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$1,450,000
4 Beds ⋅ 3 Baths ⋅ COMING SOON Status ⋅ 24205655 MLS
Set on 2.46 picturesque acres in coveted Greenfield Hill, this modernized farmhouse Colonial combines classic character, thoughtful updates and an exceptional piece of property. Beautiful stone walls frame expansive open lawns, while a newer front porch with copper roofing adds to the home's timeless farmhouse appeal. Just under 3,000 SF of above-grade living space features hardwood floors, detailed millwork, multiple fireplaces and a wonderfully flexible floor plan. The remodeled kitchen is the heart of the home w/ quartz counters, large center island, custom cabinetry and a high-end appliance package including Sub-Zero & Wolf. An adjacent wet bar with wine refrigeration is ideal for entertaining. The kitchen opens to a spacious living area anchored by a dramatic fieldstone fireplace. A formal dining room w/ fireplace and separate family room with vaulted ceiling and exposed beams. A standout feature is the main-level in-law potential: private entrance, bedroom, bonus room / access to a full bath-ideal for guests or an au pair. Upstairs are the spacious primary bedroom, 2 additional bedrooms and full bath. Outside, a stone patio & covered porch overlook the home's incredible grounds. Broad, field-like lawns, mature trees and extensive stonework create a true estate setting-a remarkable property to enjoy for decades to come. New roof / gutters in '26. A special Greenfield Hill home combining modern updates, versatile living space and a property that is truly unforgettable!

1835 Cross Hwy, Fairfield
$1,495,000
5 Beds ⋅ 4 Baths ⋅ COMING SOON Status ⋅ 24205061 MLS
Quintessential New England architecture, extraordinary grounds & an interior that continually surprises define this distinctive Greenfield Hill property. Privately set behind a stone wall on 2 exquisitely landscaped acres, this stately clapboard Colonial is beautifully sited w/cedar roof, cupola, rows of boxwood, bluestone walk & gracious front porch. Inside beautifully appointed rooms unfold w/remarkable versatility, warmth & exceptional flow for entertaining. Gracious living room w/gas fireplace leads to inviting dining room while the sun-filled kitchen overlooks the spectacular landscape & opens through French doors for seamless indoor/outdoor living. Family room w/custom built-ins, window seat & 2nd gas fireplace. Large laundry room & attached 2-car garage complete main level. Upstairs, 5 BR & 3 full BA include a gorgeous en-suite primary. Finished lower level is truly unforgettable: custom Irish Pub inspired by owners' travels to Ireland w/full bar, kegerator, handcrafted details & cozy wood-burning fireplace, creating a one-of-a-kind space for gathering. Outside dine beneath the cedar pergola draped in climbing hydrangea, wander through the English gardens, tend the enclosed vegetable garden, relax in the hot tub, enjoy morning coffee on the garden swing or simply watch nature unfold. Expansive bluestone patios, specimen plantings, mature trees & lush lawns create a setting that feels worlds away. A rare property where beauty, personality & inspired living converge.

3901 Redding Rd, Fairfield
$3,495,000
4 Beds ⋅ 8 Baths ⋅ ACTIVE Status ⋅ 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
$2,549,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24205159 MLS
Gorgeous Farmhouse Colonial tucked away on 2+ picturesque acres & minutes to Fairfield & Westport center. Timeless natural beauty, distinctive architecture, exquisite craftsmanship & sophisticated updates combine to create a home that truly stands apart. Featuring 12 rooms flooded w/ brilliant light over 3 levels of living. Enjoy views of a serene fallow field, a gentle stream, wildlife & stunning seasonal changes from vibrant autumn colors to peaceful snow-covered landscapes. The living room fireplace provides a cozy focal point w/ oversize French doors that open to the patio creating an ideal setting for outdoor dining & hosting. The eat-in kitchen offers the dining area, island, pantry & state of the art appliances & guides you to the dining room, office, living room & study. Upstairs the beauty continues w/ 4 large bedrooms including the primary. The lower level expands the living space w/ a new mudroom, rec room, gym & half bath. Updates include a new lower level, flagstone patio, custom pantry w/ wine storage, upgraded laundry room w/ new washer, new window in en-suite & new Rubbermaid track system. Step outside to your patio featuring a built-in Weber BBQ & XL Big Green Egg, perfect for cooking enthusiasts. Exterior has been meticulously maintained w/ repainting, stone-accented walls, Belgium block-lined driveways & ongoing landscaping. A NE bridge adds character. The Patterson Club is a bike ride away. 3007 Redding Road is filled w/ light, space & lasting memories.

