Woodbury, CT Homes

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  $199,900 Under Contract

  • 2 Beds
  • 1.5 Baths
  • 1,054 Sq Ft

  5 Upper Commons, Woodbury, CT 06798

  Charming 2-story condo that balances everyday convenience w/ a comfortable, easy-to-live-in layout. Located in Arlingtowne, just a short walk from Fancyburg Park, the Scioto River, & Griggs Park & Dam. Step inside to find wood floors throughout. The spacious living room is designed for both relaxing & entertaining, w/ sliding glass doors that lead to a private, fenced patio, convenient storage

  

  Steve Smith

  Keller Williams Consultants

  (380) 246-7134

  5 Upper Commons, Woodbury, CT 06798
• Explore Woodbury

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  /31

  $3,750 total monthly price

  • 2 Beds
  • 2 Baths
  • 1,968 Sq Ft
  • House for Rent

  33 Washington Ave, Woodbury, CT 06798

  AVAILABLE FOR $3,950/MONTH. Stunning over-sized Cape on serene, park-like grounds adjacent to a nature preserve. Fully furnished, this inviting 2 bedroom home has been lovingly renovated with a great eye for detail. Quiet street centrally located in historic Woodbury. Newly finished hardwood oak flooring throughout. Two full bathrooms. The large living room with fireplace also includes a bright

  

  Rebecca Doh

  W. Raveis Lifestyles Realty

  (203) 872-6274

  33 Washington Ave, Woodbury, CT 06798
• 

  $897,000 Sold Jun 27, 2025

  332 Good Hill Rd, Woodbury, CT 06798

  • 3 Beds
  • 3 Baths
  • 2,894 Sq Ft
  • Built 2015

  Last Sold Summary

  • 12% Above List Price
  • $310/SF
  • 27 Days On Market

  Current Estimated Value $926,421

  Last Listing Agent Rebecca Doh W. Raveis Lifestyles Realty

  332 Good Hill Rd, Woodbury, CT 06798
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  Est $418,070 Not Listed For Sale

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

  220 Upper Grassy Hill Rd, Woodbury, CT 06798

  220 Upper Grassy Hill Rd, Woodbury, CT 06798
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  /40

  $899,900

  • 4 Beds
  • 2.5 Baths
  • 3,700 Sq Ft

  337 Main St S, Woodbury, CT 06798

  A Real Classic! Beautifully renovated with many original features. Located in the Historic District in the heart of Woodbury. Stroll along Main Street to parks, excellent restaurants, house of worship, conveniences and antique shops. Home is just lovely with exposed beams, wide board hardwood floors, 4 fireplaces, outside on the patio, primary bedroom, dining room and living room. One fireplace

  

  Marian Van Egas

  Berkshire Hathaway NE Prop.

  (475) 255-3184

  337 Main St S, Woodbury, CT 06798
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  /35

  $1,550 - $1,899 per month plus fees

  Woodbury Knoll

  Studio - 2 Beds

  302 Tuttle Rd, Woodbury, CT 06798

  Welcome to Woodbury Knoll Apartments, where modern comfort meets tranquil, lakeside living. Life unfolds at a different pace here mornings are inspired by natures quiet beauty, and evenings unwind in serene surroundings. In our Woodbury, CT apartments, you'll discover a lifestyle thats vibrant yet peaceful, perfectly balanced, and endlessly welcoming.

  302 Tuttle Rd, Woodbury, CT 06798
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  $1,700,000 Sold Jan 20, 2026

  225 Old Sherman Hill Rd, Woodbury, CT 06798

  • 4 Beds
  • 4.5 Baths
  • 4,517 Sq Ft
  • Built 1969

  Last Sold Summary

  • 19% Below List Price
  • $376/SF
  • 345 Days On Market

  Last Listing Agent Maria Taylor Klemm Real Estate Inc

  225 Old Sherman Hill Rd, Woodbury, CT 06798
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  Est $293,031 Not Listed For Sale

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

  1 Hickory Ln Unit 1, Woodbury, CT 06798

  1 Hickory Ln Unit 1, Woodbury, CT 06798
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  $179,900 Under Contract

  • Land
  • 3.63 Acres
  • $49,559 per Acre

  0 Minortown Rd, Woodbury, CT 06798

  Build your dream home on this 3.63-acre parcel on scenic Minortown Road in Woodbury, where the standout feature is a wide-open meadow with room to farm. Backing up to acres of protected open space, the setting feels expansive, private, and quintessentially rural-yet you're still just minutes from town amenities, shopping, and dining. With generous acreage for gardens, animals, and outdoor living

  

  Tim Drakeley

  Drakeley Real Estate, Inc.

