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28 Leavenworth Road

WOODBURY, CT

28 Leavenworth Road
$30,000/mo
37 Photos
  • 3 Beds
  • 2/1 Baths
  • 3,282 Sqft
  • 5.74 Acres

28 Leavenworth Road

WOODBURY, CT | Litchfield County

$30,000/mo
  • 3 Beds
  • 2/1 Baths
  • 3,282 Sqft
  • 5.74 Acres
  • Elementary School: Per Board of Ed
  • MLS #24148997

382 Weekeepeemee Road

WOODBURY, CT

382 Weekeepeemee Road New to Market
$2,195,000
40 Photos
  • 4 Beds
  • 3/1 Baths
  • 3,551 Sqft
  • 6.42 Acres

382 Weekeepeemee Road

WOODBURY, CT | Litchfield County

$2,195,000
  • 4 Beds
  • 3/1 Baths
  • 3,551 Sqft
  • 6.42 Acres
  • Elementary School: Per Board of Ed
  • MLS #24159893

0 Cowles Road

WOODBURY, CT

0 Cowles Road
$675,000
12 Photos
  • 23 Acres

0 Cowles Road

WOODBURY, CT | Litchfield County

$675,000
  • 23 Acres
  • Elementary School: Per Board of Ed
  • MLS #24084159

52 Steeple View Lane

WOODBURY, CT

52 Steeple View Lane Under Contract
$895,000
31 Photos
  • 4 Beds
  • 2/1 Baths
  • 3,776 Sqft
  • 1.38 Acres

52 Steeple View Lane

WOODBURY, CT | Litchfield County

$895,000
  • 4 Beds
  • 2/1 Baths
  • 3,776 Sqft
  • 1.38 Acres
  • Elementary School: Mitchell
  • MLS #24145387

43 Mill Road

WOODBURY, CT

43 Mill Road Under Contract
$675,000
38 Photos
  • 3 Beds
  • 2/1 Baths
  • 2,073 Sqft
  • 1.99 Acres

43 Mill Road

WOODBURY, CT | Litchfield County

$675,000
  • 3 Beds
  • 2/1 Baths
  • 2,073 Sqft
  • 1.99 Acres
  • Elementary School: Mitchell
  • MLS #24152365

24 Fox Run

WOODBURY, CT

24 Fox Run Coming Soon
$315,000
27 Photos
  • 2 Beds
  • 2 Baths
  • 1,542 Sqft

24 Fox Run

WOODBURY, CT | Litchfield County

$315,000
  • 2 Beds
  • 2 Baths
  • 1,542 Sqft

Be the first to know: On Market Mar 30

  • Elementary School: Per Board of Ed
  • MLS #24159700

58 Good Hill Road

WOODBURY, CT

58 Good Hill Road Coming Soon
$699,000
40 Photos
  • 3 Beds
  • 3/1 Baths
  • 3,210 Sqft
  • 2.16 Acres

58 Good Hill Road

WOODBURY, CT | Litchfield County

$699,000
  • 3 Beds
  • 3/1 Baths
  • 3,210 Sqft
  • 2.16 Acres

Be the first to know: On Market Mar 23

  • Elementary School: Mitchell
  • MLS #24155513

107 Main Street North

WOODBURY, CT

107 Main Street North
$2,500/mo
8 Photos
  • 1,700 Sqft

107 Main Street North

WOODBURY, CT | Litchfield County

$2,500/mo
  • 1,700 Sqft
  • MLS #24067493

439 Washington Road

WOODBURY, CT

439 Washington Road
$314,900
34 Photos
  • 1/1 Baths
  • 1,920 Sqft
  • 9.88 Acres

439 Washington Road

WOODBURY, CT | Litchfield County

$314,900
Reduced from $349,900
  • 1/1 Baths
  • 1,920 Sqft
  • 9.88 Acres
  • MLS #24078389

439 Washington Road

WOODBURY, CT

439 Washington Road
$314,900
32 Photos
  • 2 Beds
  • 1/1 Baths
  • 1,920 Sqft
  • 9.88 Acres

439 Washington Road

WOODBURY, CT | Litchfield County

$314,900
Reduced from $349,900
  • 2 Beds
  • 1/1 Baths
  • 1,920 Sqft
  • 9.88 Acres
  • Elementary School: Mitchell
  • MLS #24078648

337 Main Street South

WOODBURY, CT

337 Main Street South
$899,900
40 Photos
  • 4 Beds
  • 2/1 Baths
  • 3,700 Sqft
  • 1.39 Acres

337 Main Street South

WOODBURY, CT | Litchfield County

$899,900
  • 4 Beds
  • 2/1 Baths
  • 3,700 Sqft
  • 1.39 Acres
  • Elementary School: Mitchell
  • MLS #24078350

45 North Gate Road

WOODBURY, CT

45 North Gate Road
$1,100,000
40 Photos
  • 4 Beds
  • 2/1 Baths
  • 3,545 Sqft
  • 2.34 Acres

45 North Gate Road

WOODBURY, CT | Litchfield County

$1,100,000
  • 4 Beds
  • 2/1 Baths
  • 3,545 Sqft
  • 2.34 Acres
  • Elementary School: Mitchell
  • MLS #24092553

73 Main Street South #1B

WOODBURY, CT

73 Main Street South #1B
$1,600/mo
9 Photos
  • 1,375 Sqft

73 Main Street South #1B

WOODBURY, CT | Litchfield County

$1,600/mo
Reduced from $1,800
  • 1,375 Sqft
  • MLS #24114925

33 Washington Avenue

WOODBURY, CT

33 Washington Avenue
$3,750/mo
31 Photos
  • 2 Beds
  • 2 Baths
  • 1,968 Sqft
  • 0.84 Acres

33 Washington Avenue

WOODBURY, CT | Litchfield County

$3,750/mo
Reduced from $3,950/mo
  • 2 Beds
  • 2 Baths
  • 1,968 Sqft
  • 0.84 Acres
  • Elementary School: Per Board of Ed
  • MLS #24122197

Woodbury Real Estate Market

Single Family Homes
February 2026
February 2025
Woodbury, CT Average Days on Market
February 2026 78
February 2025 74  +5.1%
Median Sales Price homes in Woodbury
February 2026 $626K
February 2025 $780K  -19.7%
Woodbury, CT Average Price per Square Foot
February 2026 $223
February 2025 $263  -15.4%
Total Single Family Homes Sold in Woodbury, CT
February 2026 4
February 2025 7  -42.9%