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2281 Redding Rd, Fairfield
$4,700,000
5 Beds ⋅ 5 Baths ⋅ 24127092 MLS
Feels like Litchfield. Lives like Fairfield. Tucked behind a private gate in Greenfield Hill, this estate offers what few properties can: sweeping space, true privacy, and serene beauty-just 60 miles from Manhattan. A long stone drive leads to the 1941 main residence, reimagined with timeless craftsmanship. Sunlight floods rooms finished with reclaimed wood beams and wide-plank floors. The chef's kitchen opens to elegant dining and living areas, with French doors to a bluestone terrace designed for candlelit dinners under the stars. A first-floor guest suite with a full bath provides flexibility and privacy, while upstairs, four additional bedrooms-including a serene primary suite-offer refined comfort and room to breathe. Beyond the home, the grounds unfold like a private resort. A two-story pool house features a full kitchen, bath, and playful loft. A climate-controlled barn houses a Trackman 4 golf simulator, sauna, and space for training or unwinding. Outdoors, discover a saltwater pool and spa, sport court, vegetable gardens, wildflower meadow with carved walking trails, orchard of apple, cherry, and peach trees, and a cider press-all with a private path leading to the Patterson Club. Whether for weekends or a lifetime, this estate elevates every season and every gathering-minutes from town, yet a world apart.

2281 Redding Rd, Fairfield
800 Verna Hill Rd, Fairfield
$4,250,000
4 Beds ⋅ 8 Baths ⋅ 24180502 MLS
Set on one of Fairfield's most coveted streets, this is the kind of home families spend years hoping will become available. Set on 3.35 acres on prestigious Verna Hill Road, adjacent to Fairfield Country Day School, this is the kind of property that becomes the backdrop for decades of memories. Summer afternoons by the pool and spa. Holiday dinners that bring everyone together. At the center of it all is a home that balances grandeur with warmth. The gracious living and dining rooms, with their soaring ceilings, were made for entertaining, while the sunroom and family room naturally become gathering places, overlooking the pool, patio, and grounds. Tucked away, a richly paneled office with fireplace and French doors opening to a private garden provides a quiet retreat. The four bedrooms are all en-suite, with the primary offering his and her baths and dressing rooms, along with the convenience of an elevator. Connected by a breezeway, the detached three-car garage is topped by a 1,000 sqft studio apartment (5th bedroom) with a kitchen, full bath, and washer and dryer-ideal for au-pair, extended family or gym. Outside, resort-style amenities include a pool, spa, expansive terraces overlooking the flat manicured backyard. Properties like this are increasingly rare: timeless architecture, one of Fairfield's most coveted addresses, all just minutes from town, beaches, and country clubs.

800 Verna Hill Rd, Fairfield
110 Queens Grant Dr, Fairfield
$4,200,000
5 Beds ⋅ 8 Baths ⋅ 24149979 MLS
*New Tax Assessment for 2026-2027 $1,949,290. In an idyllic Greenfield Hill location, this magnificently proportioned and beautifully constructed 6642 square foot Colonial enjoys a gorgeous, gated 2 Acre property, manicured and landscaped to perfection, with an expansive two-tiered Granite Terrace and stunning 20' by 40' gunite Pool overlooking sweeping lawns. Greatly contributing to the overall symmetry of this classic design, the luxurious floor plan includes five Bedrooms, six full baths, two powder rooms, (Living Room, Den, and Family Room each with Fireplace), formal Dining Room, Designer Kitchen, Summer Kitchen, stunning Primary Suite with 2 Full Baths, open Great Room on the 2nd floor, as well as versatile, finished space on the third floor. The spacious finished Lower Level (additional 1528 square feet) features a fabulous Gym with mirrored walls, Recreation area and Full Bath. Embracing a lifestyle of serenity & enjoyable entertainment, refined architectural elements and custom detailing throughout combine to further enhance this very stately and impeccable home. First Floor: 2-story Entrance Hall with herringbone wood flooring. Powder Room with tile flooring and pedestal sink. Living Room with hardwood flooring. Den beyond sharing double-sided gas Fireplace. Office with hardwood flooring, cherry cabinetry and built-ins, and ceiling fan. Summer Kitchen (with access to Pool Terrace) with porcelain tile flooring, PLEASE OPEN ADDENDUM FOR FURTHER DESCRIPTION

