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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

$1,850,000

254 Sherwood Farm Road, tucked away at the end of a cul-de-sac in the desirable lower Greenfield Hill section of Fairfield, this stately brick Colonial blends timeless curb appeal with a flexible floor plan and rare amenities. Mature plantings, stone walkways, and professional landscape lighting frame the home with elegance from the moment you arrive. Inside, the first level offers remarkable versatility with an en-suite bedroom featuring a walk-in closet, a dedicated office, a large chef's kitchen with an impressive Wolf and Sub-Zero appliance package, and dining and living rooms that soar with elevated ceiling heights, bringing light and luxury to the main living spaces. Upstairs, the well-proportioned primary suite is a retreat with dual walk-in closets and a spa-like bath. The oversized shower is outfitted as a steam shower-an ideal sauna alternative-while two additional bedrooms share a dual bath. The fully finished lower level serves as a true multi-generational apartment, complete with a full kitchen, laundry, and full bath, opening directly to the backyard stone patio, private yard, and in-ground pool with a built-in waterfall feature-ideal for entertaining or quiet relaxation. Additional highlights include an oversized three-car garage, whole-house generator, advanced air-filtration HVAC system, and a private yet convenient Greenfield Hill location.This combination of style, flexibility, and amenities makes 254 Sherwood Farm Road a rare and exceptional property.

4 Beds ⋅ 5 Baths ⋅ 24129933 MLS

254 Sherwood Farm Road, tucked away at the end of a cul-de-sac in the desirable lower Greenfield Hill section of Fairfield, this stately brick Colonial blends timeless curb appeal with a flexible floor plan and rare amenities. Mature plantings, stone walkways, and professional landscape lighting frame the home with elegance from the moment you arrive. Inside, the first level offers remarkable versatility with an en-suite bedroom featuring a walk-in closet, a dedicated office, a large chef's kitchen with an impressive Wolf and Sub-Zero appliance package, and dining and living rooms that soar with elevated ceiling heights, bringing light and luxury to the main living spaces. Upstairs, the well-proportioned primary suite is a retreat with dual walk-in closets and a spa-like bath. The oversized shower is outfitted as a steam shower-an ideal sauna alternative-while two additional bedrooms share a dual bath. The fully finished lower level serves as a true multi-generational apartment, complete with a full kitchen, laundry, and full bath, opening directly to the backyard stone patio, private yard, and in-ground pool with a built-in waterfall feature-ideal for entertaining or quiet relaxation. Additional highlights include an oversized three-car garage, whole-house generator, advanced air-filtration HVAC system, and a private yet convenient Greenfield Hill location.This combination of style, flexibility, and amenities makes 254 Sherwood Farm Road a rare and exceptional property.

254 Sherwood Farm Rd, 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

$1,650,000

A gracious front porch welcomes you to this sophisticated colonial where comfort and luxury abound. The entry hall with striking floor to ceiling picture frame molding, setting the tone for the refined details found throughout the home. The family room greets you with many carefully curated features including book shelves framing the entry, coffered ceiling, gas fireplace flanked by built in window seats and an entertainment cabinet. The paneled den/library offers a cozy retreat with a wood burning fireplace, exposed beams, custom built ins and inset desk. Relax in the sunroom with barn door style trim and a wall of windows overlooking the private yard. The kitchen is a masterpiece with its bespoke cabinetry including a wall of glass front upper cabinets and walnut trim, curved island with walnut top, bar sink, and wine frig, granite countertops, high end appliances with pot filler at the cooktop, oil rubbed bronze hardware and built in desk area with walnut top, recessed cabinetry and framed bulletin board backsplash. The kitchen opens into the dining room featuring a tray ceiling, built in hutch and buffet, wall of windows, and french door leading to a stone patio and yard, as well as family and sun room providing great flow for entertaining. The primary suite features a cedar lined walk in closet, fireplace, balcony, a wall of custom built ins with vanity and mirror, and two wardrobes and a sitting area with vaulted ceiling and sliders to a covered balcony. (see addendum)

