Woodbury, CT Homes

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  /38

  $275,000

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

  9 Highpoint Ct Unit 116E, Woodbury, CT 06798

  Owner occupied and thoughtfully maintained since August of 2000. A perfect 1st or 2nd. home. Included: one car garage, plus one assigned parking space, a deck and patio for grilling. Notice the wooded privacy in the back. Inside a convenient kitchen, a breakfast nook (Or computer area etc.) There is a large living/dining room combo. The Fireplace is sealed shut for safety. However, w/permits, you

  Terry Lee Adams Adams & Adams Real Estate

  9 Highpoint Ct Unit 116E, Woodbury, CT 06798
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  $585,000 Sold Aug 27, 2025

  18 Grey Fox Trail, Woodbury, CT 06798

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

  Last Sold Summary

  • 10% Below List Price
  • $312/SF
  • 49 Days On Market

  Current Estimated Value $611,839

  Last Listing Agent Joseph Lorino Klemm Real Estate Inc

  18 Grey Fox Trail, Woodbury, CT 06798
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  Est $447,254 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

  • 6% Above List Price
  • $207/SF
  • 44 Days On Market

  Last Sold Price $420,000

  Last Listing Agent David Aurigemma Regency Real Estate, LLC
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  /30

  $585,000

  • 1 Bed
  • 2 Baths
  • 1,564 Sq Ft

  123 Cross Brook Rd, Woodbury, CT 06798

  Offered for the first time, this custom-built Cape was carefully designed with a vision for both comfortable living and future expansion. Currently configured for easy one-level living, the home features a spacious, well-built layout with hardwood floors and generously proportioned rooms throughout. Upstairs, a blank canvas awaits-ready to become additional bedrooms, a full bath, and expanded

  Jeff Boucher Drakeley Real Estate, Inc.

  123 Cross Brook Rd, Woodbury, CT 06798
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  $250,000 Sold Aug 29, 2025

  97 Westwood Rd, Woodbury, CT 06798

  • 2 Beds
  • 1 Bath
  • 1,264 Sq Ft
  • Built 1850

  Last Sold Summary

  • 11% Below List Price
  • $198/SF
  • 13 Days On Market

  Current Estimated Value $272,051

  Last Listing Agent Amy Vayan BHGRE Gaetano Marra Homes

  97 Westwood Rd, Woodbury, CT 06798
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  Est $472,331 Not Listed For Sale

  38 Woodbury Hill, Woodbury, CT 06798

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

  38 Woodbury Hill, Woodbury, CT 06798

  Last Sold Summary

  • 1% Above List Price
  • $261/SF
  • 32 Days On Market

  Last Sold Price $468,500

  Last Listing Agent Tim Drakeley Drakeley Real Estate, Inc.
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  /8

  $390,000 Under Contract

  • 2 Beds
  • 1 Bath
  • 1,421 Sq Ft

  43 Hoop Pole Hill Rd, Woodbury, CT 06798

  Nestled in one of Woodbury's most desirable areas, this nearly 9-acre property offers a rare opportunity for visionaries, developers, or those looking to create their own private retreat. The house and barn are in need of significant renovation - or start fresh and build your dream home surrounded by rolling hills, a meandering stream, mature trees, and the serene charm that defines Litchfield

  Laura Rose RE/MAX RISE

  43 Hoop Pole Hill Rd, Woodbury, CT 06798
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  $905,000 Sold Mar 28, 2025

  17 Birchwood Ln, Woodbury, CT 06798

  • 3 Beds
  • 3 Baths
  • 3,283 Sq Ft
  • Built 2008

  Last Sold Summary

  • 9% Below List Price
  • $276/SF
  • 80 Days On Market

  Current Estimated Value $961,717

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

  17 Birchwood Ln, Woodbury, CT 06798
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  Est $478,255 Not Listed For Sale

  236 Quassuk Rd, Woodbury, CT 06798

  • 3 Beds
  • 2 Baths
  • 1,606 Sq Ft
  • Built 1840

  236 Quassuk Rd, Woodbury, CT 06798

  Last Sold Summary

  • 9% Above List Price
  • $274/SF
  • 62 Days On Market

  Last Sold Price $440,000

  Last Listing Agent Kathryn Bassett William Pitt
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  /2

  $269,000 Under Contract

  • 2 Beds
  • 2 Baths
  • 1,456 Sq Ft

  14 Fox Run, Woodbury, CT 06798

  Quiet Corner House - expanded deck opens to level yard area offering privacy. The Corner House floor plan offers the expanded family room area with fireplace and exposed beams open to the kitchen. This FP is sealed. Hard wood flooring on the first level. New motor in heat pump just installed 2026. Windows, not brand new, but were replaced for efficiency. The baths and kitchen have not been

  Mary Ann Bennett Drakeley Real Estate, Inc.

