Woodbury


Woodbury, which means “Dwelling Place in the Woods,” was settled in 1673 as a farming community and then grew into a home for small factories in the mid-19th century. The charming Litchfield County town has since been established as a prime destination for antiques, and has earned the title of “Antiques Capital of Connecticut.” Woodbury’s town center hosts dozens of antiques shops, many of which are housed in former historic residences. A gazebo, art galleries, fine dining establishments and a variety of eclectic boutiques line the town’s quaint center, which is reminiscent of a Norman Rockwell scene. The late composer LeRoy Anderson wrote the Christmas classic “Sleigh Ride” at his residence in Woodbury – ironically during a summer heat wave.

Outdoor activities abound from trail walking to swimming, kayaking and fishing within Woodbury’s three parks, three trout-stocked rivers and 1,900-acre Flanders Nature Sanctuary. Flanders Nature Center and Land Trust ensures that much of the town’s open space will never be developed and runs year-round activities for all. Equestrian pursuits are available at many local farms and stables. Located in the southernmost part of Litchfield County, Woodbury is situated within close proximity of Interstate 84, providing easy access to Hartford, New Haven and Fairfield Counties, as well as Manhattan within 90 minutes.

Woodbury, which means “Dwelling Place in the Woods,” was settled in 1673 as a farming community and then grew into a home for small factories in the mid-19th century. The charming Litchfield County town has since been established as a prime destination for antiques, and has earned the title of “Antiques Capital of Connecticut.” Woodbury’s town center hosts dozens of antiques shops, many of which are housed in former historic residences. A gazebo, art galleries, fine dining establishments and a variety of eclectic boutiques line the town’s quaint center, which is reminiscent of a Norman Rockwell scene. The late composer LeRoy Anderson wrote the Christmas classic “Sleigh Ride” at his residence in Woodbury – ironically during a summer heat wave.

Outdoor activities abound from trail walking to swimming, kayaking and fishing within Woodbury’s three parks, three trout-stocked rivers and 1,900-acre Flanders Nature Sanctuary. Flanders Nature Center and Land Trust ensures that much of the town’s open space will never be developed and runs year-round activities for all. Equestrian pursuits are available at many local farms and stables. Located in the southernmost part of Litchfield County, Woodbury is situated within close proximity of Interstate 84, providing easy access to Hartford, New Haven and Fairfield Counties, as well as Manhattan within 90 minutes.

Woodbury, which means “Dwelling Place in the Woods,” was settled in 1673 as a farming community and then grew into a home for small factories in the mid-19th century. The charming Litchfield County town has since been established as a prime destination for antiques, and has earned the title of “Antiques Capital of Connecticut.” Woodbury’s town center hosts dozens of antiques shops, many of which are housed in former historic residences. A gazebo, art galleries, fine dining establishments and a variety of eclectic boutiques line the town’s quaint center, which is reminiscent of a Norman Rockwell scene. The late composer LeRoy Anderson wrote the Christmas classic “Sleigh Ride” at his residence in Woodbury – ironically during a summer heat wave.

Outdoor activities abound from trail walking to swimming, kayaking and fishing within Woodbury’s three parks, three trout-stocked rivers and 1,900-acre Flanders Nature Sanctuary. Flanders Nature Center and Land Trust ensures that much of the town’s open space will never be developed and runs year-round activities for all. Equestrian pursuits are available at many local farms and stables. Located in the southernmost part of Litchfield County, Woodbury is situated within close proximity of Interstate 84, providing easy access to Hartford, New Haven and Fairfield Counties, as well as Manhattan within 90 minutes.

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Featured Listings

11 Owl Ridge Road
Woodbury, CT $2,000,000

11 Owl Ridge Road

Woodbury, CT

$2,000,000
  • 5 Beds
  • 4/3 Baths
  • 4,363 Sqft
30 Hollow Road
Woodbury, CT $1,495,000

30 Hollow Road

Woodbury, CT

$1,495,000
  • 5 Beds
  • 4/1 Baths
  • 4,884 Sqft
557 Upper Grassy Hill Road
Woodbury, CT $895,000

557 Upper Grassy Hill Road

Woodbury, CT

$895,000
  • 4 Beds
  • 3/1 Baths
  • 3,784 Sqft
253 Bacon Pond Road
Woodbury, CT $895,000

253 Bacon Pond Road

Woodbury, CT

$895,000
  • 4 Beds
  • 2/1 Baths
  • 2,283 Sqft
0 Cowles Road
Woodbury, CT $675,000

0 Cowles Road

Woodbury, CT

$675,000
  • 23.00 Acres
33 Hurds Hill Road
Woodbury, CT $525,000

33 Hurds Hill Road

Woodbury, CT

$525,000
  • 5 Beds
  • 3 Baths
  • 4,130 Sqft
18 South Street
Woodbury, CT $495,000

18 South Street

Woodbury, CT

$495,000
  • 4 Beds
  • 2/1 Baths
  • 2,880 Sqft
28 Leavenworth Road
Woodbury, CT $30,000/mo

28 Leavenworth Road

Woodbury, CT

$30,000/mo
  • 3 Beds
  • 2/1 Baths
  • 3,282 Sqft

Woodbury

Area Map

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Woodbury

Market Snapshot

Units Sold

June 2026

18 TOTAL UNITS

image description +200.0% image description +38.5% vs

Median Sales Price

June 2026 - Single Family Homes

$514K
image description -27.2% image description -23.3% vs

Percentage of Asking Price

June 2026 Single Family Homes

102%
image description -1.1% image description +3.3% vs
102%
image description -1.1% image description +3.3% vs
102%
image description -1.1% image description +3.3% vs
102%
image description -1.1% image description +3.3% vs
102%
image description -1.1% image description +3.3% vs