Woodbury, CT Homes

• 

  

  

  /24

  $289,000

  $30K PRICE DROP

  • 2 Beds
  • 3 Baths
  • 1,059 Sq Ft

  3 Tamarack Ln Unit 3, Woodbury, CT 06798

  Welcome to this well-maintained condo offering comfortable living in a desirable Woodbury location. This inviting unit features a bright and open layout with spacious living areas, an updated kitchen, and generously sized bedrooms. Enjoy the ample storage and a private outdoor space perfect for relaxing or entertaining. Nestled in a quiet, well-kept complex close to local shops, dining, and major

  Stephen Mele Houlihan Lawrence

  3 Tamarack Ln Unit 3, Woodbury, CT 06798
• Selling your home? Sell it faster and for more with a Homes.com Boost.

  Learn More
• 

  

  

  /22

  $1,900 Per Month

  • 2 Beds
  • 1 Bath
  • 1,100 Sq Ft
  • House for Rent

  4 Weekeepeemee Rd, Woodbury, CT 06798

  Large bright, natural light filled apartment. Second floor with front and back private porches. Living room is very spacious with built ins. Hard wood flooring. Freshly painted - Ready for immediate occupancy. This is a second floor unit. Rear yard is recently cleared and seeded for all tenants to enjoy. Square footage is approximate. Preference is no pets, but will discuss on case by case basis.

  Mary Ann Bennett Drakeley Real Estate, Inc.

  4 Weekeepeemee Rd, Woodbury, CT 06798
• 

  $595,000

  Sold Nov 03, 2025

  90 Railtree Hill Rd, Woodbury, CT 06798

  • 3 Beds
  • 2 Baths
  • 2,772 Sq Ft
  • Built 1983

  Last Sold Summary

  • 6% Above List Price
  • $215/SF
  • 28 Days On Market

  Current Estimated Value $597,125

  Last Listing Agent Matthew Amatruda Drakeley Real Estate, Inc.

  90 Railtree Hill Rd, Woodbury, CT 06798
• 

  Not Listed For Sale

  267 Good Hill Rd, Woodbury, CT 06798

  • 3 Beds
  • 4 Baths
  • 3,349 Sq Ft
  • Built 1790

  267 Good Hill Rd, Woodbury, CT 06798

  Last Sold Summary

  • 54 Days On Market
• 

  

  

  /20

  $499,900

  Pending

  • 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
• 

  

  /9

  $2,000 Per Month

  • 2 Beds
  • 1 Bath
  • 6,097 Sq Ft
  • House for Rent

  107 Main St N, Woodbury, CT 06798

  2 BEDROOM - BRAND NEW REMODEL - NEW kITCHEN - BATH TOP TO BOTTOM CENTRAL AIR- WASHER & DRYER INCLUDED AND OFF STREET PARKING

  Pat Civitella Civitella Real Estate LLC

  107 Main St N, Woodbury, CT 06798
• 

  $125,000

  Sold Sep 16, 2025

  14 Arrowhead Way Unit 6, Woodbury, CT 06798

  • 1 Bed
  • 1 Bath
  • 546 Sq Ft
  • Built 1965

  Last Sold Summary

  • 4% Below List Price
  • $229/SF
  • 91 Days On Market

  Current Estimated Value $124,321

  Last Listing Agent Jeff Boucher Drakeley Real Estate, Inc.

  14 Arrowhead Way Unit 6, Woodbury, CT 06798
• 

  Est $184,622

  Not Listed For Sale

  229 Bacon Pond Rd Unit 132, Woodbury, CT 06798

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

  229 Bacon Pond Rd Unit 132, Woodbury, CT 06798

  Last Sold Summary

  • 56 Days On Market
• 

  

  /40

  $347,500

  $30K PRICE DROP Under Contract

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

  2 South Meadows Unit 2, Woodbury, CT 06798

  New Price-Point on this lovely upscale residence! Don't miss the opportunity for a vacation at home "Woodlake Life Style" Each room is thoughtfully purposed and decorated with classy features.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 oversized &

  Terry Lee Adams Adams & Adams Real Estate

  2 South Meadows Unit 2, Woodbury, CT 06798
• 

  

