Woodbury, CT Homes

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  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
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  /38

  $555,000

  Under Contract

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

  33 Hurds Hill Rd, Woodbury, CT 06798

  BACK ON THE MARKET with a NEW SEPTIC being installed, NEW WELL, and MORE. This generous 5-bedroom home offers a generous footprint to put your personal touches on. Boasting wood flooring and newer windows throughout, the main level features a spacious living room, formal dining room, an eat-in kitchen, a cozy family room with fireplace, a private home office, and a full bathroom. Upstairs, you'll

  Christian Jensen William Pitt Sotheby's Int'l

  33 Hurds 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 $507,363

  Last Listing Agent MaryAnne Betso Coldwell Banker Realty

  12 Walker Rd, Woodbury, CT 06798
• 

  Est $492,686

  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
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  /29

  $649,900

  Open Sun 12PM - 2PM

  • 3 Beds
  • 1.5 Baths
  • 1,814 Sq Ft

  10 Weekeepeemee Rd, Woodbury, CT 06798

  The John Cramer House at 10 Weekeepeemee Road is listed on the National Register of Historic Places and is a wonderful example of Greek Revival architecture. Rich in period character, the home features beautiful chestnut plank flooring, nearly 9-foot ceilings, and an original fireplace with a beehive oven. The first floor offers a study, living room, dining room, granite-countered kitchen, and a

  Joyce Drakeley Drakeley Real Estate, Inc.

  10 Weekeepeemee 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 $573,782

  Last Listing Agent Roberta Allen William Raveis Real Estate

  338 Good Hill Rd, Woodbury, CT 06798
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  Est $422,230

  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
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  /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
• 

  $230,000

  Sold Aug 17, 2026

  4 Woods Way, Woodbury, CT 06798

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

  Last Sold Summary

  • 15% Below List Price
  • $195/SF
  • 47 Days On Market

  Last Listing Agent Jenn Lailer BHGRE Gaetano Marra Homes

  4 Woods Way, Woodbury, CT 06798
• 

  Est $178,608

  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
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  /30

  $199,900

  Under Contract

  • 2 Beds
  • 1.5 Baths
  • 1,150 Sq Ft

  126 Sherman Hill Rd Unit C15, Woodbury, CT 06798

  Nestled in the scenic hills of Woodbury, Connecticut, this open and airy upper level 2-bedroom condo offers the perfect blend of comfort, charm, and convenience. Soaring ceilings create a spacious feel throughout, while a cozy fireplace serves as the focal point of the inviting living area. The well-appointed kitchen provides ample space for cooking and entertaining, complemented by a dedicated

  Karen Consalvo Coldwell Banker Realty

  126 Sherman Hill Rd Unit C15, 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 $615,809

  Last Listing Agent Justin Bette Century 21 Bette Real Estate

  36 Heritage Dr, Woodbury, CT 06798
• 

  Est $194,597

  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
• 

  

  /40

  $599,900

  $150K PRICE DROP

  • 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
• 

  $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 $1,254,699

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

  68 Whittlesey Rd, Woodbury, CT 06798
• 

  Est $616,568

  Not Listed For Sale

  18 Grey Fox Trail, Woodbury, CT 06798

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

  18 Grey Fox Trail, Woodbury, CT 06798

  Last Sold Summary

  • 49 Days On Market

  Last Listing Agent Joseph Lorino Klemm Real Estate Inc
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  /33

  $819,000

  $30K PRICE DROP

  • 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
• 

  $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 $1,058,951

  Last Listing Agent Tim Drakeley Drakeley Real Estate, Inc.

  61 Silver Brook Ln, Woodbury, CT 06798
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  Est $687,509

  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
• 

  

  /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
• 

  $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 $304,940

  Last Listing Agent Ann Micacci Berkshire Hathaway NE Prop.

  9 Heather Ct Unit 9, Woodbury, CT 06798
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  Est $441,221

  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.
• 

  

  /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
• 

  $1,275,000

  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 $1,463,475

  Last Listing Agent Tim Drakeley Drakeley Real Estate, Inc.