6 Beds ⋅ 4 Baths ⋅ 24109911 MLS

A gracious front porch welcomes you to this sophisticated colonial where comfort and luxury abound. The entry hall with striking floor to ceiling picture frame molding, setting the tone for the refined details found throughout the home. The family room greets you with many carefully curated features including book shelves framing the entry, coffered ceiling, gas fireplace flanked by built in window seats and an entertainment cabinet. The paneled den/library offers a cozy retreat with a wood burning fireplace, exposed beams, custom built ins and inset desk. Relax in the sunroom with barn door style trim and a wall of windows overlooking the private yard. The kitchen is a masterpiece with its bespoke cabinetry including a wall of glass front upper cabinets and walnut trim, curved island with walnut top, bar sink, and wine frig, granite countertops, high end appliances with pot filler at the cooktop, oil rubbed bronze hardware and built in desk area with walnut top, recessed cabinetry and framed bulletin board backsplash. The kitchen opens into the dining room featuring a tray ceiling, built in hutch and buffet, wall of windows, and french door leading to a stone patio and yard, as well as family and sun room providing great flow for entertaining. The primary suite features a cedar lined walk in closet, fireplace, balcony, a wall of custom built ins with vanity and mirror, and two wardrobes and a sitting area with vaulted ceiling and sliders to a covered balcony. (see addendum)

312 Towne House 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

$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

$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

$1,600,000

Welcome to this beautifully updated 4+ bedroom Colonial in a sought-after Greenfield Hill neighborhood, surrounded by rolling lawns and tree-lined streets. Offering over 3,000 sq. ft. of elegant living space plus 1,000+ sq. ft. in the spacious finished walk-out lower level, this home provides exceptional versatility and comfort. The grand entryway opens to a formal living and dining room with custom built-ins. The inviting family room, with vaulted ceilings and a natural stone fireplace, flows seamlessly into the impeccably updated eat-in kitchen. From here, sliding doors lead to an expansive Trex deck with a built-in gas grill, perfect for indoor/outdoor entertaining against the backdrop of a serene, private wooded yard. A mudroom, laundry area, and powder room complete the first floor. Upstairs, the tranquil primary suite features a walk-in closet and a spa-like bath with soaking tub, stall shower, and double vanity. Three additional bedrooms and a full bath complete the second level. The finished lower level includes a bedroom/office/potential au pair suite with full bath, ample storage, and walk-out access. Notable upgrades include fresh interior and exterior paint (2025), new roof (2024), remodeled kitchen and primary bath (2023), refinished hardwood floors (2023), and driveway sealing (2023). Meticulously maintained mechanicals and thoughtful updates make this home truly move-in ready.

4 Beds ⋅ 4 Baths ⋅ 24126270 MLS

Welcome to this beautifully updated 4+ bedroom Colonial in a sought-after Greenfield Hill neighborhood, surrounded by rolling lawns and tree-lined streets. Offering over 3,000 sq. ft. of elegant living space plus 1,000+ sq. ft. in the spacious finished walk-out lower level, this home provides exceptional versatility and comfort. The grand entryway opens to a formal living and dining room with custom built-ins. The inviting family room, with vaulted ceilings and a natural stone fireplace, flows seamlessly into the impeccably updated eat-in kitchen. From here, sliding doors lead to an expansive Trex deck with a built-in gas grill, perfect for indoor/outdoor entertaining against the backdrop of a serene, private wooded yard. A mudroom, laundry area, and powder room complete the first floor. Upstairs, the tranquil primary suite features a walk-in closet and a spa-like bath with soaking tub, stall shower, and double vanity. Three additional bedrooms and a full bath complete the second level. The finished lower level includes a bedroom/office/potential au pair suite with full bath, ample storage, and walk-out access. Notable upgrades include fresh interior and exterior paint (2025), new roof (2024), remodeled kitchen and primary bath (2023), refinished hardwood floors (2023), and driveway sealing (2023). Meticulously maintained mechanicals and thoughtful updates make this home truly move-in ready.

550 Rolling Hills Dr, Fairfield

$1,587,500

Tucked away at the end of a tranquil cul-de-sac in one of Greenfield Hill's most convenient and desirable neighborhoods, this turn-key New England Colonial offers the perfect blend of timeless style, classic design and an exceptional lifestyle at any stage of life. Designed for everyday living and entertaining. Features include an inviting foyer with custom molding, powder room, refinished hardwood floors, Marvin windows, sun-filled formal living and dining rooms. The beautiful granite eat-in kitchen has custom cabinetry, newer appliances, an oversized walk-in pantry and 1st floor laundry. A welcoming family room showcases new custom built-ins and wood burning fireplace with seamless access for indoor-outdoor flow. Upstairs, a spacious primary suite offers a walk-in closet and updated private bath while three additional generously sized bedrooms with ample closet space share the hall bath. Finished lower level expands the living space with a rec room, office area and plenty of storage. Professionally landscaped, flat, one acre fenced rear property with raised garden beds, shed, expanded trex deck with pergola and retractable awning creates an oasis for outdoor living and entertaining. The 'circle' is where bike rides and Easter egg hunts begin and neighbors gather creating a real sense of community. Minutes to town, beach, award winning schools and commuter options.

