4,919

Woodbury, CT Homes

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  • 819 Main St N, Woodbury, CT 06798
    819 Main St N, Woodbury, CT 06798
    819 Main St N, Woodbury, CT 06798
    /36

    $1,450,000

    $475K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,992 Sq Ft

    819 Main St N, Woodbury, CT 06798

    Open Meadow Farm, a beautifully maintained property offering a blend of rural charm and modern conveniences. Set on 9.88 picturesque acres, this property features three fenced fields, ideal for horses or other livestock and a two-story barn equipped with four stalls, a tack room, gravel storage area and a gleaming concrete main floor. Recent updates include a paved driveway with turnaround, back

    Sindy Butkus Klemm Real Estate Inc

    819 Main St N, Woodbury, CT 06798
  • 298 Railtree Hill Rd, Woodbury, CT 06798
    298 Railtree Hill Rd, Woodbury, CT 06798
    298 Railtree Hill Rd, Woodbury, CT 06798
    /16

    $2,750 Per Month

    • 2 Beds
    • 1 Bath
    • 1,060 Sq Ft
    • House for Rent

    298 Railtree Hill Rd, Woodbury, CT 06798

    Freshly remodeled two-bedroom, one-bathroom rental in Woodbury offering comfortable, updated living space with convenient amenities. The home features a newly updated kitchen and bathroom, along with main-level laundry for added convenience. Enjoy outdoor living with both a side deck and a private rear deck, perfect for grilling, entertaining, or relaxing. Private parking is also included. The

    Kayla O'Grady William Raveis Real Estate

    298 Railtree Hill Rd, Woodbury, CT 06798
  • 48 Coach Light Dr, Woodbury, CT 06798

    $1,400,000

    Sold Jul 16, 2026

    48 Coach Light Dr, Woodbury, CT 06798

    • 4 Beds
    • 4.5 Baths
    • 5,216 Sq Ft
    • Built 2001

    Last Sold Summary

    • 26% Below List Price
    • $268/SF
    • 40 Days On Market

    Current Estimated Value $1,461,364

    Last Listing Agent Nan Jane Keough William Pitt Sotheby's Int'l

    48 Coach Light Dr, Woodbury, CT 06798
    • 60 Stone Pit Rd, Woodbury, CT 06798

      Est $910,139

      Not Listed For Sale

      60 Stone Pit Rd, Woodbury, CT 06798

      • 4 Beds
      • 5 Baths
      • 3,583 Sq Ft
      • Built 1999
      60 Stone Pit Rd, Woodbury, CT 06798

      Last Sold Summary

      • 35 Days On Market

      Last Listing Agent Sharon McGuire William Pitt Sotheby's Int'l

  • 0 Carmel Hill Rd, Woodbury, CT 06798
    0 Carmel Hill Rd, Woodbury, CT 06798
    /2

    $179,900

    Under Contract
    • Land
    • 4 Acres
    • $44,975 per Acre

    0 Carmel Hill Rd, Woodbury, CT 06798

    Discover your own private sanctuary on this enchanting ~4-acre parcel of pristine land perched along scenic Carmel Hill Road in historic Woodbury, CT. Nestled in the heart of Litchfield County's rolling countryside, this remarkable property captivates with mesmerizing views of a sparkling waterfall and the gentle flow of a serene river-nature's own symphony right at your doorstep. Imagine

    Melissa Gordon Coldwell Banker Realty

    0 Carmel Hill Rd, Woodbury, CT 06798
  • 31 McVeigh Rd, Woodbury, CT 06798

    $530,000

    Sold May 01, 2026

    31 McVeigh Rd, Woodbury, CT 06798

    • 4 Beds
    • 2.5 Baths
    • 2,256 Sq Ft
    • Built 1987

    Last Sold Summary

    • 12% Below List Price
    • $235/SF
    • 211 Days On Market

    Current Estimated Value $543,032

    Last Listing Agent Jennifer Bundock Coldwell Banker Realty

    31 McVeigh Rd, Woodbury, CT 06798
    • 29 Lighthouse Rd, Woodbury, CT 06798

      Est $725,739

      Not Listed For Sale

      29 Lighthouse Rd, Woodbury, CT 06798

      • 3 Beds
      • 2 Baths
      • 2,202 Sq Ft
      • Built 1960
      29 Lighthouse Rd, Woodbury, CT 06798

