4,919

Woodbury, CT Homes

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  • 48 Woods Way, Woodbury, CT 06798
    48 Woods Way, Woodbury, CT 06798
    48 Woods Way, Woodbury, CT 06798
    /26

    $259,900

    $20K PRICE DROP Under Contract
    • 2 Beds
    • 2 Baths
    • 1,182 Sq Ft

    48 Woods Way, Woodbury, CT 06798

    Don't miss this beauty! Lovely Renovated End Unit with year round Rhododendron - greenery privacy at the deck. The summer blooms are spectacular! This condo is close to the Woodlake Community Garden, for those wishing to grow your own veggies! Inside you will notice a light-filled renovated kitchen with granite countertops, tiled flooring, ceiling fan and stainless steel appliances. The living

    Terry Lee Adams Adams & Adams Real Estate

    48 Woods Way, Woodbury, CT 06798
  • 43 Mill Rd, Woodbury, CT 06798

    $705,000

    Sold Apr 07, 2026

    43 Mill Rd, Woodbury, CT 06798

    • 3 Beds
    • 2.5 Baths
    • 2,073 Sq Ft
    • Built 2009

    Last Sold Summary

    • 4% Above List Price
    • $340/SF
    • 27 Days On Market

    Current Estimated Value $694,775

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

    43 Mill Rd, Woodbury, CT 06798
    • 54 Barbara Ln, Woodbury, CT 06798

      Est $492,690

      Not Listed For Sale

      54 Barbara Ln, Woodbury, CT 06798

      • 3 Beds
      • 2.5 Baths
      • 2,901 Sq Ft
      • Built 1959
      54 Barbara Ln, Woodbury, CT 06798

      Last Sold Summary

      • 36 Days On Market

      Last Listing Agent Tim Drakeley Drakeley Real Estate, Inc.

  • 63 Main St N, Woodbury, CT 06798
    63 Main St N, Woodbury, CT 06798
    63 Main St N, Woodbury, CT 06798
    /4

    $849,900

    Coming Soon
    • 4 Beds
    • 2 Baths
    • 2,662 Sq Ft

    63 Main St N, Woodbury, CT 06798

    Reader's Digest named Woodbury the "Most Charming Small Town in Connecticut" in 2024 and received the same recognition in 2020 and 2018.That fits this home perfectly. 63 Main St N is an 1850 antique home with a 2002 addition, offering 4 bedrooms, 2 updated bathrooms and 2,662 square feet of delight on 0.36 acres. It has the historic character people expect from Main Street - mahogany-floored

    Sindy Butkus Klemm Real Estate Inc

    63 Main St N, Woodbury, CT 06798
  • 106 Sprain Brook Rd, Woodbury, CT 06798

    $535,000

    Sold Aug 27, 2026

    106 Sprain Brook Rd, Woodbury, CT 06798

    • 3 Beds
    • 2 Baths
    • 2,002 Sq Ft
    • Built 1993

    Last Sold Summary

    • 3% Below List Price
    • $267/SF
    • 13 Days On Market

    Current Estimated Value $552,122

    Last Listing Agent Kimberly Peterson BHGRE Gaetano Marra Homes

    106 Sprain Brook Rd, Woodbury, CT 06798
    • 229 Bacon Pond Rd Unit 352, Woodbury, CT 06798

      Est $202,164

      Not Listed For Sale

      229 Bacon Pond Rd Unit 352, Woodbury, CT 06798

      • 2 Beds
      • 1 Bath
      • 913 Sq Ft
      • Built 1971
      229 Bacon Pond Rd Unit 352, Woodbury, CT 06798

      Last Sold Summary

      • 22 Days On Market

      Last Listing Agent Nickie O'Toole Nickie Otoole Realty LLC

  • 0 Hoop Pole Hill, Woodbury, CT 06798
    0 Hoop Pole Hill, Woodbury, CT 06798
    0 Hoop Pole Hill, Woodbury, CT 06798
    /4

