5,007

Woodbury, CT Homes

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  • 4 Hazel Plain Rd, Woodbury, CT 06798

    $370,000

    Sold Nov 18, 2025

    4 Hazel Plain Rd, Woodbury, CT 06798

    • 3 Beds
    • 1 Bath
    • 1,075 Sq Ft
    • Built 1949

    Last Sold Summary

    • 8% Above List Price
    • $344/SF
    • 6 Days On Market

    Current Estimated Value $371,326

    Last Listing Agent Gary Smith eXp Realty

    4 Hazel Plain Rd, Woodbury, CT 06798
  • 9 Upper Commons Unit 9, Woodbury, CT 06798
    9 Upper Commons Unit 9, Woodbury, CT 06798
    9 Upper Commons Unit 9, Woodbury, CT 06798
    /38

    $279,900

    $10K PRICE DROP Under Contract
    • 2 Beds
    • 2 Baths
    • 1,457 Sq Ft

    9 Upper Commons Unit 9, Woodbury, CT 06798

    Welcome to 9 Upper Commons, Woodbury - Tucked away in a quiet, well-maintained community surrounded by mature trees and walking trails, this inviting 2-bedroom townhouse offers three levels for a comfortable, functional lifestyle. The main level features a spacious open-concept floor plan, ideal for everyday living or entertaining. Sliding doors off the dining area leads to your private

    Athan Zeno William Raveis Real Estate

    9 Upper Commons Unit 9, Woodbury, CT 06798
  • 59 Arrowhead Way, Woodbury, CT 06798

    $385,000

    Sold Jul 02, 2025

    59 Arrowhead Way, Woodbury, CT 06798

    • 5 Beds
    • 2 Baths
    • 1,693 Sq Ft
    • Built 1964

    Last Sold Summary

    • 4% Below List Price
    • $227/SF
    • 26 Days On Market

    Current Estimated Value $391,678

    Last Listing Agent Shawna Mucherino Coldwell Banker Realty

    59 Arrowhead Way, Woodbury, CT 06798
  • 54 School St, Woodbury, CT 06798
    54 School St, Woodbury, CT 06798
    54 School St, Woodbury, CT 06798
    /37

    $589,000

    Pending
    • 3 Beds
    • 1.5 Baths
    • 2,148 Sq Ft

    54 School St, Woodbury, CT 06798

    Timeless Elegance in the Heart of the Historic District . Step back in time without sacrificing modern convenience in this enchanting 1750s colonial, perfectly situated on a premier corner lot within the town's coveted Historic District. This home isn't just a place to live; it's a piece of local history loaded with "old world" character. From the moment you step inside, the rich wide plank

    Carla Mascaro William Pitt Sotheby's Int'l

    54 School St, Woodbury, CT 06798
  • 14 Tamarack Ln, Woodbury, CT 06798

    $261,000

    Sold May 21, 2026

    14 Tamarack Ln, Woodbury, CT 06798

    • 2 Beds
    • 2.5 Baths
    • 1,983 Sq Ft
    • Built 1974

    Last Sold Summary

    • 1% Above List Price
    • $132/SF
    • 99 Days On Market

    Current Estimated Value $250,470

    Last Listing Agent Gina Jacobs Gina Jacobs Real Estate

    14 Tamarack Ln, Woodbury, CT 06798
  • 8 Curtiss Meadows, Woodbury, CT 06798
    8 Curtiss Meadows, Woodbury, CT 06798
    8 Curtiss Meadows, Woodbury, CT 06798
    /40

    $899,000

    Open Sun 12PM - 2PM $51K PRICE DROP
    • 4 Beds
    • 5 Baths
    • 3,865 Sq Ft

    8 Curtiss Meadows, Woodbury, CT 06798

    Beautiful Colonial set on a private 3+ acre lot in sought-after Curtiss Meadows, ideally located on the southern end of Woodbury abutting the Southbury line. Set back from the cul-de-sac entryway, this well-cared-for home offers a wonderful blend of privacy, comfort, convenience, and thoughtful updates. The level, light-filled driveway provides easy access, while the peaceful setting creates a

    Joyce Drakeley Drakeley Real Estate, Inc.