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

129 Quarter Horse Ln, Fairfield
1084 Sturges Hwy, Fairfield
$3,800,000
6 Beds ⋅ 9 Baths ⋅ 24114747 MLS
Luxury Living on the Fairfield/Westport Border. "Sturges Manor" is an exceptional 6-bedroom, 8-bath estate that offers a rare combination of privacy, elegance, and resort-style amenities - just minutes from the Post Road and 50 miles from NYC. Enjoy multiple town centers and restaurants. The house features expansive, sun-filled interiors ideal for everyday living and entertaining. Recently refreshed with new paint and carpeting, the home includes a formal living and dining room, a large eat-in kitchen, and generously sized family spaces throughout. The finished lower level is designed for wellness and fun, with a 6-person sauna, steam shower, and a spacious game/media room. A third-floor flex space offers the perfect spot for a yoga studio, home office, or quiet retreat. The outdoor experience is equally impressive: a heated saltwater pool and spa, tranquil ponds, a cascading waterfall, and lush manicured lawns set the tone for relaxed luxury. Entertain with ease using the fully equipped outdoor kitchen and fire pit, or shoot hoops on your basketball court. Additional highlights include a full gym, wine cellar, elevator servicing all levels, and two separate 3-car garages-ideal for collectors. A pre-paid landscaping contract through 2031 ensures the grounds remain pristine year-round. Close proximity to some the CT's best private and public schools. This is an extraordinary opportunity to enjoy the best of Fairfield County in a setting that feels like a private resort

1084 Sturges Hwy, Fairfield
475 Fence Row Dr, Fairfield
$3,425,000
4 Beds ⋅ 8 Baths ⋅ 24200803 MLS
Set well back from the road on two acres in Greenfield Hill, this remarkable residence is approached by a tree-lined drive of pavers, cobblestone and Belgian block. Completely rebuilt and reimagined with the quality and craftsmanship of new construction, nearly 8,000 square feet unfold across three levels with four bedrooms, six full and two half baths, wide-plank oak floors, expansive windows and tranquil pond views. A sun-filled atrium with soaring 20-foot ceilings introduces gracious living and entertaining spaces accented by multiple fireplaces. The tremendous chef's kitchen features quartzite surfaces, abundant cabinetry, a walk-in pantry and Sub-Zero, Wolf and Miele appliances, including dual refrigeration, ovens and dishwashers. The primary suite features a barrel-vaulted ceiling, fireplace and separate his-and-hers areas, each with a walk-in closet and private marble bath with heated floors. Two additional en suite bedrooms and laundry complete the upper level. The light-filled walkout lower level includes a fireplace, kitchenette, wine room, full bath, exercise room, second laundry and flexible recreation/media space. Terraces with a fire pit and built-in grill overlook the peaceful grounds. Smart-home technology, a generator, all-new systems and a standing-seam metal roof add turnkey ease. The Ridge offers a staffed gated entrance, private roads, mature trees, clubhouse, heated pool, tennis and pickleball.

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

145 Galloping Hill Rd, Fairfield
99 Old Academy Rd, Fairfield
$3,292,000
6 Beds ⋅ 8 Baths ⋅ 24130154 MLS
Welcome to 99 Old Academy Road, a distinguished Cape originally reimagined by local architect Richard Swann and thoughtfully expanded in 2019 by Alex Esposito. Arched-top dormers elevate the architecture, blending tradition with luxury. This residence offers 6 bedrooms plus a private two-level guest suite, 7 full / 3 half baths, all set on 2+ acres in lower Greenfield Hill. At the heart of the home, the kitchen offers an open layout with a spacious dining area, custom cabinetry, a floor-to-ceiling glass wine display, and walk-in pantry. The kitchen flows seamlessly onto a bluestone patio with a double-sided fireplace, perfect for indoor-outdoor living. The kitchen leads to the lower level, featuring a stone bar in the game room, a 10-seat cinema, and ample storage. The family room, with its built-ins, poolside views, and gas fireplace, offers an inviting year-round retreat, the main level also includes a private office. Upstairs, every bedroom is paired with its own private bath, each with a unique design. The custom mahogany library serves as a passage to the East Wing, where the main level offers a gym, poolside lounge, & outdoor shower, while the upper-level features three additional en-suite bedrooms and a second laundry room. Outdoors, enjoy wrap-a-round mahogany decks, multiple bluestone patios, a heated pool, volleyball court, pergola gardens, and fruit trees. 99 Old Academy Road isn't just a home, it's a lifestyle of elegance, comfort, and unforgettable spaces.

