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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.

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

$3,900,000

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.

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

$3,425,000

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.

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

$3,300,000

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.

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

$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

$3,000,000

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

$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

$2,850,000

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

$2,750,000

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

5 Beds ⋅ 7 Baths ⋅ 24134949 MLS

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

342 Midlock Rd, Fairfield

$2,650,000

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

5 Beds ⋅ 6 Baths ⋅ 24188324 MLS

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

73 Foggwood Cir, Fairfield

$2,495,000

A Connecticut Classic - this center hall Colonial is located on the most charming stretch in Greenfield Hill. Beautifully set on 2 acres, this 4 bedroom Jack Franzen designed home lives large in all aspects. Guests are welcomed into the double height foyer flanked by formal living and dining rooms. The great room spans the back of the house combining a gorgeous light, bright & well appointed kitchen, with a cozy family room w/ traditional fireplace & plenty of room for gathering & lounging, a dining area and a cozy window seat - and easy access to the huge recreation room set over the garage! The first floor also holds a lovely library room with another fireplace, beautiful, oversized windows facing both front and back views and custom built-ins. Upstairs, the primary bedroom is spacious and light-filled, with a recently renovated bath and walk in closet. There is an ensuite bedroom plus two additional bedrooms sharing a hall bath. Outdoor living is maximized with two deck spaces and a pretty patio, perfect for entertaining, grilling and enjoying the privacy of the gorgeous, fenced in grounds! True New England character is felt throughout, from the rich hardwoods, charming wainscotting & coastal chic kitchen to the historical neighborhood setting - imagine spring days on the green celebrating the Dogwood Festival, sounds of baseball being played at the nearby diamond all while also being centrally located to all Fairfield amenities like beach, town and train to NYC!

4 Beds ⋅ 4 Baths ⋅ 24186223 MLS

A Connecticut Classic - this center hall Colonial is located on the most charming stretch in Greenfield Hill. Beautifully set on 2 acres, this 4 bedroom Jack Franzen designed home lives large in all aspects. Guests are welcomed into the double height foyer flanked by formal living and dining rooms. The great room spans the back of the house combining a gorgeous light, bright & well appointed kitchen, with a cozy family room w/ traditional fireplace & plenty of room for gathering & lounging, a dining area and a cozy window seat - and easy access to the huge recreation room set over the garage! The first floor also holds a lovely library room with another fireplace, beautiful, oversized windows facing both front and back views and custom built-ins. Upstairs, the primary bedroom is spacious and light-filled, with a recently renovated bath and walk in closet. There is an ensuite bedroom plus two additional bedrooms sharing a hall bath. Outdoor living is maximized with two deck spaces and a pretty patio, perfect for entertaining, grilling and enjoying the privacy of the gorgeous, fenced in grounds! True New England character is felt throughout, from the rich hardwoods, charming wainscotting & coastal chic kitchen to the historical neighborhood setting - imagine spring days on the green celebrating the Dogwood Festival, sounds of baseball being played at the nearby diamond all while also being centrally located to all Fairfield amenities like beach, town and train to NYC!

3050 Bronson Rd, Fairfield

$2,335,000

Enchanting countrystyle retreat offering the warmth of a welcoming neighborhood with the luxury of natural privacy, nestled amid professionally landscaped gardens and mature trees. Designed for gracious living and effortless entertaining, 165 Hemlock Hills S blends refined upgrades with modern comfort throughout. Featuring two primary suites, five bedrooms, and four beautifully renovated baths, the home centers around a stunning NuKitchens renovation with custom Plain & Fancy cabinetry, SubZero column refrigerator and freezer, quartz countertops, island and banquette seating, plus new laundry room. Enlarged doorways invite sunlight and frame serene pool and garden views, creating a seamless indoor/outdoor connection. Multiple living spaces support every lifestyle moment: a fireside living room, dramatic dining room, family room with stone fireplace, sunroom wrapped in windows, and a media room with beverage bar. New trim, lighting, and elevated decor add quiet sophistication throughout. Basement playroom offers flexible space. Outside, the resort-inspired backyard is a private escape, with newer Trex deck and fences, poolside patio, fire pit for evenings into late fall, winding gravel paths, and lush seasonal landscaping. Well water available for pool; home has city water. Newer driveway, roof, furnace, water purification system. Peaceful, private, and beautifully connected-just five minutes to Trader Joe's and highway access. A home for how you live today.

5 Beds ⋅ 4 Baths ⋅ 24159832 MLS

Enchanting countrystyle retreat offering the warmth of a welcoming neighborhood with the luxury of natural privacy, nestled amid professionally landscaped gardens and mature trees. Designed for gracious living and effortless entertaining, 165 Hemlock Hills S blends refined upgrades with modern comfort throughout. Featuring two primary suites, five bedrooms, and four beautifully renovated baths, the home centers around a stunning NuKitchens renovation with custom Plain & Fancy cabinetry, SubZero column refrigerator and freezer, quartz countertops, island and banquette seating, plus new laundry room. Enlarged doorways invite sunlight and frame serene pool and garden views, creating a seamless indoor/outdoor connection. Multiple living spaces support every lifestyle moment: a fireside living room, dramatic dining room, family room with stone fireplace, sunroom wrapped in windows, and a media room with beverage bar. New trim, lighting, and elevated decor add quiet sophistication throughout. Basement playroom offers flexible space. Outside, the resort-inspired backyard is a private escape, with newer Trex deck and fences, poolside patio, fire pit for evenings into late fall, winding gravel paths, and lush seasonal landscaping. Well water available for pool; home has city water. Newer driveway, roof, furnace, water purification system. Peaceful, private, and beautifully connected-just five minutes to Trader Joe's and highway access. A home for how you live today.

