Woodbury, CT Homes

• 

  $350,000

  Sold Dec 18, 2025

  0 Main St N Unit 24072824, Woodbury, CT 06798

  • Land
  • 56.29 Acres
  • $6,218 per Acre

  Last Sold Summary

  • 12% Below List Price
  • 316 Days On Market

  Last Listing Agent Tim Drakeley Drakeley Real Estate, Inc.

  0 Main St N Unit 24072824, Woodbury, CT 06798
• 

  

  

  /25

  Est $257,514

  Not Listed For Sale

  74 Washington Rd Unit 16, Woodbury, CT 06798

  • 2 Beds
  • 1.5 Baths
  • 960 Sq Ft
  • Built 1969

  74 Washington Rd Unit 16, Woodbury, CT 06798

  Last Sold Summary

  Last Listing Agent Joel Matson Coldwell Banker Realty
• 

  

  

  /40

  $525,000

  $40K PRICE DROP Pending

  • 5 Beds
  • 3 Baths
  • 4,130 Sq Ft

  33 Hurds Hill Rd, Woodbury, CT 06798

  Nestled in the well-established Sherman Hill neighborhood, this five-bedroom home offers a generous footprint to put your personal touches on. Boasting wood flooring and newer windows throughout, the main level features a fluid layout designed for effortless living: a spacious living room, formal dining room, an eat-in kitchen, a cozy family room with a fireplace, a private home office, and a

  Christian Jensen William Pitt Sotheby's Int'l

  33 Hurds Hill Rd, Woodbury, CT 06798
• 

  $200,000

  Sold Jan 22, 2026

  12 Edgehill Ct, Woodbury, CT 06798

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

  Last Sold Summary

  • 7% Below List Price
  • $169/SF
  • 38 Days On Market

  Current Estimated Value $220,483

  Last Listing Agent Jacki Hornish W. Raveis Lifestyles Realty

  12 Edgehill Ct, Woodbury, CT 06798
• 

  Est $171,924

  Not Listed For Sale

  229 Bacon Pond Rd Unit 254, Woodbury, CT 06798

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

  229 Bacon Pond Rd Unit 254, Woodbury, CT 06798

  Last Sold Summary

  • 6 Days On Market

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

  

  /21

  $258,000

  Under Contract

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

  10 Summit Ct, Woodbury, CT 06798

  Welcome home to this sun-filled end unit nestled in the highly desirable Woodlake condo community. Offering a perfect blend of comfort, style, and privacy, this beautiful property features nearly 1,200 square feet of thoughtfully designed living space. Step inside to find an inviting, spacious layout seamlessly connecting the main living areas, featuring 2 generously sized bedrooms and 2 full

  Adam Zak Century 21 Classic Homes

  10 Summit Ct, Woodbury, CT 06798
• 

  $110,000

  Sold Nov 19, 2025

  0 Main St N Unit 24072843, Woodbury, CT 06798

  • Land
  • 2.1 Acres
  • $52,381 per Acre

  Last Sold Summary

  • 8% Below List Price
  • 231 Days On Market

  Last Listing Agent Tim Drakeley Drakeley Real Estate, Inc.

  0 Main St N Unit 24072843, Woodbury, CT 06798
• 

  Not Listed For Sale

  203 Sprain Brook Rd, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 2,077 Sq Ft
  • Built 1862

  203 Sprain Brook Rd, Woodbury, CT 06798

  Last Sold Summary

  • 15 Days On Market

  Last Listing Agent Maria Taylor Klemm Real Estate Inc
• 

  

  /30

  $525,000

  Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,241 Sq Ft

  212 Upper Grassy Hill Rd, Woodbury, CT 06798

  Well maintained and updated Raised Ranch 3 bedroom 1.5 bathrooms home ready to move in! Open concept living room/dining room and kitchen that opens on to a gorgeous 12'x30' deck overlooking a beautiful fenced in backyard in the woods make for a very private setting. This home has all new windows, a newly updated kitchen with stainless steel appliances and granite countertops, finished lower-level

  Elena McGlynn William Raveis Real Estate

  212 Upper Grassy Hill Rd, Woodbury, CT 06798
• 

  $540,000

  Sold Jul 27, 2026

  12 Walker Rd, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 1,580 Sq Ft
  • Built 1951

  Last Sold Summary

  • 8% Above List Price
  • $342/SF
  • 38 Days On Market

  Current Estimated Value $491,403

  Last Listing Agent MaryAnne Betso Coldwell Banker Realty

  12 Walker Rd, Woodbury, CT 06798
• 

  Est $473,270

  Not Listed For Sale

  24 Joshua Hill Rd, Woodbury, CT 06798

  • 3 Beds
  • 3 Baths
  • 2,072 Sq Ft
  • Built 1997

  24 Joshua Hill Rd, Woodbury, CT 06798

  Last Sold Summary

  • 128 Days On Market

  Last Listing Agent Karen Dibble-flaherty Keller Williams Realty
• 

  

