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3674 Congress St, Fairfield
$1,600,000
3 Beds ⋅ 3 Baths ⋅ 24151463 MLS
HIGHEST & BEST DUE BY SUNDAY 2/22 9PM. Discover this charming home, originally built in 1945, in the heart of Greenfield Hill, boasting 3 spacious bedrooms and 2.5 baths with large rooms throughout for comfortable living. The inviting updated, eat-in kitchen features a central island, modern appliances, and plenty of storage. Three wood-burning fireplaces on the first floor with beautiful hearths add warmth and ambiance, while gleaming hardwood floors flow seamlessly across the entire home, complemented by an oversized living room and dining room ideal for entertaining. The kitchen, as well as the family room, complete with custom built-ins and a dedicated gaming area, opens directly to the beautiful and durable Ipe deck for seamless indoor-outdoor living. The property features a cedar roof on the main house; and an asphalt roof on the large two-car garage. Ideally situated just a short stroll to "the shadow of the steeple," site of the cherished annual Dogwood Festival each May, and conveniently close to a charming local farm, adjacent open space, and highly rated schools. Only minutes from the vibrant downtowns of Fairfield and Westport. Enjoy peaceful walks, jogs, or bike rides along quiet, tree-lined streets, embracing the serene New England countryside charm. Commuting is effortless, with the Metro North train station to NYC, downtown shops, restaurants, the YMCA & the main library all just a quick 5-7 minute drive away. Natural gas &city water utilities.

3674 Congress St, Fairfield
107 Buckboard Ln, Fairfield
$1,587,500
4 Beds ⋅ 3 Baths ⋅ 24187463 MLS
Tucked away at the end of a tranquil cul-de-sac in one of Greenfield Hill's most convenient and desirable neighborhoods, this turn-key New England Colonial offers the perfect blend of timeless style, classic design and an exceptional lifestyle at any stage of life. Designed for everyday living and entertaining. Features include an inviting foyer with custom molding, powder room, refinished hardwood floors, Marvin windows, sun-filled formal living and dining rooms. The beautiful granite eat-in kitchen has custom cabinetry, newer appliances, an oversized walk-in pantry and 1st floor laundry. A welcoming family room showcases new custom built-ins and wood burning fireplace with seamless access for indoor-outdoor flow. Upstairs, a spacious primary suite offers a walk-in closet and updated private bath while three additional generously sized bedrooms with ample closet space share the hall bath. Finished lower level expands the living space with a rec room, office area and plenty of storage. Professionally landscaped, flat, one acre fenced rear property with raised garden beds, shed, expanded trex deck with pergola and retractable awning creates an oasis for outdoor living and entertaining. The 'circle' is where bike rides and Easter egg hunts begin and neighbors gather creating a real sense of community. Minutes to town, beach, award winning schools and commuter options.

107 Buckboard Ln, Fairfield
155 Labbance Ln, Fairfield
$1,580,000
5 Beds ⋅ 5 Baths ⋅ 24167159 MLS
A once-in-a-generation Japanese-inspired 3 acre sanctuary on the coveted Westport side of Greenfield Hill, this extraordinary property offers a rare fusion of architecture, artistry, and landscape. Designed by the owner, a master gardener, the grounds unfold as a private retreat where the Sasco River winds through natural boulders, hand-laid stone walls, flowering specimen trees, terraced gardens, and peaceful woodland paths. The striking contemporary residence is equally compelling, with an open floor plan anchored by a dramatic cathedral-ceilinged living room. A centrally positioned mission-style kitchen serves as the heart of the home, while the dining room, sunroom, and family room enjoy sun-filled southern exposure and tranquil garden views. A dedicated art gallery and exceptional custom library further distinguish the main level. The main floor also includes the primary suite and two additional bedrooms, while a private third-floor bedroom with full bath offers ideal guest or office space. The walk-out lower level adds a family room plus a separate apartment with kitchenette, sitting area, bedroom, and full bath. Ready for thoughtful updates, this is a rare opportunity to reimagine and elevate a truly special home in one of Greenfield Hill's most peaceful and breathtaking settings. Minutes to Southport/Fairfield and Westport centers. House is not in a flood zone! Sits up high with a view!