  (475) 447-1880

  0 Minortown Rd, Woodbury, CT 06798
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  /6

  $1,200 total monthly price

  • 1 Bath
  • 4,066 Sq Ft
  • Apartment for Rent

  1633 Main St N, Woodbury, CT 06798

  Sunny bright studio apartment with hardwood floor.Owner related to the agent.

  Pradip Khanal US Realty Group LLC

  1633 Main St N, Woodbury, CT 06798
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  $375,000 Sold Feb 14, 2025

  22 Clubhouse Dr Unit 22, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 1,888 Sq Ft
  • Built 1972

  Last Sold Summary

  • 12% Below List Price
  • $199/SF
  • 154 Days On Market

  Current Estimated Value $403,181

  Last Listing Agent Sindy Butkus Klemm Real Estate Inc

  22 Clubhouse Dr Unit 22, Woodbury, CT 06798
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  Est $690,077 Not Listed For Sale

  • 3 Beds
  • 6 Baths
  • 8,747 Sq Ft

  785 Washington Rd, Woodbury, CT 06798

  785 Washington Rd, Woodbury, CT 06798
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  $1,100,000

  • 3 Beds
  • 2.5 Baths
  • 2,042 Sq Ft

  27 Middle Quarter Rd, Woodbury, CT 06798

  Discover the charm of this beautiful antique home in the heart of Woodbury! Nestled on the serene Middle Quarter Road, this vintage gem is being restored by the current owner and is just a 2-minute stroll from coffee shops, top-notch restaurants, and the historic Main Street. The home will be meticulously updated from the ground up, featuring wide board antique flooring, a stunning great room

  

  Tim Drakeley

  Drakeley Real Estate, Inc.

  (203) 457-8490

  27 Middle Quarter Rd, Woodbury, CT 06798
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  /20

  $4,950 total monthly price

  • 4 Beds
  • 4.5 Baths
  • 7,112 Sq Ft
  • House for Rent

  259 Main St S, Woodbury, CT 06798

  Property Id: 1500786Located on Main Street South in the heart of Woodbury, in the Litchfield Hills this main house offers 4 BR, 4.5 baths and features original architectural elements, ample living space and beautiful outdoor space. The main living area has a half bath, EIK with island, SS appliances and door to side deck for outdoor eating and grilling + private courtyard, professionally

  259 Main St S, Woodbury, CT 06798
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  $480,000 Sold Nov 04, 2025

  145 Cat Swamp Rd, Woodbury, CT 06798

  • 3 Beds
  • 1.5 Baths
  • 1,792 Sq Ft
  • Built 1961

  Last Sold Summary

  • 4% Above List Price
  • $268/SF
  • 51 Days On Market

  Current Estimated Value $484,620

  Last Listing Agent Nancy Langrock William Raveis Real Estate

  145 Cat Swamp Rd, Woodbury, CT 06798
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  Not Listed For Sale

  0 Mill Rd, Woodbury, CT 06798

  0 Mill Rd, Woodbury, CT 06798
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  /15

  $990,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,300 Sq Ft

  523 Main St N, Woodbury, CT 06798

  To be built Modern style home with gorgeous southern views and privacy from your neighbors. Enjoy the wall of glass overlooking a bluestone patio, and beautiful views above Main Street North! Just a few minutes from Woodbury's town center, this home provides an open floor with a kitchen/great room, a cathedral ceiling, and a floor-to-ceiling masonry fireplace. The first floor includes a primary

  

  Tim Drakeley

  Drakeley Real Estate, Inc.

  (475) 284-8768

  523 Main St N, Woodbury, CT 06798
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  /10

  $1,750 total monthly price

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

  47A Quassuk Rd, Woodbury, CT 06798

  Well maintained stand alone cottage near the heart of Woodbury. Freshly painted, updated fixtures & flooring, & newer mini split for heat & A/C. Serene & private grounds with a rear patio overlooking the landscape. Owners reside in the main house & will plow & maintain the lawn. Tenant to remove the snow on his/her walkway to entry. Tenant responsible for electric, cable and/or wifi. Absolutely

  Gina Jacobs Gina Jacobs Real Estate

  47A Quassuk Rd, Woodbury, CT 06798
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  $430,000 Sold Apr 04, 2025

  163 Washington Rd, Woodbury, CT 06798

  • 4 Beds
  • 3 Baths
  • 2,521 Sq Ft
  • Built 1836

  Last Sold Summary

  • 5% Below List Price
  • $171/SF
  • 162 Days On Market

  Current Estimated Value $454,499

  Last Listing Agent Katherine Parlato Drakeley Real Estate, Inc.

