4 Beds ⋅ 3 Baths ⋅ 24159552 MLS

Expanded and renovated Cape in a coveted Southport location on a quiet cul de sac. 230 Barberry Road offers a flexible floor plan with up to 5 bedrooms and 3 full baths, with beautifully updated living space designed for today's lifestyle. The inviting living room features a wood burning fireplace, while the spacious family room offers a gas fireplace for relaxed everyday living. The eat in kitchen opens easily to the main living areas, creating a warm and functional flow for both daily life and entertaining. Thoughtful expansion and improvements over the years add versatility and comfort, with room for guests, home office space, or multigenerational living. Set on a lovely neighborhood property in a sought after Southport setting, this home combines charm, convenience, and modern updates in one desirable package. A rare opportunity to own an expanded home in a prime cul de sac location close to town, train, shopping, and beaches.

230 Barberry Rd, Fairfield

$1,550,000

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 dining, entertaining, or simply relaxing in a private, picturesque setting. Located within walking distance to Mill Hill School, the train, Southport Village, dining, and the harbor, this is a rare opportunity to own a quintessential Fairfield home.

3 Beds ⋅ 3 Baths ⋅ 24170660 MLS

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 dining, entertaining, or simply relaxing in a private, picturesque setting. Located within walking distance to Mill Hill School, the train, Southport Village, dining, and the harbor, this is a rare opportunity to own a quintessential Fairfield home.

280 Mill Hill Rd, Fairfield

$1,500,000

A rare opportunity to own in the heart of historic Southport Village for under $1.5 million. Beautifully redesigned by the renowned Michael Greenberg & Associates of Westport, this sophisticated two-level residence is located within a landmark building overlooking Southport Harbor. Offering one of the few opportunities to own in Southport Village at this price point, it is ideally suited as a full-time residence or elegant weekend retreat, just a short stroll to the train, Pequot Yacht Club, village shops and restaurants, Southport Beach, the harbor, and everything that makes the Village one of Fairfield County's most sought-after coastal communities. The first floor features a spacious bedroom with a beautifully renovated full bath. Upstairs, an expansive living room, well-appointed kitchen, and powder room create an inviting space for both everyday living and entertaining. Large bay windows fill the home with natural light while capturing picturesque views of Main Street, Southport Harbor, and the Country Club of Fairfield golf course. Combining historic character, designer finishes, harbor views, and an exceptional walk-to-everything location, this is a truly rare opportunity to own a beautifully renovated residence in one of Connecticut's most coveted coastal villages.

1 Beds ⋅ 2 Baths ⋅ 24196135 MLS ⋅ Southport Harbor BLDG.

A rare opportunity to own in the heart of historic Southport Village for under $1.5 million. Beautifully redesigned by the renowned Michael Greenberg & Associates of Westport, this sophisticated two-level residence is located within a landmark building overlooking Southport Harbor. Offering one of the few opportunities to own in Southport Village at this price point, it is ideally suited as a full-time residence or elegant weekend retreat, just a short stroll to the train, Pequot Yacht Club, village shops and restaurants, Southport Beach, the harbor, and everything that makes the Village one of Fairfield County's most sought-after coastal communities. The first floor features a spacious bedroom with a beautifully renovated full bath. Upstairs, an expansive living room, well-appointed kitchen, and powder room create an inviting space for both everyday living and entertaining. Large bay windows fill the home with natural light while capturing picturesque views of Main Street, Southport Harbor, and the Country Club of Fairfield golf course. Combining historic character, designer finishes, harbor views, and an exceptional walk-to-everything location, this is a truly rare opportunity to own a beautifully renovated residence in one of Connecticut's most coveted coastal villages.

236 Main St Unit 236, Fairfield

$1,455,000

A picturesque, expanded and impeccably renovated Cape Cod home located in highly desirable Southport (set off far from road) awaits. Welcome home to 478 Hulls Highway where the character of this Cape blends with today's must have updates. This sun-drenched home features two levels of living, 8 spacious rooms including 3 bedrooms and 2.5 beautifully renovated baths. A rare main level primary suite adds to the convenience and appeal of this special property. Set on an expansive 1.0 acre lot this home has been meticulously updated throughout. Recent home improvements include: all new bathrooms with high-end finishes, renovated eat-in kitchen with new Quartz countertops, new appliances, new backsplash and painted cabinetry, entire interior has been freshly painted, new lighting and hardware throughout, striking new granite hearth fireplace, new central air system, updated plumbing fixtures and a newly paved driveway. The open and flexible floor plan allows for comfortable everyday living & effortless entertaining. Unfinished lower level is ideal for great storage or future home expansion with 864 sf. Attached two car garage provides easy entry into home. Flooded with natural light and filled with charm this home truly has it all. Step outside to a private and peaceful backyard with patio and great space to unwind or host guests. Ideally located and just minutes to Southport Village, beaches, the harbor, top-rated schools and train access - everything you need is at your doorstep!

3 Beds ⋅ 3 Baths ⋅ 24132888 MLS

A picturesque, expanded and impeccably renovated Cape Cod home located in highly desirable Southport (set off far from road) awaits. Welcome home to 478 Hulls Highway where the character of this Cape blends with today's must have updates. This sun-drenched home features two levels of living, 8 spacious rooms including 3 bedrooms and 2.5 beautifully renovated baths. A rare main level primary suite adds to the convenience and appeal of this special property. Set on an expansive 1.0 acre lot this home has been meticulously updated throughout. Recent home improvements include: all new bathrooms with high-end finishes, renovated eat-in kitchen with new Quartz countertops, new appliances, new backsplash and painted cabinetry, entire interior has been freshly painted, new lighting and hardware throughout, striking new granite hearth fireplace, new central air system, updated plumbing fixtures and a newly paved driveway. The open and flexible floor plan allows for comfortable everyday living & effortless entertaining. Unfinished lower level is ideal for great storage or future home expansion with 864 sf. Attached two car garage provides easy entry into home. Flooded with natural light and filled with charm this home truly has it all. Step outside to a private and peaceful backyard with patio and great space to unwind or host guests. Ideally located and just minutes to Southport Village, beaches, the harbor, top-rated schools and train access - everything you need is at your doorstep!

478 Hulls Hwy, Fairfield

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