Greenfield Hill Real Estate

Welcome to Greenfield Hill, a hidden gem nestled in the heart of Fairfield, Connecticut. This charming neighborhood is renowned for its picturesque landscapes, lush greenery, and a strong sense of community. With its winding roads lined with stately homes and mature trees, Greenfield Hill offers a serene escape from the hustle and bustle of city life while still being conveniently close to urban amenities.

One of the standout features of Greenfield Hill is its rich history, with many homes dating back to the 18th and 19th centuries, showcasing stunning architectural styles that reflect the area’s heritage. Residents here take pride in their neighborhood, fostering a warm and welcoming atmosphere that makes it easy to connect with neighbors and create lasting friendships.

Outdoor enthusiasts will find plenty to love in Greenfield Hill. The area is dotted with parks and nature trails, perfect for leisurely strolls, picnics, or simply enjoying the beauty of the changing seasons. Greenfield Hill is also home to several top-rated schools, making it an ideal place for families seeking a nurturing environment for their children.

Culturally rich and conveniently located, Greenfield Hill provides easy access to Fairfield’s vibrant downtown area, where you can explore a variety of shops, restaurants, and entertainment options. Whether you’re seeking a peaceful retreat or an active lifestyle, Greenfield Hill is the perfect place to call home. Embrace the charm of this idyllic neighborhood and discover why so many are proud to be part of the Greenfield Hill community!

Newest Listings in Greenfield Hill

$1,785,000

5 Beds ⋅ 4 Baths ⋅ 24214910 MLS

Nestled at the end of a cul-de-sac in the beautiful Greenfield Hill neighborhood, this newly 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. Brand new property drainage system installed in October 2026.

203 Wildflower Ln, Fairfield

$1,475,000

4 Beds ⋅ 3 Baths ⋅ 24215458 MLS

Nestled among 3.56 acres of beautiful woodlands, this classic four-bedroom Dutch Colonial offers an inviting blend of timeless character and comfortable living. Enjoy tranquility with easy access to all that Fairfield has to offer. There are hardwood floors throughout, a welcoming foyer, a large living room with fireplace, and sliding doors that lead to an amazing screened porch surrounded by nature, making it the perfect spot for your morning coffee. An updated kitchen and spacious dining room with doors leading to a private patio are perfect for entertaining. Completing the main level are an office and half-bath. Upstairs you will find four bedrooms, two bathrooms, and a large bonus room. The lower level has a recreation room and plenty of storage. Be sure not to miss the two-story barn on the property. It's perfect for the animal enthusiast or as extra space for creative projects and hobbies. It even has a second story that can be transformed into a home office-or just a cool place to hang out! This home is a must see; a real stunner.

50 Judges Hollow Rd, Fairfield

$1,695,000

3 Beds ⋅ 3 Baths ⋅ 24199251 MLS

Cross a babbling brook to a European styled Greenfield Hill home set in magical 2 manicured acres. Charming home showing attention to detail. 3 Fpls, Blt-Ins, Scrn Porch, Crown Molding. Expansion for 4th bedroom possible

140 Labbance Ln, Fairfield

$1,599,000

4 Beds ⋅ 3 Baths ⋅ 24214100 MLS

Welcome to this gracious, 4-bedroom center hall Colonial, ideally situated on .61 acres in Fairfield's sought-after lower Greenfield Hill area. Offering 3,421 square feet of living space, plus an additional 600 finished square feet in the lower level, this sun-filled home combines classic details with a comfortable, open floor plan. 9-foot ceilings, 2 fireplaces, hardwood floors and custom millwork add character throughout. The spacious family room features a dramatic floor-to-ceiling stone fireplace and opens to the eat-in kitchen, complete with stainless steel appliances, double ovens and abundant cabinetry. An elegant dining room, living room with fireplace, powder room, and laundry room complete the main level. Upstairs, four generously sized bedrooms include a primary suite with a walk-in closet and an expansive full bath featuring a double vanity, Jacuzzi tub, and separate shower. Three additional bedrooms offer ample closet space and share a full bath with a tub/shower combination. The lower level features a 36 X 15 finished space perfect for a recreation room, playroom, office, media room or a combination of these! A large unfinished area offers abundant storage space. Outside, the fully fenced backyard with bluestone patio offers a private and peaceful setting bordering wooded, town-owned land. Complete with mudroom, attached 2-car garage, full house generator and security system, this move-in-ready home is centrally located to enjoy ALL that Fairfield has to offer!

