Woodbury Connecticut
Homes for Sale and Real Estate

Area Description

Woodbury is often referred to as the “Antiques Mecca of New England,” due to the volume of dealers lining Main Street North and South, as well as many side streets.

Located in the southern sector of Litchfield County, it lies in the Pomperaug River Valley. The Pomperaug River is a tributary of the Housatonic River and is fed by the Nonnewaug and Weekeepeemee Rivers. It’s principal boroughs are Hotchkissville, Minortown, Neufa, North Woodbury, Pomperaug and Woodbury Center, encompassing a total area of close to 37 square-miles.

Area Highlights

The Neighbors

Friendly and community-oriented


Woodbury is a distinctive New England town owing to its carefully placed historic homes along its main thoroughfare, stretching well over a mile.


Woodbury is an eclectic mix of old dotted with new, rural mixed with contemporary, and has a charm all its own.

You'll Love

All essentials in town, including restaurants, markets and commercial establishments maintaining their own against the backdrop of Woodbury’s Colonial and Victorian charm.

Perfect For

Families, empty-nesters, and everyone in between.

Around the Area

Several buildings are on the National Register Historic Districts and include the Old Town Hall, United Methodist Church and  North Congregational Church. The Masonic Temple is, perhaps, the most striking building along Main Street. The Greek Revival building sits atop a modest cliff, and is accessed by switchback set of stairs. A driveway was later put at the rear of the building, but harks back to Grecian times with its formal architecture.

Woodbury’s founders were settlers originally from Stratford, followed by a second group given permission to purchase land from Native Americans. These founding families established the Pomperaug Plantation in 1673. Soon, Woodbury developed into a thriving agricultural community, rich with artisans and tradesman, transforming into the quiet, residential area that it is today.

One of the most iconic businesses in the center of town is Canfield Corner Pharmacy, a true compounding drug store and apothecary, of uncertain, but genuinely antique vintage. Woodbury’s other unique venues and features are the Glebe House, home of historic landscape architect Gertrude Jekyll, the Hotchkissville Historic district, and St. Paul’s Episcopal Church, along with Flanders Nature Center, rolling hills, pastures and more.

Several notable people have lived in Woodbury, including: Leroy Anderson who wrote “Sleigh Ride,” A Christmas classic; notable musicians such as jazz guitarist Joe Beck; musician and director Rob Zombie; several surreal and traditional painters, and a smattering of politicians.



Area Map

Area Listings