Woodbury Homes for Sale

Welcome to Woodbury, Connecticut – a hidden gem nestled in the heart of Litchfield County. Known for its picturesque landscapes, charming New England architecture, and a strong sense of community, Woodbury offers a unique blend of rural charm and modern convenience. With its rich history, vibrant arts scene, and abundant outdoor recreational opportunities, it’s no wonder that many are choosing to call this delightful town home.

Woodbury is celebrated for its historic downtown area, where you can stroll along tree-lined streets, explore quaint boutiques, and enjoy local eateries that serve everything from farm-fresh fare to artisanal coffee. The town is also home to various parks and nature reserves, perfect for hiking, biking, and enjoying the stunning scenery that Connecticut is known for.

For those looking to make Woodbury their home, the real estate market offers an impressive array of homes for sale. From charming colonial-style houses to modern, spacious family homes, there’s something to suit every taste and lifestyle. Many properties boast expansive yards, ideal for family gatherings and outdoor activities, while others feature beautiful views of the surrounding hills and valleys.

With a strong emphasis on community and a commitment to preserving its natural beauty, Woodbury is more than just a place to live; it’s a place to thrive. Whether you’re a first-time homebuyer or looking to settle down in a peaceful environment, Woodbury has the perfect home waiting for you. Discover the charm and warmth of this lovely town – your dream home in Woodbury is just a click away!

Newest Woodbury Homes for Sale

$359,900

2 Beds ⋅ 1 Baths ⋅ 24218073 MLS

Great Ranch well sited on level almost half acre yard, large living room with fireplace, kitchen and dining room overlooking back yard and deck, 2 bedrooms and 1 full bath, oversized back deck overlooking a small seasonal brook, private PHOTOS next week

555 Middle Road Tpke, Woodbury

$595,000

3 Beds ⋅ 3 Baths ⋅ 24217173 MLS

Step into timeless charm with this classic 1800 New England Colonial in historic Woodbury. Thoughtfully curated wallcoverings weave subtle, boutique elegance and modern personality throughout. The main level offers a bright kitchen with under-cabinet lighting and tiled backsplash, plus space to eat in or host just steps away in the formal dining room. Conveniently situated in the kitchen is a stylishly remodeled half bath featuring marble tile floors. Unwind in the large living room complete with fireplace and built-in bookshelves, or retreat to the freshly remodeled den or home office perfectly positioned off the living and dining rooms. A cozy screened-in porch completes the level. The second floor hosts three bedrooms and two full bathrooms, highlighted by an available ensuite primary retreat. Above, a fully finished, heated third-floor attic offers versatile bonus space with hardwood floors-ideal for a dedicated workout room, play room, or guest suite. Head to the attached two-car garage through a sunlit mudroom, which opens directly to the private back patio and flat, fenced-in backyard. Enjoy unbeatable village convenience with town sidewalk access leading directly to grocery stores, the post office, great restaurants, and the library. A perfect blend of antique character and modern everyday living.

36 Main St S, Woodbury

$375,000

3 Beds ⋅ 1 Baths ⋅ 24215409 MLS

Looking for the ease of one level living, a beautiful backyard, and the peace of mind that comes with major updates already completed? This Woodbury ranch checks all the boxes! Nestled along a quiet, country road, this meticulously maintained 3 bedroom ranch offers the perfect blend of comfort, convenience, and a picturesque setting. Pride of ownership shines throughout, featuring hardwood flooring, a bright and inviting interior, a spacious kitchen with white cabinetry and stainless steel appliances along with access to a newer deck, perfect for outdoor dining, entertaining, or enjoying your morning coffee. The expansive, backyard features mature trees, perennial gardens, & professionally landscaped grounds. A 1 car garage with attic storage and 3 additional sheds on the property offer plenty of space for tools, equipment, and seasonal items. Enjoy peace of mind with significant improvements including a BRAND NEW septic system, newer heating and cooling systems, roof, and water filtration system. Lovingly cared for and thoughtfully updated, this Woodbury home is ready for it's next chapter!

36 Atwood Rd, Woodbury

$649,900

4 Beds ⋅ 4 Baths ⋅ 24213335 MLS

Welcome to this stunning, fully remodeled Colonial in Woodbury, located in beautiful Litchfield County! Situated on over 2 acres with a private pond, this home features 4 bedrooms, 2 full baths, 2 half baths, a fully remodeled basement, central air, and a 2-car garage with low taxes! Some of the recent updates include a new roof, windows, doors, and mechanicals. Enjoy peaceful pond views from the screened-in porch. This exceptional property is waiting for its new owner!

