$1,753,153Average Value$510Average Price per Sq Ft11Homes For Sale
Nature-filled suburb with a historic village center
Situated in the Fairfield County suburbs is Greenfield Hill, a residential neighborhood with a small historic village center. The area is part of the original center of the town of Fairfield, with its 18th-century congregational church and saltbox structures, and acres of natural land and secluded single-family homes give it a countryside feel. Locals can shop at boutique stores and local food markets scattered throughout the area, and easily access nearby highways and urban centers. Students here are served by Fairfield Public Schools, which receives an overall A rating from Niche. Greenfield Hill has an overall CAP Index crime score of 1 out of 10, significantly lower than the national average of 4.
The Corner Market & Sandwich Shop in Greenfield Hill serves up delectable treats.
Coreen's Bridge Flower Shop in Greenfield Hill provides gift options and custom arrangements.
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Colonial styles on scenic countryside roads
In the area surrounding Greenfield Hill’s historic village, residents can find roads lined with towering dogwood trees and midcentury single-family homes. “It’s mostly colonial homes on large parcels of land – most houses are on two acre or more lots," says Andrea Viscuso, a local Realtor and team leader of the Forte Team at Compass. “There are a lot of trees, really nice landscaping, and the country roads make for beautiful drives.” Other common home styles include split-level residences and newer 21st-century builds with traditional-style architecture. Most properties also include paved driveways and have garages. Single-family properties in Greenfield Hill typically range from $1 million to about $4 million, although there are a handful of outliers for less than $1 million.
Samp Mortar Reservoir is a large body of water bordering Greenfield Hill.
There are waterfront homes on the picturesque Samp Mortar Reservoir in Greenfield Hill.
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High marks for Fairfield Public Schools
According to Viscuso, young learners in Greenfield Hill attend one of two primary schools: Dwight Elementary or Burr Elementary School, both rated A by Niche. Older students might head to A-rated Fairfield Woods Middle School and the A-plus-rated Fairfield Warde High School. With a 98% graduation rate and a variety of college prep resources, Fairfield Warde is ranked No. 11 on Niche’s 2025 “Best Public High Schools in Connecticut” list. Students can also attend a handful of nearby private schools, including Fairfield Country Day School (FCDS), located in the Greenfield Hill historic village area and rated A-plus. Founded in 1936, FCDS is an all-boys institution for kindergarten through ninth-grade students. The Fairfield Public Library offers a variety of weekly afterschool programming for all students in kindergarten through eighth grade; programs for elementary school children are popular and usually fill up.
Nestled in the heart of Greenfield Hill, Timothy Dwight is a Blue Ribbon School in Fairfield.
Fairfield Warde High School in Fairfield serves students in grades 9th through 12th.
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Wildlife conservation at Connecticut Audubon Society
More than 1,000 acres of natural open space are owned by the town of Fairfield; in Greenfield Hill, residents can head to Mountain Laurel Open Space and the Brett Woods Conservation Area for scenic hiking trails. The nearby Samp Mortar Reservoir is dotted with several private beaches for people living nearby, and Greenfield Hill also encompasses the Connecticut Audubon Society, a nonprofit organization with a wildlife sanctuary and conservation area spanning more than 150 acres. “The Connecticut Audubon Society hosts summer camps and other year-round programs,” Viscuso says. She adds that residents also often go to the Patterson Club, a private country club where members can access an 18-hole golf course, a 25-meter swimming pool and a racquet sports complex. Towards the northern end of the neighborhood is the H. Smith Richardson Golf Course, which also has an 18-hole layout and offers discounted rates for Fairfield residents.
Greenfield Hill has charming touches around every corner.
Take a hike in Mountain Laurel Open Space in Greenfield Hill.
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Local shopping and dining at Greenfield Hill Commons
Greenfield Hill Commons is a small shopping center where merchants do business out of a one-story brick building. “Greenfield Hill Commons has some stores; there’s a chocolate shop, home décor store, a yoga studio… it’s kind of like a mini downtown,” Viscuso says. “And there’s a coffee shop with a deli that also sells vegetables and fresh produce, so it’s more like a little market.” Also in Greenfield Hill Commons is BONDA Restaurant, an upscale dining spot that serves popular pasta and chicken dishes. For fresh local food, residents can head to Little River Farm, a small neighborhood farm with a seasonal market stand that sells produce, eggs and firewood. More extensive grocery shopping can be done at the nearby Trader Joe’s or ShopRite of Fairfield, both in retail centers along the Black Rock Turnpike.