  163 Washington Rd, Woodbury, CT 06798
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  Est $1,327,855 Not Listed For Sale

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

  17 Gate Post Ln, Woodbury, CT 06798

  17 Gate Post Ln, Woodbury, CT 06798
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  /40

  $1,100,000

  • 4 Beds
  • 2.5 Baths
  • 3,545 Sq Ft

  45 N Gate Rd, Woodbury, CT 06798

  Welcome to Woodbury, a quintessential New England town. This house is located in a very desirable neighborhood, just north of the town center. An inviting covered front porch will greet you. This leads to a 2 story foyer and an open floor plan opens up in front of you! To the left is a formal LR/Den. (cozy up with a good book) To the right is formal Dining Room with a trey ceiling, seats 8-10

  Jeff Colt Showcase Realty, Inc.

  45 N Gate Rd, Woodbury, CT 06798
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  /37

  $30,000 total monthly price

  • 3 Beds
  • 2.5 Baths
  • 3,282 Sq Ft
  • House for Rent

  28 Leavenworth Rd, Woodbury, CT 06798

  STUNNING MEMORIAL DAY - LABOR DAY RENTAL with POOL and TENNIS COURT (with lights). Enjoy a month or all summer at this resort-style escape with newly renovated interior and incredible entertaining space indoors and out. Extraordinary cook's kitchen with breakfast nook opens into an expansive sun-filled room overlooking lawns, tennis court and pool. Updated bedrooms and bathrooms provide a

  Diana Bisselle William Pitt Sotheby's Int'l

  28 Leavenworth Rd, Woodbury, CT 06798
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  $424,950 Sold Oct 23, 2025

  158 Hazel Plain Rd, Woodbury, CT 06798

  • 4 Beds
  • 2.5 Baths
  • 2,085 Sq Ft
  • Built 1974

  Last Sold Summary

  • $204/SF
  • 32 Days On Market

  Current Estimated Value $437,456

  Last Listing Agent Michael Ferris eXp Realty

  158 Hazel Plain Rd, Woodbury, CT 06798
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  Est $521,300 Not Listed For Sale

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

  990 Washington Rd, Woodbury, CT 06798

  990 Washington Rd, Woodbury, CT 06798
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  /25

  $279,990 Open Sat 1PM - 3PM

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

  4 Fox Run Unit 4, Woodbury, CT 06798

  Welcome to this beautifully refreshed townhome in the highly desirable Woodlake Condominium Complex in Woodbury. Freshly painted throughout and filled with natural light, the main level features hardwood floors, a spacious living and dining area with a cozy fireplace, and a sliding door that opens to a private deck overlooking peaceful wooded surroundings. The updated kitchen includes granite

  Henrik K Kjaer Keller Williams Realty

  4 Fox Run Unit 4, Woodbury, CT 06798
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  /34

  $8,000 total monthly price

  • 2 Beds
  • 2 Baths
  • 1,197 Sq Ft
  • House for Rent

  112 W Lake Rd Unit 112, Woodbury, CT 06798

  Year round lake living! Swim, canoe, kayak, fish, hike and unwind on your own beach, located on speed restricted Lake Quassapaug in Middlebury, CT. This cottage was completely renovated in 2020 by a local designer. It includes two bedrooms, two full bathrooms, laundry facilities, a Chef's kitchen equipped with a commercial Wolf oven and range, a Sub-Zero refrigerator, and a breakfast bar. Newly

  Sindy Butkus Klemm Real Estate Inc

  112 W Lake Rd Unit 112, Woodbury, CT 06798
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  $660,000 Sold Feb 05, 2026

  38 Barnhill Rd, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 2,835 Sq Ft
  • Built 1986

  Last Sold Summary

  • 5% Below List Price
  • $233/SF
  • 134 Days On Market

  Last Listing Agent Donna Bannon BHGRE Gaetano Marra Homes

  38 Barnhill Rd, Woodbury, CT 06798
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  Est $920,707 Not Listed For Sale

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

  60 Stone Pit Rd, Woodbury, CT 06798

  60 Stone Pit Rd, Woodbury, CT 06798
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  /40

  $649,900 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,264 Sq Ft

  13 Park Ln, Woodbury, CT 06798

  Set on a picturesque lot with mature landscaping and gorgeous outdoor spaces, this beautifully maintained home offers a flexible layout designed for both entertaining and everyday living. The front entry opens to a bright and inviting living room with built-ins and gas fireplace. The kitchen blends style and function with granite countertops, stainless appliances, and a natural flow into the

