+1.203.650.6870
jennifer(dotted)lockwood(at)cbmoves(dotted)com
Jennifer Lockwood Homes

Main Content

Greenfield Hills

The Greenfield Hill neighborhood is the perfect location for those seeking a tranquil setting of treelined streets, rolling green lawns,  and historic architecture.  One of the more affluent neighborhoods in Fairfield, Greenfield Hill, is just minutes to the Merritt Parkway and offers its own upscale shopping center with boutique shops, ample open space for those who enjoy active or leisure walks, equestrian trails for additional outdoor activities, and The Patterson Club— a private country club providing first-class golf, tennis and swimming facilities.

Helping to give the neighborhood its distinct identity is the requirement that individual residential properties have a minimum of two acres.  In addition to its lush, pastoral setting, Greenfield Hill also enjoys a rich history and is recognized by the National Register of Historic places.  The most famous and picturesque landmark is the Greenfield Hill Congregational church which was established in 1725.  And with a volunteer society actively involved in preserving the neighborhood’s historic character, you can see why this neighborhood continues to draw luxury home buyers searching for large estates and historic homes in a tranquil and private setting.

Greenfield Hill offers buyers a small community feel with activities and festivals that contribute to the neighborhood’s close knit community.  One of the most popular events is the annual Dogwood — bringing craftsmen and artists to showcase their works and attracting visitors from all over the region.  This festival takes place over the Mother’s Day weekend when the Dogwood trees are in full bloom with their vibrant pink and white blossoms.

Another favorite family event is the annual Pumpkin Festival held at Greenfield Farm in October — a fun activity for all ages celebrating the traditional harvest season in all its bounty.  Plus, every Saturday from May thru October you can visit the longest running Farmers Marketin Fairfield located on Hillside Rd next to Greenfield Hill Center where you can get your fresh fruits and vegetables along with fresh fish, your favorite bakery items and a whole lot more.

Another gem of the neighborhood is the Connecticut Audubon Society, located on Burr Street at the top of the hill.  It is a nature center and wildlife sanctuary.  The center is situated on 152 acres of undisturbed natural beauty offering 7 miles of hiking trails, including the Chiboucas Wheelchair-accessible Trail, an observation platform overlooking a pond bounding with wildlife and interpretive signs.

The nature center features classrooms for educational programs, live animals on display, and nature exhibits.  The Audubon also offers outdoor exhibits of rescued birds that include owls, hawks, peregrine falcons, a turkey vulture and other raptors.   Programs are offered for youth including summer camps where children are educated on a variety of topics, with a specialty being the life of birds and their habitats.

Nestled in the heart of Greenfield Hill is the prestigious Fairfield Country Day School.  A private all boys school grades k-9.  Greenfield Hill is also home to 2 of the top elementary schools in Fairfield, Burr Elementary School and Timothy Dwight Elementary school.

Go to my Fairfield page to view other neighborhoods in Fairfield.
Neighborhoods in Fairfield

Watch here!

Links:
The Patterson Club
The Dogwood Festival
The Pumpkin Festival
Greenfield Hill Farmers Market
The CT Audubon
Fairfield Country Day School

SEARCH FAIRFIELD:

Advanced

Nestled within the serene confines of Greenfield Hill, this magnificent estate resides on a private driveway, exuding an idyllic charm that is nothing short of picturesque. Its refined interiors and expansive, park-like grounds converge to offer the epitome of luxury, seamlessly blending indoor to outdoor. The professionally landscaped 3+ acre property boasts a tennis court next to the pergola for leisurely observation, a generously sized heated gunite pool adjacent to a unique gazebo, thoughtfully equipped with comfortable seating, retractable screens, and blinds. Further enhancing the estate's allure is a children's play area, an outdoor grill boasting an authentic Tuscan pizza oven, and an expansive blue stone patio - an exquisite retreat for both relaxation and entertaining, whether with family or friends. This stately colonial residence blends classic architectural elegance with contemporary design, presenting a truly unparalleled property. Meticulously maintained, it offers over 10,000 square feet of living space, encompassing 8 bedrooms, 8 full bathrooms, and 4 partial bathrooms. The interior is adorned with 3 fireplaces, a spacious gourmet chef's kitchen, an art-deco-inspired home theater, a fully equipped gym, a billiard room, a spacious temperature-controlled wine cellar, and even a separate guest house. For car enthusiasts, a 4 car garage. This is an absolute must-see for the discerning buyer, a property that exemplifies luxury living at its finest. TAXES: $60,180 $3,998,000 Active

