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Renovated 5 bedroom, 4.5 bath beach home with large loggia, gunite pool and large rooftop deck off the primary located one block from the beach on prime Lalley Boulevard.

5 Beds ⋅ 5 Baths ⋅ 24117597 MLS

Renovated 5 bedroom, 4.5 bath beach home with large loggia, gunite pool and large rooftop deck off the primary located one block from the beach on prime Lalley Boulevard.

365 Lalley Blvd, Fairfield

$3,100,000

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.

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

$3,100,000

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.

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

$3,100,000

New Construction in coveted BEACH AREA! This 4,000 sqft custom Colonial blends coastal charm with modern luxury, just a short walk to Penfield Beach, Fairfield Beach Club, vibrant downtown, train, & top rated schools. With 5 bedrooms, 4.5 baths, and 3 finished levels, this elevator ready home offers exceptional design, flow, and comfort. The open concept custom kitchen is both functional and beautiful with top of the line appliances, custom cabinetry, walk in pantry and Quartz countertops. The dining area has sliders to a spacious deck while the living room is the perfect space for entertaining or quiet night in. A butler's pantry with wet bar and second dishwasher leads to a sun filled flex room with fireplace, ideal for movie night or entertaining. Upstairs, the serene primary suite includes a spa-like bath with soaking tub, heated floors, two walk-in closets, and a Juliet balcony, perfect for taking in the breeze and the gentle sounds of nature. Two additional bedrooms enjoy private en-suite baths. The third floor offers 2 more bedrooms, a full bath, and a bonus space perfect for guests, an office, or a playroom. Enjoy quiet mornings on the covered third floor deck. Outside, enjoy a spacious yard with room for a pool or garden. The covered Le Nai is designed for year-round use-great for entertaining, lounging, or a home gym. A 2 car garage with tandem space offers ample parking. From beach walks to downtown dinners, this isn't just a home...it's a lifestyle!

5 Beds ⋅ 5 Baths ⋅ 24132638 MLS

New Construction in coveted BEACH AREA! This 4,000 sqft custom Colonial blends coastal charm with modern luxury, just a short walk to Penfield Beach, Fairfield Beach Club, vibrant downtown, train, & top rated schools. With 5 bedrooms, 4.5 baths, and 3 finished levels, this elevator ready home offers exceptional design, flow, and comfort. The open concept custom kitchen is both functional and beautiful with top of the line appliances, custom cabinetry, walk in pantry and Quartz countertops. The dining area has sliders to a spacious deck while the living room is the perfect space for entertaining or quiet night in. A butler's pantry with wet bar and second dishwasher leads to a sun filled flex room with fireplace, ideal for movie night or entertaining. Upstairs, the serene primary suite includes a spa-like bath with soaking tub, heated floors, two walk-in closets, and a Juliet balcony, perfect for taking in the breeze and the gentle sounds of nature. Two additional bedrooms enjoy private en-suite baths. The third floor offers 2 more bedrooms, a full bath, and a bonus space perfect for guests, an office, or a playroom. Enjoy quiet mornings on the covered third floor deck. Outside, enjoy a spacious yard with room for a pool or garden. The covered Le Nai is designed for year-round use-great for entertaining, lounging, or a home gym. A 2 car garage with tandem space offers ample parking. From beach walks to downtown dinners, this isn't just a home...it's a lifestyle!

450 Penfield Rd, Fairfield

$3,050,000

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

$3,004,000

Set in the coveted beach area of Fairfield, this gracious five - bedroom Center Hall colonial combines classic architecture character with exceptional privacy and beautifully appointed living spaces. Approached by stone walls and professionally landscaped grounds, the property offers a serene and inviting setting just moments from the beach. Inside, a welcoming center hall leads to generously proportioned rooms, while the cook's kitchen is designed for entertaining. The ceilings on the 1st floor are 9 foot with formal and informal living and dining areas. A large mudroom and half bath are located near the entrance to the garage. All five bedrooms are located on the 2nd floor. The primary bedroom has a full bath with soaking tub, shower and sauna. There are numerous closets and a sitting nook. There are 3 full baths on the 2nd floor with a laundry room. Throughout the home there are time-less details, built-ins, wainscoting and seating areas. This is a special Fairfield home that captures the best of relaxed coastal living. This home is minutes to the beach, Universities, town, train and 95.