165 Hemlock Hills Rd S, Fairfield

$2,256,600

Welcome to 66 Gate Stone Lane, a quintessential Connecticut estate in the heart of historic Greenfield Hill. A gated entrance introduces this private 3.8-acre property, ideally positioned at the end of a quiet cul-de-sac among other distinguished homes. A gracious stone path leads to a double-height foyer, setting the tone for the home's refined architectural details and thoughtfully updated interiors. The formal living room features a fireplace, custom built-ins, and French doors opening to an outdoor dining area. A wood-paneled library with parquet floors offers serene views of the garden pond, while the elegant dining room flows seamlessly into a warm and inviting family room with fireplace and direct access to the patio. The home has been extensively and thoughtfully renovated throughout, including a completely redesigned chef's kitchen featuring custom cabinetry, high-end finishes, and the addition of a striking fireplace-creating a true heart-of-the-home gathering space. New hardwood floors run throughout, complemented by updated powder rooms and a state-of-the-art water filtration system. Upstairs, the expansive primary suite has been fully reimagined, offering a luxurious bedroom retreat with built-ins and window seat, along with a spa-caliber bath finished to the highest standard. Three additional guest bedrooms and a versatile additional room with Palladian windows-ideal for office or play-complete the second level.

4 Beds ⋅ 7 Baths ⋅ 24169966 MLS

Welcome to 66 Gate Stone Lane, a quintessential Connecticut estate in the heart of historic Greenfield Hill. A gated entrance introduces this private 3.8-acre property, ideally positioned at the end of a quiet cul-de-sac among other distinguished homes. A gracious stone path leads to a double-height foyer, setting the tone for the home's refined architectural details and thoughtfully updated interiors. The formal living room features a fireplace, custom built-ins, and French doors opening to an outdoor dining area. A wood-paneled library with parquet floors offers serene views of the garden pond, while the elegant dining room flows seamlessly into a warm and inviting family room with fireplace and direct access to the patio. The home has been extensively and thoughtfully renovated throughout, including a completely redesigned chef's kitchen featuring custom cabinetry, high-end finishes, and the addition of a striking fireplace-creating a true heart-of-the-home gathering space. New hardwood floors run throughout, complemented by updated powder rooms and a state-of-the-art water filtration system. Upstairs, the expansive primary suite has been fully reimagined, offering a luxurious bedroom retreat with built-ins and window seat, along with a spa-caliber bath finished to the highest standard. Three additional guest bedrooms and a versatile additional room with Palladian windows-ideal for office or play-complete the second level.

66 Gate Stone Ln, Fairfield

$2,220,000

SELLER REQUESTS HIGHEST & BEST OFFERS BY 4PM MONDAY 3/16. Set on two private, park-like acres in one of Fairfield's most sought after neighborhoods, this beautifully updated home offers over 4,000 square feet of thoughtfully designed living space with 5 bedrooms and 4.5 baths, including a dedicated home office for today's flexible lifestyle and gunite pool. The heart of the home is a chef's kitchen featuring custom inset cabinetry, an oversized center island with prep sink and Sub-Zero refrigerator drawers, a Wolf range, and generous space for cooking and gathering. Just beyond, a sun-filled dining room opens through patio doors to a bluestone terrace and pool, creating a seamless indoor-outdoor setting for entertaining. A dramatic two-story foyer is flanked by both a formal living room and a spacious family room with wood-burning fireplace, offering multiple spaces for everyday living. The main level also includes a fully equipped laundry room, a bright three-season sunroom, and a mudroom off the three-car garage. Conveniently located just off the mudroom is a full bath-perfect for rinsing off after an afternoon by the pool. Upstairs, the primary suite offers a true retreat with a brand-new spa-inspired bath and dual walk-in closets. This floor features four additional bedrooms. An unfinished walk-up third floor and massive lower level provides excellent potential for additional living space.

5 Beds ⋅ 5 Baths ⋅ 24158322 MLS

SELLER REQUESTS HIGHEST & BEST OFFERS BY 4PM MONDAY 3/16. Set on two private, park-like acres in one of Fairfield's most sought after neighborhoods, this beautifully updated home offers over 4,000 square feet of thoughtfully designed living space with 5 bedrooms and 4.5 baths, including a dedicated home office for today's flexible lifestyle and gunite pool. The heart of the home is a chef's kitchen featuring custom inset cabinetry, an oversized center island with prep sink and Sub-Zero refrigerator drawers, a Wolf range, and generous space for cooking and gathering. Just beyond, a sun-filled dining room opens through patio doors to a bluestone terrace and pool, creating a seamless indoor-outdoor setting for entertaining. A dramatic two-story foyer is flanked by both a formal living room and a spacious family room with wood-burning fireplace, offering multiple spaces for everyday living. The main level also includes a fully equipped laundry room, a bright three-season sunroom, and a mudroom off the three-car garage. Conveniently located just off the mudroom is a full bath-perfect for rinsing off after an afternoon by the pool. Upstairs, the primary suite offers a true retreat with a brand-new spa-inspired bath and dual walk-in closets. This floor features four additional bedrooms. An unfinished walk-up third floor and massive lower level provides excellent potential for additional living space.

677 Eleven O Clock Rd, Fairfield

$2,215,000

Comfort, style, and luxurious one-level living converge in this beautifully redesigned home, ideally located in lower Greenfield Hill. An enchanting architectural facade sets the tone for a residence defined by exceptional craftsmanship and refined finishes throughout. The open floor plan is anchored by a stunning family room with soaring cathedral ceiling, dramatic fireplace, and French doors that open to the patio--perfect for indoor/outdoor living. The chef's kitchen is stylish and functional, featuring custom cabinetry, a central island, and a sleek breakfast bar. An informal dining room or office, wrapped in windows on three sides and with heated tile floors, flows effortlessly into the formal dining room. A striking marble-topped bar adds a sophisticated touch, creating an ideal setting for entertaining. The primary suite offers a five-star retreat, highlighted by a recently renovated marble spa bath, with heated floor, custom cabinetry and closets. Additional bedrooms are generously proportioned. Enhancements include a well organized mudroom with built-in storage; skylights to add natural light; and a cozy, spacious lower level. Set on spectacular grounds with sweeping front and rear lawns, curated landscaping, and a stone patio with sitting wall and outdoor fireplace, this property offers an exceptional backdrop for relaxed living and sophisticated entertaining. Conveniently close to town amenities, 820 Hillside is an outstanding opportunity in a dream neighborhood.