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

2683 Bronson Rd, Fairfield
111 Golden Pond Ln, Fairfield
$3,000,000
5 Beds ⋅ 8 Baths ⋅ 24175561 MLS
111 Golden Pond Lane is the rare luxury home that feels as welcoming as it is impressive. Tucked at the end of a quiet, tree-lined cul-de-sac, the home opens with an undeniable scale - soaring 19-foot ceilings, a dramatic two-story entry, sweeping staircases, and natural light that moves effortlessly throughout the day. Yet what makes the home memorable is not its grandeur alone, but the warmth and ease with which it lives. Over the past six years, the residence has been completely transformed by its current owner and designer, blending refined architecture with interiors that feel both elevated and deeply comfortable. At the center of the home, the vaulted family room with stone fireplace and whitewashed beams creates a true gathering space - equally suited for large celebrations or quiet evenings at home. The south-facing kitchen is filled with sunlight and custom detail, designed not simply to impress, but to be used and enjoyed every day. Rarely found, the home offers luxurious primary suite options on both the main and second levels, creating remarkable flexibility for guests, multigenerational living, or evolving needs over time. Outside, an oversized patio overlooks mature trees and complete privacy, with ample room for a future pool and sport court. Peaceful and secluded, yet just seven minutes to Metro-North, the property offers a lifestyle that feels worlds away from the city without sacrificing convenience. Grand in scale. Warm in spirit.

111 Golden Pond Ln, Fairfield
1380 Old Academy Rd, Fairfield
$3,000,000
4 Beds ⋅ 6 Baths ⋅ 24153510 MLS
THANK YOU FOR YOUR STRONG INTEREST; SELLER REQUESTS HIGHEST & BEST OFFERS BY 4PM SAT 2/28 . One approaches 1380 Old Academy Road through a stone wall, where a paved drive opens to a gravel courtyard arrival framed by mature trees and open skies. Old Academy is the kind of street where homes feel settled rather than transitional, and where people arrive, put down roots, and tend to stay. Inside, the house is generous without feeling oversized. Tall ceilings, dormers, and bay windows draw natural light deep into the living spaces, allowing it to move easily throughout the day. The main living areas are grounded by multiple fireplaces, and the layout supports everyday living with ease while expanding naturally when the house is full. The finished lower level adds meaningful flexibility, with room for fitness, media, or wine storage. A cabana-style mudroom with a full bath and direct outdoor access extends the way the home lives across seasons. Upstairs, the bedrooms are designed with privacy in mind, offering thoughtful connections that work well for both family and guests. Outdoors, the property becomes a destination in its own right. A Gunite pool bordered by stone terraces, an outdoor fireplace, a putting green, and a side porch with rocking chairs create spaces meant for lingering rather than passing through. Manicured grounds, full irrigation, and a three-car garage complete the setting. Carefully maintained and continually improved, this is Greenfield Hill livi

1380 Old Academy Rd, Fairfield
40 Hill Brook Ln, Fairfield
$2,995,000
4 Beds ⋅ 5 Baths ⋅ 24172448 MLS
The David Hill Home, Circa 1749. There's a certain kind of house that stops you the moment you pull up. Not because it's trying to impress you - but because the history speaks for itself. Wide plank floors worn smooth by centuries of foot traffic, five original fireplaces, hand-hewn beams - the kind of quiet character newer construction simply can't manufacture. The life inside has been carefully reimagined though. Walls opened, rooms connected, spaces rethought. The chef's kitchen features quartzite countertops and a GE Smart Monogram range. The primary suite is a genuine retreat - radiant marble floors, double vanities, steam shower. Lucifer lighting throughout sets the mood in every room. A sun-drenched bonus room shifts with the seasons - office, sunroom, art studio - whatever the day calls for. The infrastructure has been upgraded too. Full house generator, new Trane HVAC, new smart pool heater and a whole-house water shutoff mean the things you never want to think about are already handled. Outside, the acres unfold into something genuinely private - a pool and spa, pool house, and a barn that's been there longer than almost anything else around it. Lower Greenfield Hill puts you close to everything without feeling like it. Restaurants, shops, top schools, and both Fairfield and Southport train stations all nearby. Some homes you tour. This one you remember.