  /37

  $7,500 Per Month

  • 4 Beds
  • 2.5 Baths
  • 3,159 Sq Ft
  • House for Rent

  260 White Deer Rocks Rd, Woodbury, CT 06798

  There is no better place to spend your time in Litchfield County than the town of Woodbury. Honored as "Connecticut's most charming town" you have access to award-winning dining (indoor & outdoor), local farms & CSA's, natural food stores, spa's, vineyards & breweries, antique shops, golf courses, bike trails, lakes & hiking - all minutes away from this centrally located property. This home's

  Michael Caporizzo William Pitt Sotheby's Int'l

  260 White Deer Rocks Rd, Woodbury, CT 06798
• 

  $449,900

  Sold Aug 08, 2025

  67 Flanders Rd, Woodbury, CT 06798

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

  Last Sold Summary

  • $163/SF
  • 25 Days On Market

  Current Estimated Value $494,869

  Last Listing Agent Michael Calabro Coldwell Banker Calabro

  67 Flanders Rd, Woodbury, CT 06798
• 

  Est $173,624

  Not Listed For Sale

  229 Bacon Pond Rd Unit 142, Woodbury, CT 06798

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

  229 Bacon Pond Rd Unit 142, Woodbury, CT 06798

  Last Sold Summary

  • 60 Days On Market
• 

  

  /27

  $545,000

  • 2 Beds
  • 2.5 Baths
  • 1,673 Sq Ft

  17 Woodbury Hill Unit 17, Woodbury, CT 06798

  The finest condo complex in one of Litchfield Counties most charming towns! Woodbury Hill is a lovely community of townhouse style homes in a very attractive setting and features a saltwater pool and tennis/pickleball courts. #17 has seen many upgrades over the past dozen years including new windows, renovated kitchen and baths, upgraded heat pump HVAC and water heater, as well as recent paint

  Justin Bette Century 21 Bette Real Estate

  17 Woodbury Hill Unit 17, Woodbury, CT 06798
• 

  $310,000

  Sold Apr 13, 2026

  4 Heather Ct Unit 4, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 1,888 Sq Ft
  • Built 1974

  Last Sold Summary

  • $164/SF
  • 82 Days On Market

  Last Listing Agent Jenn Lailer BHGRE Gaetano Marra Homes

  4 Heather Ct Unit 4, Woodbury, CT 06798
• 

  Est $453,428

  Not Listed For Sale

  87 Minortown Rd, Woodbury, CT 06798

  • 3 Beds
  • 1.5 Baths
  • 1,615 Sq Ft
  • Built 1965

  87 Minortown Rd, Woodbury, CT 06798

  Last Sold Summary

  • 91 Days On Market
• 

  

  /39

  $286,000

  $13K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,708 Sq Ft

  19 Clubhouse Dr, Woodbury, CT 06798

  At Woodlake, you're not just buying a home, you're buying a lifestyle. From being FHA Approved condos, to water views at every balcony, trail walks to boat rides to fountains and everything in between, Woodlake truly offers the peaceful, serene setting that we all dream of. This 3 bedroom, 2.5 bath freshly painted end unit has endless possibilities. Need a main level bedroom or office? One can be

  Macey Mazzella RE/MAX RISE

  19 Clubhouse Dr, Woodbury, CT 06798
• 

  $522,500

  Sold Feb 18, 2026

  667 Upper Grassy Hill Rd, Woodbury, CT 06798

  • 4 Beds
  • 2 Baths
  • 1,987 Sq Ft
  • Built 1973

  Last Sold Summary

  • 5% Below List Price
  • $263/SF
  • 75 Days On Market

  Current Estimated Value $534,032

  Last Listing Agent Rhya Szymansky Drakeley Real Estate, Inc.

