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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

$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

$1,310,000

Rolling Hills Drive is the kind of street where homes feel settled into their surroundings, quiet and residential, with attractive homes lining the neighborhood and nature close at hand. Just moments from hiking trails, Lake Mohegan, and Smith Richardson Golf Course, it's a setting that offers both neighborhood connection and easy access to the outdoors. At 126, a classic Colonial sits gracefully on two private acres. The property evolves beautifully through the seasons: green lawns in summer, vibrant foliage in fall, and peaceful snow-covered grounds in winter, each bringing its own character to the setting. Inside, the home carries the same warmth and ease, with cozy, welcoming living spaces anchored by a bright, updated kitchen that naturally becomes the heart of the home. Four full baths add a level of comfort and convenience that makes daily life and hosting feel effortless. Outside, a bluestone front porch with river rock accents offers an inviting place to begin the day, while the backyard opens to broad lawn and a firepit gathering area tucked into the landscape. It's the kind of property where afternoons stretch into evenings, and where outdoor living becomes part of daily life. Inside and out, the home reflects the enduring appeal of a traditional Colonial: balanced, welcoming, and easy to live in. A property defined by space, natural surroundings, and the neighborhood character that makes Rolling Hills Drive one of Fairfield's most peaceful residential settings.

4 Beds ⋅ 4 Baths ⋅ 24158186 MLS

Rolling Hills Drive is the kind of street where homes feel settled into their surroundings, quiet and residential, with attractive homes lining the neighborhood and nature close at hand. Just moments from hiking trails, Lake Mohegan, and Smith Richardson Golf Course, it's a setting that offers both neighborhood connection and easy access to the outdoors. At 126, a classic Colonial sits gracefully on two private acres. The property evolves beautifully through the seasons: green lawns in summer, vibrant foliage in fall, and peaceful snow-covered grounds in winter, each bringing its own character to the setting. Inside, the home carries the same warmth and ease, with cozy, welcoming living spaces anchored by a bright, updated kitchen that naturally becomes the heart of the home. Four full baths add a level of comfort and convenience that makes daily life and hosting feel effortless. Outside, a bluestone front porch with river rock accents offers an inviting place to begin the day, while the backyard opens to broad lawn and a firepit gathering area tucked into the landscape. It's the kind of property where afternoons stretch into evenings, and where outdoor living becomes part of daily life. Inside and out, the home reflects the enduring appeal of a traditional Colonial: balanced, welcoming, and easy to live in. A property defined by space, natural surroundings, and the neighborhood character that makes Rolling Hills Drive one of Fairfield's most peaceful residential settings.

126 Rolling Hills Dr, Fairfield

$1,400,000

Rare opportunity in Fairfield's coveted Greenfield Hill! This 2013 custom-built, meticulously maintained home offers the perfect balance of luxury, privacy, and low-maintenance living. Situated on a manageable .28-acres, you'll enjoy the serenity of a country retreat without the upkeep of a large estate. Set along one of Fairfield's designated scenic roads, and with Brett Woods Open Space as its backdrop, 1192 Catamount is surrounded by natural beauty while remaining incredibly connected to both Fairfield & Westport. Outside, this home welcomes you with a wraparound front porch. Inside, the open floor plan showcases 9'+ ceilings and exceptional custom millwork. The main level features a family room anchored by a floor-to-ceiling stone gas fireplace, a paneled office behind french doors, a gourmet kitchen with Viking appliances and a marble center island ideal for entertaining. The dining area is framed by floor-to-ceiling windows that capture the surrounding woodland landscape. Upstairs, the primary suite offers a tray ceiling, walk-in closet, and spa-inspired marble bath.Two additional bedrooms share a hall bath, conveniently located near a dedicated laundry area.The lower level offers versatility as a guest suite with its own full bath. A full standing height attic with natural light provides future expansion potential.Recent upgrades include exterior/interior paint, a new driveway, patio, and a whole-house generator which offer true move-in confidence from day one