  14 Fox Run, Woodbury, CT 06798
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  $300,000 Sold Sep 11, 2025

  1 Alder Ct Unit 1, Woodbury, CT 06798

  • 2 Beds
  • 2.5 Baths
  • 1,365 Sq Ft
  • Built 1974

  Last Sold Summary

  • $220/SF
  • 54 Days On Market

  Current Estimated Value $298,676

  Last Listing Agent Camilo Ramirez Higgins Group Real Estate

  1 Alder Ct Unit 1, Woodbury, CT 06798
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  Est $661,713 Not Listed For Sale

  167 Hazel Plain Rd, Woodbury, CT 06798

  • 4 Beds
  • 3.5 Baths
  • 2,922 Sq Ft
  • Built 1977

  167 Hazel Plain Rd, Woodbury, CT 06798

  Last Sold Summary

  • 20% Above List Price
  • $188/SF
  • 13 Days On Market

  Last Sold Price $550,000

  Last Listing Agent Kerri Dimitratos William Raveis Real Estate
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  /40

  $2,195,000

  • 4 Beds
  • 3.5 Baths
  • 3,551 Sq Ft

  382 Weekeepeemee Rd, Woodbury, CT 06798

  The Jesse Peck Lambert Homestead, built in 1805 & thoughtfully restored, provides a seamless blend of historic charm & modern comfort. Set on 6.42 acres in Northern Woodbury on the Washington border just 2 hours from NYC, this 4-bedroom/3.5-bath home provides a serene escape with timeless appeal. The newly designed kitchen is a chef's dream, featuring custom rift-sawn white oak cabinets, oiled

  Jeff Phillips William Pitt Sotheby's Int'l

  382 Weekeepeemee Rd, Woodbury, CT 06798
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  $1,050,000 Sold Jun 06, 2025

  17 Transylvania Rd, Woodbury, CT 06798

  • 4 Beds
  • 2.5 Baths
  • 3,928 Sq Ft
  • Built 2008

  Last Sold Summary

  • $267/SF
  • 34 Days On Market

  Current Estimated Value $1,045,559

  Last Listing Agent Michael Hvizdo Coldwell Banker Realty

  17 Transylvania Rd, Woodbury, CT 06798
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  Est $419,801 Not Listed For Sale

  61 Sherman Heights Rd, Woodbury, CT 06798

  • 2 Beds
  • 1 Bath
  • 924 Sq Ft
  • Built 1943

  61 Sherman Heights Rd, Woodbury, CT 06798

  Last Sold Summary

  • 11% Above List Price
  • $410/SF
  • 103 Days On Market

  Last Sold Price $379,000

  Last Listing Agent Taylor O'Keefe Drakeley Real Estate, Inc.
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  /17

  $499,000

  • 3 Beds
  • 2.5 Baths
  • 2,016 Sq Ft

  34 Transylvania Rd, Woodbury, CT 06798

  Charming Country Retreat- A perfect alternative to Condo Living! Nestled on a serene 3 acre lot with picturesque stream, this property offers the tranquility of country living while maintaining easy access to nearby amenities. One level living- enjoy the convenience of the primary bedroom with spacious walk-in closet on the same level as the open floor plan kitchen/dining/livingroom. The lower

  Betsy Rosa Berkshire Hathaway NE Prop.

