Woodbury CT Real Estate & Homes for Sale

Beautifully constructed and perched atop a scenic 3+ acre lot, this stately gambrel colonial is just a 5-minute drive from charming downtown Woodbury. Offering 4 to 5 bedrooms, this home features everything one would expect in almost 3400 square feet of living space; a formal dining room, a large front-to-back living room with a fireplace and hardwood floors, and a spacious eat-in kitchen with a center island. The generous family room is the heart of the home, boasting vaulted, beamed ceilings, a cozy fireplace, hardwood floors, and French doors leading to both the front and back yards. Upstairs, you'll find four bedrooms and two and a half bathrooms, along with a private au pair suite located above the garage-perfect for guests or extended family. Additional highlights include an oversized two-car garage, a walkout lower level with a third garage door, and enough space to accommodate three to four smaller vehicles. The exterior is impeccably maintained with expansive lawns, a pond with wild flowers, mature plantings, blue stone walkways and patios, classic stone walls, and a backyard pavilion- ideal for enjoying the outdoors while staying shaded from the sun.

Welcome to 229 Bacon Pond Road, Unit 144, a spacious 2-bedroom, 1-bath condo nestled in the highly desirable Woodberry neighborhood. This unit offers great potential for buyers eager to add their personal touch and create a truly special home. Though it may benefit from some updating, it provides a solid foundation with a comfortable layout and ample natural light. The open living space is perfect for relaxing or entertaining, while the two bedrooms offer versatile living options. The location is ideal, close to local amenities, parks, and community features. Whether you're an investor or a buyer looking to customize your living space, this property presents an excellent opportunity to add value and make it your own. Don't miss out on this chance to own in a sought-after area.

Litchfield County Condo - 1st floor unit, set in park like setting. Enjoy all Woodbury has to offer - outstanding restaurants, antiquing, hiking trails, garden shops and more. Close to several nationally recognized private schools. Easy access to highways for commuters. If complex loses power, there is a propane generator to run water systems to units. Highest & Best by Sunday, 5/18/25, 3 pm

Gracious townhome just completely reborn! Excellent quality renovations throughout! Bright and open living flow. Great for entertaining. The sun-splashed living room is cheerful. The broad picture window views the lovely landscape and lawn. The new high-end kitchen boasts soft-close doors with very ample cabinet and counter space. There is a convenient first floor laundry. Dining area views private patio and garden area. The primary bedroom is very comfortable size. lt will accommodate a king size bed easily. The fresh, stylish baths have ceramic floors. Nice ceramic tile surrounds the tub/shower. Woodbury Village encourages creative plantings. Choose your favorite perennials to greet you on your walk up the nice brick walkway. All very cheerful! We are very green around here! It is truly parklike. The entry drive is a striking colonnade of evergreens. Just across from the front dooryard is an extensive level bowling green, perfect for croquet, badminton, soccer or football. There are woods to wander. There is ample parking. Set in the gentle knolls of Woodbury. Silence + birdsong = tranquility. Walk to sweet Nonnewaug Brook to enjoy the gentle babble, spy on the birds or drop a line. Amble to the quaint, genteel village center. Hike, bike about happily. Country jaunts start the moment you leave home. Explore the quaint colonial farmsteads, sunny hillocks and shady dales, woods and waterfalls. 1900 calling wanting their serenity back. Welcome!

Nestled on over four private acres just minutes from downtown Woodbury, this expansive Cape Cod-style home offers a blend of classic charm and exceptional amenities. This four-bedroom residence features a first-floor primary suite, striking beamed ceilings, and three fireplaces, creating an inviting and warm atmosphere. The thoughtfully designed eat-in kitchen opens to an enclosed porch, providing a perfect space for morning coffee or evening relaxation. A spacious deck extends from the main living area, overlooking an in-ground pool and an expansive yard, ideal for outdoor gatherings. This property also includes a two-car garage beneath the main home, as well as a separate detached two-car garage with two horse stalls and a one-bedroom apartment above - an excellent opportunity for multi-generational living, guest accommodations, or potential rental income. Set against a backdrop of open meadows and lush woods, this well-built home presents endless possibilities for customization and value enhancement. Don't miss the chance to own this unique property!

