Woodbury, CT Homes

• 

  $740,000 Sold Aug 01, 2025

  101 Railtree Hill Rd, Woodbury, CT 06798

  • 4 Beds
  • 2.5 Baths
  • 3,341 Sq Ft
  • Built 1987

  Last Sold Summary

  • 1% Below List Price
  • $221/SF
  • 19 Days On Market

  Current Estimated Value $749,999

  Last Listing Agent Ellen Vincent William Raveis Real Estate

  101 Railtree Hill Rd, Woodbury, CT 06798
• 

  Est $664,104 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,502 Sq Ft

  37 Plumb Brook Rd, Woodbury, CT 06798

  37 Plumb Brook Rd, Woodbury, CT 06798
• 

  $865,000 Sold Jan 08, 2025

  172 Good Hill Rd, Woodbury, CT 06798

  • 3 Beds
  • 3.5 Baths
  • 2,929 Sq Ft
  • Built 1993

  Last Sold Summary

  • 7% Below List Price
  • $295/SF
  • 25 Days On Market

  Current Estimated Value $916,590

  Last Listing Agent Tim Drakeley Drakeley Real Estate, Inc.

  172 Good Hill Rd, Woodbury, CT 06798
• 

  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 546 Sq Ft

  22 Pilgrim Trail Unit 7, Woodbury, CT 06798

  22 Pilgrim Trail Unit 7, Woodbury, CT 06798
• 

  $530,000 Sold Mar 26, 2025

  431 Sherman Hill Rd, Woodbury, CT 06798

  • 1 Bed
  • 2.5 Baths
  • 3,207 Sq Ft
  • Built 1970

  Last Sold Summary

  • 27% Below List Price
  • $165/SF
  • 219 Days On Market

  Current Estimated Value $549,594

  Last Listing Agent Dawn Ciappetta Coldwell Banker Realty

  431 Sherman Hill Rd, Woodbury, CT 06798
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  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 546 Sq Ft

  34 Arrowhead Way Unit 2, Woodbury, CT 06798

  34 Arrowhead Way Unit 2, Woodbury, CT 06798
• 

  $104,000 Sold Feb 19, 2025

  16 Pilgrim Trail Unit 6, Woodbury, CT 06798

  • 1 Bed
  • 1 Bath
  • 546 Sq Ft
  • Built 1965

  Last Sold Summary

  • 10% Below List Price
  • $190/SF
  • 86 Days On Market

  Last Listing Agent Rebecca Koladis Berkshire Hathaway NE Prop.