  34 Transylvania Rd, Woodbury, CT 06798
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  $490,000 Sold Nov 20, 2025

  15 Lynns Corner Rd, Woodbury, CT 06798

  • 4 Beds
  • 3 Baths
  • 2,216 Sq Ft
  • Built 1948

  Last Sold Summary

  • $221/SF
  • 27 Days On Market

  Current Estimated Value $510,800

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

  15 Lynns Corner Rd, Woodbury, CT 06798
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  Est $1,846,395 Not Listed For Sale

  49 Owl Ridge Rd, Woodbury, CT 06798

  • 4 Beds
  • 5 Baths
  • 8,000 Sq Ft
  • Built 2006

  49 Owl Ridge Rd, Woodbury, CT 06798

  Last Sold Summary

  • 11% Above List Price
  • $208/SF
  • 135 Days On Market

  Last Sold Price $1,660,000

  Last Listing Agent Christian Jensen William Pitt
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  /38

  $450,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,620 Sq Ft

  133 White Deer Rocks Rd, Woodbury, CT 06798

  Price adjusted to accommodate cosmetic updates. Newer Beckett boiler, C/A, oil tank, and roof is approx. 9-10 years old! This unique, 1997 ranch-style home is set beautifully on nearly 2 acres of mostly level, private land with small pond in Historic Woodbury! The open floor plan of this home offers abundant natural light with a spacious eat-in kitchen, granite countertops, ample cabinetry,

  Michelle Pavia William Raveis Real Estate

  133 White Deer Rocks Rd, Woodbury, CT 06798
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  $415,000 Sold Jun 04, 2025

  23 Woodbury Hill, Woodbury, CT 06798

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

  Last Sold Summary

  • 8% Below List Price
  • $231/SF
  • 55 Days On Market

  Current Estimated Value $439,536

  Last Listing Agent Donna Bannon BHGRE Gaetano Marra Homes

  23 Woodbury Hill, Woodbury, CT 06798
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  /25

  Est $258,431 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

  • 45% Below List Price
  • $185/SF

  Last Sold Price $178,000

  Last Listing Agent Joel Matson Coldwell Banker Realty
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  /2

  $400,000

  • Land
  • 0.51 Acre
  • $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
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  $970,000 Sold Dec 09, 2025

  25 Curtiss Meadows, Woodbury, CT 06798

  • 4 Beds
  • 3.5 Baths
  • 3,113 Sq Ft
  • Built 2005

  Last Sold Summary

  • 1% Below List Price
  • $312/SF
  • 132 Days On Market

  Current Estimated Value $972,295

  Last Listing Agent Ralph Harvey ListWithFreedom.com

  25 Curtiss Meadows, Woodbury, CT 06798
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  Est $174,777 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

  • 13% Above List Price
  • $170/SF
  • 6 Days On Market

  Last Sold Price $155,000

  Last Listing Agent Mary Ann Bennett Drakeley Real Estate, Inc.
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  /22

  $239,000

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

  47 Woods Way Unit 47, Woodbury, CT 06798

  This Country House model, end unit in Woodbury's Woodlake community offers two spacious bedrooms, with their own full baths, a detached one car garage and open floor plan on the main level. The Woodlake community provides non-motorized boating on the lake, hiking trails, basketball, tennis courts, and a playground area to name a few. The full unfinished basement offers more storage space. New

  Katherine Parlato Drakeley Real Estate, Inc.

  47 Woods Way Unit 47, Woodbury, CT 06798
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  $330,000 Sold Apr 23, 2025

  42 Woods Way Unit 126F, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 1,640 Sq Ft
  • Built 1980

  Last Sold Summary

  • 10% Above List Price
  • $201/SF
  • 21 Days On Market

  Current Estimated Value $339,972

  Last Listing Agent Bonnie Wilson Berkshire Hathaway NE Prop.

  42 Woods Way Unit 126F, Woodbury, CT 06798
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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

  • $583/SF
  • 15 Days On Market

  Last Sold Price $1,210,000

  Last Listing Agent Maria Taylor Klemm Real Estate Inc
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  /27

  $200,000 Pending

  • 2 Beds
  • 1 Bath
  • 1,150 Sq Ft

  126 Sherman Hill Rd Unit B12, Woodbury, CT 06798

  This second level unit offers a living and dining combo, kitchen, two bedrooms and one full bath. Upstairs units have vaulted ceilings & additional windows that allow for even more daylight and sense of space. A floor to ceiling brick fireplace will draw you in the winter and a modern curved wall, as you enter the door, adds so much character. The complex offers an in-ground pool. HOA Includes

  Tiffany Clark RE/MAX Right Choice

  126 Sherman Hill Rd Unit B12, Woodbury, CT 06798
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  $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
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  Est $483,994 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