4 Beds ⋅ 3 Baths ⋅ 24187463 MLS

Tucked away at the end of a tranquil cul-de-sac in one of Greenfield Hill's most convenient and desirable neighborhoods, this turn-key New England Colonial offers the perfect blend of timeless style, classic design and an exceptional lifestyle at any stage of life. Designed for everyday living and entertaining. Features include an inviting foyer with custom molding, powder room, refinished hardwood floors, Marvin windows, sun-filled formal living and dining rooms. The beautiful granite eat-in kitchen has custom cabinetry, newer appliances, an oversized walk-in pantry and 1st floor laundry. A welcoming family room showcases new custom built-ins and wood burning fireplace with seamless access for indoor-outdoor flow. Upstairs, a spacious primary suite offers a walk-in closet and updated private bath while three additional generously sized bedrooms with ample closet space share the hall bath. Finished lower level expands the living space with a rec room, office area and plenty of storage. Professionally landscaped, flat, one acre fenced rear property with raised garden beds, shed, expanded trex deck with pergola and retractable awning creates an oasis for outdoor living and entertaining. The 'circle' is where bike rides and Easter egg hunts begin and neighbors gather creating a real sense of community. Minutes to town, beach, award winning schools and commuter options.

107 Buckboard 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

$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

$1,530,000

Private Greenfield Hill Retreat on 2+ Acres with Guest Suite, Modern Updates & Equestrian Potential.Tucked away on a quiet cul-de-sac in the heart of Greenfield Hill, this rare property offers privacy, flexibility, and modern comfort. From the moment you enter, the craftsmanship is unmistakable featuring a handcrafted staircase, custom millwork, built-ins, and a dramatic barrel ceiling living room anchored by a stone fireplace. The refreshed chef's kitchen includes a center island, double ovens, pantry, and granite countertops, opening to a sun filled sitting area with views of mature plantings. The floor plan offers exceptional versatility. A first floor wing, currently configured as an in-law suite with full kitchen, bedroom, full bath, walk-in closet, and laundry, can easily function as a primary suite, guest retreat, or additional bedroom adapting seamlessly to changing needs. Upstairs, you'll find two addt'l ensuite bedrooms, a cedar closet, and generous walk in storage, providing privacy and comfort throughout. Addt'l highlights include new main level flooring, upgraded lighting, a whole house generator, and reverse osmosis water filtration system, offering both convenience and peace of mind. Outside, a stone terrace overlooks the expansive backyard, while a separate outbuilding provides space for addt'l vehicles, a workshop, or equestrian use. Ideally located near both Fairfield and Westport, the property feels completely private while remaining close to everything.

3 Beds ⋅ 4 Baths ⋅ 24179278 MLS

Private Greenfield Hill Retreat on 2+ Acres with Guest Suite, Modern Updates & Equestrian Potential.Tucked away on a quiet cul-de-sac in the heart of Greenfield Hill, this rare property offers privacy, flexibility, and modern comfort. From the moment you enter, the craftsmanship is unmistakable featuring a handcrafted staircase, custom millwork, built-ins, and a dramatic barrel ceiling living room anchored by a stone fireplace. The refreshed chef's kitchen includes a center island, double ovens, pantry, and granite countertops, opening to a sun filled sitting area with views of mature plantings. The floor plan offers exceptional versatility. A first floor wing, currently configured as an in-law suite with full kitchen, bedroom, full bath, walk-in closet, and laundry, can easily function as a primary suite, guest retreat, or additional bedroom adapting seamlessly to changing needs. Upstairs, you'll find two addt'l ensuite bedrooms, a cedar closet, and generous walk in storage, providing privacy and comfort throughout. Addt'l highlights include new main level flooring, upgraded lighting, a whole house generator, and reverse osmosis water filtration system, offering both convenience and peace of mind. Outside, a stone terrace overlooks the expansive backyard, while a separate outbuilding provides space for addt'l vehicles, a workshop, or equestrian use. Ideally located near both Fairfield and Westport, the property feels completely private while remaining close to everything.

1180 Merwins Ln, Fairfield

$1,500,000

Rich in character and designed for today's lifestyle, this distinctive Fairfield home is privately set on two picturesque acres, framed by classic New England stone walls, white fencing, mature trees, open lawns, a quintessential red barn, and a detached two-car garage. The setting offers exceptional privacy while beautifully balancing Fairfield's country landscape with the convenience of its location. Thoughtfully renovated and expanded in 2012, the home offers an elevated, modern living experience while preserving the architectural details that make the property unique. The beautifully appointed chef's kitchen, with top-of-the-line appliances, opens seamlessly to a great room with soaring vaulted ceilings, a handsome fireplace, walls of windows overlooking the property, and sliders to the private deck. Designed for both entertaining and everyday living, the open layout creates a natural gathering place and an effortless connection to the outdoors. Adding to the home's timeless character are its circa-1749 origins, beautifully preserved through select period details, including the King's Board flooring-an architectural feature traditionally found in some of New England's earliest homes. An adjoining room offers exceptional flexibility as a library, study, or intimate sitting room.

