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Direct waterfront on premier Fairfield Beach with rare sandy frontage and sweeping, panoramic coastline views of the Long Island Sound. This sophisticated 3278sqft 4-bedroom residence offers an exceptional combination of elevation, privacy, and protection by two jetties. Extensively improved with over $400K in recent upgrades, the home is engineered for low-maintenance coastal luxury, featuring high-end Marvin coastal-grade windows and doors complemented by automated Alutech storm shutters [seamless protection at the touch of a button], while the property's low-maintenance composite decking and engineered protective berm ensure both superior flood resilience and effortless upkeep. Inside, the sun-filled open floor plan flows from a one-of-a-kind custom wood kitchen into dining and living areas, leading out to the expansive deck and a private path to the sand. Architectural highlights include 9ft+ ceilings, walls of glass, and a dramatic staircase. The primary wing is a private retreat with breathtaking water views, a personal balcony, and an updated bath. The floor plan includes a versatile upper-level suite that features wall-to-wall water views and a convenient half-bath-ideal for a guest wing, executive office, or fitness studio. A whole-house backup battery, smart home lighting, and a 1-car garage with parking for 8+ cars round out this rare offering. Enjoy the perfect blend of coastal technology and in-town convenience, just moments from the train and town center.

4 Beds ⋅ 4 Baths ⋅ 24151538 MLS

Direct waterfront on premier Fairfield Beach with rare sandy frontage and sweeping, panoramic coastline views of the Long Island Sound. This sophisticated 3278sqft 4-bedroom residence offers an exceptional combination of elevation, privacy, and protection by two jetties. Extensively improved with over $400K in recent upgrades, the home is engineered for low-maintenance coastal luxury, featuring high-end Marvin coastal-grade windows and doors complemented by automated Alutech storm shutters [seamless protection at the touch of a button], while the property's low-maintenance composite decking and engineered protective berm ensure both superior flood resilience and effortless upkeep. Inside, the sun-filled open floor plan flows from a one-of-a-kind custom wood kitchen into dining and living areas, leading out to the expansive deck and a private path to the sand. Architectural highlights include 9ft+ ceilings, walls of glass, and a dramatic staircase. The primary wing is a private retreat with breathtaking water views, a personal balcony, and an updated bath. The floor plan includes a versatile upper-level suite that features wall-to-wall water views and a convenient half-bath-ideal for a guest wing, executive office, or fitness studio. A whole-house backup battery, smart home lighting, and a 1-car garage with parking for 8+ cars round out this rare offering. Enjoy the perfect blend of coastal technology and in-town convenience, just moments from the train and town center.

1053 Fairfield Beach Rd, Fairfield

$3,015,000

Rare Beach Property~ Steps to Sandcastle Playground, Jennings Beach and South Benson Marina - this striking Colonial delivers a unique blend of luxurious beach living and exceptional build quality. Homes of this caliber seldom become available along the shoreline. ~ EXPANSIVE FIRST FLOOR ~ The house features a sprawling first floor Great Room and show stopping Chef's Kitchen which combine in a seamless open layout. The space is anchored by an oversized Carrara marble island, Thermador appliances and a built-in sound system. Light pours in through custom plantation shutters adding to the home's sophisticated and refined coastal aesthetic. ~ PRIVATE RETREATS ~ Upstairs, soaring ceilings and custom millwork adorn a sun-drenched Primary Suite featuring floor-to-ceiling windows and a spacious private balcony, offering a front row seat to epic sunrises and summer fireworks. Four additional bedrooms include two generous en-suites. The fully finished, expansive third level features three private nooks ideal for additional office space or cozy play areas. The third floor bedroom retreat is perfect for in-laws or an au pair and features its own panoramic balcony. ~ OUTDOOR OASIS ~ Lush plantings and mature greenery compliment an expansive bluestone patio and fully fenced yard to create a secluded backyard sanctuary. A UNIQUE OPPORTUNITY to own luxury, craftmanship and privacy at the beach.

6 Beds ⋅ 6 Baths ⋅ 24154688 MLS

Rare Beach Property~ Steps to Sandcastle Playground, Jennings Beach and South Benson Marina - this striking Colonial delivers a unique blend of luxurious beach living and exceptional build quality. Homes of this caliber seldom become available along the shoreline. ~ EXPANSIVE FIRST FLOOR ~ The house features a sprawling first floor Great Room and show stopping Chef's Kitchen which combine in a seamless open layout. The space is anchored by an oversized Carrara marble island, Thermador appliances and a built-in sound system. Light pours in through custom plantation shutters adding to the home's sophisticated and refined coastal aesthetic. ~ PRIVATE RETREATS ~ Upstairs, soaring ceilings and custom millwork adorn a sun-drenched Primary Suite featuring floor-to-ceiling windows and a spacious private balcony, offering a front row seat to epic sunrises and summer fireworks. Four additional bedrooms include two generous en-suites. The fully finished, expansive third level features three private nooks ideal for additional office space or cozy play areas. The third floor bedroom retreat is perfect for in-laws or an au pair and features its own panoramic balcony. ~ OUTDOOR OASIS ~ Lush plantings and mature greenery compliment an expansive bluestone patio and fully fenced yard to create a secluded backyard sanctuary. A UNIQUE OPPORTUNITY to own luxury, craftmanship and privacy at the beach.

598 S Benson Rd, Fairfield

$3,000,000

111 Golden Pond Lane is the rare luxury home that feels as welcoming as it is impressive. Tucked at the end of a quiet, tree-lined cul-de-sac, the home opens with an undeniable scale - soaring 19-foot ceilings, a dramatic two-story entry, sweeping staircases, and natural light that moves effortlessly throughout the day. Yet what makes the home memorable is not its grandeur alone, but the warmth and ease with which it lives. Over the past six years, the residence has been completely transformed by its current owner and designer, blending refined architecture with interiors that feel both elevated and deeply comfortable. At the center of the home, the vaulted family room with stone fireplace and whitewashed beams creates a true gathering space - equally suited for large celebrations or quiet evenings at home. The south-facing kitchen is filled with sunlight and custom detail, designed not simply to impress, but to be used and enjoyed every day. Rarely found, the home offers luxurious primary suite options on both the main and second levels, creating remarkable flexibility for guests, multigenerational living, or evolving needs over time. Outside, an oversized patio overlooks mature trees and complete privacy, with ample room for a future pool and sport court. Peaceful and secluded, yet just seven minutes to Metro-North, the property offers a lifestyle that feels worlds away from the city without sacrificing convenience. Grand in scale. Warm in spirit.

5 Beds ⋅ 8 Baths ⋅ 24175561 MLS

111 Golden Pond Lane is the rare luxury home that feels as welcoming as it is impressive. Tucked at the end of a quiet, tree-lined cul-de-sac, the home opens with an undeniable scale - soaring 19-foot ceilings, a dramatic two-story entry, sweeping staircases, and natural light that moves effortlessly throughout the day. Yet what makes the home memorable is not its grandeur alone, but the warmth and ease with which it lives. Over the past six years, the residence has been completely transformed by its current owner and designer, blending refined architecture with interiors that feel both elevated and deeply comfortable. At the center of the home, the vaulted family room with stone fireplace and whitewashed beams creates a true gathering space - equally suited for large celebrations or quiet evenings at home. The south-facing kitchen is filled with sunlight and custom detail, designed not simply to impress, but to be used and enjoyed every day. Rarely found, the home offers luxurious primary suite options on both the main and second levels, creating remarkable flexibility for guests, multigenerational living, or evolving needs over time. Outside, an oversized patio overlooks mature trees and complete privacy, with ample room for a future pool and sport court. Peaceful and secluded, yet just seven minutes to Metro-North, the property offers a lifestyle that feels worlds away from the city without sacrificing convenience. Grand in scale. Warm in spirit.