  667 Upper Grassy Hill Rd, Woodbury, CT 06798
• 

  Not Listed For Sale

  126 Sherman Hill Rd Unit B8, Woodbury, CT 06798

  • 2 Beds
  • 1.5 Baths
  • 1,150 Sq Ft
  • Built 1964

  126 Sherman Hill Rd Unit B8, Woodbury, CT 06798

  Last Sold Summary

  • 54 Days On Market
• 

  

  /17

  $545,000

  $50K PRICE DROP

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

  437 Middle Road Turnpike, Woodbury, CT 06798

  Everything has already been done for you. Just move in, unpack, and enjoy the ease of single-floor living in this beautifully renovated ranch with endless potential below. Completely renovated and truly move-in ready, this home offers effortless living with every major updated already completed. From the brand-new HVAC system and newly installed septic to new windows, lighting, interior and

  Erin Loucks BHGRE Gaetano Marra Homes

  437 Middle Road Turnpike, Woodbury, CT 06798
• 

  $128,500

  Sold Jul 23, 2025

  16 Pilgrim Trail Unit F2, Woodbury, CT 06798

  • 1 Bed
  • 1 Bath
  • 546 Sq Ft
  • Built 1965

  Last Sold Summary

  • $235/SF
  • 19 Days On Market

  Current Estimated Value $125,955

  Last Listing Agent Karen Rigopulos West View Properties, LLC

  16 Pilgrim Trail Unit F2, Woodbury, CT 06798
• 

  Est $473,519

  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

  • 36 Days On Market
• 

  

  /40

  $675,000

  • 3 Beds
  • 2.5 Baths
  • 2,360 Sq Ft

  674 Middle Road Turnpike, Woodbury, CT 06798

  Meticulously maintained and handsomely set on a picturesque lot in charming Woodbury, Connecticut, this classic Colonial offers the perfect blend of timeless character, comfort, and outdoor beauty. From the moment you arrive, the home makes a lasting impression with its mature tree-lined setting, stone walls, flowering gardens, cobblestone and bluestone walkway, and inviting front entry. Inside,

  Chris Carbone HomeSmart Homes and Estates

  674 Middle Road Turnpike, Woodbury, CT 06798
• 

  $513,000

  Sold Jun 22, 2026

  242 Bacon Pond Rd, Woodbury, CT 06798

  • 4 Beds
  • 2 Baths
  • 1,836 Sq Ft
  • Built 1782

  Last Sold Summary

  • 8% Above List Price
  • $279/SF
  • 81 Days On Market

  Current Estimated Value $472,945

  Last Listing Agent Tim Drakeley Drakeley Real Estate, Inc.

  242 Bacon Pond Rd, Woodbury, CT 06798
• 

  Est $192,660

  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

  • 22 Days On Market
• 

  

  /40

  $275,000

  Pending

  • 3 Beds
  • 1.5 Baths
  • 1,562 Sq Ft

  6 Easy St, Woodbury, CT 06798

  ** INVESTORS TAKE NOTICE! ** Nestled in the desirable town of Woodbury, this 3 bedroom, 1.5 bath Colonial presents a unique opportunity to restore and reimagine a property full of charm and potential. Featuring hardwood flooring throughout the majority, spacious interiors, newer appliances, and some more recently installed mechanicals, this home offers a solid foundation for renovation and

  Jessica Caruso Berkshire Hathaway NE Prop.

  6 Easy St, Woodbury, CT 06798
• 

  $370,000

  Sold Dec 29, 2025

  298 Railtree Hill Rd, Woodbury, CT 06798

  • 3 Beds
  • 2 Baths
  • 1,510 Sq Ft
  • Built 1967

  Last Sold Summary

  • 10% Below List Price
  • $245/SF
  • 95 Days On Market

  Last Listing Agent Shawna Mucherino Coldwell Banker Realty

  298 Railtree Hill Rd, Woodbury, CT 06798
• 

  Est $318,392

  Not Listed For Sale

  51 Joshua Hill Rd, Woodbury, CT 06798

  • 3 Beds
  • 1.5 Baths
  • 1,508 Sq Ft
  • Built 1960

  51 Joshua Hill Rd, Woodbury, CT 06798

  Last Sold Summary

  • 10 Days On Market
• 

  

  /37

  $1,795,000

  • 2 Beds
  • 2 Baths
  • 1,197 Sq Ft

  112 W Lake Rd Unit 112, Woodbury, CT 06798

  Just 2 hours from New York City, this exceptional lakefront retreat offers a rare blend of privacy, natural beauty & turnkey luxury. Tucked at the end of West Lake Rd and bordered by the protected woodlands of Flanders Nature Center Preserve, the property enjoys sweeping, unobstructed views across pristine Lake Quassapaug to historic Tranquillity Farm, designed by McKim, Mead & White. Lake

