Woodbury, CT Homes

• 

  $952,000 Sold Apr 15, 2025

  5 Bear Run, Woodbury, CT 06798

  • 4 Beds
  • 4.5 Baths
  • 5,915 Sq Ft
  • Built 1997

  Last Sold Summary

  • 21% Below List Price
  • $161/SF
  • 132 Days On Market

  Current Estimated Value $1,015,708

  Last Listing Agent Shelley Drakeley Drakeley Real Estate, Inc.

  5 Bear Run, Woodbury, CT 06798
• 

  Est $662,225 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,416 Sq Ft

  652 Upper Grassy Hill Rd, Woodbury, CT 06798

  652 Upper Grassy Hill Rd, Woodbury, CT 06798
• 

  $722,000 Sold Aug 22, 2025

  29 Lighthouse Rd, Woodbury, CT 06798

  • 3 Beds
  • 2 Baths
  • 2,202 Sq Ft
  • Built 1960

  Last Sold Summary

  • 26% Above List Price
  • $328/SF
  • 5 Days On Market

  Current Estimated Value $705,537

  Last Listing Agent Christian Jensen William Pitt Sotheby's Int'l

  29 Lighthouse Rd, Woodbury, CT 06798
• 

  Est $708,838 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,480 Sq Ft

  88 Hard Hill Rd, Woodbury, CT 06798

  88 Hard Hill Rd, Woodbury, CT 06798
• 

  $825,000 Sold Sep 05, 2025

  77 Northgate Rd, Woodbury, CT 06798

  • 4 Beds
  • 2.5 Baths
  • 2,519 Sq Ft
  • Built 2016

  Last Sold Summary

  • 5% Below List Price
  • $328/SF
  • 155 Days On Market

  Current Estimated Value $818,754

  Last Listing Agent Jason Arcuri eXp Realty

  77 Northgate Rd, Woodbury, CT 06798
• 

  Est $477,209 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,614 Sq Ft

  79 Flanders Rd, Woodbury, CT 06798

  79 Flanders Rd, Woodbury, CT 06798
• 

  $290,000 Sold Jun 13, 2025

  1 Woods Way Unit 118E, Woodbury, CT 06798

  • 2 Beds
  • 3 Baths
  • 1,773 Sq Ft
  • Built 1980

  Last Sold Summary

  • $164/SF
  • 16 Days On Market

  Last Listing Agent Terry Lee Adams Adams & Adams Real Estate

  1 Woods Way Unit 118E, Woodbury, CT 06798
• 

  Est $482,961 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,366 Sq Ft

  7 Washington Rd, Woodbury, CT 06798

  7 Washington Rd, Woodbury, CT 06798
• 

  $312,000 Sold Feb 21, 2025

  49 Woods Way, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 2,045 Sq Ft
  • Built 1980

  Last Sold Summary

  • 1% Below List Price
  • $153/SF
  • 90 Days On Market

  Last Listing Agent Cathy Masi Flagpole Realty Inc

  49 Woods Way, Woodbury, CT 06798
• 

  Est $403,239 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,792 Sq Ft

  52 White Deer Rocks Rd, Woodbury, CT 06798

  52 White Deer Rocks Rd, Woodbury, CT 06798
• 

  $590,000 Sold Apr 07, 2025

  301 Transylvania Rd, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 2,628 Sq Ft
  • Built 1930

  Last Sold Summary

  • 16% Below List Price
  • $225/SF
  • 8 Days On Market

  Current Estimated Value $618,687

  Last Listing Agent Jane Spino Showcase Realty, Inc.

  301 Transylvania Rd, Woodbury, CT 06798
• 

  Est $843,999 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,568 Sq Ft

  53 Leavenworth Rd, Woodbury, CT 06798

  53 Leavenworth Rd, Woodbury, CT 06798
• 

  $262,500 Sold Sep 04, 2025

  1 Summit Ct Unit 1, Woodbury, CT 06798

  • 2 Beds
  • 2 Baths
  • 1,182 Sq Ft
  • Built 1980

  Last Sold Summary

  • 3% Below List Price
  • $222/SF
  • 35 Days On Market

  Last Listing Agent Tim Drakeley Drakeley Real Estate, Inc.