1610 Hillside Road Fairfield, Connecticut

8 Beds 12 Baths 10,787 SqFt 3.180 Acres

Welcome to "The Millstones" an exquisite classic revival completely transformed for today's living. Rebuilt by Cameron Clark (1923) this historic & architecturally significant home has been lovingly updated and restored by current owners. Gorgeous foyer with coffered paneling, views of the magnificent grounds and access to expansive formal living room with curved mantel fireplace, wetbar & French doors to terrace. Updated kitchen featuring Calacatta Statuario quartz countertops & backsplash, new appliances including Viking, Wolf range, 2 dishwashers, wine fridge & butlers pantry. Sunlit breakfast room w/ tumbled marble and Serena & Lily lighting. Formal dining room w/ fpl offers the perfect setting for memorable family dinners or entertaining with friends. Floor-to-ceiling French doors frame views of the gardens, terrace, pool and pond. Library w/ fireplace & builtins, WFH becomes effortless in dedicated first floor office. Playroom directly off kitchen plus large family room over the garage is perfect space for enjoying the Super Bowl with a crowd. Upstairs, the primary suite is a sanctuary unto itself, w/ marble fpl, all new master bath w/ honed Calcutta marble, steam shower,freestanding tub,WC. 2 add'l ensuite BRs + 5th BR/office located near primary bedroom. A fully renovated guest suite w/ sitting room is privately set w/ back stair access. New cedar roof, int/ext painting, Sonos. OAR is easily one of the most coveted locations to call home, conv to town, train and NYC. $2,950,000 Active

745 Old Academy Road Fairfield, Connecticut

4 Beds 7 Baths 6,686 SqFt 2 Acres

Discover your private sanctuary at the end of a serene cul-de-sac in Greenfield Hill. This country compound spans 4.5 picturesque acres, enveloping a French-inspired main house with 6 BRs, 4.2 baths, and an enchanting English garden. Step into the elegant formal living and dining rooms, both warmed by inviting FPs, setting the stage for memorable moments. The custom gourmet kitchen, designed for living, opens onto a charming stone patio—perfect for al fresco dining. The first level also houses a sun-drenched family room and sophisticated library. Ascend to discover a serene primary suite with a spacious walk-in closet and 5 additional versatile BRs. The estate further offers a unique barn featuring a gym, a squash court and extra living space—catering to every aspect of your lifestyle. Immerse in the stunning landscaping, a beautiful gunite pool, spa, private tennis court, vegetable garden, fruit trees, and stone walls outside. This bucolic haven promises a lifestyle of comfort, wellness, and charm. $2,950,000 Under Contract

