4,956

Woodbury, CT Homes

Section Image
  • 16 Fox Run, Woodbury, CT 06798
    16 Fox Run, Woodbury, CT 06798
    16 Fox Run, Woodbury, CT 06798
    /10

    $229,000

    Under Contract
    • 2 Beds
    • 2 Baths
    • 1,813 Sq Ft

    16 Fox Run, Woodbury, CT 06798

    Escape to the feel of a Vermont ski chalet-without leaving Connecticut! This spacious townhome features an open, airy floor plan that's full of potential and just waiting for your personal touch. The flexible main level adapts to your lifestyle, with a sunny breakfast/dining area off the kitchen that also works beautifully as a home office, playroom, or could even be converted into a convenient

    Lisa Briscoe William Raveis Real Estate

    16 Fox Run, Woodbury, CT 06798
  • 9 Hill View Ln, Woodbury, CT 06798

    $500,000

    Sold Mar 09, 2026

    9 Hill View Ln, Woodbury, CT 06798

    • 2 Beds
    • 2.5 Baths
    • 3,362 Sq Ft
    • Built 2004

    Last Sold Summary

    • 7% Below List Price
    • $149/SF
    • 75 Days On Market

    Current Estimated Value $545,601

    Last Listing Agent Christina Zainc BHGRE Gaetano Marra Homes

    9 Hill View Ln, Woodbury, CT 06798
    • 8 MacKay Farm Rd, Woodbury, CT 06798

      Est $580,884

      Not Listed For Sale

      8 MacKay Farm Rd, Woodbury, CT 06798

      • 3 Beds
      • 2 Baths
      • 2,080 Sq Ft
      • Built 1976
      8 MacKay Farm Rd, Woodbury, CT 06798

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Shelley Drakeley Drakeley Real Estate, Inc.

  • 86 Quail Run Rd, Woodbury, CT 06798
    86 Quail Run Rd, Woodbury, CT 06798
    86 Quail Run Rd, Woodbury, CT 06798
    /28

    $765,000

    New Construction $20K PRICE INCREASE
    • 3 Beds
    • 2.5 Baths
    • 2,060 Sq Ft

    86 Quail Run Rd, Woodbury, CT 06798

    QUAIL RUN On the cul de sac - 4 NEW HOMES ALL ON FLAT LOTS! They might be what you have been looking for - SMALLER & SMARTER new homes with PRICES TO MATCH. Beautiful 1 acre+ lots on shared common drives surrounded by 12 ACRES OF PRIVATE OPEN SPACE. This is QUINTESSENTIAL WOODBURY - Quiet, woodsy, and BEAUTIFUL! Construction has begun with completion possible in early October. #86 is a 3 BR, 2.5

    Scott Volpe Coldwell Banker Realty

    86 Quail Run Rd, Woodbury, CT 06798
  • 70 Mountain Rd, Woodbury, CT 06798

    $400,000

    Sold Jan 12, 2026

    70 Mountain Rd, Woodbury, CT 06798

    • 3 Beds
    • 2.5 Baths
    • 2,240 Sq Ft
    • Built 1961

    Last Sold Summary

    • 9% Below List Price
    • $179/SF
    • 57 Days On Market

    Current Estimated Value $439,727

    Last Listing Agent Donna J. Matula William Raveis Real Estate

    70 Mountain Rd, Woodbury, CT 06798
    • 233 Old Sherman Hill Rd, Woodbury, CT 06798

      Est $594,892

      Not Listed For Sale

      233 Old Sherman Hill Rd, Woodbury, CT 06798

      • 3 Beds
      • 2.5 Baths
      • 1,946 Sq Ft
      • Built 1930
      233 Old Sherman Hill Rd, Woodbury, CT 06798