4 Beds ⋅ 4 Baths ⋅ 24047873 MLS

Rich in character and designed for today's lifestyle, this distinctive Fairfield home is privately set on two picturesque acres, framed by classic New England stone walls, white fencing, mature trees, open lawns, a quintessential red barn, and a detached two-car garage. The setting offers exceptional privacy while beautifully balancing Fairfield's country landscape with the convenience of its location. Thoughtfully renovated and expanded in 2012, the home offers an elevated, modern living experience while preserving the architectural details that make the property unique. The beautifully appointed chef's kitchen, with top-of-the-line appliances, opens seamlessly to a great room with soaring vaulted ceilings, a handsome fireplace, walls of windows overlooking the property, and sliders to the private deck. Designed for both entertaining and everyday living, the open layout creates a natural gathering place and an effortless connection to the outdoors. Adding to the home's timeless character are its circa-1749 origins, beautifully preserved through select period details, including the King's Board flooring-an architectural feature traditionally found in some of New England's earliest homes. An adjoining room offers exceptional flexibility as a library, study, or intimate sitting room.

1495 Westport Tpke, Fairfield

$1,500,000

Picture coming home to your own Custom Colonial sitting on over half a private acre on a quiet, tree-lined street in lower Greenfield Hill, where you're minutes from everything but feel worlds away. An expansive front porch invites you to slow down the second you pull in. Inside, sunlight pours through every room and hardwood floors gleam underfoot. The high-end, spacious kitchen is made for gathering - an oversized island, quartz counters, marble backsplash, and Thermador & Bosch stainless appliances bring everyone into one open, functional space. A separate office with custom built-ins and a fireplace offers a quiet retreat for work or reading. The vaulted family room opens straight onto a 3-season screened-in porch offering a continuous indoor/outdoor living space. Upstairs, retreat to your spacious and newly renovated primary suite built for rest. It features a spa bath, soaking tub, radiant heated floors, and a walk-in closet that actually fits everything. Three more bedrooms, each with custom closets, share an updated bath with granite countertops and double sinks. Custom interior wooden shutters, a premium-flooring 2-car garage, whole-house Generac generator, new A/C, new washer/dryer bolster this as a home where there is nothing left for you to do. Move-in ready, in one of the area's most sought-after neighborhoods served by award-winning schools. Come see it before someone else calls it home.

4 Beds ⋅ 3 Baths ⋅ 24189763 MLS

Picture coming home to your own Custom Colonial sitting on over half a private acre on a quiet, tree-lined street in lower Greenfield Hill, where you're minutes from everything but feel worlds away. An expansive front porch invites you to slow down the second you pull in. Inside, sunlight pours through every room and hardwood floors gleam underfoot. The high-end, spacious kitchen is made for gathering - an oversized island, quartz counters, marble backsplash, and Thermador & Bosch stainless appliances bring everyone into one open, functional space. A separate office with custom built-ins and a fireplace offers a quiet retreat for work or reading. The vaulted family room opens straight onto a 3-season screened-in porch offering a continuous indoor/outdoor living space. Upstairs, retreat to your spacious and newly renovated primary suite built for rest. It features a spa bath, soaking tub, radiant heated floors, and a walk-in closet that actually fits everything. Three more bedrooms, each with custom closets, share an updated bath with granite countertops and double sinks. Custom interior wooden shutters, a premium-flooring 2-car garage, whole-house Generac generator, new A/C, new washer/dryer bolster this as a home where there is nothing left for you to do. Move-in ready, in one of the area's most sought-after neighborhoods served by award-winning schools. Come see it before someone else calls it home.