155 Labbance Ln, Fairfield
355 Surrey Ln, Fairfield
$1,550,000
4 Beds ⋅ 4 Baths ⋅ 24179417 MLS
Priced below market value for quick sale! Welcome to 355 Surrey Lane - an extensively renovated home where timeless design meets California contemporary and modern organic luxury finishes. Taken down to the studs and rebuilt with exceptional attention to detail and quality, this turnkey home offers the peace of mind of new construction on a level, private 1 acre lot with an enormous backyard and circular driveway in the highly sought after Greenfield Hill neighborhood. Just about every component of this home is brand new to include: AC, Gas Furnace, ductwork, hot water heater, electrical panel and systems, Anderson windows throughout, kitchen cabinets, premium Kitchenaid appliances and 48 inch double gas oven all under manufacturer warranty, 10 foot quartz waterfall island and laundry. Brand new wide plank engineered hardwood floors throughout the home and 3 fully renovated bathrooms. The living areas feature a wide open floorplan, perfect for entertaining and are highlighted by two striking floor to ceiling fireplaces. The home features expansive windows and doors, filling the home with natural light. Low utility bills from all new energy efficient insulation throughout. Huge additional living room/play room. In-law suite with private entrance and bath. Located minutes from major commuting routes and Fairfield's award winning schools, beaches, parks, restaurants, shopping and train. Hurry - this one will not last long

355 Surrey Ln, Fairfield
1180 Merwins Ln, Fairfield
$1,530,000
3 Beds ⋅ 4 Baths ⋅ 24179278 MLS
Private Greenfield Hill Retreat on 2+ Acres with Guest Suite, Modern Updates & Equestrian Potential.Tucked away on a quiet cul-de-sac in the heart of Greenfield Hill, this rare property offers privacy, flexibility, and modern comfort. From the moment you enter, the craftsmanship is unmistakable featuring a handcrafted staircase, custom millwork, built-ins, and a dramatic barrel ceiling living room anchored by a stone fireplace. The refreshed chef's kitchen includes a center island, double ovens, pantry, and granite countertops, opening to a sun filled sitting area with views of mature plantings. The floor plan offers exceptional versatility. A first floor wing, currently configured as an in-law suite with full kitchen, bedroom, full bath, walk-in closet, and laundry, can easily function as a primary suite, guest retreat, or additional bedroom adapting seamlessly to changing needs. Upstairs, you'll find two addt'l ensuite bedrooms, a cedar closet, and generous walk in storage, providing privacy and comfort throughout. Addt'l highlights include new main level flooring, upgraded lighting, a whole house generator, and reverse osmosis water filtration system, offering both convenience and peace of mind. Outside, a stone terrace overlooks the expansive backyard, while a separate outbuilding provides space for addt'l vehicles, a workshop, or equestrian use. Ideally located near both Fairfield and Westport, the property feels completely private while remaining close to everything.

1180 Merwins Ln, Fairfield
1495 Westport Tpke, Fairfield
$1,500,000
4 Beds ⋅ 4 Baths ⋅ 24047873 MLS
Rich in character and designed for today's lifestyle, this distinctive Fairfield home is privately set on two picturesque acres, framed by classic New England stone walls, white fencing, mature trees, open lawns, a quintessential red barn, and a detached two-car garage. The setting offers exceptional privacy while beautifully balancing Fairfield's country landscape with the convenience of its location. Thoughtfully renovated and expanded in 2012, the home offers an elevated, modern living experience while preserving the architectural details that make the property unique. The beautifully appointed chef's kitchen, with top-of-the-line appliances, opens seamlessly to a great room with soaring vaulted ceilings, a handsome fireplace, walls of windows overlooking the property, and sliders to the private deck. Designed for both entertaining and everyday living, the open layout creates a natural gathering place and an effortless connection to the outdoors. Adding to the home's timeless character are its circa-1749 origins, beautifully preserved through select period details, including the King's Board flooring-an architectural feature traditionally found in some of New England's earliest homes. An adjoining room offers exceptional flexibility as a library, study, or intimate sitting room.