40 Hill Brook Ln, Fairfield
171 Paddock Hill Ln, Fairfield
$2,950,000
4 Beds ⋅ 6 Baths ⋅ 24180342 MLS
Timeless craftsmanship, extraordinary scale & a level of construction quality increasingly difficult to find define this exceptional estate located in Fairfield's only gated community. Set on over 2 professionally landscaped acres on the Fairfield/Westport border, this home showcases generous room proportions, architectural detail & custom millwork seldom seen. A dramatic double-height foyer introduces over 5,000 sq ft of thoughtfully designed living space. The newly renovated chef's kitchen showcases a quartz waterfall island, full-height quartz backsplash, 2 oversized walk-in pantries, stunning breakfast area & a beautifully appointed wet bar w/beverage refrigerator & sink. The main level also offers a gracious living room w/gas fireplace, spectacular step-down family room w/soaring ceilings & wood-burning fireplace, formal dining room, richly paneled office w/custom built-ins, 2 powder rooms, & an elevator servicing 3 levels. A sweeping staircase leads to the 2nd level where the primary suite offers vaulted ceilings, 2 walk-in closets & a beautifully appointed spa-inspired bath. 3 additional generously sized bedrooms offer comfortable accommodations for family & guests. The finished lower level offers a recreation room w/fireplace, 5th bedroom, full bath, & abundant storage. Outside, 2 bluestone patios create distinct spaces for dining, entertaining & gathering around a built-in gas fireplace all set w/in expansive lawns & exceptional privacy. A rare offering in The Ridge.

171 Paddock Hill Ln, Fairfield
21 Queens Grant Dr, Fairfield
$2,880,000
6 Beds ⋅ 8 Baths ⋅ 24123339 MLS
There are houses you tour, and then there are estates that capture your imagination. This extraordinary Greenfield Hill Colonial is the latter-a 9,700+ sq. ft. residence set on a pristine 2-acre corner lot in one of Fairfield's most prestigious neighborhoods. A paver-stone drive winds past manicured gardens to a grand two-story entry with a sweeping staircase, setting the tone for elegant living. Meticulously landscaped grounds, fountain, serene stone pathways, and a tranquil koi pond create a private oasis for quiet reflection or outdoor enjoyment. Inside, elegant formal living and dining rooms provide a perfect backdrop for entertaining, while the sun-filled family room, with vaulted ceilings, floor-to-ceiling windows, and a dramatic stone fireplace, serves as the heart of the home. The luxurious primary suite boasts tray ceilings, dual walk-ins, and a marble spa bath. Upstairs, five spacious bedrooms-many ensuite-welcome guests, and the third floor features a game and billiards lounge. A bespoke English pub, thoughtfully designed and versatile, can serve as a lounge, home office, entertainment room, or hobby space. Outdoors, a gated saltwater pool and hot tub with a fully equipped poolhouse create an inviting retreat for summer gatherings. This remarkable estate blends sophistication, comfort, and timeless appeal-a sanctuary for grand occasions and quiet moments alike.