485 Mountain Laurel Rd, Fairfield

$1,500,000

Move-in ready and freshly updated, this expansive 5,000+ sq ft Colonial is located in the prestigious Ridge of Greenfield Hill-a 24-hour guard-gated community situated on the border of Fairfield and Westport. The Ridge offers a resort-style lifestyle with amenities including a heated pool, lighted tennis courts, pickle ball, playground, and a private recreation center-all set among 96 luxury homes on manicured grounds. This sun-drenched five-bedroom, six-bathroom home has been freshly painted inside and out and features extensive millwork, gleaming hardwood floors, and floor-to-ceiling windows that flood the home with natural light. The open-concept layout is ideal for entertaining, centered around a fully renovated gourmet kitchen with high-end appliances, custom cabinetry, and a large island, flowing seamlessly into the great room and out to a spacious patio. Upstairs, generous bedrooms include a luxurious primary suite, while flexible living spaces throughout the home cater to modern lifestyles-perfect for hosting or working from home. The flat, private yard offers multiple outdoor entertaining areas and is complemented by a three-car garage. Enjoy privacy and elegance while being just minutes from the vibrant downtowns of Fairfield and Westport, as well as local beaches and train stations. This is luxury living with everyday convenience-completely turnkey and ready for it's new homeowners.

5 Beds ⋅ 6 Baths ⋅ 24128652 MLS

Move-in ready and freshly updated, this expansive 5,000+ sq ft Colonial is located in the prestigious Ridge of Greenfield Hill-a 24-hour guard-gated community situated on the border of Fairfield and Westport. The Ridge offers a resort-style lifestyle with amenities including a heated pool, lighted tennis courts, pickle ball, playground, and a private recreation center-all set among 96 luxury homes on manicured grounds. This sun-drenched five-bedroom, six-bathroom home has been freshly painted inside and out and features extensive millwork, gleaming hardwood floors, and floor-to-ceiling windows that flood the home with natural light. The open-concept layout is ideal for entertaining, centered around a fully renovated gourmet kitchen with high-end appliances, custom cabinetry, and a large island, flowing seamlessly into the great room and out to a spacious patio. Upstairs, generous bedrooms include a luxurious primary suite, while flexible living spaces throughout the home cater to modern lifestyles-perfect for hosting or working from home. The flat, private yard offers multiple outdoor entertaining areas and is complemented by a three-car garage. Enjoy privacy and elegance while being just minutes from the vibrant downtowns of Fairfield and Westport, as well as local beaches and train stations. This is luxury living with everyday convenience-completely turnkey and ready for it's new homeowners.

101 Brambley Hedge Cir, Fairfield

$1,450,000

THANK YOU FOR YOUR STRONG INTEREST; SELLER REQUESTS HIGHEST & BEST OFFERS BY NOON ON MONDAY 3/16/26 thoughtfully updated Colonial in the heart of Greenfield Hill, 1115 Galloping Hill Road is the kind of home that simply feels right. Solid, balanced, and beautifully maintained, it reflects years of careful ownership and intentional improvement. The main level offers an easy flow between kitchen and family room, anchored by a classic brick fireplace and extending seamlessly to a screened sunroom that invites year-round enjoyment. The kitchen has been refreshed with new cabinet fronts, hardware, lighting, and a built-in breakfast nook. Refinished hardwood floors run throughout the home, unified in tone, while a crisp Chantilly Lace palette and curated fixtures create a cohesive, timeless feel. Upstairs, the primary suite is quietly refined, complemented by three additional bedrooms with custom closet systems, updated lighting, and thoughtful design details. The fully permitted lower level has been completely reimagined with new flooring, insulation, heating, windows, and generous storage. Exterior improvements include a widened driveway, new front door, expanded bluestone patio, refreshed landscaping, solar-reflective sunroom windows, and a level lawn enhanced for usability and privacy. Major systems, including septic, roof, windows, and electrical, have been updated. A home that feels settled, solid, and ready for its next chapter.

4 Beds ⋅ 3 Baths ⋅ 24132021 MLS

THANK YOU FOR YOUR STRONG INTEREST; SELLER REQUESTS HIGHEST & BEST OFFERS BY NOON ON MONDAY 3/16/26 thoughtfully updated Colonial in the heart of Greenfield Hill, 1115 Galloping Hill Road is the kind of home that simply feels right. Solid, balanced, and beautifully maintained, it reflects years of careful ownership and intentional improvement. The main level offers an easy flow between kitchen and family room, anchored by a classic brick fireplace and extending seamlessly to a screened sunroom that invites year-round enjoyment. The kitchen has been refreshed with new cabinet fronts, hardware, lighting, and a built-in breakfast nook. Refinished hardwood floors run throughout the home, unified in tone, while a crisp Chantilly Lace palette and curated fixtures create a cohesive, timeless feel. Upstairs, the primary suite is quietly refined, complemented by three additional bedrooms with custom closet systems, updated lighting, and thoughtful design details. The fully permitted lower level has been completely reimagined with new flooring, insulation, heating, windows, and generous storage. Exterior improvements include a widened driveway, new front door, expanded bluestone patio, refreshed landscaping, solar-reflective sunroom windows, and a level lawn enhanced for usability and privacy. Major systems, including septic, roof, windows, and electrical, have been updated. A home that feels settled, solid, and ready for its next chapter.

