$605,420Average Value$270Average Price per Sq Ft22Homes For Sale
Antiquities abound, but so do modern amenities
Fittingly for a town founded more than 100 years before the birth of the United States, Woodbury is known as the “Antiques Capital of Connecticut.” But while the town, established in 1673, may be old in a chronological sense, it also has a vibrant present. With its assortment of restaurants, shopping and outdoor amenities – not to mention its proximity to Route 6 – Woodbury has plenty of modern conveniences to make clear the fact that the town is more than just a destination for those seeking vintage items. "Woodbury has a lot going for it," says Realtor Pamela Dostillo. "It's famous for its antique stores, but it's also got some great restaurants. And it's somewhat rural, without being too far off the beaten path for commuting."
A pilgrimage for antiquing
A town doesn’t acquire the moniker of “Antiques Capital of Connecticut” by accident, especially considering the fact that Connecticut has existed since 1636. A town zoning law allowed residents to use their homes as places of business, and when antiques were very much in vogue beginning in the 1960s, Woodbury residents began to sell antiques out of their historic homes. Today, more than 50 antiques dealers operate in Woodbury, and offerings range from odd trinkets like corn-husking pegs to elaborate 18th-century furniture. Popular stops along the famed Woodbury Antiques Trail include G. Sergeant Antiques, specializing in English, American and Continental furnishings; Farmhouse Antiques & Design, offering farmhouse-style furnishings and interior design consultations; and Pantry & Hearth Antiques, an 18th-century farmhouse adorned with early American antiques displayed in period room settings.
Woodbury Deli is located right off Main Street and is busy all hours of the day.
Woodbury Floral Designs is located on Hollow Road just off Main Street.
The simple sign above the door of Sumpin' Sweet Bakery is dwarfed by the amazing aroma.
The Woodbury Deli interior is immaculate and cozy, making you feel like you are eating at home.
Woodbury Floral Designs has the best home decor gifts.
The interior of Sumpin' Sweet is bright and sweet just like their food.
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Other shopping and dining in Woodbury
But there’s more to Woodbury than just antiques. Canfield Corner Pharmacy is a local gathering spot and social hub for residents, who peruse the assortment of sundries and sit at the old-time soda fountain that, while no longer operational, has seen more than its fair share of customers in its time. Past employees of Canfield’s have fond memories of one particular customer, a blonde woman who regularly filled prescriptions at the pharmacy and sat at that very soda counter while she waited for her medications, chatting with patrons and employees and even volunteering to change the diaper of one of the pharmacist’s babies. That woman’s name was Marilyn Monroe.
Woodbury has also established itself as a culinary destination known for its eclectic dining options. Among the local favorites on Main Street are 1754 House, a Colonial-style tavern and inn known for its contemporary American cuisine, and Woodbury Brewing Co., a casual eatery that hosts live bands, open mic nights and trivia contests, making it the center of the town’s nightlife.
Woodbury Library is a local hub and manages one of the only book stores in the area.
Woodbury Library hosts regular events in their multi-purpose room.
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Panoramic views of event-filled parks
The iconic fire tower at OThe iconic fire tower at Orenaug Park is a highlight of the town’s recreational preserves. A popular trail that starts near the town library leads to the tower, which stands 260 feet above Main Street and offers stunning vistas of the surrounding Pomperaug River Valley. The town-operated park, which is open year-round, also features a natural stone amphitheater known as Bethel Rock, believed to be the site of the town’s first religious services. On the other side of Main Street is Hollow Park, where children have access to playscapes and baseball fields and residents gather for community events, including the annual Fire Department Carnival each September. The Flanders Nature Center & Land Trust offers seasonal classes and summer camps for youth as part of a stated mission to provide interactive opportunities to encourage lifelong learning about the natural world. Exploration of that natural world is made easy by miles of trails that wind through the Trust’s 2,100 undeveloped acres. renaug Park is a highlight of the town’s recreational preserves. A popular trail that starts near the town library leads to the tower, which stands 260 feet above Main Street and offers stunning vistas of the surrounding Pomperaug River Valley. The town-operated park, which is open year-round, also features a natural stone amphitheater known as Bethel Rock, believed to be the site of the town’s first religious services. On the other side of Main Street is Hollow Park, where children have access to playscapes and baseball fields and residents gather for community events, including the annual Fire Department Carnival each September. The Flanders Nature Center & Land Trust offers seasonal classes and summer camps for youth as part of a stated mission to provide interactive opportunities to encourage lifelong learning about the natural world. Exploration of that natural world is made easy by miles of trails that wind through the trust’s 2,100 undeveloped acres.