1495 Westport Tpke, Fairfield
485 Mountain Laurel Rd, Fairfield
$1,500,000
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
1115 Galloping Hill Rd, Fairfield
$1,450,000
4 Beds ⋅ 3 Baths ⋅ 24132021 MLS
THANK YOU FOR YOUR STRONG INTEREST; SELLER REQUESTS HIGHEST & BEST OFFERS BY NOON ON MONDAY 3/16/26 thoughtfully updated Colonial in the heart of Greenfield Hill, 1115 Galloping Hill Road is the kind of home that simply feels right. Solid, balanced, and beautifully maintained, it reflects years of careful ownership and intentional improvement. The main level offers an easy flow between kitchen and family room, anchored by a classic brick fireplace and extending seamlessly to a screened sunroom that invites year-round enjoyment. The kitchen has been refreshed with new cabinet fronts, hardware, lighting, and a built-in breakfast nook. Refinished hardwood floors run throughout the home, unified in tone, while a crisp Chantilly Lace palette and curated fixtures create a cohesive, timeless feel. Upstairs, the primary suite is quietly refined, complemented by three additional bedrooms with custom closet systems, updated lighting, and thoughtful design details. The fully permitted lower level has been completely reimagined with new flooring, insulation, heating, windows, and generous storage. Exterior improvements include a widened driveway, new front door, expanded bluestone patio, refreshed landscaping, solar-reflective sunroom windows, and a level lawn enhanced for usability and privacy. Major systems, including septic, roof, windows, and electrical, have been updated. A home that feels settled, solid, and ready for its next chapter.

1115 Galloping Hill Rd, Fairfield
1951 Burr St, Fairfield
$1,403,000
4 Beds ⋅ 3 Baths ⋅ 24206877 MLS
*OFFERS DUE 5PM 9/21* Welcome to this quintessential New England colonial, lovingly cherished by the same owner for over 4 decades. On 2 flat, picturesque acres, this timeless home offers serene, private living while remaining centrally located. A sweeping circular driveway creates a warm arrival, while the sprawling, level backyard provides an ideal setting for outdoor entertaining, with room for a pool and pool house.Inside, traditional character shines with hardwood floors throughout. The main level is designed for both casual daily life and formal hosting. The heart of the home features an expansive eat-in kitchen anchored by a center island, ideal for morning coffee or casual gatherings. A formal living room centers around a fireplace, with classic French doors opening into the dining room. The main level also offers exceptional layout flexibility, including a light-filled office with French doors to a private flagstone patio, a cozy den, a family room with a second fireplace, and a practical mudroom with garage access to keep everyday life organized. Upstairs, 4 generous bedrooms include a primary with an oversized bathroom, the rare convenience of a true 2nd-floor laundry room, and a 2nd full bathroom with double sinks. For extra storage, a full walk-up attic provides additional space. Offering rare privacy, incredible space, and enduring quality in a prime location, this exceptional property presents a wonderful opportunity for its next owners to make it their

1951 Burr St, Fairfield
1192 Catamount Rd, Fairfield
$1,400,000
3 Beds ⋅ 4 Baths ⋅ 24181750 MLS
Rare opportunity in Fairfield's coveted Greenfield Hill! This 2013 custom-built, meticulously maintained home offers the perfect balance of luxury, privacy, and low-maintenance living. Situated on a manageable .28-acres, you'll enjoy the serenity of a country retreat without the upkeep of a large estate. Set along one of Fairfield's designated scenic roads, and with Brett Woods Open Space as its backdrop, 1192 Catamount is surrounded by natural beauty while remaining incredibly connected to both Fairfield & Westport. Outside, this home welcomes you with a wraparound front porch. Inside, the open floor plan showcases 9'+ ceilings and exceptional custom millwork. The main level features a family room anchored by a floor-to-ceiling stone gas fireplace, a paneled office behind french doors, a gourmet kitchen with Viking appliances and a marble center island ideal for entertaining. The dining area is framed by floor-to-ceiling windows that capture the surrounding woodland landscape. Upstairs, the primary suite offers a tray ceiling, walk-in closet, and spa-inspired marble bath.Two additional bedrooms share a hall bath, conveniently located near a dedicated laundry area.The lower level offers versatility as a guest suite with its own full bath. A full standing height attic with natural light provides future expansion potential.Recent upgrades include exterior/interior paint, a new driveway, patio, and a whole-house generator which offer true move-in confidence from day one

