161

Recently Sold Woodbury, CT Homes

Section Image
  • 48 Clubhouse Dr, Woodbury, CT 06798

    $270,000 Sold Sep 19, 2025

    48 Clubhouse Dr, Woodbury, CT 06798

    • 2 Beds
    • 2.5 Baths
    • 1,316 Sq Ft
    • Built 1972

    Last Sold Summary

    • 4% Below List Price
    • $205/SF
    • 40 Days On Market

    Current Estimated Value $269,193

    Last Listing Agent Taylor O'Keefe Drakeley Real Estate, Inc.

    48 Clubhouse Dr, Woodbury, CT 06798
  • 60 Pomperaug Rd, Woodbury, CT 06798

    $415,000 Sold Oct 31, 2025

    60 Pomperaug Rd, Woodbury, CT 06798

    • 4 Beds
    • 2.5 Baths
    • 1,668 Sq Ft
    • Built 1850

    Last Sold Summary

    • 10% Below List Price
    • $249/SF
    • 128 Days On Market

    Last Listing Agent Terry Lee Adams Adams & Adams Real Estate

    60 Pomperaug Rd, Woodbury, CT 06798
  • 6 Deer Hill Ct, Woodbury, CT 06798

    $214,000 Sold Jul 18, 2025

    6 Deer Hill Ct, Woodbury, CT 06798

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

    Last Sold Summary

    • $181/SF
    • 42 Days On Market

    Current Estimated Value $232,072

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

    6 Deer Hill Ct, Woodbury, CT 06798
  • 17 Old Flanders Rd, Woodbury, CT 06798

    $490,000 Sold Nov 18, 2025

    17 Old Flanders Rd, Woodbury, CT 06798

    • 3 Beds
    • 2.5 Baths
    • 1,874 Sq Ft
    • Built 1986

    Last Sold Summary

    • 3% Above List Price
    • $261/SF
    • 28 Days On Market

    Last Listing Agent Stephanie Chapman Scalzo Real Estate

    17 Old Flanders Rd, Woodbury, CT 06798
  • 229 Bacon Pond Rd Unit 322, Woodbury, CT 06798

    $174,900 Sold Oct 10, 2025

    229 Bacon Pond Rd Unit 322, Woodbury, CT 06798

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

    Last Sold Summary

    • 5% Below List Price
    • $192/SF
    • 122 Days On Market

    Last Listing Agent Tim Drakeley Drakeley Real Estate, Inc.

    229 Bacon Pond Rd Unit 322, Woodbury, CT 06798
  • 24 Roxbury Rd, Woodbury, CT 06798

    $769,000 Sold Apr 01, 2025

    24 Roxbury Rd, Woodbury, CT 06798

    • 3 Beds
    • 2.5 Baths
    • 4,012 Sq Ft
    • Built 1987

    Last Sold Summary

    • 38% Below List Price
    • $192/SF
    • 313 Days On Market

    Current Estimated Value $1,150,846

    Last Listing Agent Debbie Kranidis Preston Gray Real Estate

    24 Roxbury Rd, Woodbury, CT 06798
  • 229 Bacon Pond Rd Unit 233, Woodbury, CT 06798

    $182,500 Sold Apr 02, 2025

    229 Bacon Pond Rd Unit 233, Woodbury, CT 06798

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

    Last Sold Summary

    • 1% Below List Price
    • $200/SF
    • 142 Days On Market

    Current Estimated Value $186,854

    Last Listing Agent Joe Dimyan Tower Realty Corp

    229 Bacon Pond Rd Unit 233, Woodbury, CT 06798
  • 118 Good Hill Rd, Woodbury, CT 06798

    $750,000 Sold Dec 10, 2025

    118 Good Hill Rd, Woodbury, CT 06798

    • 4 Beds
    • 2.5 Baths
    • 3,196 Sq Ft
    • Built 2002

    Last Sold Summary

    • 6% Below List Price
    • $235/SF
    • 62 Days On Market

    Last Listing Agent Tim Drakeley Drakeley Real Estate, Inc.