3 Beds ⋅ 3 Baths ⋅ 24168800 MLS

Comfort, style, and luxurious one-level living converge in this beautifully redesigned home, ideally located in lower Greenfield Hill. An enchanting architectural facade sets the tone for a residence defined by exceptional craftsmanship and refined finishes throughout. The open floor plan is anchored by a stunning family room with soaring cathedral ceiling, dramatic fireplace, and French doors that open to the patio--perfect for indoor/outdoor living. The chef's kitchen is stylish and functional, featuring custom cabinetry, a central island, and a sleek breakfast bar. An informal dining room or office, wrapped in windows on three sides and with heated tile floors, flows effortlessly into the formal dining room. A striking marble-topped bar adds a sophisticated touch, creating an ideal setting for entertaining. The primary suite offers a five-star retreat, highlighted by a recently renovated marble spa bath, with heated floor, custom cabinetry and closets. Additional bedrooms are generously proportioned. Enhancements include a well organized mudroom with built-in storage; skylights to add natural light; and a cozy, spacious lower level. Set on spectacular grounds with sweeping front and rear lawns, curated landscaping, and a stone patio with sitting wall and outdoor fireplace, this property offers an exceptional backdrop for relaxed living and sophisticated entertaining. Conveniently close to town amenities, 820 Hillside is an outstanding opportunity in a dream neighborhood.

820 Hillside Rd, Fairfield

$2,200,000

Just a few blocks from the Greenfield Hill Green, an extraordinary opportunity awaits: a beloved estate, held by the same owners for more than 20 years, now reimagined for its next chapter. Taken virtually to the studs and thoughtfully rebuilt, much of the transformative work has already been done - creating the rare opportunity to step in at an exciting moment and complete a nearly 9,000-square-foot home entirely to your own vision. A new roof, siding, insulation, Marvin windows and doors, subflooring, extensive plumbing rough-ins and systems are among the significant improvements already in place, along with an exceptional newly built four-car garage. What remains is the rewarding part: the finishes, details and personal choices that will make it yours. Set on one of Greenfield Hill's picturesque properties, the home's generous, light-filled floor plan was designed for both everyday living and effortless entertaining. The main level flows between expansive living and family rooms, an eat-in kitchen, office, mudroom and potential first-floor en-suite bedroom. Upstairs, beautifully proportioned en-suite bedrooms offer privacy and flexibility, while the space above the four-car garage presents the potential for a private two-bedroom, two-bath guest or in-law suite with its own entrance.

6 Beds ⋅ 9 Baths ⋅ 24202996 MLS

Just a few blocks from the Greenfield Hill Green, an extraordinary opportunity awaits: a beloved estate, held by the same owners for more than 20 years, now reimagined for its next chapter. Taken virtually to the studs and thoughtfully rebuilt, much of the transformative work has already been done - creating the rare opportunity to step in at an exciting moment and complete a nearly 9,000-square-foot home entirely to your own vision. A new roof, siding, insulation, Marvin windows and doors, subflooring, extensive plumbing rough-ins and systems are among the significant improvements already in place, along with an exceptional newly built four-car garage. What remains is the rewarding part: the finishes, details and personal choices that will make it yours. Set on one of Greenfield Hill's picturesque properties, the home's generous, light-filled floor plan was designed for both everyday living and effortless entertaining. The main level flows between expansive living and family rooms, an eat-in kitchen, office, mudroom and potential first-floor en-suite bedroom. Upstairs, beautifully proportioned en-suite bedrooms offer privacy and flexibility, while the space above the four-car garage presents the potential for a private two-bedroom, two-bath guest or in-law suite with its own entrance.

201 Whites Hill Ln, Fairfield

$2,125,000

Classic charm on beautiful Bronson Road! A customized Colonial that overflows with extras - 4/5 bedrooms, open living spaces, play rooms, office/work zones, preserved historical touches and outdoor living options for all occasions! The main floor lives large. A formal living room, dining room, and sun room are on one side. While a huge front to back great room consisting of the kitchen, family room, play room, and the mudroom connection (complete with a built-in window seat) spans the other side. The breakfast bar has seating for 6, there is a dining area with full wet bar, a big stone fireplace with tons of room for gathering and lounging, plus access to the decks and patio beyond! Upstairs the primary suite is light and bright with vaulted ceilings, an oversized bath and a balcony. There are three generously sized bedrooms and a hall bath completing the second floor. On the lower level, walls of windows keep the rec room bright and sunny with tons of room to customize and the easy access to the outdoors is a bonus! At just under an acre, the property includes rolling lawns and plenty of privacy to enjoy all the space. There is a 2 car garage, and the central proximity to town, train schools and beaches is perfection!

4 Beds ⋅ 4 Baths ⋅ 24189160 MLS

Classic charm on beautiful Bronson Road! A customized Colonial that overflows with extras - 4/5 bedrooms, open living spaces, play rooms, office/work zones, preserved historical touches and outdoor living options for all occasions! The main floor lives large. A formal living room, dining room, and sun room are on one side. While a huge front to back great room consisting of the kitchen, family room, play room, and the mudroom connection (complete with a built-in window seat) spans the other side. The breakfast bar has seating for 6, there is a dining area with full wet bar, a big stone fireplace with tons of room for gathering and lounging, plus access to the decks and patio beyond! Upstairs the primary suite is light and bright with vaulted ceilings, an oversized bath and a balcony. There are three generously sized bedrooms and a hall bath completing the second floor. On the lower level, walls of windows keep the rec room bright and sunny with tons of room to customize and the easy access to the outdoors is a bonus! At just under an acre, the property includes rolling lawns and plenty of privacy to enjoy all the space. There is a 2 car garage, and the central proximity to town, train schools and beaches is perfection!