    8 Curtiss Meadows, Woodbury, CT 06798
  • 59 Davids Hill Rd, Woodbury, CT 06798

    $805,000

    Sold Aug 07, 2025

    59 Davids Hill Rd, Woodbury, CT 06798

    • 4 Beds
    • 2.5 Baths
    • 2,475 Sq Ft
    • Built 1979

    Last Sold Summary

    • 6% Above List Price
    • $325/SF
    • 16 Days On Market

    Current Estimated Value $814,990

    Last Listing Agent Maria Taylor Klemm Real Estate Inc

    59 Davids Hill Rd, Woodbury, CT 06798
  • 55 Good Hill Rd, Woodbury, CT 06798
    55 Good Hill Rd, Woodbury, CT 06798
    55 Good Hill Rd, Woodbury, CT 06798
    /40

    $1,995,000

    • 4 Beds
    • 4.5 Baths
    • 3,324 Sq Ft

    55 Good Hill Rd, Woodbury, CT 06798

    Step into History with Modern Comfort Experience the undeniable charm of this circa 1685 residence-one of the oldest continuously inhabited homes in the county. Thoughtfully restored and beautifully updated, this remarkable property blends centuries of character with today's modern conveniences. Inside, the open floor plan creates a warm and inviting flow, with three cozy sitting rooms

    Stacey Matthews W. Raveis Lifestyles Realty

    55 Good Hill Rd, Woodbury, CT 06798
  • 43 Woodbury Hill, Woodbury, CT 06798

    $430,000

    Sold Jun 22, 2026

    43 Woodbury Hill, Woodbury, CT 06798

    • 2 Beds
    • 2 Baths
    • 1,986 Sq Ft
    • Built 1985

    Last Sold Summary

    • 28% Below List Price
    • $217/SF
    • 54 Days On Market

    Current Estimated Value $449,228

    Last Listing Agent Joyce Drakeley Drakeley Real Estate, Inc.

    43 Woodbury Hill, Woodbury, CT 06798
  • 19 Hillview Ln, Woodbury, CT 06798
    19 Hillview Ln, Woodbury, CT 06798
    19 Hillview Ln, Woodbury, CT 06798
    /40

    $749,000

    Under Contract
    • 3 Beds
    • 3.5 Baths
    • 3,749 Sq Ft

    19 Hillview Ln, Woodbury, CT 06798

    Nestled within the exclusive South Brook community, 19 Hill View Lane offers timeless New England charm paired with exceptional craftsmanship. This beautifully appointed 3 bedroom, 3.5 bath cape colonial is rich in architectural detail, featuring refined millwork, quality finishes, and a thoughtful layout designed for both everyday living and elegant entertaining. The main living spaces flow

    Nicole Fiorelli Fiorelli Realty, LLC

    19 Hillview Ln, Woodbury, CT 06798
  • 74 Woodbury Hill, Woodbury, CT 06798

    $489,000

    Sold Apr 30, 2026

    74 Woodbury Hill, Woodbury, CT 06798

    • 2 Beds
    • 2.5 Baths
    • 2,463 Sq Ft
    • Built 1985

    Last Sold Summary

    • $199/SF
    • 15 Days On Market

    Current Estimated Value $491,247

    Last Listing Agent Claudine McHugh Klemm Real Estate Inc

    74 Woodbury Hill, Woodbury, CT 06798
  • 229 Bacon Pond Rd Unit 312, Woodbury, CT 06798

    $120,000

    Sold Jun 05, 2026

    229 Bacon Pond Rd Unit 312, Woodbury, CT 06798

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

    Last Sold Summary

    • 25% Below List Price
    • $131/SF
    • 129 Days On Market

    Current Estimated Value $157,090

    Last Listing Agent Ron Nettleton William Raveis Real Estate

    229 Bacon Pond Rd Unit 312, Woodbury, CT 06798
  • 14 Arrowhead Way Unit 1, Woodbury, CT 06798

    $130,000

    Sold Jul 16, 2025

    14 Arrowhead Way Unit 1, Woodbury, CT 06798

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

    Last Sold Summary

    • 4% Below List Price
    • $238/SF
    • 43 Days On Market

    Current Estimated Value $128,663

    Last Listing Agent Jeff Boucher Drakeley Real Estate, Inc.

    14 Arrowhead Way Unit 1, Woodbury, CT 06798
  • 223 Tuttle Rd, Woodbury, CT 06798

    $420,000

    Sold Nov 19, 2025

    223 Tuttle Rd, Woodbury, CT 06798

    • 2 Beds
    • 1 Bath
    • 1,328 Sq Ft
    • Built 1956

    Last Sold Summary

    • 6% Below List Price
    • $316/SF
    • 14 Days On Market

    Current Estimated Value $422,568

    Last Listing Agent Rhya Szymansky Drakeley Real Estate, Inc.

