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260 Willow St, Fairfield
$12,000,000
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
378 Penfield Rd, Fairfield
$4,300,000
6 Beds ⋅ 6 Baths ⋅ 24155905 MLS
IMAGES FROM BUILDER'S PORTFOLIO.Remarkable CUSTOMIZABLE approx 6,000 Sqft New Beach Construction Home on a very RARE OVERSIZED 0.31 acre lot with a non-pareil luxurious Open floor plan on the Premier street in beach area ! Situated just two blocks away from Penfield Beach. Created by Master Local Builder; NEW GENERATION HEALTHY HOMES. Custom designed to offer state of the art amenities, 7 bedrooms, 5 baths, library with exceptional trim work and french doors leading to an outdoor covered porch and inviting blue stone patio. Expansive family room with welcoming fireplace and grand living room with a second fireplace for festive family celebrations. Chef's kitchen with custom cabinetry and top of the line appliances offers a separate eating area with bay windows. Bedrooms are generously sized with full marble baths and top quality vanities. Opulent master suite provides a perfect place to retreat. The finished third floor with additional living space will surely suits your family and Lifestyle. Two extra generously sized bedrooms, a full bath, room for a movie theater, a playroom or gym complete this unique oversized beach sanctuary. OPTIONS available: Sauna, Elevator, Wine parlor, Outdoor loggia and Pool. LAND OF 0.31 ACRE IS RARE and OVERSIZED. A TRUE GEM. Please note that is project is a proposed built and that the pictures depicted here are from local and renowned builder NewGenerationHealthyHomes. Inquire today to view or request builder's extensive portfolio and finishes

378 Penfield Rd, Fairfield
800 Verna Hill Rd, Fairfield
$4,250,000
4 Beds ⋅ 8 Baths ⋅ 24180502 MLS
Set on one of Fairfield's most coveted streets, this is the kind of home families spend years hoping will become available. Set on 3.35 acres on prestigious Verna Hill Road, adjacent to Fairfield Country Day School, this is the kind of property that becomes the backdrop for decades of memories. Summer afternoons by the pool and spa. Holiday dinners that bring everyone together. At the center of it all is a home that balances grandeur with warmth. The gracious living and dining rooms, with their soaring ceilings, were made for entertaining, while the sunroom and family room naturally become gathering places, overlooking the pool, patio, and grounds. Tucked away, a richly paneled office with fireplace and French doors opening to a private garden provides a quiet retreat. The four bedrooms are all en-suite, with the primary offering his and her baths and dressing rooms, along with the convenience of an elevator. Connected by a breezeway, the detached three-car garage is topped by a 1,000 sqft studio apartment (5th bedroom) with a kitchen, full bath, and washer and dryer-ideal for au-pair, extended family or gym. Outside, resort-style amenities include a pool, spa, expansive terraces overlooking the flat manicured backyard. Properties like this are increasingly rare: timeless architecture, one of Fairfield's most coveted addresses, all just minutes from town, beaches, and country clubs.

800 Verna Hill Rd, Fairfield
153 Birch Rd, Fairfield
$4,200,000
5 Beds ⋅ 4 Baths ⋅ 24170280 MLS
Location, Location, Location plus an exceptional design all come together at 153 Birch Road. Ideally located in one of the most sought-after Beach neighborhoods, this FEMA compliant home sits on a rare level, stunning, .34-acre lot and offers over 4800 square feet of high end, solid construction and brilliant architecture. Features that make this home a true stand out include 11 spacious rooms including 5 bedrooms along with custom details and impressive recent upgrades throughout. Step outside to your own true hidden paradise complete with a Gunite pool, outdoor kitchen, shower, multiple patios and seating areas filled with vibrant, colorful plantings with professional landscaping. A third-floor walkup provides exciting expansion potential offering over 1000 square feet of unfinished space currently being used for storage. Seconds to the elementary school and an easy stroll to miles of sandy beaches, town, parks, beach clubs and so much more. This stunning home delivers the best of the best.

