Woodbury Real Estate

Welcome to Woodbury, Connecticut—a charming town nestled in the heart of Litchfield County. Known for its picturesque landscapes and rich history, Woodbury offers a unique blend of small-town charm and modern conveniences, making it an ideal place to call home.

With its roots tracing back to the 17th century, Woodbury is steeped in history, featuring beautifully preserved colonial architecture and historical landmarks that tell the story of its past. The town is often referred to as the "Antique Capital of Connecticut," boasting numerous antique shops and boutiques that attract collectors and treasure hunters alike. Strolling through the quaint downtown area, you'll find delightful cafes, artisan shops, and local eateries that reflect the town's vibrant community spirit.

Nature enthusiasts will appreciate Woodbury's stunning outdoor spaces. The town is surrounded by scenic parks and nature reserves, offering ample opportunities for hiking, biking, and enjoying the great outdoors. The nearby Lake Quassapaug provides a serene setting for swimming, fishing, and picnicking during the warmer months, while the fall foliage transforms the landscape into a breathtaking tapestry of colors.

Families will find Woodbury to be a welcoming community with excellent schools and recreational programs. The town hosts various events throughout the year, including farmers' markets, festivals, and seasonal celebrations that foster a strong sense of community.

Conveniently located just a short drive from major cities like Waterbury and Hartford, Woodbury combines the tranquility of suburban living with easy access to urban amenities. Whether you're seeking a peaceful retreat or an active lifestyle, Woodbury, CT, is a hidden gem waiting to be explored. Come discover the warmth and charm of this enchanting town!

Newest Listings in Woodbury

$299,999

3 Beds ⋅ 3 Baths ⋅ 24219459 MLS ⋅ Woodlake BLDG.

Enjoy privacy and a peaceful natural setting in this inviting 3-bedroom, 2.5-bath condo at Woodlake in Woodbury! Freshly painted with select updates, this home offers comfortable living and flexible space. The updated kitchen features stainless steel appliances and a casual dining area. Gather around the woodburning fireplace in the living room, or step through the dining room sliders onto your private rear deck-the perfect spot for morning coffee or unwinding outdoors. Upstairs are three bedrooms and two full baths, while the finished lower level provides additional space for a home office, media room, or workout area. Enjoy Woodlake's outdoor trails, pond, picnic areas, and playground, along with nearby restaurants, antique shops, shopping, and convenient highway access. A lovely opportunity to make Woodlake your home!

15 Woods Way, Woodbury

$999,000

3 Beds ⋅ 4 Baths ⋅ 24218620 MLS

770 Washington Road, Woodbury, CT 06798 The Hazel Plain Schoolhouse: Historic Litchfield County Living Reimagined Steeped in rich local history, 770 Washington Road is a charming 1.09-acre Litchfield County property seamlessly blending 19th-century Americana with sophisticated modern luxury. Originally constructed in 1861 as the one-room Hazel Plain Schoolhouse, this landmark property has been lovingly restored, thoughtfully reimagined, and elegantly expanded into an inviting 3-bedroom, 4-full-bathroom home with custom millwork and wide plank flooring throughout. The Main Residence The home's appealing layout prioritizes privacy, comfort, and timeless New England character: * En-Suite Sanctuaries: All three bedrooms feature their own private, full en-suite bathrooms, offering an unparalleled layout for family and overnight guests. The primary bedroom is separated from the hallway by a large room that can serve as a dressing area, workout space, nursery or home office. The primary bedroom has a walkout to a beautiful multi-level stone and mahogany patio, perched under a canopy of mature trees. * Multiple Living and Entertaining Spaces: The home has a gourmet kitchen with custom cabinetry that opens to an inviting family room. A separate living room with a gas fireplace is perfect for cozy evenings. The dining room, lined with custom bookcases, is a wonderful gathering space for family dinners, holiday celebrations, and game nights. * Four Full Baths: A fourth ful

