Woodbury Real Estate

Woodbury, CT Homes for Sale

Woodbury, CT homes for sale generally range from $325,000 for smaller capes to well over $900,000 for restored antique colonials, with the median sitting near $450,000. Dave Jones Realty has tracked this Litchfield County market for years, guiding buyers through a housing stock that mixes 18th-century farmhouses along Main Street South with newer construction off Route 6. Located about 35 minutes from Waterbury and roughly 90 minutes from New York City, Woodbury draws buyers who want historic New England character, larger wooded lots, and access to the town's well-known antique district.

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Home Styles and Price Context

Woodbury's housing stock centers on antique colonials and center-chimney capes, many built between 1740 and 1830, that typically list between $500,000 and $950,000 depending on restoration. Mid-20th-century ranches and raised ranches in Woodbury range from $325,000 to $475,000. Lot sizes are generous, with many properties on one to three acres due to residential zoning requirements. Newer colonials built after 1990 near Route 6 generally list between $550,000 and $800,000.

Neighborhoods

Main Street South Historic District

The Main Street South corridor holds Woodbury's oldest homes, many dating to the 1700s and interspersed with the antique shops that give the town its reputation as the antiques capital of Connecticut. Homes here command premiums for period detail and walkability to the town center.

Middle Quarter and Route 6 Area

The Middle Quarter section along Route 6 combines commercial convenience with residential streets holding capes and colonials priced from $400,000 to $650,000. Buyers choose this area for quick access to shopping and shorter commutes toward Southbury and Interstate 84.

Daily Life

Woodbury students attend Region 14 schools, including Nonnewaug High School, which serves both Woodbury and Bethlehem. Hollow Park on Hollow Road offers ballfields, tennis courts, and a swimming pond used through the summer. Commuters reach Interstate 84 in Southbury in about 15 minutes, connecting to Waterbury and Danbury employment centers. The Flanders Nature Center provides trails and preserved farmland on the town's west side.

Working With a Local Agent

Dave Jones Realty has handled transactions across Woodbury's historic district and its newer Route 6 developments, giving buyers direct comparison points between antique properties and modern construction.

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Newest Homes for Sale in Woodbury, CT

$699,900
3 Beds ⋅ 3 Baths ⋅ 24204212 MLS
Imagine starting your morning with a cup of coffee on the gorgeous wraparound front porch as you take in the view of Radey Pond or spending warm summer evenings entertaining family and friends in this beautiful and private setting.Situated on 2.31 acres, this charming 3/4-bedroom, 2.5-bath Cape/Colonial offers the perfect combination of classic New England character, comfortable living space, and a flexible floor plan. At the heart of the home is the spacious eat-in kitchen, offering plenty of counter and cabinet space and flowing naturally into the inviting family room with a cozy fireplace. Whether you're entertaining a crowd or enjoying a quiet evening at home, this warm and welcoming space is made for gathering.A separate living room and office/den provide additional options for relaxing, working from home, or creating a space that fits your lifestyle.Upstairs, the spacious primary suite is a true retreat with a large closet and private full bath featuring a spa tub and separate shower. Two additional generously sized bedrooms share another well-appointed full bathroom.Need even more room? The finished third floor offers wonderful flexibility and can easily become a fourth bedroom, private home office. Hardwood floors throughout add timeless appeal, while a new roof offers peace of mind.Outside, the 2.31-acre private lot and beautiful pond views create a setting that feels removed from it all, while still being conveniently located near amenities, and major highways

201 Transylvania Rd, Woodbury
$699,900
4 Beds ⋅ 3 Baths ⋅ 24165323 MLS
Watch the parade from your front yard, walk to school, walk to the excellent restaurants in town, walk to the library and to the local park and market! Fabulous location! One of Woodbury's last remaining homes built in the late 1600s. This charming residence offers a unique blend of historic character and modern convenience, ideally situated for those who appreciate easy access to local shops, parks, and restaurants. The interior of the home boasts a rich history with exposed wooden beams, 4 fireplaces, and classic hardwood floors, creating an inviting and warm atmosphere. Outside, a private patio with an open fireplace provides an ideal setting for relaxation or entertaining, surrounded by lush perennial gardens. Adding to the property's versatility is a separate guest house. This additional structure is perfect for an artist's studio, offering a quiet and inspiring space for creative pursuits, or it can serve as a professional office. Woodbury is known for its historical properties, with some homes dating back to the late 17th century. Main Street offers a charming experience with its antique shops, local restaurants, and vibrant Memorial Day parades. Woodbury is known for its picturesque downtown area, featuring beautiful streets and historic houses. Litchfield Hills are home to numerous wineries, forming part of Connecticut's Wine Trail,where you can enjoy tastings and scenic vineyards. The region also boasts farm-to-table restaurants that highlight local produce

339 Main St S, Woodbury
$699,000
3 Beds ⋅ 3 Baths ⋅ 24200785 MLS
Some homes make their impression at the front door. This one begins long before it. Set nearly out of sight on almost three acres, the home is approached by a long driveway that opens to a circular drive and generous garage parking, a gracious arrival that feels worlds away. Inside, the floor plan delivers more than expected: a sunlit living room, formal dining room, updated white kitchen with breakfast space, and a generous family room anchored by a dramatic stone fireplace. Upstairs are three bedrooms and two full baths, while the finished walkout lower level adds a recreation room, flex room, and dedicated laundry space that can shift with the way you live. The outdoor experience is equally considered, with three distinct places to gather: a welcoming front patio, elevated rear deck, and lower-level patio leading toward the in-ground pool. Framed by bluestone, open lawn, and mature woods, the pool feels less like an amenity and more like a private summer destination. Yet this retreat is only minutes from Woodbury's Main Street celebrated for its restaurants, local shops, and antiques and close to trails and open space at Minortown Road Preserve and Orenaug Park. Private without being remote, flexible without feeling ordinary, this is a home designed for quiet mornings, effortless entertaining, and unforgettable weekends.

61 Minortown Rd, Woodbury
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