    118 Good Hill Rd, Woodbury, CT 06798
  • 54 Barbara Ln, Woodbury, CT 06798

    $470,000 Sold Jan 08, 2025

    54 Barbara Ln, Woodbury, CT 06798

    • 3 Beds
    • 2.5 Baths
    • 2,901 Sq Ft
    • Built 1959

    Last Sold Summary

    • 6% Below List Price
    • $162/SF
    • 36 Days On Market

    Current Estimated Value $483,698

    Last Listing Agent Tim Drakeley Drakeley Real Estate, Inc.

    54 Barbara Ln, Woodbury, CT 06798
  • 229 Bacon Pond Rd Unit 113, Woodbury, CT 06798

    $175,000 Sold Oct 29, 2025

    229 Bacon Pond Rd Unit 113, Woodbury, CT 06798

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

    Last Sold Summary

    • 6% Above List Price
    • $192/SF
    • 8 Days On Market

    Last Listing Agent Alex Rodrigues RE/MAX RISE

    229 Bacon Pond Rd Unit 113, Woodbury, CT 06798
  • 220 Church Hill Rd, Woodbury, CT 06798

    $1,075,000 Sold Aug 29, 2025

    220 Church Hill Rd, Woodbury, CT 06798

    • 3 Beds
    • 3.5 Baths
    • 4,632 Sq Ft
    • Built 1997

    Last Sold Summary

    • 14% Below List Price
    • $232/SF
    • 51 Days On Market

    Current Estimated Value $1,068,772

    Last Listing Agent MaryBeth White William Raveis Real Estate

    220 Church Hill Rd, Woodbury, CT 06798
  • 51 Joshua Hill Rd, Woodbury, CT 06798

    $297,500 Sold Apr 30, 2025

    51 Joshua Hill Rd, Woodbury, CT 06798

    • 3 Beds
    • 1.5 Baths
    • 1,508 Sq Ft
    • Built 1960

    Last Sold Summary

    • 10% Below List Price
    • $197/SF
    • 10 Days On Market

    Current Estimated Value $323,441

    Last Listing Agent Sarah Perrotti Regency Real Estate, LLC

    51 Joshua Hill Rd, Woodbury, CT 06798
  • 5 Bear Run, Woodbury, CT 06798

    $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
  • 29 Lighthouse 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
  • 77 Northgate 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
  • 1 Woods Way Unit 118E, 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
  • 49 Woods Way, 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
  • 301 Transylvania 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
  • 1 Summit Ct Unit 1, 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
  • 229 Bacon Pond Rd Unit 352, 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
  • 7 Orenaug Ave, 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
  • 173 Railtree Hill Rd, 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
  • 229 Bacon Pond Rd Unit 411, 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
  • 447 Transylvania Rd, 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
  • 40 Quanopaug Trail, 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
  • 130 Grassy Hill Rd, 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
  • 229 Bacon Pond Rd Unit 132, 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
  • 29 Woods Way, 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
  • 181 Railtree Hill Rd, 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
  • 6 Hickory Ln Unit 6, 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
  • 896 Main St S, 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
  • 31 Woodbury Hill, 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
  • 101 Railtree Hill Rd, Woodbury, CT 06798

    $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
  • 172 Good Hill 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
  • 431 Sherman Hill Rd, 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
  • 16 Pilgrim Trail Unit 6, 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
  • 382 Weekeepeemee Rd, 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
  • 163 Washington Rd, Woodbury, CT 06798

    $430,000 Sold Apr 04, 2025

    163 Washington Rd, Woodbury, CT 06798

    • 4 Beds
    • 3 Baths
    • 2,521 Sq Ft
    • Built 1836

    Last Sold Summary

    • 5% Below List Price
    • $171/SF
    • 162 Days On Market

    Current Estimated Value $443,569

    Last Listing Agent Katherine Parlato Drakeley Real Estate, Inc.

    163 Washington Rd, Woodbury, CT 06798
  • 35 Weekeepeemee Rd, 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
  • 133 Hoop Pole Hill Rd, 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

Showing Results 81 - 120, Page 3 of 5

Connecticut Litchfield County Woodbury

Recently Sold Real Estate & Homes in Woodbury, CT

How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2025 CoStar Group