153 Birch Rd, Fairfield
129 Quarter Horse Ln, Fairfield
$3,900,000
6 Beds ⋅ 7 Baths ⋅ 24165267 MLS
Tucked away on a quiet cul-de-sac in the heart of Greenfield Hill,this exceptional 7,100-sqft estate is set on two meticulously landscaped acres,offering a rare blend of timeless elegance & modern luxury.A sweeping two-tiered bluestone terrace frames the stunning 20'x40' heated gunite pool,creating a private outdoor sanctuary designed for both relaxation & grand-scale entertaining.Completely reimagined by an award-winning local builder in 2015,every finish & detail has been thoughtfully curated with an uncompromising eye for quality,craftsmanship,& design.Spanning 4 finished levels,the home offers 5-6 bedrooms;luxurious primary suites on both the 1st & 2nd floors,ideal for multigenerational living or accommodating guests with ease.Refined architectural elements & bespoke millwork enhance the home's stately presence,while a seamless flow of formal & informal spaces elevates everyday living.Designed for effortless entertaining, the gracious formal living room & the elegant dining room both feature gas fireplaces.The classic butler's pantry is complemented by a stylish wet bar. The chef's kitchen is a showpiece,featuring a dramatic 10-ft island with 2" Calacutta marble,dual sinks,premium appliances & a coffered ceiling,all opening to a spectacular 2-story family room anchored by a floor-to-ceiling stone fireplace.

129 Quarter Horse Ln, Fairfield
349 Beach Rd, Fairfield
$3,600,000
5 Beds ⋅ 5 Baths ⋅ 24175220 MLS
OPEN HOUSE TODAY HAS BEEN CANCELED. 349 Beach Road is the kind of home that instantly slows the pace of life - where mornings begin with walks to the beach, afternoons are spent by the pool beneath coastal skies, and evenings gather naturally around the warmth of the fire. Just moments from Fairfield's shoreline, the home offers a lifestyle that feels both relaxed and effortlessly elevated. Thoughtfully reimagined over time, the residence blends timeless character with refined modern living. Extensive updates and renovations completed throughout the past five years have elevated nearly every corner of the home while preserving its historic soul. Sunlight pours through open gathering spaces designed for connection and entertaining, while exposed antique beams, heart pine floors, and multiple fireplaces create warmth and authenticity throughout. The expanded kitchen serves as the heart of the home - a place for lingering dinners, holiday traditions, and everyday moments that feel special. Outside, the grounds feel private and resort-inspired, framed by mature landscaping and lush laurel plantings, with seamless indoor-outdoor flow to the newly added pool, stone terraces, and beautifully designed outdoor spaces. Whether hosting summer gatherings after a day by the water or enjoying quiet evenings under the glow of landscape lighting, every space was designed for effortless living. 3

349 Beach Rd, Fairfield
345 Old Dam Rd, Fairfield
$3,500,000
4 Beds ⋅ 4 Baths ⋅ 24150388 MLS
A beautiful, new construction WATERFRONT home complete w/ BOAT DOCK, ROOFTOP & ELEVATOR awaits & will be ready for you to enjoy by June. Offering 3 levels of luxurious living - this gorgeous coastal home sets a new standard for smart design & top tier craftsmanship. Enjoy seamless access to every floor w/ a private elevator from the ground to the 3rd level PLUS a stairway to an additional rooftop deck where you can enjoy unobstructed panoramic water views & colorful sunsets. With 10 spacious rooms, this home combines comfort, elegance & functionality. The ground level loggia opens up to the water, while the private dock in front of your home offers in the moment convenience for boaters. Across the road, your own additional property provides great extra parking - a rare bonus in waterfront living. Every detail reflects luxury; white oak hardwood flooring, Pella Lifestyle series wood interior windows, custom interior doors, state of the art appliances including wine column & beverage chiller, custom cabinetry in kitchen & baths, Hardie Board exterior siding for lasting durability, decks on 2nd, 3rd & rooftop levels all w/ stunning views, radiant heated flooring in the ground-level entry & primary bath & spa-like bathrooms w/ premium finishes. This home is flooded w/ natural light throughout the day, enhancing your daily living. Living life with quality!

