Woodbury, CT Homes

• 

  Est $889,187 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,447 Sq Ft

  18 River View Ln, Woodbury, CT 06798

  18 River View Ln, Woodbury, CT 06798
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  /30

  $849,000 Pending

  • 4 Beds
  • 4 Baths
  • 3,280 Sq Ft

  393 Middle Road Turnpike, Woodbury, CT 06798

  The Tomlinson House, built in 1783, offers a rare chance to own a piece of Woodbury's history. Set on 5+ acres along Middle Road Turnpike, with an additional .87-acres across the street, this 4-bedroom Colonial combines period charm with enduring potential. Historic character is evident throughout-restored wide-board hardwood floors, original millwork, and four (non-working) fireplaces, including

  Kathryn Bassett William Pitt Sotheby's Int'l

  393 Middle Road Turnpike, Woodbury, CT 06798
• 

  $180,000 Sold Mar 06, 2025

  229 Bacon Pond Rd Unit 241, Woodbury, CT 06798

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

  Last Sold Summary

  • 3% Below List Price
  • $197/SF
  • 34 Days On Market

  Current Estimated Value $185,714

  Last Listing Agent Taner Genc Coldwell Banker Realty

  229 Bacon Pond Rd Unit 241, Woodbury, CT 06798
• 

  Est $966,689 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,468 Sq Ft

  41 Curtiss Meadows, Woodbury, CT 06798

  41 Curtiss Meadows, Woodbury, CT 06798
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  /9

  $375,000 Under Contract

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

  437 Middle Road Turnpike, Woodbury, CT 06798

  Welcome to this well-positioned hidden gem, perfectly situated in one of the area's most desirable neighborhoods. This 3 bedroom 1 1/2 bath home features hardwood floors throughout, and one-floor living. Boasting a strategic location close to top-rated schools, shopping centers, fine dining options, and recreational facilities, this home offers unbeatable convenience and high demand from future

  Karen Dibble-flaherty Keller Williams Realty

  437 Middle Road Turnpike, Woodbury, CT 06798
• 

  $290,000 Sold May 09, 2025

  44 Woods Way Unit 44, Woodbury, CT 06798

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

  Last Sold Summary

  • $199/SF
  • 4 Days On Market

  Last Listing Agent Kristie Perry William Pitt Sotheby's Int'l

  44 Woods Way Unit 44, Woodbury, CT 06798
• 

  Est $1,107,951 Not Listed For Sale

  • 4 Beds
  • 5 Baths
  • 6,978 Sq Ft

  105 Old Grassy Hill Rd, Woodbury, CT 06798

  105 Old Grassy Hill Rd, Woodbury, CT 06798
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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
• 

  $499,000 Sold Jun 16, 2025

  98 Old Town Farm Rd, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 1,648 Sq Ft
  • Built 1972

  Last Sold Summary

  • 1% Above List Price
  • $303/SF
  • 3 Days On Market

  Current Estimated Value $499,727

  Last Listing Agent Jeff Boucher Drakeley Real Estate, Inc.

  98 Old Town Farm Rd, Woodbury, CT 06798
• 

  Est $902,479 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,334 Sq Ft

  434 Quassapaug Rd, Woodbury, CT 06798

  434 Quassapaug Rd, Woodbury, CT 06798
• 

  

  /19

  $339,000

  • 2 Beds
  • 1 Bath
  • 1,080 Sq Ft

  54 Mountain Rd, Woodbury, CT 06798

  Investors take note! 54 Mountain Road, Woodbury, CT Inside, it's nearly complete-outside, it's your chance to shine! With most interior renovations finished, this Woodbury gem just needs exterior touches to be truly spectacular. Best of all, the seller is motivated and willing to help make your vision a reality. Home is truly a diamond in the rough. Location Appeal: Situated in historic Woodbury,

  Gayle Forster Century 21 AllPoints Realty

  54 Mountain Rd, 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 $488,040

  Last Listing Agent Rhya Szymansky Drakeley Real Estate, Inc.