      Last Sold Summary

      • 39 Days On Market

      Last Listing Agent Maria Taylor Klemm Real Estate Inc

  • 30 Hollow Rd, Woodbury, CT 06798
    30 Hollow Rd, Woodbury, CT 06798
    /2

    $1,395,000

    $100K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 4,884 Sq Ft

    30 Hollow Rd, Woodbury, CT 06798

    Step through the doors of history and into one of Connecticut's most treasured colonial residences. Built in 1760 and proudly listed on the National Register of Historic Places, the Jabez Bacon House is a rare masterpiece of 18th-century American architecture that has endured with remarkable grace for over 260 years. This distinguished home has also been recognized for its exceptional

    Lisa Titcomb William Pitt Sotheby's Int'l

    30 Hollow Rd, Woodbury, CT 06798
  • 32 Plumb Brook Rd, Woodbury, CT 06798

    $640,000

    Sold Nov 20, 2025

    32 Plumb Brook Rd, Woodbury, CT 06798

    • 3 Beds
    • 2.5 Baths
    • 2,252 Sq Ft
    • Built 1979

    Last Sold Summary

    • 3% Below List Price
    • $284/SF
    • 54 Days On Market

    Current Estimated Value $665,933

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

    32 Plumb Brook Rd, Woodbury, CT 06798
    • 92 Tuttle Rd, Woodbury, CT 06798

      Est $834,507

      Not Listed For Sale

      92 Tuttle Rd, Woodbury, CT 06798

      • 4 Beds
      • 3.5 Baths
      • 4,104 Sq Ft
      • Built 2005
      92 Tuttle Rd, Woodbury, CT 06798

      Last Sold Summary

      • 85 Days On Market

      Last Listing Agent Dennis Oliveira JDS Realty Group Inc.

  • 6 Highpoint Ct Unit 6, Woodbury, CT 06798
    6 Highpoint Ct Unit 6, Woodbury, CT 06798
    6 Highpoint Ct Unit 6, Woodbury, CT 06798
    /35

    $299,000

    Under Contract
    • 2 Beds
    • 2 Baths
    • 1,182 Sq Ft

    6 Highpoint Ct Unit 6, Woodbury, CT 06798

    ** Multiple offer situation, offers deadline extended to May 9, 5pm**. Privately situated within the complex, this beautifully updated home offers a rare blend of comfort and nature. It abuts hundreds of acres of protected forest, providing exceptional privacy along with the soothing sounds of songbirds, visits from hummingbirds, and abundant wildlife. Located in highly sought-after Woodbury,

    Patricia Huegi Kiwi Homes

    6 Highpoint Ct Unit 6, Woodbury, CT 06798
  • 0 Main St N Unit 24119173, Woodbury, CT 06798

    $35,000

    Sold Nov 20, 2025

    0 Main St N Unit 24119173, Woodbury, CT 06798

    • Land
    • 3.6 Acres
    • $9,722 per Acre

    Last Sold Summary

    • 46% Below List Price
    • 57 Days On Market

    Last Listing Agent Jeff Boucher Drakeley Real Estate, Inc.

    0 Main St N Unit 24119173, Woodbury, CT 06798
    • 40 Stonefield Rd, Woodbury, CT 06798

      Est $915,688

      Not Listed For Sale

      40 Stonefield Rd, Woodbury, CT 06798

      • 3 Beds
      • 2.5 Baths
      • 3,179 Sq Ft
      • Built 2006
      40 Stonefield Rd, Woodbury, CT 06798

      Last Sold Summary

      • 51 Days On Market

      Last Listing Agent Joyce Drakeley Drakeley Real Estate, Inc.

  • 920 Main St S, Woodbury, CT 06798
    920 Main St S, Woodbury, CT 06798
    920 Main St S, Woodbury, CT 06798
    /40

    $2,995,000

    • 4 Beds
    • 6 Baths
    • 5,316 Sq Ft

    920 Main St S, Woodbury, CT 06798

    Warren's Landing on the Pomperaug is an extraordinary estate where historic character is centered around a beautifully preserved 1890 Greek Revival residence. The home offers four bedrooms, timeless architectural details, spacious rooms, 4 fireplaces and custom built-ins. The impressive six-barn complex provides exceptional flexibility, featuring a retail shop, extensive equipment storage, a

