Woodbury Homes for Sale

Welcome to Woodbury, Connecticut—a picturesque town nestled in the heart of Litchfield County, where charm meets community. Known for its rich history and stunning natural surroundings, Woodbury offers a unique blend of small-town allure and modern convenience. With its tree-lined streets, historic buildings, and a vibrant downtown area, this town is a perfect place for families, professionals, and retirees alike.

Woodbury is renowned for its excellent schools, making it an ideal destination for families seeking quality education for their children. The town is also home to numerous parks and recreational areas, providing ample opportunities for outdoor activities like hiking, biking, and picnicking. The scenic landscapes, including the beautiful Pomperaug River, create a serene backdrop for everyday life.

If you're considering making Woodbury your home, you're in luck! The real estate market here offers a diverse selection of homes for sale, catering to various tastes and budgets. From charming historic properties that exude character to modern single-family homes equipped with the latest amenities, there's something for everyone. Whether you’re looking for a cozy cottage or a spacious family home, Woodbury's real estate options are sure to impress.

Living in Woodbury means embracing a vibrant community spirit, with local events, farmers' markets, and friendly neighbors at every turn. With easy access to major highways, commuting to nearby cities is a breeze, making it an ideal location for those who work in the Greater Hartford area or beyond. Discover the charm of Woodbury and find your dream home in this enchanting Connecticut town today!

Newest Woodbury Homes for Sale

$1,395,000

3 Beds ⋅ 3 Baths ⋅ 24192284 MLS

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 views. Step through the screened stone-and-timber breezeway to a newly expanded patio and custom firepit crafted directly from native fieldstone, all beneath a classic wood-shingle and copper roof. The surrounding grounds function as a true New England compound. A separate two-bedroom carriage house offers built-in guest quarters with a covered porch and an oversized 2.5-car garage. Nearby, a newer two-story 40'x28' barn provides flexible space for a creative studio, vehicle storage, or livestock, complemented by two additional storage sheds. Recent improvements include, but are not limited to, a new cedar-shingle roof with copper downspouts (2025), new A/C, fresh interior paint throughout (2026), and refinished flooring. It is an unmistakable rural sanctuary with abundant room for horses, chickens, and hosting friends and extended family.

509 Weekeepeemee Rd, Woodbury

$525,000

3 Beds ⋅ 2 Baths ⋅ 24189460 MLS

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 ideal for home office or living space with plenty of natural light, windows and recessed lighting. Cutting edge solar panels save on electric bill! Conveniently located close to all amenities, shopping, dining, and major highways. Enjoy all that Woodbury has to offer - rated best town by Yankee Magazine. "Sold as is condition" a must see!

212 Upper Grassy Hill, Woodbury

$819,900

3 Beds ⋅ 3 Baths ⋅ 24192675 MLS

Welcome to 17 Curtiss Drive! This one-of-a-kind 1.8-acre property offers the perfect blend of historic charm and modern convenience, featuring a well-maintained 1900 single-family home, an attached 2-car garage, and an impressive detached 24' x 50' heated 3-car garage built in 2022. Step inside the home and be welcomed by a charming foyer leading to wide-board hardwood floors and six mini-split systems (2019) that provide efficient heating and cooling throughout. The inviting living room features custom built-ins and flows seamlessly into the spacious kitchen, complete with stainless steel appliances, ample cabinetry, recessed lighting, a pantry closet, and basement access. Just off the kitchen is an updated half bath with tile flooring and laundry hookups. Off the kitchen the elegant dining room offers crown molding and plenty of space for entertaining. Completing the main level is a spacious primary suite with double closets and a beautifully updated full bath boasting heated tile floors, a skylight, recessed lighting, chair rail molding, and a linen closet. An adjoining den with custom built-ins provides the perfect space for a home office, reading room, etc. Upstairs, you'll find two generously sized bedrooms, each with walk-in closets and shared access to a Jack-and-Jill bathroom featuring a dual-sink marble vanity. The basement includes 200-amp electrical service, Energy Star hot water heater, well tank (2018), and additional laundry hookups. Outside, enjoy

