4,978

Woodbury, CT Homes

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  • 97 Westwood Rd, Woodbury, CT 06798
    97 Westwood Rd, Woodbury, CT 06798
    /2

    $280,000

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

    97 Westwood Rd, Woodbury, CT 06798

    Step back in time and discover the enduring charm of the two bedroom, one bath antique home nestled in the picturesque town of Woodbury. Built in the 1850's this property offers a rare opportunity to own a piece of Litchfield Countie's history- brimming with character, original details and timeless appeal. Being sold in "as is" condition. ***Highest and Best by Friday 7/25 by 6pm***

    Amy Vayan BHGRE Gaetano Marra Homes

    97 Westwood Rd, Woodbury, CT 06798
  • 50 Washington Rd, Woodbury, CT 06798

    $456,000 Sold May 15, 2025

    • 1,550 Sq Ft
    • $294/SF
    • 62 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1895

    50 Washington Rd, Woodbury, CT 06798

    Step back in time with this beautiful Colonial-style home, full of character and charm, nestled in the heart of Woodbury. Built in 1895, this 3-bedroom, 1.5 bathroom property boasts classic colonial architecture with modern updates that make it both timeless and functional. The home features original hardwood floors and large windows that invite plenty of natural light. This spacious living room

    Rhya Szymansky Drakeley Real Estate, Inc.

    50 Washington Rd, Woodbury, CT 06798
  • 60 Pomperaug Rd, Woodbury, CT 06798
    60 Pomperaug Rd, Woodbury, CT 06798
    60 Pomperaug Rd, Woodbury, CT 06798
    /28

    $429,000

    • 4 Beds
    • 2.5 Baths
    • 1,668 Sq Ft

    60 Pomperaug Rd, Woodbury, CT 06798

    NOTE NEW PRICE POINT FOR THIS LOVELY WOODBURY RESIDENCE! TRAVEL OVER THE POMPERAUG RIVER AND WATERFALL TO THIS UNIQUE, ENCHANTING OASIS. Situated close to the center of Woodbury, yet the ambiance of this "country" setting provides the feeling of being miles away from it all! This is a unique opportunity to reside in an historic mill village on one of Woodbury's most picturesque town-maintained

    Terry Lee Adams Adams & Adams Real Estate

    60 Pomperaug Rd, Woodbury, CT 06798
  • 514 Main St N, Woodbury, CT 06798

    $629,000 Sold May 13, 2025

    • 4,800 Sq Ft
    • $131/SF
    • 166 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1870

    514 Main St N, Woodbury, CT 06798

    Your home is your castle! If you've ever dreamed of calling a castle your home, this remarkable 5,000-square-foot stone house is the answer. Known fondly by locals as "The Castle," this property has a fascinating history, with roots tracing back to the 1800s but the all updates including new mechanicals, plumbing, electric, floors, well, septic, roof and more will give you comfort and peace of

    Pam Famiglietti William Raveis Real Estate

    514 Main St N, Woodbury, CT 06798
  • 105 Minortown Rd, Woodbury, CT 06798
    105 Minortown Rd, Woodbury, CT 06798
    105 Minortown Rd, Woodbury, CT 06798
    /35

    $650,000

    • 3 Beds
    • 3 Baths
    • 2,227 Sq Ft

    105 Minortown Rd, Woodbury, CT 06798

    Looking for space? Need a workshop? Collect cars? Need room for the in-laws? This ranch-style home might be the perfect fit! Just minutes from town, the property offers a variety of opportunities. The main level features three bedrooms, two bathrooms, a living room with a gas log fireplace, a formal dining room, and a spacious eat-in kitchen. The partially finished lower level includes a family

    Sindy Butkus Klemm Real Estate Inc

    105 Minortown Rd, Woodbury, CT 06798
  • 44 Woods Way Unit 44, Woodbury, CT 06798

    $290,000 Sold May 09, 2025

    • 1,456 Sq Ft
    • $199/SF
    • 4 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1979