345 Old Dam Rd, Fairfield
475 Fence Row Dr, Fairfield
$3,425,000
4 Beds ⋅ 8 Baths ⋅ 24200803 MLS
Set well back from the road on two acres in Greenfield Hill, this remarkable residence is approached by a tree-lined drive of pavers, cobblestone and Belgian block. Completely rebuilt and reimagined with the quality and craftsmanship of new construction, nearly 8,000 square feet unfold across three levels with four bedrooms, six full and two half baths, wide-plank oak floors, expansive windows and tranquil pond views. A sun-filled atrium with soaring 20-foot ceilings introduces gracious living and entertaining spaces accented by multiple fireplaces. The tremendous chef's kitchen features quartzite surfaces, abundant cabinetry, a walk-in pantry and Sub-Zero, Wolf and Miele appliances, including dual refrigeration, ovens and dishwashers. The primary suite features a barrel-vaulted ceiling, fireplace and separate his-and-hers areas, each with a walk-in closet and private marble bath with heated floors. Two additional en suite bedrooms and laundry complete the upper level. The light-filled walkout lower level includes a fireplace, kitchenette, wine room, full bath, exercise room, second laundry and flexible recreation/media space. Terraces with a fire pit and built-in grill overlook the peaceful grounds. Smart-home technology, a generator, all-new systems and a standing-seam metal roof add turnkey ease. The Ridge offers a staffed gated entrance, private roads, mature trees, clubhouse, heated pool, tennis and pickleball.

475 Fence Row Dr, Fairfield
145 Galloping Hill Rd, Fairfield
$3,300,000
5 Beds ⋅ 6 Baths ⋅ 24161914 MLS
Exceptional scale and timeless elegance define this impressive 5-bedroom, 6-bath residence offering over 8,200 square feet of refined living space in one of Fairfield's most desirable locations. Thoughtfully designed for both grand entertaining and comfortable everyday living, the home features expansive sun-filled rooms, high ceilings, and a seamless flow throughout the main living areas. A spacious chef's kitchen opens to inviting gathering spaces, while multiple formal and informal rooms provide flexibility for today's lifestyle. Generously sized bedrooms include a luxurious primary suite designed as a private retreat. The home's substantial footprint allows for ideal work-from-home options, recreation areas, and guest accommodations. Set on a beautifully landscaped property, the outdoor space offers privacy and room to enjoy the serene surroundings. Conveniently located near Fairfield's vibrant downtown, beaches, train access, dining, and top amenities, this property presents a rare opportunity to own a home of significant size and presence in a premier Fairfield setting.

145 Galloping Hill Rd, Fairfield
817 Sasco Hill Rd, Fairfield
$3,200,000
24169366 MLS
BUILDING OPPORTUNITY ATOP SASCO HILL - This stunning 2-acre parcel atop Sasco Hill, the pinnacle, presents a unique opportunity to build a sensational estate while enjoying captivating views of Southport Harbor and the Norwalk Islands. The exceptional Sasco Hill Road location provides not only privacy but also an extraordinary canvas for a luxurious custom residence, characterized by expansive lawns, and southern vistas of Long Island Sound; all within walking distance of Sasco Beach. Adding character and a touch of history to this remarkable site, the property features a historic stone foundation of an early Onion Barn. And, the surrounding amenities of charming Southport Village and vibrant Fairfield Center are just minutes away, ensuring convenience to Metro North Train Service, and access to great dining, shopping, and cultural experiences. Transform this idyllic setting into your personal sanctuary in one of Fairfield County's most beautiful locations. NEW TAX ASSESSMENT IS $2,123,730. ANY AND ALL STRUCTURES BEING SOLD IN "AS IS" CONDITION.

817 Sasco Hill Rd, Fairfield
679 Rowland Rd, Fairfield
$3,150,000
4 Beds ⋅ 4 Baths ⋅ 24196292 MLS
Ideally located in one of Fairfield's most desirable beach neighborhoods, this beautiful custom-built FEMA compliant home combines premium construction and efficiency with high-end finishes throughout. Unique features include 2x6 framing, steel beam support, energy efficient foam insulation, dual HVAC and tankless hot water systems, a gorgeous custom kitchen with Thermador appliances and honed granite countertops, an incredible home theater system, a 3-floor elevator, a spacious bonus room with views of Long Island Sound, an oversized garage with a gym or if you prefer, space for a 3rd car; and to top it all off, a saltwater swim spa overlooking a lush, professionally landscaped yard. Just steps to deeded beach access, and minutes to the playground, tennis and bocce courts, Fairfield's vibrant town center and Metro North train station. This stunning home isn't going to last - schedule your showing before it's gone.