    Maria Taylor Klemm Real Estate Inc

    920 Main St S, Woodbury, CT 06798
  • 18 Grey Fox Trail, Woodbury, CT 06798

    $585,000

    Sold Aug 27, 2025

    18 Grey Fox Trail, Woodbury, CT 06798

    • 3 Beds
    • 2.5 Baths
    • 1,873 Sq Ft
    • Built 1974

    Last Sold Summary

    • 10% Below List Price
    • $312/SF
    • 49 Days On Market

    Current Estimated Value $625,316

    Last Listing Agent Joseph Lorino Klemm Real Estate Inc

    18 Grey Fox Trail, Woodbury, CT 06798
    • 11 Boxwood Ct, Woodbury, CT 06798

      Est $337,296

      Not Listed For Sale

      11 Boxwood Ct, Woodbury, CT 06798

      • 3 Beds
      • 2.5 Baths
      • 2,388 Sq Ft
      • Built 1974
      11 Boxwood Ct, Woodbury, CT 06798

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent Camron Cottam RE/MAX RISE

  • 28 School St, Woodbury, CT 06798
    28 School St, Woodbury, CT 06798
    28 School St, Woodbury, CT 06798
    /20

    $775,000

    • 4 Beds
    • 3.5 Baths
    • 2,708 Sq Ft

    28 School St, Woodbury, CT 06798

    The Orton-Martin Homestead. One of Woodbury's oldest homes has been updated for today's lifestyle. History surrounds you with wide board flooring, library built-ins, two fireplaces and 1850 barn. This four -bedroom home offers spacious rooms, three finished levels and hidden delights. Enjoy picnics under the mature trees on your own fenced-in level yard. Sidewalks take you everywhere on Main St

    Sindy Butkus Klemm Real Estate Inc

    28 School St, Woodbury, CT 06798
  • 97 Westwood Rd, Woodbury, CT 06798

    $250,000

    Sold Aug 29, 2025

    97 Westwood Rd, Woodbury, CT 06798

    • 2 Beds
    • 1 Bath
    • 1,264 Sq Ft
    • Built 1850

    Last Sold Summary

    • 11% Below List Price
    • $198/SF
    • 13 Days On Market

    Current Estimated Value $276,729

    Last Listing Agent Amy Vayan BHGRE Gaetano Marra Homes

    97 Westwood Rd, Woodbury, CT 06798
    • 20 Birchwood Ln, Woodbury, CT 06798

      Est $937,032

      Not Listed For Sale

      20 Birchwood Ln, Woodbury, CT 06798

      • 4 Beds
      • 3.5 Baths
      • 3,693 Sq Ft
      • Built 2004
      20 Birchwood Ln, Woodbury, CT 06798

      Last Sold Summary

      • 168 Days On Market

      Last Listing Agent Tim Mohl HomeSmart Homes and Estates

  • 523 Main St N, Woodbury, CT 06798
    523 Main St N, Woodbury, CT 06798
    523 Main St N, Woodbury, CT 06798
    /15

    $990,000

    New Construction Pending
    • 3 Beds
    • 2 Baths
    • 2,300 Sq Ft

    523 Main St N, Woodbury, CT 06798

    To be built Modern style home with gorgeous southern views and privacy from your neighbors. Enjoy the wall of glass overlooking a bluestone patio, and beautiful views above Main Street North! Just a few minutes from Woodbury's town center, this home provides an open floor with a kitchen/great room, a cathedral ceiling, and a floor-to-ceiling masonry fireplace. The first floor includes a primary

    Tim Drakeley Drakeley Real Estate, Inc.

    523 Main St N, Woodbury, CT 06798
  • 229 Bacon Pond Rd Unit 451, Woodbury, CT 06798

    $189,200

    Sold Jul 13, 2026

    229 Bacon Pond Rd Unit 451, Woodbury, CT 06798

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

    Last Sold Summary

    • 3% Above List Price
    • $207/SF
    • 40 Days On Market

    Current Estimated Value $181,727

    Last Listing Agent Susan Pelletier Berkshire Hathaway NE Prop.

