Browse All Woodbury CT Properties for Sale

Welcome to Bacon Pond House. A seamless blend of 19th-century soul and 21st-century luxury. Situated on over 3 acres, this antique Colonial has been thoughtfully revived to honor its heritage while offering every modern convenience. The interior, lovingly brought back to life, features wide-plank flooring and exposed hand-hewn beams that anchor the home's historic character. The rooms are designed for both intimacy and entertaining. A cozy sitting room and a dedicated office/library-complete with a classic fireplace-offer quiet retreats. For larger gatherings, the front-to-back living room, with windows on three sides, is bathed in natural light. At the heart of the home is the remodeled kitchen, which opens to the dining room centered around the original refurbished center core fireplace. Upstairs, four bedrooms await. The primary bedroom offers a new ensuite bath detailed with custom tile. The three additional bedrooms share a fully renovated bathroom with a soaking tub/shower combo. Thoughtfully curated, professionally designed interior furniture and fixtures are available upon request. The property has benefited from extensive renovations that include new bathrooms and kitchen, floor refinishing, a new well, upgraded septic, and more; a substantial list is available upon request.

253 Bacon Pond Rd, Woodbury

$874,900

4 Beds ⋅ 5 Baths ⋅ 24172449 MLS

Beautiful Colonial set on a private 3+ acre lot in sought-after Curtiss Meadows, ideally located on the southern end of Woodbury abutting the Southbury line. Set back from the cul-de-sac entryway, this well-cared-for home offers a wonderful blend of privacy, comfort, convenience, and thoughtful updates. The level, light-filled driveway provides easy access, while the peaceful setting creates a true sense of retreat just minutes from Woodbury and Southbury town centers, commuting routes, and everyday amenities. Offering 3,865 sq. ft. of finished living space on the main two levels, plus an additional 550 sq. ft. recreation room in the walkout lower level, this spacious home provides plenty of room to live, work, and entertain. The first floor features a gourmet kitchen with granite countertops and a large center island perfect for gathering, a spacious great room with cathedral ceiling, formal living and dining rooms, and a cozy den with fireplace. Upstairs, an open foyer/sitting area leads to a comfortable primary suite and three generously sized bedrooms. The exterior is beautifully maintained and includes a privacy fence, rear patio, and three-car garage. Recent improvements add even more value, including a new HVAC and central air conditioning system installed in March 2026, along with solar panels added by the owners to help curb rising energy costs. The two fireplaces give wonderful comfort and warmth.

8 Curtiss Mdws, Woodbury

$645,000

3 Beds ⋅ 3 Baths ⋅ 24165212 MLS

QUAIL RUN On the cul de sac - 4 NEW HOMES ON FLAT LOTS! They might be what you have been looking for - SMALLER & SMARTER new homes with PRICES TO MATCH. Beautiful 1 acre+ lots on shared common drives surrounded by 12 ACRES OF PRIVATE OPEN SPACE. This is QUINTESSENTIAL WOODBURY - Quiet, woodsy and BEAUTIFUL! Construction has begun on 2 homes with anticipated completion in August. #94 is a 3 BR, 2.5 BA FARMHOUSE STYLE SPLIT LEVEL with large front porch, oversized 2 car garage, CATHEDRAL LIVING ROOM and finished lower level with laundry room and half bath.

94 Quail Run Rd, Woodbury

$765,000

3 Beds ⋅ 3 Baths ⋅ 24159088 MLS

QUAIL RUN On the cul de sac - 4 NEW HOMES ALL ON FLAT LOTS! They might be what you have been looking for - SMALLER & SMARTER new homes with PRICES TO MATCH. Beautiful 1 acre+ lots on shared common drives surrounded by 12 ACRES OF PRIVATE OPEN SPACE. This is QUINTESSENTIAL WOODBURY - Quiet, woodsy, and BEAUTIFUL! Construction has begun with completion possible in early October. #86 is a 3 BR, 2.5 BA Cape with FULL FRONT PORCH, 2 car attached garage and OPEN BUT LIVABLE floor plan. LL set up for future finishing.

