5,007

Woodbury, CT Homes

Section Image
    • Lot 2 Grassy Hill Rd, Woodbury, CT 06798

      Not Listed For Sale

      Lot 2 Grassy Hill Rd, Woodbury, CT 06798

      Lot 2 Grassy Hill Rd, Woodbury, CT 06798

      Last Sold Summary

      • 230 Days On Market
      • Last Sold Price $140,000
      • Feb 29, 2024

      Last Listing Agent Maria Taylor Klemm Real Estate Inc

    • Lot 1 Grassy Hill Rd, Woodbury, CT 06798

      Not Listed For Sale

      Lot 1 Grassy Hill Rd, Woodbury, CT 06798

      Lot 1 Grassy Hill Rd, Woodbury, CT 06798

      Last Sold Summary

      • 148 Days On Market
      • Last Sold Price $150,000
      • Jan 09, 2024

      Last Listing Agent Maria Taylor Klemm Real Estate Inc

    • 4 North Meadows Unit 110D, Woodbury, CT 06798

      Not Listed For Sale

      4 North Meadows Unit 110D, Woodbury, CT 06798

      • 2 Beds
      • 2.5 Baths
      • 1,456 Sq Ft
      • Built 1979
      4 North Meadows Unit 110D, Woodbury, CT 06798

      Last Sold Summary

      • $206/SF
      • 33 Days On Market
      • Last Sold Price $299,900
      • Aug 25, 2023

      Last Listing Agent Ginny McKinney Berkshire Hathaway Home Services

    • 269 Westwood Rd, Woodbury, CT 06798

      Est $465,146 Not Listed For Sale

      269 Westwood Rd, Woodbury, CT 06798

      • 2 Beds
      • 1 Bath
      • 1,800 Sq Ft
      • Built 2008
      269 Westwood Rd, Woodbury, CT 06798

      Last Sold Summary

      • 8% Above List Price
      • $239/SF
      • 14 Days On Market
      • Last Sold Price $430,000
      • Sep 20, 2023

      Last Listing Agent Richard Pomerantz William Pitt

    • 24 Meadow Crest Dr, Woodbury, CT 06798

      Est $155,818 Not Listed For Sale

      24 Meadow Crest Dr, Woodbury, CT 06798

      24 Meadow Crest Dr, Woodbury, CT 06798

      Last Sold Summary

      • 1% Above List Price
      • 52 Days On Market
      • Last Sold Price $155,000
      • Jul 25, 2024

      Last Listing Agent Maria Taylor Klemm Real Estate Inc

    • 26 Fox Run Unit 26, Woodbury, CT 06798

      Not Listed For Sale

      26 Fox Run Unit 26, Woodbury, CT 06798

      • 2 Beds
      • 2.5 Baths
      • 1,851 Sq Ft
      • Built 1980
      26 Fox Run Unit 26, Woodbury, CT 06798

      Last Sold Summary

      • $138/SF
      • 1 Day On Market
      • Last Sold Price $255,000
      • May 05, 2023

      Last Listing Agent Alexander Marti Showcase Realty, Inc.

    • 00 Tuttle Rd, Woodbury, CT 06798

      Not Listed For Sale

      00 Tuttle Rd, Woodbury, CT 06798

      00 Tuttle Rd, Woodbury, CT 06798

      Last Sold Summary

      • 139 Days On Market
      • Last Sold Price $80,000
      • Aug 31, 2023

      Last Listing Agent Bethany Lydem Stone Crest Realty LLC

    • 7 Lower Commons Unit 7, Woodbury, CT 06798

      Est $322,550 Not Listed For Sale

      7 Lower Commons Unit 7, Woodbury, CT 06798

      • 3 Beds
      • 2.5 Baths
      • 1,640 Sq Ft
      • Built 1980
      7 Lower Commons Unit 7, Woodbury, CT 06798

      Last Sold Summary

      • 22% Above List Price
      • $162/SF
      • 42 Days On Market
      • Last Sold Price $265,000
      • Nov 17, 2023

      Last Listing Agent Rhya Szymansky Drakeley Real Estate, Inc.