5 Beds ⋅ 4 Baths ⋅ 24211346 MLS

Set in the coveted beach area of Fairfield, this gracious five - bedroom Center Hall colonial combines classic architecture character with exceptional privacy and beautifully appointed living spaces. Approached by stone walls and professionally landscaped grounds, the property offers a serene and inviting setting just moments from the beach. Inside, a welcoming center hall leads to generously proportioned rooms, while the cook's kitchen is designed for entertaining. The ceilings on the 1st floor are 9 foot with formal and informal living and dining areas. A large mudroom and half bath are located near the entrance to the garage. All five bedrooms are located on the 2nd floor. The primary bedroom has a full bath with soaking tub, shower and sauna. There are numerous closets and a sitting nook. There are 3 full baths on the 2nd floor with a laundry room. Throughout the home there are time-less details, built-ins, wainscoting and seating areas. This is a special Fairfield home that captures the best of relaxed coastal living. This home is minutes to the beach, Universities, town, train and 95.

108 Colonial Dr, 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

$3,000,000

Exquisite Beach-area home on over-sized, beautifully manicured 0.58-acre lot with frontage on Sunnie Holme Drive. Easy entry (no stairs) into this meticulously maintained, 5-bedroom home. Large, inviting Custom Kitchen with generous island, Sub-Zero, Thermador, and Miele appliances, beverage drawers, and spacious dining area. Well-planned Mudroom. Tranquil and elegant First Floor Primary Suite with new bath featuring radiant floor heating, soaking tub, double vanity. The gracious first floor, with 2246 square feet, is ideal for entertaining. Substantial Family Room with vaulted ceiling, wet bar, gas fireplace and sweeping staircase. Beautiful sight lines and easy access to the large, private backyard through multiple French doors. Elegant Living Room with fireplace. Well-appointed Dining Room with French doors. Formal entry with unique, custom paneled doors and walls. The second floor Suite with new full bath can be accessed via a back staircase and features an extra living space (great for guests, au pair, home office, playroom, etc). There are FIVE bedrooms in total: 1st floor Primary + 4 bedrooms and 3 full baths upstairs. Very large, private yard with stone patio, pergola and inviting fireplace. Room for pool. The circular driveway provides ample guest parking. A member of the Sunnie Holme Association, this property was once part of the much-admired gardens of Annie Burr Jennings' grand estate. No detail has been over-looked in this stunning home.

4 Beds ⋅ 5 Baths ⋅ 24089220 MLS

Exquisite Beach-area home on over-sized, beautifully manicured 0.58-acre lot with frontage on Sunnie Holme Drive. Easy entry (no stairs) into this meticulously maintained, 5-bedroom home. Large, inviting Custom Kitchen with generous island, Sub-Zero, Thermador, and Miele appliances, beverage drawers, and spacious dining area. Well-planned Mudroom. Tranquil and elegant First Floor Primary Suite with new bath featuring radiant floor heating, soaking tub, double vanity. The gracious first floor, with 2246 square feet, is ideal for entertaining. Substantial Family Room with vaulted ceiling, wet bar, gas fireplace and sweeping staircase. Beautiful sight lines and easy access to the large, private backyard through multiple French doors. Elegant Living Room with fireplace. Well-appointed Dining Room with French doors. Formal entry with unique, custom paneled doors and walls. The second floor Suite with new full bath can be accessed via a back staircase and features an extra living space (great for guests, au pair, home office, playroom, etc). There are FIVE bedrooms in total: 1st floor Primary + 4 bedrooms and 3 full baths upstairs. Very large, private yard with stone patio, pergola and inviting fireplace. Room for pool. The circular driveway provides ample guest parking. A member of the Sunnie Holme Association, this property was once part of the much-admired gardens of Annie Burr Jennings' grand estate. No detail has been over-looked in this stunning home.