  /40

  $750,000

  • 3 Beds
  • 1.5 Baths
  • 1,658 Sq Ft

  153 Old Sherman Hill Rd, Woodbury, CT 06798

  Exceptional value and opportunity on 3.5 gorgeous acres! Bring this home back to its original charm. Features hardwood floors throughout and a cozy front porch. The upper level includes 3 bedrooms, a full bath, and access to a walk-up attic from the primary bedroom. The main level offers a half bath and a functional, open layout. Additional property highlights include a separate 962 sq. ft.,

  Heather Weber Coldwell Banker Realty

  153 Old Sherman Hill Rd, Woodbury, CT 06798
• 

  $568,000

  Sold Sep 08, 2025

  81 Park Rd, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 2,144 Sq Ft
  • Built 1965

  Last Sold Summary

  • 1% Below List Price
  • $265/SF
  • 94 Days On Market

  Current Estimated Value $590,937

  Last Listing Agent Matt Rose Keller Williams Realty

  81 Park Rd, Woodbury, CT 06798
• 

  Est $407,601

  Not Listed For Sale

  9 Orenaug Ave, Woodbury, CT 06798

  • 3 Beds
  • 1.5 Baths
  • 2,058 Sq Ft
  • Built 1912

  9 Orenaug Ave, Woodbury, CT 06798

  Last Sold Summary

  • 233 Days On Market

  Last Listing Agent Gary Smith eXp Realty
• 

  

  /33

  $849,000

  • 3 Beds
  • 2 Baths
  • 2,448 Sq Ft

  92 Minortown Rd, Woodbury, CT 06798

  Live Stress-Free in This Income-Producing Equestrian Retreat! Enjoy the best of country living while generating income from your property. Rental revenue from a separate 1 BR apartment and 4 of the 10 horse stalls offers a rare opportunity to offset ownership costs! Situated on 5.76 level acres of open pasture and riding space, this equestrian property is ideal for horse enthusiasts, trainers, or

  Jill Sloane Brown Harris Stevens

  92 Minortown Rd, Woodbury, CT 06798
• 

  $580,000

  Sold Jul 31, 2026

  338 Good Hill Rd, Woodbury, CT 06798

  • 4 Beds
  • 2 Baths
  • 1,875 Sq Ft
  • Built 1990

  Last Sold Summary

  • 2% Above List Price
  • $309/SF
  • 33 Days On Market

  Current Estimated Value $577,575

  Last Listing Agent Roberta Allen William Raveis Real Estate

  338 Good Hill Rd, Woodbury, CT 06798
• 

  Est $168,718

  Not Listed For Sale

  229 Bacon Pond Rd Unit 144, Woodbury, CT 06798

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

  229 Bacon Pond Rd Unit 144, Woodbury, CT 06798

  Last Sold Summary

  • 18 Days On Market

  Last Listing Agent Reza Abbassi New Door Realty
• 

  

  /11

  $895,000

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,400 Sq Ft

  96 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! 2 homes IN CONTRACT, 1 home available for FALL DELIVERY and this new build to start

  Scott Volpe Coldwell Banker Realty

  96 Quail Run Rd, Woodbury, CT 06798
• 

  $600,000

  Sold Nov 20, 2025

  36 Heritage Dr, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 2,032 Sq Ft
  • Built 1968

  Last Sold Summary

  • 5% Below List Price
  • $295/SF
  • 60 Days On Market

  Current Estimated Value $617,537

  Last Listing Agent Justin Bette Century 21 Bette Real Estate

  36 Heritage Dr, Woodbury, CT 06798
• 

  Est $185,245

  Not Listed For Sale

  229 Bacon Pond Rd Unit 443, Woodbury, CT 06798

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

  229 Bacon Pond Rd Unit 443, Woodbury, CT 06798

  Last Sold Summary

  • 8 Days On Market

  Last Listing Agent Ann Gerschefski William Raveis Real Estate
• 

  

  /27

  $645,000

  New Construction Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,081 Sq Ft

  94 Quail Run Rd, Woodbury, CT 06798

  QUAIL RUN On the cul de sac - 4 NEW HOMES 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. #94 is a 3 BR,