      Last Sold Summary

      • 5 Days On Market

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

  • 39 Hard Hill Rd, Woodbury, CT 06798
    39 Hard Hill Rd, Woodbury, CT 06798
    39 Hard Hill Rd, Woodbury, CT 06798
    /26

    $695,000

    Pending
    • 3 Beds
    • 3 Baths
    • 2,970 Sq Ft

    39 Hard Hill Rd, Woodbury, CT 06798

    Turn-key elevated ranch with in-ground pool, and immaculate grounds. Set on 1.6+ park-like acres, this modern ranch includes 3 bed/3 full baths, a 3-season screened porch, and a heated 20x40 pool with an oversized concrete patio. The living areas and recently renovated eat-in chef's kitchen shine with custom island, top-of-the-line appliances, and a dedicated butler's pantry with sink, wine

    Kathryn Bassett William Pitt Sotheby's Int'l

    39 Hard Hill Rd, Woodbury, CT 06798
  • 90 Railtree Hill Rd, Woodbury, CT 06798

    $595,000

    Sold Nov 03, 2025

    90 Railtree Hill Rd, Woodbury, CT 06798

    • 3 Beds
    • 2 Baths
    • 2,772 Sq Ft
    • Built 1983

    Last Sold Summary

    • 6% Above List Price
    • $215/SF
    • 28 Days On Market

    Current Estimated Value $605,169

    Last Listing Agent Matthew Amatruda Drakeley Real Estate, Inc.

    90 Railtree Hill Rd, Woodbury, CT 06798
    • 220 Church Hill Rd, Woodbury, CT 06798

      Est $1,123,635

      Not Listed For Sale

      220 Church Hill Rd, Woodbury, CT 06798

      • 3 Beds
      • 3.5 Baths
      • 4,632 Sq Ft
      • Built 1997
      220 Church Hill Rd, Woodbury, CT 06798

      Last Sold Summary

      • 51 Days On Market

      Last Listing Agent MaryBeth White William Raveis Real Estate

  • 17 Woodbury Hill Unit 17, Woodbury, CT 06798
    17 Woodbury Hill Unit 17, Woodbury, CT 06798
    17 Woodbury Hill Unit 17, Woodbury, CT 06798
    /27

    $529,900

    $15K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,673 Sq Ft

    17 Woodbury Hill Unit 17, Woodbury, CT 06798

    The finest condo complex in one of Litchfield Counties most charming towns! Woodbury Hill is a lovely community of townhouse style homes in a very attractive setting and features a saltwater pool and tennis/pickleball courts. #17 has seen many upgrades over the past dozen years including new windows, renovated kitchen and baths, upgraded heat pump HVAC and water heater, as well as recent paint

    Justin Bette Century 21 Bette Real Estate

    17 Woodbury Hill Unit 17, Woodbury, CT 06798
  • 5 Kimberly Ln, Woodbury, CT 06798

    $470,000

    Sold Jun 26, 2026

    5 Kimberly Ln, Woodbury, CT 06798

    • 3 Beds
    • 3 Baths
    • 1,732 Sq Ft
    • Built 1979

    Last Sold Summary

    • $271/SF
    • 63 Days On Market

    Current Estimated Value $473,547

    Last Listing Agent Heather Crabtree RE/MAX RISE

    5 Kimberly Ln, Woodbury, CT 06798
    • 325 Cowles Rd, Woodbury, CT 06798

      Est $556,721

      Not Listed For Sale

      325 Cowles Rd, Woodbury, CT 06798

      • 3 Beds
      • 2 Baths
      • 2,190 Sq Ft
      • Built 1947
      325 Cowles Rd, Woodbury, CT 06798

      Last Sold Summary

      • 142 Days On Market

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

  • 19 Clubhouse Dr, Woodbury, CT 06798
    19 Clubhouse Dr, Woodbury, CT 06798
    19 Clubhouse Dr, Woodbury, CT 06798
    /39