3007 Redding Rd, Fairfield
$1,200,000
4 Beds ⋅ 3 Baths ⋅ COMING SOON Status ⋅ 24202615 MLS
GREENFIELD HILL COLONIAL - Set in a beautiful Greenfield Hill location, this classic Colonial offers an exceptional blend of privacy, space, and convenience. Nestled on a picturesque 2.09-acre property framed by mature trees, stone walls and sweeping lawns, this 2,588-square-foot home features four bedrooms, two-and-one-half baths, and a very well designed floor plan. A welcoming foyer opens to a sun-filled, front-to-back living room with fireplace and an elegant formal dining room. The inviting family room, also featuring a fireplace, connects to the attached two-car garage and flows seamlessly to a wonderful screened porch-an idyllic spot for morning coffee, al fresco dinners, or quiet relaxation. At the heart of the home, the spacious chef's kitchen provides ample room for gathering with family and friends. The expansive property provides exceptional privacy and a lovely backdrop for enjoying the best of Greenfield Hill. While the setting feels enchantingly secluded, the location is just minutes from Fairfield Center, the Arts & Cultural District, outstanding restaurants, boutique shopping, beautiful beaches, and Metro-North service to New York City. First Floor: Covered Breezeway. Foyer with slate flooring, guest closet, and Powder Room - provides access to all principal rooms. Front to back Living Room with hardwood flooring, and wood-burning fireplace. Elegant Formal Dining Room with hardwood flooring, and Bay Window. PLEASE OPEN ADDENDUM FOR FURTHER DESRIPTION.

2730 Burr St, Fairfield
$1,395,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 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
$7,500
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24204484 MLS
Welcome to this newly renovated home located in the heart of Greenfield Hill. Every square inch of this property has been masterfully updated with a focus on modern luxury and flawless craftmanship. The main level welcomes you with bright, airy living spaces, and gleaming refinished hardwood floors. A brand new kitchen, appliances, cabinetry, and quartz countertops, with access to the new raised deck overlooking CT Audubon open space. Upstairs, is a new primary suite with a fully updated bath and ample closet space, along with 3 spacious bedrooms and laundry room. Finished lower level with 3 additional rooms. The home has brand-new exterior siding, roof, windows, mechanicals, including heating and cooling. Don't miss this opportunity!

4672 Congress St, Fairfield
$1,800,000
5 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24184245 MLS
Nestled at the end of a peaceful cul-de-sac, in the highly sought-after Greenfield Hill neighborhood, 220 Stonewall Lane offers a rare opportunity to own a beautifully situated home on 2.07 acres. The expansive outdoor setting provides an inviting space perfect for entertaining or relaxing while enjoying the tranquil surroundings. When entering the thoughtfully planned main level, you are drawn to the large open space with a renovated modern eat-in kitchen, a sitting area with a wood-burning pizza oven, a Great Room with cathedral ceilings, a wood-burning fireplace, and an additional family room with views of the in-ground pool and lush landscaped grounds. Natural light flows throughout. Additional highlights include hardwood floors throughout, large decorative tiles, a formal living room with fireplace, a dining room, walk-up bonus room, laundry and access to the two-car garage. Upstairs, five well-appointed bedrooms include a private primary suite, creating a comfortable and functional area. The unfinished basement offers ample space for utilities, storage and possible recreational activities. Ideally located near Fairfield's beaches, Metro-North, recognized restaurants, and the Fairfield Theatre Company, this private property blends lifestyle, location, and appeal in one of Fairfield's most desirable areas.