160 Judson Rd, Fairfield

$3,000,000

Direct waterfront property with incomparable views across Southport Harbor, the Country Club of Fairfield golf course, and Long Island Sound. Generational opportunity to renovate or create your own vision in this most coveted of locations in historic Southport Village. Set high on a hill, the property faces due South for maximum light and views towards Long Island. Plentiful birdlife and boating activity in all seasons. Property features a circa 1939 Boathouse with bedroom and full bathroom, one of only 24 docks in the harbor, a 2 bedroom guest house and the 3,500 sq. foot main house. Walk to the village, train, and beach. Convenient to town centers of Fairfield and Westport. One hour to Manhattan.

5 Beds ⋅ 5 Baths ⋅ 170577246 MLS

Direct waterfront property with incomparable views across Southport Harbor, the Country Club of Fairfield golf course, and Long Island Sound. Generational opportunity to renovate or create your own vision in this most coveted of locations in historic Southport Village. Set high on a hill, the property faces due South for maximum light and views towards Long Island. Plentiful birdlife and boating activity in all seasons. Property features a circa 1939 Boathouse with bedroom and full bathroom, one of only 24 docks in the harbor, a 2 bedroom guest house and the 3,500 sq. foot main house. Walk to the village, train, and beach. Convenient to town centers of Fairfield and Westport. One hour to Manhattan.

319 Harbor Rd, Fairfield

$3,000,000

Unobstructed views of Long Island Sound, a bespoke beach path steps from your front door & a heated, saltwater, gunite pool w/waterfall framed by seagrass & sky--your Hamptons retreat awaits, right here in Fairfield County. Exquisite renovation completed in 2025 w/a refined coastal palette & curated designer finishes, this home is flooded w/natural light & features a show-stopping chef's kitchen w/eat-in breakfast area, oversized quartz island & countertops, custom inset cabinetry, new Thermador appliances & butlers pantry all designed for effortless entertaining poolside or fireside on the screened in porch. Expansive living room & family room w/coffered ceiling, gas fireplace & French doors to the deck create seamless indoor/outdoor flow. Formal dining room w/stunning millwork & sun-filled windows offers a crisp, coastal backdrop for entertaining. Upstairs are 4 bedrooms including primary suite w/sweeping Sound views, tray ceiling, private balcony & separate his and hers walk-in closets. Spa like bath w/radiant heat marble floors, double vanities, soaking tub, marble shower & private WC. Finished 3rd fl offers flexible space for 5th bedroom, home office or add'l family room w/large deck & views for days. Oversized 4 car garage w/epoxy floor, Tesla charging & plenty of room for gym or loggia. Outside, your seaside oasis awaits w/heated, saltwater, gunite pool w/waterfall, mult seating areas, & lush professional landscaping. 1 mile to train & downtown FFLD. Beachside bliss.

4 Beds ⋅ 4 Baths ⋅ 24103129 MLS

Unobstructed views of Long Island Sound, a bespoke beach path steps from your front door & a heated, saltwater, gunite pool w/waterfall framed by seagrass & sky--your Hamptons retreat awaits, right here in Fairfield County. Exquisite renovation completed in 2025 w/a refined coastal palette & curated designer finishes, this home is flooded w/natural light & features a show-stopping chef's kitchen w/eat-in breakfast area, oversized quartz island & countertops, custom inset cabinetry, new Thermador appliances & butlers pantry all designed for effortless entertaining poolside or fireside on the screened in porch. Expansive living room & family room w/coffered ceiling, gas fireplace & French doors to the deck create seamless indoor/outdoor flow. Formal dining room w/stunning millwork & sun-filled windows offers a crisp, coastal backdrop for entertaining. Upstairs are 4 bedrooms including primary suite w/sweeping Sound views, tray ceiling, private balcony & separate his and hers walk-in closets. Spa like bath w/radiant heat marble floors, double vanities, soaking tub, marble shower & private WC. Finished 3rd fl offers flexible space for 5th bedroom, home office or add'l family room w/large deck & views for days. Oversized 4 car garage w/epoxy floor, Tesla charging & plenty of room for gym or loggia. Outside, your seaside oasis awaits w/heated, saltwater, gunite pool w/waterfall, mult seating areas, & lush professional landscaping. 1 mile to train & downtown FFLD. Beachside bliss.