125 Brett Lane Fairfield, Connecticut

6 Beds 6 Baths 4.500 Acres

Rare opportunity to own a Stunning Farmhouse Colonial on bucolic 2 plus acres in lower Greenfield Hill. Boasting POOL, SPA, BARN, GREENHOUSE & 3 CAR GARAGE WITH LOFT. Beautifully renovated with discerning custom fit & finishes. Outbuildings include original multi-purpose barn with loft, greenhouse & detached 3 car garage with finish-able loft space. Breathtaking grounds include a sweeping meadow complete with stone walls, split rail fenced property lined with established plantings, gunite pool & spa, a sport court, complete with a courtyard to entertain, barbecue, and play lawn games making this space truly exceptional for outdoor living. Open concept kitchen with french doors to stone patio overlooking the graceful property. Inviting family room with roaring fireplace & custom lacquered mill work. Living room with limestone fireplace, dry bar & library area. Light filled dining room completes the 1st floor. 2nd floor features gorgeous primary suite w/dual walk-in closets, custom cabinetry & a spa like bathroom w/soaking tub, marble shower, heated floors & dual sinks. 3 additional bedrooms including ensuite. The window lined hallway & laundry room overlooking the property is truly special. 5th bedroom or bonus room w/full bath on 3rd flr. Stroll to Greenfield Hill center with specialty shops, restaurants & pilates. Minutes to train, vibrant Fairfield center & Southport Village. Mins to beaches, town marina, golf, tennis & pickleball. Waterfront community 50 miles from NYC. $2,795,000 Active

494 Hill Farm Road Fairfield, Connecticut

5 Beds 6 Baths 3,889 SqFt 2.200 Acres

This very special offering on a Greenfield Hill cul-de-sac provides an unrivaled quality of life. Sited on 2 level acres in a sought after neighborhood, this property features a meticulously remodeled classic Connecticut colonial w/5 fireplaces that is beautifully finished on 4 floors & a great backyard for all your entertainment needs. The private oasis also includes a newer fantastic 32’ x 32’, two-story, heated post and beam entertaining barn, as well as an extensive bluestone patio set in concrete w/lighted stone walls; a screened-in porch with a vaulted ceiling & tv; and a sports court - great for pickleball, tennis, basketball. The interior is just as spectacular as the exterior. Every room offers great symmetry & lovely natural light. Features include 9-foot ceilings, hardwood flooring, newer windows & doors, extensive moldings, high-end lighting & custom window treatments. The gourmet kitchen features custom cabinetry, an oversized center island, upscale appliances (Wolf, SubZero, Bosch), 2 dishwashers, beverage drawers, a floor-to-ceiling fireplace, a sitting area & dramatic vaulted ceiling w/ antique wood beams. The primary suite is sumptuous, rivaling one in a 5-star hotel. Every bathroom is updated using marble & quality and timeless cabinetry, lighting, and fixtures. The 3rd fl is also finished & features a private home office. The lower level features a gym, entertaining area, workshop & storage areas. Au pair or guest suite. Generator. $1.5 mmm in updates. $2,399,000 Under Contract - Continue to Show

212 Coventry Lane Fairfield, Connecticut

5 Beds 4 Baths 4,064 SqFt 2 Acres

Set back graciously from the road, this newer construction home designed by award-winning local architect Jack Franzen, is an opportunity that buyers will quickly fall in love with. Every box is checked with all this home has to offer; eat-in chef’s kitchen, expansive first floor living spaces, luxurious master suite, EVERY bedroom provides an en-suite bath and walk-in closets, walk-out lower level providing many opportunities depending on your needs, bluestone patio enclosed by glass railings overlooking your private 2 acres. Possible pool site. 999 Merwins is located in the desirable Greenfield Hill section of Fairfield providing homeowners with total privacy yet convenience to all. Come experience turn-key Fairfield living at its very best. $1,899,000 Under Contract - Continue to Show