  16 Pilgrim Trail Unit 6, Woodbury, CT 06798
• 

  Est $176,472 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 913 Sq Ft

  229 Bacon Pond Rd Unit 421, Woodbury, CT 06798

  229 Bacon Pond Rd Unit 421, Woodbury, CT 06798
• 

  $1,060,000 Sold Jan 22, 2025

  382 Weekeepeemee Rd, Woodbury, CT 06798

  • 4 Beds
  • 3.5 Baths
  • 3,551 Sq Ft
  • Built 1805

  Last Sold Summary

  • 12% Above List Price
  • $299/SF
  • 50 Days On Market

  Current Estimated Value $934,421

  Last Listing Agent Jeff Phillips William Pitt Sotheby's Int'l

  382 Weekeepeemee Rd, Woodbury, CT 06798
• 

  Est $189,232 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 913 Sq Ft

  229 Bacon Pond Rd Unit 321, Woodbury, CT 06798

  229 Bacon Pond Rd Unit 321, Woodbury, CT 06798
• 

  $399,000 Sold Jan 17, 2025

  35 Weekeepeemee Rd, Woodbury, CT 06798

  • 3 Beds
  • 1.5 Baths
  • 1,959 Sq Ft
  • Built 1836

  Last Sold Summary

  • 11% Below List Price
  • $204/SF
  • 240 Days On Market

  Current Estimated Value $449,419

  Last Listing Agent Sindy Butkus Klemm Real Estate Inc

  35 Weekeepeemee Rd, Woodbury, CT 06798
• 

  Est $192,475 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 913 Sq Ft

  229 Bacon Pond Rd Unit 224, Woodbury, CT 06798

  229 Bacon Pond Rd Unit 224, Woodbury, CT 06798
• 

  $760,000 Sold Aug 15, 2025

  133 Hoop Pole Hill Rd, Woodbury, CT 06798

  • 4 Beds
  • 3.5 Baths
  • 2,994 Sq Ft
  • Built 2005

  Last Sold Summary

  • 10% Below List Price
  • $254/SF
  • 43 Days On Market

  Current Estimated Value $782,753

  Last Listing Agent William Glanville Glanville Real Estate

  133 Hoop Pole Hill Rd, Woodbury, CT 06798
• 

  Est $188,771 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 913 Sq Ft

  229 Bacon Pond Rd Unit 134, Woodbury, CT 06798

  229 Bacon Pond Rd Unit 134, Woodbury, CT 06798
• 

  $165,000 Sold Jul 01, 2025

  229 Bacon Pond Rd Unit 144, Woodbury, CT 06798

  • 2 Beds
  • 1 Bath
  • 913 Sq Ft
  • Built 1971

  Last Sold Summary

  • 2% Below List Price
  • $181/SF
  • 18 Days On Market

  Current Estimated Value $168,926

  Last Listing Agent Reza Abbassi New Door Realty

  229 Bacon Pond Rd Unit 144, Woodbury, CT 06798
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  Est $176,662 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 913 Sq Ft

  229 Bacon Pond Rd Unit 121, Woodbury, CT 06798

  229 Bacon Pond Rd Unit 121, Woodbury, CT 06798
• 

  $500,000 Sold Nov 17, 2025

  12 Spring St, Woodbury, CT 06798

  • 3 Beds
  • 2 Baths
  • 2,064 Sq Ft
  • Built 1900

  Last Sold Summary

  • 9% Below List Price
  • $242/SF
  • 77 Days On Market

  Last Listing Agent Rhya Szymansky Drakeley Real Estate, Inc.

  12 Spring St, Woodbury, CT 06798
• 

  Est $567,368 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,127 Sq Ft

  Unlisted Address

  Unlisted Address
• 

  $1,400,000 Sold Jul 17, 2025

  39 Painter Hill Rd, Woodbury, CT 06798

  • 4 Beds
  • 3 Baths
  • 2,418 Sq Ft
  • Built 1810

  Last Sold Summary

  • 7% Below List Price
  • $579/SF
  • 62 Days On Market

  Last Listing Agent Stacey Matthews W. Raveis Lifestyles Realty

  39 Painter Hill Rd, Woodbury, CT 06798
• 

  Est $533,919 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 2,034 Sq Ft

  99 Old Sherman Hill Rd, Woodbury, CT 06798

  99 Old Sherman Hill Rd, Woodbury, CT 06798
• 

  $812,500 Sold Mar 03, 2025

  40 Tuttle Rd, Woodbury, CT 06798

  • 5 Beds
  • 2.5 Baths
  • 3,915 Sq Ft
  • Built 2006

  Last Sold Summary

  • 8% Below List Price
  • $208/SF
  • 169 Days On Market

  Current Estimated Value $844,097

  Last Listing Agent Sally Gorman Klemm Real Estate Inc

  40 Tuttle Rd, Woodbury, CT 06798
• 

  Est $416,176 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 1,564 Sq Ft

  59 Old Sherman Hill Rd, Woodbury, CT 06798

  59 Old Sherman Hill Rd, Woodbury, CT 06798
• 

  $895,000 Sold Apr 29, 2025

  35 Fawn Meadow Ln, Woodbury, CT 06798

  • 4 Beds
  • 3.5 Baths
  • 2,600 Sq Ft
  • Built 2021

  Last Sold Summary

  • $344/SF
  • 31 Days On Market

  Current Estimated Value $932,115

  Last Listing Agent Gregory Cohen William Pitt Sotheby's Int'l

  35 Fawn Meadow Ln, Woodbury, CT 06798
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  Est $634,612 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,283 Sq Ft

  253 Bacon Pond Rd, Woodbury, CT 06798

  253 Bacon Pond Rd, Woodbury, CT 06798
• 

  $120,000 Sold May 19, 2025

  16 Pilgrim Trail Unit 3, Woodbury, CT 06798

  • 1 Bed
  • 1 Bath
  • 546 Sq Ft
  • Built 1965

  Last Sold Summary

  • 8% Below List Price
  • $220/SF
  • 18 Days On Market

  Last Listing Agent Carlo Bettini Weichert REALTORS Briotti Group

  16 Pilgrim Trail Unit 3, Woodbury, CT 06798
• 

  Est $659,099 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 1,821 Sq Ft

  104 Old Sherman Hill Rd, Woodbury, CT 06798

  104 Old Sherman Hill Rd, Woodbury, CT 06798
• 

  $975,000 Sold Oct 01, 2025

  364 Hoop Pole Hill Rd, Woodbury, CT 06798

  • 5 Beds
  • 3 Baths
  • 3,450 Sq Ft
  • Built 2006

  Last Sold Summary

  • $283/SF
  • 33 Days On Market

  Last Listing Agent Kary Apanovitch Coldwell Banker Realty

  364 Hoop Pole Hill Rd, Woodbury, CT 06798
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  Est $559,540 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,276 Sq Ft