2444 Bronson Rd, Fairfield

$2,100,000

Nestled in the heart of historic Greenfield Hill, this special and timeless 1907 Queen Anne farmhouse provides an opportunity to own in one of the most desirable and coveted locations in Fairfield. The Clifford S. Banks house was once a farm where the owner raised turkeys, chickens, onions and bees. Situated on 2 acres of beautifully landscaped grounds that includes gardens and a barn- perfect for the equestrian family. This historic home has been thoughtfully expanded and restored over the last 40 years by the owners to maintain the old-world craftsmanship and provide modern comforts. As you approach the front entrance, you will be surrounded by an inviting screened porch and covered porches. A welcoming entry leads you to the inviting LR w/ expansive windows and wood burning fireplace, formal DR and FR w/ walls of built ins. The kitchen has been expanded to create a dining area w/ custom banquette seating and surrounded by windows providing an abundance of natural light. The kitchen was designed for a cook w/ attention to detail, design and function. The laundry room w/ ample storage and a Powder room complete the main level. The upper level has an inviting "sun parlor" which provides a cozy sitting area and office space. The primary bedroom features a comfortable retreat w/ walk-in closet and updated bath. There are 2 additional BRS and a hall bath. The spacious 3rd floor w/ architectural details and beams provide endless possibilities and storage. Full house generator.

3 Beds ⋅ 3 Baths ⋅ 24191574 MLS

Nestled in the heart of historic Greenfield Hill, this special and timeless 1907 Queen Anne farmhouse provides an opportunity to own in one of the most desirable and coveted locations in Fairfield. The Clifford S. Banks house was once a farm where the owner raised turkeys, chickens, onions and bees. Situated on 2 acres of beautifully landscaped grounds that includes gardens and a barn- perfect for the equestrian family. This historic home has been thoughtfully expanded and restored over the last 40 years by the owners to maintain the old-world craftsmanship and provide modern comforts. As you approach the front entrance, you will be surrounded by an inviting screened porch and covered porches. A welcoming entry leads you to the inviting LR w/ expansive windows and wood burning fireplace, formal DR and FR w/ walls of built ins. The kitchen has been expanded to create a dining area w/ custom banquette seating and surrounded by windows providing an abundance of natural light. The kitchen was designed for a cook w/ attention to detail, design and function. The laundry room w/ ample storage and a Powder room complete the main level. The upper level has an inviting "sun parlor" which provides a cozy sitting area and office space. The primary bedroom features a comfortable retreat w/ walk-in closet and updated bath. There are 2 additional BRS and a hall bath. The spacious 3rd floor w/ architectural details and beams provide endless possibilities and storage. Full house generator.

2477 Bronson Rd, Fairfield

$2,050,000

1680 Cross Highway is a nod to all of the pristine, old-school colonials in leafy Greenfield Hill, however, its interiors and landscape have been beautifully updated to reflect the needs of the current owners, a modern family of four, with a nanny and friends continuously coming and going. The chef's kitchen was masterfully streamlined with new GE Monogram appliances, an oversized center island, and incredible storage capability. The flow continues into an open dining room on one side, a spacious family room on the other, with a wood burning fireplace and easy access to a screened-in porch, Trex deck and hot tub. A formal living room with a fireplace often kicks off the evening, inviting outdoor relaxation on the side deck, with views of the private yard and vegetable gardens. A corner library with custom bookcases, mudroom, laundry, and half bath complete the first floor. Upstairs, the primary suite was updated to provide a spa-like, oversized bathroom and additional walk-in closet space. There are three additional well-proportioned bedrooms and bathrooms. The basement has been reworked too, mostly to accommodate visitors and add a finished 1215 sq ft of living space: rec-room with built-ins, kitchenette/breakfast bar, a bedroom, full bath and gym space. Convenience is king here too with a convenient location for commuting, shopping, school drop-off, and sporting events. The outdoor spaces are sublime, and capture the relaxed and connected spirit of the current owners.

5 Beds ⋅ 6 Baths ⋅ 24188539 MLS

1680 Cross Highway is a nod to all of the pristine, old-school colonials in leafy Greenfield Hill, however, its interiors and landscape have been beautifully updated to reflect the needs of the current owners, a modern family of four, with a nanny and friends continuously coming and going. The chef's kitchen was masterfully streamlined with new GE Monogram appliances, an oversized center island, and incredible storage capability. The flow continues into an open dining room on one side, a spacious family room on the other, with a wood burning fireplace and easy access to a screened-in porch, Trex deck and hot tub. A formal living room with a fireplace often kicks off the evening, inviting outdoor relaxation on the side deck, with views of the private yard and vegetable gardens. A corner library with custom bookcases, mudroom, laundry, and half bath complete the first floor. Upstairs, the primary suite was updated to provide a spa-like, oversized bathroom and additional walk-in closet space. There are three additional well-proportioned bedrooms and bathrooms. The basement has been reworked too, mostly to accommodate visitors and add a finished 1215 sq ft of living space: rec-room with built-ins, kitchenette/breakfast bar, a bedroom, full bath and gym space. Convenience is king here too with a convenient location for commuting, shopping, school drop-off, and sporting events. The outdoor spaces are sublime, and capture the relaxed and connected spirit of the current owners.

1680 Cross Hwy, Fairfield

$2,025,000

This is not just a house-it's a home with soul. Lovingly cared for and impeccably maintained by the same family for nearly 30 years, this 4-bedroom, 3.5-bath Colonial unfolds in ways you don't expect, each space more surprising than the last. The kitchen is extraordinary-a centerpiece that captivates and performs. Anchored by a single-slab Carrera marble island and a premium Thermador suite, it balances beauty and function. Custom cabinetry and stone countertops line the perimeter, while dramatic gazebo-style architecture and cathedral ceilings fill the room with light. A bay window with a built-in seat frames tranquil backyard views, creating a seamless indoor-outdoor connection where life naturally gathers. The family room is equally striking. Vaulted ceilings create airiness, while a gas fireplace with a floor-to-ceiling whitewashed brick chimney anchors the space. Custom built-ins flank the hearth, blending elegance and purpose in a room that feels refined yet inviting. Upstairs, four bedrooms include a serene primary suite, updated baths, and ample closet space. The newly finished lower level expands the home's possibilities-perfect for a media room, gym, playroom, office, or guest retreat. A custom-built playhouse and stunning accent wall add whimsy and sophistication, making this space a seamless extension of the home rather than an afterthought. A home that reveals itself in layers-unexpected, memorable, and truly special.