220 Stonewall Ln, Fairfield
$3,399,900
5 Beds ⋅ 8 Baths ⋅ ACTIVE Status ⋅ 24194239 MLS
Old-world craftsmanship meets modern indulgence. Set on a peaceful, tree-lined street,this home offers total privacy and timeless curb appeal. Soaring ceilings, hand-finished millwork, and custom detail are evident throughout. This grand 5BR/6.5BA light filled residence pairs classic entertaining spaces - formal LR, formal DR, & a wood-paneled library w/wet bar & full BA-with modern amenities such as a two-story FR w/ stone FP, a stunning windowed sunroom overlooking the beautiful grounds,& an impressive chef's kitchen boasting custom appliances, double sub zero, island, & dual butler's pantries.Thoughtful proportions create a seamless flow, a home as comfortable day-to-day as it is for grand-scale entertaining.The opulent primary suite is a spa retreat onto itself, w/ dual baths, dual walk-in closets,& a private sauna.The second floor offers 3 add'l en-suite BRs w/ built-ins and large closets. The third floor offers a great room w/ custom built-ins, plus an additional BR and full BA . The lower level feat a recently upgraded state-of-the-art movie theater, gym, game room, & workshop for a serious hobbyist. The expansive, landscaped grounds offer true serenity, w/ English gardens framing a resort-caliber pool and spa in a backyard built for entertaining. Timeless elegance, tucked within The Ridge - a gated enclave w/ a staffed gatehouse, clubhouse, pool & tennis courts just minutes to Fairfield and Westport amenities. Truly a special offering w/ultimate privacy& convenience.

344 Fence Row Dr, Fairfield
$2,499,000
5 Beds ⋅ 7 Baths ⋅ ACTIVE Status ⋅ 24190034 MLS
Welcome to 3080 Sturges - Fully Renovated Home set on 2.44 private acres in Fairfield's Greenfield Hill enclave on the Westport border. Offering a Westport mailing address together with Fairfield's acclaimed schools and amenities, this 7,317-square-foot modern residence blends architectural scale with contemporary comfort and luxury. A dramatic two-story foyer introduces interiors defined by soaring ceilings, skylights, and oak hardwood floors throughout the home. Just off the foyer, a screened porch offers a peaceful setting for indoor-outdoor living and entertaining. Designed for both everyday living and entertaining, the main living spaces center around a gourmet eat-in kitchen appointed with Sub-Zero refrigeration, a Wolf range, Wolf double ovens, Wolf built-in microwave, Miele dishwasher, Marvel undercounter ice machine, quartz countertops, and a gas fireplace. Complementing the kitchen is a walk-in pantry featuring a second full refrigerator, wine refrigerator, and custom cabinetry for exceptional storage and organization. Adjacent to the kitchen, the formal dining room features custom built-in cabinetry and ample space for entertaining. Additional highlights include a grand living room with dramatic cathedral ceilings, expansive skylights, and exceptional scale, flowing into an adjacent music room with a custom tray ceiling. The home also features a private office with fireplace, billiards lounge, fitness studio, and a second laundry room.

3080 Sturges Hwy, Fairfield
$2,850,000
5 Beds ⋅ 6 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 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
$925,000
2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24176507 MLS
This rare private inholding offers a hilltop property defined by raw beauty and seclusion. The 1930s rustic hunting cabin sits on 1.6 wooded acres at the end of a private drive, surrounded by the 186-acre Brett Woods Conservation Area. The property provides a perfect balance of mature trees, rolling hills, and 18th-century stone walls-all located just eight minutes from Main Street Westport. With trails leading directly from the back door to a secluded pond and hiking paths, it serves as an ideal weekend retreat and a convenient alternative to the Vermont or Connecticut River Valley. Located only 70 minutes from Grand Central via the Westport train station, this home offers easy access to both the Connecticut coastline and deep woods.

