$602,384Average Value$290Average Price per Sq Ft34Homes 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.
1/6
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.
1/2
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.
1/6
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.
1/6
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.
1/4
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
Interested in learning more about homes in this area?
Reach out to
Allysa DeRosa,
an experienced agent in this area.
GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
View GreatSchools Rating Methodology
On average, homes in Woodbury, CT sell after 79 days on the market compared to the national average of 56 days. The median sale price for homes in Woodbury, CT over the last 12 months is $490,000, up 11% from the median home sale price over the previous 12 months.
Steeped in 18th-century charm, this rare 1747 Saltbox estate seamlessly marries historic integrity with modern luxury. Tucked away on a peaceful country lane, the main home boasts original wide-plank wood floors, dual fireplaces, twin staircases, authentic built-ins, and freshly renovated baths. At its heart is the kitchen featuring Viking appliances and granite counters that open to garden
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
Well maintained and updated Raised Ranch 3 bedroom 1.5 bathrooms home ready to move in! Open concept living room/dining room and kitchen that opens on to a gorgeous 12'x30' deck overlooking a beautiful fenced in backyard in the woods make for a very private setting. This home has all new windows, a newly updated kitchen with stainless steel appliances and granite countertops, finished lower-level
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
Exceptional opportunity to renovate and create your dream country estate on 12.69 private acres in the heart of Woodbury. Privately sited along a quiet country road with seasonal long views, this 2,972 sq. ft. contemporary offers an outstanding combination of acreage, privacy, and potential rarely found at this price point. Designed for comfortable living, the home features a dramatic sunken
Move right into this beautifully updated 3-bedroom, 2-bath townhouse offering style, comfort, and low-maintenance living. Gleaming hardwood floors flow throughout the home, complemented by vaulted ceilings, a skylight providing abundant natural light. The updated galley kitchen features tasteful tile backsplash and efficient design, opening to a spacious living and dining area highlighted by a
Steeped in 18th-century charm, this rare 1747 Saltbox estate seamlessly marries historic integrity with modern luxury. Tucked away on a peaceful country lane, the main home boasts original wide-plank wood floors, dual fireplaces, twin staircases, authentic built-ins, and freshly renovated baths. At its heart is the kitchen featuring Viking appliances and granite counters that open to garden
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
The finest condo complex in one of Litchfield Counties most charming towns! Woodbury Hill is a lovely community of townhouse style homes in a very attractive setting and features a saltwater pool and tennis/pickleball courts. #17 has seen many upgrades over the past dozen years including new windows, renovated kitchen and baths, upgraded heat pump HVAC and water heater, as well as recent paint
At Woodlake, you're not just buying a home, you're buying a lifestyle. From being FHA Approved condos, to water views at every balcony, trail walks to boat rides to fountains and everything in between, Woodlake truly offers the peaceful, serene setting that we all dream of. This 3 bedroom, 2.5 bath freshly painted end unit has endless possibilities. Need a main level bedroom or office? One can be
Nestled in the highly desirable town of Woodbury, this charming Cape offers just over 2,000 square feet of comfortable living space with endless potential. The home features 3 bedrooms, 2.5 bathrooms, and beautiful hardwood floors throughout. A dedicated home office with custom built-in shelving provides the perfect space for working from home or studying. The inviting living room includes a cozy
Just 2 hours from New York City, this exceptional lakefront retreat offers a rare blend of privacy, natural beauty & turnkey luxury. Tucked at the end of West Lake Rd and bordered by the protected woodlands of Flanders Nature Center Preserve, the property enjoys sweeping, unobstructed views across pristine Lake Quassapaug to historic Tranquillity Farm, designed by McKim, Mead & White. Lake
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