40 Fairfield Beach 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

$2,945,000

EXQUISITE COUNTRY COLONIAL - Located on one of the most desirable streets in all of Fairfield County, this absolutely exquisite, breathtakingly beautiful 4760 square foot (additional 700 square feet in the finished Lower Level), 4 Bedroom, three and one-half Bath Colonial features superb, custom millwork, classical architecture and proportions, designer finishes and elements, a stunning Terrace spanning the breadth of the house, and a magnificent, sweeping 3-acre property in the very heart of Greenfield Hill. This haven of beauty and tranquility is only minutes to fine dining, superb shopping and cultural venues, beaches, private and public schools and recreation, and Metro North Train Service to and from New York City. First Floor: Elegant Rotunda Foyer with hardwood flooring, and two Guest Closets. Powder Room with porcelain tile flooring and Pedestal Sink, and Staircase access to Terrace and Lower Level. Step down to Living Room with hardwood flooring, built-in glass paned Cabinet with drawers beneath, and Gas Log Fireplace. Sun Room with three exposures, hardwood flooring, French Doors opening onto Awning covered Terrace, barrel ceiling, Wet Bar with mirrored shelving, Nickel Sink and Refrigeration Drawers. Flower Room with tile flooring and access to Dining Terrace. Master Bedroom Suite with hardwood flooring, Gas Fireplace, Custom fitted Walk-in Closet, Dressing Room with two Closets, and Master Bath with . . . PLEASE OPEN ADDENDUM FOR FURTHER DESCRIPTION

4 Beds ⋅ 4 Baths ⋅ 24104351 MLS

EXQUISITE COUNTRY COLONIAL - Located on one of the most desirable streets in all of Fairfield County, this absolutely exquisite, breathtakingly beautiful 4760 square foot (additional 700 square feet in the finished Lower Level), 4 Bedroom, three and one-half Bath Colonial features superb, custom millwork, classical architecture and proportions, designer finishes and elements, a stunning Terrace spanning the breadth of the house, and a magnificent, sweeping 3-acre property in the very heart of Greenfield Hill. This haven of beauty and tranquility is only minutes to fine dining, superb shopping and cultural venues, beaches, private and public schools and recreation, and Metro North Train Service to and from New York City. First Floor: Elegant Rotunda Foyer with hardwood flooring, and two Guest Closets. Powder Room with porcelain tile flooring and Pedestal Sink, and Staircase access to Terrace and Lower Level. Step down to Living Room with hardwood flooring, built-in glass paned Cabinet with drawers beneath, and Gas Log Fireplace. Sun Room with three exposures, hardwood flooring, French Doors opening onto Awning covered Terrace, barrel ceiling, Wet Bar with mirrored shelving, Nickel Sink and Refrigeration Drawers. Flower Room with tile flooring and access to Dining Terrace. Master Bedroom Suite with hardwood flooring, Gas Fireplace, Custom fitted Walk-in Closet, Dressing Room with two Closets, and Master Bath with . . . PLEASE OPEN ADDENDUM FOR FURTHER DESCRIPTION