999 Merwins Lane Fairfield, Connecticut

6 Beds 8 Baths 4,449 SqFt 2.070 Acres

Welcome to the magnificent 280 Fair Oak Drive, an exceptional residence within the prestigious Greenfield Hill neighborhood. Prepare to be captivated by this splendid property, with an impressive 8,126 total SF of living space on a sprawling 2.27 acre parcel. Come into an exquisitely designed floor plan that showcases 4 generously proportioned bedrooms, including an expansive primary suite w/gas FP, and 3 full and 3 half impeccably appointed bathrooms. The epicenter of this stunning home is a gourmet kitchen w/premium appliances including Sub-Zero refrigerator and Viking range, tailored to satisfy the most discerning culinary tastes. Abundant natural light pours through expansive windows, imbuing the living areas with an inviting ambiance that beckons one to linger. The 2nd floor Great Room could be used for a potential in-law or au-pair suite & the fully finished lower level offers a media room, workout area & large living area that could accommodate a wine cellar. The spacious attic can be finished to suit. Thoughtfully curated outdoor spaces are perfect for entertaining, & include a serene patio with outdoor fireplace, TV, grilling area, and meticulously landscaped grounds. Buyers will relish the convenience of nearby boutiques & acclaimed dining establishments. Pristine beaches and picturesque parks further enhance the desirability of this community. Do not miss the opportunity to realize your ideal lifestyle. Arrange a viewing today! $1,899,000 Under Contract

280 Fair Oak Drive Fairfield, Connecticut

4 Beds 6 Baths 5,622 SqFt 2.270 Acres

This stunning one-of-a-kind home is perfectly situated on a level professionally landscaped lot in the sought after Ridge Community. The Ridge is conveniently located on the Fairfield Westport Line offers 24 hour gated piece of mind, heated pool, tennis courts, sports court, club house, playground & much more. This special offering boasts an open floor plan w/ loads of light, soaring ceilings, & generously sized rooms. Elegant formal areas, large EIK, and a jaw dropping great room can be found on the first floor. The serene Primary Suite is located on the main floor with large primary bath, walk in closets, cathedral ceiling & stone fireplace. A circular staircase leads to bonus room which is a great gym or home office option. The second floor offers 3 bedrooms, 2 full baths and a study area. A large rec room can be found in the lower level alongside a massive amount of storage. Additional features of the main house include extensive custom moldings, hardwood floors throughout, plenty of closet & storage space, generator, separate laundry room, 2 half baths, large mudroom & 3 car attached garage. For the car enthusiast, the detached structure offers an additional 3 car garage along with finished 864 SF space above perfect for an art studio, private office or in law option. Total SF 5070 - This home is an entertainers dream w/ walls of windows & doors that open to the stone patio overlooking the beautiful backyard. Be in for the holidays! $1,799,900 Under Contract - Continue to Show

200 Fence Row Drive Fairfield, Connecticut

4 Beds 5 Baths 4,206 SqFt 2.030 Acres

One of a Kind Renovated Barn for Sale or Rent. State of the Art Updates w/ Authentic Barn Beams, Wide Plank Oakwood Flrs, Stone Fireplace, & Iron Railings. Oversized Windows on rear of the house that lookout onto a Babbling Brook, Stone Walls & 60 Acres of Open Space. Open Floor Plan Kit/Family Rm/Dining rm look out to Large Slate Patio, perfect for Family Living, Awesome Entertaining, or Peaceful Relaxation. Kit w/Stone Backsplash, Hardwood Flrs, Large Island w/Seating, Stainless Steel Appls, Walk in Pantry, & Granite Countertops. Formal Living Rm w/Wood Beams, Iron Railings, & Oversized Windows. Primary Bedrm w/new Antique Plank Pine Flring & Stunning Views is a Tranquil Oasis. Newly renovated Primary Bath w/Double Sinks, Soaking Tub, Glass Shower, & Radiant Heated Flrs. Three other Spacious Bedrms w/Extras, One w/Sitting Rm, Large Closets, & Private Full Bath. The other two share a Roomy Jack & Jill Bath, each w/their own Walk-in Closets. A Large Flex Space on the Upper Level Boasts French Doors to a Balcony. Used now as a Gym, you can workout looking over the 60 Acres of Open Space Land and Pastures while listening to the Babbling Brook. This Room would also work for Office, Playroom, Gym, Game Room and large enough to be a combination of any of the above. This home also has it's own Laundry Room, an Office Area, and a Morning Coffee or Reading Nook. Outside is Beautifully Landscaped, Backyard is completely & newly fenced (deer fencing and split rail fence by gardens). $1,795,000 Under Contract