88 Springer Rd, Fairfield

$2,300,000

4 Beds ⋅ 8 Baths ⋅ 24214588 MLS

Welcome to 18 Merry Meet Circle, an architecturally distinctive residence nestled within The Ridge, Fairfield's prestigious gated community. Ideally situated near the end of a quiet cul-de-sac in desirable Greenfield Hill, this exceptional home offers remarkable privacy, mature landscaping, and a resort-inspired lifestyle. Residents enjoy a 24-hr. staffed gatehouse, a private clubhouse, a heated Gunite swimming pool, lighted Har-Tru tennis courts, a skating pond, bridle & walking trails. A circular stone driveway welcomes you to a home showcasing distinctive architectural details, natural stone, rich wood accents, and exceptional craftsmanship. Beautifully designed living spaces include a spacious kitchen, separate dining room, and expansive living room with a magnificent stone fireplace. A custom stone-and-wood staircase adds a striking architectural focal point. The thoughtfully designed lower level is an entertainer's dream, featuring a private fitness retreat with gym and authentic sauna, bar area, theater room, butler's pantry, private office, and additional living space. Expansive glass walls and doors create an inviting atmosphere, additional rooms and staff quarters offer flexibility for a variety of needs. Recent improvements include a new roof, updated mechanical systems, new water heater, and whole-home dehumidification system. Residents of The Ridge enjoy a 24-hour staffed gatehouse, private clubhouse and recreation center, heated Gunite pool. Total Sq. Ft. 7,100

18 Merry Meet Cir, Fairfield

$2,695,000

4 Beds ⋅ 7 Baths ⋅ 24211002 MLS

Approached by a winding drive at the end of a quiet cul-de-sac in Fairfield County's premier gated community, The Ridge, this distinguished Colonial Revival residence is privately sited atop a gentle knoll on two beautifully landscaped acres. Expansive lawns, mature plantings, and private terraces create a tranquil setting with exceptional privacy. Spanning Four levels and approximately 7,300 square feet the home is designed for both comfortable everyday living and grand scale entertaining. A spectacular Great Room with fireplace flows into the light filled Kitchen and dramatic 2 story Breakfast Room, with both spaces opening to the terrace for effortless indoor-outdoor living and al fresco dining. A 2-story Foyer, formal Dining Room, Mudroom and home Office complete the main level. Accessed by front and back stairs the second level offers a luxurious Primary Bedroom featuring a fireplace, spa-like Bath and walk in closet, 3 additional en-suite Bedrooms and a large Bonus/Play Room. A sizeable third floor Craft/Office/Multipurpose Room provides exceptional flexibility including possible 5th Br. The home's striking appeal continues in the finished walk out lower level with mirror walled Gym and impressive Party/Game Room with fpl and fully equipped wet bar with wine cooler, ice maker and double drawer under counter refrigerators. Ideally located along the Fairfield/Westport line, The Ridge offers a true Country Club lifestyle with Clubhouse, Pool, Tennis Courts and Playground.