41 Cherry Ln, Fairfield

$2,940,000

Welcome to 46 Willow Street, a treasured Victorian jewel nestled on one of the best properties in the heart of Southport Village. This Circa 1890 home enjoys a gorgeous, private .41 acre with enchanting rose gardens, charming wrap-around porch and serene garden fountain. This distinguished home offers a perfect combination of timeless elegance and relaxed, welcoming ambiance. The foyer gracefully greets visitors with a beautifully designed stairway, setting the tone for the refined interior. The wonderful floor plan, accentuated by hardwood floors, is bright and open, featuring large windows inviting in natural light. The Library provides an ideal space to work or unwind, complete with extensive bookshelves and built-ins. Dining Room is a showstopper with stunning chandelier and Dutch door opening to Bar. Living Room has a corner fireplace and large bay window. The unique Family Room boasts a gallery of 15 windows and is a place for memorable gatherings. Den opens thru french doors to a terrific screened porch overlooking the fountain and gardens. The well-appointed Kitchen has top quality appliances. The sun-filled Breakfast Room opens to the screened porch and private patio, inviting the outdoors in. Upstairs, the Primary Bedroom includes a dressing room and full bath. There are 3 more bedrooms on this level. A rear staircase offers convenient access to walk-up attic. There is likely room for a pool. All just a short stroll to Harbor, Beach, Metro North Train & Restaurants

4 Beds ⋅ 3 Baths ⋅ 24013823 MLS

Welcome to 46 Willow Street, a treasured Victorian jewel nestled on one of the best properties in the heart of Southport Village. This Circa 1890 home enjoys a gorgeous, private .41 acre with enchanting rose gardens, charming wrap-around porch and serene garden fountain. This distinguished home offers a perfect combination of timeless elegance and relaxed, welcoming ambiance. The foyer gracefully greets visitors with a beautifully designed stairway, setting the tone for the refined interior. The wonderful floor plan, accentuated by hardwood floors, is bright and open, featuring large windows inviting in natural light. The Library provides an ideal space to work or unwind, complete with extensive bookshelves and built-ins. Dining Room is a showstopper with stunning chandelier and Dutch door opening to Bar. Living Room has a corner fireplace and large bay window. The unique Family Room boasts a gallery of 15 windows and is a place for memorable gatherings. Den opens thru french doors to a terrific screened porch overlooking the fountain and gardens. The well-appointed Kitchen has top quality appliances. The sun-filled Breakfast Room opens to the screened porch and private patio, inviting the outdoors in. Upstairs, the Primary Bedroom includes a dressing room and full bath. There are 3 more bedrooms on this level. A rear staircase offers convenient access to walk-up attic. There is likely room for a pool. All just a short stroll to Harbor, Beach, Metro North Train & Restaurants

46 Willow St, Fairfield

$2,900,000

THE SELLER REQUESTS THAT ALL OFFERS BE SUBMITTED NO LATER THAN SUNDAY, MARCH 16TH, AT 5 PM-- Nestled on a quiet cul-de-sac in one of Southport's most sought-after neighborhoods, this beautiful home offers a perfect blend of comfort, style, and modern convenience. Set on over two acres of manicured grounds, the property is designed for effortless indoor-outdoor living with a pool, hot tub, outdoor fire pit, pergola, and multiple terraces surrounded by lush gardens. Inside, the 5800+ sq. ft. home is bright and inviting, featuring high ceilings, hardwood floors, and thoughtfully designed spaces with natural light. The custom kitchen and library showcase exceptional quality and attention to detail. Recent updates include a butler's pantry, a newer roof and septic system, amenities like a whole-house generator, security cameras, a Tesla charger, and a misting system at the pool for warm summer days. The pool house is a standout, complete with a mini kitchen, wine fridge, beer tap, dishwasher, microwave, and even a washer and dryer, making it easy to enjoy weekends by the pool without leaving home. The walk-up attic offers a house-length of storage and many other possibilities. Located just minutes from Southport Village, train stations, and the best of Fairfield and Westport, this home offers a peaceful setting with easy access to everything the area offers.