21 Queens Grant Dr, Fairfield
750 Burr St, Fairfield
$2,850,000
6 Beds ⋅ 8 Baths ⋅ 24170071 MLS
No need to journey to the South of France...this extraordinary estate brings European romance & luxury to coveted Fairfield, CT. Beyond grand gates lies a private world where beauty, security, & serenity exist in perfect harmony. Magazine-worthy grounds define the estate, featuring a gorgeous pool, spectacular CA Redwood Pool House w/ full kitchen, covered entertaining spaces, mature gardens, bluestone terraces, & sweeping lawns...creating a setting that feels like a private resort. Inside, the open-concept design centers on a chef's kitchen that flows seamlessly into a breathtaking Great Room with soaring ceilings & a dramatic stone fireplace. Elegant formal living and dining rooms, a sun-filled family room with fireplace, and a remarkable home office w/ fplc offer both sophistication and comfort. The main residence offers 4-5 bedrooms, including a magnificent Primary Suite with sitting areas, private balcony, custom closets, and a spa-inspired bath w/ romantic fireplace. A separate first-floor wing with lounge and additional bedrooms provides ideal flexibility for family, in-laws or guests. A charming guest cottage, private suite above the carriage house, and a storybook artist's studio or gym complete this exceptional compound. Ideally positioned for today's lifestyle, Lions Gate offers the rare balance of peaceful seclusion & everyday convenience, just minutes to train, town & beaches, with easy access to Metro NYC, yet a setting that feels like a countryside retreat.

750 Burr St, Fairfield
342 Midlock Rd, Fairfield
$2,750,000
5 Beds ⋅ 7 Baths ⋅ 24134949 MLS
Welcome to an unrivaled sanctuary of sophistication at 342 Midlock Road, gracefully situated in the prestigious enclave of Greenfield Hill. This stately residence, perched on a coveted cul-de-sac off Burr Street, unfurls over two lush acres of meticulously manicured, fully fenced grounds. Upon entry, be enveloped in luxury as you traverse through spaces adorned with custom millwork, nine ft ceilings, abundant natural light and more. The heart of this home is an eat-in chef's kitchen, replete with top-tier stainless steel appliances, which connects you to multiple other spaces for enjoyment or repose. Entertain with panache in the formal dining room, garden room, library, living room or great room. Five fireplaces spread across this generous layout hosting five bedrooms- all ensuite- plus additional oversized office/media room with kitchenette, as well as third floor rec room with attached full bath and access to boutique-style cedar closet. Outdoors, a resplendent oasis awaits, featuring a pristine gunite with pebble sheen pool, granite heat resistant patio and an exquisite pool house with kitchenette and full bath, and expansive stone outdoor kitchen- a sublime setting for al fresco gatherings. A lifestyle of unparalleled elegance and comfort is a given. Every detail of this meticulously maintained home harmonizes to create an estate that epitomizes refined living. This majestic manor reflects pride in ownership and a timelessness that commands to be experienced.

342 Midlock Rd, Fairfield
2821 Congress St, Fairfield
$2,700,000
5 Beds ⋅ 5 Baths ⋅ 24111053 MLS
Located in the heart of Greenfield Hill, "Upper Meadow Farm" is a rare blend of timeless character and modern comfort. Originally dating back to 1835, this storied property at 2821 Congress Street has been thoughtfully expanded and updated over the years, most recently in 2019 by the current owners. The result is a warm, welcoming home where historic details meet a fresh, refined palette. A spacious first-floor primary suite offers privacy and stunning southern views across the property, complete with a fireplace, office, and walk-in closet. The main living areas are gracious yet inviting, ideal for everyday living or hosting guests. Upstairs are four additional bedrooms and three full baths, one currently used as a home office. Step outside and discover the true magic of the property: a beautifully reimagined former blacksmith's barn with a loft, full bath, and bar area-perfect as a guest house, studio, or entertainment space. The pool, added in 2015, is complemented by a stylish pool house featuring a kitchenette, full bath, and generous terracing for summer evenings under the stars. Set on picturesque grounds, this is an exceptional opportunity for those seeking a full-time residence or a weekend retreat in one of Fairfield's most beloved neighborhoods. A truly special home.