1115 Galloping Hill Rd, Fairfield

$1,403,000

*OFFERS DUE 5PM 9/21* Welcome to this quintessential New England colonial, lovingly cherished by the same owner for over 4 decades. On 2 flat, picturesque acres, this timeless home offers serene, private living while remaining centrally located. A sweeping circular driveway creates a warm arrival, while the sprawling, level backyard provides an ideal setting for outdoor entertaining, with room for a pool and pool house.Inside, traditional character shines with hardwood floors throughout. The main level is designed for both casual daily life and formal hosting. The heart of the home features an expansive eat-in kitchen anchored by a center island, ideal for morning coffee or casual gatherings. A formal living room centers around a fireplace, with classic French doors opening into the dining room. The main level also offers exceptional layout flexibility, including a light-filled office with French doors to a private flagstone patio, a cozy den, a family room with a second fireplace, and a practical mudroom with garage access to keep everyday life organized. Upstairs, 4 generous bedrooms include a primary with an oversized bathroom, the rare convenience of a true 2nd-floor laundry room, and a 2nd full bathroom with double sinks. For extra storage, a full walk-up attic provides additional space. Offering rare privacy, incredible space, and enduring quality in a prime location, this exceptional property presents a wonderful opportunity for its next owners to make it their

4 Beds ⋅ 3 Baths ⋅ 24206877 MLS

*OFFERS DUE 5PM 9/21* Welcome to this quintessential New England colonial, lovingly cherished by the same owner for over 4 decades. On 2 flat, picturesque acres, this timeless home offers serene, private living while remaining centrally located. A sweeping circular driveway creates a warm arrival, while the sprawling, level backyard provides an ideal setting for outdoor entertaining, with room for a pool and pool house.Inside, traditional character shines with hardwood floors throughout. The main level is designed for both casual daily life and formal hosting. The heart of the home features an expansive eat-in kitchen anchored by a center island, ideal for morning coffee or casual gatherings. A formal living room centers around a fireplace, with classic French doors opening into the dining room. The main level also offers exceptional layout flexibility, including a light-filled office with French doors to a private flagstone patio, a cozy den, a family room with a second fireplace, and a practical mudroom with garage access to keep everyday life organized. Upstairs, 4 generous bedrooms include a primary with an oversized bathroom, the rare convenience of a true 2nd-floor laundry room, and a 2nd full bathroom with double sinks. For extra storage, a full walk-up attic provides additional space. Offering rare privacy, incredible space, and enduring quality in a prime location, this exceptional property presents a wonderful opportunity for its next owners to make it their

1951 Burr St, 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

$1,400,000

A John Brackert built home on a very sought after cul-de-sac in lower Greenfield Hill. A true neighborhood of yesteryear, where youth can ride bikes in the street, you walk to the Greenfield Hill Corner Market for your hot coffee and breakfast sandwich, and the families gather on the weekdays at the bus stop for an old fashion chat and send off. 240 North Cedar has been in the owners happy and loving hands for 61 years. Lots of life, laughter, milestones, and gatherings have filled her walls and yard. Many friends, family, grandkids, and neighbors have shared times and yummy homemade meals and ice teas under her roof. Her charm and character are felt and seen. (Just look at her custom finials on either side of her front door). Her stories are real and well lived. Her laughter and joy loud. Yes, she needs some work, yes certain edges are worn, but this home, on this street, in this neighborhood, make her a home run. She is ready for her story to become your story.

4 Beds ⋅ 3 Baths ⋅ 24176616 MLS

A John Brackert built home on a very sought after cul-de-sac in lower Greenfield Hill. A true neighborhood of yesteryear, where youth can ride bikes in the street, you walk to the Greenfield Hill Corner Market for your hot coffee and breakfast sandwich, and the families gather on the weekdays at the bus stop for an old fashion chat and send off. 240 North Cedar has been in the owners happy and loving hands for 61 years. Lots of life, laughter, milestones, and gatherings have filled her walls and yard. Many friends, family, grandkids, and neighbors have shared times and yummy homemade meals and ice teas under her roof. Her charm and character are felt and seen. (Just look at her custom finials on either side of her front door). Her stories are real and well lived. Her laughter and joy loud. Yes, she needs some work, yes certain edges are worn, but this home, on this street, in this neighborhood, make her a home run. She is ready for her story to become your story.

