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$1,599,000
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
$4,900,000
6 Beds ⋅ 8 Baths ⋅ 24184556 MLS
As you enter 80 Governors Lane down a private driveway, discover an 8.5-acre estate blending timeless elegance with serene privacy. This circa 1933 farmhouse, designed by architect Jack Franzen and beautifully restored, features wide plank black walnut floors, exposed beams, and a bread oven fireplace. Six spacious bedrooms include a luxurious Primary Suite with vaulted ceilings, carved mantle fireplace, dual walk-in closets, and a private balcony. Five full and two half baths feature tumbled marble flooring and marble vanities for spa-like comfort. Warm living spaces with fireplaces and tall windows create perfect gathering spots, including a Formal Dining Room, a Den with wet bar, and a cozy Family Room. The chef's kitchen boasts custom cabinetry, Jerusalem stone countertops, a copper sink island, banquette dining, and terraces for al fresco meals. A heated breezeway links to a restored Goodspeed Farm barn, plus a one-bedroom apartment and a three-car garage for multi-generational living. The Pool House offers cathedral ceilings, a granite bar, and doors to stone terraces overlooking a heated Gunite pool, spa, and pond. Enjoy privacy with convenient access to top schools, fine dining, cultural venues, beaches, and NYC trains-an extraordinary sanctuary harmonizing nature and refined living.

80 Governors Ln, Fairfield
$1,295,000
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
$1,689,000
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
$3,400,000
5 Beds ⋅ 6 Baths ⋅ 24189678 MLS
Privately sited in the heart of Greenfield Hill, this updated home blends European-inspired architecture with the modern comforts today's luxury buyers value most. Rich in character, it offers soaring ceilings with exposed wood beams and skylights, wide-plank hardwood floors, custom built-ins, antique mantels, and repurposed antique doors throughout. The dramatic family room flows to a private office, wet bar, and chef's kitchen beneath an expansive skylight. The desirable first-floor primary suite has been transformed with a new spa bath, new gas fireplace, and atrium with a private entrance. Upstairs, a second primary suite features an en-suite bath, dressing room, fireplace, and private balcony. A renovated one-bedroom guest residence with new flooring, updated kitchen and bath, washer/dryer, and private entrance is ideal for extended family, guests, an au pair, or home office. Extensive improvements include a generator, water purification system, drainage system, irrigation, security system with cameras, restored and re-stained roof, renovated mudroom/laundry room, gardens with bluestone walkways and raised beds, and new front fencing. Expansive terraces overlook beautifully landscaped grounds with mature specimen trees and perennial gardens. Just minutes from town, beaches, train, restaurants, and Fairfield Country Day School, this exceptional Greenfield Hill property offers timeless character, privacy, and extensive improvements. Ready to enjoy from the day you arrive!

1760 Hillside Rd, Fairfield
$1,100,000
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
$1,895,000
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
$1,298,000
4 Beds ⋅ 3 Baths ⋅ 24187463 MLS
**Sellers are requesting dealine for Best offers Monday July 20th 5pm***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
$1,548,000
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
$2,499,000
5 Beds ⋅ 7 Baths ⋅ 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
$950,000
5 Beds ⋅ 4 Baths ⋅ 24189981 MLS
ENDLESS POTENTIAL in Sought-After Greenfield Hill. Opportunity awaits to restore this once-graceful Colonial to its former grandeur. Set on a beautiful, level 2.41-acre parcel in the highly desirable Greenfield Hill neighborhood, this property offers the chance to create a truly exceptional estate. Steeped in character and nostalgia, the home features generously sized rooms, hardwood floors throughout most of the house, double staircases, and a walkout basement. With more than five bedrooms, an expansive kitchen ready to be reimagined as the heart of the home, a formal dining room designed for memorable gatherings, a spacious living room with a fireplace, and a screened porch that once welcomed quiet afternoons, the possibilities are endless. Bring back to life the tennis court that hasn't been enjoyed in years. This property requires extensive renovation and is being offered as an opportunity for buyers with vision. Whether you're looking to restore its timeless charm or create your dream home from the existing footprint, the setting and scale provide an outstanding foundation. With thoughtful planning and investment, 2514 Redding Road has the potential to become a magnificent Greenfield Hill residence once again. Buyer to do their own due diligence.

2514 Redding Rd, Fairfield
$1,995,000
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
$2,850,000
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
$2,200,000
5 Beds ⋅ 6 Baths ⋅ 24186610 MLS
Nestled at the end of a cul-de-sac in the beautiful Greenfield Hill neighborhood, this fully updated and renovated home sits on a private 2.4-acre lot and offers Fairfield living at its finest. This 5-bedroom home, with four full and two half bathrooms, boasts spacious interiors, an open floor plan, all-new finishes, and a brand-new primary bedroom suite addition above a three-car garage. The exterior is just as stunning as the interior, featuring custom stonework and a fully updated gunite inground pool, ready to be enjoyed this summer. The home offers an effortless indoor-outdoor lifestyle, perfect for relaxing at home or entertaining guests. Move-in ready, 203 Wildflower Lane is the perfect blend of quality, privacy, and location.