2821 Congress St, Fairfield
73 Foggwood Cir, Fairfield
$2,650,000
5 Beds ⋅ 6 Baths ⋅ 24188324 MLS
Spectacular custom estate built by Andy Frank in prestigious Greenfield Hill featuring a rare first-floor primary suite w/fireplace, spacious WIC, luxurious spa bath & vaulted ceiling -- a true standout for convenient main-level living. Set on over 2 magnificent landscaped acres on a double cul-de-sac, this home delivers resort-style living w/exceptional privacy. Outside, an oversized free-form gunite pool w/waterfall anchors spectacular entertaining & relaxing areas, complemented by stone walls, a large stone patio, and lovely deck - and enhanced by beautiful mature plantings & deer fencing. Inside, a dramatic double-height foyer w/marble floor leads into a custom EIK with quartz countertops, an oversized island & pantry that opens seamlessly to the lovely family/living room & idyllic backyard. Another larger family room features a custom bar, pool table, built-ins, and a half bath. Three fireplaces, a first-floor library/office, custom laundry room & two staircases complete the first floor. Upstairs, the second floor offers four large bedrooms & two beautifully full baths. The finished walk-out LLevel is an entertainer's dream, complete w/custom wine cellar, full bath, wet bar, multiple entertaining zones, storage rooms & gym space. Exquisite millwork & detail throughout. This private, spacious setting is a short drive to the train for NY commuters, & to vibrant shops, restaurants & the energy of downtown Fairfield & Westport. Natural gas completes this special property.

73 Foggwood Cir, Fairfield
200 Long Meadow Rd, Fairfield
$2,500,000
4 Beds ⋅ 3 Baths ⋅ 24147180 MLS
Located in the coveted Greenfield Hill neighborhood, this exceptional property offers the perfect blend of weekend retreat and everyday living, just 60 miles from Manhattan. Set on over 2 private acres with classic stone walls, cedar roof, copper gutters and professional landscaping, the home welcomes you with a dramatic two-story foyer and 9-foot ceilings throughout. The designer living room flows seamlessly into a gorgeous dining room with custom paneling and continues through a gallery-style hallway to the stunning gourmet kitchen, featuring Sub-Zero refrigeration, Wolf gas cooktop, wall oven, pantry, and high-end finishes. Just off the kitchen is a charming shiplap mudroom with direct access to the garage. The kitchen opens to a cozy family room accented with newly added wood beams and fireplace. French door sliders lead to the backyard, creating an effortless indoor-outdoor connection. The second floor features a serene primary suite with a spacious walk-in closet and a spa-like bathroom offering a double vanity and oversized shower and . Additional spacious bedrooms share an impressive oversized full bath, and a dedicated laundry room completes the level. The above-ground finished lower level provides flexible living space, ideal for a home gym or additional entertaining area. Outdoors, the property truly shines with a gunite pool surrounded by bluestone, above-ground boxed gardens, and a level lawn space perfect for entertaining, recreation, or quiet relaxation,

200 Long Meadow Rd, Fairfield
3050 Bronson Rd, Fairfield
$2,495,000
4 Beds ⋅ 4 Baths ⋅ 24186223 MLS
A Connecticut Classic - this center hall Colonial is located on the most charming stretch in Greenfield Hill. Beautifully set on 2 acres, this 4 bedroom Jack Franzen designed home lives large in all aspects. Guests are welcomed into the double height foyer flanked by formal living and dining rooms. The great room spans the back of the house combining a gorgeous light, bright & well appointed kitchen, with a cozy family room w/ traditional fireplace & plenty of room for gathering & lounging, a dining area and a cozy window seat - and easy access to the huge recreation room set over the garage! The first floor also holds a lovely library room with another fireplace, beautiful, oversized windows facing both front and back views and custom built-ins. Upstairs, the primary bedroom is spacious and light-filled, with a recently renovated bath and walk in closet. There is an ensuite bedroom plus two additional bedrooms sharing a hall bath. Outdoor living is maximized with two deck spaces and a pretty patio, perfect for entertaining, grilling and enjoying the privacy of the gorgeous, fenced in grounds! True New England character is felt throughout, from the rich hardwoods, charming wainscotting & coastal chic kitchen to the historical neighborhood setting - imagine spring days on the green celebrating the Dogwood Festival, sounds of baseball being played at the nearby diamond all while also being centrally located to all Fairfield amenities like beach, town and train to NYC!