    • 170 Brushy Hill Rd, Woodbury, CT 06798

      Est $707,000 Not Listed For Sale

      170 Brushy Hill Rd, Woodbury, CT 06798

      170 Brushy Hill Rd, Woodbury, CT 06798

      Last Sold Summary

      • 401% Above List Price
      • 7 Days On Market
      • Last Sold Price $141,000
      • Jul 25, 2024

      Last Listing Agent Paul Ferreira RE/MAX

    • 13 Clubhouse Dr Unit 22B, Woodbury, CT 06798

      Est $305,986 Not Listed For Sale

      13 Clubhouse Dr Unit 22B, Woodbury, CT 06798

      • 2 Beds
      • 3.5 Baths
      • 1,762 Sq Ft
      • Built 1972
      13 Clubhouse Dr Unit 22B, Woodbury, CT 06798

      Last Sold Summary

      • 10% Above List Price
      • $157/SF
      • 70 Days On Market
      • Last Sold Price $277,000
      • Jul 28, 2023

      Last Listing Agent Derek Savoy Coldwell Banker Realty

    • 45 S Pomperaug Ave, Woodbury, CT 06798

      Est $918,211 Not Listed For Sale

      45 S Pomperaug Ave, Woodbury, CT 06798

      • 4 Beds
      • 2.5 Baths
      • 3,192 Sq Ft
      • Built 2024
      45 S Pomperaug Ave, Woodbury, CT 06798

      Last Sold Summary

      • 9% Above List Price
      • $263/SF
      • 7 Days On Market
      • Last Sold Price $840,000
      • May 22, 2024

      Last Listing Agent Alex De Camargo eXp Realty

    • 29 Fawn Meadow Ln, Woodbury, CT 06798

      Est $781,963 Not Listed For Sale

      29 Fawn Meadow Ln, Woodbury, CT 06798

      • 4 Beds
      • 2.5 Baths
      • 2,042 Sq Ft
      • Built 2022
      29 Fawn Meadow Ln, Woodbury, CT 06798

      Last Sold Summary

      • 6% Above List Price
      • $360/SF
      • 45 Days On Market
      • Last Sold Price $735,000
      • Apr 14, 2025

      Last Listing Agent Gregory Cohen William Pitt

    • 225 Orchard Ave, Woodbury, CT 06798

      Est $641,253 Not Listed For Sale

      225 Orchard Ave, Woodbury, CT 06798

      • 3 Beds
      • Built 2024
      225 Orchard Ave, Woodbury, CT 06798

      Last Sold Summary

      • 413% Above List Price
      • $54/SF
      • 37 Days On Market
      • Last Sold Price $125,000
      • May 12, 2023

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

    • 10 Pilgrim Trail Unit D8 Bldg 31, Woodbury, CT 06798

      Not Listed For Sale

      10 Pilgrim Trail Unit D8 Bldg 31, Woodbury, CT 06798

      • 1 Bed
      • 1 Bath
      • 546 Sq Ft
      • Built 1965
      10 Pilgrim Trail Unit D8 Bldg 31, Woodbury, CT 06798

      Last Sold Summary

      • $229/SF
      • 73 Days On Market
      • Last Sold Price $125,000
      • Jul 22, 2024

      Last Listing Agent Kari Rustici Coldwell Banker Realty

    • 88 Tuttle Rd, Woodbury, CT 06798

      Not Listed For Sale

      88 Tuttle Rd, Woodbury, CT 06798

      88 Tuttle Rd, Woodbury, CT 06798

      Last Sold Summary

      • 7% Above List Price
      • 35 Days On Market
      • Last Sold Price $100,000
      • Sep 30, 2024

      Last Listing Agent Wendy Brazauskas Coldwell Banker Realty

    • 23 Upper Commons Unit 23, Woodbury, CT 06798

      Not Listed For Sale

      23 Upper Commons Unit 23, Woodbury, CT 06798

      • 2 Beds
      • 2 Baths
      • 1,182 Sq Ft
      • Built 1980
      23 Upper Commons Unit 23, Woodbury, CT 06798

      Last Sold Summary

      • $191/SF
      • 19 Days On Market
      • Last Sold Price $226,000
      • Dec 28, 2022

      Last Listing Agent Chris LaCava Coldwell Banker Realty

    • 16 Clubhouse Dr Unit 16, Woodbury, CT 06798

      Not Listed For Sale

      16 Clubhouse Dr Unit 16, Woodbury, CT 06798

      • 2 Beds
      • 2.5 Baths
      • 1,996 Sq Ft
      • Built 1972
      16 Clubhouse Dr Unit 16, Woodbury, CT 06798

      Last Sold Summary

      • $111/SF
      • 22 Days On Market
      • Last Sold Price $221,000
      • Nov 03, 2021

      Last Listing Agent Dayna Shliger Coldwell Banker Realty

    • 4 Main St S, Woodbury, CT 06798

      Est $320,072 Not Listed For Sale

      4 Main St S, Woodbury, CT 06798

      • 2 Beds
      • 1 Bath
      • 2,976 Sq Ft
      • Built 1920
      4 Main St S, Woodbury, CT 06798

      Last Sold Summary

      • 23% Above List Price
      • $87/SF
      • 108 Days On Market
      • Last Sold Price $260,000
      • Mar 18, 2022

      Last Listing Agent Tim Drakeley Drakeley Real Estate, Inc.