    44 Woods Way Unit 44, Woodbury, CT 06798

    This spacious and sunny end-unit townhouse offers the perfect blend of comfort, convenience, and lifestyle-ideal for first-time buyers in sought after Woodlake community. With 2 bedrooms and 2 Full baths, this home features 1,456 sq ft of living space, plus an additional 855 sq ft of unfinished basement-perfect for hobbyists, a home gym, or extra storage. The updated kitchen includes stainless

    Kristie Perry William Pitt Sotheby's Int'l

    44 Woods Way Unit 44, Woodbury, CT 06798
  • 562 Upper Grassy Hill Rd, Woodbury, CT 06798
    562 Upper Grassy Hill Rd, Woodbury, CT 06798
    562 Upper Grassy Hill Rd, Woodbury, CT 06798
    /40

    $2,495,000

    • 4 Beds
    • 3.5 Baths
    • 6,459 Sq Ft

    562 Upper Grassy Hill Rd, Woodbury, CT 06798

    Shingle style home with horse barn, paddocks & riding arena, set on over 9 acres with a gorgeous westerly view of Roxbury's bucolic rolling hills! This property is an equestrian's dream. Horse barn w 5 stalls w waterers. 2nd level in barn loft for additional space. 6 horse paddocks w waterers & electric fence. Perfectly set riding arena w views. Built in 2013, no expense was spared on the

    John Donato Jr Showcase Realty, Inc.

    562 Upper Grassy Hill Rd, Woodbury, CT 06798
  • 229 Bacon Pond Rd Unit 214, Woodbury, CT 06798

    $175,000 Sold May 02, 2025

    • 913 Sq Ft
    • $192/SF
    • 43 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1971

    229 Bacon Pond Rd Unit 214, Woodbury, CT 06798

    Town In Country is a lovely complex situated in the picturesque town of Woodbury, set back from the road yet close to the center of town, restaurants and shopping. This spacious condo offers 2 bedrooms, 1 full bath with a walk-in tub and a large open living/dining room area. Snuggle up in front of the fireplace during those cold winter months. Enjoy your morning coffee while lounging on your

    Cindy Sevell Coldwell Banker Realty

    229 Bacon Pond Rd Unit 214, Woodbury, CT 06798
  • 130 Grassy Hill Rd, Woodbury, CT 06798
    130 Grassy Hill Rd, Woodbury, CT 06798
    130 Grassy Hill Rd, Woodbury, CT 06798
    /40

    $649,900

    • 3 Beds
    • 2.5 Baths
    • 2,124 Sq Ft

    130 Grassy Hill Rd, Woodbury, CT 06798

    Majestically perched on 2+ private acres, this beautifully maintained three-bedroom Colonial offers seasonal panoramic views of rolling hills and treetops, providing a picturesque year-round backdrop while being close to town. Thoughtfully updated with modern finishes, this home blends comfort and style with ease. Step into the inviting Great Room, where soaring ceilings with exposed beams,

    Wendy Brazauskas Coldwell Banker Realty

    130 Grassy Hill Rd, Woodbury, CT 06798
  • 11 Saxony Ln, Woodbury, CT 06798

    $840,000 Sold May 02, 2025

    • 3,124 Sq Ft
    • $269/SF
    • 84 Days On Market
    • 3 Beds
    • 4 Baths
    • Built 2019

    11 Saxony Ln, Woodbury, CT 06798

    Do not miss this beautiful home set back on a private 4.15-acre lot. Main level features a total open floor plan with vaulted ceilings and half bath. Kitchen features Kucht stainless steel appliances, Quartz countertops, with an oversized walk-in pantry. Extra Large dining, kitchen, family room area with built in sound system perfect for entertaining. Upper level adds 2 large bedrooms along with

    Chris Carey Carey & Guarrera Real Estate

    11 Saxony Ln, Woodbury, CT 06798
  • 467 Weekeepeemee Rd, Woodbury, CT 06798
    467 Weekeepeemee Rd, Woodbury, CT 06798
    467 Weekeepeemee Rd, Woodbury, CT 06798
    /40

