Woodbury, CT Homes

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  /24

  $289,000

  $30K PRICE DROP Under Contract

  • 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
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  /7

  $2,100 Per Month

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • House for Rent

  300 Railtree Rd, Woodbury, CT 06798

  1-2 BR one bath completely renovated. Laundry in unit, private off street parking. Plowing and lawn maitenance included tenant shovels walk way. Credit check required no smoking or pets

  Doug Rose Scalzo Real Estate

  300 Railtree 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 $607,181

  Last Listing Agent Matthew Amatruda Drakeley Real Estate, Inc.

  90 Railtree Hill Rd, Woodbury, CT 06798
• 

  Est $1,401,557

  Not Listed For Sale

  17 Gate Post Ln, Woodbury, CT 06798

  • 4 Beds
  • 4.5 Baths
  • 5,694 Sq Ft
  • Built 1998

  17 Gate Post Ln, Woodbury, CT 06798

  Last Sold Summary

  • 48 Days On Market

  Last Listing Agent Russell Antonacci Realtyworx, LLC
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  /26

  $695,000

  Coming Soon

  • 3 Beds
  • 3 Baths
  • 2,970 Sq Ft

  39 Hard Hill Rd, Woodbury, CT 06798

  Turn-key elevated ranch with in-ground pool, and immaculate grounds. Set on 1.6+ park-like acres, this modern ranch includes 3 bed/3 full baths, a 3-season screened porch, and a heated 20x40 pool with an oversized concrete patio. The living areas and recently renovated eat-in chef's kitchen shine with custom island, top-of-the-line appliances, and a dedicated butler's pantry with sink, wine

  Kathryn Bassett William Pitt Sotheby's Int'l

  39 Hard Hill Rd, Woodbury, CT 06798
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  /12

  $2,650 Per Month

  • 3 Beds
  • 1.5 Baths
  • 1,550 Sq Ft
  • Townhouse for Rent

  190 Saw Pit Hill Rd, Woodbury, CT 06798

  Three Bedrooms one full and one half baths in a spacious duplex. Recently painted, updated kitchen and new carpet. Full unfinished basement for extra storage. Landlord requires good credit and employment history. pets considered. year lease and security deposit required

  Sindy Butkus Klemm Real Estate Inc

  190 Saw Pit Hill Rd, Woodbury, CT 06798
• 

  $470,000

  Sold Jun 26, 2026

  5 Kimberly Ln, Woodbury, CT 06798

  • 3 Beds
  • 3 Baths
  • 1,732 Sq Ft
  • Built 1979

  Last Sold Summary

  • $271/SF
  • 63 Days On Market

  Current Estimated Value $469,673

  Last Listing Agent Heather Crabtree RE/MAX RISE

  5 Kimberly Ln, Woodbury, CT 06798
• 

  Est $530,899

  Not Listed For Sale

  990 Washington Rd, Woodbury, CT 06798

  • 4 Beds
  • 2.5 Baths
  • 1,847 Sq Ft
  • Built 2006

  990 Washington Rd, Woodbury, CT 06798

  Last Sold Summary

  • 85 Days On Market

  Last Listing Agent Pam Famiglietti William Raveis Real Estate
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  /40

  $347,500

  $30K PRICE DROP Pending

  • 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
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  /20

  $1,800 Per Month

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

  4-5 Weekeepeemee Rd Unit 5, Woodbury, CT 06798

  Apartment 5 is a large, bright, natural light filled apartment. Second floor with front and back private porches. Living room is very spacious with built ins. Kitchen has granite counters and two pantries. Hard wood flooring. Brand new appliances in laundry room. Freshly painted - Ready for immediate occupancy. This is a second floor unit. Rear yard is recently cleared and seeded for all tenants

  Mary Ann Bennett Drakeley Real Estate, Inc.

  4-5 Weekeepeemee Rd Unit 5, 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 $125,943

  Last Listing Agent Jeff Boucher Drakeley Real Estate, Inc.