5 Beds ⋅ 5 Baths ⋅ 24078680 MLS

THE SELLER REQUESTS THAT ALL OFFERS BE SUBMITTED NO LATER THAN SUNDAY, MARCH 16TH, AT 5 PM-- Nestled on a quiet cul-de-sac in one of Southport's most sought-after neighborhoods, this beautiful home offers a perfect blend of comfort, style, and modern convenience. Set on over two acres of manicured grounds, the property is designed for effortless indoor-outdoor living with a pool, hot tub, outdoor fire pit, pergola, and multiple terraces surrounded by lush gardens. Inside, the 5800+ sq. ft. home is bright and inviting, featuring high ceilings, hardwood floors, and thoughtfully designed spaces with natural light. The custom kitchen and library showcase exceptional quality and attention to detail. Recent updates include a butler's pantry, a newer roof and septic system, amenities like a whole-house generator, security cameras, a Tesla charger, and a misting system at the pool for warm summer days. The pool house is a standout, complete with a mini kitchen, wine fridge, beer tap, dishwasher, microwave, and even a washer and dryer, making it easy to enjoy weekends by the pool without leaving home. The walk-up attic offers a house-length of storage and many other possibilities. Located just minutes from Southport Village, train stations, and the best of Fairfield and Westport, this home offers a peaceful setting with easy access to everything the area offers.

200 Jessica Ln, 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

$2,850,000

Welcome to "The Millstones" an exquisite classic revival completely transformed for today's living. Rebuilt by Cameron Clark (1923) this historic & architecturally significant home has been lovingly updated and restored by current owners. Gorgeous foyer with coffered paneling, views of the magnificent grounds and access to expansive formal living room with curved mantel fireplace, wetbar & French doors to terrace. Updated kitchen featuring Calacatta Statuario quartz countertops & backsplash, new appliances including Viking, Wolf range, 2 dishwashers, wine fridge & butlers pantry. Sunlit breakfast room w/ tumbled marble and Serena & Lily lighting. Formal dining room w/ fpl offers the perfect setting for memorable family dinners or entertaining with friends. Floor-to-ceiling French doors frame views of the gardens, terrace, pool and pond. Library w/ fireplace & builtins, WFH becomes effortless in dedicated first floor office. Playroom directly off kitchen plus large family room over the garage is perfect space for enjoying the Super Bowl with a crowd. Upstairs, the primary suite is a sanctuary unto itself, w/ marble fpl, all new master bath w/ honed Calcutta marble, steam shower,freestanding tub,WC. 2 add'l ensuite BRs + 5th BR/office located near primary bedroom. A fully renovated guest suite w/ sitting room is privately set w/ back stair access. New cedar roof, int/ext painting, Sonos. OAR is easily one of the most coveted locations to call home, conv to town, train and NYC.

4 Beds ⋅ 7 Baths ⋅ 170595290 MLS

Welcome to "The Millstones" an exquisite classic revival completely transformed for today's living. Rebuilt by Cameron Clark (1923) this historic & architecturally significant home has been lovingly updated and restored by current owners. Gorgeous foyer with coffered paneling, views of the magnificent grounds and access to expansive formal living room with curved mantel fireplace, wetbar & French doors to terrace. Updated kitchen featuring Calacatta Statuario quartz countertops & backsplash, new appliances including Viking, Wolf range, 2 dishwashers, wine fridge & butlers pantry. Sunlit breakfast room w/ tumbled marble and Serena & Lily lighting. Formal dining room w/ fpl offers the perfect setting for memorable family dinners or entertaining with friends. Floor-to-ceiling French doors frame views of the gardens, terrace, pool and pond. Library w/ fireplace & builtins, WFH becomes effortless in dedicated first floor office. Playroom directly off kitchen plus large family room over the garage is perfect space for enjoying the Super Bowl with a crowd. Upstairs, the primary suite is a sanctuary unto itself, w/ marble fpl, all new master bath w/ honed Calcutta marble, steam shower,freestanding tub,WC. 2 add'l ensuite BRs + 5th BR/office located near primary bedroom. A fully renovated guest suite w/ sitting room is privately set w/ back stair access. New cedar roof, int/ext painting, Sonos. OAR is easily one of the most coveted locations to call home, conv to town, train and NYC.