4 Beds ⋅ 3 Baths ⋅ 24163341 MLS

This is not just a house-it's a home with soul. Lovingly cared for and impeccably maintained by the same family for nearly 30 years, this 4-bedroom, 3.5-bath Colonial unfolds in ways you don't expect, each space more surprising than the last. The kitchen is extraordinary-a centerpiece that captivates and performs. Anchored by a single-slab Carrera marble island and a premium Thermador suite, it balances beauty and function. Custom cabinetry and stone countertops line the perimeter, while dramatic gazebo-style architecture and cathedral ceilings fill the room with light. A bay window with a built-in seat frames tranquil backyard views, creating a seamless indoor-outdoor connection where life naturally gathers. The family room is equally striking. Vaulted ceilings create airiness, while a gas fireplace with a floor-to-ceiling whitewashed brick chimney anchors the space. Custom built-ins flank the hearth, blending elegance and purpose in a room that feels refined yet inviting. Upstairs, four bedrooms include a serene primary suite, updated baths, and ample closet space. The newly finished lower level expands the home's possibilities-perfect for a media room, gym, playroom, office, or guest retreat. A custom-built playhouse and stunning accent wall add whimsy and sophistication, making this space a seamless extension of the home rather than an afterthought. A home that reveals itself in layers-unexpected, memorable, and truly special.

757 Galloping Hill Rd, Fairfield

$2,000,000

3808 Redding Road presents a rare opportunity to step into one of Fairfield's most distinctive properties; where early American history and modern living come together. Originally dating to 1769 and fully rebuilt in 2008, the home was reimagined to preserve its architectural integrity while delivering an ease making it livable for today. Inside the tone is warm, grounded, and refined. Original beams and centuries-old floors remain at the core, while refreshed interiors and natural light bring a sense of clarity and renewal throughout. A rare three-fireplace hearth anchors the main living spaces, creating a natural center point for gathering. Four bedrooms and four and a half baths offer both comfort and flexibility, including a primary suite with a private balcony overlooking the property as it comes alive in the spring. The land is expansive, yet entirely manageable. Nearly eighteen acres unfold into open fields, budding orchards, and wooded edges - offering the option to embrace the full scale of the property or maintain a more modest footprint. Whether for gardening, recreation, or quiet enjoyment, the setting adapts easily. A historic barn, carriage house, and chicken coop add character and versatility. Privately set yet just minutes from town, this is a property that delivers both space and convenience. 3808 Redding Road offers a sense of history, a renewed perspective, and the flexibility to live as you choose.

4 Beds ⋅ 5 Baths ⋅ 24171406 MLS

3808 Redding Road presents a rare opportunity to step into one of Fairfield's most distinctive properties; where early American history and modern living come together. Originally dating to 1769 and fully rebuilt in 2008, the home was reimagined to preserve its architectural integrity while delivering an ease making it livable for today. Inside the tone is warm, grounded, and refined. Original beams and centuries-old floors remain at the core, while refreshed interiors and natural light bring a sense of clarity and renewal throughout. A rare three-fireplace hearth anchors the main living spaces, creating a natural center point for gathering. Four bedrooms and four and a half baths offer both comfort and flexibility, including a primary suite with a private balcony overlooking the property as it comes alive in the spring. The land is expansive, yet entirely manageable. Nearly eighteen acres unfold into open fields, budding orchards, and wooded edges - offering the option to embrace the full scale of the property or maintain a more modest footprint. Whether for gardening, recreation, or quiet enjoyment, the setting adapts easily. A historic barn, carriage house, and chicken coop add character and versatility. Privately set yet just minutes from town, this is a property that delivers both space and convenience. 3808 Redding Road offers a sense of history, a renewed perspective, and the flexibility to live as you choose.

3808 Redding Rd, Fairfield

$1,950,000

Curb appeal abounds in this picture-perfect Colonial, newly clad in white cedar and set in a coveted neighborhood of upscale homes and walkable, picturesque streets. Ideally located in the western portion of Greenfield Hill, just minutes from the village center, seasonal farmers market, shopping, dining, train, and major roads. Inside, hardwood floors, central air, many rooms freshly painted and two wood-burning fireplaces create a comfortable and inviting atmosphere. The first floor offers both formal and casual living spaces, plus a spacious screened-in porch for relaxing with three-season enjoyment (not in the SQ FT of home). The well-appointed kitchen flows seamlessly into a bright family room with vaulted ceilings and a casual dining area. A mudroom off the garage provides a practical everyday entry. Upstairs, the primary suite features an updated full bath and a generous walk-in closet. Three additional bedrooms share a hall bath, with access to a walk-up attic for extra storage. A full basement and charming red shed add even more storage options. The backyard is a private oasis, complete with a heated in-ground gunite pool and professionally designed landscaping. With nearby home sales averaging over $1.97M in the past year, this property represents exceptional value. Don't miss this opportunity! See agent remarks. Highest/Best by Monday May 18 at 3PM

4 Beds ⋅ 3 Baths ⋅ 24173223 MLS

Curb appeal abounds in this picture-perfect Colonial, newly clad in white cedar and set in a coveted neighborhood of upscale homes and walkable, picturesque streets. Ideally located in the western portion of Greenfield Hill, just minutes from the village center, seasonal farmers market, shopping, dining, train, and major roads. Inside, hardwood floors, central air, many rooms freshly painted and two wood-burning fireplaces create a comfortable and inviting atmosphere. The first floor offers both formal and casual living spaces, plus a spacious screened-in porch for relaxing with three-season enjoyment (not in the SQ FT of home). The well-appointed kitchen flows seamlessly into a bright family room with vaulted ceilings and a casual dining area. A mudroom off the garage provides a practical everyday entry. Upstairs, the primary suite features an updated full bath and a generous walk-in closet. Three additional bedrooms share a hall bath, with access to a walk-up attic for extra storage. A full basement and charming red shed add even more storage options. The backyard is a private oasis, complete with a heated in-ground gunite pool and professionally designed landscaping. With nearby home sales averaging over $1.97M in the past year, this property represents exceptional value. Don't miss this opportunity! See agent remarks. Highest/Best by Monday May 18 at 3PM