240 N Cedar Rd, Fairfield

$1,400,000

Compelling Value in Greenfield Hill! Nestled amid mature trees and natural surroundings, this 5-bedroom, 4-bath home offers an exceptional combination of space, privacy, and functionality. The open living room and family room provide flexible living spaces with seamless access to the covered porch and expansive deck overlooking the peaceful setting and side yard. The spacious eat-in kitchen features abundant workspace, generous cabinetry, and room for casual dining. Adjacent to the kitchen, the dining room is equally suited for everyday meals and special occasions. A mudroom located just off the kitchen provides its own entrance and access to the oversized three-car garage. A unique spiral staircase offers secondary access to the primary suite. A dedicated main-level office and full bath add convenience and versatility. Upstairs, the spacious primary suite is complemented by four additional bedrooms and two full baths. The finished lower level provides generous bonus space for a playroom, media room, fitness area, or recreation room beyond the reported square footage. In addition to the attached three-car garage, a detached two-car garage offers valuable extra space for vehicles, bikes, equipment, hobbies, or creative use. Enjoy a private setting approximately 15 minutes from Fairfield Center, Westport, Easton, and Weston, with convenient access to shopping, dining, recreation, and transportation.Greenfield Hill living at an exceptional value!

5 Beds ⋅ 4 Baths ⋅ 24180399 MLS

Compelling Value in Greenfield Hill! Nestled amid mature trees and natural surroundings, this 5-bedroom, 4-bath home offers an exceptional combination of space, privacy, and functionality. The open living room and family room provide flexible living spaces with seamless access to the covered porch and expansive deck overlooking the peaceful setting and side yard. The spacious eat-in kitchen features abundant workspace, generous cabinetry, and room for casual dining. Adjacent to the kitchen, the dining room is equally suited for everyday meals and special occasions. A mudroom located just off the kitchen provides its own entrance and access to the oversized three-car garage. A unique spiral staircase offers secondary access to the primary suite. A dedicated main-level office and full bath add convenience and versatility. Upstairs, the spacious primary suite is complemented by four additional bedrooms and two full baths. The finished lower level provides generous bonus space for a playroom, media room, fitness area, or recreation room beyond the reported square footage. In addition to the attached three-car garage, a detached two-car garage offers valuable extra space for vehicles, bikes, equipment, hobbies, or creative use. Enjoy a private setting approximately 15 minutes from Fairfield Center, Westport, Easton, and Weston, with convenient access to shopping, dining, recreation, and transportation.Greenfield Hill living at an exceptional value!

4041 Redding 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

$1,355,500

This Greenfield hill Charming colonial, sits on a 1.6 acre lot, right at the border of Fairfield and Westport and only 6 away minutes from the Southport train station and multiple beautiful beaches. Cozy and stylish with a twist of French flair, this well maintained property offers, 5 bedrooms, including a nursery right by the primary suite, 3.5 bathrooms and 5 garages, 3 being attached to the house. On the first floor a large living room leads to an open concept dining room and a bright kitchen, perfect for gatherings. On the second floor, the 5 bedrooms and 3 bathrooms as well as a dedicated office space await you. A full house generator has been installed. Be the first to discover this hidden gem. Agent/co owner. Cameras are installed outside. UPDATE: Sellers are thanking all agents and potential buyers for their interest and are asking for Highest and best offers by Tuesday June 9th noon.

5 Beds ⋅ 4 Baths ⋅ 24177506 MLS

This Greenfield hill Charming colonial, sits on a 1.6 acre lot, right at the border of Fairfield and Westport and only 6 away minutes from the Southport train station and multiple beautiful beaches. Cozy and stylish with a twist of French flair, this well maintained property offers, 5 bedrooms, including a nursery right by the primary suite, 3.5 bathrooms and 5 garages, 3 being attached to the house. On the first floor a large living room leads to an open concept dining room and a bright kitchen, perfect for gatherings. On the second floor, the 5 bedrooms and 3 bathrooms as well as a dedicated office space await you. A full house generator has been installed. Be the first to discover this hidden gem. Agent/co owner. Cameras are installed outside. UPDATE: Sellers are thanking all agents and potential buyers for their interest and are asking for Highest and best offers by Tuesday June 9th noon.