    $250,000

    • Land
    • 14.9 Acres
    • $16,779 per Acre

    0 Hoop Pole Hill, 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 this 14.9-acre parcel and the adjoining 62-acre parcel (MLS #24192209). *The 14.9 is land-locked and can not be sold separate). Featuring a charming 3-bedroom home, the property offers a rare combination of rolling

    Chris Ferguson Keller Williams Realty

    0 Hoop Pole Hill, Woodbury, CT 06798
  • 20 Stagecoach Rd, Woodbury, CT 06798

    $635,000

    Sold Aug 03, 2026

    20 Stagecoach Rd, Woodbury, CT 06798

    • 4 Beds
    • 2.5 Baths
    • 2,157 Sq Ft
    • Built 1976

    Last Sold Summary

    • 1% Above List Price
    • $294/SF
    • 38 Days On Market

    Current Estimated Value $622,126

    Last Listing Agent Robert Leonard William Raveis Real Estate

    20 Stagecoach Rd, Woodbury, CT 06798
    • 51 Joshua Hill Rd, Woodbury, CT 06798

      Est $371,523

      Not Listed For Sale

      51 Joshua Hill Rd, Woodbury, CT 06798

      • 3 Beds
      • 1.5 Baths
      • 1,508 Sq Ft
      • Built 1960
      51 Joshua Hill Rd, Woodbury, CT 06798

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Sarah Perrotti Regency Real Estate, LLC

  • 126 Main St N, Woodbury, CT 06798
    126 Main St N, Woodbury, CT 06798
    126 Main St N, Woodbury, CT 06798
    /37

    $699,000

    • 4 Beds
    • 1.5 Baths
    • 1,872 Sq Ft

    126 Main St N, Woodbury, CT 06798

    Classic 1930s Colonial set along Main Street in Woodbury, offering the timeless character and craftsmanship of the era. Thoughtfully set back from the road on an expansive lawn, the home features hardwood floors throughout, high ceilings, detailed moldings, interior French doors, charming built-ins, a generous foyer, and a graceful central staircase. The front-to-back living room is anchored by a

    Tim Drakeley Drakeley Real Estate, Inc.

    126 Main St N, Woodbury, CT 06798
  • 229 Bacon Pond Rd Unit 332, Woodbury, CT 06798

    $220,000

    Sold Nov 03, 2025

    229 Bacon Pond Rd Unit 332, Woodbury, CT 06798

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

    Last Sold Summary

    • 16% Above List Price
    • $241/SF
    • 33 Days On Market

    Current Estimated Value $219,759

    Last Listing Agent Donna Doyle Keller Williams Realty

    229 Bacon Pond Rd Unit 332, Woodbury, CT 06798
    • 28 Fox Run, Woodbury, CT 06798

      Est $277,146

      Not Listed For Sale

      28 Fox Run, Woodbury, CT 06798

      • 2 Beds
      • 2 Baths
      • 1,182 Sq Ft
      • Built 1980
      28 Fox Run, Woodbury, CT 06798

      Last Sold Summary

      • 55 Days On Market

      Last Listing Agent Wendy Brazauskas Coldwell Banker Realty

  • 50 Washington Rd, Woodbury, CT 06798
    50 Washington Rd, Woodbury, CT 06798
    50 Washington Rd, Woodbury, CT 06798
    /40

    $519,000

    Open Sun 12PM - 2PM
    • 3 Beds
    • 1.5 Baths
    • 1,550 Sq Ft

    50 Washington Rd, Woodbury, CT 06798

    CHARM, CHARACTER & CLASSIC NEW ENGLAND APPEAL IN HISTORIC WOODBURY! Welcome to this distinctive 1895 Colonial farmhouse, where timeless architectural character blends beautifully with thoughtful modern updates. Offering 3 bedrooms and 1.5 baths, this inviting home is filled with warmth, natural light, and the craftsmanship that makes an older New England home so special. Step inside to discover