    • 125 Main St S, Woodbury, CT 06798

      Est $550,693 Not Listed For Sale

      125 Main St S, Woodbury, CT 06798

      • 5 Beds
      • 4 Baths
      • 3,733 Sq Ft
      • Built 1800
      125 Main St S, Woodbury, CT 06798

      Last Sold Summary

      • 36% Above List Price
      • $108/SF
      • 21 Days On Market
      • Last Sold Price $405,000
      • Sep 30, 2021

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

    • 305 Main St S, Woodbury, CT 06798

      Est $691,342 Not Listed For Sale

      305 Main St S, Woodbury, CT 06798

      • 3 Beds
      • 3 Baths
      • 2,015 Sq Ft
      • Built 1835
      305 Main St S, Woodbury, CT 06798

      Last Sold Summary

      • 16% Above List Price
      • $295/SF
      • 99 Days On Market
      • Last Sold Price $595,000
      • Sep 26, 2022

      Last Listing Agent Robert Drakeley Robert J. Drakeley, Broker

    • 10 Upper Commons Unit 103D, Woodbury, CT 06798

      Not Listed For Sale

      10 Upper Commons Unit 103D, Woodbury, CT 06798

      • 3 Beds
      • 2.5 Baths
      • 1,467 Sq Ft
      • Built 1980
      10 Upper Commons Unit 103D, Woodbury, CT 06798

      Last Sold Summary

      • $153/SF
      • 108 Days On Market
      • Last Sold Price $225,000
      • Feb 17, 2022

      Last Listing Agent Sandra Schmidt Coldwell Banker Realty

    • 8 Stone Hollow Rd, Woodbury, CT 06798

      Est $1,343,265 Not Listed For Sale

      8 Stone Hollow Rd, Woodbury, CT 06798

      • 4 Beds
      • 3.5 Baths
      • 4,050 Sq Ft
      • Built 2007
      8 Stone Hollow Rd, Woodbury, CT 06798

      Last Sold Summary

      • 5% Above List Price
      • $315/SF
      • 36 Days On Market
      • Last Sold Price $1,275,000
      • Jul 27, 2022

      Last Listing Agent Kathryn Clair William Pitt

    • 556 Flanders Rd, Woodbury, CT 06798

      Est $1,130,909 Not Listed For Sale

      556 Flanders Rd, Woodbury, CT 06798

      • 5 Beds
      • 3.5 Baths
      • 5,403 Sq Ft
      • Built 2007
      556 Flanders Rd, Woodbury, CT 06798

      Last Sold Summary

      • 29% Above List Price
      • $163/SF
      • 111 Days On Market
      • Last Sold Price $880,000
      • Feb 01, 2022

      Last Listing Agent Tim Drakeley Drakeley Real Estate, Inc.

    • 115 Flanders Rd, Woodbury, CT 06798

      Est $765,565 Not Listed For Sale

      115 Flanders Rd, Woodbury, CT 06798

      • 3 Beds
      • 2.5 Baths
      • 1,927 Sq Ft
      • Built 1995
      115 Flanders Rd, Woodbury, CT 06798

      Last Sold Summary

      • 37% Above List Price
      • $291/SF
      • 22 Days On Market
      • Last Sold Price $560,000
      • Dec 17, 2021

      Last Listing Agent Sandra Ramalhete Real Estate Two

    • 481 Good Hill Rd, Woodbury, CT 06798

      Est $420,246 Not Listed For Sale

      481 Good Hill Rd, Woodbury, CT 06798

      • 1 Bed
      • 1 Bath
      • 748 Sq Ft
      • Built 1935
      481 Good Hill Rd, Woodbury, CT 06798

      Last Sold Summary

      • 31% Above List Price
      • $428/SF
      • 108 Days On Market
      • Last Sold Price $320,000
      • May 13, 2022