Don't miss this beauty! Lovely Renovated End Unit with year round Rhododendron - greenery privacy at the deck. The summer blooms are spectacular! This condo is close to the Woodlake Community Garden, for those wishing to grow your own veggies! Inside you will notice a light-filled renovated kitchen with granite countertops, tiled flooring, ceiling fan and stainless steel appliances. The living
An exceptional opportunity to own 76.9 +/- acres in one of Woodbury's most desirable locations. This unique offering includes two contiguous parcels to be sold together, consisting of this 14.9-acre parcel and the adjoining 62-acre parcel (MLS #24192209). Featuring a charming 3-bedroom home, the property offers a rare combination of rolling meadows, mature woodlands, and open fields, creating
AVAILABLE SEPT 2026 FOR $3,750/MONTH. Stunning over-sized Cape on serene, park-like grounds adjacent to a nature preserve. Fully furnished, this inviting 2 bedroom home has been lovingly renovated with a great eye for detail. Quiet street centrally located in historic Woodbury. Newly finished hardwood oak flooring throughout. Two full bathrooms. The large living room with fireplace also includes
Welcome to Woodbury Knoll Apartments, where modern comfort meets tranquil, lakeside living. Life unfolds at a different pace here — mornings are inspired by nature's quiet beauty, and evenings unwind in serene surroundings. In our apartments in Woodbury, CT, you'll discover a lifestyle that's vibrant yet peaceful, perfectly balanced, and endlessly welcoming.
Property Id: 2072920 Light and bright 2 Story 1 Bedroom Condo available for 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 don't wait schedule a tour today!
Impeccable large 2nd floor end unit, bright, cheerful and safe location with beautiful views. Freshly painted and professionally cleaned with new carpeting throughout. Rent includes heat, hot water and appliances. Tenant pays electric, cable/internet, renters insurance. Trash and recycling services and all grounds maintenance also included. New mini blinds throughout. Neighborhood is quiet and
STUNNING RENTAL with POOL and TENNIS COURT (with lights). Enjoy summer(offered for July and/or August) 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 comfortable and
This darling little cottage style cape is in the center of Woodbury's Historic District. Recently painted inside and out, new roof, No smokers, no pets. Good credit a must!(700 FICO) Year lease. Landlord maintains lawn care and snow removal. Tenant pays all utilities!
Available immediately. First floor one bed apartment. Front to back filled with natural. Very good size kitchen w granite and breakfast bar, dining room area with half wall bookshelf delineation to Living room with picture window. One bedroom and walk in closet off set in hallway. Hardwood flooring - clean, charming and ready for new tenant. This building was renovated approx 10 years ago w all
Now available for rent! This well-maintained 3-bedroom home features a spacious eat-in kitchen, 1&1/2 baths, and a comfortable layout ideal for everyday living. Under house two car garage provides ample parking and additional storage. Conveniently located and ready for immediate occupancy, this home offers the space and comfort you've been looking for. Schedule your showing today!1 first month's
1-2 BR one bath completely renovated. Laundry in unit, private off street parking. Plowing and lawn maitenance included tenant shovels walk way. Credit check required no smoking or pets
Three Bedrooms one full and one half baths in a spacious duplex. Recently painted, updated kitchen and new carpet. Full unfinished basement for extra storage. Landlord requires good credit and employment history. pets considered. year lease and security deposit required
Apartment 5 is a large, bright, natural light filled apartment. Second floor with front and back private porches. Living room is very spacious with built ins. Kitchen has granite counters and two pantries. Hard wood flooring. Brand new appliances in laundry room. Freshly painted - Ready for immediate occupancy. This is a second floor unit. Rear yard is recently cleared and seeded for all tenants
Welcome home to this beautifully updated single-family rental nestled on 14 private acres, offering the perfect blend of comfort, space, and tranquility. This 2-bedroom, 2-bath home features a new spacious bonus room which leads to the brand-new oversized deck overlooking the surrounding natural beauty. The newly finished walk-out lower level will be great for additional flexible living space or
Local Logic measures the walkability, access to public transit and bikeability of any address. CAP Index provides objective, accurate, and consistent data to help measure, compare, and mitigate crime risks.
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. Our sources include: Accuweather, Public Records and Neustar. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