    Elliott Morales eXp Realty

    50 Washington Rd, Woodbury, CT 06798
  • 2 Linden Rd, Woodbury, CT 06798

    $315,000

    Sold Apr 07, 2026

    2 Linden Rd, Woodbury, CT 06798

    • 5 Beds
    • 2 Baths
    • 2,760 Sq Ft
    • Built 1938

    Last Sold Summary

    • 21% Below List Price
    • $114/SF
    • 209 Days On Market

    Current Estimated Value $323,386

    Last Listing Agent Danielle Rownin Keller Williams Realty

    2 Linden Rd, Woodbury, CT 06798
    • 18 River View Ln, Woodbury, CT 06798

      Est $896,062

      Not Listed For Sale

      18 River View Ln, Woodbury, CT 06798

      • 4 Beds
      • 3.5 Baths
      • 3,447 Sq Ft
      • Built 1995
      18 River View Ln, Woodbury, CT 06798

      Last Sold Summary

      • 59 Days On Market

      Last Listing Agent Wendy Brazauskas Coldwell Banker Realty

  • 40 Ruffin Rd, Woodbury, CT 06798
    40 Ruffin Rd, Woodbury, CT 06798
    40 Ruffin Rd, Woodbury, CT 06798
    /40

    $1,590,000

    $310K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,732 Sq Ft

    40 Ruffin Rd, Woodbury, CT 06798

    It's rare to find a vintage estate tucked away from a main road, but this one sits at the end of a private lane, opening to 6.3 enchanting acres framed by stone walls, manicured gardens, and a charming vintage home. The property includes a large custom two-story pole barn, inground pool, detached three-bay garage, and an adorable potting shed. The great room flows into a kitchen with handmade

    Mary Ann Bennett Drakeley Real Estate, Inc.

    40 Ruffin Rd, Woodbury, CT 06798
  • 674 Middle Road Turnpike, Woodbury, CT 06798

    $699,000

    Sold Jul 28, 2026

    674 Middle Road Turnpike, Woodbury, CT 06798

    • 3 Beds
    • 2.5 Baths
    • 2,360 Sq Ft
    • Built 1987

    Last Sold Summary

    • 4% Above List Price
    • $296/SF
    • 39 Days On Market

    Current Estimated Value $703,078

    Last Listing Agent Chris Carbone HomeSmart Homes and Estates

    674 Middle Road Turnpike, Woodbury, CT 06798
    • 41 Curtiss Meadows, Woodbury, CT 06798

      Est $973,855

      Not Listed For Sale

      41 Curtiss Meadows, Woodbury, CT 06798

      • 4 Beds
      • 3.5 Baths
      • 3,468 Sq Ft
      • Built 2007
      41 Curtiss Meadows, Woodbury, CT 06798

      Last Sold Summary

      • 38 Days On Market

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

  • 4 Alder Ct Unit 4, Woodbury, CT 06798
    4 Alder Ct Unit 4, Woodbury, CT 06798
    4 Alder Ct Unit 4, Woodbury, CT 06798
    /37

    $349,500

    Pending
    • 3 Beds
    • 2.5 Baths
    • 2,464 Sq Ft

    4 Alder Ct Unit 4, Woodbury, CT 06798

    Welcome to Woodlake! Move right in and enjoy the space, comfort, and lifestyle this beautifully maintained 3-bedroom, 2.5-bath townhouse has to offer. The light-filled and flexible floor plan includes spacious main-level living, 2 generous upstairs bedrooms, and a huge finished walkout lower level with an additional room perfect for a home office, gym, or hobby space. Updates and improvements are

    Ann Gerschefski William Raveis Real Estate

    4 Alder Ct Unit 4, Woodbury, CT 06798
  • 6 Easy St, Woodbury, CT 06798

    $250,000

    Sold Aug 27, 2026

    6 Easy St, Woodbury, CT 06798

    • 3 Beds
    • 1.5 Baths
    • 1,562 Sq Ft
    • Built 1847

    Last Sold Summary

    • 9% Below List Price
    • $160/SF
    • 60 Days On Market

    Current Estimated Value $261,046

    Last Listing Agent Jessica Caruso Berkshire Hathaway NE Prop.