    229 Bacon Pond Rd Unit 451, Woodbury, CT 06798
    • 18 Lake Rd, Woodbury, CT 06798

      Est $436,761

      Not Listed For Sale

      18 Lake Rd, Woodbury, CT 06798

      • 4 Beds
      • 3 Baths
      • 2,028 Sq Ft
      • Built 1956
      18 Lake Rd, Woodbury, CT 06798

      Last Sold Summary

      • 44 Days On Market

      Last Listing Agent David Aurigemma Regency Real Estate, LLC

  • 27 Middle Quarter Rd, Woodbury, CT 06798
    27 Middle Quarter Rd, Woodbury, CT 06798
    27 Middle Quarter Rd, Woodbury, CT 06798
    /26

    $999,900

    $100K PRICE DROP Under Contract
    • 3 Beds
    • 2.5 Baths
    • 2,042 Sq Ft

    27 Middle Quarter Rd, Woodbury, CT 06798

    Discover the charm of this beautiful antique home in the heart of Woodbury! Nestled on the serene Middle Quarter Road, this vintage gem is being restored by the current owner and is just a 2-minute stroll from coffee shops, top-notch restaurants, and the historic Main Street. The home will be meticulously updated from the ground up, featuring wide board antique flooring, a stunning great room

    Tim Drakeley Drakeley Real Estate, Inc.

    27 Middle Quarter Rd, Woodbury, CT 06798
  • 229 Bacon Pond Rd Unit 453, Woodbury, CT 06798

    $145,000

    Sold Jun 04, 2026

    229 Bacon Pond Rd Unit 453, Woodbury, CT 06798

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

    Last Sold Summary

    • $159/SF
    • 33 Days On Market

    Current Estimated Value $145,639

    Last Listing Agent Deborah Snopkowski Coldwell Banker Realty

    229 Bacon Pond Rd Unit 453, Woodbury, CT 06798
    • 229 Bacon Pond Rd Unit 233, Woodbury, CT 06798

      Est $179,640

      Not Listed For Sale

      229 Bacon Pond Rd Unit 233, Woodbury, CT 06798

      • 2 Beds
      • 1 Bath
      • 913 Sq Ft
      • Built 1971
      229 Bacon Pond Rd Unit 233, Woodbury, CT 06798

      Last Sold Summary

      • 142 Days On Market

      Last Listing Agent Joe Dimyan Tower Realty Corp

  • 206 Minortown Rd, Woodbury, CT 06798
    206 Minortown Rd, Woodbury, CT 06798
    206 Minortown Rd, Woodbury, CT 06798
    /39

    $575,000

    Under Contract
    • 3 Beds
    • 3 Baths
    • 1,692 Sq Ft

    206 Minortown Rd, Woodbury, CT 06798

    Cute as a button Cape Cod style home in charming and historic Woodbury! A lovingly cared for home within a short drive of main street, area schools, Walker Road Winery and all other major conveniences. Step right into this light and bright home that provides a newly remodeled kitchen, oak floors throughout, two bedrooms on the main level and charming exposed beams. Comfortable and cozy, sit and

    Katherine Parlato Drakeley Real Estate, Inc.

    206 Minortown Rd, Woodbury, CT 06798
  • 1 Alder Ct Unit 1, Woodbury, CT 06798

    $300,000

    Sold Sep 11, 2025

    1 Alder Ct Unit 1, Woodbury, CT 06798

    • 2 Beds
    • 2.5 Baths
    • 1,365 Sq Ft
    • Built 1974

    Last Sold Summary

    • $220/SF
    • 54 Days On Market

    Current Estimated Value $306,932

    Last Listing Agent Camilo Ramirez Higgins Group Real Estate

    1 Alder Ct Unit 1, Woodbury, CT 06798
    • 38 Woodbury Hill, Woodbury, CT 06798

      Est $493,862

      Not Listed For Sale

      38 Woodbury Hill, Woodbury, CT 06798

      • 2 Beds
      • 2.5 Baths
      • 1,796 Sq Ft
      • Built 1985
      38 Woodbury Hill, Woodbury, CT 06798

      Last Sold Summary

      • 32 Days On Market

      Last Listing Agent Tim Drakeley Drakeley Real Estate, Inc.