745 Old Academy Rd, Fairfield

$2,839,000

Just completed! This modern stone and shingle colonial was meticulously designed for today’s demanding families who desire a beautiful space to live comfortably, work, and entertain. You will not outgrow this exquisite 8,000 SF home! Nestled in a private Southport enclave, this remarkable property was custom built by the renowned J.Tallman Builders and over the last 2 years has had a top-to-bottom renovation. Grand in scale with elegance and sophistication, the interior exudes modern energy with an open floor plan. The bright kitchen with 10ft island opens into a 2-story great room with stone fireplace and soaring ceilings. The main level also features a 1,000 SF private office wing with spacious lounge and wet bar. The upper level has 5 large bedrooms, each with walk-in closet and en suite bathroom, and expansive loft. A walk-up attic can be finished with over 1,000 SF of additional living space. The newly completed lower level includes a fitness center, entertainment room, game room, 2nd office/guest bedroom, full bath. Magnificent landscaping, an outdoor covered patio with chef’s kitchen, and tranquil views of the pond will impress guests and will create life-long memories. A location for a pool is incorporated in an updated survey & RI Pools can install in May/June 2024. This is a one-of-a-kind home in a great location near Southport Village, Fairfield and Westport downtowns, beaches, and award-winning schools. The cost to replicate today would be $4+Million. See Addendum

5 Beds ⋅ 8 Baths ⋅ 170571453 MLS

Just completed! This modern stone and shingle colonial was meticulously designed for today’s demanding families who desire a beautiful space to live comfortably, work, and entertain. You will not outgrow this exquisite 8,000 SF home! Nestled in a private Southport enclave, this remarkable property was custom built by the renowned J.Tallman Builders and over the last 2 years has had a top-to-bottom renovation. Grand in scale with elegance and sophistication, the interior exudes modern energy with an open floor plan. The bright kitchen with 10ft island opens into a 2-story great room with stone fireplace and soaring ceilings. The main level also features a 1,000 SF private office wing with spacious lounge and wet bar. The upper level has 5 large bedrooms, each with walk-in closet and en suite bathroom, and expansive loft. A walk-up attic can be finished with over 1,000 SF of additional living space. The newly completed lower level includes a fitness center, entertainment room, game room, 2nd office/guest bedroom, full bath. Magnificent landscaping, an outdoor covered patio with chef’s kitchen, and tranquil views of the pond will impress guests and will create life-long memories. A location for a pool is incorporated in an updated survey & RI Pools can install in May/June 2024. This is a one-of-a-kind home in a great location near Southport Village, Fairfield and Westport downtowns, beaches, and award-winning schools. The cost to replicate today would be $4+Million. See Addendum

805 Cedar Rd, Fairfield

$2,800,000

Paradise awaits at this extraordinary, magazine-worthy masterpiece set on 2 level acres on a coveted cul-de-sac in lower Greenfield Hill. This 5 bedroom home redefines luxury w/its impeccable blend of timeless elegance & captivates w/exquisite grounds & designer interiors. Step inside to a brilliant open-concept layout flooded w/natural light from oversized windows & French doors seamlessly blending indoor & outdoor living. Breathtaking family room w/beamed, vaulted ceilings, floor-to-ceiling windows, fieldstone fireplace & dual French doors opening to expansive bluestone patio. Swoon-worthy formal living room w/cozy gas fireplace & home office w/walls of windows, vaulted ceiling & custom built-ins. Elegant formal dining room flows into completely remodeled gourmet kitchen w/custom cabinetry, Sub-Zero & Thermador appliances, spacious pantry, ample island seating & chic breakfast area. Upstairs retreat to exquisite primary suite; a true sanctuary w/vaulted ceilings, deck, skylights & separate sitting room w/fireplace & walk-in closet. Massive game room & 3 additional generously sized bedrooms. Finished lower level w/family room, gym & versatile finished space. Outside, a true country club oasis w/professionally landscaped grounds, stunning antique barn, sport court, oversized heated gunite pool w/auto cover, bluestone patio w/firepit and multiple seating areas creating an unparalleled setting. A once in a lifetime opportunity awaits, your private paradise is here.