  • 13% Above List Price
  • $206/SF
  • 128 Days On Market

  Last Sold Price $427,000

  Last Listing Agent Karen Dibble-flaherty Keller Williams Realty
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  /32

  $314,900

  • 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
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  $850,000 Sold May 01, 2025

  258 Washington Rd, Woodbury, CT 06798

  • 3 Beds
  • 3 Baths
  • 1,628 Sq Ft
  • Built 1850

  Last Sold Summary

  • 4% Below List Price
  • $522/SF
  • 260 Days On Market

  Current Estimated Value $848,895

  Last Listing Agent Pat Lahoud Lahoud William Pitt Sotheby's Int'l

  258 Washington Rd, Woodbury, CT 06798
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  Est $444,236 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

  • 12% Above List Price
  • $192/SF
  • 233 Days On Market

  Last Sold Price $395,000

  Last Listing Agent Gary Smith eXp Realty
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  /40

  $799,000

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

  92 Minortown Rd, Woodbury, CT 06798

  Charming Gentleman's Farm on 5.76 Acres. Welcome to this beautifully maintained gentleman's farm, perfectly set on 5.76 level acres of open pasture and riding space. Ideal for horse enthusiasts, the property features four barns with a total of 10 stalls, two wash stalls, and a 20x60 meter riding arena with quality stone dust and sand footing. The grounds offer a wonderful mix of functionality and

  Heather Crabtree RE/MAX RISE

  92 Minortown Rd, Woodbury, CT 06798
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  $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 $225,856

  Last Listing Agent Jacki Hornish W. Raveis Lifestyles Realty

  12 Edgehill Ct, Woodbury, CT 06798
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  Est $1,335,124 Not Listed For Sale

  45 Birchwood Ln, Woodbury, CT 06798

  • 5 Beds
  • 5.5 Baths
  • 5,956 Sq Ft
  • Built 2004

  45 Birchwood Ln, Woodbury, CT 06798

  Last Sold Summary

  • 16% Above List Price
  • $193/SF
  • 15 Days On Market

  Last Sold Price $1,150,000

  Last Listing Agent Dawn Grabover Keller Williams Realty
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  /38

  $339,000 Under Contract

  • 2 Beds
  • 2 Baths
  • 1,267 Sq Ft

  10 Hazel Plain Rd, Woodbury, CT 06798

  Welcome to Sweet River Cottage, a charming riverside retreat offering the perfect blend of comfort, character, and natural beauty. This inviting 2-3 bedroom, 2 full bath home sits just steps from the water's edge, providing peaceful views and the soothing sound of the river year-round. Inside, you'll find a warm and welcoming eat-in kitchen, ideal for casual meals or gathering with friends. Enjoy

  Wendy Brazauskas Coldwell Banker Realty

  10 Hazel Plain Rd, Woodbury, CT 06798
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  $295,000 Sold May 15, 2025

  3 Woodbury Place Unit 3, Woodbury, CT 06798

  • 2 Beds
  • 1.5 Baths
  • 1,025 Sq Ft
  • Built 1979

  Last Sold Summary

  • 3% Below List Price
  • $288/SF
  • 29 Days On Market

  Current Estimated Value $302,082

  Last Listing Agent Katherine Parlato Drakeley Real Estate, Inc.

  3 Woodbury Place Unit 3, Woodbury, CT 06798
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  Est $190,227 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

  • $209/SF
  • 8 Days On Market

  Last Sold Price $191,000

  Last Listing Agent Ann Gerschefski William Raveis Real Estate
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  /38

  $289,900

  • 2 Beds
  • 2 Baths
  • 1,457 Sq Ft

  9 Upper Commons Unit 9, Woodbury, CT 06798

  Welcome to 9 Upper Commons, Woodbury - Tucked away in a quiet, well-maintained community surrounded by mature trees and walking trails, this inviting 2-bedroom townhouse offers three levels for a comfortable, functional lifestyle. The main level features a spacious open-concept floor plan, ideal for everyday living or entertaining. Sliding doors off the dining area leads to your private

  Athan Zeno William Raveis Real Estate

  9 Upper Commons Unit 9, Woodbury, CT 06798

Showing Results 121 - 160, Page 4 of 18