Trader Joe's is Greenfield Hill's go-to for high quality bargain shopping.
Country Cow Deli is Greenfield Hill's closest lunch option.
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Arts and crafts at the annual Dogwood Festival
Viscuso says that a number of community events happen year-round in Greenfield Hill, including the Dogwood Festival and a farmers’ market. During Mother’s Day weekend, the annual Dogwood Festival features regional vendors that host arts and crafts activities and sell artisan goods. Festival attendees can also enjoy food trucks, live music and guided walking tours about the area’s history. Every Saturday from May through October, the Greenfield Farmers Market takes place at the Greenfield Hill Commons.
Convenient access to the Merritt Parkway
Greenfield Hill is suburban, so its access to public transit is limited. Most people use their personal cars to drive around. “People can use the back roads here to go really anywhere, but we also have easy access to Merritt Parkway and Interstate 95,” Viscuso says. The Merritt Parkway, or Route 15, runs diagonally through the center of Greenfield Hill. To access Interstate 95, residents can drive approximately 3.5 miles into the city of Fairfield. Commuters can take the Metro-North train into New York City from the Fairfield station, 3 miles away. The Westchester County Airport is a 30-mile drive away and offers connecting flights to several domestic airport hubs in major cities like Chicago, Miami and Washington, D.C.
GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
View GreatSchools Rating Methodology
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Crime and Safety
1 - Low Crime, 10 - High Crime
Greenfield Hill
US
Homicide
1
4
Sexual Assault
1
4
Assault with Weapon
1
4
Robbery
1
4
Burglary
2
4
Motor Vehicle Theft
1
4
Larceny
1
4
Crime Score
1
4
Source: WhatIsMyCrimeRisk.com
Greenfield Hill Demographics and Home Trends
On average, homes in Greenfield Hill, Fairfield sell after 60 days on the market compared to the national average of 55 days. The median sale price for homes in Greenfield Hill, Fairfield over the last 12 months is $1,600,000, up 3% from the median home sale price over the previous 12 months.
Enchanting countrystyle retreat offering the warmth of a welcoming neighborhood with the luxury of natural privacy, nestled amid professionally landscaped gardens and mature trees. Designed for gracious living and effortless entertaining, 165 Hemlock Hills S blends refined upgrades with modern comfort throughout. Featuring two primary suites, five bedrooms, and four beautifully renovated baths,
3808 Redding Road is the kind of property that feels discovered rather than found. A place where time has softened the edges, and the landscape tells its own story. Dating to 1769 and set on nearly eighteen acres of open fields and mature trees, this is one of Fairfield's earliest homes, thoughtfully rebuilt in 2008 to preserve its character with modern ease. Inside, the home unfolds with warmth
Greenfield Hill proposed new construction on a 2.65-acre lot along a Town-designated Scenic Road, to be built by award-winning design-builder Bonnie Paige in collaboration with Vicente Burin Architects. The proposed residence is based on a design sold in Southport Village; interested buyers may tour similar homes and meet the team to tailor plans, finishes, and timeline. The property sits among
27+ acres of serene land along the Aspetuck River spreading between Fairfield and Weston. (7 acres in Fairfield). A rare opportunity to build your dream home and have seclusion while bordering Westport with all modern day conveniences and shopping. Close to Aspetuck Valley Country Club and golf course, The Patterson Club, Camp Aspetuck and the Connecticut Audubon Society. *All parcels sold
New Construction of a farm house style colonial in the prestigious Greenfield Hill section of Fairfield. Approvals in place for this home on a designated scenic road. 193 feet of frontage plus city water available in the street. This is an excellent opportunity to customize your dream home on a beautiful, cleared and leveled Greenfield Hill lot surrounded by nature, charming New England stone
Set within The Ridge in Greenfield Hill, Fairfield's gated residential community, this residence originally designed by renowned architect Bill Blanski has been completely rebuilt and thoughtfully reimagined with the scale and finish of new construction. Spanning over 7,500 square feet, the home offers four bedrooms and six full and two half baths, with wide plank oak floors, multiple fireplaces,
The Ultimate East Coast Sanctuary-Where Privacy Meets Pinnacle Luxury. Surrounded by high stone walls, a fortress of modern architecture is engineered for the world's most discerning icons who demand seclusion with proximity to NYC. This 38.91-acre compound ,is the mid century former home of Richard Rodgers, composer of The Sound of Music. Restored and expanded to incorporate 7 bedrooms and 7