3 Beds ⋅ 4 Baths ⋅ 24181750 MLS

Rare opportunity in Fairfield's coveted Greenfield Hill! This 2013 custom-built, meticulously maintained home offers the perfect balance of luxury, privacy, and low-maintenance living. Situated on a manageable .28-acres, you'll enjoy the serenity of a country retreat without the upkeep of a large estate. Set along one of Fairfield's designated scenic roads, and with Brett Woods Open Space as its backdrop, 1192 Catamount is surrounded by natural beauty while remaining incredibly connected to both Fairfield & Westport. Outside, this home welcomes you with a wraparound front porch. Inside, the open floor plan showcases 9'+ ceilings and exceptional custom millwork. The main level features a family room anchored by a floor-to-ceiling stone gas fireplace, a paneled office behind french doors, a gourmet kitchen with Viking appliances and a marble center island ideal for entertaining. The dining area is framed by floor-to-ceiling windows that capture the surrounding woodland landscape. Upstairs, the primary suite offers a tray ceiling, walk-in closet, and spa-inspired marble bath.Two additional bedrooms share a hall bath, conveniently located near a dedicated laundry area.The lower level offers versatility as a guest suite with its own full bath. A full standing height attic with natural light provides future expansion potential.Recent upgrades include exterior/interior paint, a new driveway, patio, and a whole-house generator which offer true move-in confidence from day one

1192 Catamount Rd, Fairfield

$1,250,000

BASED ON STRONG INTEREST, PLEASE SUBMIT ALL OFFERS, HIGHEST & BEST, BY 5PM MONDAY MAY 18. Sitting pretty behind a charming fieldstone wall, in a sought after neighborhood, this long loved Garrison Colonial feels fresh and inviting! Recent updates include a brand new high efficiency boiler and hot water heater, new roof, new gravel driveway with Belgian Block, new Pella windows, new Bathrooms detailed with Turkish tile, interior paint in soft hues of grey, and gleaming hardwood floors throughout. The classic center hall leads to a sunny Living Room, and alternately to the Family Room, anchored by a cozy fireplace with raised hearth. The Eat in Kitchen opens to the Dining Room. The Den/Office, Laundry and Powder Room complete the main level. Upstairs, four generously scaled Bedrooms include a Primary en suite Bedroom and three other Bedrooms which share a hall Bathroom. Walk up Attic offers additional storage. Outside, the expansive deck and bluestone patio overlook an exceptionally private and flat 1.1 acre of lush lawn, specimen trees, and a distant shed that looks like a small vintage barn. Sited at the highest point of Galloping Hill, this rare panoramic vista elicits a feeling of pure serenity. Convenient to Fairfield's town center, with restaurants, shopping, library, train and beaches, this special slice of Greenfield Hill is a wonderful place to call home!

4 Beds ⋅ 3 Baths ⋅ 24173423 MLS

BASED ON STRONG INTEREST, PLEASE SUBMIT ALL OFFERS, HIGHEST & BEST, BY 5PM MONDAY MAY 18. Sitting pretty behind a charming fieldstone wall, in a sought after neighborhood, this long loved Garrison Colonial feels fresh and inviting! Recent updates include a brand new high efficiency boiler and hot water heater, new roof, new gravel driveway with Belgian Block, new Pella windows, new Bathrooms detailed with Turkish tile, interior paint in soft hues of grey, and gleaming hardwood floors throughout. The classic center hall leads to a sunny Living Room, and alternately to the Family Room, anchored by a cozy fireplace with raised hearth. The Eat in Kitchen opens to the Dining Room. The Den/Office, Laundry and Powder Room complete the main level. Upstairs, four generously scaled Bedrooms include a Primary en suite Bedroom and three other Bedrooms which share a hall Bathroom. Walk up Attic offers additional storage. Outside, the expansive deck and bluestone patio overlook an exceptionally private and flat 1.1 acre of lush lawn, specimen trees, and a distant shed that looks like a small vintage barn. Sited at the highest point of Galloping Hill, this rare panoramic vista elicits a feeling of pure serenity. Convenient to Fairfield's town center, with restaurants, shopping, library, train and beaches, this special slice of Greenfield Hill is a wonderful place to call home!