  Michael Wright RE/MAX Right Choice

  13 Park Ln, Woodbury, CT 06798
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  /17

  $9,500 total monthly price

  • 2 Beds
  • 2 Baths
  • 1,197 Sq Ft
  • House for Rent

  112 W Lake Rd Unit D4, Woodbury, CT 06798

  Relaxing summer rental! Swim, Fish, hike and unwind on your own beach. Located on speed restricted Lake Quassapaug in Middlebury, CT. This cottage was completely renovated in 2020 by a local designer. It includes two bedrooms, two full bathrooms, laundry facilities, a Chef's kitchen equipped with a commercial Wolf oven and range, a Sub-Zero refrigerator, and a breakfast bar. Newly installed

  Sindy Butkus Klemm Real Estate Inc

  112 W Lake Rd Unit D4, Woodbury, CT 06798
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  $350,000 Sold Aug 08, 2025

  306 Upper Grassy Hill Rd, Woodbury, CT 06798

  • 3 Beds
  • 2 Baths
  • 1,936 Sq Ft
  • Built 1964

  Last Sold Summary

  • $181/SF
  • 6 Days On Market

  Current Estimated Value $372,949

  Last Listing Agent Shawna Mucherino Coldwell Banker Realty

  306 Upper Grassy Hill Rd, Woodbury, CT 06798
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  Est $535,097 Not Listed For Sale

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

  325 Cowles Rd, Woodbury, CT 06798

  325 Cowles Rd, Woodbury, CT 06798
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  /16

  $849,000

  • 3 Beds
  • 4 Baths
  • 3,082 Sq Ft

  148 Flanders Rd, Woodbury, CT 06798

  Country Living Abounds with this unique custom built one of a kind Cape nestled on 5 secluded acres. This home features an open floor plan with post and beam construction, beamed ceilings, oak floors, Plaster Walls, fully applianced Kitchen with breakfast bar, a spacious Family Room with brick fireplace, built-ins, & slider leading to back deck. The Living Room with fireplace is adjacent to a

  Ron Nettleton William Raveis Real Estate

  148 Flanders Rd, Woodbury, CT 06798
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  /21

  $3,000 total monthly price

  • 1 Bed
  • 1 Bath
  • 1,312 Sq Ft
  • House for Rent

  235 White Deer Rocks Rd Unit Guest House, Woodbury, CT 06798

  This completely remodeled guest cottage offers the perfect retreat for weekend getaways or full-time living. The home comes fully furnished with couch, dining table, and king-size bed, while the kitchen features brand-new appliances and a conveniently located washer/dryer upstairs. The heart of the home is the great room living area with large center island-ideal for working from home or

  Christian Jensen William Pitt Sotheby's Int'l

  235 White Deer Rocks Rd Unit Guest House, Woodbury, CT 06798
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  $445,000 Sold Mar 03, 2025

  397 Railtree Hill Rd, Woodbury, CT 06798

  • 3 Beds
  • 2 Baths
  • 1,444 Sq Ft
  • Built 1978

  Last Sold Summary

  • 1% Below List Price
  • $308/SF
  • 41 Days On Market

  Current Estimated Value $477,468

  Last Listing Agent Tim Drakeley Drakeley Real Estate, Inc.

  397 Railtree Hill Rd, Woodbury, CT 06798
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  Est $274,490 Not Listed For Sale

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

  76 Washington Rd Unit 40, Woodbury, CT 06798

  76 Washington Rd Unit 40, Woodbury, CT 06798
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  /31

  $895,000 Under Contract

  • 4 Beds
  • 2.5 Baths
  • 3,776 Sq Ft

  52 Steeple View Ln, Woodbury, CT 06798

  Nestled within an established enclave of Woodbury-a quintessential New England town-this 2001 four-bedroom Colonial offers a refined blend of understated, classic architecture, and modern comfort. Ideally located just five minutes from Main Street, the home is privately sited at the end of a quiet cul-de-sac, bordered by tranquil woodlands. The interior showcases richly layered trim details,

  Beverly Mosch William Pitt Sotheby's Int'l

  52 Steeple View Ln, Woodbury, CT 06798
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  $765,000 Sold Jul 29, 2025

  3 Inwood Ln, Woodbury, CT 06798

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

  Last Sold Summary

  • 13% Below List Price
  • $230/SF
  • 58 Days On Market

  Current Estimated Value $796,100

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

  3 Inwood Ln, Woodbury, CT 06798
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  Not Listed For Sale

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

  267 Good Hill Rd, Woodbury, CT 06798

  267 Good Hill Rd, Woodbury, CT 06798
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  /21

  $749,900 Pending

  • 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

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