Woodbury, CT Homes

• 

  $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 $687,701

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

  43 Mill Rd, Woodbury, CT 06798
• 

  Est $1,116,214

  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
• 

  

  

  /34

  $184,500

  Under Contract

  • 2 Beds
  • 1 Bath
  • 913 Sq Ft

  229 Bacon Pond Rd Unit 451, Woodbury, CT 06798

  Step into condo living in this freshly painted two bedroom unit with new vinyl plank flooring in the foyer, living room and dining room. Curl up in front of your fireplace on cool nights or walk a few steps to the in-ground pool to cool off in the summer. The kitchen features a stainless steel glasstop range and brand new dishwasher. Both generously-sized bedrooms feature fresh paint and brand

  Susan Pelletier Berkshire Hathaway NE Prop.

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

  $483,000

  Sold Aug 06, 2025

  3 Lynns Corner Rd, Woodbury, CT 06798

  • 3 Beds
  • 2 Baths
  • 2,400 Sq Ft
  • Built 1948

  Last Sold Summary

  • 9% Below List Price
  • $201/SF
  • 67 Days On Market

  Current Estimated Value $505,584

  Last Listing Agent Rhya Szymansky Drakeley Real Estate, Inc.

  3 Lynns Corner Rd, Woodbury, CT 06798
• 

  Est $180,968

  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
• 

  

  /40

  $1,900,000

  • 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
• 

  $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 $217,884

  Last Listing Agent Donna Doyle Keller Williams Realty

  229 Bacon Pond Rd Unit 332, Woodbury, CT 06798
• 

  Est $465,880

  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
• 

  

  /34

  $540,000

  Open Sun 12PM - 2PM $9K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 2,292 Sq Ft

  49 Scuppo Rd, Woodbury, CT 06798

  Discover this beautifully updated ranch-style home ideally situated on over an acre of level, private land. Offering 2292 square feet of comfortable one-level living space, this 3-bedroom, 1.5 bath home combines timeless character with modern upgrades-perfect for those seeking space, tranquility, and convenience. Inside you'll find a bright and expansive living room with cathedral ceilings,

  Joseph Conforti West View Properties, LLC

  49 Scuppo 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 $322,307

  Last Listing Agent Danielle Rownin Keller Williams Realty

  2 Linden Rd, Woodbury, CT 06798
• 

  Est $770,896

  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
• 

  

  /40

  $499,989

  • 3 Beds
  • 2.5 Baths
  • 1,580 Sq Ft

  12 Walker Rd, Woodbury, CT 06798

  Would you like to live in beautiful Woodbury Connecticut. Set on 1.95 acres of peaceful, private grounds, this beautifully updated 3-bedroom, 2.1-bath home sits gracefully on a gentle rise at the top of the driveway, partially framed by classic white post and rail fencing that enhances its New England charm. The entire home-interior, exterior, trim, and baseboards-has been freshly painted,

  MaryAnne Betso Coldwell Banker Realty

  12 Walker Rd, Woodbury, CT 06798
• 

  $290,000

  Sold Aug 29, 2025

  9 Lower Commons Unit 9, Woodbury, CT 06798

  • 2 Beds
  • 2.5 Baths
  • 1,456 Sq Ft
  • Built 1979

  Last Sold Summary

  • 12% Below List Price
  • $199/SF
  • 98 Days On Market

  Last Listing Agent Michelle Lorenzetti Premier Re Group LLC

  9 Lower Commons Unit 9, Woodbury, CT 06798
• 

  Est $197,474

  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
• 

  

  /40

  $569,900

  Under Contract

  • 4 Beds
  • 2 Baths
  • 1,875 Sq Ft

  338 Good Hill Rd, Woodbury, CT 06798

  Nestled on 1.53 acres and set back from the road, this charming Cape Cod style home offers the perfect blend of comfort, character and New England charm. The interior features 2 bedrooms and a full bath on the main and upper level. An inviting Living Room showcases a fireplace with an energy efficient woodburning insert, creating a warm and cozy gathering space. The dining area provides access to

  Roberta Allen William Raveis Real Estate

  338 Good Hill Rd, Woodbury, CT 06798
• 

  $290,000

  Sold Jul 22, 2025

  2 Edgehill Ct, Woodbury, CT 06798

  • 2 Beds
  • 2 Baths
  • 1,532 Sq Ft
  • Built 1980

  Last Sold Summary

  • 2% Below List Price
  • $189/SF
  • 47 Days On Market

  Current Estimated Value $288,924

  Last Listing Agent Christina Moulthrop Showcase Realty, Inc.

  2 Edgehill Ct, Woodbury, CT 06798
• 

  Est $587,809

  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
• 

  

  /39

  $865,000

  • 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
• 

  $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 $534,143

  Last Listing Agent Tim Drakeley Drakeley Real Estate, Inc.