1090 Galloping 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

$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

$1,180,000

Rare lower Greenfield Hill opportunity at an accessible price point. Set on 2 private acres, 209 Merwins Lane offers charm, privacy and everyday livability in one of Fairfield's most sought after locations. Enjoy easy access to Greenfield Center, a quick drive to Westport and a convenient direct route to Fairfield Train Station, just 3.5 miles away. This classic center hall Cape is warm, inviting and easy to love. The main level features a living room with fireplace, traditional dining room, functional kitchen, an oversized rear family room that creates wonderful additional living space and a full bath. In addition, there is a flexible first floor room, currently used as additional living space and a home office, adds convenience for today's lifestyle while offering options for guests, work from home or future needs. Upstairs, two generously sized bedrooms share a full bath off the center hall. One bedroom was previously two bedroom rooms, offering added flexibility within the existing footprint if desired to convert back to three bedrooms. Perfect for downsizers, first time Greenfield Hill buyers or anyone seeking privacy, land and location, this home offers immediate appeal with meaningful long term potential. Move right in, enjoy the charm and explore future possibilities at your own pace in a beloved Fairfield neighborhood.

3 Beds ⋅ 2 Baths ⋅ 24154961 MLS

Rare lower Greenfield Hill opportunity at an accessible price point. Set on 2 private acres, 209 Merwins Lane offers charm, privacy and everyday livability in one of Fairfield's most sought after locations. Enjoy easy access to Greenfield Center, a quick drive to Westport and a convenient direct route to Fairfield Train Station, just 3.5 miles away. This classic center hall Cape is warm, inviting and easy to love. The main level features a living room with fireplace, traditional dining room, functional kitchen, an oversized rear family room that creates wonderful additional living space and a full bath. In addition, there is a flexible first floor room, currently used as additional living space and a home office, adds convenience for today's lifestyle while offering options for guests, work from home or future needs. Upstairs, two generously sized bedrooms share a full bath off the center hall. One bedroom was previously two bedroom rooms, offering added flexibility within the existing footprint if desired to convert back to three bedrooms. Perfect for downsizers, first time Greenfield Hill buyers or anyone seeking privacy, land and location, this home offers immediate appeal with meaningful long term potential. Move right in, enjoy the charm and explore future possibilities at your own pace in a beloved Fairfield neighborhood.

209 Merwins Ln, Fairfield

$1,550,000

Priced below market value for quick sale! Welcome to 355 Surrey Lane - an extensively renovated home where timeless design meets California contemporary and modern organic luxury finishes. Taken down to the studs and rebuilt with exceptional attention to detail and quality, this turnkey home offers the peace of mind of new construction on a level, private 1 acre lot with an enormous backyard and circular driveway in the highly sought after Greenfield Hill neighborhood. Just about every component of this home is brand new to include: AC, Gas Furnace, ductwork, hot water heater, electrical panel and systems, Anderson windows throughout, kitchen cabinets, premium Kitchenaid appliances and 48 inch double gas oven all under manufacturer warranty, 10 foot quartz waterfall island and laundry. Brand new wide plank engineered hardwood floors throughout the home and 3 fully renovated bathrooms. The living areas feature a wide open floorplan, perfect for entertaining and are highlighted by two striking floor to ceiling fireplaces. The home features expansive windows and doors, filling the home with natural light. Low utility bills from all new energy efficient insulation throughout. Huge additional living room/play room. In-law suite with private entrance and bath. Located minutes from major commuting routes and Fairfield's award winning schools, beaches, parks, restaurants, shopping and train. Hurry - this one will not last long

4 Beds ⋅ 4 Baths ⋅ 24179417 MLS

Priced below market value for quick sale! Welcome to 355 Surrey Lane - an extensively renovated home where timeless design meets California contemporary and modern organic luxury finishes. Taken down to the studs and rebuilt with exceptional attention to detail and quality, this turnkey home offers the peace of mind of new construction on a level, private 1 acre lot with an enormous backyard and circular driveway in the highly sought after Greenfield Hill neighborhood. Just about every component of this home is brand new to include: AC, Gas Furnace, ductwork, hot water heater, electrical panel and systems, Anderson windows throughout, kitchen cabinets, premium Kitchenaid appliances and 48 inch double gas oven all under manufacturer warranty, 10 foot quartz waterfall island and laundry. Brand new wide plank engineered hardwood floors throughout the home and 3 fully renovated bathrooms. The living areas feature a wide open floorplan, perfect for entertaining and are highlighted by two striking floor to ceiling fireplaces. The home features expansive windows and doors, filling the home with natural light. Low utility bills from all new energy efficient insulation throughout. Huge additional living room/play room. In-law suite with private entrance and bath. Located minutes from major commuting routes and Fairfield's award winning schools, beaches, parks, restaurants, shopping and train. Hurry - this one will not last long