    $580,000

    • 4 Beds
    • 2.5 Baths
    • 2,555 Sq Ft

    467 Weekeepeemee Rd, Woodbury, CT 06798

    Experience the true essence of country living in this classic Saltbox Colonial, perfectly situated on 2.5 acres of peaceful, wooded land in picturesque Woodbury. Surrounded by nature's beauty, this home offers a tranquil retreat. Inside, gleaming HW floors flow throughout a timeless layout designed for comfortable living and relaxed entertaining. The spacious eat-in kitchen features a welcoming

    Tammy Powling Coldwell Banker Realty

    467 Weekeepeemee Rd, Woodbury, CT 06798
  • 258 Washington Rd, Woodbury, CT 06798

    $850,000 Sold May 01, 2025

    • 1,628 Sq Ft
    • $522/SF
    • 260 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1850

    258 Washington Rd, Woodbury, CT 06798

    This recently fully renovated Antique has a combination of historic charm & modern amenities, which creates a truly exceptional living space. The potential for a pool adds an extra touch of luxury, while the delightful & well-maintained two-story barn in ready condition, presents exciting opportunities for conversion, whether for a guest house, pool house, or a private office on the 2nd floor

    Pat Lahoud William Pitt Sotheby's Int'l

    258 Washington Rd, Woodbury, CT 06798
  • 14 Arrowhead Way Unit 6, Woodbury, CT 06798
    14 Arrowhead Way Unit 6, Woodbury, CT 06798
    14 Arrowhead Way Unit 6, Woodbury, CT 06798
    /13

    $124,900

    • 1 Bed
    • 1 Bath
    • 546 Sq Ft

    14 Arrowhead Way Unit 6, Woodbury, CT 06798

    Excellent 2nd floor unit. One of only 4 units in the complex that has direct interior access to the Laundry facility. Close to parking and mail. This bright unit has been well maintained and is move in ready. Updates to kitchen and bath with stall shower installed. Don't miss out on this great opportunity. Close to town for shopping, restaurants and recreation.

    Jeff Boucher Drakeley Real Estate, Inc.

    14 Arrowhead Way Unit 6, Woodbury, CT 06798
  • 51 Joshua Hill Rd, Woodbury, CT 06798

    $297,500 Sold Apr 30, 2025

    • 1,508 Sq Ft
    • $197/SF
    • 10 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1960

    51 Joshua Hill Rd, Woodbury, CT 06798

    Endless Potential in Woodbury! Discover the opportunity to own a single-family home in the charming town of Woodbury at an exceptional value. This three-bedroom, one-and-a-half-bathroom ranch is conveniently located near I-84 and Route 6, offering easy access to shopping, dining, and local amenities. While the home could benefit from some updates and TLC, it's a fantastic chance to bring your

    Sarah Perrotti Regency Real Estate, LLC

    51 Joshua Hill Rd, Woodbury, CT 06798
  • 212 Main St N, Woodbury, CT 06798
    212 Main St N, Woodbury, CT 06798
    212 Main St N, Woodbury, CT 06798
    /39

    $585,000

    • 4 Beds
    • 3 Baths
    • 2,861 Sq Ft

    212 Main St N, Woodbury, CT 06798

    Charming antique home in the heart of Woodbury! Set on a spacious, cleared lot, this beautifully maintained property offers a perfect mix of historic character and modern updates. The kitchen features quartz countertops, stainless steel appliances, and ample cabinetry. With three full baths and a large primary suite with walk-in closet and private bath, comfort and convenience abound. Enjoy the

    Heather Crabtree Coldwell Banker Realty

    212 Main St N, Woodbury, CT 06798
  • 35 Fawn Meadow Ln, Woodbury, CT 06798

    $895,000 Sold Apr 29, 2025

    • 2,600 Sq Ft
    • $344/SF
    • 31 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2021