111 Golden Pond Ln, Fairfield

$3,000,000

THANK YOU FOR YOUR STRONG INTEREST; SELLER REQUESTS HIGHEST & BEST OFFERS BY 4PM SAT 2/28 . One approaches 1380 Old Academy Road through a stone wall, where a paved drive opens to a gravel courtyard arrival framed by mature trees and open skies. Old Academy is the kind of street where homes feel settled rather than transitional, and where people arrive, put down roots, and tend to stay. Inside, the house is generous without feeling oversized. Tall ceilings, dormers, and bay windows draw natural light deep into the living spaces, allowing it to move easily throughout the day. The main living areas are grounded by multiple fireplaces, and the layout supports everyday living with ease while expanding naturally when the house is full. The finished lower level adds meaningful flexibility, with room for fitness, media, or wine storage. A cabana-style mudroom with a full bath and direct outdoor access extends the way the home lives across seasons. Upstairs, the bedrooms are designed with privacy in mind, offering thoughtful connections that work well for both family and guests. Outdoors, the property becomes a destination in its own right. A Gunite pool bordered by stone terraces, an outdoor fireplace, a putting green, and a side porch with rocking chairs create spaces meant for lingering rather than passing through. Manicured grounds, full irrigation, and a three-car garage complete the setting. Carefully maintained and continually improved, this is Greenfield Hill livi

4 Beds ⋅ 6 Baths ⋅ 24153510 MLS

THANK YOU FOR YOUR STRONG INTEREST; SELLER REQUESTS HIGHEST & BEST OFFERS BY 4PM SAT 2/28 . One approaches 1380 Old Academy Road through a stone wall, where a paved drive opens to a gravel courtyard arrival framed by mature trees and open skies. Old Academy is the kind of street where homes feel settled rather than transitional, and where people arrive, put down roots, and tend to stay. Inside, the house is generous without feeling oversized. Tall ceilings, dormers, and bay windows draw natural light deep into the living spaces, allowing it to move easily throughout the day. The main living areas are grounded by multiple fireplaces, and the layout supports everyday living with ease while expanding naturally when the house is full. The finished lower level adds meaningful flexibility, with room for fitness, media, or wine storage. A cabana-style mudroom with a full bath and direct outdoor access extends the way the home lives across seasons. Upstairs, the bedrooms are designed with privacy in mind, offering thoughtful connections that work well for both family and guests. Outdoors, the property becomes a destination in its own right. A Gunite pool bordered by stone terraces, an outdoor fireplace, a putting green, and a side porch with rocking chairs create spaces meant for lingering rather than passing through. Manicured grounds, full irrigation, and a three-car garage complete the setting. Carefully maintained and continually improved, this is Greenfield Hill livi

1380 Old Academy Rd, Fairfield

$2,995,000

The David Hill Home, Circa 1749. There's a certain kind of house that stops you the moment you pull up. Not because it's trying to impress you - but because the history speaks for itself. Wide plank floors worn smooth by centuries of foot traffic, five original fireplaces, hand-hewn beams - the kind of quiet character newer construction simply can't manufacture. The life inside has been carefully reimagined though. Walls opened, rooms connected, spaces rethought. The chef's kitchen features quartzite countertops and a GE Smart Monogram range. The primary suite is a genuine retreat - radiant marble floors, double vanities, steam shower. Lucifer lighting throughout sets the mood in every room. A sun-drenched bonus room shifts with the seasons - office, sunroom, art studio - whatever the day calls for. The infrastructure has been upgraded too. Full house generator, new Trane HVAC, new smart pool heater and a whole-house water shutoff mean the things you never want to think about are already handled. Outside, the acres unfold into something genuinely private - a pool and spa, pool house, and a barn that's been there longer than almost anything else around it. Lower Greenfield Hill puts you close to everything without feeling like it. Restaurants, shops, top schools, and both Fairfield and Southport train stations all nearby. Some homes you tour. This one you remember.

4 Beds ⋅ 5 Baths ⋅ 24172448 MLS

The David Hill Home, Circa 1749. There's a certain kind of house that stops you the moment you pull up. Not because it's trying to impress you - but because the history speaks for itself. Wide plank floors worn smooth by centuries of foot traffic, five original fireplaces, hand-hewn beams - the kind of quiet character newer construction simply can't manufacture. The life inside has been carefully reimagined though. Walls opened, rooms connected, spaces rethought. The chef's kitchen features quartzite countertops and a GE Smart Monogram range. The primary suite is a genuine retreat - radiant marble floors, double vanities, steam shower. Lucifer lighting throughout sets the mood in every room. A sun-drenched bonus room shifts with the seasons - office, sunroom, art studio - whatever the day calls for. The infrastructure has been upgraded too. Full house generator, new Trane HVAC, new smart pool heater and a whole-house water shutoff mean the things you never want to think about are already handled. Outside, the acres unfold into something genuinely private - a pool and spa, pool house, and a barn that's been there longer than almost anything else around it. Lower Greenfield Hill puts you close to everything without feeling like it. Restaurants, shops, top schools, and both Fairfield and Southport train stations all nearby. Some homes you tour. This one you remember.

40 Hill Brook Ln, Fairfield

$2,950,000

Timeless craftsmanship, extraordinary scale & a level of construction quality increasingly difficult to find define this exceptional estate located in Fairfield's only gated community. Set on over 2 professionally landscaped acres on the Fairfield/Westport border, this home showcases generous room proportions, architectural detail & custom millwork seldom seen. A dramatic double-height foyer introduces over 5,000 sq ft of thoughtfully designed living space. The newly renovated chef's kitchen showcases a quartz waterfall island, full-height quartz backsplash, 2 oversized walk-in pantries, stunning breakfast area & a beautifully appointed wet bar w/beverage refrigerator & sink. The main level also offers a gracious living room w/gas fireplace, spectacular step-down family room w/soaring ceilings & wood-burning fireplace, formal dining room, richly paneled office w/custom built-ins, 2 powder rooms, & an elevator servicing 3 levels. A sweeping staircase leads to the 2nd level where the primary suite offers vaulted ceilings, 2 walk-in closets & a beautifully appointed spa-inspired bath. 3 additional generously sized bedrooms offer comfortable accommodations for family & guests. The finished lower level offers a recreation room w/fireplace, 5th bedroom, full bath, & abundant storage. Outside, 2 bluestone patios create distinct spaces for dining, entertaining & gathering around a built-in gas fireplace all set w/in expansive lawns & exceptional privacy. A rare offering in The Ridge.

4 Beds ⋅ 6 Baths ⋅ 24180342 MLS

Timeless craftsmanship, extraordinary scale & a level of construction quality increasingly difficult to find define this exceptional estate located in Fairfield's only gated community. Set on over 2 professionally landscaped acres on the Fairfield/Westport border, this home showcases generous room proportions, architectural detail & custom millwork seldom seen. A dramatic double-height foyer introduces over 5,000 sq ft of thoughtfully designed living space. The newly renovated chef's kitchen showcases a quartz waterfall island, full-height quartz backsplash, 2 oversized walk-in pantries, stunning breakfast area & a beautifully appointed wet bar w/beverage refrigerator & sink. The main level also offers a gracious living room w/gas fireplace, spectacular step-down family room w/soaring ceilings & wood-burning fireplace, formal dining room, richly paneled office w/custom built-ins, 2 powder rooms, & an elevator servicing 3 levels. A sweeping staircase leads to the 2nd level where the primary suite offers vaulted ceilings, 2 walk-in closets & a beautifully appointed spa-inspired bath. 3 additional generously sized bedrooms offer comfortable accommodations for family & guests. The finished lower level offers a recreation room w/fireplace, 5th bedroom, full bath, & abundant storage. Outside, 2 bluestone patios create distinct spaces for dining, entertaining & gathering around a built-in gas fireplace all set w/in expansive lawns & exceptional privacy. A rare offering in The Ridge.