  30 Applegate Ln, Woodbury, CT 06798

  30 Applegate Ln, Woodbury, CT 06798
• 

  $550,000 Sold Nov 21, 2025

  212 Main St N, Woodbury, CT 06798

  • 4 Beds
  • 3 Baths
  • 2,861 Sq Ft
  • Built 1830

  Last Sold Summary

  • 15% Below List Price
  • $192/SF
  • 190 Days On Market

  Last Listing Agent Heather Crabtree RE/MAX RISE

  212 Main St N, Woodbury, CT 06798
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  Est $446,213 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,819 Sq Ft

  15 Ridgewood Rd, Woodbury, CT 06798

  15 Ridgewood Rd, Woodbury, CT 06798
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  $580,000 Sold Dec 03, 2025

  101 Plumb Brook Rd, Woodbury, CT 06798

  • 3 Beds
  • 2 Baths
  • 1,922 Sq Ft
  • Built 1978

  Last Sold Summary

  • 3% Below List Price
  • $302/SF
  • 102 Days On Market

  Last Listing Agent Mary Ann Bennett Drakeley Real Estate, Inc.

  101 Plumb Brook Rd, Woodbury, CT 06798
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  Est $680,562 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 4,130 Sq Ft

  74 Scuppo Rd, Woodbury, CT 06798

  74 Scuppo Rd, Woodbury, CT 06798
• 

  $530,000 Sold Oct 15, 2025

  467 Weekeepeemee Rd, Woodbury, CT 06798

  • 4 Beds
  • 2.5 Baths
  • 2,555 Sq Ft
  • Built 1977

  Last Sold Summary

  • 14% Below List Price
  • $207/SF
  • 131 Days On Market

  Last Listing Agent Tammy Powling Showcase Realty, Inc.

  467 Weekeepeemee Rd, Woodbury, CT 06798
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  Est $800,249 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,712 Sq Ft

  271 Quassapaug Rd, Woodbury, CT 06798

  271 Quassapaug Rd, Woodbury, CT 06798
• 

  $195,000 Sold Feb 28, 2025

  229 Bacon Pond Rd Unit 311, Woodbury, CT 06798

  • 2 Beds
  • 1 Bath
  • 913 Sq Ft
  • Built 1971

  Last Sold Summary

  • 1% Above List Price
  • $214/SF
  • 16 Days On Market

  Current Estimated Value $200,294

  Last Listing Agent John Calabrese Better Living Realty, LLC

  229 Bacon Pond Rd Unit 311, Woodbury, CT 06798
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  Est $373,878 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,269 Sq Ft

  15 Lake Rd, Woodbury, CT 06798

  15 Lake Rd, Woodbury, CT 06798
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  $735,000 Sold Jan 17, 2025

  194 Washington Rd, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 3,182 Sq Ft
  • Built 1836

  Last Sold Summary

  • 1% Above List Price
  • $231/SF
  • 78 Days On Market

  Current Estimated Value $767,411

  Last Listing Agent Kevin Hickey William Pitt Sotheby's Int'l

  194 Washington Rd, Woodbury, CT 06798
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  Est $411,898 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,284 Sq Ft

  25 Atwood Rd, Woodbury, CT 06798

  25 Atwood Rd, Woodbury, CT 06798
• 

  $340,000 Sold Oct 23, 2025

  4 Clubhouse Dr Unit 4, Woodbury, CT 06798

  • 3 Beds
  • 3 Baths
  • 1,538 Sq Ft
  • Built 1972

  Last Sold Summary

  • 3% Below List Price
  • $221/SF
  • 42 Days On Market

  Last Listing Agent Chelsea Stinson Coldwell Banker Realty

  4 Clubhouse Dr Unit 4, Woodbury, CT 06798
• 

  Est $500,457 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 2,494 Sq Ft

  171 Kimberly Ln, Woodbury, CT 06798

  171 Kimberly Ln, Woodbury, CT 06798

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