    6 Easy St, Woodbury, CT 06798
    • 23 Woodbury Hill, Woodbury, CT 06798

      Est $467,881

      Not Listed For Sale

      23 Woodbury Hill, Woodbury, CT 06798

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

      Last Sold Summary

      • 55 Days On Market

      Last Listing Agent Donna Bannon BHGRE Gaetano Marra Homes

  • 138 Minortown Rd, Woodbury, CT 06798
    138 Minortown Rd, Woodbury, CT 06798
    138 Minortown Rd, Woodbury, CT 06798
    /40

    $1,600,000

    • 4 Beds
    • 2.5 Baths
    • 3,122 Sq Ft

    138 Minortown Rd, Woodbury, CT 06798

    Turnkey Equestrian Facility on 21 Acres. A rare opportunity to own a fully operational equestrian property offering the perfect blend of functionality, comfort, and income potential. Set on 21 acres, this established working horse boarding facility features 21 stalls, a heated indoor riding arena with viewing area, heated tack rooms, two wash stalls, private storage lockers, two outdoor riding

    Heather Crabtree RE/MAX RISE

    138 Minortown Rd, Woodbury, CT 06798
  • 18 Woodbury Hill, Woodbury, CT 06798

    $540,000

    Sold Jan 08, 2026

    18 Woodbury Hill, Woodbury, CT 06798

    • 2 Beds
    • 2 Baths
    • 1,796 Sq Ft
    • Built 1985

    Last Sold Summary

    • 10% Below List Price
    • $301/SF
    • 70 Days On Market

    Current Estimated Value $546,669

    Last Listing Agent Tim Drakeley Drakeley Real Estate, Inc.

    18 Woodbury Hill, Woodbury, CT 06798
    • 105 Old Grassy Hill Rd, Woodbury, CT 06798

      Est $1,189,564

      Not Listed For Sale

      105 Old Grassy Hill Rd, Woodbury, CT 06798

      • 4 Beds
      • 5 Baths
      • 6,978 Sq Ft
      • Built 1999
      105 Old Grassy Hill Rd, Woodbury, CT 06798

      Last Sold Summary

      • 142 Days On Market

      Last Listing Agent Brian Hunter Hunter Realty Group

  • Unlisted Address
    Unlisted Address
    Unlisted Address
    /17

    $550,000

    • 3 Beds
    • 2 Baths
    • 1,550 Sq Ft

    Unlisted Address

    Charming Brick Ranch on 2+ Acres Nestled on more than two acres in a peaceful setting, this well-built brick ranch offers the perfect blend of privacy, comfort, and convenience, with easy access to shopping, dining, and everyday amenities. The home has been freshly painted, meticulously maintained, and reflects pride of ownership throughout. Inside, you'll find a spacious and inviting floor plan

    Mark Nolan Nolan Realty LLC

    Unlisted Address
  • 17 Curtiss Rd, Woodbury, CT 06798

    $825,000

    Sold Aug 31, 2026

    17 Curtiss Rd, Woodbury, CT 06798

    • 3 Beds
    • 2.5 Baths
    • 2,103 Sq Ft
    • Built 1900

    Last Sold Summary

    • 1% Above List Price
    • $392/SF
    • 40 Days On Market

    Current Estimated Value $815,649

    Last Listing Agent Art Rose William Raveis Real Estate

    17 Curtiss Rd, Woodbury, CT 06798
    • 229 Bacon Pond Rd Unit 412, Woodbury, CT 06798

      Est $195,545

      Not Listed For Sale

      229 Bacon Pond Rd Unit 412, Woodbury, CT 06798

      • 2 Beds
      • 1 Bath
      • 913 Sq Ft
      • Built 1971
      229 Bacon Pond Rd Unit 412, Woodbury, CT 06798