86 Quail Run Rd, Woodbury

$1,395,000

5 Beds ⋅ 5 Baths ⋅ 24168618 MLS

Step through the doors of history and into one of Connecticut's most treasured colonial residences. Built in 1760 and proudly listed on the National Register of Historic Places, the Jabez Bacon House is a rare masterpiece of 18th-century American architecture that has endured with remarkable grace for over 260 years. This distinguished home has also been recognized for its exceptional preservation and character, having been featured in Early American Life magazine and Historic Homes magazine-an honor that speaks to its authenticity and enduring appeal. This stately five bedroom home showcases original architectural details that collectors and history enthusiasts dream about. Seven fireplaces anchor the home's character across its generous 4,800+ square feet. Five beautifully paneled rooms reveal the craftsmanship of a bygone era, while antique wide-board flooring runs throughout, whispering stories of centuries past beneath every footstep.

30 Hollow Rd, Woodbury

$699,900

4 Beds ⋅ 3 Baths ⋅ 24165323 MLS

Watch the parade from your front yard, walk to school, walk to the excellent restaurants in town, walk to the library and to the local park and market! Fabulous location! One of Woodbury's last remaining homes built in the late 1600s. This charming residence offers a unique blend of historic character and modern convenience, ideally situated for those who appreciate easy access to local shops, parks, and restaurants. The interior of the home boasts a rich history with exposed wooden beams, 4 fireplaces, and classic hardwood floors, creating an inviting and warm atmosphere. Outside, a private patio with an open fireplace provides an ideal setting for relaxation or entertaining, surrounded by lush perennial gardens. Adding to the property's versatility is a separate guest house. This additional structure is perfect for an artist's studio, offering a quiet and inspiring space for creative pursuits, or it can serve as a professional office. Woodbury is known for its historical properties, with some homes dating back to the late 17th century. Main Street offers a charming experience with its antique shops, local restaurants, and vibrant Memorial Day parades. Woodbury is known for its picturesque downtown area, featuring beautiful streets and historic houses. Litchfield Hills are home to numerous wineries, forming part of Connecticut's Wine Trail,where you can enjoy tastings and scenic vineyards. The region also boasts farm-to-table restaurants that highlight local produce

339 Main St S, Woodbury

$499,999

3 Beds ⋅ 3 Baths ⋅ 24162836 MLS

Experience the charm of this classic Cape Cod style property, featuring 3 bedrooms and 2 cozy fireplaces that invite warm gatherings on 1 acre of land perfect for outdoor enjoyment. This country eclectic home blends timeless architecture with modern comfort, offering a serene retreat that captures the essence of country living. Whether you're relaxing by the fire or exploring the great outdoors, this property promises a welcoming and tranquil lifestyle.

110 Brushy Hill Rd, Woodbury

$400,000

24155988 MLS

Rare Main Street commercial property available in Woodbury, CT. The land and the building upon it are being sold in "as is, where is" condition. Neither the probate court system, the attorney, or the broker have any knowledge as to any deficiencies on the property or if they even exist Located in the OS 60 zone, interested parties should consult with the planning and zoning to verify their proposed use is allowed. Final sale is contingent on Probate Court approval.

1545 Main St N, Woodbury

$179,900

24150303 MLS

Discover your own private sanctuary on this enchanting ~4-acre parcel of pristine land perched along scenic Carmel Hill Road in historic Woodbury, CT. Nestled in the heart of Litchfield County's rolling countryside, this remarkable property captivates with mesmerizing views of a sparkling waterfall and the gentle flow of a serene river-nature's own symphony right at your doorstep. Imagine awakening to the soothing sounds of cascading water and birdsong, with sunlight dancing across the wooded landscape and open vistas. Perfectly positioned for tranquility yet convenience, the lot offers easy access to the charming town centers of both Woodbury and neighboring Bethlehem-minutes from boutique shops, acclaimed restaurants, antique treasures, and community events. This is more than land; it's a canvas for your dream home, family compound, or legacy retreat, surrounded by the timeless beauty of Connecticut's countryside. Sale is conditional upon successful subdivision approval, which is underway with the Town of Woodbury (site plan attached, tet hole results available upon request, lot for sale is Lot #2 on site plan). A rare opportunity to secure a slice of paradise with extraordinary natural features and endless potential-don't miss this gem! Property sale will be contingent upon subdivision approval. Site plan available.