    35 Fawn Meadow Ln, Woodbury, CT 06798

    Located in the heart of Woodbury, the antiques capital of Connecticut, with convenient access to the charming towns of Litchfield, Washington, and Roxbury, this newly built modern farmhouse offers a perfect balance of comfort and elegance. Thoughtfully designed with quality craftsmanship and energy-efficient features, this inviting retreat boasts 3 spacious bedrooms, 3.5 bathrooms, and a

    GREGORY COHEN William Pitt Sotheby's Int'l

    35 Fawn Meadow Ln, Woodbury, CT 06798
  • 84 Hurds Hill Rd, Woodbury, CT 06798
    84 Hurds Hill Rd, Woodbury, CT 06798
    84 Hurds Hill Rd, Woodbury, CT 06798
    /40

    $875,000

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

    84 Hurds Hill Rd, Woodbury, CT 06798

    Welcome to Woodbury! Rebuilt in 1991, this stunning 3,736 sq ft single-family estate sits gracefully on over 11 acres, offering the perfect blend of refined luxury and serene countryside living. Step inside to discover a spacious, light-filled interior designed for both grand entertaining and comfortable everyday living. With four generously sized bedrooms, multiple living areas, and fine

    Michael Vartolone William Raveis Real Estate

    84 Hurds Hill Rd, Woodbury, CT 06798
  • 49 Jacks Bridge Rd, Woodbury, CT 06798

    $628,500 Sold Apr 28, 2025

    • 1,008 Sq Ft
    • $624/SF
    • 228 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1987

    49 Jacks Bridge Rd, Woodbury, CT 06798

    Incredible opportunity at an affordable price! Discover the perfect blend of residential comfort and professional-grade amenities in this exceptional property located in the charming town of Woodbury, nestled in the scenic Litchfield County. This unique offering is ideal for car enthusiasts, hobbyists, or entrepreneurs seeking a versatile space that can serve as both a tranquil home and an

    Christine Green Ardor Real Estate

    49 Jacks Bridge Rd, Woodbury, CT 06798
  • 329 Weekeepeemee Rd, Woodbury, CT 06798
    329 Weekeepeemee Rd, Woodbury, CT 06798
    329 Weekeepeemee Rd, Woodbury, CT 06798
    /36

    $649,000

    • 4 Beds
    • 2.5 Baths
    • 2,506 Sq Ft

    329 Weekeepeemee Rd, Woodbury, CT 06798

    Welcome to your North Woodbury bucolic retreat! Escape from it all, nestled along the banks of the Weekeepeemee River with southern views and sunsets falling over the open fields, Heron fishing only yards from your Adirondack chair and Eagles perched on the nearby trees. Yes, this is Home. This 1780 Colonial has been well cared for, for many decades. The first floor offers a large updated

    Tom Slekis Berkshire Hathaway NE Prop.

    329 Weekeepeemee Rd, Woodbury, CT 06798
  • 42 Woods Way Unit 126F, Woodbury, CT 06798

    $330,000 Sold Apr 23, 2025

    • 1,640 Sq Ft
    • $201/SF
    • 21 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1980

    42 Woods Way Unit 126F, Woodbury, CT 06798

    Woodlake in Woodbury an easy place to live in a great community. This three bedroom two full and one-half bath was built in 1980 and is ready for a new homeowner. End unit with plenty of light and a beautiful deck. The flooring is a combination of tile and carpet, and the floor plan is open and airy. The kitchen is a great size for a little coffee table, stainless appliances, white cabinets and

    Bonnie Wilson Berkshire Hathaway NE Prop.