    $286,000

    $13K PRICE DROP Under Contract
    • 3 Beds
    • 2.5 Baths
    • 1,708 Sq Ft

    19 Clubhouse Dr, Woodbury, CT 06798

    At Woodlake, you're not just buying a home, you're buying a lifestyle. From being FHA Approved condos, to water views at every balcony, trail walks to boat rides to fountains and everything in between, Woodlake truly offers the peaceful, serene setting that we all dream of. This 3 bedroom, 2.5 bath freshly painted end unit has endless possibilities. Need a main level bedroom or office? One can be

    Macey Mazzella RE/MAX RISE

    19 Clubhouse Dr, Woodbury, CT 06798
  • 3 Tamarack Ln Unit 3, Woodbury, CT 06798

    $276,375

    Sold Aug 12, 2026

    3 Tamarack Ln Unit 3, Woodbury, CT 06798

    • 2 Beds
    • 3 Baths
    • 1,059 Sq Ft
    • Built 1974

    Last Sold Summary

    • 13% Below List Price
    • $261/SF
    • 133 Days On Market

    Last Listing Agent Stephen Mele Houlihan Lawrence

    3 Tamarack Ln Unit 3, Woodbury, CT 06798
    • 76 Washington Rd Unit 40, Woodbury, CT 06798

      Est $254,609

      Not Listed For Sale

      76 Washington Rd Unit 40, Woodbury, CT 06798

      • 2 Beds
      • 1.5 Baths
      • 1,430 Sq Ft
      • Built 1988
      76 Washington Rd Unit 40, Woodbury, CT 06798

      Last Sold Summary

      • 22 Days On Market

      Last Listing Agent Colleen Pickwick eXp Realty

  • 137 & 141 Main St S, Woodbury, CT 06798
    137 & 141 Main St S, Woodbury, CT 06798
    137 & 141 Main St S, Woodbury, CT 06798
    /21

    $600,000

    Pending
    • 9 Beds
    • 8 Baths
    • 4,492 Sq Ft

    137 & 141 Main St S, Woodbury, CT 06798

    Rare mixed-use investment opportunity on over an acre along Woodbury's desirable Main Street South. This unique property features a seven-unit residential building, a detached garage with an additional apartment above, and a separate commercial building offering approximately 2,000 square feet with its own dedicated entrance and access. Three of the residential units are currently occupied, while

    Taylor O'Keefe Drakeley Real Estate, Inc.

    137 & 141 Main St S, Woodbury, CT 06798
  • 43 Bethwood Ln, Woodbury, CT 06798

    $513,999

    Sold Jun 25, 2026

    43 Bethwood Ln, Woodbury, CT 06798

    • 3 Beds
    • 2 Baths
    • 1,750 Sq Ft
    • Built 1948

    Last Sold Summary

    • 3% Above List Price
    • $294/SF
    • 49 Days On Market

    Current Estimated Value $510,690

    Last Listing Agent Tim Drakeley Drakeley Real Estate, Inc.

    43 Bethwood Ln, Woodbury, CT 06798
    • 5 Blueberry Ln, Woodbury, CT 06798

      Est $1,108,808

      Not Listed For Sale

      5 Blueberry Ln, Woodbury, CT 06798

      • 3 Beds
      • 2.5 Baths
      • 3,874 Sq Ft
      • Built 2006
      5 Blueberry Ln, Woodbury, CT 06798

      Last Sold Summary

      • 36 Days On Market

      Last Listing Agent John Donato Jr Showcase Realty, Inc.

  • 132 Good Hill Rd, Woodbury, CT 06798
    132 Good Hill Rd, Woodbury, CT 06798
    132 Good Hill Rd, Woodbury, CT 06798
    /33

    $875,000

    • 5 Beds
    • 3.5 Baths
    • 4,180 Sq Ft

    132 Good Hill Rd, Woodbury, CT 06798

    Original owner, large Colonial Home with 4 room, private entry inlaw suite on the main level. Close to town center and schools. 4180 s/f plus the 750 s/f inlaw! Bring on the big multi-generational family! Natural sun filtered house has front and back staircases, large rooms, 9'ceilings, and mostly hardwood. Granite kitchen/ great room open to breakfast nook, family room w fireplace and french

    Mary Ann Bennett Drakeley Real Estate, Inc.