443 Brambley Hedge Cir, Fairfield

$5,975,000

6 Beds ⋅ 8 Baths ⋅ 24209002 MLS

For those who believe luxury should never feel predictable. This remarkable Southport estate is a masterful reinvention of new construction...where timeless architecture meets modern artistry, extraordinary craftsmanship, and effortless living. Every element feels intentional, from dramatic windows and beautifully scaled rooms to custom millwork, sophisticated lighting, advanced technology, and finishes chosen for beauty rather than trend. Walls of glass dissolve the boundary between indoors and out, revealing a private, beautifully landscaped setting with a breathtaking pool and cabana...a sanctuary that feels worlds away, yet is moments from everything. 8800 Sqft of unsurpassed quality offering an exceptional floor plan that must be experienced to be appreciated. Chef's will appreciate the exceptional Kitchen, the primary suite is an indulgent retreat, while exceptional entertaining spaces make the home equally suited to intimate evenings and unforgettable gatherings. A completely separate, perfectly renovated guest house with its own address, utilities & garage offers a rare luxury in itself...privacy & possibilities for guests, extended family, office, caretaker or rental income. And the location may be the ultimate luxury: the beauty and charm of Southport, award-winning Fairfield schools, beaches and amenities, and coveted Westport resident privileges including Compo Beach and Longshore. One extraordinary property. Two exceptional lifestyles. In a word...Perfection.

590 Sturges Hwy, Fairfield

$1,500,000

2 Beds ⋅ 2 Baths ⋅ 24210726 MLS

Welcome to The Enchantment, a magical 2.90-acre oasis in the heart of lower Greenfield Hill. Built in 1894, this charming antique farmhouse has been meticulously renovated and expanded to 2,064 square feet, blending historic character with modern comforts. Originally configured with four bedrooms, the home has been reimagined with an open, inviting floor plan and the flexibility to reintroduce a first-floor bedroom with en-suite bath. Gorgeous wood floors, exposed beams and natural wood trim lend warmth and rustic elegance throughout, while the beautifully renovated kitchen serves as the heart of the home. No detail was overlooked, with a new roof, Marvin windows, boiler, electrical, plumbing, kitchen and baths. Outside, meandering pathways weave through enchanting gardens designed by renowned botanist and floral designer Peter Stephens. Discover bubbling fountains, hidden garden vignettes and unexpected places to gather and retreat. An exceptional collection of outbuildings includes the original barn with vaulted ceilings and loft; an adjoining heated gathering studio with wood floors and new skylights; a picturesque three-stall barn with loft, cupola and attached poultry shed; a dedicated workshop barn; and a large storage shed. Each building has been thoughtfully improved, with new roofs throughout and additional updates as needed. The Enchantment is truly a world of its own-a rare combination of historic charm, modern comfort, extraordinary gardens and versatile spa

1321 Brookside Dr, Fairfield

$1,459,000

4 Beds ⋅ 3 Baths ⋅ 24211408 MLS

Welcome home to 241 Hemlock Hills Road South, a New England charmer nestled on a quiet cul-de-sac and set on a peaceful, private 2+ acre lot. Move-in-ready and filled with warmth, this spacious home offers 10 generously sized rooms across three levels of living. Natural light fills each room through numerous windows, framing beautiful views of the surrounding mature landscaping and surroundings. Standout features include four wood-burning fireplaces, hardwood flooring throughout, custom built-ins, and a thoughtfully designed floor plan that provides a great flow for entertaining as well as everyday living. The second level features four bedrooms, including the spacious primary suite, creating a convenient and comfortable bedroom layout. Step outside to the oversized deck and enjoy the tranquility of this expansive property, where beautiful wild life, mature plantings, and visiting birds create a truly peaceful setting. And while the property feels wonderfully private and tucked away, it is remarkably convenient-just moments from the elementary school, parks, Audubon Society, town center, and shopping. Life feels a little easier here. Enjoy the space, privacy, features, and natural beauty of this special home while creating lasting memories for years to come.