67 Flanders Rd, Woodbury

$529,000

3 Beds ⋅ 2 Baths ⋅ 24210084 MLS

Looking for a convenient in town location? Built in 1940, this delightful vintage colonial is loaded with the charm of the 1940's. The front to back living room offers a fireplace, built ins as well as oak flooring. It also features a French door to the rear porch overlooking the spacious rear yard. Located adjacent to the kitchen, the formal dining room features a built-in china closet and oak flooring. A powder room and laundry area complete the main level. Upstairs, a front to back primary bedroom with oak flooring. There are two bedrooms and a full bath on this level. Need more room? The walk-up attic is floored provides the opportunity for future expansion. There is a rec room on the lower level for additional space.

11 Judson Ave, Woodbury

$699,900

3 Beds ⋅ 2 Baths ⋅ 24211238 MLS

Completely renovated and move-in ready, this three-bedroom ranch in North Woodbury has been gutted to the studs and beautifully rebuilt throughout. The open-concept layout features a gorgeous new kitchen with center island opening to a spacious family and dining area with plenty of room for larger gatherings. No detail was overlooked in the renovation. All three bedrooms feature hardwood floors, while the home also offers a new full bath, new laundry room, and a private side deck just off the entry. The finished lower level provides valuable additional living space for a family room, home office, exercise area, or recreation room. A rare opportunity to own a like-new ranch-style home in Woodbury with nothing left to do but move in and enjoy.

1217 Main St N, Woodbury

$1,149,000

3 Beds ⋅ 3 Baths ⋅ 24209744 MLS

Private Litchfield County Retreat on Nearly 10 Acres Tucked among the picturesque hills of Litchfield County, along the desirable Woodbury/Roxbury line, this distinctive Colonial-Contemporary residence offers an exceptional combination of privacy, natural beauty, and modern comfort on nearly 10 acres. Surrounded by mature trees, lush landscaping, and vibrant plantings, the property enjoys a peaceful, secluded setting with the gentle sounds of Transylvania Brook flowing just beyond the backyard. A long, paved, beautifully illuminated driveway leads to the home, where an impressive double-door entrance welcomes you into a spacious foyer featuring a unique indoor water feature. The thoughtfully designed interior offers three generously sized bedrooms, two-and-a-half beautifully renovated bathrooms with luxurious Italian marble tile, and recessed lighting throughout. The inviting lower-level family room opens through French doors to an expansive stone patio and a heated, inground Gunite swimming pool, creating an ideal setting for relaxing or entertaining. A bright four-season sunroom captures sweeping views of the surrounding landscape, while a dedicated office provides a comfortable and private work-from-home space. The spacious primary suite is a true retreat, featuring a walk-in closet, Jacuzzi tub, private balcony overlooking the pool, and a versatile bonus room that can be customized as a reading room, home gym, nursery, or additional living space. Additional fe

24 Roxbury Rd, Woodbury

$2,149,900

5 Beds ⋅ 5 Baths ⋅ 24209591 MLS

Set well back from Weekeepeemee Road in one of Woodbury's finest locations, this exceptionally well-built Colonial offers approximately 5,900 square feet of thoughtfully designed living space. Multiple bedroom suites and an open floor plan provide room for everyone, with inviting spaces for both everyday living and entertaining. The beautiful kitchen opens to a covered porch overlooking an expansive patio and gunite pool, creating a seamless connection between indoor and outdoor gatherings. Car enthusiasts will appreciate the remarkable garage and barn space. An attached, heated three-car garage is complemented by a lower-level garage with room for several additional vehicles. An impressive detached barn, constructed with steel and concrete, accommodates another six to eight cars and features heat, a half bath, glass garage doors, and both upper- and lower-level access. Outside, meticulous landscaping and a paved driveway enhance the setting, while a spacious front patio provides the perfect spot to enjoy the sunsets. An open meadow offers room for outdoor celebrations or potential equestrian use. With its generous living spaces, exceptional vehicle storage, and beautifully maintained grounds, this distinctive property offers far more than the ordinary.

