Greenfield Hill Real Estate

Welcome to Greenfield Hill, a hidden gem nestled in the heart of Fairfield, Connecticut. This picturesque neighborhood is renowned for its lush landscapes, charming homes, and a strong sense of community. As you stroll through the tree-lined streets, you'll be captivated by the blend of historic architecture and modern elegance, with properties that range from sprawling estates to quaint cottages.

Greenfield Hill boasts an abundance of natural beauty, with scenic parks and open spaces perfect for outdoor enthusiasts. The nearby Greenfield Hill Park offers walking trails, picnic areas, and stunning views that invite residents to unwind and enjoy the tranquility of nature. The area is also home to several prestigious private schools and a strong public education system, making it an ideal choice for families seeking a nurturing environment for their children.

Culturally rich and vibrant, Greenfield Hill is just a stone's throw away from downtown Fairfield, where you’ll find a delightful mix of boutique shops, gourmet restaurants, and local cafes. The community hosts various events throughout the year, fostering connections among neighbors and creating a warm, inviting atmosphere.

Conveniently located near major highways and public transportation options, Greenfield Hill offers easy access to the bustling cities of Bridgeport and New Haven, as well as the stunning Connecticut coastline. With its perfect blend of suburban charm and urban convenience, Greenfield Hill is not just a place to live—it's a place to thrive. Come discover the unique allure of this exceptional neighborhood and find your dream home in Greenfield Hill today!

Newest Listings in Greenfield Hill

$1,599,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE UNDER CONTRACT Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE UNDER CONTRACT Status ⋅ 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 ⋅ ACTIVE UNDER CONTRACT Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ 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

$950,000

5 Beds ⋅ 4 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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

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