  Scott Volpe Coldwell Banker Realty

  94 Quail Run Rd, Woodbury, CT 06798
• 

  $1,225,000

  Sold Nov 16, 2025

  68 Whittlesey Rd, Woodbury, CT 06798

  • 4 Beds
  • 4 Baths
  • 4,682 Sq Ft
  • Built 2006

  Last Sold Summary

  • 4% Above List Price
  • $262/SF
  • 44 Days On Market

  Current Estimated Value $1,262,254

  Last Listing Agent Michael Caporizzo William Pitt Sotheby's Int'l

  68 Whittlesey Rd, Woodbury, CT 06798
• 

  Est $672,726

  Not Listed For Sale

  97 Hard Hill Rd, Woodbury, CT 06798

  • 4 Beds
  • 2 Baths
  • 3,022 Sq Ft
  • Built 1981

  97 Hard Hill Rd, Woodbury, CT 06798

  Last Sold Summary

  • 91 Days On Market

  Last Listing Agent Erik Sousa William Raveis Real Estate
• 

  

  /20

  $650,000

  Under Contract

  • 3 Beds
  • 3.5 Baths
  • 2,479 Sq Ft

  30 Park Rd, Woodbury, CT 06798

  Charming in-town Gambrel Colonial with views of Orenaug Pond, located just up the road from the South Green. Surrounded by historic landmarks such as King Solomon's Lodge, the Hurd House, the Glebe House, and other notable properties, this home offers three bedrooms, three full baths, and one half bath. It also features a remodeled kitchen with stainless appliances that opens to a family room

  Sindy Butkus Klemm Real Estate Inc

  30 Park Rd, Woodbury, CT 06798
• 

  $1,069,900

  Sold Jul 31, 2026

  61 Silver Brook Ln, Woodbury, CT 06798

  • 4 Beds
  • 3.5 Baths
  • 4,776 Sq Ft
  • Built 2003

  Last Sold Summary

  • $224/SF
  • 28 Days On Market

  Current Estimated Value $1,059,730

  Last Listing Agent Tim Drakeley Drakeley Real Estate, Inc.

  61 Silver Brook Ln, Woodbury, CT 06798
• 

  Est $422,526

  Not Listed For Sale

  40 Pilgrim Trail, Woodbury, CT 06798

  • 4 Beds
  • 2.5 Baths
  • 2,544 Sq Ft
  • Built 1966

  40 Pilgrim Trail, Woodbury, CT 06798

  Last Sold Summary

  • 85 Days On Market

  Last Listing Agent Patricia Forbes Berkshire Hathaway NE Prop.
• 

  

  /33

  $250,000

  • 2 Beds
  • 1 Bath
  • 1,128 Sq Ft

  481 Main St N, Woodbury, CT 06798

  Don't miss this incredible opportunity to own a home in beautiful Woodbury, CT! Set on a level lot, this 2-bedroom, 1-bath home features hardwood floors, a spacious country kitchen, and the timeless charm of a classic country home. Ready for your personal updates and improvements, this property offers the perfect chance to add your own style while building instant equity. Whether you're a

  Heather Crabtree RE/MAX RISE

  481 Main St N, Woodbury, CT 06798
• 

  $300,000

  Sold Dec 30, 2025

  9 Heather Ct Unit 9, Woodbury, CT 06798

  • 2 Beds
  • 2.5 Baths
  • 1,723 Sq Ft
  • Built 1979

  Last Sold Summary

  • 2% Above List Price
  • $174/SF
  • 33 Days On Market

  Current Estimated Value $310,016

  Last Listing Agent Ann Micacci Berkshire Hathaway NE Prop.

  9 Heather Ct Unit 9, Woodbury, CT 06798
• 

  Est $487,392

  Not Listed For Sale

  99 Flanders Rd, Woodbury, CT 06798

  • 3 Beds
  • 3 Baths
  • 2,664 Sq Ft
  • Built 1956

  99 Flanders Rd, Woodbury, CT 06798

  Last Sold Summary

  • 337 Days On Market

  Last Listing Agent Joyce Drakeley Drakeley Real Estate, Inc.
• 

  /2

  $400,000

  • Land
  • 22,215 Sq Ft
  • $784,314 per Acre

  1545 Main St N, Woodbury, CT 06798

  Rare Main Street commercial property available in Woodbury, CT. The land and the building upon it are being sold in "as is, where is" condition. Neither the probate court system, the attorney, or the broker have any knowledge as to any deficiencies on the property or if they even exist Located in the OS 60 zone, interested parties should consult with the planning and zoning to verify their

  Mario Longobucco Coldwell Banker Commercial NRT

  1545 Main St N, Woodbury, CT 06798
• 

  $1,275,000

  Sold Jul 31, 2026

  46 Grassy Hill Rd, Woodbury, CT 06798

  • 4 Beds
  • 3.5 Baths
  • 3,480 Sq Ft
  • Built 1984

  Last Sold Summary

  • 15% Below List Price
  • $366/SF
  • 13 Days On Market

  Current Estimated Value $927,204

  Last Listing Agent Tim Drakeley Drakeley Real Estate, Inc.