Charming antique home in the heart of Woodbury! Set on a spacious, cleared lot, this beautifully maintained property offers a perfect mix of historic character and modern updates. The kitchen features quartz countertops, stainless steel appliances, and ample cabinetry. With three full baths and a large primary suite with walk-in closet and private bath, comfort and convenience abound. Enjoy the serene sunroom overlooking the expansive yard-ideal for relaxation or entertaining. A classic barn with a loft and finished office space adds versatility for hobbies, storage, or remote work. Just a short walk to the town center, this unique home is a rare opportunity to own a piece of New England charm with today's amenities.

SELLERS ARE REMOVING ALL CARPETS AND INSTALLING LAMINATE HARD WOOD IN LR,DR, UPSTAIRS HALL AND 2 BR'S. (DEN HAS BEEN DONE) NEW STAINLESS STEEL REFRIGERATOR AND PAINTING KITCHEN CABINETS, NEW KITCHEN FLOORING AND COUNTER TOPS. TWO BATHS COMPLETELY GUTTED AND REMODELED. Light, bright, clean! Will be ready to move right in. Natural light floods this home. Crown moldings in living and dining rooms, custom window treatments. First floor den has a vaulted ceiling, skylight and picture window, and new flooring. Primary bedroom has two cozy window seats to relax and enjoy a book in the sunshine. Woodbury Hill is a quiet, small complex with tennis/ pickle ball courts and pool close to the town center. Beautifully landscaped with mature plantings and flowering trees. Subject to final probate approval.

Welcome to Woodbury, a quintessential New England town. This house is located in a very desirable neighborhood, just north of the town center. An inviting covered front porch will greet you. This leads to a 2 story foyer and an open floor plan opens up in front of you! To the left is a formal LR/Den. (cozy up with a good book) To the right is formal Dining Room with a trey ceiling, seats 8-10 people. Foyer leads to the 2 story family room. Tons of light from the large palladium windows, built in shelving, propane fireplace, gleaming hardwood floors. Opens to the exquisite chef's kitchen. This space comes with an eat in area, an island with microwave, plenty of cabinetry, marble counter tops, propane cook top, double wall ovens and pantry. There is a slider that leads to the a relaxing covered deck. Enjoy the wildlife, birds and landscaped yard. There is a large office on the other end of the house as well as a 1/2 bath. The second floor consists of 3 generous bedrooms a hall bath, wonderful laundry room and a primary suite. This space is equipped with a primary bath , shower, jac style tub, double sinks and linen closet. There is also a massive walk in closet and make up area. Really a delight for those clothe hounds! The 3 car attached gar. offers plenty of space for cars and lawn equipment. Easy access to the kitchen The basement is unfinished and awaits your desired finishes. Take some time to admire the landscaping and perennial gardens. Lasting beauty, easy care.

Discover the potential in this generously sized split level 5-bedroom, 2-full-bath home nestled in charming Woodbury, CT. Situated on just over an acre, this property offers ample space inside and out, perfect for growing families and those who love to entertain. While the home is in need of updating, it offers a lifetime roof under warranty on both the home and pool house. A major investment already taken care of and one that you'll never have to worry about again. Discover hardwood floors beneath the carpet, just waiting to be uncovered and restored to their true potential. Step outside onto your back desk to enjoy your morning cup of coffee or relax after a long day. Your private backyard complete with an in-ground pool and pool house, ideal for summer gatherings. Located in a quiet, desirable neighborhood close to schools, shopping, and all that Woodbury has to offer. Whether you're a first-time buyer, a seasoned investor, or simply exploring your next move, this property offers a unique opportunity to own a home that blends the space, location, and can offer long-term value.

Peace and tranquility. If that is what you are looking for, you will find it here in this expansive cape. Located on a quiet country road, it provides the privacy and tranquilitygreat spaces for a variety of lifestyles. For preparing great meals, this oversized kitchen is just the place. Enjoy friends and family as you prepare & serve. Spill over into the 25' x 22' family room with custom woodworking & a lovely fireplace. If you like to entertain in a more formal setting, use the spacious living & dining rooms. There is also a den/office on the main level. Upstairs, a primary bedroom suite as well as 2 additional bedrooms & an additional full bath. On the exterior, a spacious deck, patio a lovely yard as well as a spectacular bonus: a 24' X 35' barn, great for entertaining, using as a workshop or as storage for special vehicles. The options are endless.

