Woodbury, CT Real Estate & Homes for Sale

81 Listings Found:
  • Communities Woodbury
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28 Leavenworth Road

Woodbury, CT

28 Leavenworth Road
$30,000/mo
  • 3 bed
  • 2/1 bath
  • 3,282 sqft
  • 5.74 acres

557 Upper Grassy Hill Road

Woodbury, CT

557 Upper Grassy Hill Road
$895,000
  • 4 bed
  • 3/1 bath
  • 3,784 sqft
  • 2.73 acres
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235 White Deer Rocks Road #Guest House

Woodbury, CT

235 White Deer Rocks Road #Guest House
$3,000/mo
  • 1 bed
  • 1 bath
  • 750 sqft
  • 4.02 acres

30 Hollow Road

Woodbury, CT

30 Hollow Road
$1,495,000
  • 5 bed
  • 4/1 bath
  • 4,884 sqft
  • 2.24 acres

260 White Deer Rocks Road

Woodbury, CT

260 White Deer Rocks Road
$7,500/mo
  • 4 bed
  • 2/1 bath
  • 3,159 sqft
  • 11.9 acres

0 Cowles Road

Woodbury, CT

Contingent The sellers have accepted an offer on the property, however, the offer relies on contingencies yet to be lifted. It may still be possible to tour these properties and submit a backup offer.
0 Cowles Road
$675,000
  • 23 acres

54 Bear Run

Woodbury, CT

Contingent The sellers have accepted an offer on the property, however, the offer relies on contingencies yet to be lifted. It may still be possible to tour these properties and submit a backup offer.
54 Bear Run
$699,000
  • 4 bed
  • 2/1 bath
  • 2,849 sqft
  • 1.44 acres

382 Weekeepeemee Road

Woodbury, CT

382 Weekeepeemee Road Under Contract
$2,195,000
  • 4 bed
  • 3/1 bath
  • 3,551 sqft
  • 6.42 acres

107 Main Street North

Woodbury, CT

107 Main Street North
$2,500/mo
  • 1,700 sqft

45 North Gate Road

Woodbury, CT

45 North Gate Road
$1,100,000
  • 4 bed
  • 2/1 bath
  • 3,545 sqft
  • 2.34 acres

33 Washington Avenue

Woodbury, CT

33 Washington Avenue
$3,750/mo
  • 2 bed
  • 2 bath
  • 1,968 sqft
  • 0.84 acres

8 Tamarack Lane

Woodbury, CT

8 Tamarack Lane
$325,000
  • 2 bed
  • 2 bath
  • 2,118 sqft

51 Sherman Hill Road #STE A203

Woodbury, CT

51 Sherman Hill Road #STE A203
$850/mo
  • 1,610 sqft

34 Transylvania Road

Woodbury, CT

34 Transylvania Road
$479,900
  • 3 bed
  • 2/1 bath
  • 2,016 sqft
  • 3 acres

Woodbury Real Estate Market

Single Family Homes
April 2026
April 2025
Woodbury, CT Average Days on Market
April 2026 29
April 2025 68 -57.6%
Median Sales Price homes in Woodbury
April 2026 $578K
April 2025 $769K -24.9%
Woodbury, CT Average Price per Square Foot
April 2026 $245
April 2025 $286 -14.2%
Total Single Family Homes Sold in Woodbury, CT
April 2026 8
April 2025 9 -11.1%

Woodbury is within Litchfield Hills, Connecticut

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