Woodbury, CT Homes

• 

  $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 $219,686

  Last Listing Agent Donna Doyle Keller Williams Realty

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

  Est $561,308 Not Listed For Sale

  80 Flanders Rd, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 2,165 Sq Ft
  • Built 1950

  80 Flanders Rd, Woodbury, CT 06798

  Last Sold Summary

  • 22% Below List Price
  • $333/SF
  • 3 Days On Market

  • Last Sold Price $720,000
  • May 19, 2023

  Last Listing Agent Sandra Kerr Berkshire Hathaway Home Services
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  /40

  $749,000 Under Contract

  • 3 Beds
  • 3.5 Baths
  • 3,749 Sq Ft

  19 Hillview Ln, Woodbury, CT 06798

  Nestled within the exclusive South Brook community, 19 Hill View Lane offers timeless New England charm paired with exceptional craftsmanship. This beautifully appointed 3 bedroom, 3.5 bath cape colonial is rich in architectural detail, featuring refined millwork, quality finishes, and a thoughtful layout designed for both everyday living and elegant entertaining. The main living spaces flow

  Nicole Fiorelli Fiorelli Realty, LLC

  19 Hillview Ln, 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 $311,945

  Last Listing Agent Danielle Rownin Keller Williams Realty

  2 Linden Rd, Woodbury, CT 06798
• 

  Est $496,878 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

  • 6% Above List Price
  • $162/SF
  • 36 Days On Market

  • Last Sold Price $470,000
  • Jan 08, 2025

  Last Listing Agent Tim Drakeley Drakeley Real Estate, Inc.
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  /34

  $1,675,000

  • 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
• 

  $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
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  /40

  Est $200,018 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

  • $219/SF

  • Last Sold Price $200,000

  Last Listing Agent Cheryl Vitale Berkshire Hathaway Home Services
• 

  /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
• 

  $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 $296,640

  Last Listing Agent Christina Moulthrop Showcase Realty, Inc.

  2 Edgehill Ct, Woodbury, CT 06798
• 

  Est $281,471 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

  • 4% Above List Price
  • $228/SF
  • 55 Days On Market

  • Last Sold Price $270,000
  • May 02, 2024

  Last Listing Agent Wendy Brazauskas Coldwell Banker Realty
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  /36

  $470,000 Under Contract

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

  5 Kimberly Ln, Woodbury, CT 06798

  Welcome to this beautifully maintained 3-bedroom, 3-bath high ranch nestled in the picturesque New England town of Woodbury. This inviting home offers a perfect blend of comfort, functionality, and modern updates. The upper level features gleaming hardwood floors throughout and an updated kitchen that flows seamlessly into an open-concept dining and living area-ideal for both everyday living and

  Heather Crabtree RE/MAX RISE

  5 Kimberly Ln, 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 $533,884

  Last Listing Agent Tim Drakeley Drakeley Real Estate, Inc.

  18 Woodbury Hill, Woodbury, CT 06798
• 

  Est $829,747 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

  • 12% Above List Price
  • $216/SF
  • 59 Days On Market

  • Last Sold Price $743,400
  • Nov 15, 2023

  Last Listing Agent Wendy Brazauskas Coldwell Banker Realty
• 

  

  /20

  $499,900

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

  43 Bethwood Ln, Woodbury, CT 06798

  If you're looking for your own piece of heaven, this may be it. Hard to find and full of potential, this modest single-level home is set on a secluded 5+ acre parcel of gorgeous open meadow. Located on a private road near the Woodbury/Bethlehem line, the home offers three bedrooms, an eat-in kitchen, dining room, living room with fireplace, breezeway, and an attached two-car garage. With only a

  Tim Drakeley Drakeley Real Estate, Inc.

  43 Bethwood Ln, 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 $919,949 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

  • $264/SF
  • 38 Days On Market

  • Last Sold Price $916,000
  • Sep 06, 2024

  Last Listing Agent Mary Ann Bennett Drakeley Real Estate, Inc.
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  /40

  $377,750

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

  2 South Meadows Unit 2, Woodbury, CT 06798

  Spring-Ahead & Welcome Home...to an upscale residence w/3 levels of quiet elegance. Enjoy the vacation at home..."Woodlake Life Style". Each room is thoughtfully purposed and decorated with a classy style. A spacious "open" concept kitchen includes "Corian" countertops. Cherry toned flooring adds a warm welcome to the first floor, as does the working fireplace. The 1st., floor powder room is

  Terry Lee Adams Adams & Adams Real Estate

  2 South Meadows Unit 2, 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 $572,962

  Last Listing Agent Ron Nettleton William Raveis Real Estate

  259 Old Town Farm Rd, Woodbury, CT 06798
• 

  Est $1,059,679 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

  • 24% Above List Price
  • $123/SF
  • 142 Days On Market

  • Last Sold Price $855,900
  • Apr 26, 2024

  Last Listing Agent Brian Hunter Hunter Realty Group
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  /17

  $595,000

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

  437 Middle Road Turnpike, Woodbury, CT 06798

  Completely renovated and move-in ready, this single-floor ranch offers effortless living with modern updates throughout. The brand-new kitchen is absolutely stunning and opens to the dining and living area, making the space perfect for both everyday comfort and entertaining. Enjoy peace of mind with all-new bathrooms, windows, lighting fixtures and a newly installed septic system. Other upgrades

  Erin Loucks BHGRE Gaetano Marra Homes

  437 Middle Road Turnpike, 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 $186,140 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

  • 5% Below List Price
  • $214/SF
  • 66 Days On Market

  • Last Sold Price $195,000
  • Jan 15, 2025

  Last Listing Agent Barbara Podlisny William Raveis Real Estate
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  /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
• 