Eight minutes from downtown Westport, escape to 11 Judges Hollow-a 1930's rustic hunting cabin on 1.6 private wooded acres at the end of a long secluded driveway. A one of a kind private in holding completely surrounded by the 180 acre Brett Woods Conservation Area, this rare property offers ultimate privacy with protected open space as your permanent neighbor. Judges Hollow is nestled within
In the heart of Greenfield Hill proper at the top of Bronson Road, this special and truly unique estate presents a rare opportunity in one of Fairfield's most coveted locations. Set on just over two acres of beautifully landscaped, professionally photographed grounds, the property reflects a timeless elegance that would be costly to replicate today. Across from a distinguished equestrian family
A special property with pool & tennis court, on the Westport border, minutes to shops, restaurants and train. Experience refined luxury in this picturesque setting, situated back from the road down a long, lighted driveway, winding past a serene pond. Nearly 4000 sq ft with 4 bedrooms & 4.5 baths, this open floor plan home features city water, sewer, natural gas, oil heat and central A/C for
Set within artisan stone walls with curated flowering landscapes, this magnificent stone and stucco residence is a masterful tribute to Southport's enduring architectural legacy. Designed to blend seamlessly among the grand neighboring estates of this coveted enclave, 688 Hulls Farm strikes a rare balance: modern in execution, timeless in presence. Construction begins in April with Coastal Luxury
Rolling Hills Drive is the kind of street where homes feel settled into their surroundings, quiet and residential, with attractive homes lining the neighborhood and nature close at hand. Just moments from hiking trails, Lake Mohegan, and Smith Richardson Golf Course, it's a setting that offers both neighborhood connection and easy access to the outdoors. At 126, a classic Colonial sits gracefully
Fairfield/Easton line. Historic charm meets modern comfort with this quaint country-style cottage, (formally The Old Wilson's Mill) located in the desirable Greenfield Hill section of Fairfield right off exit 27/Merritt Pkwy less than a 50 min drive to NY. Minutes from Fairfield's Business District, retail, restaurants, banks and healthcare providers. This vintage standalone 7 room cottage,
Available August 1- September 5: Fully Furnished. You'll never want to leave 'Splendido Manor', an iconic estate perfect for the sophisticated and active lifestyle. This sprawling 4-acre compound nestled in the heart of Greenfield Hill has all of the amenities of an idyllic retreat. With 5 bedrooms, a separate one-bedroom guest cottage, a lighted Sport/Tennis Court, a 1900 SF Indoor/Outdoor Pool
Beautifully updated FURNISHED colonial in Greenfield Hill. Designers own home. A gorgeous entry foyer greets you & opens to a large living room with cathedral ceilings, fireplace & large picture window.Continue into an absolutely fabulous, sun-filled eat-in kitchen w/ full dining area, large island for entertaining, a cozy window seat and sliders which lead to a spacious deck, gorgeous & very
Summer, winter, short term or annual rental available. Enjoy this expanded & renovated modern farmhouse, newly painted and elegantly decorated with a sunny open floor plan. Newly white washed oak floors on each level makes the house very bright. A spacious and fully equipped kitchen offers top of the line appliances, a big center island, loads of cabinetry and eat-in kitchen option. Soaring
Surrounded by stone walls, this one-of-a-kind, spectacular and private 36-acre Greenfield Hill country compound has had a stunning top-level transformation, creating a breathtaking Fairfield County estate like no other. The storied former home of Richard Rodgers, composer of The Sound of Music, the mid-century main residence was restored and expanded to incorporate 7 bedrooms and 7 full baths,
Available January through May 2026. You'll never want to leave 'Splendido Manor,' an iconic estate perfect for a sophisticated, active lifestyle. This sprawling 4-acre compound in the heart of Greenfield Hill has all the amenities of an idyllic retreat. It has something for everybody with five bedrooms, a separate one-bedroom guest cottage, a lighted Sports/Tennis Court, a 1900 SF Indoor/Outdoor
Local Logic measures the walkability, access to public transit and bikeability of any address. CAP Index provides objective, accurate, and consistent data to help measure, compare, and mitigate crime risks.
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. Our sources include: Accuweather, Public Records and Neustar. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