Welcome to Woodbury! Rebuilt in 1991, this stunning 3,736 sq ft single-family estate sits gracefully on over 11 acres, offering the perfect blend of refined luxury and serene countryside living. Step inside to discover a spacious, light-filled interior designed for both grand entertaining and comfortable everyday living. With four generously sized bedrooms, multiple living areas, and fine architectural details throughout, every corner of this home exudes sophistication. The gourmet kitchen opens to elegant dining and family spaces, while expansive windows frame picturesque views of the surrounding landscape. Outdoors, a built-in pool invites you to relax and entertain in style, with plenty of room to expand your vision - whether it's a garden, horse paddock, additional dwelling or private vineyard. A three-car garage and circular driveway ensure privacy and convenience, all within minutes of Woodbury's charming town center, fine dining, and schools. This is more than a home - it's an estate, a retreat, and a lifestyle.

Welcome to your North Woodbury bucolic retreat! Escape from it all, nestled along the banks of the Weekeepeemee River with southern views and sunsets falling over the open fields, Heron fishing only yards from your Adirondack chair and Eagles perched on the nearby trees. Yes, this is Home. This 1780 Colonial has been well cared for, for many decades. The first floor offers a large updated kitchen, formal dining room, living/entertaining room, study, parlor, and water closet. Four fireplaces are located on this level. Both a front and rear staircase will take you to the second level, five rooms in total, four currently being used as bedrooms and one as an office. There are two full bathrooms on the second level. A detached two-car garage with potting/storage room also has an additional finished and heated 720 square feet above. Situated 5 minutes to Woodbury Center, 10 mins to Washington Center, and 15 to Southbury/I-84.

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.

This impressive, early 1900s colonial-style barn conversion, uniquely blends historic charm with modern comfort, offering 6 bedrooms, 3 full baths, and spanning 4,245 sq ft on a picturesque 1.59-acre lot. Rich with character, it showcases original architectural details including a hand-carved front door, wood beams, wide plank floors, and wrought-iron hardware. The spacious wraparound kitchen with a center island and custom cabinetry is ideal for gatherings and entertaining. The grand living room is stunning with soaring 20+ foot ceilings, dramatic two-story Palladian windows, and a fabulous 5' wood-burning fireplace. The lower level features a private in-law suite with its own front-porch entrance, modern kitchen, full bathroom, and expansive living area boasting French doors, wraparound windows, private terrace and a second fireplace. Outdoors, a two-level terrace overlooks a sprawling backyard offering privacy and stunning views, inground pool surrounded by lush greenery and vibrant seasonal blooms, and a wonderful three-tier garden for vegetables and herbs, fruit and nut trees including chestnut, butternuts, black walnuts, and multiple sugar maples-perfect for serene relaxation and entertaining. Two separate driveways and an oversized four-car garage provide ample parking, storage, and guest convenience. With a little vision, this home offers the ideal canvas to personalize and create your dream retreat.

Exceptionally constructed contemporary set on almost 9 acres with a beautiful view of distant hilltops. Both the house and the outdoor spaces are truly impressive, perfect for entertaining and nature lovers. With over 7,500 sq ft, the home is spacious with exposed beams, an abundance of windows and many updates & upgrades. The public rooms are open and airy encompassing the kitchen, dining and living room with vaulted ceiling, 2-story windows and stone fireplace. Two sets of doors lead to the outdoor stone patio & pool area. The 1st floor also includes the primary bedroom with full bath and walk-in closet, guest bedroom/office, powder room and laundry room with half bath. Upstairs is the 2nd primary bedroom, 2 add'l bedrooms, glass office with shades and an immense family room with vaulted ceiling, bookshelves, and 2-story windows with view of the pond & far hills. The newly finished lower level has a large rec room, 3 add'l rooms and a full bath with steam shower. New geothermal heating & cooling, solar panels with 2 Tesla batteries, renovated baths, and designed with Greenblock insulation concrete forms providing equivalent to R-50 insulated walls. The park-like grounds offer privacy, freshwater pond, walking trails, mini-vineyard, rolling meadows, 2 sheds, chicken coop, Gunite pool, stone patio, out-door shower & hot tub. A must see for buyers looking for privacy without being remote, a generous sized home to spread out and lots of acreage for outdoor fun! Come take a look