241 Hemlock Hills Rd S, Fairfield

$1,899,000

4 Beds ⋅ 4 Baths ⋅ 24202150 MLS

Classic Greenfield Hill Colonial located in desirable Galloping Hill neighborhood. Wonderful turn-key home has been gently lived in and boasts Formal Living Room with wood burning Fireplace & Formal Dining Room with coffered ceiling and Butler's Pantry. Light-filled Kitchen with new backsplash & Quartzite counter tops offers good space for cooking & entertaining. Laundry Room and Powder Room are located off Kitchen. Family Room with its wood burning Fieldstone Fireplace features roomy space and opens nicely out to refreshing blue slated Patio. Home Office is located on Main Level. Beautiful mill work greets you as you ascend the staircase to the Upper Level. Spacious Primary en-suite Bedroom, en-suite 2nd Bedroom, plus 2 additional well-proportioned Bedrooms and Hallway Bath complete the 2nd Level. Walk-up Attic provides excellent storage. Partially finished walk-out Basement (784 sq ft) offers work out space & space for children to play. Basement with add'l 1,134 unfinished square footage provides opportunity & abundant storage space. Insulated 600 sq ft space located above 3 car Garage could make ideal Bonus Room. Plenty of shopping & dining on either Black Rock Tpk or Downtown Fairfield. The wonderful coastal community of Fairfield boasts 5 scenic beaches. 60 Bridle Trail is an excellent & welcoming family home just minutes to the Merritt Pwy, 10 minutes to I-95, train and downtown.

60 Bridle Trl, Fairfield

$2,195,000

5 Beds ⋅ 5 Baths ⋅ 24208162 MLS

Transport yourself back in time in this classic Greenfield Hill colonial! This renovated 1817 stunner offers over 5,000 square feet of living space - complete with private accessory apartment, a light & welcoming sunroom, bucolic barn and amazing gunite pool with waterfall! Mature plantings and trees abound on this spacious, rolling property. A dramatic, two-story front entry with sweeping staircase welcomes you home. Hardwood floors and high ceilings give even more character and elegance to the home. A more contemporary, open floor plan runs throughout the first floor - highlighted by a chef's kitchen, family room and formal dining room (both with fireplaces), living room, den with fireplace, office and more! The primary bedroom suite with elegant bath and walk-in closet punctuates the fantastic second floor, with three additional bedrooms. The home is perfect for hosting parties and overnight guests. An apartment (w/separate entrance) over the garage, an attached three-car garage and charming front porch are further features of this pastoral, private & relaxing home and property. Enjoy everyday or on the weekends! The two-story barn with three stalls and large pasture adds even more to your experience! It has three large stalls - perfect for trail rides - a stone's throw away at The Fairfield Bridle Trails and Brett Woods! Additional riding opportunities at the nearby Fairfield County Hunt Club. Close to Fairfield & Westport shopping, restaurants, entertainment & commuting

2493 Redding Rd, Fairfield

$1,086,500

4 Beds ⋅ 4 Baths ⋅ 24206575 MLS

Totally refreshed with many new improvements including a stunning kitchen island, this mid-century modern classic home is tucked away at the end of a wide, welcoming cul-de-sac in the heart of Greenfield Hill. Spanning 5,000 sq ft with 4/5 bedrooms and 4 updated full baths, this beauty is set on 2 sprawling, private acres. A prime feature is the breathtaking great room w/soaring 12ft+ ceilings and a dramatic wall of glass. The formal dining room has 9ft ceilings and a bank of floor-to-ceiling windows. The island kitchen with large walk-in pantry has been expanded and is outfitted with newer 2024 top-tier appliances. The adjacent sun room is perfect as a casual eating area and is drenched with sunlight through the two walls of windows. Another main floor feature is a flex room, boasting its own full bath and walk-in closet, ideally suited as either an in-law suite or family room. Retreat to the main floor primary bedroom suite with an updated full bath & an oversized walk-in closet. 3 additional good sized secondary bedrooms round out this spacious and well designed home. Outside, the expansive deck allows you to take in the lush, private grounds. Car enthusiasts will appreciate the two double-bay attached garages, all accessed via a graceful circular driveway. This tranquil location provides easy access to local boutique shopping, vibrant dining scenes, coastal beaches, and convenient transportation links. Opportunity awaits at 480 Riders Lane!

480 Riders Ln, Fairfield

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Greenfield Hill Real Estate

Newest Listings in Greenfield Hill

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