  3 Lynns Corner Rd, Woodbury, CT 06798
• 

  Est $202,669 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 913 Sq Ft

  229 Bacon Pond Rd Unit 342, Woodbury, CT 06798

  229 Bacon Pond Rd Unit 342, Woodbury, CT 06798
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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
• 

  $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

  Last Listing Agent Donna Doyle Keller Williams Realty

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

  Est $640,217 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,080 Sq Ft

  8 MacKay Farm Rd, Woodbury, CT 06798

  8 MacKay Farm Rd, Woodbury, CT 06798
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  /40

  $1,267,500 Pending

  • 4 Beds
  • 4.5 Baths
  • 4,676 Sq Ft

  101 Old Grassy Hill Rd, Woodbury, CT 06798

  "Where Luxury Meets the Landscape." Welcome to a home where nature and craftsmanship converge in breathtaking harmony. Nestled on five professionally landscaped acres, this country manor is a sanctuary of serenity and sophistication. A statuesque quarry of stone lines one side of the property, perfectly balanced by a tranquil body of water-inviting you to kayak, canoe, or skate through the

  Deborah Cody Coldwell Banker Realty

  101 Old Grassy Hill Rd, Woodbury, CT 06798
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  $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
• 

  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 894 Sq Ft

  72 Washington Rd Unit 34, Woodbury, CT 06798

  72 Washington Rd Unit 34, Woodbury, CT 06798
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  /21

  $749,900

  • 4 Beds
  • 4 Baths
  • 2,980 Sq Ft

  432 Quassapaug Rd, Woodbury, CT 06798

  Welcome to Eastfield Farms Etates. This Colonial features an open floor plan for comfortable everyday living an entertaining alike. The large foyer flows to both the formal living room with french doors and formal dining room. Both with crown molding and accent lighting. Just down the hall step into the spacious kitchen with center island, granite counter tops stainless appliances. The dining

  Ray Manzi Manzi Real Estate

  432 Quassapaug 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 $288,354

  Last Listing Agent Christina Moulthrop Showcase Realty, Inc.

  2 Edgehill Ct, Woodbury, CT 06798
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  Est $387,776 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,212 Sq Ft

  406 Transylvania Rd, Woodbury, CT 06798

  406 Transylvania Rd, Woodbury, CT 06798
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  /24

  $339,000

  • 2 Beds
  • 2.5 Baths
  • 1,895 Sq Ft

  13 Tamarack Ln Unit 13, Woodbury, CT 06798

  Beautiful end unit at Woodlake Community in Woodbury! Kitchen with stainless steel appliances and granite countertops plus tile floors. Hardwood floors on first level in Dining and living area with sliders to a deck overlooking the wooded back area and lake. This unit features upgraded 2 full plus 1 half bathrooms plus 2 bedrooms with plenty of closets. Laundry closet with shelving is on the

  Lynn Platania William Raveis Real Estate

  13 Tamarack Ln Unit 13, Woodbury, CT 06798
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  $191,000 Sold Jan 13, 2025

  229 Bacon Pond Rd Unit 154, Woodbury, CT 06798

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

  Last Sold Summary

  • 1% Above List Price
  • $209/SF
  • 66 Days On Market

  Current Estimated Value $199,053

  Last Listing Agent Sacha Armstrong William Pitt Sotheby's International Realty

  229 Bacon Pond Rd Unit 154, Woodbury, CT 06798
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  Est $620,556 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,946 Sq Ft

  233 Old Sherman Hill Rd, Woodbury, CT 06798

  233 Old Sherman Hill Rd, Woodbury, CT 06798
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  /40

  $377,750

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

  2 South Meadows Unit 107B, Woodbury, CT 06798

  Take another look! Seller Contingency removed! Welcome Home to your new dream home! This beautiful, peaceful, calm upscale residence, offers 3 Levels of quiet elegance. Move in & enjoy the vacation at home..."Woodlake Life Style". Each room is thoughtfully purposed and decorated with a classy style. The kitchen spacious "open" concept, with Corian countertops. Cherry toned flooring adds a warm