171 Paddock Hill Ln, Fairfield

$2,950,000

Enjoy life just 44 steps from a private beach path in this completely renovated coastal home, where every detail has been designed for year-round enjoyment. Featuring a sparkling pool, custom outdoor firepit, and spa with panoramic water and Penfield Lighthouse views, this property offers the ultimate blend of luxury and relaxation - all within walking distance to the heart of Fairfield's shops, dining, and train. Inside, the home boasts 4 spacious bedrooms, each with its own ensuite bath, plus a convenient first-floor powder room. Thoughtful updates throughout include a modern chef's kitchen with new GE Monogram appliances, and an expanded quartzite island, refinished hardwood floors, new interior railings, and a stunning new indoor gas fireplace. Natural light flows through new French doors that open to four decks, including mahogany porches with sleek glass railings - perfect for soaking in sunsets or entertaining outdoors. Additional improvements include new lighting and ceiling fans throughout, a finished lower-level loggia with epoxy flooring, and an outdoor shower that completes the private oasis feeling. Practical upgrades ensure peace of mind and modern living: new exterior and interior paint, generator, EV charger, new security system, irrigation system, and spray foam insulation. The beautifully landscaped grounds, mature trees, and pool with year-round hot tub create a true Fairfield Beach retreat. This coastal gem is more than a home - it's a lifestyle

4 Beds ⋅ 5 Baths ⋅ 24122535 MLS

Enjoy life just 44 steps from a private beach path in this completely renovated coastal home, where every detail has been designed for year-round enjoyment. Featuring a sparkling pool, custom outdoor firepit, and spa with panoramic water and Penfield Lighthouse views, this property offers the ultimate blend of luxury and relaxation - all within walking distance to the heart of Fairfield's shops, dining, and train. Inside, the home boasts 4 spacious bedrooms, each with its own ensuite bath, plus a convenient first-floor powder room. Thoughtful updates throughout include a modern chef's kitchen with new GE Monogram appliances, and an expanded quartzite island, refinished hardwood floors, new interior railings, and a stunning new indoor gas fireplace. Natural light flows through new French doors that open to four decks, including mahogany porches with sleek glass railings - perfect for soaking in sunsets or entertaining outdoors. Additional improvements include new lighting and ceiling fans throughout, a finished lower-level loggia with epoxy flooring, and an outdoor shower that completes the private oasis feeling. Practical upgrades ensure peace of mind and modern living: new exterior and interior paint, generator, EV charger, new security system, irrigation system, and spray foam insulation. The beautifully landscaped grounds, mature trees, and pool with year-round hot tub create a true Fairfield Beach retreat. This coastal gem is more than a home - it's a lifestyle

800 Rowland Rd, Fairfield

$2,880,000

There are houses you tour, and then there are estates that capture your imagination. This extraordinary Greenfield Hill Colonial is the latter-a 9,700+ sq. ft. residence set on a pristine 2-acre corner lot in one of Fairfield's most prestigious neighborhoods. A paver-stone drive winds past manicured gardens to a grand two-story entry with a sweeping staircase, setting the tone for elegant living. Meticulously landscaped grounds, fountain, serene stone pathways, and a tranquil koi pond create a private oasis for quiet reflection or outdoor enjoyment. Inside, elegant formal living and dining rooms provide a perfect backdrop for entertaining, while the sun-filled family room, with vaulted ceilings, floor-to-ceiling windows, and a dramatic stone fireplace, serves as the heart of the home. The luxurious primary suite boasts tray ceilings, dual walk-ins, and a marble spa bath. Upstairs, five spacious bedrooms-many ensuite-welcome guests, and the third floor features a game and billiards lounge. A bespoke English pub, thoughtfully designed and versatile, can serve as a lounge, home office, entertainment room, or hobby space. Outdoors, a gated saltwater pool and hot tub with a fully equipped poolhouse create an inviting retreat for summer gatherings. This remarkable estate blends sophistication, comfort, and timeless appeal-a sanctuary for grand occasions and quiet moments alike.

6 Beds ⋅ 8 Baths ⋅ 24123339 MLS

There are houses you tour, and then there are estates that capture your imagination. This extraordinary Greenfield Hill Colonial is the latter-a 9,700+ sq. ft. residence set on a pristine 2-acre corner lot in one of Fairfield's most prestigious neighborhoods. A paver-stone drive winds past manicured gardens to a grand two-story entry with a sweeping staircase, setting the tone for elegant living. Meticulously landscaped grounds, fountain, serene stone pathways, and a tranquil koi pond create a private oasis for quiet reflection or outdoor enjoyment. Inside, elegant formal living and dining rooms provide a perfect backdrop for entertaining, while the sun-filled family room, with vaulted ceilings, floor-to-ceiling windows, and a dramatic stone fireplace, serves as the heart of the home. The luxurious primary suite boasts tray ceilings, dual walk-ins, and a marble spa bath. Upstairs, five spacious bedrooms-many ensuite-welcome guests, and the third floor features a game and billiards lounge. A bespoke English pub, thoughtfully designed and versatile, can serve as a lounge, home office, entertainment room, or hobby space. Outdoors, a gated saltwater pool and hot tub with a fully equipped poolhouse create an inviting retreat for summer gatherings. This remarkable estate blends sophistication, comfort, and timeless appeal-a sanctuary for grand occasions and quiet moments alike.

21 Queens Grant Dr, Fairfield

$2,875,000

A rare opportunity on one of the most coveted streets in the Fairfield Beach neighborhood, just one block from the shoreline and less than a mile from downtown. Built in 2013 by Garrett Wilson Builders, this exceptional custom home offers 5 bedrooms and 4.5 baths. Along with refined craftsmanship, thoughtful design, and effortless coastal living. The main level is defined by 10' ceilings, exceptional natural light, exquisite millwork, and an open-concept layout anchored by a remarkable kitchen. Seamlessly connecting gracious living and dining spaces, this distinctive home is ideal for both everyday living and entertaining. Upstairs, the second-floor features four well-proportioned bedrooms, three full baths, and a conveniently located laundry room. The third floor offers exceptional flexibility with an additional bedroom, full bath, plus a wet bar with beverage fridge. This spacious bonus area is complete with surround sound, perfect for guests, work, or playroom. Every detail has been carefully curated, from wide plank white oak floors throughout and custom built-ins, to the finest hardware and finishes. A covered rear porch and beautifully maintained outdoor spaces extend the living experience outdoors. This meticulously maintained home also includes approved plans to expand and finish the space above the garage into an office or den. Just moments to the beach, town, and train, this is coastal living at its finest.

5 Beds ⋅ 5 Baths ⋅ 24167679 MLS

A rare opportunity on one of the most coveted streets in the Fairfield Beach neighborhood, just one block from the shoreline and less than a mile from downtown. Built in 2013 by Garrett Wilson Builders, this exceptional custom home offers 5 bedrooms and 4.5 baths. Along with refined craftsmanship, thoughtful design, and effortless coastal living. The main level is defined by 10' ceilings, exceptional natural light, exquisite millwork, and an open-concept layout anchored by a remarkable kitchen. Seamlessly connecting gracious living and dining spaces, this distinctive home is ideal for both everyday living and entertaining. Upstairs, the second-floor features four well-proportioned bedrooms, three full baths, and a conveniently located laundry room. The third floor offers exceptional flexibility with an additional bedroom, full bath, plus a wet bar with beverage fridge. This spacious bonus area is complete with surround sound, perfect for guests, work, or playroom. Every detail has been carefully curated, from wide plank white oak floors throughout and custom built-ins, to the finest hardware and finishes. A covered rear porch and beautifully maintained outdoor spaces extend the living experience outdoors. This meticulously maintained home also includes approved plans to expand and finish the space above the garage into an office or den. Just moments to the beach, town, and train, this is coastal living at its finest.