    132 Good Hill Rd, Woodbury, CT 06798
  • 4 Heather Ct Unit 4, Woodbury, CT 06798

    $310,000

    Sold Apr 13, 2026

    4 Heather Ct Unit 4, Woodbury, CT 06798

    • 3 Beds
    • 2.5 Baths
    • 1,888 Sq Ft
    • Built 1974

    Last Sold Summary

    • $164/SF
    • 82 Days On Market

    Last Listing Agent Jenn Lailer BHGRE Gaetano Marra Homes

    4 Heather Ct Unit 4, Woodbury, CT 06798
    • 101 Railtree Hill Rd, Woodbury, CT 06798

      Est $781,024

      Not Listed For Sale

      101 Railtree Hill Rd, Woodbury, CT 06798

      • 4 Beds
      • 2.5 Baths
      • 3,341 Sq Ft
      • Built 1987
      101 Railtree Hill Rd, Woodbury, CT 06798

      Last Sold Summary

      • 19 Days On Market

      Last Listing Agent Ellen Vincent William Raveis Real Estate

  • 2 Shagbark Ln Unit 2, Woodbury, CT 06798
    2 Shagbark Ln Unit 2, Woodbury, CT 06798
    2 Shagbark Ln Unit 2, Woodbury, CT 06798
    /40

    $294,500

    Under Contract
    • 2 Beds
    • 2.5 Baths
    • 1,249 Sq Ft

    2 Shagbark Ln Unit 2, Woodbury, CT 06798

    Welcome home to Woodlake! The Woodlake community provides non-motorized boating on the lake, hiking trails, basketball, tennis courts, and a playground area for the kids to name a few. The indoor pool, located in the Clubhouse, is also under renovations for future use. This end unit is within a short walking distance of the lake, clubhouse and other complex amenities! Spacious and bright, this

    Katherine Parlato Drakeley Real Estate, Inc.

    2 Shagbark Ln Unit 2, Woodbury, CT 06798
  • 667 Upper Grassy Hill Rd, Woodbury, CT 06798

    $522,500

    Sold Feb 18, 2026

    667 Upper Grassy Hill Rd, Woodbury, CT 06798

    • 4 Beds
    • 2 Baths
    • 1,987 Sq Ft
    • Built 1973

    Last Sold Summary

    • 5% Below List Price
    • $263/SF
    • 75 Days On Market

    Current Estimated Value $544,344

    Last Listing Agent Rhya Szymansky Drakeley Real Estate, Inc.

    667 Upper Grassy Hill Rd, Woodbury, CT 06798
    • 62 Whittlesey Rd, Woodbury, CT 06798

      Est $922,450

      Not Listed For Sale

      62 Whittlesey Rd, Woodbury, CT 06798

      • 4 Beds
      • 2.5 Baths
      • 3,205 Sq Ft
      • Built 2002
      62 Whittlesey Rd, Woodbury, CT 06798

      Last Sold Summary

      • 34 Days On Market

      Last Listing Agent Brianna Carvalho Compass Connecticut, LLC

  • 241 Hoop Pole Hill Rd, Woodbury, CT 06798
    241 Hoop Pole Hill Rd, Woodbury, CT 06798
    241 Hoop Pole Hill Rd, Woodbury, CT 06798
    /21

    $399,000

    $76K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,032 Sq Ft

    241 Hoop Pole Hill Rd, Woodbury, CT 06798

    INVESTORS TAKE NOTICE!! A rare opportunity to bring your vision to life in beautiful Woodbury. 3BR, 2.5 bath Cape just over 2,000 square feet of comfortable living space with endless potential. This home includes hardwood floors throughout. A dedicated home office with custom built-in shelving. Large living room with pellet stove and a spacious mudroom with vaulted ceilings, laundry hookups, and

    Rhya Szymansky Drakeley Real Estate, Inc.

    241 Hoop Pole Hill Rd, Woodbury, CT 06798
  • 242 Bacon Pond Rd, Woodbury, CT 06798

    $513,000

    Sold Jun 22, 2026

    242 Bacon Pond Rd, Woodbury, CT 06798

    • 4 Beds
    • 2 Baths
    • 1,836 Sq Ft
    • Built 1782

    Last Sold Summary

    • 8% Above List Price
    • $279/SF
    • 81 Days On Market

    Current Estimated Value $508,483

    Last Listing Agent Tim Drakeley Drakeley Real Estate, Inc.