  Karla Murtaugh Compass Connecticut, LLC

  112 W Lake Rd Unit 112, Woodbury, CT 06798
• 

  $439,900

  Sold Sep 02, 2025

  22 Lake Rd, Woodbury, CT 06798

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

  Last Sold Summary

  • $219/SF
  • 46 Days On Market

  Current Estimated Value $431,560

  Last Listing Agent Matt Rose Keller Williams Realty

  22 Lake Rd, Woodbury, CT 06798
• 

  Est $280,446

  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

  • 55 Days On Market
• 

  

  /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
• 

  $850,000

  Sold Oct 29, 2025

  84 Hurds Hill Rd, Woodbury, CT 06798

  • 4 Beds
  • 2.5 Baths
  • 3,736 Sq Ft
  • Built 1966

  Last Sold Summary

  • 4% Below List Price
  • $228/SF
  • 135 Days On Market

  Current Estimated Value $877,143

  Last Listing Agent Michael Vartolone William Raveis Real Estate

  84 Hurds Hill Rd, Woodbury, CT 06798
• 

  Est $851,429

  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

  • 59 Days On Market
• 

  

  /35

  $895,000

  Open Sun 10AM - 12PM

  • 4 Beds
  • 2.5 Baths
  • 2,283 Sq Ft

  253 Bacon Pond Rd, Woodbury, CT 06798

  Welcome to Bacon Pond House. A seamless blend of 19th-century soul and 21st-century luxury. Situated on over 3 acres, this antique Colonial has been thoughtfully revived to honor its heritage while offering every modern convenience. The interior, lovingly brought back to life, features wide-plank flooring and exposed hand-hewn beams that anchor the home's historic character. The rooms are

  Christian Jensen William Pitt Sotheby's Int'l

  253 Bacon Pond Rd, Woodbury, CT 06798
• 

  $1,075,000

  Sold Aug 21, 2025

  5 Blueberry Ln, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 3,874 Sq Ft
  • Built 2006

  Last Sold Summary

  • 8% Above List Price
  • $277/SF
  • 36 Days On Market

  Current Estimated Value $1,106,800

  Last Listing Agent John Donato Jr Showcase Realty, Inc.

  5 Blueberry Ln, Woodbury, CT 06798
• 

  Est $897,099

  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

  • 38 Days On Market
• 

  

  /33

  $575,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,961 Sq Ft

  5 Westwood Rd, Woodbury, CT 06798

  Classic early-1900s colonial in the heart of Woodbury with 3 bedrooms, 2 full baths, and over 1,900 square feet of living space. The home offers a comfortable mix of older-home character and practical updates, with hardwood floors, good natural light, and a layout that works well for everyday living. The updated kitchen features white cabinetry, granite counters, stainless steel appliances,

  Brad Harriman RJ Real Estate

  5 Westwood Rd, Woodbury, CT 06798
• 

  $665,000

  Sold May 26, 2026

  74 Middle Quarter Rd, Woodbury, CT 06798

  • 4 Beds
  • 2.5 Baths
  • 2,874 Sq Ft
  • Built 1835

  Last Sold Summary

  • 3% Below List Price
  • $231/SF
  • 47 Days On Market

  Current Estimated Value $683,497

  Last Listing Agent Jennifer Kelley Compass Connecticut, LLC

  74 Middle Quarter Rd, Woodbury, CT 06798
• 

  Est $453,868

  Not Listed For Sale

  23 Woodbury Hill, Woodbury, CT 06798

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

  23 Woodbury Hill, Woodbury, CT 06798

  Last Sold Summary

  • 55 Days On Market
• 

  

  /26

  $279,500

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

  48 Woods Way, Woodbury, CT 06798

  A Lovely Renovated End Unit with year round Rhododendron - greenery privacy at the deck. The summer blooms are spectacular! This condo is close to the Woodlake Community Garden, for those wishing to grow your own veggies! Inside you will notice a renovated kitchen with granite countertops, tiled flooring, ceiling fan and stainless steel appliances. The living room and dining room with the

  Terry Lee Adams Adams & Adams Real Estate

  48 Woods Way, Woodbury, CT 06798

Showing Results 41 - 80, Page 2 of 18