324 Jennie Ln, Fairfield

$1,850,000

Some homes simply give you a place to live. Others quietly become part of the way you live. Tucked away at the end of a private cul-de-sac in Fairfield's coveted Greenfield Hill, 3233 North Street is one of those rare homes where privacy, nature, and everyday living come together effortlessly. Set on more than three acres and bordering the 186-acre Brett Woods trail system, this is a setting that invites morning walks, peaceful afternoons, and the simple luxury of having nature just moments away-all while remaining minutes from Fairfield's vibrant town center, beaches, train, shopping, dining, and top-rated schools. Inside, soaring ceilings and oversized windows flood the home with natural light, creating bright, welcoming spaces that feel connected and alive throughout the day. The kitchen flows seamlessly into the family room, while multiple living areas offer the flexibility to gather, entertain, celebrate, or simply enjoy a quiet evening at home. These are the kinds of spaces where conversations linger, traditions take root, and the people you love naturally find their way back. A completely separate wing with its own private entrance and garage, full eat-in kitchen, ensuite bedroom, and sun-filled living room provides exceptional flexibility for extended family, long-term guests, an au pair, or independent living. It isn't about having more space. It's about having a home that's ready for whatever life brings next.

5 Beds ⋅ 5 Baths ⋅ 24189785 MLS

Some homes simply give you a place to live. Others quietly become part of the way you live. Tucked away at the end of a private cul-de-sac in Fairfield's coveted Greenfield Hill, 3233 North Street is one of those rare homes where privacy, nature, and everyday living come together effortlessly. Set on more than three acres and bordering the 186-acre Brett Woods trail system, this is a setting that invites morning walks, peaceful afternoons, and the simple luxury of having nature just moments away-all while remaining minutes from Fairfield's vibrant town center, beaches, train, shopping, dining, and top-rated schools. Inside, soaring ceilings and oversized windows flood the home with natural light, creating bright, welcoming spaces that feel connected and alive throughout the day. The kitchen flows seamlessly into the family room, while multiple living areas offer the flexibility to gather, entertain, celebrate, or simply enjoy a quiet evening at home. These are the kinds of spaces where conversations linger, traditions take root, and the people you love naturally find their way back. A completely separate wing with its own private entrance and garage, full eat-in kitchen, ensuite bedroom, and sun-filled living room provides exceptional flexibility for extended family, long-term guests, an au pair, or independent living. It isn't about having more space. It's about having a home that's ready for whatever life brings next.

3233 North St, Fairfield

$1,825,000

This timeless colonial sits beautifully behind a long sweep of native New England stone wall that Greenfield Hill is known for. Fully renovated and expanded in 2010, every decision was made with intention: preserve the home's classic character while creating the open, connected spaces today's lifestyle demands. Rooms that flow and breathe, quality millwork and molding details, and hardware and finishes that whisper elegance without shouting for attention. The current aesthetic is a classic, curated look with Nancy Meyers vibes - but the interiors are flexible enough to make it entirely your own. Step outside and you'll understand why this property is special. Thoughtfully designed with multiple vignette-like areas, each with its own character and purpose - a dining terrace built for long summer evenings, a shaded fire pit terrace for every season, and perennial gardens that lead to a sun-drenched bluestone terrace edged in roses. Manicured lawns and groomed pea gravel paths connect it all - with a flawless pool site if that's on your wishlist. The location is the kind you can't manufacture: a quiet, tree-lined oasis with genuine privacy, yet just minutes from the best of Fairfield and Westport - restaurants, commuter trains, hiking trails, golf, and equestrian clubs. Private, but never isolated. Peaceful, but never far from everything. This home's story is filled with joyful summer gatherings, holiday parties, and cozy quiet moments. The next chapter is yours to write.

5 Beds ⋅ 4 Baths ⋅ 24177222 MLS

This timeless colonial sits beautifully behind a long sweep of native New England stone wall that Greenfield Hill is known for. Fully renovated and expanded in 2010, every decision was made with intention: preserve the home's classic character while creating the open, connected spaces today's lifestyle demands. Rooms that flow and breathe, quality millwork and molding details, and hardware and finishes that whisper elegance without shouting for attention. The current aesthetic is a classic, curated look with Nancy Meyers vibes - but the interiors are flexible enough to make it entirely your own. Step outside and you'll understand why this property is special. Thoughtfully designed with multiple vignette-like areas, each with its own character and purpose - a dining terrace built for long summer evenings, a shaded fire pit terrace for every season, and perennial gardens that lead to a sun-drenched bluestone terrace edged in roses. Manicured lawns and groomed pea gravel paths connect it all - with a flawless pool site if that's on your wishlist. The location is the kind you can't manufacture: a quiet, tree-lined oasis with genuine privacy, yet just minutes from the best of Fairfield and Westport - restaurants, commuter trains, hiking trails, golf, and equestrian clubs. Private, but never isolated. Peaceful, but never far from everything. This home's story is filled with joyful summer gatherings, holiday parties, and cozy quiet moments. The next chapter is yours to write.

