Greenfield Hill Homes for Sale
Greenfield Hill is the inland, northern corner of Fairfield: a village green, a historic district around it, and large wooded parcels for most of the rest. It is the part of town furthest in character from the shoreline, and buyers usually arrive here having already decided they want land rather than a walk to the beach.
Available homes in Greenfield Hill
These are active SmartMLS listings in the town of Fairfield whose neighborhood field reads Greenfield Hill. The field is filled in by the listing agent, so a Greenfield Hill home left untagged will not appear here — treat this as a reliable sample of what is on the market, not a complete census of it.
$9,975,000
4800 Congress, Fairfield, CT 06824
7 bd · 8.5 ba · 9,129 sq ft
Listed by William Pitt Sotheby's Int'l — Leslie Razook
$5,975,000
590 Sturges, Fairfield, CT 06824
6 bd · 7.5 ba · 8,900 sq ft
Listed by Higgins Group Real Estate — Julie Vanderblue
$3,988,000
475 Fence Row, Fairfield, CT 06824
4 bd · 5 ba · 7,971 sq ft
Listed by The Agency — Erin Melson
$2,799,900
221 Farmstead Hill, Fairfield, CT 06824
5 bd · 4.5 ba · 6,616 sq ft
Listed by William Raveis Real Estate — Denise Walsh
$2,695,000
443 Brambley Hedge, Fairfield, CT 06824
4 bd · 6 ba · 7,298 sq ft
Listed by William Pitt Sotheby's Int'l — Paul Triantafel
$2,690,000
1074 Sturges, Fairfield, CT 06824
5 bd · 4 ba · 4,540 sq ft
Listed by Compass Connecticut, LLC — Amy Desel
$2,300,000
18 Merry Meet, Fairfield, CT 06824
4 bd · 7 ba · 3,883 sq ft
Listed by Giner Real Estate — Peter Giner
$2,195,000
2493 Redding, Fairfield, CT 06824
5 bd · 5 ba · 5,415 sq ft
Listed by Compass Connecticut, LLC — John Foran
$1,785,000
203 Wildflower, Fairfield, CT 06824
5 bd · 5 ba · 6,136 sq ft
Listed by Realty ONE Group Connect — Danielle Baleeiro
$1,700,000
220 Stonewall, Fairfield, CT 06824
5 bd · 3.5 ba · 4,845 sq ft
Listed by Coldwell Banker Realty — Julie Walsh
$1,695,000
140 Labbance, Fairfield, CT 06824
3 bd · 2.5 ba · 3,649 sq ft
Listed by Higgins Group Bedford Square — Honey Blank
$1,599,000
88 Springer, Fairfield, CT 06824
4 bd · 2.5 ba · 3,421 sq ft
Listed by Coldwell Banker Realty — Carrie Sakey
Where Greenfield Hill actually is
The neighborhood sits in the north of Fairfield, roughly bounded by the Easton town line to the north, Burr Street and the northern end of Black Rock Turnpike to the east, and Southport and Westport to the south and west. It is unincorporated — part of the town of Fairfield, with no separate government.
This is worth stating plainly because national listing portals handle Greenfield Hill badly. Some file its listings under other place names entirely, and the boundary they draw is not always the one residents use. The search on this page is scoped to the town of Fairfield and the Greenfield Hill neighborhood as SmartMLS records it.
The green and the historic district
The Greenfield Hill Historic District was listed on the National Register of Historic Places on 11 March 1971 (reference 71000899) and covers about 175 acres. It centres on the triangular green bounded by Hillside Road, Old Academy Road and Bronson Road, then extends south in an irregular shape; newer property north of the green is excluded. The listing records 38 principal houses or structures, 20 secondary structures and a windmill.
The district is partly overseen by Fairfield’s Historic District Commission. As with Southport, if you are buying near the green and plan exterior work, check with the town what review applies to that address rather than assuming.
Housing styles
Inside the district the houses run from the eighteenth to the mid-nineteenth century in a mix of styles rather than one dominant form — saltboxes and gambrel-roofed houses among them. Away from the green the neighborhood is mostly later, on noticeably larger parcels than the rest of Fairfield, which is what produces the rural feel people describe.
Lot sizes here are governed by Fairfield’s zoning for the area. Published summaries disagree on the exact minimum, so confirm the zone and its requirement for any specific parcel with the town before relying on it — particularly if you intend to subdivide or add an accessory structure.
The church, the academy and the dogwoods
Greenfield Hill Congregational Church presides over the green and is the neighborhood’s best-known landmark. Timothy Dwight became its minister in 1783 and founded an academy here — the site is now Timothy Dwight Park — before going on to the presidency of Yale.
The Dogwood Festival on the green each spring is the fixed point in the neighborhood’s calendar, timed to the bloom. If you are house-hunting here in late spring, it is worth seeing the area during it and also outside it: the traffic pattern on festival weekend is not the ordinary one.
Sources
Historic-district boundaries and review requirements change. Confirm what applies to a specific address with the Town of Fairfield before relying on anything here.
Looking at Greenfield Hill?
Michael Derikrava works across Fairfield and can tell you how Greenfield Hill compares with the rest of the town for what you are after.
- Search Greenfield Hill homes
- Talk to Michael Derikrava about buying here
- Get a valuation for a Greenfield Hill home
- Selling in Greenfield Hill
Other Fairfield neighborhoods
© SmartMLS. All rights reserved. Information is deemed reliable but is not guaranteed accurate by SmartMLS. Listing data is provided for consumers' personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All properties are subject to prior sale, change, or withdrawal.