Orenaug Park can be accessed from multiple points in Woodbury including this spot on Park Road.
The Orenaug Park Fire Tower is a popular hike and offers 360 degree views.
Flanders Nature Center & Land Trust trails are maintained and mix mowed lawn and wooded paths.
Flanders Nature Center & Land Trust pond walk is a local favorite.
Hollow Park has a playground, pond, walking trails, and ballfields.
Strong Meadow Preserve trails wind their way over and through East Meadow Brook.
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Striking contrast of Colonial and modernism
Historic residential structures stand out along Main Street, a tree-lined thoroughfare, and saltbox-style Colonial homes sit next to Cape Cods along the outer quiet neighborhood streets. New developments in the area include more contemporary-style housing, offering a compelling architectural contrast. The further from Main Street, the larger the lot sizes tend to be, with homes sitting on multi-acre plots in picturesque, wooded areas. The median home price in Woodbury hovers around $575,000, and buyers should expect to pay an average of $242 per square foot. A two-bedroom/one-bathroom ranch-style home can sell for $240,000, and prices can go up to $1.7 million for a Colonial-style contemporary build. "Woodbury is a place where you have options in terms of lot size," says Dostillo. "You can get a home with a lot of land or, if you prefer, you can get less land. It's not a place where everything is uniform and laid out the same. It's really a very pretty town."
New developments like this one on Strongfield Drive are featuring homes with 2-3 garages.
A Main Street Woodbury Cape Cod style home.
Picket fences and porches line this classical home on Main Street.
Downtown apartments on Judson Ave have mature trees, convenient parking, and town walkability.
A Main Street Woodbury Queen Anne style home.
A Main Street Woodbury bungalow style home.
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College-ready students stay ahead
Woodbury is served by Regional School District 14, which earns an overall grade of B from Niche. Students can attend Bethlehem Elementary, Woodbury Middle and Nonnewaug High School. Bethlehem earns a B from Niche, Woodbury Middle earns a B-minus and Nonnewaug earns a B. Students at Nonnewaug High School can participate in any of 40 school-sponsored clubs and activities, and they have the opportunity to play 30 varsity-level sports. There are also several excellent private schools in the area, including nearby Kent School, which earns an A-plus rating from Niche.
Mitchell Elementary School is beautiful with or without decorations.
The grand entrance of Woodbury Middle School.
The modern aesthetic of Nonnewaug High School is simple stunning.
Woodbury Library children's corner overlooks the main downstairs area.
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Community events
Woodbury is also the site of several community-wide events throughout the year. Hollow Park is the site of several holiday gatherings, and the town’s annual tree-lighting ceremony takes place at nearby North Green. Readings, adult panel discussions and children’s reading events are held at the Woodbury Library on Main Street.
Photography Contributed By
Chris Mantz
Video By
Mike Dunleavy
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On average, homes in Woodbury, CT sell after 73 days on the market compared to the national average of 54 days. The median sale price for homes in Woodbury, CT over the last 12 months is $500,000, up 7% from the median home sale price over the previous 12 months.
Welcome to a piece of New England history-an 1835 Farmhouse lovingly updated for today's living while preserving all its timeless charm. Set on 4.7 acres with a sun-kissed field framed by quiet woodlands, this property offers the perfect balance of country serenity and in-town convenience. From here, you can stroll into the heart of Woodbury, known for its storybook charm, delightful restaurants,
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
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
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Property Id: 2072922Light and bright 2 Story 1 Bedroom Condo available for immediate occupancy. This unit comes with a spacious and open first floor lay out, kitchen with extra cabinet space and more. The second floor has a full bathroom and spacious Bedroom with ample closet space. This condo is located on Woodbury most desirable areas and will not last long so dont wait schedule a tour
First floor two bedroom, eat in kitchen, shower bath, laundry. IMMACULATE and immediate occupancy for the right fit. Owners were just awarded the 2025 Town of Woodbury Historic Preservation Award. Eleazer Crane House - circa 1800 on 1.3 acres in rural Woodbury. Sun filled spacious apartment. Looking for that quiet tenant to be compatible with the upstairs tenants for a cohesive living experience.
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
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Frances MirabilioTown & Country Realty and Design, LLC
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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
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