203 Wildflower Ln, Fairfield
$1,949,000
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
$3,988,000
4 Beds ⋅ 6 Baths ⋅ 24184587 MLS
Set within The Ridge in Greenfield Hill, Fairfield's gated residential community, this residence has been completely rebuilt and thoughtfully reimagined with the scale and finish of new construction. Spanning over 8,000 sq ft, the home offers four bedrooms and six full and two half baths, with wide plank oak floors, multiple fireplaces, and expansive windows that frame tranquil pond views. A double height foyer with floating staircase introduces sunlit living spaces that move naturally from formal rooms to a chef's kitchen appointed with double Sub-Zero and Wolf appliances, quartzite surfaces, and a built-in bar adjoining the family room, while a main level suite provides flexibility for guests or a private office. Upstairs, the primary suite features vaulted ceilings, a fireplace, walk-in closets, and dual marble baths with heated floors, accompanied by two additional en suite bedrooms and a laundry room. The walkout lower level offers additional living space with a fireplace, kitchenette, wine room, full bath, and flexible areas for guests, work, or recreation. Exterior stonework, a metal roof, terraces with fire pit and built-in grill, smart home technology, generator, and all new systems complete the property, with community amenities including a staffed gatehouse, clubhouse, pool, tennis courts, and private roads minutes from Fairfield and Westport town centers, area beaches, and rail access to NYC!

475 Fence Row Dr, 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
$1,875,000
4 Beds ⋅ 5 Baths ⋅ 24180338 MLS
2177 Cross Hwy welcomes you home. This extensively renovated iconic contemporary awaits your personal touches. The blending of dramatic architecture with everyday comfort, offering nearly 4,000 sq ft of functional living space designed for gathering, relaxing and entertaining. Soaring 22' ceilings, oversized windows and park-like views fill the main living area with light, while a striking 3-story chimney with 3 wood-burning fireplaces creates a natural place to come together. The gourmet kitchen features a vintage Viking appliance package including gas range, wall oven and wine cooler. 2 dishwashers and custom island, opening to a deck with awning overlooking the pond and natural habitat. The 1st-floor primary suite offers a private retreat with walk-in closet, spa bath, gas fireplace and direct access to the pool and bluestone patio. Additional bedrooms and updated baths provide flexible space for guests, work or quiet retreat. Outside, the property becomes an extension of the home with a free-form gunite pool with new mechanicals and lighting, a stately new entrance with custom metal roof and aluminum gutters, granite sitting walls and bluestone landing to new steps that lead to a lighted driveway 500 feet to the road. resurfaced tennis court, new 10'x22' tigerwood deck. Renovation List and photos can be found on MLS docs.

2177 Cross Hwy, Fairfield
$1,295,000
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
$925,000
2 Beds ⋅ 2 Baths ⋅ 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 ⋅ 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
$2,650,000
4 Beds ⋅ 5 Baths ⋅ 24173048 MLS
A gorgeous Farmhouse Colonial tucked away on 2+ picturesque acres & minutes to Fairfield & Westport town await. Natural beauty, brilliant architecture, craftmanship & updates combine to make this home a standout. Featuring 12 rooms flooded w/ 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 so much w/ 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. Numerous updates throughout 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. The 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 for its next chapter.

3007 Redding Rd, Fairfield
$2,275,000
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
$995,000
1 Baths ⋅ 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
$15,000,000
7 Beds ⋅ 10 Baths ⋅ 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
$3,750,000
5 Beds ⋅ 6 Baths ⋅ 24132064 MLS
Greenfield Hill proposed new construction on a 2.65-acre lot along a Town-designated Scenic Road, to be built by award-winning design-builder Bonnie Paige in collaboration with Vicente Burin Architects. The proposed residence is based on a design sold in Southport Village; interested buyers may tour similar homes and meet the team to tailor plans, finishes, and timeline. The property sits among notable estate properties and near Brett Woods Conservation Area (186 acres) and the Roy and Margot Larsen Wildlife Sanctuary (155 acres), with convenient access to the centers of Fairfield, Southport, and Westport and approximately 55 miles to Manhattan. Construction will begin after purchase and execution of the build contract. The site is approved for a pool, and a pool house can be added at additional cost. Also offered as land only, MLS #24114632, asking $1,300,000. Concept drawings, renderings, and photos are for design intent and aesthetic review. A rare opportunity to build in bucolic Greenfield Hill.

22 Brett Rd, Fairfield

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