11 Judges Hollow Rd, Fairfield
$12,000,000
7 Beds ⋅ 10 Baths ⋅ ACTIVE Status ⋅ 24161896 MLS
This offering is for 4800 Congress St, a one of a kind estate consists of main residence on 10.92 acres, pool, barn pool house/gym, heated paddle court, and an office pavilion. Surrounded by high stone walls, a fortress of modern architecture is invisible from the street,offering seclusion with proximity to NYC. The former home of Richard Rodgers, composer of The Sound of Music, the mid-century main residence was expertly restored, and all systems upgraded and integrated. The expanded footprint incorporates 7 bedrooms and 7 full baths, all with views over the open landscaped property. Lofty ceilings and walls of glass create magical interior spaces, a perfect setting for an art collector. Separate wings radiate off the main rooms. Each space has impeccable thoughtful detail. A hidden screening room , a stunning Moroccan lounge, and a guest wing allow for A-list entertaining. The barn pool house with full kitchen, bath and pro-grade gym, and pool, make this a perfect athlete's compound. An office pavilion is set privately in a quiet garden area. The landscape offers open vistas, meadows and an orchard. Live in ultimate style and easy elegance at this private retreat a quick commute to NYC and airports.. A private haven surrounded by a 155 acre nature preserve just minutes to Westport, Greenwich, and convenient to NYC and airports.

4800 Congress St, Fairfield
$995,000
1 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24166262 MLS
CHESTNUT GROVE - Wonderful opportunity to enhance an extraordinary, sweeping 2.39 acre parcel in a beautiful and bucolic Greenfield Hill location. This expansive property nestled within a Chestnut Grove, features a stately Barn providing Garage storage suitable for farming equipment and motor vehicles, and a recently constructed second story Studio Apartment enjoying a haven of privacy and seclusion. The sun-lit Great Room presents a fully equipped Kitchen with cabinetry and Breakfast Bar, Laundry with stack washer and dryer, and a beautifully tiled full bath with shower. Currently taxed under Farm Status. NEW ASSESSMENT FOR TAX YEAR 2026 - 2027 IS $611,450

3509 Redding Rd, Fairfield
$1,100,000
ACTIVE Status ⋅ 24166265 MLS
An exceptional opportunity to build your dream home on one of the most desirable and scenic settings in Fairfield. This beautiful, flat 2.65-acre parcel-approved by the Wetlands Com. for a 5-bedroom, 5-bathroom residence with a pool and pool house-offers both privacy and prestige. The property is situated in the estate section of Greenfield Hill. With its driveway access on Brett Road, a designated "Scenic Road," the lot faces the beauty and character of historic Congress Street. The location is unmatched: moments from the 186-acre Brett Woods Conservation Area and the 155-acre Roy and Margot Larsen Wildlife Sanctuary, both featuring miles of walking trails, and equally convenient to the town centers of Fairfield, Westport, and Southport. There are currently no other similarly sized lots available in Greenfield Hill, making this a rare and valuable opportunity. All of this is just one hour from Manhattan, offering an ideal blend of tranquility, convenience, and prestige.

22 Brett Rd, Fairfield
$15,000,000
7 Beds ⋅ 10 Baths ⋅ ACTIVE Status ⋅ 24104335 MLS
The Ultimate East Coast Sanctuary, Where Privacy Meets Pinnacle Luxury. Surrounded by high stone walls, a fortress of modern architecture is invisible from the street and engineered for the world's most discerning buyers who demand seclusion with proximity to NYC. This 38.91-acre compound is a one-of-a-kind Fairfield County estate. The former home of Richard Rodgers, composer of The Sound of Music, the mid-century main residence has been masterfully reimagined to incorporate 7 private bedroom suites, all with views over the landscaped property. The bespoke renovation was executed with uncompromising attention to detail and a true no-expense-spared philosophy, incorporating commercial-grade infrastructure, superior materials, and artisan-level craftsmanship throughout, as if cost were no consideration. Lofty ceilings and walls of glass are a perfect setting for an art collector. Separate wings radiate off the main rooms, each space private and thoughtfully composed. A hidden screening room, a stunning Moroccan lounge, and a guest wing allow for A-list entertaining. The barn pool house with full kitchen, bath and pro-grade gym, the pool, and a heated paddle court make this a perfect athlete's compound. Property includes renovated stone guest/caretaker cottage and a private office pavilion. The landscape offers open vistas, an orchard, and allowed equestrian use. Live in ultimate style and privacy surrounded by a 155-acre nature access to NYC, Greenwich, Westport and airports.

4800 Congress St, Fairfield

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