  $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 $376,282

  Last Listing Agent Holly Mullins Coldwell Banker Realty

  10 Lake Rd, Woodbury, CT 06798
• 

  Est $463,362 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

  • 8% Above List Price
  • $171/SF
  • 162 Days On Market

  • Last Sold Price $430,000
  • Apr 04, 2025

  Last Listing Agent Katherine Parlato Drakeley Real Estate, Inc.
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  $145,000 Under Contract

  • 2 Beds
  • 1 Bath
  • 913 Sq Ft

  229 Bacon Pond Rd Unit 453, Woodbury, CT 06798

  Light-filled upper-level unit featuring hardwood floors throughout, located near Woodbury Town Center. The living room offers a fireplace, vaulted ceilings, and sliders to a private deck overlooking park-like grounds. The kitchen opens to the dining area with bar seating and an open floor plan. Spacious bedrooms include large closets, and the full bath offers a tub/shower. Close to the in-ground

  Deborah Snopkowski Coldwell Banker Realty

  229 Bacon Pond Rd Unit 453, 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 $571,678

  Last Listing Agent Christina Zainc BHGRE Gaetano Marra Homes

  9 Hill View Ln, Woodbury, CT 06798
• 

  Est $771,869 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

  • 14% Above List Price
  • $204/SF
  • 118 Days On Market

  • Last Sold Price $680,000
  • Oct 05, 2023

  Last Listing Agent Mary Ann Hebert BHGRE Gaetano Marra Homes
• 

  

  /19

  $399,000 Pending

  • 3 Beds
  • 1 Bath
  • 1,296 Sq Ft

  360 Old Sherman Hill Rd, Woodbury, CT 06798

  Come view this charming 3 bedroom, 2 full bath, single family home in beautiful Woodbury! Enjoy an above ground pool with a deck wrapped around it-perfect for relaxing year round while taking in the sweeping natural views out back. A spacious 2 car detached garage sits in the middle of a large private semi-circular driveway, offering plenty of parking and storage. Upon entering the front of the

  Levi Judqin Brass Moon Realty

  360 Old Sherman Hill Rd, 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 $413,824

  Last Listing Agent Donna J. Matula William Raveis Real Estate

  70 Mountain Rd, Woodbury, CT 06798
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  Est $197,597 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

  • 4% Above List Price
  • $208/SF
  • 16 Days On Market

  • Last Sold Price $190,000
  • Apr 24, 2024

  Last Listing Agent Lemon DeLucia Coldwell Banker Realty
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  /34

  $549,000

  • 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
• 

  $640,000 Sold Nov 20, 2025

  32 Plumb Brook Rd, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 2,252 Sq Ft
  • Built 1979

  Last Sold Summary

  • 3% Below List Price
  • $284/SF
  • 54 Days On Market

  Current Estimated Value $664,890

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

  32 Plumb Brook Rd, Woodbury, CT 06798
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  Est $575,474 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

  • 15% Above List Price
  • $240/SF
  • 2 Days On Market

  • Last Sold Price $500,000
  • Aug 21, 2023

  Last Listing Agent Shelley Drakeley Drakeley Real Estate, Inc.
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  /40

  $350,000

  • 3 Beds
  • 2.5 Baths
  • 1,640 Sq Ft

  24 Woods Way Unit 122A, Woodbury, CT 06798

  An updated condo w/modern overtones for you! Comfort and updated style greet you in this spacious, airy, end unit! 3 Spacious Bedrooms and 2.5 oversized bathrooms for your living enjoyment. The Condo has been tastefully renovated and professionally cleaned for your move-in-day! The Homestead floor plan provides a Galley Kitchen with a "great-room application". This is a lovely space to utilize as

  Terry Lee Adams Adams & Adams Real Estate

  24 Woods Way Unit 122A, Woodbury, CT 06798
• 

  $35,000 Sold Nov 20, 2025

  0 Main St N Unit 24119173, Woodbury, CT 06798

  • Land
  • 3.6 Acres
  • $9,722 per Acre

  Last Sold Summary

  • 46% Below List Price
  • 57 Days On Market

  Last Listing Agent Jeff Boucher Drakeley Real Estate, Inc.

  0 Main St N Unit 24119173, Woodbury, CT 06798
• 

  Est $566,414 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

  • 6% Below List Price
  • $308/SF
  • 39 Days On Market

  • Last Sold Price $600,000
  • Oct 25, 2024

  Last Listing Agent Maria Taylor Klemm Real Estate Inc
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  /34

  $499,000

  • 3 Beds
  • 2 Baths
  • 1,548 Sq Ft

  6 Weekeepeemee Rd, Woodbury, CT 06798

  Step back in time as you enter this enchanting 1846 cottage, where history and modern comfort blend seamlessly. Wide-board wood floors and exposed hand-hewn beams welcome you the moment you arrive, guiding you through rooms filled with character and warmth. The open-concept kitchen features a stainless steel gas stove and dishwasher, charming display cabinets, a farmhouse sink, and a delightful

  Dawn Hough Coldwell Banker Realty

  6 Weekeepeemee Rd, Woodbury, CT 06798
• 

  $700,000 Sold Jul 02, 2025

  16 Fairgrounds Rd, Woodbury, CT 06798

  • 4 Beds
  • 2.5 Baths
  • 2,614 Sq Ft
  • Built 1998

  Last Sold Summary

  • 1% Above List Price
  • $268/SF
  • 47 Days On Market

  Current Estimated Value $751,967

  Last Listing Agent Taylor O'Keefe Drakeley Real Estate, Inc.

  16 Fairgrounds Rd, Woodbury, CT 06798

Showing Results 81 - 120, Page 3 of 18