  Terry Lee Adams Adams & Adams Real Estate

  2 South Meadows Unit 107B, Woodbury, CT 06798
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  $220,000 Sold Mar 13, 2025

  74 Washington Rd Unit 14, Woodbury, CT 06798

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

  Last Sold Summary

  • $229/SF
  • 31 Days On Market

  Current Estimated Value $225,937

  Last Listing Agent Carole Sansone William Raveis Real Estate

  74 Washington Rd Unit 14, Woodbury, CT 06798
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  Est $948,745 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 3,179 Sq Ft

  40 Stonefield Rd, Woodbury, CT 06798

  40 Stonefield Rd, Woodbury, CT 06798
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  /40

  $569,000 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 3BR, 2BA home set on nearly an acre along a quiet country road in Woodbury. The inviting main level features a cozy living room with a fireplace, a spacious first-floor bedroom, and a full bath-perfect for guests or one-level living. A newly updated kitchen opens to the dining area and leads directly to a brand-new deck

  Meg George Higgins Group Bedford Square

  2 Judd Hill Rd, Woodbury, CT 06798
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  $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 $552,533

  Last Listing Agent Ron Nettleton William Raveis Real Estate

  259 Old Town Farm Rd, Woodbury, CT 06798
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  Est $363,912 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,388 Sq Ft

  11 Boxwood Ct, Woodbury, CT 06798

  11 Boxwood Ct, Woodbury, CT 06798
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  /39

  $725,000

  • 4 Beds
  • 2.5 Baths
  • 2,874 Sq Ft

  74 Middle Quarter Rd, Woodbury, CT 06798

  Welcome to a piece of New England history-an 1835 Farmhouse lovingly updated for today's living while preserving all its timeless charm. Set on 4.7 acres with a sun-kissed field framed by quiet woodlands, this property offers the perfect balance of country serenity and in-town convenience. From here, you can stroll into the heart of Woodbury, known for its storybook charm, delightful restaurants,

  Heather Crabtree RE/MAX RISE

  74 Middle Quarter Rd, Woodbury, CT 06798
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  $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
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  Est $1,109,890 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 5,352 Sq Ft

  45 Old Meadow Rd, Woodbury, CT 06798

  45 Old Meadow Rd, Woodbury, CT 06798
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  /40

  $675,000 Pending

  • 4 Beds
  • 3 Baths
  • 3,064 Sq Ft

  174 Weekeepeemee Rd, Woodbury, CT 06798

  Nestled on approximately 5.38 acres of lush, mature landscaping, this captivating house offers an abundance of space and tranquility. The property features four bedrooms and three bathrooms, spanning approximately 3,064 square feet of thoughtfully designed living space. The expansive, spacious lot is complemented by a serene outdoor space, boasting a paved patio, a spacious deck, and a sprawling,

  Laureen Kennedy Coldwell Banker Realty

  174 Weekeepeemee Rd, Woodbury, CT 06798
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  $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

  Last Listing Agent Holly Mullins Coldwell Banker Realty

  10 Lake Rd, Woodbury, CT 06798
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  Est $924,756 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,693 Sq Ft

  20 Birchwood Ln, Woodbury, CT 06798

  20 Birchwood Ln, Woodbury, CT 06798
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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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  $260,000 Sold Apr 01, 2025

  31 Woods Way Unit 31, Woodbury, CT 06798

  • 2 Beds
  • 2 Baths
  • 1,582 Sq Ft
  • Built 1980

  Last Sold Summary

  • 9% Below List Price
  • $164/SF
  • 213 Days On Market

  Last Listing Agent Eli Carneiro William Raveis Real Estate

  31 Woods Way Unit 31, Woodbury, CT 06798
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  Est $399,680 Not Listed For Sale

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

  354 Quassapaug Rd, Woodbury, CT 06798

  354 Quassapaug Rd, Woodbury, CT 06798

Showing Results 81 - 120, Page 3 of 18