1446 Cross Highway Fairfield, Connecticut

4 Beds 5 Baths 3,891 SqFt 2.040 Acres

Designed to be luxurious as well as functional, this center hall colonial situated on over 3 acres with golf course views exudes a casual elegance sought after by today's families. The combination of the awe-inspiring two-story entry foyer, the formal living room with fireplace, the dining room that easily accommodates large gatherings, the spacious modern eat-in kitchen, the family room with a stone fireplace, and the expansive master bedroom suite creates a sense of sophistication without sacrificing practicality. The kitchen and family room both open to a large bluestone patio which is surrounded by a generous yard and a wooded backdrop. Additional features of this spacious home include four additional bedrooms, two with en suite, first floor office, hardwood floors with mahogany inlay, finished lower level, walk-up attic for storage, three-car garage, and whole house generator. Conveniently located to the Merritt parkway, shops, and schools. $1,749,000 Active

120 Hoydens Lane Fairfield, Connecticut

5 Beds 6 Baths 4,445 SqFt 3.070 Acres

This Enchanting Circa 1915 Fairytale Country House Is Privately Sited At The End Of A Long Tree Lined Gated Drive On Four Landscaped Acres In Bucolic Greenfield Hill. Charming Exterior & Interior Architectural Details Include Multiple Fireplaces, Wood Shingle Roof, Copper Gutters, Brick Lined Walkways, Paneled Walls and Coffered Ceilings. Through A Marble Floored Foyer With Powder Room, Guests Enter A Stunning Living Room Featuring Paneled Walls, Picture Windows, Fireplace And Beamed Ceiling. Entered By French Doors From The Living Room Is A Cozy Den Which Also Features A Picture Window With Pond Views, Fireplace, Coffered Ceiling And Built Ins. Adjoining The Den Is A Screened Porch With Access To A Raised Terrace Overlooking The Spectacular Grounds. A Family Room With Vaulted Ceiling Also Accesses The Private Terrace. Both Formal And Casual Dining Is Enjoyed In The Elegant Dining Room With Built Ins And Adjoining Butler's Pantry. The True "Country Kitchen" Offers A Fireplace, Carrara Marble Countertops, Chef Grade Appliances And Breakfast Bar. The Second Floor Primary Suite With Fireplace And Luxury Marble Trimmed Bath Offers A Private Balcony With Sweeping Property Views. Two Additional Bedrooms And Full Bath Complete The Second Floor. The Fourth Bedroom With Full Bath Occupies Its Own Space On The Third Floor. Adjacent Two Acre Lot (5425 Congress St.) Also Available. $1,595,000 Under Contract

5415 Congress Street Fairfield, Connecticut

4 Beds 4 Baths 3,186 SqFt 4 Acres

Welcome to this Beautiful Classic Colonial Situated On 2 Level Acres in a quiet neighborhood in Greenfield Hill. Enjoy this 4 bed 2 ? Bathroom home with spacious rooms and seamless flow all creating the perfect space for family gatherings and memorable entertaining. With its spacious front to back Livingroom and the kitchen that opens to the dining room, Family room and solarium, as well as a finished basement, this home has an abundant amount of space. Not to leave out the apartment with its own separate entrance complete with Living room, kitchen, bedroom and full bath perfect for guests and in-laws. This home has been meticulously maintained and cared for with many updates as well as a Full house generator! Commune with nature in this two acre setting complete with Barn, Vegetable Garden, 3 car garage surrounded by mature professional landscaping – a truly bucolic setting. Only minutes from Fairfield’s vibrant town center, Southport Village, restaurants, and trains for an easy commute. $1,439,900 Under Contract