17 Curtiss Rd, Woodbury

$398,000

3 Beds ⋅ 2 Baths ⋅ 24186179 MLS

Warm and welcoming, this vintage home with a classic rocking chair front porch is ideally located within walking distance of Woodbury's town center. Beautifully maintained, it blends timeless character with thoughtful updates throughout. A gracious foyer with hardwood floors and a wall of closets provides exceptional storage. The living room features hardwood floors, built-in shelving, and an electric fireplace, while the dining room showcases a classic built-in cupboard. The updated country kitchen offers Vermont soapstone countertops and new flooring, and a convenient main-level laundry room with a half bath completes the first floor. Upstairs are three bedrooms and a full bath. Energy-efficient improvements include newer windows and doors, along with individual thermostats in every room for personalized comfort. An enclosed rear porch provides the perfect mudroom or everyday entry. Outside, the level backyard has been transformed into a park-like retreat with a new patio, attractive landscaping, and plenty of space for entertaining, gardening, or simply relaxing. A shed provides additional outdoor storage. Located in Woodbury, named Reader's Digest's "Most Charming Small Town" three times, this home offers easy access to restaurants, galleries, cultural venues, day spas, hiking trails, ski areas, wineries, and equestrian facilities. Approximately 90 minutes from Manhattan, it offers the perfect blend of small-town charm and convenience. Seller reviewing offers.

9 Spring St, Woodbury

$525,000

3 Beds ⋅ 2 Baths ⋅ 24191493 MLS

Classic 1800s vintage Colonial in Connecticut's most charming town! Located within a short drive of all major conveniences, area private/public schools and parks, this three bedroom, two bath home has something for everyone! Situated on a beautifully level lot, enjoy your 1.55 acres by throwing the ball around, entertaining on your slate side patio or terrace area. The backyard barn, named the "Carriage House", is a unique feature of the property that is just waiting for you to cultivate your favorite hobby. On the main level of the home you will find a spacious country kitchen with hook up for a woodstove. The formal dining room can fit the relatives for the upcoming holiday season, and the formal living room, with center fireplace, beams with natural light! Rounding out the first floor is a study with custom-built bookcases and a full bath off the kitchen. Upstairs are spacious bedrooms, a full bath with clawfoot tub, and a bonus room, currently used as another bedroom. Lastly, the walk up attic is fully floored and highly functional for your storage needs or other use. Come and appreciate how this property reflects Woodbury's 19th century antique flair!

520 Washington Rd, Woodbury

$1,100,000

4 Beds ⋅ 4 Baths ⋅ 24192457 MLS

Spacious Colonial in desirable Carriage Hills offers approximately 5,700 square feet of living space, including a walk-out lower level that is well suited for an in-law suite or au pair quarters. The main level features wood floors, formal living and dining rooms, an eat-in kitchen, a bedroom, a full bath, and a family room with a fireplace that opens to an oversized deck. Upstairs, you'll find three bedrooms, a full bath, and a spacious primary suite with a spa-like bath and loft area. The walk-out lower level includes three finished rooms plus a full bath, offering flexible space for guests, extended living, recreation, or work-from-home needs. The private backyard is surrounded by trees and accented with perennial gardens. NEW Roof June 2026. Located in Woodbury-one of Connecticut's most beloved small towns-the home is close to charming shops, antique stores, coffee shops, and restaurants, all just about 90 minutes from New York City.

16 Gate Post Ln, Woodbury

$675,000

4 Beds ⋅ 3 Baths ⋅ 24192145 MLS

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 living room with soaring vaulted ceilings, a fireplace, and walls of windows overlooking the surrounding landscape. The main level includes a spacious primary suite, private office, butler's pantry, and access to expansive decks that invite outdoor entertaining. Upstairs are 3 additional bedrooms and an open den, while the unfinished walk-out lower level offers endless possibilities for future living space. The property's 12.69 acres provide a beautiful backdrop with open land, mature trees, and a four-stall barn, offering flexibility for a variety of country lifestyles. Priced to reflect the opportunity for renovation and updating, this is an exceptional chance for investors, builders, or buyers looking to customize a solidly built home in one of Woodbury's most desirable locations. With great bones, an outstanding setting, and significant upside potential, this property is ready for its next chapter. Sold as is.