550 Penfield 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

$2,850,000

There's a certain kind of iconic home that settles over you the moment you step inside, because the craftsmanship was never meant to be temporary. Nine-foot ceilings in the living & dining rooms, 3 wood-burning fireplaces, solid proportions & large windows & glass doors that still frame the light the way they were designed to nearly a century ago. The kind of quiet authority that newer construction spends a fortune trying to approximate. The current owners understood the assignment. They preserved what mattered & refined the rest without ever losing the house's original voice. The original 1929 paneled den with a hidden wet bar. A family room built for actual gathering, complete with Sub-Zero, beverage fridge & kegerator. The gourmet kitchen opens directly onto an oversized patio so the line between inside & outside nearly disappears. 5/6 beds, 5.5 stunning baths, two staircases, a first-floor office, & a walk-out lower level with its own entrance & full bath give the house a flexibility that feels intentional. Outside, 1+ acres sit quietly behind stone walls - already equipped with a grilling station, a built-in fire pit, irrigation, & the soft structure of mature plantings, privacy & play space. You can walk to Fairfield's vibrant downtown, the Metro-North station to NYC, & schools. You border lovely Winton Park. Natural gas, city water, town sewer. Some homes you tour. This one stays with you. A spectacular house with a soul.

5 Beds ⋅ 6 Baths ⋅ 24195451 MLS

There's a certain kind of iconic home that settles over you the moment you step inside, because the craftsmanship was never meant to be temporary. Nine-foot ceilings in the living & dining rooms, 3 wood-burning fireplaces, solid proportions & large windows & glass doors that still frame the light the way they were designed to nearly a century ago. The kind of quiet authority that newer construction spends a fortune trying to approximate. The current owners understood the assignment. They preserved what mattered & refined the rest without ever losing the house's original voice. The original 1929 paneled den with a hidden wet bar. A family room built for actual gathering, complete with Sub-Zero, beverage fridge & kegerator. The gourmet kitchen opens directly onto an oversized patio so the line between inside & outside nearly disappears. 5/6 beds, 5.5 stunning baths, two staircases, a first-floor office, & a walk-out lower level with its own entrance & full bath give the house a flexibility that feels intentional. Outside, 1+ acres sit quietly behind stone walls - already equipped with a grilling station, a built-in fire pit, irrigation, & the soft structure of mature plantings, privacy & play space. You can walk to Fairfield's vibrant downtown, the Metro-North station to NYC, & schools. You border lovely Winton Park. Natural gas, city water, town sewer. Some homes you tour. This one stays with you. A spectacular house with a soul.

1123 Round Hill Rd, Fairfield

$2,850,000

Inspired living meets coastal New England charm at 309 Birch Rd in Fairfield. This thoughtfully designed home in the beach area blends elegant millwork, hardwood floors, transom windows, plantation shutters and custom built-ins with natural light throughout. The two-story foyer welcomes you to superior craftsmanship, leading to a private office and front porch, formal dining with wood-burning fireplace and built-ins, and a serene living room overlooking lush grounds. The heart of the home, the eat-in kitchen, features Wolf appliances, Waterworks fixtures, honed Pietra Cardosa schist stone, white cabinetry with seeded glass, quartz island, and breakfast area opening to a two-story family room with vaulted ceiling, brick fireplace, and beverage nook. Upstairs, four bedrooms include a primary suite with tray ceiling, spa-like bath, and a walk-in closet. Three additional bedrooms on the second floor have unique attributes - custom built-ins, windowseats, stylish wallpaper, and gorgeous views. The finished third floor adds a 5th en-suite bedroom and bonus room. The fully fenced-in yard, bordered by beautiful landscaping offers space to relax, play, or dine al fresco. A two-car attached garage completes this home with 20 ft ceilings, plenty of storage, and the potential for a lift adding a desirable element for any car enthusiast. Perfectly positioned for the coastal lifestyle of your dreams, this home is just a short stroll to the beach, schools, train station & downtown Fairfield

5 Beds ⋅ 4 Baths ⋅ 24173340 MLS

Inspired living meets coastal New England charm at 309 Birch Rd in Fairfield. This thoughtfully designed home in the beach area blends elegant millwork, hardwood floors, transom windows, plantation shutters and custom built-ins with natural light throughout. The two-story foyer welcomes you to superior craftsmanship, leading to a private office and front porch, formal dining with wood-burning fireplace and built-ins, and a serene living room overlooking lush grounds. The heart of the home, the eat-in kitchen, features Wolf appliances, Waterworks fixtures, honed Pietra Cardosa schist stone, white cabinetry with seeded glass, quartz island, and breakfast area opening to a two-story family room with vaulted ceiling, brick fireplace, and beverage nook. Upstairs, four bedrooms include a primary suite with tray ceiling, spa-like bath, and a walk-in closet. Three additional bedrooms on the second floor have unique attributes - custom built-ins, windowseats, stylish wallpaper, and gorgeous views. The finished third floor adds a 5th en-suite bedroom and bonus room. The fully fenced-in yard, bordered by beautiful landscaping offers space to relax, play, or dine al fresco. A two-car attached garage completes this home with 20 ft ceilings, plenty of storage, and the potential for a lift adding a desirable element for any car enthusiast. Perfectly positioned for the coastal lifestyle of your dreams, this home is just a short stroll to the beach, schools, train station & downtown Fairfield

309 Birch Rd, Fairfield

$2,850,000

No need to journey to the South of France...this extraordinary estate brings European romance & luxury to coveted Fairfield, CT. Beyond grand gates lies a private world where beauty, security, & serenity exist in perfect harmony. Magazine-worthy grounds define the estate, featuring a gorgeous pool, spectacular CA Redwood Pool House w/ full kitchen, covered entertaining spaces, mature gardens, bluestone terraces, & sweeping lawns...creating a setting that feels like a private resort. Inside, the open-concept design centers on a chef's kitchen that flows seamlessly into a breathtaking Great Room with soaring ceilings & a dramatic stone fireplace. Elegant formal living and dining rooms, a sun-filled family room with fireplace, and a remarkable home office w/ fplc offer both sophistication and comfort. The main residence offers 4-5 bedrooms, including a magnificent Primary Suite with sitting areas, private balcony, custom closets, and a spa-inspired bath w/ romantic fireplace. A separate first-floor wing with lounge and additional bedrooms provides ideal flexibility for family, in-laws or guests. A charming guest cottage, private suite above the carriage house, and a storybook artist's studio or gym complete this exceptional compound. Ideally positioned for today's lifestyle, Lions Gate offers the rare balance of peaceful seclusion & everyday convenience, just minutes to train, town & beaches, with easy access to Metro NYC, yet a setting that feels like a countryside retreat.