3050 Bronson Rd, Fairfield
2775 North St, Fairfield
$2,350,000
5 Beds ⋅ 8 Baths ⋅ 24128629 MLS
Crafted by noted custom builder Garrett Wilson and meticulously enhanced with recent upgrades, this Greenfield Hill home is as impressive as it is inviting. Finished to the highest standard, the residence is set on just over two private acres with a tennis court and expansive open space offering room for a pool and pool house. At the heart of the home, the chef's kitchen is filled with natural light and outfitted with Wolf and Sub-Zero appliances, two farmhouse sinks, two dishwashers, two wine refrigerators and a beautifully refinished wood island. Upstairs, you will find 5 bedrooms, all en-suite with walk-in closets and a spacious laundry room. The primary suite provides a serene retreat with his and hers walk-in closets and a spa bath with steam shower. The finished top level is ideal for an in-law or au pair suite with full bath and sweeping property views. The lower level offers a warm entertaining space with fireplace, a home gym, an additional flex room to be used as a playroom, bedroom or office, and an additional laundry room and full bathroom. Deer fencing encircles the entire property, with a gated entrance for enhanced security and privacy. Enjoy the ease of town water and natural gas utilities. Other recent updates include a new roof, new HVAC system and boiler with expansion tank. The property is convenient to Fairfield and Westport town centers and is commuter friendly to Manhattan. Truly a remarkable offering in sought-after Greenfield Hill.

2775 North St, Fairfield
165 Hemlock Hills Rd S, Fairfield
$2,335,000
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
66 Gate Stone Ln, Fairfield
$2,256,600
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
158 Coventry Ln, Fairfield
$2,225,000
4 Beds ⋅ 4 Baths ⋅ 24151483 MLS
Step into the epitome of elegance & comfort at 158 Coventry Lane, a stunning Connecticut Colonial located in the prestigious Greenfield Hill area of Fairfield. Beautifully sited on a vibrant cul-de-sac, this turn-key home offers an unparalleled lifestyle in a serene, picturesque setting. Set on 2 acres of level grounds, this property is a true sanctuary w/impeccably landscape, stone walls, a bluestone patio & walkways, a heated saltwater pool & spa, enclosed vegetable garden & pool house. It's the perfect retreat for both relaxation & year-round entertainment. Inside, sophistication meets functionality. A dramatic triple-height foyer w/herringbone floors greets you, setting the tone for the 4,244 sq feet of updated living spaces. The layout is designed for both large gatherings & everyday comfort. The family rm, with its vaulted ceiling & floor-to-ceiling fieldstone fireplace, flows seamlessly into a private den/media room complete with a wet bar. The elegant living rm, featuring a beautiful gas fireplace, opens to a versatile office, playroom or guest suite w/an adjacent full bath. The heart of the home is a sleek modern kitchen, boasting a 9-foot quartz island, wine fridge & panoramic views of the backyard oasis. Upstairs, the primary suite is a private retreat w/a dramatic fireplace & spa-like bath. 3/4 addt'l bedrooms, and a private home office ensure space for every need. Only 8 mins to downtown Fairfield train station, shopping and dining.

158 Coventry Ln, Fairfield
677 Eleven O Clock Rd, Fairfield
$2,220,000
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
820 Hillside Rd, Fairfield
$2,215,000
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
2444 Bronson Rd, Fairfield
$2,125,000
4 Beds ⋅ 4 Baths ⋅ 24189160 MLS
Classic charm on beautiful Bronson Road! A customized Colonial that overflows with extras - 4/5 bedrooms, open living spaces, play rooms, office/work zones, preserved historical touches and outdoor living options for all occasions! The main floor lives large. A formal living room, dining room, and sun room are on one side. While a huge front to back great room consisting of the kitchen, family room, play room, and the mudroom connection (complete with a built-in window seat) spans the other side. The breakfast bar has seating for 6, there is a dining area with full wet bar, a big stone fireplace with tons of room for gathering and lounging, plus access to the decks and patio beyond! Upstairs the primary suite is light and bright with vaulted ceilings, an oversized bath and a balcony. There are three generously sized bedrooms and a hall bath completing the second floor. On the lower level, walls of windows keep the rec room bright and sunny with tons of room to customize and the easy access to the outdoors is a bonus! At just under an acre, the property includes rolling lawns and plenty of privacy to enjoy all the space. There is a 2 car garage, and the central proximity to town, train schools and beaches is perfection!