1192 Catamount Rd, Fairfield
240 N Cedar Rd, Fairfield
$1,400,000
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
4041 Redding Rd, Fairfield
$1,400,000
5 Beds ⋅ 4 Baths ⋅ 24180399 MLS
Compelling Value in Greenfield Hill! Nestled amid mature trees and natural surroundings, this 5-bedroom, 4-bath home offers an exceptional combination of space, privacy, and functionality. The open living room and family room provide flexible living spaces with seamless access to the covered porch and expansive deck overlooking the peaceful setting and side yard. The spacious eat-in kitchen features abundant workspace, generous cabinetry, and room for casual dining. Adjacent to the kitchen, the dining room is equally suited for everyday meals and special occasions. A mudroom located just off the kitchen provides its own entrance and access to the oversized three-car garage. A unique spiral staircase offers secondary access to the primary suite. A dedicated main-level office and full bath add convenience and versatility. Upstairs, the spacious primary suite is complemented by four additional bedrooms and two full baths. The finished lower level provides generous bonus space for a playroom, media room, fitness area, or recreation room beyond the reported square footage. In addition to the attached three-car garage, a detached two-car garage offers valuable extra space for vehicles, bikes, equipment, hobbies, or creative use. Enjoy a private setting approximately 15 minutes from Fairfield Center, Westport, Easton, and Weston, with convenient access to shopping, dining, recreation, and transportation.Greenfield Hill living at an exceptional value!

4041 Redding Rd, Fairfield
223 Mistywood Ln, Fairfield
$1,380,000
4 Beds ⋅ 3 Baths ⋅ 24175165 MLS
HIGHEST AND BEST TUES 5/19/26 AT 2 PM. Welcome to 223 Mistywood Lane - a beautifully maintained 4-bedroom, 2.5-bath retreat offering privacy and tranquility on over 2 picturesque acres. Filled with natural light, this inviting residence features recently remodeled bathrooms, hardwood floors throughout, fresh interior paint, and a thoughtfully designed layout ideal for both everyday living and entertaining. The bright kitchen is both stylish and functional, showcasing granite countertops, a charming shiplap backsplash, new appliances, a spacious walk-in pantry, and a designated dining area with a wood-burning fireplace. The stunning sun-filled room lined with windows creates the perfect space to relax and enjoy views of the beautifully landscaped gardens and serene surroundings. The second floor features four bedrooms, including a spacious primary suite with an oversized dressing room and a large en-suite bath with a soaking tub. A beautifully designed laundry room adds convenience and character to the home's well-appointed living spaces. Adding to the property's appeal is a recently remodeled barn-style garage with a finished bonus space above, offering endless flexibility as a playroom, home gym or studio. Surrounded by beautiful gardens and peaceful outdoor spaces, this exceptional property offers a rare combination of privacy, character, and convenience. Recent updates include a new well water pump and a high-efficiency propane boiler, providing added peace of mind

223 Mistywood Ln, Fairfield
1488 Sturges Hwy, Fairfield
$1,355,500
5 Beds ⋅ 4 Baths ⋅ 24177506 MLS
This Greenfield hill Charming colonial, sits on a 1.6 acre lot, right at the border of Fairfield and Westport and only 6 away minutes from the Southport train station and multiple beautiful beaches. Cozy and stylish with a twist of French flair, this well maintained property offers, 5 bedrooms, including a nursery right by the primary suite, 3.5 bathrooms and 5 garages, 3 being attached to the house. On the first floor a large living room leads to an open concept dining room and a bright kitchen, perfect for gatherings. On the second floor, the 5 bedrooms and 3 bathrooms as well as a dedicated office space await you. A full house generator has been installed. Be the first to discover this hidden gem. Agent/co owner. Cameras are installed outside. UPDATE: Sellers are thanking all agents and potential buyers for their interest and are asking for Highest and best offers by Tuesday June 9th noon.

1488 Sturges Hwy, Fairfield
585 Hoydens Ln, Fairfield
$1,350,000
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
1061 Galloping Hill Rd, Fairfield
$1,330,000
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
126 Rolling Hills Dr, Fairfield
$1,310,000
4 Beds ⋅ 4 Baths ⋅ 24158186 MLS
Rolling Hills Drive is the kind of street where homes feel settled into their surroundings, quiet and residential, with attractive homes lining the neighborhood and nature close at hand. Just moments from hiking trails, Lake Mohegan, and Smith Richardson Golf Course, it's a setting that offers both neighborhood connection and easy access to the outdoors. At 126, a classic Colonial sits gracefully on two private acres. The property evolves beautifully through the seasons: green lawns in summer, vibrant foliage in fall, and peaceful snow-covered grounds in winter, each bringing its own character to the setting. Inside, the home carries the same warmth and ease, with cozy, welcoming living spaces anchored by a bright, updated kitchen that naturally becomes the heart of the home. Four full baths add a level of comfort and convenience that makes daily life and hosting feel effortless. Outside, a bluestone front porch with river rock accents offers an inviting place to begin the day, while the backyard opens to broad lawn and a firepit gathering area tucked into the landscape. It's the kind of property where afternoons stretch into evenings, and where outdoor living becomes part of daily life. Inside and out, the home reflects the enduring appeal of a traditional Colonial: balanced, welcoming, and easy to live in. A property defined by space, natural surroundings, and the neighborhood character that makes Rolling Hills Drive one of Fairfield's most peaceful residential settings.