  1 Summit Ct Unit 1, Woodbury, CT 06798
• 

  Est $768,225 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 3,069 Sq Ft

  22 Forest Ridge Rd, Woodbury, CT 06798

  22 Forest Ridge Rd, Woodbury, CT 06798
• 

  $200,000 Sold Mar 24, 2025

  229 Bacon Pond Rd Unit 352, Woodbury, CT 06798

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

  Last Sold Summary

  • 5% Above List Price
  • $219/SF
  • 22 Days On Market

  Current Estimated Value $199,686

  Last Listing Agent Nickie O'Toole Nickie Otoole Realty LLC

  229 Bacon Pond Rd Unit 352, Woodbury, CT 06798
• 

  Est $550,842 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,979 Sq Ft

  27 Tuttle Rd, Woodbury, CT 06798

  27 Tuttle Rd, Woodbury, CT 06798
• 

  $515,000 Sold Jun 30, 2025

  7 Orenaug Ave, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 1,918 Sq Ft
  • Built 1820

  Last Sold Summary

  • $269/SF
  • 44 Days On Market

  Current Estimated Value $515,161

  Last Listing Agent Lisa Titcomb William Pitt Sotheby's Int'l

  7 Orenaug Ave, Woodbury, CT 06798
• 

  Est $749,210 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,758 Sq Ft

  6 Meadowbrook Ln, Woodbury, CT 06798

  6 Meadowbrook Ln, Woodbury, CT 06798
• 

  $528,000 Sold Sep 09, 2025

  173 Railtree Hill Rd, Woodbury, CT 06798

  • 4 Beds
  • 3.5 Baths
  • 3,350 Sq Ft
  • Built 1990

  Last Sold Summary

  • 2% Above List Price
  • $158/SF
  • 18 Days On Market

  Current Estimated Value $537,166

  Last Listing Agent Lawrence Madow Calcagni Real Estate

  173 Railtree Hill Rd, Woodbury, CT 06798
• 

  Est $245,174 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 960 Sq Ft

  74 Washington Rd Unit 19, Woodbury, CT 06798

  74 Washington Rd Unit 19, Woodbury, CT 06798
• 

  $160,000 Sold May 20, 2025

  229 Bacon Pond Rd Unit 411, Woodbury, CT 06798

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

  Last Sold Summary

  • 6% Below List Price
  • $175/SF
  • 36 Days On Market

  Current Estimated Value $165,941

  Last Listing Agent Jeff Boucher Drakeley Real Estate, Inc.

  229 Bacon Pond Rd Unit 411, Woodbury, CT 06798
• 

  Est $610,690 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 2,709 Sq Ft

  112 Main St S, Woodbury, CT 06798

  112 Main St S, Woodbury, CT 06798
• 

  $875,000 Sold May 22, 2025

  447 Transylvania Rd, Woodbury, CT 06798

  • 5 Beds
  • 4 Baths
  • 3,978 Sq Ft
  • Built 2004

  Last Sold Summary

  • 10% Below List Price
  • $220/SF
  • 149 Days On Market

  Current Estimated Value $892,976

  Last Listing Agent Casey French Litchfield County Real Estate

  447 Transylvania Rd, Woodbury, CT 06798
• 

  Est $943,737 Not Listed For Sale

  • 6 Beds
  • 5 Baths
  • 4,080 Sq Ft

  9 Pleasant St, Woodbury, CT 06798

  9 Pleasant St, Woodbury, CT 06798
• 

  $595,000 Sold Jan 13, 2025

  40 Quanopaug Trail, Woodbury, CT 06798

  • 4 Beds
  • 2.5 Baths
  • 2,524 Sq Ft
  • Built 1972

  Last Sold Summary

  • $236/SF
  • 58 Days On Market

  Current Estimated Value $621,367

  Last Listing Agent Jeff Boucher Drakeley Real Estate, Inc.