348 Hoop Pole Hill Rd, Woodbury

$749,900

3 Beds ⋅ 3 Baths ⋅ 24190540 MLS

Charming and full of character, this beautifully maintained three-bedroom Cape offers the perfect blend of comfort, warmth, and convenience in the heart of Woodbury. Set on a picturesque property with mature perennial gardens and a fenced-in yard, the home feels peaceful and private while being just a two-minute walk from downtown shops, restaurants, the library, schools, community center, and nearby hiking trails. Inside, hardwood floors and abundant natural light create a warm and inviting atmosphere. The welcoming living room features a fireplace, while the bright south-facing sunroom provides a relaxing space to enjoy throughout the day. The dining room includes a charming corner cupboard that adds timeless New England character. The finished lower level offers flexible space for exercise, hobbies, or creative pursuits and includes a sauna, shower, and fully equipped darkroom. Additional highlights include a two-car garage and beautifully landscaped outdoor spaces. A rare opportunity to enjoy distinctive features, exceptional charm, and an ideal in-town location in one of Litchfield County's most desirable communities.

31 Mountain Rd, Woodbury

$579,000

4 Beds ⋅ 3 Baths ⋅ 24191268 MLS

Have you been looking for a Woodbury home with that special balance of privacy and accessibility? This well-maintained four bedroom, three bath Colonial may just be the answer. The heart of the home is a bright, sunlit kitchen and breakfast nook that opens into a spacious family room with a wood-burning brick fireplace and skylights in a vaulted ceiling; sliders lead to a large 32 x 16 foot deck overlooking the level back yard. A formal living room offers additional space for entertaining and holidays are a breeze thanks to a formal dining room, with all the rooms flowing easily from one to the next. The primary bedroom suite with three additional bedrooms on the upper level feature hardwood floors (one bedroom has hardwood under the carpet) and both smartly updated baths look fresh and inviting. There's easy access to the attic through a guest bedroom closet. The partially finished lower level offers more flexible space and is where you find the laundry and mechanical rooms as well as access to the two-car garage. Gardeners will appreciate the greenhouse, and the spacious yard offers nearly limitless options for those with a green thumb. Lovingly cared for by one owner for the past forty years, you will not be disappointed when you see this wonderful property. Come home to Woodbury, the gateway to extraordinary Litchfield County.

38 Grey Fox Trl, Woodbury

$895,000

4 Beds ⋅ 3 Baths ⋅ 24172964 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! 2 homes IN CONTRACT, 1 home available for FALL DELIVERY and this new build to start in later summer/early fall for SPRING DELIVERY 2027.

96 Quail Run Rd, Woodbury

$495,000

4 Beds ⋅ 3 Baths ⋅ 24188362 MLS

Sited privately on 2.7 scenic acres in Woodbury's desirable Cardinal Hill neighborhood, this classic four-bedroom Colonial offers a perfect blend of quiet country living and everyday functionality. As part of a low-fee, self-managed neighborhood association, residents enjoy a wonderful sense of privacy and peace of mind. The main level features a traditional flow, including a formal living room and a separate dining room ideal for gatherings. Across the back of the home, a comfortable, open living space connects the eat-in kitchen-complete with a center island bar-to a cozy family room centered around a fireplace. This bright living area looks out to serene, elevated treetop views. A spacious pantry, dedicated laundry room, and a half bath complete the well-organized first floor. Upstairs, the primary bedroom suite features a private full bath and a spacious walk-in closet. Three additional bedrooms are nicely proportioned and share a full hallway bath. A traditional home in a peaceful, established setting just a short drive from the vibrant shops, eateries, and historic charm of downtown Woodbury.

18 South St, Woodbury

$575,000

3 Beds ⋅ 3 Baths ⋅ 24185429 MLS

Cute as a button Cape Cod style home in charming and historic Woodbury! A lovingly cared for home within a short drive of main street, area schools, Walker Road Winery and all other major conveniences. Step right into this light and bright home that provides a newly remodeled kitchen, oak floors throughout, two bedrooms on the main level and charming exposed beams. Comfortable and cozy, sit and relax in the living room that is just off the kitchen, and end your day in the first floor primary suite that includes two walk-in closets with bath including a newer vanity and stall shower. Rounding off the main level is another full bath. Upstairs find two additional bedrooms and full bath. Several recent upgrades include a newer roof, gutters, and siding. The two bay attached garage features workshop, 100amp sub panel, and loft area for additional storage or conversion into an in-law apartment with connection to the septic system already! Still need more space for storing your equipment and toys? Included on this property are two outbuildings, one is 12x20, the other is 18x33. Town records show 3 bedrooms, septic was replaced as 4 bedroom. Bring your hobbies and make this charming Cape yours today!

206 Minortown Rd, Woodbury

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