    242 Bacon Pond Rd, Woodbury, CT 06798
    • 267 Good Hill Rd, Woodbury, CT 06798

      Not Listed For Sale

      267 Good Hill Rd, Woodbury, CT 06798

      • 3 Beds
      • 4 Baths
      • 3,349 Sq Ft
      • Built 1790
      267 Good Hill Rd, Woodbury, CT 06798

      Last Sold Summary

      • 54 Days On Market

      Last Listing Agent Maris LeBlanc William Pitt Sotheby's Int'l

  • 112 W Lake Rd Unit 112, Woodbury, CT 06798
    112 W Lake Rd Unit 112, Woodbury, CT 06798
    112 W Lake Rd Unit 112, Woodbury, CT 06798
    /37

    $1,795,000

    • 2 Beds
    • 2 Baths
    • 1,197 Sq Ft

    112 W Lake Rd Unit 112, Woodbury, CT 06798

    Just 2 hours from New York City, this exceptional lakefront retreat offers a rare blend of privacy, natural beauty & turnkey luxury. Tucked at the end of West Lake Rd and bordered by the protected woodlands of Flanders Nature Center Preserve, the property enjoys sweeping, unobstructed views across pristine Lake Quassapaug to historic Tranquillity Farm, designed by McKim, Mead & White. Lake

    Karla Murtaugh Compass Connecticut, LLC

    112 W Lake Rd Unit 112, Woodbury, CT 06798
  • 2 South Meadows Unit 2, Woodbury, CT 06798

    $347,000

    Sold Aug 21, 2026

    2 South Meadows Unit 2, Woodbury, CT 06798

    • 3 Beds
    • 2.5 Baths
    • 2,069 Sq Ft
    • Built 1980

    Last Sold Summary

    • 8% Below List Price
    • $168/SF
    • 130 Days On Market

    Last Listing Agent Terry Lee Adams Adams & Adams Real Estate

    2 South Meadows Unit 2, Woodbury, CT 06798
    • 229 Bacon Pond Rd Unit 132, Woodbury, CT 06798

      Est $187,693

      Not Listed For Sale

      229 Bacon Pond Rd Unit 132, Woodbury, CT 06798

      • 2 Beds
      • 1 Bath
      • 913 Sq Ft
      • Built 1971
      229 Bacon Pond Rd Unit 132, Woodbury, CT 06798

      Last Sold Summary

      • 56 Days On Market

      Last Listing Agent Tom Greto William Raveis Real Estate

  • 35 Woodbury Hill, Woodbury, CT 06798
    35 Woodbury Hill, Woodbury, CT 06798
    35 Woodbury Hill, Woodbury, CT 06798
    /39

    $510,000

    $15K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,796 Sq Ft

    35 Woodbury Hill, Woodbury, CT 06798

    Welcome to beautiful Woodbury, CT! Beautiful 2 BR, 2 1/2 bath condo in sought after Woodbury Hill Condos. Park like grounds with only 78 condos, featuring a saltwater pool and a tennis/pickleball court. Well maintained condo features the main level with a Living room with vaulted ceiling and a wood-burning fireplace, dining room w/bow window, a half bath with granite vanity, an updated kitchen

    Donna Doyle Keller Williams Realty

    35 Woodbury Hill, Woodbury, CT 06798
  • 84 Hurds Hill Rd, Woodbury, CT 06798

    $850,000

    Sold Oct 29, 2025

    84 Hurds Hill Rd, Woodbury, CT 06798

    • 4 Beds
    • 2.5 Baths
    • 3,736 Sq Ft
    • Built 1966

    Last Sold Summary

    • 4% Below List Price
    • $228/SF
    • 135 Days On Market

    Current Estimated Value $900,638

    Last Listing Agent Michael Vartolone William Raveis Real Estate

    84 Hurds Hill Rd, Woodbury, CT 06798
    • 3 Inwood Ln, Woodbury, CT 06798

      Est $818,861

      Not Listed For Sale

      3 Inwood Ln, Woodbury, CT 06798

      • 4 Beds
      • 4 Baths
      • 3,330 Sq Ft
      • Built 1986
      3 Inwood Ln, Woodbury, CT 06798