1960 North St, Fairfield

$1,820,000

Welcome to 621 Shrub Oak Lane, a classic Colonial set on two private acres in Greenfield Hill. Tucked away on a quiet cul-de-sac in a highly desirable neighborhood, this five-bedroom home blends timeless charm with modern comfort for today's lifestyle. The main level features formal living and dining rooms, perfect for gathering and entertaining, along with an updated kitchen with granite countertops, Wolf and Sub-Zero appliances. The inviting family room, anchored by a stunning stone fireplace, opens to an expansive deck-creating seamless indoor-outdoor living. A main-level bedroom can also serve as a private home office, offering a flexible living space. Upstairs, the oversized primary suite includes a sitting area, updated bath with marble countertops, makeup vanity, and walk-in closet. Three additional bedrooms and a renovated bath complete the second level. An unfinished basement offers a blank canvas to create additional living space, a home gym, or media room. The outdoor setting is designed for both relaxation and recreation, featuring a large, flat fenced yard with an in-ground pool and spacious deck with awning-ideal for entertaining or unwinding poolside. The property extends beyond the fenced yard to include additional wooded acreage, offering added privacy and a serene natural setting. Conveniently located near shopping, schools, and the Merritt Parkway, this exceptional property captures the best of Connecticut living.

5 Beds ⋅ 3 Baths ⋅ 24168500 MLS

Welcome to 621 Shrub Oak Lane, a classic Colonial set on two private acres in Greenfield Hill. Tucked away on a quiet cul-de-sac in a highly desirable neighborhood, this five-bedroom home blends timeless charm with modern comfort for today's lifestyle. The main level features formal living and dining rooms, perfect for gathering and entertaining, along with an updated kitchen with granite countertops, Wolf and Sub-Zero appliances. The inviting family room, anchored by a stunning stone fireplace, opens to an expansive deck-creating seamless indoor-outdoor living. A main-level bedroom can also serve as a private home office, offering a flexible living space. Upstairs, the oversized primary suite includes a sitting area, updated bath with marble countertops, makeup vanity, and walk-in closet. Three additional bedrooms and a renovated bath complete the second level. An unfinished basement offers a blank canvas to create additional living space, a home gym, or media room. The outdoor setting is designed for both relaxation and recreation, featuring a large, flat fenced yard with an in-ground pool and spacious deck with awning-ideal for entertaining or unwinding poolside. The property extends beyond the fenced yard to include additional wooded acreage, offering added privacy and a serene natural setting. Conveniently located near shopping, schools, and the Merritt Parkway, this exceptional property captures the best of Connecticut living.

621 Shrub Oak Ln, Fairfield

$1,753,000

Greenfield Hill Court - A Legacy Reimagined Nestled amid the tranquil woodlands of Fairfield's coveted Greenfield Hill, this timeless residence blends historic charm with contemporary luxury. The home's lineage of love and craftsmanship endures through every detail - now beautifully renewed for the next generation. A brandnew chef's kitchen anchors the heart of the home, complemented by updated bathrooms that marry classic design with modern comfort. Outdoors, the property unfolds into a private retreat: an expansive Pickleball court, basketball area, and lush, manicured gardens that invite play and peace in equal measure. Evenings gather around the stone fire pit, where laughter and stories rise beneath the stars. The twocar garage offers not only secure parking but also a bonus storage area for lawn and garden tools - a thoughtful touch for those who cherish both beauty and practicality. Free from historical restrictions yet rich in heritage, Greenfield Hill Court stands as a rare opportunity: a home with a past worth preserving and a future ready to be lived.

4 Beds ⋅ 3 Baths ⋅ 24165368 MLS

Greenfield Hill Court - A Legacy Reimagined Nestled amid the tranquil woodlands of Fairfield's coveted Greenfield Hill, this timeless residence blends historic charm with contemporary luxury. The home's lineage of love and craftsmanship endures through every detail - now beautifully renewed for the next generation. A brandnew chef's kitchen anchors the heart of the home, complemented by updated bathrooms that marry classic design with modern comfort. Outdoors, the property unfolds into a private retreat: an expansive Pickleball court, basketball area, and lush, manicured gardens that invite play and peace in equal measure. Evenings gather around the stone fire pit, where laughter and stories rise beneath the stars. The twocar garage offers not only secure parking but also a bonus storage area for lawn and garden tools - a thoughtful touch for those who cherish both beauty and practicality. Free from historical restrictions yet rich in heritage, Greenfield Hill Court stands as a rare opportunity: a home with a past worth preserving and a future ready to be lived.

3810 Congress St, Fairfield

$1,710,000

HIGHEST & BEST OFFERS DUE BY MONDAY JULY 27 4PM. Nestled on a peaceful cul-de-sac in the heart of Greenfield Hill, this fantastic 4-bedroom Colonial offers the perfect blend of charm, space, & a picturesque setting. Filled with natural light throughout, this bright & welcoming home exudes warmth and offers an inviting atmosphere for everyday living. A welcoming foyer leads to spacious formal living and dining rooms, ideal for both entertaining & family gatherings. The eat-in kitchen overlooks the stunning, fenced in backyard, where beautifully landscaped level grounds, surrounded by mature specimen trees, extend to views of the Sasco Brook in the distance, creating a serene & private backdrop. The kitchen flows seamlessly into the oversized family room with a fireplace & an inviting sunroom, both offering easy access to the expansive mahogany deck & outdoor living spaces. Upstairs, you'll find a spacious primary suite along with 3 generously sized bedrooms, a dedicated home office, and the convenience of second-floor laundry. One of the bedrooms offers access to a walk-up attic, presenting an exciting opportunity to finish the space &create a bonus room, studio or private retreat. The unfinished lower level provides yet another opportunity to expand, offering ample space for a recreation room, home gym, or media room. Set in one of Fairfield's most desirable neighborhoods, this home combines timeless appeal, an exceptional floor plan, and the idyllic Greenfield Hill lifestyle