126 Rolling Hills Dr, Fairfield
112 Calico Ln, Fairfield
$1,300,000
4 Beds ⋅ 3 Baths ⋅ 24168777 MLS
Location, location, location! Welcome to this delightful contemporary located at the end of a quiet cul-de-sac in lovely Greenfield Hill. With 4 bedrooms, 2.5 baths and a floor plan offering numerous possibilities for today's living and work lifestyles, this home checks so many boxes. A gracious Living Rm with vaulted ceiling brings the outside in with a wall of windows along the back. Enjoy a lovely view of the trees and backyard as soon as you step in the entry. A formal Dining Rm with built-in buffet and a nice Screened Porch with bluestone floor, also open to the back. The large bright Kitchen has granite countertops, separate island with cooktop, an eat-in Breakfast area, walk-in pantry and new GE Cafe appliances added in the Fall of 2021. Upper level has a Primary Bedroom with a spacious walk-in closet. Prepared to be wowed with the fully updated en-suite bath with soaking tub and separate shower. Two additional bedrooms with a full Bath along with large hallway closets for storage complete the floor. Lower level has a Family Room with wood-burning fireplace and built-in bookshelves. Off this room is the 4th Bedroom, with an Office in back. The finished Basement below offers even more space for play and relaxation. Lovingly cared for by the same family for 25 years, other notable features include a full house generator plumbed to the gas line and a new furnace in October 2020. Ask agent for additional features - you don't want to miss seeing this one!

112 Calico Ln, Fairfield
3725 Redding Rd, Fairfield
$1,300,000
4 Beds ⋅ 4 Baths ⋅ 24161267 MLS
Nestled in the heart of coveted Greenfield Hill, this beautiful classic New England Colonial blends timeless charm, modern comfort & exceptional privacy. Set on 3.5 picturesque acres, the property feels like a private retreat yet is just minutes from town, beaches & Fairfield's top-rated schools. Designed for everyday living & entertaining, the home offers over 4,000 sq ft of thoughtfully designed space with sun-filled rooms & hardwood floors. The heart of the home is a spacious eat-in kitchen with stainless steel appliances plus a built-in bar area flowing into the inviting living room with a fireplace & large windows overlooking the serene property, perfect for gathering with family & friends. A dramatic family room with vaulted ceilings, fireplace & sliding doors leads to a large deck for seamless indoor-outdoor living surrounded by nature. The light-filled primary suite is a true sanctuary with a walk-in closet, fireplace, a luxurious spa-like bath with Carrara marble, heated floors & a soaking tub. The finished 3rd floor offers a 4th bedroom & full bath/versatile bonus space (au pair suite, office, playroom). A walk-out lower level has flexible space for a playroom, office or gym, plus a nearby stone patio. Expansive grounds feature open lawn, gardens, full deer fencing, mature trees, a tranquil brook-perfect for relaxing or entertaining in a peaceful natural setting. This timeless, elegant Greenfield Hill home with exceptional space & privacy is a rare opportunity.

3725 Redding Rd, Fairfield
1090 Galloping Hill Rd, Fairfield
$1,250,000
4 Beds ⋅ 3 Baths ⋅ 24173423 MLS
BASED ON STRONG INTEREST, PLEASE SUBMIT ALL OFFERS, HIGHEST & BEST, BY 5PM MONDAY MAY 18. Sitting pretty behind a charming fieldstone wall, in a sought after neighborhood, this long loved Garrison Colonial feels fresh and inviting! Recent updates include a brand new high efficiency boiler and hot water heater, new roof, new gravel driveway with Belgian Block, new Pella windows, new Bathrooms detailed with Turkish tile, interior paint in soft hues of grey, and gleaming hardwood floors throughout. The classic center hall leads to a sunny Living Room, and alternately to the Family Room, anchored by a cozy fireplace with raised hearth. The Eat in Kitchen opens to the Dining Room. The Den/Office, Laundry and Powder Room complete the main level. Upstairs, four generously scaled Bedrooms include a Primary en suite Bedroom and three other Bedrooms which share a hall Bathroom. Walk up Attic offers additional storage. Outside, the expansive deck and bluestone patio overlook an exceptionally private and flat 1.1 acre of lush lawn, specimen trees, and a distant shed that looks like a small vintage barn. Sited at the highest point of Galloping Hill, this rare panoramic vista elicits a feeling of pure serenity. Convenient to Fairfield's town center, with restaurants, shopping, library, train and beaches, this special slice of Greenfield Hill is a wonderful place to call home!