      Last Sold Summary

      • 58 Days On Market

      Last Listing Agent Elizabeth Newnham William Pitt Sotheby's Int'l

  • 0 Cowles Rd, Woodbury, CT 06798
    0 Cowles Rd, Woodbury, CT 06798
    0 Cowles Rd, Woodbury, CT 06798
    /13

    $675,000

    Under Contract
    • Land
    • 23 Acres
    • $29,348 per Acre

    0 Cowles Rd, Woodbury, CT 06798

    Presenting a rare opportunity to acquire a 23-acre parcel that has been held within a family for generations. This expansive property, fronting on a tranquil county road, offers a serene and private setting for your future endeavors. The property is a picturesque combination of woodlands, offering an idyllic setting for those seeking privacy and connection to nature. With approximately 800 feet

    John Sniffen William Pitt Sotheby's Int'l

    0 Cowles Rd, Woodbury, CT 06798
  • 437 Middle Road Turnpike, Woodbury, CT 06798

    $517,000

    Sold Aug 11, 2026

    437 Middle Road Turnpike, Woodbury, CT 06798

    • 3 Beds
    • 1.5 Baths
    • 1,144 Sq Ft
    • Built 1964

    Last Sold Summary

    • 13% Below List Price
    • $452/SF
    • 94 Days On Market

    Current Estimated Value $526,545

    Last Listing Agent Erin Loucks BHGRE Gaetano Marra Homes

    437 Middle Road Turnpike, Woodbury, CT 06798
    • 229 Bacon Pond Rd Unit 142, Woodbury, CT 06798

      Est $185,296

      Not Listed For Sale

      229 Bacon Pond Rd Unit 142, Woodbury, CT 06798

      • 2 Beds
      • 1 Bath
      • 913 Sq Ft
      • Built 1971
      229 Bacon Pond Rd Unit 142, Woodbury, CT 06798

      Last Sold Summary

      • 60 Days On Market

      Last Listing Agent Anthony Rivera Pro Property Management, LLC

  • 253 Bacon Pond Rd, Woodbury, CT 06798
    253 Bacon Pond Rd, Woodbury, CT 06798
    253 Bacon Pond Rd, Woodbury, CT 06798
    /35

    $895,000

    • 4 Beds
    • 2.5 Baths
    • 2,283 Sq Ft

    253 Bacon Pond Rd, Woodbury, CT 06798

    Welcome to Bacon Pond House. A seamless blend of 19th-century soul and 21st-century luxury. Situated on over 3 acres, this antique Colonial has been thoughtfully revived to honor its heritage while offering every modern convenience. The interior, lovingly brought back to life, features wide-plank flooring and exposed hand-hewn beams that anchor the home's historic character. The rooms are

    Christian Jensen William Pitt Sotheby's Int'l

    253 Bacon Pond Rd, Woodbury, CT 06798
  • 74 Middle Quarter Rd, Woodbury, CT 06798

    $665,000

    Sold May 26, 2026

    74 Middle Quarter Rd, Woodbury, CT 06798

    • 4 Beds
    • 2.5 Baths
    • 2,874 Sq Ft
    • Built 1835

    Last Sold Summary

    • 3% Below List Price
    • $231/SF
    • 47 Days On Market

    Current Estimated Value $672,200

    Last Listing Agent Jennifer Kelley Compass Connecticut, LLC

    74 Middle Quarter Rd, Woodbury, CT 06798
    • 87 Minortown Rd, Woodbury, CT 06798

      Est $411,473

      Not Listed For Sale

      87 Minortown Rd, Woodbury, CT 06798

      • 3 Beds
      • 1.5 Baths
      • 1,615 Sq Ft
      • Built 1965
      87 Minortown Rd, Woodbury, CT 06798

      Last Sold Summary

      • 91 Days On Market

      Last Listing Agent Rhonda Stokes Drakeley Real Estate, Inc.

Showing Results 41 - 80, Page 2 of 18

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