  • 0 Flanders Rd, Woodbury, CT 06798
    0 Flanders Rd, Woodbury, CT 06798
    /2

    $1,150,000

    • Land
    • 42.6 Acres
    • $26,995 per Acre

    0 Flanders Rd, Woodbury, CT 06798

    East Meadowbrook Farm presents a rare opportunity to own a legacy New England property offered for the first time since 1918. Encompassing 42 acres, including 15 rolling, sun-drenched acres of open fields, this former dairy and Christmas tree farm is bordered by 250 acres of protected Flanders Nature Center conservation land, creating an extraordinary sense of privacy and permanence. A quarter

    Tim Drakeley Drakeley Real Estate, Inc.

    0 Flanders Rd, Woodbury, CT 06798
  • 5 Upper Commons, Woodbury, CT 06798

    $250,000

    Sold Apr 14, 2026

    5 Upper Commons, Woodbury, CT 06798

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

    Last Sold Summary

    • 6% Below List Price
    • $212/SF
    • 102 Days On Market

    Last Listing Agent Rafael Monegro Coldwell Banker Realty

    5 Upper Commons, Woodbury, CT 06798
    • 236 Quassuk Rd, Woodbury, CT 06798

      Est $454,484

      Not Listed For Sale

      236 Quassuk Rd, Woodbury, CT 06798

      • 3 Beds
      • 2 Baths
      • 1,606 Sq Ft
      • Built 1840
      236 Quassuk Rd, Woodbury, CT 06798

      Last Sold Summary

      • 62 Days On Market

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

  • 38 Grey Fox Trail, Woodbury, CT 06798
    38 Grey Fox Trail, Woodbury, CT 06798
    38 Grey Fox Trail, Woodbury, CT 06798
    /38

    $579,000

    Under Contract
    • 4 Beds
    • 2.5 Baths
    • 2,154 Sq Ft

    38 Grey Fox Trail, Woodbury, CT 06798

    Have you been looking for a Woodbury home with that special balance of privacy and accessibility? This well-maintained four bedroom, three bath Colonial may just be the answer. The heart of the home is a bright, sunlit kitchen and breakfast nook that opens into a spacious family room with a wood-burning brick fireplace and skylights in a vaulted ceiling; sliders lead to a large 32 x 16 foot deck

    Tom Greto William Raveis Real Estate

    38 Grey Fox Trail, Woodbury, CT 06798
  • 360 Old Sherman Hill Rd, Woodbury, CT 06798

    $426,500

    Sold Jun 23, 2026

    360 Old Sherman Hill Rd, Woodbury, CT 06798

    • 3 Beds
    • 1 Bath
    • 1,296 Sq Ft
    • Built 1966

    Last Sold Summary

    • 5% Below List Price
    • $329/SF
    • 41 Days On Market

    Current Estimated Value $415,448

    Last Listing Agent Levi Judqin Brass Moon Realty

    360 Old Sherman Hill Rd, Woodbury, CT 06798
    • 167 Hazel Plain Rd, Woodbury, CT 06798

      Est $665,226

      Not Listed For Sale

      167 Hazel Plain Rd, Woodbury, CT 06798

      • 4 Beds
      • 3.5 Baths
      • 2,922 Sq Ft
      • Built 1977
      167 Hazel Plain Rd, Woodbury, CT 06798

      Last Sold Summary

      • 13 Days On Market

      Last Listing Agent Kerri Dimitratos William Raveis Real Estate

  • 229 Bacon Pond Rd Unit 354, Woodbury, CT 06798
    229 Bacon Pond Rd Unit 354, Woodbury, CT 06798
    229 Bacon Pond Rd Unit 354, Woodbury, CT 06798
    /23

    $185,000

    Under Contract
    • 2 Beds
    • 1 Bath
    • 913 Sq Ft

    229 Bacon Pond Rd Unit 354, Woodbury, CT 06798

    Welcome to this highly sought after and rarely available upper end unit in Woodbury's charming and serene Town in Country condominium complex. This updated unit boasts a renovated kitchen and newer floors throughout the well-designed layout. The open concept kitchen, dining, and living room is perfect for everyday living and entertaining guests. Step through the slider doors onto a large balcony

    Matthew Amatruda Drakeley Real Estate, Inc.

