Greenfield Hill Homes with Roger Ludlowe Middle school

Welcome to Greenfield Hill, a picturesque neighborhood nestled in the heart of Fairfield, Connecticut. This charming community is known for its serene landscapes, tree-lined streets, and a strong sense of community, making it an ideal place for families and individuals alike. Greenfield Hill boasts a rich history, with beautiful homes that reflect a variety of architectural styles, from classic colonial to modern designs, ensuring there’s something for everyone.

One of the standout features of Greenfield Hill is its proximity to Roger Ludlowe Middle School, making it an attractive choice for families with school-age children. The school is renowned for its commitment to academic excellence and offers a supportive environment where students can thrive. Parents will appreciate the convenience of having such a highly regarded institution just a stone's throw away, allowing for easy commutes and active parental involvement in school events.

The neighborhood is also home to numerous parks and recreational areas, providing ample opportunities for outdoor activities and family gatherings. Whether you enjoy hiking, biking, or simply taking a leisurely stroll, Greenfield Hill offers a tranquil escape from the hustle and bustle of city life.

In addition to its natural beauty, the community is conveniently located near shopping, dining, and cultural attractions in Fairfield, ensuring that residents have access to everything they need. With a blend of suburban charm and urban convenience, Greenfield Hill is more than just a place to live; it's a vibrant community where you can create lasting memories. Come discover the charm of Greenfield Hill today!

Newest Greenfield Hill Homes with Roger Ludlowe Middle school

$1,925,000

4 Beds ⋅ 4 Baths ⋅ COMING SOON Status ⋅ 24206227 MLS

Tucked at the end of a quiet Greenfield Hill cul-de-sac, 550 Wellington Drive feels like a true retreat-private, peaceful and designed for the way you actually want to live. Set on 2.47 secluded acres, this 4-bed, 4,776sqft home offers an exceptional amount of space to gather, entertain and spread out, with a floor plan that gives everyone a place of their own. The 1st floor is especially expansive, with a gracious living room, dramatic vaulted family room, oversized playroom, sunroom and sophisticated wood-paneled office-spaces that easily adapt for entertaining, working from home, play or simply finding a quiet corner to unwind. The kitchen sits at the heart of the home, creating an easy connection between everyday living and the many gathering spaces. Upstairs, four bedrooms provide a comfortable separation from the main living areas, complemented by recently updated bathrooms. Outside is where 550 Wellington truly becomes an escape. Surrounded by mature landscaping and complete privacy, the backyard resembles a private resort with pool, expansive deck, screened-in porch and abundant space for outdoor dining, entertaining and long summer days at home. A three-car garage completes the offering. Spacious yet inviting, private yet close to everything Greenfield Hill has to offer, 550 Wellington Drive is a homemade for gathering, entertaining and getting away-without ever having to leave home.

550 Wellington Dr, Fairfield

$2,690,000

5 Beds ⋅ 5 Baths ⋅ COMING SOON Status ⋅ 24205145 MLS

A rare Greenfield Hill find, 1074 Sturges Highway pairs the presence of a classic Colonial with a sleek, thoroughly modern point of view. Thoughtfully reimagined, the home retains its original craftsmanship while introducing clean-lined updates and a minimalist sensibility that feels chic, current and effortless. Inside, the balance between old and new is masterfully struck. Original millwork and architectural details are paired with elegantly edited finishes, creating spaces that feel sophisticated without ever tipping into formal. The layout flows naturally for everyday living, with room to gather, entertain and simply enjoy the house. Set on over 2 acres of impeccably manicured and extremely private grounds, the property offers a rare sense of seclusion. A gorgeous patio with fireplace extends the living space outdoors, setting the scene for summer dinners, cocktails and fireside evenings. A newly constructed garage with loft above adds flexibility for a home office, studio, gym or creative retreat. Where classic architecture meets a fully modern point of view, 1074 Sturges Highway is a masterclass in understated sophistication - Greenfield Hill living, reimagined. Fairfield Schools: Dwight, Ludlow, Ludlow.

1074 Sturges Hwy, Fairfield

$2,395,000

4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24203568 MLS

This beautifully crafted 4,600 sq. ft. Colonial, built by renowned builder Frank Dooley, combines exceptional craftsmanship with thoughtful design. Located on a welcoming cul-de-sac in lower Greenfield Hill, the home features spacious rooms with clear sightlines that create a comfortable flow. At the center of the home, a generous kitchen seamlessly connects to the dining area and one of two large stone patios, ideal for both everyday living and entertaining. The expansive family room and elegant front-to-back living room each feature a fireplace, while a charming sunporch offers a cozy retreat. A finished bonus room above the garage provides flexible space for 5th bed, media room. Upstairs, four spacious bedrooms include a well-appointed primary suite with 2 full baths, an ensuite bedroom, and two additional bedrooms sharing an updated hall bath. Abundant custom built-in storage throughout and a finished third floor office enhances the home's versatility. The level, fenced, and beautifully landscaped 2+acres, designed by Oliver's Nursery, features irrigation and outdoor lighting. A 11'-23' room accessible from the yard and garage offers extra storage with finishing potential. Enjoy the convenience of walking to local shops and the farmers market, with easy access to downtown Fairfield, Merritt Pkwy, and I-95. This home offers effortless living in a prime location where everyday life feels relaxed and refined.

128 Cobblers Hill Rd, Fairfield

$2,095,000

6 Beds ⋅ 9 Baths ⋅ ACTIVE Status ⋅ 24202996 MLS

Just a few blocks from the Greenfield Hill Green, an extraordinary opportunity awaits: a beloved estate, held by the same owners for more than 20 years, now reimagined for its next chapter. Taken virtually to the studs and thoughtfully rebuilt, much of the transformative work has already been done - creating the rare opportunity to step in at an exciting moment and complete a nearly 9,000-square-foot home entirely to your own vision. A new roof, siding, insulation, Marvin windows and doors, subflooring, extensive plumbing rough-ins and mechanical systems are among the significant improvements already in place, along with an exceptional newly built four-car garage. What remains is the rewarding part: the finishes, details and personal choices that will make it yours. Set on one of Greenfield Hill's picturesque properties, the home's generous, light-filled floor plan was designed for both everyday living and effortless entertaining. The main level flows between expansive living and family rooms, an eat-in kitchen, office, mudroom and potential first-floor en-suite bedroom. Upstairs, beautifully proportioned en-suite bedrooms offer privacy and flexibility, while the space above the four-car garage presents the potential for a private two-bedroom, two-bath guest or in-law suite with its own entrance.

201 Whites Hill Ln, Fairfield

$1,295,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 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

$4,499,000

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

$3,150,000

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

$899,000

ACTIVE UNDER CONTRACT Status ⋅ 24184843 MLS

Rare opportunity to create a custom residence on 2.08 acres in coveted lower Greenfield Hill. Set on beautiful Hubbell Lane, this raw land parcel offers 258.45 feet of frontage and a special chance to build in one of Fairfield's most desirable neighborhoods, where open building lots are increasingly difficult to find. Site work and preliminary environmental review have been completed, including wetland delineation and septic feasibility testing. Per the information provided, the wetlands are localized resource areas, not parcel-wide, and recent percolation testing produced encouraging results indicating the property appears capable of supporting an on-site septic system for a future single-family residence. Buyer to perform all due diligence with the Town of Fairfield, including Conservation, Health, Zoning, driveway/access, septic design and final approvals. An exceptional Greenfield Hill offering for an end user, builder or investor looking to bring a custom vision to life.

101 Hubbell Ln, Fairfield

$1,875,000

4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 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

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