      Last Listing Agent Caroline Bailey Coldwell Banker Realty

    • 107 Stagecoach Rd, Woodbury, CT 06798

      Est $797,194 Not Listed For Sale

      107 Stagecoach Rd, Woodbury, CT 06798

      • 4 Beds
      • 2.5 Baths
      • 3,060 Sq Ft
      • Built 2000
      107 Stagecoach Rd, Woodbury, CT 06798

      Last Sold Summary

      • 33% Above List Price
      • $196/SF
      • 55 Days On Market
      • Last Sold Price $600,000
      • Aug 17, 2022

      Last Listing Agent Joyce Drakeley Drakeley Real Estate, Inc.

    • 344 Weekeepeemee Rd, Woodbury, CT 06798

      Est $1,034,017 Not Listed For Sale

      344 Weekeepeemee Rd, Woodbury, CT 06798

      • 5 Beds
      • 5 Baths
      • 5,571 Sq Ft
      • Built 2001
      344 Weekeepeemee Rd, Woodbury, CT 06798

      Last Sold Summary

      • 67% Above List Price
      • $111/SF
      • 97 Days On Market
      • Last Sold Price $618,000
      • Sep 02, 2021

      Last Listing Agent Christopher Lawrence Trillionaire Realty

    • 148 Great Hollow Rd, Woodbury, CT 06798

      Est $880,280 Not Listed For Sale

      148 Great Hollow Rd, Woodbury, CT 06798

      • 3 Beds
      • 2.5 Baths
      • 2,820 Sq Ft
      • Built 1970
      148 Great Hollow Rd, Woodbury, CT 06798

      Last Sold Summary

      • 41% Above List Price
      • $222/SF
      • 21 Days On Market
      • Last Sold Price $625,000
      • Sep 30, 2021

      Last Listing Agent Justin Bette Century 21 Bette Real Estate

    • 181 Joshua Hill Rd, Woodbury, CT 06798

      Est $1,306,906 Not Listed For Sale

      181 Joshua Hill Rd, Woodbury, CT 06798

      • 4 Beds
      • 2 Baths
      • 2,726 Sq Ft
      • Built 1750
      181 Joshua Hill Rd, Woodbury, CT 06798

      Last Sold Summary

      • 14% Above List Price
      • $422/SF
      • 18 Days On Market
      • Last Sold Price $1,150,000
      • Aug 22, 2022

      Last Listing Agent Kathryn Clair William Pitt

    • 109 Sage Rd, Woodbury, CT 06798

      Est $811,221 Not Listed For Sale

      109 Sage Rd, Woodbury, CT 06798

      • 3 Beds
      • 2.5 Baths
      • 2,057 Sq Ft
      • Built 1966
      109 Sage Rd, Woodbury, CT 06798

      Last Sold Summary

      • 6% Above List Price
      • $372/SF
      • 29 Days On Market
      • Last Sold Price $765,000
      • Nov 30, 2021

      Last Listing Agent Christian Jensen William Pitt

    • 452 Middle Road Turnpike, Woodbury, CT 06798

      Est $1,434,403 Not Listed For Sale

      452 Middle Road Turnpike, Woodbury, CT 06798

      • 4 Beds
      • 3.5 Baths
      • 4,325 Sq Ft
      • Built 1946
      452 Middle Road Turnpike, Woodbury, CT 06798

      Last Sold Summary

      • 20% Above List Price
      • $277/SF
      • 62 Days On Market
      • Last Sold Price $1,200,000
      • Aug 15, 2022

      Last Listing Agent Maria Taylor Klemm Real Estate Inc

    • 71 Mill Rd, Woodbury, CT 06798

      Est $514,961 Not Listed For Sale

      71 Mill Rd, Woodbury, CT 06798

      • 3 Beds
      • 2 Baths
      • 2,000 Sq Ft
      • Built 2002
      71 Mill Rd, Woodbury, CT 06798

      Last Sold Summary

      • 30% Above List Price
      • $198/SF
      • 5 Days On Market
      • Last Sold Price $395,000
      • Sep 09, 2022

      Last Listing Agent Shelley Drakeley Drakeley Real Estate, Inc.