      Last Sold Summary

      • 66 Days On Market

      Last Listing Agent Barbara Podlisny William Raveis Real Estate

  • 31 Bethwood Ln, Woodbury, CT 06798
    31 Bethwood Ln, Woodbury, CT 06798
    31 Bethwood Ln, Woodbury, CT 06798
    /27

    $765,000

    • 2 Beds
    • 2 Baths
    • 1,814 Sq Ft

    31 Bethwood Ln, Woodbury, CT 06798

    Newly re-imagined and completely renovated single level jewel box on quiet country lane with tree-lined driveway and long seasonal views. The open-concept living areas are designed for effortless entertaining with soaring vaulted ceilings, exposed beams, a floor-to-ceiling brick double-sided fireplace and a fabulous dedicated bar room. A new series of skylights creates a bright and airy space

    Melinda Dubow Klemm Real Estate Inc

    31 Bethwood Ln, Woodbury, CT 06798
  • 1 Upper Commons Unit 1, Woodbury, CT 06798

    $245,000

    Sold May 01, 2026

    1 Upper Commons Unit 1, Woodbury, CT 06798

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

    Last Sold Summary

    • 6% Below List Price
    • $207/SF
    • 7 Days On Market

    Last Listing Agent Odaine Jones GLR ESTATES LLC

    1 Upper Commons Unit 1, Woodbury, CT 06798
    • 163 Washington Rd, Woodbury, CT 06798

      Est $484,514

      Not Listed For Sale

      163 Washington Rd, Woodbury, CT 06798

      • 4 Beds
      • 3 Baths
      • 2,521 Sq Ft
      • Built 1836
      163 Washington Rd, Woodbury, CT 06798

      Last Sold Summary

      • 162 Days On Market

      Last Listing Agent Katherine Parlato Drakeley Real Estate, Inc.

  • 47 Woods Way Unit 47, Woodbury, CT 06798
    47 Woods Way Unit 47, Woodbury, CT 06798
    47 Woods Way Unit 47, Woodbury, CT 06798
    /32

    $299,900

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

    47 Woods Way Unit 47, Woodbury, CT 06798

    Welcome to 47 Woods Way! This beautifully renovated Woodlake townhouse is truly move-in ready, offering stylish updates and the convenience of a garage just steps from your front door. Step inside to discover a gorgeous new kitchen featuring crisp white Shaker cabinetry, gleaming quartz countertops, and stainless steel appliances. New RevWood by Mohawk flooring flows throughout the first floor,

    Stephanie Chapman BHGRE Gaetano Marra Homes

    47 Woods Way Unit 47, Woodbury, CT 06798
  • 99 Plumb Brook Rd, Woodbury, CT 06798

    $850,000

    Sold Jun 03, 2026

    99 Plumb Brook Rd, Woodbury, CT 06798

    • 4 Beds
    • 2.5 Baths
    • 3,330 Sq Ft
    • Built 2004

    Last Sold Summary

    • $255/SF
    • 77 Days On Market

    Current Estimated Value $845,906

    Last Listing Agent Tim Drakeley Drakeley Real Estate, Inc.