  14 Arrowhead Way Unit 6, Woodbury, CT 06798
• 

  Est $909,339

  Not Listed For Sale

  60 Stone Pit Rd, Woodbury, CT 06798

  • 4 Beds
  • 5 Baths
  • 3,583 Sq Ft
  • Built 1999

  60 Stone Pit Rd, Woodbury, CT 06798

  Last Sold Summary

  • 35 Days On Market

  Last Listing Agent Sharon McGuire William Pitt Sotheby's Int'l
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  /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
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  /12

  $2,000 Per Month

  • 2 Beds
  • 1.5 Baths
  • 1,500 Sq Ft
  • Townhouse for Rent

  13 Pleasant St Unit 15, Woodbury, CT 06798

  Spacious two bedroom half duplex located up the street from Canfield Pharmacy.It's antique character features a light filled living room wit wood floors.eatin kitchen and dining toom. half bath on main level as laundry hookups. two bedrooms up and the full bath. Walk up attic for plenty of storage. Tenant must have FICO over 650 with good employment history. Year lease, NO PETS and NO SMOKERS!

  Sindy Butkus Klemm Real Estate Inc

  13 Pleasant St Unit 15, Woodbury, CT 06798
• 

  $513,999

  Sold Jun 25, 2026

  43 Bethwood Ln, Woodbury, CT 06798

  • 3 Beds
  • 2 Baths
  • 1,750 Sq Ft
  • Built 1948

  Last Sold Summary

  • 3% Above List Price
  • $294/SF
  • 49 Days On Market

  Current Estimated Value $496,273

  Last Listing Agent Tim Drakeley Drakeley Real Estate, Inc.

  43 Bethwood Ln, Woodbury, CT 06798
• 

  Est $537,036

  Not Listed For Sale

  325 Cowles Rd, Woodbury, CT 06798

  • 3 Beds
  • 2 Baths
  • 2,190 Sq Ft
  • Built 1947

  325 Cowles Rd, Woodbury, CT 06798

  Last Sold Summary

  • 142 Days On Market

  Last Listing Agent Mary Ann Bennett Drakeley Real Estate, Inc.
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  /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
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  /33

  $3,250 Per Month

  • 2 Beds
  • 2 Baths
  • 2,408 Sq Ft
  • House for Rent

  47 Terrell Rd, Woodbury, CT 06798

  Welcome home to this beautifully updated single-family rental nestled on 14 private acres, offering the perfect blend of comfort, space, and tranquility. This 2-bedroom, 2-bath home features a new spacious bonus room which leads to the brand-new oversized deck overlooking the surrounding natural beauty. The newly finished walk-out lower level will be great for additional flexible living space or

  Wendy Brazauskas Coldwell Banker Realty

  47 Terrell Rd, 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 $239,638

  Not Listed For Sale

  76 Washington Rd Unit 40, Woodbury, CT 06798

  • 2 Beds
  • 1.5 Baths
  • 1,430 Sq Ft
  • Built 1988

  76 Washington Rd Unit 40, Woodbury, CT 06798

  Last Sold Summary

  • 22 Days On Market

  Last Listing Agent Colleen Pickwick eXp Realty
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  /17

  $545,000

  $50K PRICE DROP Pending

  • 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
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  /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
• 

  $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 $543,521

  Last Listing Agent Rhya Szymansky Drakeley Real Estate, Inc.