  40 Quanopaug Trail, Woodbury, CT 06798
• 

  Est $407,783 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,576 Sq Ft

  57 Main St N, Woodbury, CT 06798

  57 Main St N, Woodbury, CT 06798
• 

  $615,000 Sold Oct 30, 2025

  130 Grassy Hill Rd, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 2,124 Sq Ft
  • Built 1988

  Last Sold Summary

  • 8% Below List Price
  • $290/SF
  • 116 Days On Market

  Last Listing Agent Wendy Brazauskas Coldwell Banker Realty

  130 Grassy Hill Rd, Woodbury, CT 06798
• 

  Est $471,554 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,082 Sq Ft

  27 Washington Rd, Woodbury, CT 06798

  27 Washington Rd, Woodbury, CT 06798
• 

  $184,000 Sold May 28, 2025

  229 Bacon Pond Rd Unit 132, Woodbury, CT 06798

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

  Last Sold Summary

  • 8% Below List Price
  • $202/SF
  • 56 Days On Market

  Current Estimated Value $187,054

  Last Listing Agent Tom Greto William Raveis Real Estate

  229 Bacon Pond Rd Unit 132, Woodbury, CT 06798
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  Est $431,288 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 2,085 Sq Ft

  13 Washington Rd, Woodbury, CT 06798

  13 Washington Rd, Woodbury, CT 06798
• 

  $267,000 Sold Sep 25, 2025

  29 Woods Way, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 2,450 Sq Ft
  • Built 1980

  Last Sold Summary

  • 3% Below List Price
  • $109/SF
  • 12 Days On Market

  Last Listing Agent Derek Greene Derek Greene

  29 Woods Way, Woodbury, CT 06798
• 

  Est $576,655 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,698 Sq Ft

  39 Judson Ave, Woodbury, CT 06798

  39 Judson Ave, Woodbury, CT 06798
• 

  $750,000 Sold Sep 05, 2025

  181 Railtree Hill Rd, Woodbury, CT 06798

  • 4 Beds
  • 3.5 Baths
  • 3,726 Sq Ft
  • Built 1986

  Last Sold Summary

  • 19% Below List Price
  • $201/SF
  • 111 Days On Market

  Current Estimated Value $753,048

  Last Listing Agent Tim Drakeley Drakeley Real Estate, Inc.

  181 Railtree Hill Rd, Woodbury, CT 06798
• 

  Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 2,285 Sq Ft

  473 Main St S, Woodbury, CT 06798

  473 Main St S, Woodbury, CT 06798
• 

  $290,000 Sold Apr 07, 2025

  6 Hickory Ln Unit 6, Woodbury, CT 06798

  • 2 Beds
  • 2.5 Baths
  • 1,895 Sq Ft
  • Built 1974

  Last Sold Summary

  • 4% Above List Price
  • $153/SF
  • 45 Days On Market

  Current Estimated Value $294,326

  Last Listing Agent Joan Oricchio Berkshire Hathaway NE Prop.

  6 Hickory Ln Unit 6, Woodbury, CT 06798
• 

  Est $703,084 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 2,507 Sq Ft

  11 Hillview Ln, Woodbury, CT 06798

  11 Hillview Ln, Woodbury, CT 06798
• 

  $776,400 Sold Apr 02, 2025

  896 Main St S, Woodbury, CT 06798

  • 3 Beds
  • 4.5 Baths
  • 3,367 Sq Ft
  • Built 1958

  Last Sold Summary

  • $231/SF
  • 33 Days On Market

  Current Estimated Value $786,294

  Last Listing Agent Heather Crabtree RE/MAX RISE

  896 Main St S, Woodbury, CT 06798
• 

  Est $564,055 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,299 Sq Ft

  42 Middle Quarter Rd, Woodbury, CT 06798

  42 Middle Quarter Rd, Woodbury, CT 06798
• 

  $430,000 Sold Oct 29, 2025

  31 Woodbury Hill, Woodbury, CT 06798

  • 2 Beds
  • 1.5 Baths
  • 1,502 Sq Ft
  • Built 1985

  Last Sold Summary

  • 9% Below List Price
  • $286/SF
  • 175 Days On Market

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

  31 Woodbury Hill, Woodbury, CT 06798
• 

  Est $605,223 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 2,042 Sq Ft

  27 Middle Quarter Rd, Woodbury, CT 06798

  27 Middle Quarter Rd, Woodbury, CT 06798

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