6 Beds ⋅ 8 Baths ⋅ 24170071 MLS

No need to journey to the South of France...this extraordinary estate brings European romance & luxury to coveted Fairfield, CT. Beyond grand gates lies a private world where beauty, security, & serenity exist in perfect harmony. Magazine-worthy grounds define the estate, featuring a gorgeous pool, spectacular CA Redwood Pool House w/ full kitchen, covered entertaining spaces, mature gardens, bluestone terraces, & sweeping lawns...creating a setting that feels like a private resort. Inside, the open-concept design centers on a chef's kitchen that flows seamlessly into a breathtaking Great Room with soaring ceilings & a dramatic stone fireplace. Elegant formal living and dining rooms, a sun-filled family room with fireplace, and a remarkable home office w/ fplc offer both sophistication and comfort. The main residence offers 4-5 bedrooms, including a magnificent Primary Suite with sitting areas, private balcony, custom closets, and a spa-inspired bath w/ romantic fireplace. A separate first-floor wing with lounge and additional bedrooms provides ideal flexibility for family, in-laws or guests. A charming guest cottage, private suite above the carriage house, and a storybook artist's studio or gym complete this exceptional compound. Ideally positioned for today's lifestyle, Lions Gate offers the rare balance of peaceful seclusion & everyday convenience, just minutes to train, town & beaches, with easy access to Metro NYC, yet a setting that feels like a countryside retreat.

750 Burr St, 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

$2,750,000

Newly renovated in 2026, this extraordinary designer-inspired Modern Colonial presents a rare opportunity to own a turnkey luxury residence in Fairfield's coveted Sasco Hill. Offering 3,625 square feet of impeccably designed living space, this four-bedroom, five-bath home masterfully blends timeless architecture with exceptional craftsmanship and sophisticated contemporary design. Every detail has been meticulously curated, from the custom white oak millwork and hardwood flooring to the spectacular chef's kitchen featuring Taj Mahal quartzite countertops, premium Thermador appliances, custom cabinetry, and an oversized waterfall island. The thoughtfully designed first floor offers a gracious living room with fireplace, formal dining room, private office, family room, and a sun-filled eat-in kitchen that opens to an expansive bluestone terrace for seamless indoor-outdoor living. Upstairs, the luxurious primary suite features a cathedral ceiling, dual walk-in closets, separate sitting room and a spa-inspired bath. Three additional en-suite bedrooms provide outstanding comfort and privacy. Additional highlights include a beautifully finished lower level, 3-car garage, custom built-ins, four-zone HVAC, Generac generator, and designer finishes throughout. Ideally located minutes from downtown Fairfield, Southport Village, Metro-North, beaches, parks, shopping, and dining, this exceptional home offers luxury living in one of Fairfield's most prestigious neighborhoods.

4 Beds ⋅ 5 Baths ⋅ 24191170 MLS

Newly renovated in 2026, this extraordinary designer-inspired Modern Colonial presents a rare opportunity to own a turnkey luxury residence in Fairfield's coveted Sasco Hill. Offering 3,625 square feet of impeccably designed living space, this four-bedroom, five-bath home masterfully blends timeless architecture with exceptional craftsmanship and sophisticated contemporary design. Every detail has been meticulously curated, from the custom white oak millwork and hardwood flooring to the spectacular chef's kitchen featuring Taj Mahal quartzite countertops, premium Thermador appliances, custom cabinetry, and an oversized waterfall island. The thoughtfully designed first floor offers a gracious living room with fireplace, formal dining room, private office, family room, and a sun-filled eat-in kitchen that opens to an expansive bluestone terrace for seamless indoor-outdoor living. Upstairs, the luxurious primary suite features a cathedral ceiling, dual walk-in closets, separate sitting room and a spa-inspired bath. Three additional en-suite bedrooms provide outstanding comfort and privacy. Additional highlights include a beautifully finished lower level, 3-car garage, custom built-ins, four-zone HVAC, Generac generator, and designer finishes throughout. Ideally located minutes from downtown Fairfield, Southport Village, Metro-North, beaches, parks, shopping, and dining, this exceptional home offers luxury living in one of Fairfield's most prestigious neighborhoods.

131 Sasco Hill Rd, Fairfield

$2,750,000

Welcome to an unrivaled sanctuary of sophistication at 342 Midlock Road, gracefully situated in the prestigious enclave of Greenfield Hill. This stately residence, perched on a coveted cul-de-sac off Burr Street, unfurls over two lush acres of meticulously manicured, fully fenced grounds. Upon entry, be enveloped in luxury as you traverse through spaces adorned with custom millwork, nine ft ceilings, abundant natural light and more. The heart of this home is an eat-in chef's kitchen, replete with top-tier stainless steel appliances, which connects you to multiple other spaces for enjoyment or repose. Entertain with panache in the formal dining room, garden room, library, living room or great room. Five fireplaces spread across this generous layout hosting five bedrooms- all ensuite- plus additional oversized office/media room with kitchenette, as well as third floor rec room with attached full bath and access to boutique-style cedar closet. Outdoors, a resplendent oasis awaits, featuring a pristine gunite with pebble sheen pool, granite heat resistant patio and an exquisite pool house with kitchenette and full bath, and expansive stone outdoor kitchen- a sublime setting for al fresco gatherings. A lifestyle of unparalleled elegance and comfort is a given. Every detail of this meticulously maintained home harmonizes to create an estate that epitomizes refined living. This majestic manor reflects pride in ownership and a timelessness that commands to be experienced.

5 Beds ⋅ 7 Baths ⋅ 24134949 MLS

Welcome to an unrivaled sanctuary of sophistication at 342 Midlock Road, gracefully situated in the prestigious enclave of Greenfield Hill. This stately residence, perched on a coveted cul-de-sac off Burr Street, unfurls over two lush acres of meticulously manicured, fully fenced grounds. Upon entry, be enveloped in luxury as you traverse through spaces adorned with custom millwork, nine ft ceilings, abundant natural light and more. The heart of this home is an eat-in chef's kitchen, replete with top-tier stainless steel appliances, which connects you to multiple other spaces for enjoyment or repose. Entertain with panache in the formal dining room, garden room, library, living room or great room. Five fireplaces spread across this generous layout hosting five bedrooms- all ensuite- plus additional oversized office/media room with kitchenette, as well as third floor rec room with attached full bath and access to boutique-style cedar closet. Outdoors, a resplendent oasis awaits, featuring a pristine gunite with pebble sheen pool, granite heat resistant patio and an exquisite pool house with kitchenette and full bath, and expansive stone outdoor kitchen- a sublime setting for al fresco gatherings. A lifestyle of unparalleled elegance and comfort is a given. Every detail of this meticulously maintained home harmonizes to create an estate that epitomizes refined living. This majestic manor reflects pride in ownership and a timelessness that commands to be experienced.

342 Midlock Rd, 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

$2,725,000

Premier direct waterfront living w/ ownership extending to the creek side, miles of sandy beach for endless walks, spectacular water views & a pristine 4 bedroom home - Welcome to 1871/1872 Fairfield Beach Road. Set on a .22, level acre w/ additional creek side parking for convenience. From the moment you arrive, the covered wraparound porch invites you to relax & enjoy the gorgeous water views. Inside, sunlight streams through every room, creating bright, airy spaces that feel both welcoming & peaceful. The main level offers spacious living areas, including an eat-in kitchen w/ an island, dining area & laundry room. The inviting family room features a stone fireplace, while the sunroom showcases unobstructed, panoramic water views. The French door opens to an expansive patio & sandy beach, creating the perfect connection between indoor & outdoor living while providing an amazing setting for entertaining or simply enjoying the beautiful waterfront. The 2nd level features 4 bedrooms, including 2 that capture breathtaking water views, along w/ a hall bath. The 3rd level offers flexible space w/ water views, making it ideal for a home office, studio, reading retreat or added storage. Perfectly positioned this home offers the rare combination of tranquil coastal living w/ convenient access to Fairfield's acclaimed restaurants, boutique shopping, train, parks & schools. From sandy beach walks to sunset gatherings, this is more than a home, it is an exceptional lifestyle.