  667 Upper Grassy Hill Rd, Woodbury, CT 06798
• 

  Est $901,135

  Not Listed For Sale

  62 Whittlesey Rd, Woodbury, CT 06798

  • 4 Beds
  • 2.5 Baths
  • 3,205 Sq Ft
  • Built 2002

  62 Whittlesey Rd, Woodbury, CT 06798

  Last Sold Summary

  • 34 Days On Market

  Last Listing Agent Brianna Carvalho Compass Connecticut, LLC
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  /21

  $600,000

  • 9 Beds
  • 8 Baths
  • 4,492 Sq Ft

  137 & 141 Main St S, Woodbury, CT 06798

  Rare mixed-use investment opportunity on over an acre along Woodbury's desirable Main Street South. This unique property features a seven-unit residential building, a detached garage with an additional apartment above, and a separate commercial building offering approximately 2,000 square feet with its own dedicated entrance and access. Three of the residential units are currently occupied, while

  Taylor O'Keefe Drakeley Real Estate, Inc.

  137 & 141 Main St S, Woodbury, CT 06798
• 

  

  /15

  $1,450 Per Month

  • 1 Bed
  • 1 Bath
  • 484 Sq Ft
  • House for Rent

  35 Mill Rd, Woodbury, CT 06798

  Nestled in a peaceful residential setting with a scenic brook and bridge entry, this cozy ranch-style home offers the perfect blend of rural charm, natural beauty and convenient access to everyday conveniences. Freshly painted with refinished floors, this inviting home features comfortable living space, a kitchen with dining area, one bedroom, home office and a full bathroom with a freestanding

  Lisa McDonald The Brokerage of New England

  35 Mill Rd, 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 $499,743

  Last Listing Agent Tim Drakeley Drakeley Real Estate, Inc.

  242 Bacon Pond 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

  Last Listing Agent Maris LeBlanc William Pitt Sotheby's Int'l
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  /32

  $550,000

  Pending

  • 3 Beds
  • 2 Baths
  • 2,002 Sq Ft

  106 Sprain Brook Rd, Woodbury, CT 06798

  Welcome home to this charming farmhouse setting with privacy and room to grow. The open flat acreage boasts a 2 stall barn with power ready for a hobby farm, or reimagined as a potential pool house, art studio or potential guest quarters. The 3 bedroom 2 full bath home is set overlooking the land and barn with spectacular views from the deck. The long private driveway and peaceful location gives

  Kimberly Peterson BHGRE Gaetano Marra Homes

  106 Sprain Brook Rd, 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
• 

  $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 $181,832

  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

  Last Listing Agent Tom Greto William Raveis Real Estate
• 

  

  /21

  $439,000

  $36K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,032 Sq Ft

  241 Hoop Pole Hill Rd, Woodbury, CT 06798

  Nestled in the highly desirable town of Woodbury, this charming Cape offers just over 2,000 square feet of comfortable living space with endless potential. The home features 3 bedrooms, 2.5 bathrooms, and beautiful hardwood floors throughout. A dedicated home office with custom built-in shelving provides the perfect space for working from home or studying. The inviting living room includes a cozy

  Rhya Szymansky Drakeley Real Estate, Inc.

  241 Hoop Pole Hill Rd, 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 $442,709

  Last Listing Agent Matt Rose Keller Williams Realty

  22 Lake Rd, Woodbury, CT 06798
• 

  Est $820,456

  Not Listed For Sale

  3 Inwood Ln, Woodbury, CT 06798

  • 4 Beds
  • 4 Baths
  • 3,330 Sq Ft
  • Built 1986

  3 Inwood Ln, Woodbury, CT 06798

  Last Sold Summary

  • 58 Days On Market

  Last Listing Agent Elizabeth Newnham William Pitt Sotheby's Int'l
• 

  

  /40

  $259,000

  $16K PRICE DROP 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
• 

  $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 $899,659

  Last Listing Agent Michael Vartolone William Raveis Real Estate

  84 Hurds Hill Rd, Woodbury, CT 06798
• 

  Est $178,554

  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

  Last Listing Agent Anthony Rivera Pro Property Management, LLC
• 

  

  /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
• 

  $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 $1,121,458

  Last Listing Agent John Donato Jr Showcase Realty, Inc.

  5 Blueberry Ln, Woodbury, CT 06798

Showing Results 41 - 80, Page 2 of 18