    • 229 Bacon Pond Rd Unit 152, Woodbury, CT 06798

      Est $173,212 Not Listed For Sale

      229 Bacon Pond Rd Unit 152, Woodbury, CT 06798

      • 2 Beds
      • 1 Bath
      • 913 Sq Ft
      • Built 1971
      229 Bacon Pond Rd Unit 152, Woodbury, CT 06798

      Last Sold Summary

      • 48% Above List Price
      • $128/SF
      • 35 Days On Market
      • Last Sold Price $117,100
      • May 27, 2022

      Last Listing Agent Betsy Rosa Berkshire Hathaway Home Services

    • 45 White Oak Rd, Woodbury, CT 06798

      Est $455,654 Not Listed For Sale

      45 White Oak Rd, Woodbury, CT 06798

      • 4 Beds
      • 1.5 Baths
      • 1,312 Sq Ft
      • Built 1968
      45 White Oak Rd, Woodbury, CT 06798

      Last Sold Summary

      • 47% Above List Price
      • $236/SF
      • 75 Days On Market
      • Last Sold Price $310,000
      • Jun 10, 2021

      Last Listing Agent Ron Nettleton William Raveis Real Estate

    • 12 Pleasant St, Woodbury, CT 06798

      Est $520,290 Not Listed For Sale

      12 Pleasant St, Woodbury, CT 06798

      • 4 Beds
      • 2 Baths
      • 2,030 Sq Ft
      • Built 1926
      12 Pleasant St, Woodbury, CT 06798

      Last Sold Summary

      • 37% Above List Price
      • $187/SF
      • 38 Days On Market
      • Last Sold Price $379,900
      • Jan 06, 2022

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

    • 292 Old Town Farm Rd, Woodbury, CT 06798

      Est $615,533 Not Listed For Sale

      292 Old Town Farm Rd, Woodbury, CT 06798

      • 4 Beds
      • 2.5 Baths
      • 3,930 Sq Ft
      • Built 1989
      292 Old Town Farm Rd, Woodbury, CT 06798

      Last Sold Summary

      • 23% Above List Price
      • $127/SF
      • 152 Days On Market
      • Last Sold Price $500,000
      • Aug 24, 2022

      Last Listing Agent Erika Windisch Keller Williams Prestige Prop.

    • 96 Stagecoach Rd, Woodbury, CT 06798

      Est $606,301 Not Listed For Sale

      96 Stagecoach Rd, Woodbury, CT 06798

      • 4 Beds
      • 2.5 Baths
      • 2,330 Sq Ft
      • Built 1994
      96 Stagecoach Rd, Woodbury, CT 06798

      Last Sold Summary

      • 41% Above List Price
      • $184/SF
      • 40 Days On Market
      • Last Sold Price $428,750
      • Dec 22, 2021

      Last Listing Agent Andy Sachs Compass Connecticut, LLC

    • 1731 Main St N, Woodbury, CT 06798

      Est $603,417 Not Listed For Sale

      1731 Main St N, Woodbury, CT 06798

      • 2 Beds
      • 2 Baths
      • 1,731 Sq Ft
      • Built 1992
      1731 Main St N, Woodbury, CT 06798

      Last Sold Summary

      • 17% Above List Price
      • $298/SF
      • 5 Days On Market
      • Last Sold Price $515,000
      • Oct 20, 2022

      Last Listing Agent Gina Jacobs Gina Jacobs Real Estate

    • 29 Hollow Rd, Woodbury, CT 06798

      Est $520,228 Not Listed For Sale

      29 Hollow Rd, Woodbury, CT 06798

      • 3 Beds
      • 1 Bath
      • 1,879 Sq Ft
      • Built 1850
      29 Hollow Rd, Woodbury, CT 06798

      Last Sold Summary

      • 46% Above List Price
      • $190/SF
      • 231 Days On Market
      • Last Sold Price $356,800
      • Dec 10, 2021

      Last Listing Agent Lisa Titcomb William Pitt

    • 785 Main St N, Woodbury, CT 06798

      Est $705,588 Not Listed For Sale

      785 Main St N, Woodbury, CT 06798

      • 4 Beds
      • 3 Baths
      • 3,984 Sq Ft
      • Built 1770
      785 Main St N, Woodbury, CT 06798

      Last Sold Summary

      • 66% Above List Price
      • $106/SF
      • 137 Days On Market
      • Last Sold Price $424,000
      • Sep 14, 2021

      Last Listing Agent Roberta Allen William Raveis Real Estate

Showing Results 441 - 480, Page 12 of 18

Connecticut Litchfield County Woodbury

Real Estate & Homes

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 © 2026 CoStar Group