90 Shetland Road Fairfield, Connecticut

5 Beds 4 Baths 3,247 SqFt 2.010 Acres

Exceptional opportunity to own this sprawling Contemporary home in the Greenfield Hill neighborhood of Fairfield, on the border of Westport. It has the amenities and school system of Fairfield and a Westport mailing address. Sited beautifully on 2.44 acres of rolling lawns and specimen plantings, this private setting offers two intimate Patios, a screened Porch, and an expansive Deck overlooking the inground pool for Summer enjoyment. The floorplan easily accommodates a large or multi-generational family, providing abundant space for all. Over 6,200 square feet on two floors, this home features a Primary Bedroom Suite complete with either Sitting Room or Nursery and an En-Suite Bath with heated floors. There are 3 more comfortable Bedrooms, each with an En-Suite Bath, and 2 Half Baths one on each floor. The floorplan offers flexibility to adapt to the new Owner's needs. It has been meticulously maintained and updated over time and includes all new windows throughout. Hosting large gatherings is easy with the Eat-in Kitchen flowing into the Family Room, Living Room, and Pool area. There is an abundance of storage closets throughout the home, a 3-Car Garage with an extra bay for storage or other uses such as boating or sports equipment. Additional amenities enhance the lifestyle here, featuring an elevator for added accessibility, central air for comfort, a generator for peace of mind, and a chair lift along the rear stairwell. This special property is not to be missed! $1,379,000 Under Contract - Continue to Show

3080 Sturges Highway Fairfield, Connecticut

4 Beds 6 Baths 4,204 SqFt 2.440 Acres

Nestled on a charming Greenfield Hill cul-de-sac sits this spacious 4-bedroom Colonial on 2 acres. Surrounded by privacy landscaping, this home boasts an expansive deck with a pergola, firepit, and a large yard perfect for entertaining and outdoor activities. The gracious front-to-back Living Room with fireplace and formal Dining Room off the welcoming foyer anchor the main level. An Eat-In Kitchen overlooking the backyard and a Family Room with a fireplace, built-ins, and a wet bar are perfect everyday gathering places. Enter from the 2-car garage or deck into the Mudroom with plenty of storage and laundry room. The Primary Bedroom and full bath with a Bonus Room offers many possibilities--home office, gym, media room, nursery, or exquisite dressing room. 3 additional bedrooms, each with generous closets, and a recently updated full bath upstairs. The lower level with 3 separate rooms and a huge storage area is perfect for TV, music, or a craft area. This well-maintained home with hardwood floors throughout (except bonus room) includes a full house generator, 6 zones, and an insulated pull down attic. Seemingly a million miles away, just a few minutes to train, shopping, restaurants, schools, highways or one of Fairfield's 5 beaches $987,000 Under Contract

85 Whiting Pond Road Fairfield, Connecticut

4 Beds 3 Baths 3,286 SqFt 2.020 Acres

This is an amazing opportunity to purchase a home in a much sought after, multimillion dollar neighborhood on 1.93 acres for under $1 million! The house is located in the heart of Greenfield Hill, Fairfield's estate area & has over 3,400 sq ft of finished space on 3 levels. The breathtaking, tree top views from many rooms offer serenity and privacy! This spacious contemporary has 3-4 bedrooms, 3 1/2 baths, & an open floor plan. The recently renovated 1,000 sq ft, walk out, garden level great room has a full bath, a small office & a walk-in cedar closet. This level also has an open floor plan, entertainment center, wet bar/copper sink & wine refrigerator. This level, with it's separate exterior entry, would make a great in-law suite! Owners upgraded their heating system by adding a high efficiency heat pump. This keeps their heating & cooling costs lower than average for a house this size. The main level has 3 bedrooms, 2 baths & a den w/closet that could be a 4th bedroom. Two of the 3 main bedrooms have wall to wall sliders to the huge deck. The entire upper level has a vaulted ceiling, beams, an open floor plan & walls of sliders to another huge deck. the living room & dining room share a brick, floor to ceiling open fireplace. With a little updating, this home provides the extraordinary opportunity to create a true contemporary masterpiece, worthy of its prime location. House is being sold "AS IS". $919,000 Under Contract

485 Greenfield Hill Road Fairfield, Connecticut

3 Beds 4 Baths 2,400 SqFt 1.930 Acres

What Is Your Home Worth?