  46 Grassy Hill Rd, Woodbury, CT 06798
• 

  Est $285,888

  Not Listed For Sale

  49 Clubhouse Dr, Woodbury, CT 06798

  • 2 Beds
  • 2.5 Baths
  • 1,316 Sq Ft
  • Built 1972

  49 Clubhouse Dr, Woodbury, CT 06798

  Last Sold Summary

  • 24 Days On Market

  Last Listing Agent Terry Lee Adams Adams & Adams Real Estate
• 

  

  /20

  $310,000

  Pending

  • 2 Beds
  • 2.5 Baths
  • 1,432 Sq Ft

  11 Lower Commons Unit 11, Woodbury, CT 06798

  Nestled in a serene setting backing up to peaceful woods, this beautifully updated tri-level townhouse offers the perfect blend of comfort, style, and privacy. Freshly painted throughout, this spacious home features 2 bedrooms, 2.5 bathrooms, and a finished basement, providing plenty of room for living, working, and entertaining. The open-concept layout is filled with natural light and includes a

  Lynn LaForme Regency Real Estate, LLC

  11 Lower Commons Unit 11, Woodbury, CT 06798
• 

  $130,000

  Sold Oct 01, 2025

  Lot 64 Highpoint Rd, Woodbury, CT 06798

  • Land
  • 35,283 Sq Ft
  • $160,494 per Acre

  Last Sold Summary

  • 8% Above List Price
  • 88 Days On Market

  Last Listing Agent Justin Bette Century 21 Bette Real Estate

  Lot 64 Highpoint Rd, Woodbury, CT 06798
• 

  Est $467,788

  Not Listed For Sale

  50 Washington Rd, Woodbury, CT 06798

  • 3 Beds
  • 1.5 Baths
  • 1,550 Sq Ft
  • Built 1895

  50 Washington Rd, Woodbury, CT 06798

  Last Sold Summary

  • 62 Days On Market

  Last Listing Agent Rhya Szymansky Drakeley Real Estate, Inc.
• 

  

  /40

  $525,000

  Under Contract

  • 3 Beds
  • 2 Baths
  • 1,914 Sq Ft

  520 Washington Rd, Woodbury, CT 06798

  Classic 1800s vintage Colonial in Connecticut's most charming town! Located within a short drive of all major conveniences, area private/public schools and parks, this three bedroom, two bath home has something for everyone! Situated on a beautifully level lot, enjoy your 1.55 acres by throwing the ball around, entertaining on your slate side patio or terrace area. The backyard barn, named the

  Katherine Parlato Drakeley Real Estate, Inc.

  520 Washington Rd, Woodbury, CT 06798
• 

  $775,000

  Sold Nov 13, 2025

  6 Strong Field Rd, Woodbury, CT 06798

  • 4 Beds
  • 2.5 Baths
  • 2,600 Sq Ft
  • Built 2024

  Last Sold Summary

  • 8% Below List Price
  • $298/SF
  • 103 Days On Market

  Current Estimated Value $789,009

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

  6 Strong Field Rd, Woodbury, CT 06798
• 

  Est $179,746

  Not Listed For Sale

  229 Bacon Pond Rd Unit 241, Woodbury, CT 06798

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

  229 Bacon Pond Rd Unit 241, Woodbury, CT 06798

  Last Sold Summary

  • 34 Days On Market

  Last Listing Agent Taner Genc Coldwell Banker Realty
• 

  

  /33

  $389,900

  Pending

  • 3 Beds
  • 2 Baths
  • 1,578 Sq Ft

  134 Old Sherman Hill Rd, Woodbury, CT 06798

  Welcome home to this charming 3-bedroom, 2-bath ranch, perfectly situated on a lovely lot. This home offers comfortable one-level living with a bright and inviting floor plan designed for everyday living and entertaining. The spacious living areas flow seamlessly into the kitchen and dining space, while three generously sized bedrooms provide ample room for family, guests, or a home office. Enjoy

  Tracey Fiasconaro Berkshire Hathaway NE Prop.

  134 Old Sherman Hill Rd, Woodbury, CT 06798
• 

  $592,750

  Sold Feb 05, 2026

  94 Old Town Farm Rd, Woodbury, CT 06798

  • 6 Beds
  • 3 Baths
  • 4,245 Sq Ft
  • Built 1900

  Last Sold Summary

  • 21% Below List Price
  • $140/SF
  • 175 Days On Market

  Current Estimated Value $636,335

  Last Listing Agent Michael Caporizzo William Pitt Sotheby's Int'l

  94 Old Town Farm Rd, Woodbury, CT 06798

Showing Results 161 - 200, Page 5 of 18