4 Beds ⋅ 2 Baths ⋅ 24187347 MLS

Premier direct waterfront living w/ ownership extending to the creek side, miles of sandy beach for endless walks, spectacular water views & a pristine 4 bedroom home - Welcome to 1871/1872 Fairfield Beach Road. Set on a .22, level acre w/ additional creek side parking for convenience. From the moment you arrive, the covered wraparound porch invites you to relax & enjoy the gorgeous water views. Inside, sunlight streams through every room, creating bright, airy spaces that feel both welcoming & peaceful. The main level offers spacious living areas, including an eat-in kitchen w/ an island, dining area & laundry room. The inviting family room features a stone fireplace, while the sunroom showcases unobstructed, panoramic water views. The French door opens to an expansive patio & sandy beach, creating the perfect connection between indoor & outdoor living while providing an amazing setting for entertaining or simply enjoying the beautiful waterfront. The 2nd level features 4 bedrooms, including 2 that capture breathtaking water views, along w/ a hall bath. The 3rd level offers flexible space w/ water views, making it ideal for a home office, studio, reading retreat or added storage. Perfectly positioned this home offers the rare combination of tranquil coastal living w/ convenient access to Fairfield's acclaimed restaurants, boutique shopping, train, parks & schools. From sandy beach walks to sunset gatherings, this is more than a home, it is an exceptional lifestyle.

1871 Fairfield Beach 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

$2,700,000

Located in the heart of Greenfield Hill, "Upper Meadow Farm" is a rare blend of timeless character and modern comfort. Originally dating back to 1835, this storied property at 2821 Congress Street has been thoughtfully expanded and updated over the years, most recently in 2019 by the current owners. The result is a warm, welcoming home where historic details meet a fresh, refined palette. A spacious first-floor primary suite offers privacy and stunning southern views across the property, complete with a fireplace, office, and walk-in closet. The main living areas are gracious yet inviting, ideal for everyday living or hosting guests. Upstairs are four additional bedrooms and three full baths, one currently used as a home office. Step outside and discover the true magic of the property: a beautifully reimagined former blacksmith's barn with a loft, full bath, and bar area-perfect as a guest house, studio, or entertainment space. The pool, added in 2015, is complemented by a stylish pool house featuring a kitchenette, full bath, and generous terracing for summer evenings under the stars. Set on picturesque grounds, this is an exceptional opportunity for those seeking a full-time residence or a weekend retreat in one of Fairfield's most beloved neighborhoods. A truly special home.

5 Beds ⋅ 5 Baths ⋅ 24111053 MLS

Located in the heart of Greenfield Hill, "Upper Meadow Farm" is a rare blend of timeless character and modern comfort. Originally dating back to 1835, this storied property at 2821 Congress Street has been thoughtfully expanded and updated over the years, most recently in 2019 by the current owners. The result is a warm, welcoming home where historic details meet a fresh, refined palette. A spacious first-floor primary suite offers privacy and stunning southern views across the property, complete with a fireplace, office, and walk-in closet. The main living areas are gracious yet inviting, ideal for everyday living or hosting guests. Upstairs are four additional bedrooms and three full baths, one currently used as a home office. Step outside and discover the true magic of the property: a beautifully reimagined former blacksmith's barn with a loft, full bath, and bar area-perfect as a guest house, studio, or entertainment space. The pool, added in 2015, is complemented by a stylish pool house featuring a kitchenette, full bath, and generous terracing for summer evenings under the stars. Set on picturesque grounds, this is an exceptional opportunity for those seeking a full-time residence or a weekend retreat in one of Fairfield's most beloved neighborhoods. A truly special home.

2821 Congress St, Fairfield

$2,650,000

Spectacular custom estate built by Andy Frank in prestigious Greenfield Hill featuring a rare first-floor primary suite w/fireplace, spacious WIC, luxurious spa bath & vaulted ceiling -- a true standout for convenient main-level living. Set on over 2 magnificent landscaped acres on a double cul-de-sac, this home delivers resort-style living w/exceptional privacy. Outside, an oversized free-form gunite pool w/waterfall anchors spectacular entertaining & relaxing areas, complemented by stone walls, a large stone patio, and lovely deck - and enhanced by beautiful mature plantings & deer fencing. Inside, a dramatic double-height foyer w/marble floor leads into a custom EIK with quartz countertops, an oversized island & pantry that opens seamlessly to the lovely family/living room & idyllic backyard. Another larger family room features a custom bar, pool table, built-ins, and a half bath. Three fireplaces, a first-floor library/office, custom laundry room & two staircases complete the first floor. Upstairs, the second floor offers four large bedrooms & two beautifully full baths. The finished walk-out LLevel is an entertainer's dream, complete w/custom wine cellar, full bath, wet bar, multiple entertaining zones, storage rooms & gym space. Exquisite millwork & detail throughout. This private, spacious setting is a short drive to the train for NY commuters, & to vibrant shops, restaurants & the energy of downtown Fairfield & Westport. Natural gas completes this special property.

5 Beds ⋅ 6 Baths ⋅ 24188324 MLS

Spectacular custom estate built by Andy Frank in prestigious Greenfield Hill featuring a rare first-floor primary suite w/fireplace, spacious WIC, luxurious spa bath & vaulted ceiling -- a true standout for convenient main-level living. Set on over 2 magnificent landscaped acres on a double cul-de-sac, this home delivers resort-style living w/exceptional privacy. Outside, an oversized free-form gunite pool w/waterfall anchors spectacular entertaining & relaxing areas, complemented by stone walls, a large stone patio, and lovely deck - and enhanced by beautiful mature plantings & deer fencing. Inside, a dramatic double-height foyer w/marble floor leads into a custom EIK with quartz countertops, an oversized island & pantry that opens seamlessly to the lovely family/living room & idyllic backyard. Another larger family room features a custom bar, pool table, built-ins, and a half bath. Three fireplaces, a first-floor library/office, custom laundry room & two staircases complete the first floor. Upstairs, the second floor offers four large bedrooms & two beautifully full baths. The finished walk-out LLevel is an entertainer's dream, complete w/custom wine cellar, full bath, wet bar, multiple entertaining zones, storage rooms & gym space. Exquisite millwork & detail throughout. This private, spacious setting is a short drive to the train for NY commuters, & to vibrant shops, restaurants & the energy of downtown Fairfield & Westport. Natural gas completes this special property.

73 Foggwood Cir, 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

$2,600,000

Iconic Georgian Manor. A rare offering of architectural significance, this distinguished 1922 Georgian Colonial is set on 1.88 acres of level, park-like grounds in a desirable Fairfield enclave. Encompassing over 10,000 square feet, this 6-bedroom estate seamlessly blends historic grandeur with elevated, modern living. A stately presence is immediately felt through classic Georgian symmetry, framed by elegant columns and enhanced by exquisite millwork, intricate moldings, and timeless architectural detailing throughout. Inside, a series of beautifully scaled rooms unfold, each more impressive than the next, including a refined library, private office, sun-drenched solarium, and multiple formal and informal living spaces anchored by seven fireplaces, creating warmth and character at every turn. At the heart of the home, a true chef's kitchen is designed for both everyday living and elevated entertaining, seamlessly connecting to expansive interior and exterior gathering spaces. The grounds are nothing short of resort-caliber, featuring an oversized pool, tennis court, and sweeping lawns that create a sense of total privacy and escape. A fully equipped guest house with gym and sauna offers exceptional flexibility, ideal for extended stays, a wellness retreat, or a private art or music studio. Offered fully furnished, the home is further elevated by beautifully curated furnishings that complement its architectural character and refined aesthetic, creating a seamless