1488 Sturges Hwy, Fairfield

$1,350,000

Rare opportunity to own a beautifully maintained ranch-style home on 5+ private acres in coveted Greenfield Hill. A striking balance of old and new, this breathtaking vaulted atrium-style kitchen is the architectural heart of the home, where soaring ceilings and natural light create an unforgettable sense of openness This 3 bedroom, 2.5-bath residence offers privacy, flexibility, and endless potential in one of Fairfield's most sought-after locations. Designed for comfortable living and entertaining, the open-concept floor plan features a spacious living room with hardwood floors, custom built-ins, a wood-burning fireplace, and oversized picture windows. The sun-filled-vaulted atrium style kitchen showcases dramatic floor-to-ceiling windows that capture breathtaking views. Enjoy an expansive patio overlooking rolling grounds, flowering trees, and abundant wildlife. A flexible layout offers multiple primary suite options. Main-level laundry and a powder room add convenience, while the unfinished lower level offers over 1,500 square feet of expansion potential. Recent improvements include a new septic system and radon mitigation system (2022), mini-split HVAC (2026), sump pump (2026), new water tank installation and well casing remediation (2026), propane for the kitchen stove, electrical upgrade to support a future generator. Perfect for downsizers, those seeking a peaceful country retreat, or buyers looking to expand in a premier Greenfield Hill setting.

3 Beds ⋅ 3 Baths ⋅ 24191748 MLS

Rare opportunity to own a beautifully maintained ranch-style home on 5+ private acres in coveted Greenfield Hill. A striking balance of old and new, this breathtaking vaulted atrium-style kitchen is the architectural heart of the home, where soaring ceilings and natural light create an unforgettable sense of openness This 3 bedroom, 2.5-bath residence offers privacy, flexibility, and endless potential in one of Fairfield's most sought-after locations. Designed for comfortable living and entertaining, the open-concept floor plan features a spacious living room with hardwood floors, custom built-ins, a wood-burning fireplace, and oversized picture windows. The sun-filled-vaulted atrium style kitchen showcases dramatic floor-to-ceiling windows that capture breathtaking views. Enjoy an expansive patio overlooking rolling grounds, flowering trees, and abundant wildlife. A flexible layout offers multiple primary suite options. Main-level laundry and a powder room add convenience, while the unfinished lower level offers over 1,500 square feet of expansion potential. Recent improvements include a new septic system and radon mitigation system (2022), mini-split HVAC (2026), sump pump (2026), new water tank installation and well casing remediation (2026), propane for the kitchen stove, electrical upgrade to support a future generator. Perfect for downsizers, those seeking a peaceful country retreat, or buyers looking to expand in a premier Greenfield Hill setting.

585 Hoydens Ln, Fairfield

$1,330,000

Set on a level, professionally landscaped acre in lower Greenfield Hill, this four bedroom Colonial carries the kind of care that shows with a freshly painted exterior (2024), Marvin Infinity windows, and a new roof and gutters (2025). The heavy lifting is done. What remains is the pleasure of moving in and loving life on Galloping Hill Road. The interior layout flows well, creating spaces for both intimate gatherings and larger family functions. The living room is bathed in light, anchored by an expansive wall of windows, and when the evenings turn cool, the family room awaits with a wood-burning fireplace. Look out on the flat private yard and garden area from the screened-in porch. The second level extends form and function with the primary suite offering a steam shower and quietly practical laundry chute. Three more beds with a shared bath complete the second level. Central air, irrigation, and thoughtful updates throughout create a home with classic character that still feels effortlessly current. A commuter's dream and a recreational paradise, this home is situated just 2.5 miles from Metro-North and 55 miles to Midtown Manhattan. Enjoy the ultimate coastal lifestyle with resident access to 5 local town beaches and Post Road shops and restaurants just 2.5 miles away. For nature lovers, Lake Mohegan's hiking trails and fresh water beach are also a quick 2.5 miles. Live here and love life.

4 Beds ⋅ 3 Baths ⋅ 24188915 MLS

Set on a level, professionally landscaped acre in lower Greenfield Hill, this four bedroom Colonial carries the kind of care that shows with a freshly painted exterior (2024), Marvin Infinity windows, and a new roof and gutters (2025). The heavy lifting is done. What remains is the pleasure of moving in and loving life on Galloping Hill Road. The interior layout flows well, creating spaces for both intimate gatherings and larger family functions. The living room is bathed in light, anchored by an expansive wall of windows, and when the evenings turn cool, the family room awaits with a wood-burning fireplace. Look out on the flat private yard and garden area from the screened-in porch. The second level extends form and function with the primary suite offering a steam shower and quietly practical laundry chute. Three more beds with a shared bath complete the second level. Central air, irrigation, and thoughtful updates throughout create a home with classic character that still feels effortlessly current. A commuter's dream and a recreational paradise, this home is situated just 2.5 miles from Metro-North and 55 miles to Midtown Manhattan. Enjoy the ultimate coastal lifestyle with resident access to 5 local town beaches and Post Road shops and restaurants just 2.5 miles away. For nature lovers, Lake Mohegan's hiking trails and fresh water beach are also a quick 2.5 miles. Live here and love life.

1061 Galloping Hill Rd, Fairfield

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