2444 Bronson Rd, Fairfield
2477 Bronson Rd, Fairfield
$2,100,000
3 Beds ⋅ 3 Baths ⋅ 24191574 MLS
Nestled in the heart of historic Greenfield Hill, this special and timeless 1907 Queen Anne farmhouse provides an opportunity to own in one of the most desirable and coveted locations in Fairfield. The Clifford S. Banks house was once a farm where the owner raised turkeys, chickens, onions and bees. Situated on 2 acres of beautifully landscaped grounds that includes gardens and a barn- perfect for the equestrian family. This historic home has been thoughtfully expanded and restored over the last 40 years by the owners to maintain the old-world craftsmanship and provide modern comforts. As you approach the front entrance, you will be surrounded by an inviting screened porch and covered porches. A welcoming entry leads you to the inviting LR w/ expansive windows and wood burning fireplace, formal DR and FR w/ walls of built ins. The kitchen has been expanded to create a dining area w/ custom banquette seating and surrounded by windows providing an abundance of natural light. The kitchen was designed for a cook w/ attention to detail, design and function. The laundry room w/ ample storage and a Powder room complete the main level. The upper level has an inviting "sun parlor" which provides a cozy sitting area and office space. The primary bedroom features a comfortable retreat w/ walk-in closet and updated bath. There are 2 additional BRS and a hall bath. The spacious 3rd floor w/ architectural details and beams provide endless possibilities and storage. Full house generator.

2477 Bronson Rd, Fairfield
545 Shrub Oak Ln, Fairfield
$2,100,000
5 Beds ⋅ 4 Baths ⋅ 24115368 MLS
Welcome to 545 Shrub Oak Lane, an expanded Colonial on 2 private acres in Greenfield Hill. This home sits on a beautifully flat front yard that enhances its curb appeal. Fully renovated in 2012, the family room and oversized kitchen is the heart of the home. The custom designed kitchen has an 10 foot mahogany island with granite countertops, walk-in panty, and mahogany wood framed glass doors that create a seamlessly indoor-outdoor experience. The first level offers a formal living and dining room, an office and an expanded mudroom. Upstairs, the primary suite includes french doors to a private deck, a steam shower, a jacuzzi tub, walk-in closet, and a separate sitting room. Four additional bedrooms, two baths, and laundry room complete the upper level. The lower level offers a rec room, extra laundry, an office and ample storage. The oversized three-car garage with unfinished bonus space above is ideal for a in-law suite or future expansion. Outside is an entertainer's paradise, a custom designed lagoon-style pool with diving rocks, multiple bluestone patios, an elevated covered patio, two mahogany decks and an incredible recreational setup, including a full-size lighted basketball court, a turf area for bocce ball/batting cage, fire pit and more!

545 Shrub Oak Ln, Fairfield
1680 Cross Hwy, Fairfield
$2,050,000
5 Beds ⋅ 6 Baths ⋅ 24188539 MLS
1680 Cross Highway is a nod to all of the pristine, old-school colonials in leafy Greenfield Hill, however, its interiors and landscape have been beautifully updated to reflect the needs of the current owners, a modern family of four, with a nanny and friends continuously coming and going. The chef's kitchen was masterfully streamlined with new GE Monogram appliances, an oversized center island, and incredible storage capability. The flow continues into an open dining room on one side, a spacious family room on the other, with a wood burning fireplace and easy access to a screened-in porch, Trex deck and hot tub. A formal living room with a fireplace often kicks off the evening, inviting outdoor relaxation on the side deck, with views of the private yard and vegetable gardens. A corner library with custom bookcases, mudroom, laundry, and half bath complete the first floor. Upstairs, the primary suite was updated to provide a spa-like, oversized bathroom and additional walk-in closet space. There are three additional well-proportioned bedrooms and bathrooms. The basement has been reworked too, mostly to accommodate visitors and add a finished 1215 sq ft of living space: rec-room with built-ins, kitchenette/breakfast bar, a bedroom, full bath and gym space. Convenience is king here too with a convenient location for commuting, shopping, school drop-off, and sporting events. The outdoor spaces are sublime, and capture the relaxed and connected spirit of the current owners.

1680 Cross Hwy, Fairfield

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