355 Surrey 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

$2,220,000

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

$1,380,000

HIGHEST AND BEST TUES 5/19/26 AT 2 PM. Welcome to 223 Mistywood Lane - a beautifully maintained 4-bedroom, 2.5-bath retreat offering privacy and tranquility on over 2 picturesque acres. Filled with natural light, this inviting residence features recently remodeled bathrooms, hardwood floors throughout, fresh interior paint, and a thoughtfully designed layout ideal for both everyday living and entertaining. The bright kitchen is both stylish and functional, showcasing granite countertops, a charming shiplap backsplash, new appliances, a spacious walk-in pantry, and a designated dining area with a wood-burning fireplace. The stunning sun-filled room lined with windows creates the perfect space to relax and enjoy views of the beautifully landscaped gardens and serene surroundings. The second floor features four bedrooms, including a spacious primary suite with an oversized dressing room and a large en-suite bath with a soaking tub. A beautifully designed laundry room adds convenience and character to the home's well-appointed living spaces. Adding to the property's appeal is a recently remodeled barn-style garage with a finished bonus space above, offering endless flexibility as a playroom, home gym or studio. Surrounded by beautiful gardens and peaceful outdoor spaces, this exceptional property offers a rare combination of privacy, character, and convenience. Recent updates include a new well water pump and a high-efficiency propane boiler, providing added peace of mind

4 Beds ⋅ 3 Baths ⋅ 24175165 MLS

HIGHEST AND BEST TUES 5/19/26 AT 2 PM. Welcome to 223 Mistywood Lane - a beautifully maintained 4-bedroom, 2.5-bath retreat offering privacy and tranquility on over 2 picturesque acres. Filled with natural light, this inviting residence features recently remodeled bathrooms, hardwood floors throughout, fresh interior paint, and a thoughtfully designed layout ideal for both everyday living and entertaining. The bright kitchen is both stylish and functional, showcasing granite countertops, a charming shiplap backsplash, new appliances, a spacious walk-in pantry, and a designated dining area with a wood-burning fireplace. The stunning sun-filled room lined with windows creates the perfect space to relax and enjoy views of the beautifully landscaped gardens and serene surroundings. The second floor features four bedrooms, including a spacious primary suite with an oversized dressing room and a large en-suite bath with a soaking tub. A beautifully designed laundry room adds convenience and character to the home's well-appointed living spaces. Adding to the property's appeal is a recently remodeled barn-style garage with a finished bonus space above, offering endless flexibility as a playroom, home gym or studio. Surrounded by beautiful gardens and peaceful outdoor spaces, this exceptional property offers a rare combination of privacy, character, and convenience. Recent updates include a new well water pump and a high-efficiency propane boiler, providing added peace of mind

223 Mistywood Ln, Fairfield

$1,580,000

A once-in-a-generation Japanese-inspired 3 acre sanctuary on the coveted Westport side of Greenfield Hill, this extraordinary property offers a rare fusion of architecture, artistry, and landscape. Designed by the owner, a master gardener, the grounds unfold as a private retreat where the Sasco River winds through natural boulders, hand-laid stone walls, flowering specimen trees, terraced gardens, and peaceful woodland paths. The striking contemporary residence is equally compelling, with an open floor plan anchored by a dramatic cathedral-ceilinged living room. A centrally positioned mission-style kitchen serves as the heart of the home, while the dining room, sunroom, and family room enjoy sun-filled southern exposure and tranquil garden views. A dedicated art gallery and exceptional custom library further distinguish the main level. The main floor also includes the primary suite and two additional bedrooms, while a private third-floor bedroom with full bath offers ideal guest or office space. The walk-out lower level adds a family room plus a separate apartment with kitchenette, sitting area, bedroom, and full bath. Ready for thoughtful updates, this is a rare opportunity to reimagine and elevate a truly special home in one of Greenfield Hill's most peaceful and breathtaking settings. Minutes to Southport/Fairfield and Westport centers. House is not in a flood zone! Sits up high with a view!