679 Rowland Rd, Fairfield
274 Pine Creek Ave, Fairfield
$3,100,000
2 Beds ⋅ 3 Baths ⋅ 24147983 MLS
Waterfront summer living! This slice of heaven features 2-3 bedrooms, 2.5 bathrooms, and a detached studio apartment with a full bath. This modern architectural masterpiece, designed by award winning architect, Roger Ferris, has breathtaking views and an abundance of natural light, courtesy of the expansive floor to ceiling windows in every room. The dreamy primary bedroom has panoramic water views with the Manhattan skyline in the distance. The second bedroom contains a loft which provides two separate, private sleeping nooks and a lounge area with two-story, floor to ceiling windows. The detached studio apartment makes an ideal option for guests or extra recreational space with a wet bar and loft. The spacious exterior offers ample yard and deck space directly on the water for abundant outdoor living opportunities. Walk to the sandy beach from your yard at low tide or stroll down your sleepy street to the beach access path. This unique home's private, tranquil, waterfront setting makes it hard to believe it is so close to town, Metro North, and 95 for easy commuting, shopping, and dining in beautiful Fairfield.

274 Pine Creek Ave, Fairfield
2683 Bronson Rd, Fairfield
$3,100,000
5 Beds ⋅ 7 Baths ⋅ 24158967 MLS
In the heart of Greenfield Hill proper at the top of Bronson Road, this special and truly unique estate presents a rare opportunity in one of Fairfield's most coveted locations. Set on just over two acres of beautifully landscaped, professionally photographed grounds, the property reflects a timeless elegance that would be costly to replicate today. Across from a distinguished equestrian family compound and abutting the Greenfield Hill Historic District, the setting offers both distinction and privacy. This historic home has been thoughtfully expanded, restored, and renovated over the years, blending irreplaceable old world craftsmanship with modern comfort. High ceilings, wide plank floors, intricate moldings, arched entries, and abundant natural light create a refined yet inviting atmosphere. Notable spaces include a cherry library, formal dining room, gracious family and living rooms anchored by two brick chimneys and five fireplaces, an expansive kitchen, and elegant entertaining areas throughout. Outdoors, enjoy a bluestone patio with pergola, ideal for al fresco dining and relaxed gatherings. Adding to the property's uniqueness is a recently rebuilt pool house featuring a kitchenette, family room, recreation room, art studio, home office, and 1.5 baths. The romantic keyhole shaped gunite pool is framed by stone walls and lush gardens, creating a private retreat.

2683 Bronson Rd, Fairfield
1053 Fairfield Beach Rd, Fairfield
$3,050,000
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
598 S Benson Rd, Fairfield
$3,015,000
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
111 Golden Pond Ln, Fairfield
$3,000,000
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
1380 Old Academy Rd, Fairfield
$3,000,000
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
40 Hill Brook Ln, Fairfield
$2,995,000
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
171 Paddock Hill Ln, Fairfield
$2,950,000
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
550 Penfield Rd, Fairfield
$2,875,000
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
127 Field Rock Rd, Fairfield
$2,875,000
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
1123 Round Hill Rd, Fairfield
$2,850,000
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
309 Birch Rd, Fairfield
$2,850,000
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
750 Burr St, Fairfield
$2,850,000
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
790 Cedar Brook Ln, Fairfield
$2,755,000
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
131 Sasco Hill Rd, Fairfield
$2,750,000
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
342 Midlock Rd, Fairfield
$2,750,000
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
70 Meadow Ridge Rd, Fairfield
$2,730,000
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
1871 Fairfield Beach Rd, Fairfield
$2,725,000
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
28 Center St, Fairfield
$2,700,000
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

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