  18 Woodbury Hill, Woodbury, CT 06798
• 

  Est $572,004

  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
• 

  

  /37

  $260,000

  $10K PRICE DROP

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

  4 Woods Way, Woodbury, CT 06798

  Nestled in the desirable Woodlake community, this townhouse at 4 Woods Way offers the perfect blend of comfort, convenience, and cozy living. The inviting layout features a bright and spacious living area with hardwood floors, a brick wood burning fireplace, open-concept dining, and easy access to a private deck-perfect for relaxing or entertaining. The kitchen offers generous cabinet storage and

  Jenn Lailer BHGRE Gaetano Marra Homes

  4 Woods Way, 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
• 

  Est $841,463

  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
• 

  

  /40

  $1,069,900

  Under Contract

  • 4 Beds
  • 3.5 Baths
  • 4,776 Sq Ft

  61 Silver Brook Ln, Woodbury, CT 06798

  Exceptional Colonial in one of Woodbury's finest developments, beautifully set among similar distinguished homes at the end of Silver Brook Lane. Thoughtfully updated over the past five years with high-quality materials and careful attention to detail, this 4,000+ square foot residence offers an ideal blend of elegance, comfort, and modern convenience. The heart of the home is the stunning

  Tim Drakeley Drakeley Real Estate, Inc.

  61 Silver Brook Ln, Woodbury, CT 06798
• 

  $545,000

  Sold Jul 07, 2025

  259 Old Town Farm Rd, Woodbury, CT 06798

  • 3 Beds
  • 3 Baths
  • 3,149 Sq Ft
  • Built 1977

  Last Sold Summary

  • 5% Below List Price
  • $173/SF
  • 30 Days On Market

  Current Estimated Value $561,410

  Last Listing Agent Ron Nettleton William Raveis Real Estate

  259 Old Town Farm Rd, Woodbury, CT 06798
• 

  Est $857,230

  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
• 

  

  /34

  $574,900

  $25K PRICE DROP Pending

  • 3 Beds
  • 2 Baths
  • 1,470 Sq Ft

  2 Judd Hill Rd, Woodbury, CT 06798

  Charm and modern comfort come together in this beautifully renovated 3-bedroom, 2-bath home set on nearly an acre along a quiet country road in Woodbury. Thoughtfully updated and move-in ready, this inviting home blends classic New England character with practical improvements throughout, including a fully insulated attic and insulated walls added by the current owner for enhanced comfort and

  Tim Drakeley Drakeley Real Estate, Inc.

  2 Judd Hill Rd, Woodbury, CT 06798
• 

  $196,000

  Sold Sep 05, 2025

  126 Sherman Hill Rd Unit C7, Woodbury, CT 06798

  • 2 Beds
  • 1 Bath
  • 1,150 Sq Ft
  • Built 1964

  Last Sold Summary

  • 2% Below List Price
  • $170/SF
  • 32 Days On Market

  Last Listing Agent Katherine Parlato Drakeley Real Estate, Inc.

  126 Sherman Hill Rd Unit C7, Woodbury, CT 06798
• 

  Est $341,505

  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
• 

  

  /24

  $745,000

  New Construction

  • 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 on 2 homes with anticipated completion in August. #86 is a 3

  Scott Volpe Coldwell Banker Realty

  86 Quail Run 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 $844,731

  Last Listing Agent Tim Drakeley Drakeley Real Estate, Inc.

  99 Plumb Brook Rd, Woodbury, CT 06798
• 

  Est $888,121

  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
• 

  /2

  $1,495,000

  • 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
• 

  $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 $372,846

  Last Listing Agent Holly Mullins Coldwell Banker Realty

  10 Lake Rd, Woodbury, CT 06798
• 

  Est $399,097

  Not Listed For Sale

  354 Quassapaug Rd, Woodbury, CT 06798

  • 3 Beds
  • 1.5 Baths
  • 1,452 Sq Ft
  • Built 1966

  354 Quassapaug Rd, Woodbury, CT 06798

  Last Sold Summary

  • 53 Days On Market
• 

  

  /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
• 

  $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 $516,299

  Last Listing Agent Christina Zainc BHGRE Gaetano Marra Homes

  9 Hill View Ln, Woodbury, CT 06798
• 

  Est $432,901

  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
• 

  

  /40

  $499,000

  $26K PRICE DROP Pending

  • 3 Beds
  • 1.5 Baths
  • 2,102 Sq Ft

  14 Meadow Crest Dr, Woodbury, CT 06798

  Opportunity knocks! Your chance to reside in an exclusive cul-de-sac area of north Woodbury! Homes on this street rarely come on the market. Situated on almost 4.5 acres and within a short drive of Woodbury and Watertown centers, including prestigious, private Taft School, this three bedroom, 1.5 bath colonial awaits its new owners! Exterior features include a chicken coop, above ground pool,

  Katherine Parlato Drakeley Real Estate, Inc.

  14 Meadow Crest Dr, 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 $412,678

  Last Listing Agent Donna J. Matula William Raveis Real Estate

  70 Mountain Rd, Woodbury, CT 06798

Showing Results 81 - 120, Page 3 of 18