    223 Tuttle Rd, Woodbury, CT 06798
    • 3 Fox Run, Woodbury, CT 06798

      Est $320,943

      Not Listed For Sale

      3 Fox Run, Woodbury, CT 06798

      • 3 Beds
      • 2.5 Baths
      • 2,440 Sq Ft
      • Built 1980
      3 Fox Run, Woodbury, CT 06798

      Last Sold Summary

      • 37 Days On Market

  • 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 $280,709

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

    48 Clubhouse Dr, Woodbury, CT 06798
    • 16 Saxony Ln, Woodbury, CT 06798

      Est $830,020

      Not Listed For Sale

      16 Saxony Ln, Woodbury, CT 06798

      • 3 Beds
      • 3.5 Baths
      • 3,110 Sq Ft
      • Built 2000
      16 Saxony Ln, Woodbury, CT 06798

      Last Sold Summary

      • 37 Days On Market

  • 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

    Current Estimated Value $419,433

    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 $231,603

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

    6 Deer Hill Ct, Woodbury, CT 06798
  • 393 Middle Road Turnpike, Woodbury, CT 06798

    $765,000

    Sold Dec 22, 2025

    393 Middle Road Turnpike, Woodbury, CT 06798

    • 4 Beds
    • 4 Baths
    • 3,280 Sq Ft
    • Built 1783

    Last Sold Summary

    • 15% Below List Price
    • $233/SF
    • 96 Days On Market

    Current Estimated Value $769,023

    Last Listing Agent Kathryn Bassett William Pitt Sotheby's Int'l

    393 Middle Road Turnpike, 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

    Current Estimated Value $508,839

    Last Listing Agent Stephanie Chapman BHGRE Gaetano Marra Homes

    17 Old Flanders Rd, Woodbury, CT 06798
    • 6 Mill Rd, Woodbury, CT 06798

      Est $883,472

      Not Listed For Sale

      6 Mill Rd, Woodbury, CT 06798

      • 3 Beds
      • 3 Baths
      • 1,892 Sq Ft
      • Built 1870
      6 Mill Rd, Woodbury, CT 06798

      Last Sold Summary

      • 14 Days On Market

  • 90 Rowley Rd, Woodbury, CT 06798

    $325,000

    Sold Apr 10, 2026

    90 Rowley Rd, Woodbury, CT 06798

    • 4 Beds
    • 4 Baths
    • 2,695 Sq Ft
    • Built 1830

    Last Sold Summary

    • 13% Below List Price
    • $121/SF
    • 95 Days On Market

    Current Estimated Value $363,138

    Last Listing Agent Mikaila Riedel eXp Realty

    90 Rowley Rd, Woodbury, CT 06798
    • 130 Sage Rd, Woodbury, CT 06798

      Est $587,645

      Not Listed For Sale

      130 Sage Rd, Woodbury, CT 06798

      • 3 Beds
      • 3 Baths
      • 2,113 Sq Ft
      • Built 1985
      130 Sage Rd, Woodbury, CT 06798

      Last Sold Summary

      • 44 Days On Market

  • 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

    Current Estimated Value $178,939

    Last Listing Agent Tim Drakeley Drakeley Real Estate, Inc.

    229 Bacon Pond Rd Unit 322, Woodbury, CT 06798
  • 35 Coach Light Dr, Woodbury, CT 06798

    $925,000

    Sold Apr 16, 2026

    35 Coach Light Dr, Woodbury, CT 06798

    • 4 Beds
    • 5.5 Baths
    • 5,114 Sq Ft
    • Built 1999

    Last Sold Summary

    • $181/SF
    • 6 Days On Market

    Current Estimated Value $929,116

    Last Listing Agent Maria Taylor Klemm Real Estate Inc

    35 Coach Light Dr, Woodbury, CT 06798
  • 4 Fox Run Unit 4, Woodbury, CT 06798

    $288,500

    Sold May 01, 2026

    4 Fox Run Unit 4, Woodbury, CT 06798

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

    Last Sold Summary

    • 4% Below List Price
    • $244/SF
    • 151 Days On Market

    Last Listing Agent Henrik K Kjaer Keller Williams Realty

    4 Fox Run Unit 4, Woodbury, CT 06798

Showing Results 201 - 240, Page 6 of 18

Connecticut Litchfield County Woodbury

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