    99 Plumb Brook Rd, Woodbury, CT 06798
    • 434 Quassapaug Rd, Woodbury, CT 06798

      Est $801,167

      Not Listed For Sale

      434 Quassapaug Rd, Woodbury, CT 06798

      • 4 Beds
      • 2.5 Baths
      • 3,334 Sq Ft
      • Built 2006
      434 Quassapaug Rd, Woodbury, CT 06798

      Last Sold Summary

      • 118 Days On Market

      Last Listing Agent Mary Ann Hebert BHGRE Gaetano Marra Homes

  • 3 Shagbark Ln Unit 3, Woodbury, CT 06798
    3 Shagbark Ln Unit 3, Woodbury, CT 06798
    3 Shagbark Ln Unit 3, Woodbury, CT 06798
    /40

    $294,900

    • 2 Beds
    • 2.5 Baths
    • 1,601 Sq Ft

    3 Shagbark Ln Unit 3, 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. This end unit is within a short walking distance of the lake, clubhouse and other complex amenities! Spacious and bright, this Congeniality II model offers an open floor plan, and two spacious bedrooms with 2.5

    Katherine Parlato Drakeley Real Estate, Inc.

    3 Shagbark Ln Unit 3, Woodbury, CT 06798
  • 5 Westwood Rd, Woodbury, CT 06798

    $570,000

    Sold Jul 15, 2026

    5 Westwood Rd, Woodbury, CT 06798

    • 3 Beds
    • 2 Baths
    • 1,961 Sq Ft
    • Built 1907

    Last Sold Summary

    • 1% Below List Price
    • $291/SF
    • 9 Days On Market

    Current Estimated Value $562,805

    Last Listing Agent Brad Harriman RJ Real Estate

    5 Westwood Rd, Woodbury, CT 06798
    • 229 Bacon Pond Rd Unit 342, Woodbury, CT 06798

      Est $206,670

      Not Listed For Sale

      229 Bacon Pond Rd Unit 342, Woodbury, CT 06798

      • 2 Beds
      • 1 Bath
      • 913 Sq Ft
      • Built 1971
      229 Bacon Pond Rd Unit 342, Woodbury, CT 06798

      Last Sold Summary

      • 16 Days On Market

      Last Listing Agent Lemon DeLucia Coldwell Banker Realty

  • 201 Transylvania Rd, Woodbury, CT 06798
    201 Transylvania Rd, Woodbury, CT 06798
    201 Transylvania Rd, Woodbury, CT 06798
    /25

    $699,900

    • 3 Beds
    • 2.5 Baths
    • 2,451 Sq Ft

    201 Transylvania Rd, Woodbury, CT 06798

    Imagine starting your morning with a cup of coffee on the gorgeous wraparound front porch as you take in the view of Radey Pond or spending warm summer evenings entertaining family and friends in this beautiful and private setting.Situated on 2.31 acres, this charming 3/4-bedroom, 2.5-bath Cape/Colonial offers the perfect combination of classic New England character, comfortable living space, and

    Kary Apanovitch Coldwell Banker Realty

    201 Transylvania Rd, Woodbury, CT 06798
  • 10 Lake Rd, Woodbury, CT 06798

    $366,500

    Sold Dec 19, 2025

    10 Lake Rd, Woodbury, CT 06798

    • 2 Beds
    • 2 Baths
    • 1,504 Sq Ft
    • Built 1956

    Last Sold Summary

    • 5% Above List Price
    • $244/SF
    • 46 Days On Market

    Current Estimated Value $395,250

    Last Listing Agent Holly Mullins Coldwell Banker Realty

    10 Lake Rd, Woodbury, CT 06798
    • 233 Old Sherman Hill Rd, Woodbury, CT 06798

      Est $607,786

      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

  • 1917 Main St N, Woodbury, CT 06798
    1917 Main St N, Woodbury, CT 06798
    1917 Main St N, Woodbury, CT 06798
    /39

    $850,000

    $15K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 4,819 Sq Ft

    1917 Main St N, Woodbury, CT 06798

    Built in 1854, this 5.91 acre property offers an incredible value impossible to replicate today for the price. The property includes an Italianate stone home with an approx 675 sq foot retail/office room with a separate entrance at the driveway, a 28' x 53' post and beam barn with a full walkout lower level, a large pond, stone walls, incredible perennial garden surround, and a 21' x 45'

    Amy Lapierre Coldwell Banker Realty

    1917 Main St N, Woodbury, CT 06798

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