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

$850,000
4 Beds ⋅ 2 Baths ⋅ 24183601 MLS
Built in 1854, this 5.91 acre property offers an incredible value impossible to replicate today for the price. The property includes an Italianate stone home with an approx 675 sq foot retail/office room with a separate entrance at the driveway, a 28' x 53' post and beam barn with a full walkout lower level, a large pond, stone walls, incredible perennial garden surround, and a 21' x 45' accessory building with heat - great guest house or in-law potential. Inspired by Tuscan villas, Italianate style homes, usually square and symmetrical, were popular in the late 19th C. in New England. Park-like grounds; large pond has goldfish (see pics). The 3532 square foot main home has potential for an in-home business, or retail shop as it once was. Other potential uses in this highly-visible location include using the barn for farm animals and/or horses. Home has 4 bedrooms, 2 full bathrooms, 3 fireplaces, and approx 435 sq foot foot, renovated, eat-in, sunny kitchen with leathered granite counters and stainless appliances. New oil furnace 2026. Septic recently maintained (new pump, piping, and floats in 2022 by Garrity, no problems since). 50 gallon water heater Oct 2022. Substantial moldings and built-ins, front and back staircases, specialty stainless skylights, and a rooftop belvedere, which looks beautiful lit up at night, atop the well maintained copper roof. Minutes to three towns centers of Woodbury, Watertown, and Bethlehem. Guesthouse has elec.

1917 Main St N, Woodbury
$819,000
3 Beds ⋅ 2 Baths ⋅ 24182784 MLS
Live Stress-Free in This Income-Producing Equestrian Retreat! Enjoy the best of country living while generating income from your property. Rental revenue from a separate 1 BR apartment and 4 of the 10 horse stalls offers a rare opportunity to offset ownership costs! Situated on 5.76 level acres of open pasture and riding space, this equestrian property is ideal for horse enthusiasts, trainers, or anyone seeking a peaceful rural lifestyle. The horse facilities include 4 barns with a total of 10 stalls, 2 wash stalls, and a 20 x 60-meter riding arena with premium stone dust and sand footing. The grounds offer ample space for turnout, training, recreation, and relaxation, creating the perfect balance of functionality and tranquility. At the heart of the property is a charming 3-bedroom, 2-bath ranch home featuring a windowed kitchen, spacious dining room for entertaining, vaulted ceilings, 2 fireplaces with wood stoves, a WIC, and an oversized lower-level bonus room. Step outside to a private backyard designed for gatherings and enjoyment, complete with a thriving vegetable garden. The 1 BR apartment is currently rented, but can easily serve as an in-law suite or guest quarters. There is also a 3 car garage for the car enthusiast! The possibilities are endless! The present owners, Serenity Farm Horse Rescue, have lovingly cared for this property for years. As their rescue continues to grow, they are seeking a larger facility to support their expansion. Shown by private appt.

92 Minortown Rd, Woodbury
$775,000
4 Beds ⋅ 4 Baths ⋅ 24138386 MLS
The Orton-Martin Homestead. One of Woodbury's oldest homes has been updated for today's lifestyle. History surrounds you with wide board flooring, library built-ins, two fireplaces and 1850 barn. This four -bedroom home offers spacious rooms, three finished levels and hidden delights. Enjoy picnics under the mature trees on your own fenced-in level yard. Sidewalks take you everywhere on Main St where you can enjoy the Library, antique and retail shops, schools, churches, great restaurants and coffee shops. Parks and the Senior Center are all nearby. Only 90 minutes to NYC. Named by Reader's Digest as one of CT most charming towns. Come call Woodbury home!

28 School St, Woodbury
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