Carmel Hill Rd, Woodbury

$999,900

3 Beds ⋅ 3 Baths ⋅ 24146826 MLS

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 with a cathedral ceiling and fireplace, and formal living and dining rooms, each with its own fireplace. Upstairs, the primary suite boasts a vaulted ceiling with exposed beams, accompanied by two additional bedrooms and a walk-up attic. This will be a brand new house when complete; new mechanicals, new insulation, new wiring, new plumbing, new kitchen and baths - a new home with the charm of old. The exterior could be equally impressive, offering two post-and-beam barns, and a beautifully landscaped level lot. The Middle Quarter zoning adds extra versatility, allowing you to run a business from home and even expand the living space into the barns. This is truly one of the best locations in Woodbury!

27 Middle Quarter Rd, Woodbury

$1,450,000

3 Beds ⋅ 3 Baths ⋅ 24139312 MLS

Open Meadow Farm, a beautifully maintained property offering a blend of rural charm and modern conveniences. Set on 9.88 picturesque acres, this property features three fenced fields, ideal for horses or other livestock and a two-story barn equipped with four stalls, a tack room, gravel storage area and a gleaming concrete main floor. Recent updates include a paved driveway with turnaround, back patio, new heating system, a powerful 20KW whole house generator and four energy efficient mini-splits ensuring year-round comfort. Enjoy the beautifully landscaped gardens, several tranquil ponds, a babbling brook and perennial flower beds. This spacious home boasts three bedrooms and three full baths, a well-appointed kitchen, office space, a full basement and both attached and detached garages. Relax on the screened porch overlooking the ponds and bring your four-legged friends-this property is ready for you to move right in. Come enjoy the charming little town of Woodbury, only 90 minutes to NYC

819 Main St N, Woodbury

$1,790,000

4 Beds ⋅ 5 Baths ⋅ 24136657 MLS

Located in picturesque Woodbury, voted Most Charming Town in CT by Reader's Digest in 2018, 2020 and 2024 and featured by Travel + Leisure among the 10 Best Places to Live. Experience the undeniable charm of this circa 1685 residence-one of the oldest continuously inhabited homes in the county. Thoughtfully restored and beautifully updated, this remarkable property blends centuries of character with today's modern conveniences. Inside, the open floor plan creates a warm and inviting flow, with three cozy sitting rooms surrounding the impressive central hearth. The chef's kitchen features a large center island, breakfast bar, and sweeping views of the expansive lawn-perfect for both everyday living and entertaining. Original details abound, including hand-hewn beams, wide king's board flooring, and the historic cooking fireplace that anchors the heart of the home. Recent upgrades include a new HVAC system with humidification and numerous other enhancements (see attachments for the full list). A new mahogany deck overlooks the level backyard, leading toward a picturesque bridge, sparkling pool, and inviting cabana. Two barns sit near the parking area-one offering garage space and the other ready for your imagination: ideal for a future guest house, studio, or recreation room, this barn has new propane heat, water and electric service. This extraordinary home offers the rare opportunity to own a piece of history-beautifully updated for modern living.

55 Good Hill Rd, Woodbury

$289,000

2 Beds ⋅ 2 Baths ⋅ 24078648 MLS

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, level, potential building lot. Convert office to residential, build across river and rent out office or use office and workshop yourself. There are 2, 7ft' garage doors leading to basement/workshop. The potential uses for this property are many!

439 Washington Rd, Woodbury

$675,000

24084159 MLS

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 of road frontage, the property provides ample access and visibility, ideal for a potential for a private residence or nature-inspired retreat. Enriching the value of this land, the Flanders Nature Center/ Land Trust encompasses the northern boundary with about 200 acres and the southern edge with about 28 acres, ensuring the preservation of the natural surroundings and offering a legacy of conservation. This adjacency to protected lands promises enduring tranquility and a haven for local flora and fauna. Conveniently located just minutes from the vibrant Woodbury Center, future owners will enjoy the blend of seclusion with the convenience of nearby amenities, including boutique shopping, fine dining, and cultural experiences. Create something truly special in the heart of Litchfield County.

Cowles Rd, Woodbury

$990,000

3 Beds ⋅ 2 Baths ⋅ 24086595 MLS

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 suite and two other bedrooms while the upper level offers an office and a loft, both with a cathedral ceiling and views to the outside.

523 Main St N, Woodbury

Start Your Search

Prev
1
2
of 2
Next

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.

Woodbury Real Estate

Our website features the best real estate search for homes, condos, land and foreclosure properties available in Woodbury and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes.

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire.

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood!

Considering selling or refinancing your home? Get an INSTANT property valuation now!