5 Beds ⋅ 5 Baths ⋅ 24167159 MLS

A once-in-a-generation Japanese-inspired 3 acre sanctuary on the coveted Westport side of Greenfield Hill, this extraordinary property offers a rare fusion of architecture, artistry, and landscape. Designed by the owner, a master gardener, the grounds unfold as a private retreat where the Sasco River winds through natural boulders, hand-laid stone walls, flowering specimen trees, terraced gardens, and peaceful woodland paths. The striking contemporary residence is equally compelling, with an open floor plan anchored by a dramatic cathedral-ceilinged living room. A centrally positioned mission-style kitchen serves as the heart of the home, while the dining room, sunroom, and family room enjoy sun-filled southern exposure and tranquil garden views. A dedicated art gallery and exceptional custom library further distinguish the main level. The main floor also includes the primary suite and two additional bedrooms, while a private third-floor bedroom with full bath offers ideal guest or office space. The walk-out lower level adds a family room plus a separate apartment with kitchenette, sitting area, bedroom, and full bath. Ready for thoughtful updates, this is a rare opportunity to reimagine and elevate a truly special home in one of Greenfield Hill's most peaceful and breathtaking settings. Minutes to Southport/Fairfield and Westport centers. House is not in a flood zone! Sits up high with a view!

155 Labbance Ln, 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

$1,300,000

Location, location, location! Welcome to this delightful contemporary located at the end of a quiet cul-de-sac in lovely Greenfield Hill. With 4 bedrooms, 2.5 baths and a floor plan offering numerous possibilities for today's living and work lifestyles, this home checks so many boxes. A gracious Living Rm with vaulted ceiling brings the outside in with a wall of windows along the back. Enjoy a lovely view of the trees and backyard as soon as you step in the entry. A formal Dining Rm with built-in buffet and a nice Screened Porch with bluestone floor, also open to the back. The large bright Kitchen has granite countertops, separate island with cooktop, an eat-in Breakfast area, walk-in pantry and new GE Cafe appliances added in the Fall of 2021. Upper level has a Primary Bedroom with a spacious walk-in closet. Prepared to be wowed with the fully updated en-suite bath with soaking tub and separate shower. Two additional bedrooms with a full Bath along with large hallway closets for storage complete the floor. Lower level has a Family Room with wood-burning fireplace and built-in bookshelves. Off this room is the 4th Bedroom, with an Office in back. The finished Basement below offers even more space for play and relaxation. Lovingly cared for by the same family for 25 years, other notable features include a full house generator plumbed to the gas line and a new furnace in October 2020. Ask agent for additional features - you don't want to miss seeing this one!

4 Beds ⋅ 3 Baths ⋅ 24168777 MLS

Location, location, location! Welcome to this delightful contemporary located at the end of a quiet cul-de-sac in lovely Greenfield Hill. With 4 bedrooms, 2.5 baths and a floor plan offering numerous possibilities for today's living and work lifestyles, this home checks so many boxes. A gracious Living Rm with vaulted ceiling brings the outside in with a wall of windows along the back. Enjoy a lovely view of the trees and backyard as soon as you step in the entry. A formal Dining Rm with built-in buffet and a nice Screened Porch with bluestone floor, also open to the back. The large bright Kitchen has granite countertops, separate island with cooktop, an eat-in Breakfast area, walk-in pantry and new GE Cafe appliances added in the Fall of 2021. Upper level has a Primary Bedroom with a spacious walk-in closet. Prepared to be wowed with the fully updated en-suite bath with soaking tub and separate shower. Two additional bedrooms with a full Bath along with large hallway closets for storage complete the floor. Lower level has a Family Room with wood-burning fireplace and built-in bookshelves. Off this room is the 4th Bedroom, with an Office in back. The finished Basement below offers even more space for play and relaxation. Lovingly cared for by the same family for 25 years, other notable features include a full house generator plumbed to the gas line and a new furnace in October 2020. Ask agent for additional features - you don't want to miss seeing this one!