6 Beds ⋅ 7 Baths ⋅ 24161480 MLS

Iconic Georgian Manor. A rare offering of architectural significance, this distinguished 1922 Georgian Colonial is set on 1.88 acres of level, park-like grounds in a desirable Fairfield enclave. Encompassing over 10,000 square feet, this 6-bedroom estate seamlessly blends historic grandeur with elevated, modern living. A stately presence is immediately felt through classic Georgian symmetry, framed by elegant columns and enhanced by exquisite millwork, intricate moldings, and timeless architectural detailing throughout. Inside, a series of beautifully scaled rooms unfold, each more impressive than the next, including a refined library, private office, sun-drenched solarium, and multiple formal and informal living spaces anchored by seven fireplaces, creating warmth and character at every turn. At the heart of the home, a true chef's kitchen is designed for both everyday living and elevated entertaining, seamlessly connecting to expansive interior and exterior gathering spaces. The grounds are nothing short of resort-caliber, featuring an oversized pool, tennis court, and sweeping lawns that create a sense of total privacy and escape. A fully equipped guest house with gym and sauna offers exceptional flexibility, ideal for extended stays, a wellness retreat, or a private art or music studio. Offered fully furnished, the home is further elevated by beautifully curated furnishings that complement its architectural character and refined aesthetic, creating a seamless

91 Algonquin Rd, Fairfield

$2,600,000

Spectacular New Construction in the Sasco Beach Area. Don't miss the rare opportunity to customize and make this home your own.Located on almost a half acre of peaceful, private property, last house on a cul-de-sac, backing up to open land on Sasco Hill. Distant water views, serenity, extensively manicured yard and just steps to South Pine Creek Beach.. a very special quaint beach with life guards in the summer. Almost 4000 sq feet of finished space on three levels w views from every window!!plus an additional 550 Sq feet in basement. Walk everywhere location, near parks, golf, nature paths, walk to town, close to highways and train. The possibilities are endless! Let's meet with the builders and walk the property and go over plans. Opportunity awaits! Construction is under way. Ready late Fall. House is all framed... time to pick your finishes!

5 Beds ⋅ 5 Baths ⋅ 24092857 MLS

Spectacular New Construction in the Sasco Beach Area. Don't miss the rare opportunity to customize and make this home your own.Located on almost a half acre of peaceful, private property, last house on a cul-de-sac, backing up to open land on Sasco Hill. Distant water views, serenity, extensively manicured yard and just steps to South Pine Creek Beach.. a very special quaint beach with life guards in the summer. Almost 4000 sq feet of finished space on three levels w views from every window!!plus an additional 550 Sq feet in basement. Walk everywhere location, near parks, golf, nature paths, walk to town, close to highways and train. The possibilities are endless! Let's meet with the builders and walk the property and go over plans. Opportunity awaits! Construction is under way. Ready late Fall. House is all framed... time to pick your finishes!

154 Gorham Rd, Fairfield

$2,525,000

One of the most classic, iconic, beautiful & beloved streets & home in the entire Beach area, set on a rare .30-acre private lot await. This 11-room, 4-level Colonial offers exceptional living space. The current homeowner has made significant improvements, including a new multi-level deck, new fence & gates, a beautifully renovated powder room & upstairs hall bath, fresh interior /exterior paint, a new Sub-Zero refrigerator & refinished hardwood floors. 126 Lalley Blvd. radiates warmth, from the brilliant sunlight that pours through every room to its timeless character. Each room has its own individuality. The impressive dining room features a fireplace & French doors, easily accommodating large parties & flows into the cozy family room. There, you will find 3 sets of French doors bringing in bright, natural light, a fireplace, built-ins & direct access to the eat-in kitchen. A den, mudroom & powder room complete the main level. Upstairs, 4 spacious bedrooms w/ excellent closet space, including the primary suite w/ 2 walk-in closets, dressing room, French doors leading to a private balcony & a spa-like bath await. The 3rd level offers flexible space as an office, gym or family room. PLUS a finished lower level rec room w/ storage. From April- November, the new homeowner is in for a surprise w/ a breathtaking display of colorful perennial gardens in bloom. All this w/in walking distance to beach, town, train, schools, parks, dining & shops. A very special place to call home!

4 Beds ⋅ 3 Baths ⋅ 24154340 MLS

One of the most classic, iconic, beautiful & beloved streets & home in the entire Beach area, set on a rare .30-acre private lot await. This 11-room, 4-level Colonial offers exceptional living space. The current homeowner has made significant improvements, including a new multi-level deck, new fence & gates, a beautifully renovated powder room & upstairs hall bath, fresh interior /exterior paint, a new Sub-Zero refrigerator & refinished hardwood floors. 126 Lalley Blvd. radiates warmth, from the brilliant sunlight that pours through every room to its timeless character. Each room has its own individuality. The impressive dining room features a fireplace & French doors, easily accommodating large parties & flows into the cozy family room. There, you will find 3 sets of French doors bringing in bright, natural light, a fireplace, built-ins & direct access to the eat-in kitchen. A den, mudroom & powder room complete the main level. Upstairs, 4 spacious bedrooms w/ excellent closet space, including the primary suite w/ 2 walk-in closets, dressing room, French doors leading to a private balcony & a spa-like bath await. The 3rd level offers flexible space as an office, gym or family room. PLUS a finished lower level rec room w/ storage. From April- November, the new homeowner is in for a surprise w/ a breathtaking display of colorful perennial gardens in bloom. All this w/in walking distance to beach, town, train, schools, parks, dining & shops. A very special place to call home!

126 Lalley Blvd, Fairfield

$2,525,000

A Rare Opportunity in the Beach Area- Set on an oversized .42-acre lot at the end of a quiet cul-de-sac, this custom-built home offers a rare combination of space, quality, and location. Uniquely positioned with a deep front setback and an expansive backyard-this property stands apart from typical neighborhood lots. Ample room for a pool and more! Thoughtfully designed for both comfort and function, the home offers abundant living space encompassing all the elements a buyer would desire including a family room with fireplace, den/home office, and a four-season sunroom-ideal for relaxing or entertaining year-round. At the heart of the home is a custom chef's kitchen with a center island offering seating, high-end finishes, and seamless flow to the main living areas. Built to the highest standards, the home features 9-foot ceilings on both the first and second floors, wide plank hardwood floors, spray foam insulation for energy efficiency and an abundance of storage space. Every bedroom includes an en-suite bath, and the expansive primary suite boasts a spacious dressing room. Located just a short stroll to Penfield Beach and the town green, this is beach-area living at its finest-where quality, space, and convenience come together in a truly special setting.

4 Beds ⋅ 5 Baths ⋅ 24108692 MLS

A Rare Opportunity in the Beach Area- Set on an oversized .42-acre lot at the end of a quiet cul-de-sac, this custom-built home offers a rare combination of space, quality, and location. Uniquely positioned with a deep front setback and an expansive backyard-this property stands apart from typical neighborhood lots. Ample room for a pool and more! Thoughtfully designed for both comfort and function, the home offers abundant living space encompassing all the elements a buyer would desire including a family room with fireplace, den/home office, and a four-season sunroom-ideal for relaxing or entertaining year-round. At the heart of the home is a custom chef's kitchen with a center island offering seating, high-end finishes, and seamless flow to the main living areas. Built to the highest standards, the home features 9-foot ceilings on both the first and second floors, wide plank hardwood floors, spray foam insulation for energy efficiency and an abundance of storage space. Every bedroom includes an en-suite bath, and the expansive primary suite boasts a spacious dressing room. Located just a short stroll to Penfield Beach and the town green, this is beach-area living at its finest-where quality, space, and convenience come together in a truly special setting.