348 Weekeepeemee Rd, Woodbury

$950,000

6 Beds ⋅ 4 Baths ⋅ 24209295 MLS

A private retreat with Million dollar views! Nestled at the end of a peaceful cul-de-sac, this 3800+ Colonial offers a rare combination of privacy, space, and breathtaking views. Set against a backdrop of rolling hills, with gorgeous sunsets - where every season brings a beautiful new view. Step inside and you'll be greeted by expansive LR/Great RM featuring soaring cathedral ceilings, freshly painted walls, and an abundance of natural light. Kitchen is appointed with granite countertops, SS appliances, double pantries, double sinks and a wine chiller making it functional and inviting. Rich Brazilian Cherry HW floors add warmth and elegance throughout the first floor. The first floor primary suite offers a peaceful retreat of its own, highlighted by a claw-foot soaking tub to relax while taking in the views. Upstairs, three additional bedrooms, along with a renovated full bathroom featuring marble walk-in shower and marble countertops. A cozy area(den) for family time and dedicated office space. Lets not forget the bonus living space above the garage. This separate entrance living space includes two-bedroom, kitchen, LR, laundry and garage space. The possibilities for extended family, guests, au pair, rental income or Airbnb option are endless.

92 Quail Run Rd, Woodbury

$875,000

3 Beds ⋅ 3 Baths ⋅ 24209527 MLS

Welcome to history, charm, and an incredible location-the best of both worlds! Tucked along a quiet side road, this lovingly cared-for antique offers a peaceful, private setting with a picturesque waterfall nearby, yet is within walking distance to an amazing collection of local favorites, including fine restaurants, diners, a brewery, pub with live entertainment, and French bakery. No wonder they call it "Food-bury!" A stone path leads to a beautiful stone landing and a home filled with warmth and character. The spacious L-shaped living room offers two inviting gathering areas-one centered around a wood-burning fireplace with room for a grand piano, and the other warmed by a woodstove beside a full-wall library and second seating area. Just beyond is a sun-filled, beamed room wrapped in windows on three sides, perfect for breakfast, reading, art, TV, or simply enjoying the view. The charming country kitchen is exceptionally appointed with premium Viking, Miele, Sub-Zero, Dacor and Fisher & Paykel appliances, including an induction cooktop, wall and speed ovens, warming drawer and 2-drawer dishwasher. Thoughtful details include Waterworks fixtures, a pot filler, custom pull-out cabinetry and under-cabinet lighting. Two staircases lead to three restful bedrooms and two beautifully renovated full baths. The primary bath features a Waterworks vanity with quartz top and Waterworks hardware, while the second bath creates a spa-like retreat with a soaking tub and steam shower.

2 Pomperaug Rd, Woodbury

$849,900

4 Beds ⋅ 2 Baths ⋅ 24208978 MLS

Reader's Digest named Woodbury the "Most Charming Small Town in Connecticut" in 2024 and received the same recognition in 2020 and 2018.That fits this home perfectly. 63 Main St N is an 1850 antique home with a 2002 addition, offering 4 bedrooms, 2 updated bathrooms and 2,662 square feet of delight on 0.36 acres. It has the historic character people expect from Main Street - mahogany-floored wrap-around porch, oak floors, built-ins and fireplaces - while also having an open kitchen/dining/family-room layout, gas log fireplace, first-floor bedroom, updated bath and attached garage. The backyard should be another major focus. It has beautiful stone walls, an outdoor fireplace, new 43" outdoor gas grill, hot tub, irrigation system and a completely flat yard with room for entertaining and potentially a future pool.

63 Main St N, Woodbury

$550,000

3 Beds ⋅ 2 Baths ⋅ 24206868 MLS

Charming Brick Ranch on 2+ Acres Nestled on more than two acres in a peaceful setting, this well-built brick ranch offers the perfect blend of privacy, comfort, and convenience, with easy access to shopping, dining, and everyday amenities. The home has been freshly painted, meticulously maintained, and reflects pride of ownership throughout. Inside, you'll find a spacious and inviting floor plan featuring hardwood flooring in the living room and all three bedrooms, adding warmth and character to the main living spaces. The kitchen and pantry are finished with durable vinyl flooring, providing easy care and everyday practicality. The generously sized kitchen features ample counter space, a pantry, a cozy eating area, and a gas fireplace, making it an ideal gathering place for family and friends. The living room is enhanced by built-in bookcases, while the bedrooms offer hardwood floors and built-in desks, combining charm with functionality. The primary bedroom includes a private full bath, creating a comfortable retreat. Additional highlights include a lower-level room, a workshop with walkout access, a tandem garage with room for vehicles and storage, and a fully insulated walk-up attic offering exciting possibilities for future expansion, hobbies, or additional storage. If you're looking for a solidly constructed home with acreage, character, and room to grow, this property presents a rare opportunity to enjoy country-style tranquility without sacrificing convenien

578 Old Sherman Hill Rd, Woodbury

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Woodbury Homes for Sale

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