1090 Galloping Hill Rd, Fairfield
209 Merwins Ln, Fairfield
$1,180,000
3 Beds ⋅ 2 Baths ⋅ 24154961 MLS
Rare lower Greenfield Hill opportunity at an accessible price point. Set on 2 private acres, 209 Merwins Lane offers charm, privacy and everyday livability in one of Fairfield's most sought after locations. Enjoy easy access to Greenfield Center, a quick drive to Westport and a convenient direct route to Fairfield Train Station, just 3.5 miles away. This classic center hall Cape is warm, inviting and easy to love. The main level features a living room with fireplace, traditional dining room, functional kitchen, an oversized rear family room that creates wonderful additional living space and a full bath. In addition, there is a flexible first floor room, currently used as additional living space and a home office, adds convenience for today's lifestyle while offering options for guests, work from home or future needs. Upstairs, two generously sized bedrooms share a full bath off the center hall. One bedroom was previously two bedroom rooms, offering added flexibility within the existing footprint if desired to convert back to three bedrooms. Perfect for downsizers, first time Greenfield Hill buyers or anyone seeking privacy, land and location, this home offers immediate appeal with meaningful long term potential. Move right in, enjoy the charm and explore future possibilities at your own pace in a beloved Fairfield neighborhood.

209 Merwins Ln, Fairfield
2514 Redding Rd, Fairfield
$1,140,000
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
570 Burr St, Fairfield
$1,085,000
4 Beds ⋅ 3 Baths ⋅ 24199075 MLS
Come see this well-maintained 4-bedroom, 2.5-bath ranch set on over 2 acres in Fairfield's Greenfield Hill neighborhood. The spacious corner lot offers a private fenced-in yard along with a meticulously maintained barn. Inside, the home features central air, natural gas heat, a new deck, and multiple fireplaces. The finished lower level adds plenty of additional living space with a second kitchen, bathroom, two additional rooms, and a large entertainment area-perfect for an in-law setup, guests, or extended living. It also offers direct access to the two-car garage. With over two acres, plenty of living space, and so much potential, this is a great opportunity to make this Greenfield Hill property your own.

570 Burr St, Fairfield
208 Wildflower Ln, Fairfield
$977,000
3 Beds ⋅ 2 Baths ⋅ 24167637 MLS
RESPECTFULLY; PLEASE SUBMIT HIGHEST AND BEST BY MONDAY 27TH @ 6 PM. Everything Retouched | 2+ Acres | Expansion Opportunity Located in desirable Greenfield Hill, this fully remodeled single-level ranch offers estate-style living with exceptional expansion potential. Set on over 2 level acres-the smallest home on a street of significantly larger residences-this property presents a rare opportunity to build equity and expand. The usable yard features stone walls, classic New England charm, and privacy, with inland wetlands toward the rear. Ample space for outdoor living or a future pool, plus a chicken coop and storage barn/shed for added versatility. Exterior features include a newer roof, gutter guards, new cedar shingles, cable railing, cedar tongue-and-groove deck ceiling, and high-end materials throughout. Take note of the incredible screened-in back deck, composite front porch, new windows, attached 2-car garage, and storage shed. Above-and-beyond mechanicals include propane heat fueled home w/ two, 100 gallon tanks, Trane HVAC central air, Takagi tankless hot water, fully fenced backyard, and Generac generator. Freshly painted interior with hardwood floors, updated kitchen with extensive cabinetry, quartz island, coffee bar, pantry, and abundant storage. Additional highlights include an ensuite primary bedroom, fireplaced living room, ceiling fans, full unfinished basement spanning the home, and smart home Lutron Caseta system. See full list of highlights and features.

208 Wildflower Ln, Fairfield
3509 Redding Rd, Fairfield
$950,000
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

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