    229 Bacon Pond Rd Unit 354, Woodbury, CT 06798
  • 15 Lynns Corner Rd, Woodbury, CT 06798

    $490,000

    Sold Nov 20, 2025

    15 Lynns Corner Rd, Woodbury, CT 06798

    • 4 Beds
    • 3 Baths
    • 2,216 Sq Ft
    • Built 1948

    Last Sold Summary

    • $221/SF
    • 27 Days On Market

    Current Estimated Value $514,908

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

    15 Lynns Corner Rd, Woodbury, CT 06798
    • 61 Sherman Heights Rd, Woodbury, CT 06798

      Est $415,449

      Not Listed For Sale

      61 Sherman Heights Rd, Woodbury, CT 06798

      • 2 Beds
      • 1 Bath
      • 924 Sq Ft
      • Built 1943
      61 Sherman Heights Rd, Woodbury, CT 06798

      Last Sold Summary

      • 103 Days On Market

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

  • 16 Cross Brook Rd, Woodbury, CT 06798
    16 Cross Brook Rd, Woodbury, CT 06798
    16 Cross Brook Rd, Woodbury, CT 06798
    /39

    $649,900

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,750 Sq Ft

    16 Cross Brook Rd, Woodbury, CT 06798

    Fantastic Potential in this home. Three bedroom Cape Cod sitting on 5.50 acre lot with a giant barn that has great potential living space to convert into an in-laws set up, office, studio space or music studio to fit your lifestyle. Home freshly painted interior and exterior. Renovated kitchen with all new countertops and Italian farmhouse sink, floors, Pantry, refreshed cabinets. All newer

    Beatriz Conroy William Raveis Real Estate

    16 Cross Brook Rd, Woodbury, CT 06798
  • 25 Curtiss Meadows, Woodbury, CT 06798

    $970,000

    Sold Dec 09, 2025

    25 Curtiss Meadows, Woodbury, CT 06798

    • 4 Beds
    • 3.5 Baths
    • 3,113 Sq Ft
    • Built 2005

    Last Sold Summary

    • 1% Below List Price
    • $312/SF
    • 132 Days On Market

    Last Listing Agent Ralph Harvey ListWithFreedom.com

    25 Curtiss Meadows, Woodbury, CT 06798
    • 49 Owl Ridge Rd, Woodbury, CT 06798

      Est $1,725,797

      Not Listed For Sale

      49 Owl Ridge Rd, Woodbury, CT 06798

      • 4 Beds
      • 5 Baths
      • 8,000 Sq Ft
      • Built 2006
      49 Owl Ridge Rd, Woodbury, CT 06798

      Last Sold Summary

      • 135 Days On Market

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

  • 245 Hoop Pole Hill Rd, Woodbury, CT 06798
    245 Hoop Pole Hill Rd, Woodbury, CT 06798
    245 Hoop Pole Hill Rd, Woodbury, CT 06798
    /4

    $1,000,000

    • Land
    • 62 Acres
    • $16,129 per Acre

    245 Hoop Pole Hill Rd, Woodbury, CT 06798

    An exceptional opportunity to own 76.9 acres in one of Woodbury's most desirable locations. This unique offering includes two contiguous parcels to be sold together, consisting of 14.9-acre parcel (MLS# 24192651) and this adjoining 62-acre parcel Featuring a charming 3-bedroom home, the property offers a rare combination of rolling meadows, mature woodlands, and open fields, creating endless

    Chris Ferguson Keller Williams Realty

    245 Hoop Pole Hill Rd, Woodbury, CT 06798

Showing Results 121 - 160, Page 4 of 18

Connecticut Litchfield County

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