Greenfield Hill Real Estate

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Newest Listings in Greenfield Hill

$1,700,000

4 Beds ⋅ 5 Baths ⋅ 24218982 MLS

Tucked away in desirable lower Greenfield Hill, this distinctive Cape Cod offers exceptional privacy, architectural charm, and an opportunity to create a home tailored to your vision. A sweeping circular driveway leads to this beautiful residence featuring rich hardwood floors, generous living spaces, and abundant natural light. French doors span much of the rear of the home, opening to a mahogany deck and seamlessly connecting indoor and outdoor living. The impressive living room features a vaulted beamed ceiling, fireplace with shiplap detailing, and elegant marble wet bar with beverage refrigerator. The main level primary suite offers French doors overlooking the backyard, walk in closets, and a luxurious marble bath. The upper level features two bedrooms sharing a full bath and a third bedroom with an ensuite bath. The kitchen area has been taken down to the studs, with the ceiling raised approximately 11 inches, offering an exceptional opportunity to design a custom kitchen and open concept gathering space. The lower level offers potential for additional living space. Outdoors, enjoy an expansive private lawn, mature landscaping, bluestone patio, and room for a potential pool and pool house, subject to approvals. Minutes from Fairfield's beaches, town center, dining, shopping, and train. A rare opportunity to bring your vision to life in a premier Fairfield location.

453 Merwins Ln, Fairfield

$2,799,900

5 Beds ⋅ 5 Baths ⋅ 24218557 MLS

This extraordinary CT residence has been lovingly RESTYLED IN 2026 including the stunning kitchen, hardwood floors, lighting, HVAC, garage and more. Beautifully sited within the sought-after Estates of Farmstead Hill, this home enjoys the quiet of a cul de sac and commanding views of undulating grounds. Just completed renovations include a striking white Wood Mode kitchen, new matte gold hardware, subway backsplash, and hardwood floors. Outfitted with the serious chef in mind with SS Subzero full size fridge and full size freezer, oversized range and pot-filler, the kitchen is also perfectly poised for entertaining inside and out with access to the great room, formal and casual dining, pantries, rear patio and utility rooms. The vaulted salon/ living room is flooded with light from 2-story windows and leads to the sunroom/billiards. A rear hall off the kitchen includes pantry, laundry, main level bedroom (office) and full hall bath with access to the 3 car garage. Upstairs, the primary suite is a true sanctuary, complete with an elegant bath, dressing room, fireside sitting room, and Juliet balcony. Two bedrooms and an office are serviced in the main hall by a full bath. And a 2nd set of stairs leads to a private wing featuring 2 bedrooms with baths en suite. What completes the lifestyle lies beyond the property lines: Pristine beaches, parks, vibrant restaurants/nightlife, celebrated arts and culture with award-winning schools and recreational outlets. C adden for more info

221 Farmstead Hill Rd, Fairfield

$995,000

4 Beds ⋅ 3 Baths ⋅ 24217675 MLS

Located in the heart of Fairfield's desirable Greenfield Hill neighborhood, this classic Colonial offers over 3,000 square feet of living space on more than two acres. This four bedroom, two and a half bath home features a traditional floor plan with generously sized rooms and wonderful potential for its next owner. Set back from the road along a long driveway, the home welcomes you with a formal living room and dining room, ideal for everyday living and entertaining. The spacious family room is a standout feature, with a wood burning fireplace, and walls of windows that bring in an abundance of natural light. The kitchen features double ovens, a gas cooktop, and a dining area with French doors opening to the deck overlooking the backyard. A convenient main level laundry room completes the first floor. Upstairs, four generously sized bedrooms provide comfortable accommodations, including the primary bedroom with its own private bath. An additional bonus room offers flexible space for a home office, playroom, or recreation area. The partially finished lower level provides additional living space and access to the two car garage. With a new roof, natural gas, generous living spaces, and an expansive, level backyard, this one owner home offers an opportunity to bring your own style and updates to a classic Colonial in one of Fairfield's most sought after neighborhoods. A chance to create something special in Greenfield Hill at a price point rarely found for a home of this size.

195 Wood House Rd, Fairfield

$1,785,000

5 Beds ⋅ 6 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 Media & Game Room with fpl and fully equipped Bar with wine cooler, ice maker and double drawer beverage 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

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The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.

Greenfield Hill Real Estate

Newest Listings in Greenfield Hill

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