112 Calico Ln, 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

$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

$1,300,000

Nestled in the heart of coveted Greenfield Hill, this beautiful classic New England Colonial blends timeless charm, modern comfort & exceptional privacy. Set on 3.5 picturesque acres, the property feels like a private retreat yet is just minutes from town, beaches & Fairfield's top-rated schools. Designed for everyday living & entertaining, the home offers over 4,000 sq ft of thoughtfully designed space with sun-filled rooms & hardwood floors. The heart of the home is a spacious eat-in kitchen with stainless steel appliances plus a built-in bar area flowing into the inviting living room with a fireplace & large windows overlooking the serene property, perfect for gathering with family & friends. A dramatic family room with vaulted ceilings, fireplace & sliding doors leads to a large deck for seamless indoor-outdoor living surrounded by nature. The light-filled primary suite is a true sanctuary with a walk-in closet, fireplace, a luxurious spa-like bath with Carrara marble, heated floors & a soaking tub. The finished 3rd floor offers a 4th bedroom & full bath/versatile bonus space (au pair suite, office, playroom). A walk-out lower level has flexible space for a playroom, office or gym, plus a nearby stone patio. Expansive grounds feature open lawn, gardens, full deer fencing, mature trees, a tranquil brook-perfect for relaxing or entertaining in a peaceful natural setting. This timeless, elegant Greenfield Hill home with exceptional space & privacy is a rare opportunity.

4 Beds ⋅ 4 Baths ⋅ 24161267 MLS

Nestled in the heart of coveted Greenfield Hill, this beautiful classic New England Colonial blends timeless charm, modern comfort & exceptional privacy. Set on 3.5 picturesque acres, the property feels like a private retreat yet is just minutes from town, beaches & Fairfield's top-rated schools. Designed for everyday living & entertaining, the home offers over 4,000 sq ft of thoughtfully designed space with sun-filled rooms & hardwood floors. The heart of the home is a spacious eat-in kitchen with stainless steel appliances plus a built-in bar area flowing into the inviting living room with a fireplace & large windows overlooking the serene property, perfect for gathering with family & friends. A dramatic family room with vaulted ceilings, fireplace & sliding doors leads to a large deck for seamless indoor-outdoor living surrounded by nature. The light-filled primary suite is a true sanctuary with a walk-in closet, fireplace, a luxurious spa-like bath with Carrara marble, heated floors & a soaking tub. The finished 3rd floor offers a 4th bedroom & full bath/versatile bonus space (au pair suite, office, playroom). A walk-out lower level has flexible space for a playroom, office or gym, plus a nearby stone patio. Expansive grounds feature open lawn, gardens, full deer fencing, mature trees, a tranquil brook-perfect for relaxing or entertaining in a peaceful natural setting. This timeless, elegant Greenfield Hill home with exceptional space & privacy is a rare opportunity.

3725 Redding Rd, 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

$2,215,000

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

$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

$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

$977,000

RESPECTFULLY; PLEASE SUBMIT HIGHEST AND BEST BY MONDAY 27TH @ 6 PM. Everything Retouched | 2+ Acres | Expansion Opportunity Located in desirable Greenfield Hill, this fully remodeled single-level ranch offers estate-style living with exceptional expansion potential. Set on over 2 level acres-the smallest home on a street of significantly larger residences-this property presents a rare opportunity to build equity and expand. The usable yard features stone walls, classic New England charm, and privacy, with inland wetlands toward the rear. Ample space for outdoor living or a future pool, plus a chicken coop and storage barn/shed for added versatility. Exterior features include a newer roof, gutter guards, new cedar shingles, cable railing, cedar tongue-and-groove deck ceiling, and high-end materials throughout. Take note of the incredible screened-in back deck, composite front porch, new windows, attached 2-car garage, and storage shed. Above-and-beyond mechanicals include propane heat fueled home w/ two, 100 gallon tanks, Trane HVAC central air, Takagi tankless hot water, fully fenced backyard, and Generac generator. Freshly painted interior with hardwood floors, updated kitchen with extensive cabinetry, quartz island, coffee bar, pantry, and abundant storage. Additional highlights include an ensuite primary bedroom, fireplaced living room, ceiling fans, full unfinished basement spanning the home, and smart home Lutron Caseta system. See full list of highlights and features.