4 Beds ⋅ 3 Baths ⋅ 24190794 MLS

HIGHEST & BEST OFFERS DUE BY MONDAY JULY 27 4PM. Nestled on a peaceful cul-de-sac in the heart of Greenfield Hill, this fantastic 4-bedroom Colonial offers the perfect blend of charm, space, & a picturesque setting. Filled with natural light throughout, this bright & welcoming home exudes warmth and offers an inviting atmosphere for everyday living. A welcoming foyer leads to spacious formal living and dining rooms, ideal for both entertaining & family gatherings. The eat-in kitchen overlooks the stunning, fenced in backyard, where beautifully landscaped level grounds, surrounded by mature specimen trees, extend to views of the Sasco Brook in the distance, creating a serene & private backdrop. The kitchen flows seamlessly into the oversized family room with a fireplace & an inviting sunroom, both offering easy access to the expansive mahogany deck & outdoor living spaces. Upstairs, you'll find a spacious primary suite along with 3 generously sized bedrooms, a dedicated home office, and the convenience of second-floor laundry. One of the bedrooms offers access to a walk-up attic, presenting an exciting opportunity to finish the space &create a bonus room, studio or private retreat. The unfinished lower level provides yet another opportunity to expand, offering ample space for a recreation room, home gym, or media room. Set in one of Fairfield's most desirable neighborhoods, this home combines timeless appeal, an exceptional floor plan, and the idyllic Greenfield Hill lifestyle

142 Horseshoe Ln, Fairfield

$1,640,000

Set on over two private acres in the gated community of The Ridge, this stunning estate combines modern comfort with timeless design. Residents enjoy resort-style amenities including a clubhouse, pool, tennis courts, playground, basketball court, private recreation facilities, and 24/7 gate security. Step inside through a soaring vaulted foyer that opens to a sun-filled living room framed by a dramatic wall of windows. Designed for entertainment, the formal dining room features tray ceilings and bay windows that create a bright, open atmosphere. At the center of the home, the chef's kitchen boasts a professional-grade Viking range, double ovens, a central island, and a casual dining area. French doors connect the kitchen to a sunny enclosed patio and a bluestone terrace overlooking the serene grounds-ideal for indoor-outdoor living. The family room impresses with a two-story stone fireplace and expansive windows, while a spiral staircase leads to a loft retreat-perfect for a private office or reading nook. The primary suite offers a true sanctuary with a gas fireplace, walk-in closets, and a luxurious spa bath complete with dual vanities, a jetted soaking tub, and a large shower. French doors open to the patio, blending relaxation with nature. This home is a rare opportunity to own a refined retreat in one of the area's most prestigious communities.

6 Beds ⋅ 5 Baths ⋅ 24124091 MLS

Set on over two private acres in the gated community of The Ridge, this stunning estate combines modern comfort with timeless design. Residents enjoy resort-style amenities including a clubhouse, pool, tennis courts, playground, basketball court, private recreation facilities, and 24/7 gate security. Step inside through a soaring vaulted foyer that opens to a sun-filled living room framed by a dramatic wall of windows. Designed for entertainment, the formal dining room features tray ceilings and bay windows that create a bright, open atmosphere. At the center of the home, the chef's kitchen boasts a professional-grade Viking range, double ovens, a central island, and a casual dining area. French doors connect the kitchen to a sunny enclosed patio and a bluestone terrace overlooking the serene grounds-ideal for indoor-outdoor living. The family room impresses with a two-story stone fireplace and expansive windows, while a spiral staircase leads to a loft retreat-perfect for a private office or reading nook. The primary suite offers a true sanctuary with a gas fireplace, walk-in closets, and a luxurious spa bath complete with dual vanities, a jetted soaking tub, and a large shower. French doors open to the patio, blending relaxation with nature. This home is a rare opportunity to own a refined retreat in one of the area's most prestigious communities.

212 Fence Row Dr, Fairfield

$1,600,000

BEST AND FINAL OFFERS DUE MONDAY 6/8/26 BY 8PM Location, Floorplan, Gorgeous yard! Located in one of the most sought after Greenfield Hill cul de sacs. Over-sized windows and high ceilings flood the kitchen, dining area and great room with natural light. Easy entertaining as one room evolves into the next: kitchen opens to Great Room w/ 2-story fireplace to Family Room to Formal Living Room w/ 2nd fireplace. the Kitchen also opens to the Formal Dining Room. Tons of natural light from Floor to ceiling windows, French doors and walls of windows, all showing off the stunning rear yard with plenty of room for a pool and play. A rear hall adds one of two powder rooms, laundry room, mudroom area and access to the 3-car garage. The primary suite + 3 BRS on the 2nd floor. The primary includes sitting area, two walk in closets and spacious luxe bath. The three additional bedrooms are generously sized with double closets and access to full hall bath. A full finished lower level adds a dedicated fitness room, media area and rec area with stairs to main level and 2nd set of stairs to the garage (excellent au pair or inlaw potential). Don't miss plenty of storage in the attic and basement. Enjoy the privacy of a cul de sac, a huge patio looking over mature trees, tons of planting beds and a level football-size rear yard. Minutes from Greenfield center, farmers market, schools, shopping, beaches and all that Fairfield has to offer.

4 Beds ⋅ 4 Baths ⋅ 24179618 MLS

BEST AND FINAL OFFERS DUE MONDAY 6/8/26 BY 8PM Location, Floorplan, Gorgeous yard! Located in one of the most sought after Greenfield Hill cul de sacs. Over-sized windows and high ceilings flood the kitchen, dining area and great room with natural light. Easy entertaining as one room evolves into the next: kitchen opens to Great Room w/ 2-story fireplace to Family Room to Formal Living Room w/ 2nd fireplace. the Kitchen also opens to the Formal Dining Room. Tons of natural light from Floor to ceiling windows, French doors and walls of windows, all showing off the stunning rear yard with plenty of room for a pool and play. A rear hall adds one of two powder rooms, laundry room, mudroom area and access to the 3-car garage. The primary suite + 3 BRS on the 2nd floor. The primary includes sitting area, two walk in closets and spacious luxe bath. The three additional bedrooms are generously sized with double closets and access to full hall bath. A full finished lower level adds a dedicated fitness room, media area and rec area with stairs to main level and 2nd set of stairs to the garage (excellent au pair or inlaw potential). Don't miss plenty of storage in the attic and basement. Enjoy the privacy of a cul de sac, a huge patio looking over mature trees, tons of planting beds and a level football-size rear yard. Minutes from Greenfield center, farmers market, schools, shopping, beaches and all that Fairfield has to offer.

90 Calf Pond Ln, Fairfield

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