35 Millard St, Fairfield

$2,515,000

From the moment you arrive, you are captivated w/ blooming gardens & privacy trees that create an inviting curb appeal that welcomes you in. Architecturally gorgeous w/ brilliant craftmanship, this coastal home is a rare find in the Beach neighborhood. Featuring 4 spacious en-suite bedrooms, 12 rooms, 3 levels & an elevator servicing all floors, this home sets a new standard for exceptional living. The attention to detail is unmatched w/ wide plank hardwood floors, custom millwork, 9 ft+ ceilings, built-ins & elegant finishes. The 1st level is centered around the chef's kitchen featuring a large island, Viking appliances, wine chiller & dining that opens to the family room w/ fireplace & access to beautifully designed outdoor patios - perfect for indoor-outdoor entertaining. Additional living spaces include a library w/ fireplace & built-ins, dining room & a flexible recreation room w/ balconies. Upstairs, the architectural charm continues w/ curved walls & bookshelves & 3 of the en-suite bedrooms, including a peaceful primary suite w/ fireplace, walk-in closet & spa-like bath. The 3rd level features the 4th en-suite bedroom, bonus room & full bath - an ideal retreat for an au pair, in-law or guests. Outside, your relaxation awaits w/ multiple patios for lounging, an in-ground pool, firepit & shower - designed for complete privacy & entertaining. Walk to beach, marina & vibrant downtown, train station, top rated schools, parks & dining - this home & location truly has it all!

4 Beds ⋅ 6 Baths ⋅ 24124637 MLS

From the moment you arrive, you are captivated w/ blooming gardens & privacy trees that create an inviting curb appeal that welcomes you in. Architecturally gorgeous w/ brilliant craftmanship, this coastal home is a rare find in the Beach neighborhood. Featuring 4 spacious en-suite bedrooms, 12 rooms, 3 levels & an elevator servicing all floors, this home sets a new standard for exceptional living. The attention to detail is unmatched w/ wide plank hardwood floors, custom millwork, 9 ft+ ceilings, built-ins & elegant finishes. The 1st level is centered around the chef's kitchen featuring a large island, Viking appliances, wine chiller & dining that opens to the family room w/ fireplace & access to beautifully designed outdoor patios - perfect for indoor-outdoor entertaining. Additional living spaces include a library w/ fireplace & built-ins, dining room & a flexible recreation room w/ balconies. Upstairs, the architectural charm continues w/ curved walls & bookshelves & 3 of the en-suite bedrooms, including a peaceful primary suite w/ fireplace, walk-in closet & spa-like bath. The 3rd level features the 4th en-suite bedroom, bonus room & full bath - an ideal retreat for an au pair, in-law or guests. Outside, your relaxation awaits w/ multiple patios for lounging, an in-ground pool, firepit & shower - designed for complete privacy & entertaining. Walk to beach, marina & vibrant downtown, train station, top rated schools, parks & dining - this home & location truly has it all!

634 S Benson 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

$2,500,000

Located in the coveted Greenfield Hill neighborhood, this exceptional property offers the perfect blend of weekend retreat and everyday living, just 60 miles from Manhattan. Set on over 2 private acres with classic stone walls, cedar roof, copper gutters and professional landscaping, the home welcomes you with a dramatic two-story foyer and 9-foot ceilings throughout. The designer living room flows seamlessly into a gorgeous dining room with custom paneling and continues through a gallery-style hallway to the stunning gourmet kitchen, featuring Sub-Zero refrigeration, Wolf gas cooktop, wall oven, pantry, and high-end finishes. Just off the kitchen is a charming shiplap mudroom with direct access to the garage. The kitchen opens to a cozy family room accented with newly added wood beams and fireplace. French door sliders lead to the backyard, creating an effortless indoor-outdoor connection. The second floor features a serene primary suite with a spacious walk-in closet and a spa-like bathroom offering a double vanity and oversized shower and . Additional spacious bedrooms share an impressive oversized full bath, and a dedicated laundry room completes the level. The above-ground finished lower level provides flexible living space, ideal for a home gym or additional entertaining area. Outdoors, the property truly shines with a gunite pool surrounded by bluestone, above-ground boxed gardens, and a level lawn space perfect for entertaining, recreation, or quiet relaxation,

4 Beds ⋅ 3 Baths ⋅ 24147180 MLS

Located in the coveted Greenfield Hill neighborhood, this exceptional property offers the perfect blend of weekend retreat and everyday living, just 60 miles from Manhattan. Set on over 2 private acres with classic stone walls, cedar roof, copper gutters and professional landscaping, the home welcomes you with a dramatic two-story foyer and 9-foot ceilings throughout. The designer living room flows seamlessly into a gorgeous dining room with custom paneling and continues through a gallery-style hallway to the stunning gourmet kitchen, featuring Sub-Zero refrigeration, Wolf gas cooktop, wall oven, pantry, and high-end finishes. Just off the kitchen is a charming shiplap mudroom with direct access to the garage. The kitchen opens to a cozy family room accented with newly added wood beams and fireplace. French door sliders lead to the backyard, creating an effortless indoor-outdoor connection. The second floor features a serene primary suite with a spacious walk-in closet and a spa-like bathroom offering a double vanity and oversized shower and . Additional spacious bedrooms share an impressive oversized full bath, and a dedicated laundry room completes the level. The above-ground finished lower level provides flexible living space, ideal for a home gym or additional entertaining area. Outdoors, the property truly shines with a gunite pool surrounded by bluestone, above-ground boxed gardens, and a level lawn space perfect for entertaining, recreation, or quiet relaxation,

200 Long Meadow Rd, Fairfield

$2,499,000

Perfectly positioned in the heart of the beach area, this stunning New Home offers the perfect blend of coastal living and in-town convenience. Ideally situated between the vibrant town center, beaches, and train - all just a short distance away - this property delivers an unmatched lifestyle. Built by Falzone Development a builder renowned for quality residential construction, this home showcases refined craftsmanship and high-end designer finishes rarely found in spec homes - details you'll notice from the moment you enter. The home features 5 bedrooms and 4.1 baths, with an open-concept layout ideal for modern living. The gourmet kitchen boasts a stunning oak island, custom cabinetry, Thermador appliances, quartz countertops and a stylish coffee bar flows seamlessly into the spacious family room with a gas fireplace. A dining room with butler's pantry and a private study complete the first floor. The luxurious primary suite offers a generous walk-in closet and spa-inspired bath with radiant-heat flooring. The finished third floor includes a bonus room and fifth bedroom, providing flexible space for guests, media, or play. The lower-level loggia opens to a stone patio, creating the perfect setting for outdoor entertaining, with ample room for a pool. Maintenance free exterior & Energy Eff. for low monthly expenses along with many smart home features. Experience coastal living at its finest - where craftsmanship, comfort, and location come together beautifully!

5 Beds ⋅ 5 Baths ⋅ 24146346 MLS

Perfectly positioned in the heart of the beach area, this stunning New Home offers the perfect blend of coastal living and in-town convenience. Ideally situated between the vibrant town center, beaches, and train - all just a short distance away - this property delivers an unmatched lifestyle. Built by Falzone Development a builder renowned for quality residential construction, this home showcases refined craftsmanship and high-end designer finishes rarely found in spec homes - details you'll notice from the moment you enter. The home features 5 bedrooms and 4.1 baths, with an open-concept layout ideal for modern living. The gourmet kitchen boasts a stunning oak island, custom cabinetry, Thermador appliances, quartz countertops and a stylish coffee bar flows seamlessly into the spacious family room with a gas fireplace. A dining room with butler's pantry and a private study complete the first floor. The luxurious primary suite offers a generous walk-in closet and spa-inspired bath with radiant-heat flooring. The finished third floor includes a bonus room and fifth bedroom, providing flexible space for guests, media, or play. The lower-level loggia opens to a stone patio, creating the perfect setting for outdoor entertaining, with ample room for a pool. Maintenance free exterior & Energy Eff. for low monthly expenses along with many smart home features. Experience coastal living at its finest - where craftsmanship, comfort, and location come together beautifully!

110 Pratt St, Fairfield

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