3 Beds ⋅ 2 Baths ⋅ 24167637 MLS

RESPECTFULLY; PLEASE SUBMIT HIGHEST AND BEST BY MONDAY 27TH @ 6 PM. Everything Retouched | 2+ Acres | Expansion Opportunity Located in desirable Greenfield Hill, this fully remodeled single-level ranch offers estate-style living with exceptional expansion potential. Set on over 2 level acres-the smallest home on a street of significantly larger residences-this property presents a rare opportunity to build equity and expand. The usable yard features stone walls, classic New England charm, and privacy, with inland wetlands toward the rear. Ample space for outdoor living or a future pool, plus a chicken coop and storage barn/shed for added versatility. Exterior features include a newer roof, gutter guards, new cedar shingles, cable railing, cedar tongue-and-groove deck ceiling, and high-end materials throughout. Take note of the incredible screened-in back deck, composite front porch, new windows, attached 2-car garage, and storage shed. Above-and-beyond mechanicals include propane heat fueled home w/ two, 100 gallon tanks, Trane HVAC central air, Takagi tankless hot water, fully fenced backyard, and Generac generator. Freshly painted interior with hardwood floors, updated kitchen with extensive cabinetry, quartz island, coffee bar, pantry, and abundant storage. Additional highlights include an ensuite primary bedroom, fireplaced living room, ceiling fans, full unfinished basement spanning the home, and smart home Lutron Caseta system. See full list of highlights and features.

208 Wildflower Ln, 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

$1,600,000

HIGHEST & BEST DUE BY SUNDAY 2/22 9PM. Discover this charming home, originally built in 1945, in the heart of Greenfield Hill, boasting 3 spacious bedrooms and 2.5 baths with large rooms throughout for comfortable living. The inviting updated, eat-in kitchen features a central island, modern appliances, and plenty of storage. Three wood-burning fireplaces on the first floor with beautiful hearths add warmth and ambiance, while gleaming hardwood floors flow seamlessly across the entire home, complemented by an oversized living room and dining room ideal for entertaining. The kitchen, as well as the family room, complete with custom built-ins and a dedicated gaming area, opens directly to the beautiful and durable Ipe deck for seamless indoor-outdoor living. The property features a cedar roof on the main house; and an asphalt roof on the large two-car garage. Ideally situated just a short stroll to "the shadow of the steeple," site of the cherished annual Dogwood Festival each May, and conveniently close to a charming local farm, adjacent open space, and highly rated schools. Only minutes from the vibrant downtowns of Fairfield and Westport. Enjoy peaceful walks, jogs, or bike rides along quiet, tree-lined streets, embracing the serene New England countryside charm. Commuting is effortless, with the Metro North train station to NYC, downtown shops, restaurants, the YMCA & the main library all just a quick 5-7 minute drive away. Natural gas &city water utilities.

3 Beds ⋅ 3 Baths ⋅ 24151463 MLS

HIGHEST & BEST DUE BY SUNDAY 2/22 9PM. Discover this charming home, originally built in 1945, in the heart of Greenfield Hill, boasting 3 spacious bedrooms and 2.5 baths with large rooms throughout for comfortable living. The inviting updated, eat-in kitchen features a central island, modern appliances, and plenty of storage. Three wood-burning fireplaces on the first floor with beautiful hearths add warmth and ambiance, while gleaming hardwood floors flow seamlessly across the entire home, complemented by an oversized living room and dining room ideal for entertaining. The kitchen, as well as the family room, complete with custom built-ins and a dedicated gaming area, opens directly to the beautiful and durable Ipe deck for seamless indoor-outdoor living. The property features a cedar roof on the main house; and an asphalt roof on the large two-car garage. Ideally situated just a short stroll to "the shadow of the steeple," site of the cherished annual Dogwood Festival each May, and conveniently close to a charming local farm, adjacent open space, and highly rated schools. Only minutes from the vibrant downtowns of Fairfield and Westport. Enjoy peaceful walks, jogs, or bike rides along quiet, tree-lined streets, embracing the serene New England countryside charm. Commuting is effortless, with the Metro North train station to NYC, downtown shops, restaurants, the YMCA & the main library all just a quick 5-7 minute drive away. Natural gas &city water utilities.

3674 Congress St, Fairfield

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