5 Beds ⋅ 5 Baths ⋅ 24048555 MLS

Paradise awaits at this extraordinary, magazine-worthy masterpiece set on 2 level acres on a coveted cul-de-sac in lower Greenfield Hill. This 5 bedroom home redefines luxury w/its impeccable blend of timeless elegance & captivates w/exquisite grounds & designer interiors. Step inside to a brilliant open-concept layout flooded w/natural light from oversized windows & French doors seamlessly blending indoor & outdoor living. Breathtaking family room w/beamed, vaulted ceilings, floor-to-ceiling windows, fieldstone fireplace & dual French doors opening to expansive bluestone patio. Swoon-worthy formal living room w/cozy gas fireplace & home office w/walls of windows, vaulted ceiling & custom built-ins. Elegant formal dining room flows into completely remodeled gourmet kitchen w/custom cabinetry, Sub-Zero & Thermador appliances, spacious pantry, ample island seating & chic breakfast area. Upstairs retreat to exquisite primary suite; a true sanctuary w/vaulted ceilings, deck, skylights & separate sitting room w/fireplace & walk-in closet. Massive game room & 3 additional generously sized bedrooms. Finished lower level w/family room, gym & versatile finished space. Outside, a true country club oasis w/professionally landscaped grounds, stunning antique barn, sport court, oversized heated gunite pool w/auto cover, bluestone patio w/firepit and multiple seating areas creating an unparalleled setting. A once in a lifetime opportunity awaits, your private paradise is here.

201 Queens Grant Rd, Fairfield

$2,790,000

This stunning, like-new home on Southport's Heather Ridge features 5 bedrooms and 5.5 baths, capturing the essence of traditional living and style. Upon entering the front door, the grand foyer leads to the sun-drenched great room with 2-story walls of windows anchored by a gas fireplace. The adjacent gourmet kitchen features Sub-Zero and Wolf appliances, while an additional bedroom/office completes the 1st floor. The beautiful 2nd-floor landing provides front-to-back views that lead to an expansive primary suite and dressing room with walk-in closets and a relaxing spa bathroom. Three additional bedrooms and two full baths are located on the 2nd floor. The finished 3rd floor offers far-reaching views of the Long Island Sound. A fabulous walkout leads to the finished lower level, which includes a 6th bedroom suite converted into a comfy home theater and recreation or exercise room. A Gunite heated pool with a whirlpool spa is located in the beautifully landscaped private backyard that looks to a private nature reserve for ultimate privacy. Enjoy the best of Southport living, close to the train, Southport Harbor, Southport Village's charming shops, restaurants, Sasco Beach, and an easy commute to I-95.

5 Beds ⋅ 6 Baths ⋅ 24017919 MLS

This stunning, like-new home on Southport's Heather Ridge features 5 bedrooms and 5.5 baths, capturing the essence of traditional living and style. Upon entering the front door, the grand foyer leads to the sun-drenched great room with 2-story walls of windows anchored by a gas fireplace. The adjacent gourmet kitchen features Sub-Zero and Wolf appliances, while an additional bedroom/office completes the 1st floor. The beautiful 2nd-floor landing provides front-to-back views that lead to an expansive primary suite and dressing room with walk-in closets and a relaxing spa bathroom. Three additional bedrooms and two full baths are located on the 2nd floor. The finished 3rd floor offers far-reaching views of the Long Island Sound. A fabulous walkout leads to the finished lower level, which includes a 6th bedroom suite converted into a comfy home theater and recreation or exercise room. A Gunite heated pool with a whirlpool spa is located in the beautifully landscaped private backyard that looks to a private nature reserve for ultimate privacy. Enjoy the best of Southport living, close to the train, Southport Harbor, Southport Village's charming shops, restaurants, Sasco Beach, and an easy commute to I-95.

10 Meadow Ridge Rd, Fairfield

$2,755,000

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

5 Beds ⋅ 5 Baths ⋅ 24166236 MLS

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

790 Cedar Brook Ln, Fairfield

$2,750,000

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

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