  46 Grassy Hill Rd, Woodbury, CT 06798
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  Est $488,509

  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.
• 

  

  /33

  $250,000

  Under Contract

  • 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
• 

  $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 $158,751

  Not Listed For Sale

  229 Bacon Pond Rd Unit 432, Woodbury, CT 06798

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

  229 Bacon Pond Rd Unit 432, Woodbury, CT 06798

  Last Sold Summary

  • 20 Days On Market

  Last Listing Agent Richard Johnson White Hat Realty, LLC
• 

  /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
• 

  $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 $796,934

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

  6 Strong Field Rd, Woodbury, CT 06798
• 

  Est $185,786

  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
• 

  

  /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
• 

  $222,000

  Sold Aug 31, 2026

  16 Fox Run, Woodbury, CT 06798

  • 2 Beds
  • 2 Baths
  • 1,813 Sq Ft
  • Built 1980

  Last Sold Summary

  • 3% Below List Price
  • $122/SF
  • 46 Days On Market

  Current Estimated Value $237,867

  Last Listing Agent Lisa Briscoe William Raveis Real Estate

  16 Fox Run, Woodbury, CT 06798
• 

  Est $528,285

  Not Listed For Sale

  67 Flanders Rd, Woodbury, CT 06798

  • 4 Beds
  • 4 Baths
  • 2,764 Sq Ft
  • Built 1972

  67 Flanders Rd, Woodbury, CT 06798

  Last Sold Summary

  • 25 Days On Market

  Last Listing Agent Michael Calabro Coldwell Banker Calabro
• 

  

  /32

  $289,000

  $61K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,920 Sq Ft

  439 Washington Rd, Woodbury, CT 06798

  Investors and Contractors take notice! This versatile office space located on close to 10 acres of rural Woodbury land is ripe with opportunity. The 1,920 sqft office can potentially be converted into a single family residential ranch overlooking the babbling Sprain Brook below. Across the brook, with road frontage and access off of Hoop Pole Hill Rd, lies the majority of the acreage with a dry,

  Matthew Amatruda Drakeley Real Estate, Inc.

  439 Washington 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 $630,107

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

  94 Old Town Farm Rd, Woodbury, CT 06798
• 

  Est $438,818

  Not Listed For Sale

  22 Lake Rd, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 2,008 Sq Ft
  • Built 1956

  22 Lake Rd, Woodbury, CT 06798

  Last Sold Summary

  • 46 Days On Market

  Last Listing Agent Matt Rose Keller Williams Realty
• 

  

  /29

  $199,900

  • 2 Beds
  • 1 Bath
  • 913 Sq Ft

  229 Bacon Pond Rd Unit 312, Woodbury, CT 06798

  Welcome to 229 Bacon Pond Rd Unit 312 - located in the Town In Country complex, this 2 bed/1 bath unit has been remodeled from top to bottom featuring a brand new kitchen, new flooring, and central air. Inside you'll find an open floor plan perfect for entertaining - the kitchen has been completely redesigned featuring new cabinets, quartz countertops, and stainless steel appliances. The modern

  Joe Rohinsky Coldwell Banker Realty

  229 Bacon Pond Rd Unit 312, Woodbury, CT 06798
• 

  $575,000

  Sold Jul 02, 2026

  2 Judd Hill Rd, Woodbury, CT 06798

  • 3 Beds
  • 2 Baths
  • 1,470 Sq Ft
  • Built 1958

  Last Sold Summary

  • 4% Below List Price
  • $391/SF
  • 48 Days On Market

  Current Estimated Value $567,770

  Last Listing Agent Tim Drakeley Drakeley Real Estate, Inc.

  2 Judd Hill Rd, Woodbury, CT 06798
• 

  Est $717,805

  Not Listed For Sale

  60 Main St S, Woodbury, CT 06798

  • 4 Beds
  • 2 Baths
  • 3,068 Sq Ft
  • Built 1829

  60 Main St S, Woodbury, CT 06798

  Last Sold Summary

  • 14 Days On Market

  Last Listing Agent Joyce Drakeley Drakeley Real Estate, Inc.

Showing Results 161 - 200, Page 5 of 18