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

$2,995,000
4 Beds ⋅ 6 Baths ⋅ 24163576 MLS
Warren's Landing on the Pomperaug is an extraordinary estate where historic character is centered around a beautifully preserved 1890 Greek Revival residence. The home offers four bedrooms, timeless architectural details, spacious rooms, 4 fireplaces and custom built-ins. The impressive six-barn complex provides exceptional flexibility, featuring a retail shop, extensive equipment storage, a two-car garage, pool cabana and pool equipment building. A newly constructed temperature controlled 3,800-square-foot post-and-beam barn with a half bath and laundry room at the rear of the property further expand the property's possibilities. There are also an equipment/horse barn and riverside cabin. Outdoor living is equally remarkable with a stunning new in-ground gunite pool surrounded by lush landscaping. Designed for both relaxation and entertaining, the grounds include a custom "summer kitchen" with a European-style outdoor pizza oven, gas grill, and screened dining pavilion-perfect for hosting gatherings or enjoying quiet evenings. The 18.3-acre setting includes mature trees, open meadows, scenic walking trails, and frontage along the protected Pomperaug River, creating a private and picturesque retreat. Rich in history yet thoughtfully updated, this rare estate offers an exceptional combination of beauty, functionality, and enduring charm. A comprehensive list of recent improvements is available upon request. Buyer must do due diligence with the town for possible uses.

920 Main St S, Woodbury
$1,995,000
4 Beds ⋅ 5 Baths ⋅ 24136657 MLS
Step into History with Modern Comfort Experience the undeniable charm of this circa 1685 residence-one of the oldest continuously inhabited homes in the county. Thoughtfully restored and beautifully updated, this remarkable property blends centuries of character with today's modern conveniences. Inside, the open floor plan creates a warm and inviting flow, with three cozy sitting rooms surrounding the impressive central hearth. The chef's kitchen features a large center island, breakfast bar, and sweeping views of the expansive lawn-perfect for both everyday living and entertaining. Original details abound, including hand-hewn beams, wide king's board flooring, and the historic cooking fireplace that anchors the heart of the home. Recent upgrades include a new HVAC system with humidification and numerous other enhancements (see attachments for the full list). A new mahogany deck overlooks the level backyard, leading toward a picturesque bridge, sparkling pool, and inviting cabana. Two barns sit near the parking area-one offering garage space and the other ready for your imagination: ideal for a future guest house, studio, or recreation room, this barn has new propane heat, water and electric service. This extraordinary home offers the rare opportunity to own a piece of history-beautifully updated for modern living.

55 Good Hill Rd, Woodbury
$1,795,000
2 Beds ⋅ 2 Baths ⋅ 24185479 MLS ⋅ Woodlake BLDG.
Just 2 hours from New York City, this exceptional lakefront retreat offers a rare blend of privacy, natural beauty & turnkey luxury. Tucked at the end of West Lake Rd and bordered by the protected woodlands of Flanders Nature Center Preserve, the property enjoys sweeping, unobstructed views across pristine Lake Quassapaug to historic Tranquillity Farm, designed by McKim, Mead & White. Lake Quassapaug is a private lake with no public access & a 10-mph speed limit, creating an ideal setting for boating, fishing, swimming & year-round recreation. Private beach & dock provide direct water access, while the renovated lakeside cabana offers flexible space for a home office, fitness studio or retreat. Outdoor KIT, BBQ area & multiple patios, including a waterfront terrace, are perfect for entertaining. Renovated in 2020, the home features a beautifully appointed gourmet KIT with premium finishes & seamless flow to inviting living spaces. One of only a select few lakefront homes in Woodbury, it benefits from the town's favorable tax structure while being minutes to historic Main St, acclaimed restaurants & antique shops. Town of Woodbury recognizes 112 West Lake Road and a few other neighboring properties as condominium units. All other homes on the Lake are in Middlebury CT. Rare opportunity to own a fully renovated waterfront home with exceptional privacy, spectacular views & an unparalleled lake lifestyle.

112 W Lake Rd Unit 112, Woodbury
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