770 Washington Rd, Woodbury

$500,000

4 Beds ⋅ 2 Baths ⋅ 24219457 MLS

Welcome to 47 Atwood Road in beautiful Woodbury! Situated on a gorgeous .84-acre corner lot, this well-maintained 4-bedroom, 2-full-bath raised ranch offers a wonderful combination of comfortable living space, privacy, and truly beautiful surroundings. From the moment you arrive, you'll appreciate the meticulously maintained landscaping, lush green lawns, mature trees, and colorful plantings that make this property stand out. Inside, you'll find a spacious layout featuring four bedrooms, an eat-in kitchen, and a bright, inviting room just off the kitchen with vaulted ceilings and skylights that bring in plenty of natural light. The lower level offers even more flexibility with a finished room, an additional open area, and a full bathroom, perfect for a home office, recreation room, or whatever suits your needs. Step outside and enjoy the peaceful backyard, complete with a deck overlooking the beautifully landscaped grounds. Whether you're entertaining, relaxing outdoors, or simply enjoying the scenery, this property offers a setting that's hard to find. Lovingly cared for inside and out, this Woodbury home is ready for its next chapter.

47 Atwood Rd, Woodbury

$849,900

5 Beds ⋅ 4 Baths ⋅ 24219165 MLS

Set in a peaceful Woodbury neighborhood, 34 Quail Run blends extensive renovations with comfortable indoor and outdoor living. The home features a newly added primary suite, in addition to a secondary suite, offering exceptional flexibility and privacy. Recent improvements include a new roof, windows, gutters, siding, hardwood flooring, kitchen, and bathroom. Outside, enjoy a new Trex deck and newly installed pavers surrounding the pool, creating an inviting setting for outdoor entertaining and relaxation. A private, manicured yard completes the property. Ideally positioned just minutes from historic Main Street's renowned antique shops, local dining, nature preserves, and hiking trails, this home blends classic Litchfield Hills tranquility with easy access to Route 6, Route 64, and I-84.

34 Quail Run Rd, Woodbury

$359,900

2 Beds ⋅ 1 Baths ⋅ 24218073 MLS

This well-maintained ranch offers a streamlined layout and a prime setting on a level, half-acre lot. The interior features a spacious living room centered by a classic fieldstone fireplace, creating a natural focal point for the home. The kitchen and dining area are positioned at the rear of the house, providing a clear view of the private backyard and seamless access to the outdoor living space. With two bedrooms and a full bathroom, the floor plan is efficient and manageable. A standout feature is the oversized back deck, which overlooks a seasonal brook and offers a quiet, wooded backdrop.

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 sizable 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

$634,900

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

$290,000

2 Beds ⋅ 2 Baths ⋅ 24210496 MLS ⋅ Woodbury Village BLDG.

Rare opportunity in desirable Woodbury Village! This charming three-level townhouse offers flexible living space, beautiful natural light, and a peaceful setting in the heart of Woodbury. The main level welcomes you with a spacious living room featuring a large bay window and abundant natural light. The adjoining eat-in kitchen offers generous pantry storage and sliders leading to a private deck overlooking a lovely wooded green space-the perfect spot for morning coffee or relaxing outdoors. A convenient half bath with laundry and additional storage completes this level. Upstairs, you'll find two generously sized bedrooms with ample closet space, including a walk-in closet, along with a full bath and additional linen storage. The finished walk-out lower level adds valuable bonus space and offers endless possibilities as a home office, recreation room, guest space, gym, or additional living area. Sliding doors open to a covered outdoor area and backyard space. The basement has also been waterproofed and features newer carpeting. Additional features include space for a private garden, three portable air-conditioning units (one with heat), a basement dehumidifier, and deck furniture included by the seller. Woodbury Village offers a tranquil setting with expansive green space, mature trees, walking areas, and a river running through the complex-all while being conveniently located just minutes from Woodbury's shops, restaurants, and everyday amenities.

74 Washington Road Unit 40, Woodbury

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Woodbury Real Estate

Newest Listings in Woodbury

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