    42 Woods Way Unit 126F, Woodbury, CT 06798
  • 39 Quanopaug Trail, Woodbury, CT 06798
    39 Quanopaug Trail, Woodbury, CT 06798
    39 Quanopaug Trail, Woodbury, CT 06798
    /40

    $1,950,000

    • 5 Beds
    • 6 Baths
    • 7,413 Sq Ft

    39 Quanopaug Trail, Woodbury, CT 06798

    Exceptionally constructed contemporary set on almost 9 acres with a beautiful view of distant hilltops. Both the house and the outdoor spaces are truly impressive, perfect for entertaining and nature lovers. With over 7,500 sq ft, the home is spacious with exposed beams, an abundance of windows and many updates & upgrades. The public rooms are open and airy encompassing the kitchen, dining and

    Maria Taylor Klemm Real Estate Inc

    39 Quanopaug Trail, Woodbury, CT 06798
  • 5 Bear Run, Woodbury, CT 06798

    $952,000 Sold Apr 15, 2025

    • 5,915 Sq Ft
    • $161/SF
    • 132 Days On Market
    • 4 Beds
    • 4.5 Baths
    • Built 1997

    5 Bear Run, Woodbury, CT 06798

    Tucked away on a sought-after cul-de-sac, this open-layout home is crafted for exceptional entertaining. The light-filled, two-story foyer is framed by two sets of French doors: one opening to an office & the other leading to a living room that flows seamlessly into the dining room-an ideal setup for holiday gatherings. The custom kitchen, equipped with granite countertops, a center island, gas

    Shelley Drakeley Drakeley Real Estate, Inc.

    5 Bear Run, Woodbury, CT 06798
  • 0 Cowles Rd, Woodbury, CT 06798
    0 Cowles Rd, Woodbury, CT 06798
    0 Cowles Rd, Woodbury, CT 06798
    /13

    $675,000

    • 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
  • 29 Fawn Meadow Ln, Woodbury, CT 06798

    $735,000 Sold Apr 14, 2025

    • 2,042 Sq Ft
    • $360/SF
    • 45 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2022

    29 Fawn Meadow Ln, Woodbury, CT 06798

    Nestled in the heart of Woodbury, with easy access to the picturesque towns of Litchfield, Washington, and Roxbury, this newly constructed modern farmhouse-style home offers the perfect blend of comfort, privacy, and New England charm. Built with quality craftsmanship and energy-efficient features, this serene retreat boasts 3 spacious bedrooms, 2.5 bathrooms, plus a versatile 300+/- sq. ft.

    GREGORY COHEN William Pitt Sotheby's Int'l

    29 Fawn Meadow Ln, Woodbury, CT 06798
  • 439 Washington Rd, Woodbury, CT 06798
    439 Washington Rd, Woodbury, CT 06798
    439 Washington Rd, Woodbury, CT 06798
    /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
  • 17 Tamarack Ln Unit 17, Woodbury, CT 06798

    $291,000 Sold Apr 11, 2025

    • 1,300 Sq Ft
    • $224/SF
    • 22 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1974

    17 Tamarack Ln Unit 17, Woodbury, CT 06798

    Beautifully updated and cared for Ranch style end unit condo located at the end of Tamarack Lane overlooking a peaceful wooded landscape. Open floor plan with dining area and a vaulted family room that features a newer wood stove fireplace insert with gorgeous custom mantle with sliders to an updated Trex deck. Ceramic tile and hardwood floors grace the main level of this freshly painted home.

    Sharisse Steiner William Raveis Real Estate

    17 Tamarack Ln Unit 17, Woodbury, CT 06798
  • 373 Transylvania Rd, Woodbury, CT 06798
    373 Transylvania Rd, Woodbury, CT 06798
    373 Transylvania Rd, Woodbury, CT 06798
    /40

    $1,275,000

    • 3 Beds
    • 5 Baths
    • 4,059 Sq Ft

    373 Transylvania Rd, Woodbury, CT 06798

    Custom-built. This unique home is made for entertaining. 4000 ft.2 home with 3 bedroom suites each containing its own full bath. 5 Bathrooms. 3 Fireplaces. Chef's kitchen with granite counters, double ovens, bow window w/bench seat & walk out to deck. Formal dining room has tray ceiling. Great room with fireplace and full bar. Den/library has fireplace. Bright piano room/sunroom/office also walks

    Beatriz Conroy William Raveis Real Estate

    373 Transylvania Rd, Woodbury, CT 06798

Showing Results 81 - 120, Page 3 of 18

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