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 is 8 ft wide with oven and crane. Beautiful kitchen with SS, granite, copper apron sink, pantry and raised panels. Walk up attic is finished and is a spacious bedroom with exposed beams. Attached gar is used as playroom. There is a potting shed/workshop, shed and a 1 Br Guest house. Stone patio is accented with an outdoor fireplace and lovely perennail gardens. Once had a successful antique shop here and is perfect for an in-home business or retail space. Guest House is perfect for an in home artist studio or professional use. Once owned by famous people, Oliver Wolcott is one of them. Just a Classic, stunning home. Pride of Ownership here throughout the years. One of the last homes built in the 1600's here in Woodbury. You will fall in love with this one for sure!

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!

Custom-built. This unique home is made for entertaining. 4000 ft.2 home with 3 bedroom suites each containing its own full bath. 5 Bathrooms. 3 Fireplaces. Chef's kitchen with granite counters, double ovens, bow window w/bench seat & walk out to deck. Formal dining room has tray ceiling. Great room with fireplace and full bar. Den/library has fireplace. Bright piano room/sunroom/office also walks out to deck. Master bedroom suite accompanied by a luxurious bath and a private dressing room with a dual closet. All 3 Fireplaces have fans for heat! Allergy free home has a comfort electronic system air cleaner built into furnace. Whole house has hardwood floors. All rooms CAT wired & wired for music. Professional wine cellar. Family room with fireplace and a half bath. French doors onto patio. Beautiful stone wall in back yard has 7 columns with granite tops, light fixtures, 3 Walpole woodworker gates. Heated 3 car garage with Epoxy covered flooring. Home in Superior condition! Surrounded by rolling views & privacy with free space behind your home and on both sides! Enjoy the hawks view surrounding you without having extra taxes! New roof installed! Subject to homeowner finding suitable housing.

Nestled in one of Woodbury's most sought-after enclaves, 77 North Gate Rd epitomizes refined living. This meticulously updated 4-bedroom, 2.5-bathroom residence spans approximately 2,519 square feet, offering a harmonious blend of modern sophistication and timeless charm. Constructed in 2016, the home's contemporary design is complemented by high-end finishes and an open-concept layout that seamlessly connects living spaces. The gourmet kitchen, adorned with top-tier appliances and elegant countertops, flows effortlessly into the dining and living areas, creating an ideal setting for both intimate gatherings and grand entertaining. Step outside to discover a beautifully crafted two-tier stone patio, perfect for alfresco dining or serene relaxation amidst the tranquil surroundings. The expansive 2.3-acre lot provides ample space for outdoor activities and future enhancements. The residence also features a substantial unfinished basement, presenting a blank canvas for customization-be it a home theater, fitness center, or additional living quarters. Situated in a neighborhood renowned for its prestige and community spirit, this home offers not just a residence, but a lifestyle of unparalleled comfort and convenience.

Nestled in lovely Woodbury and in a gorgeous neighborhood, a spacious colonial that requires a little TLC to bring it back to life. A contractor's dream. No Access - Please do not disturb occupant or walk on the property. There are no previews allowed. Please do not disturb occupant. Drive by preview only. Please do not park in driveway nor walk the property. Seller has never occupied the property and information is provided to their best knowledge. Interior photos were taken prior to occupant moving in in addition to a few recent exterior photos. If occupant does not leave at closing, new owner will assume occupant & contents. New owner will be responsible for obtaining possession of the property upon closing. Agent has not been inside the house. Information taken from previous listing information and field card. Potential owner to do their own diligence.

A long winding drive leads you to Four Winds Farm. Perched on the hill, this remarkable 33.98-acre property includes a 4,500 sq ft, 11 room, 4 bedrooms, 4.1 bath residence as well as a home for your horses. The contemporary house has many updates throughout, cathedral ceilings, tall windows, multiple sliders to exterior entertainment areas and spacious deck. There is central air, a security system, central vac, generator, and 4-bay heated garage. The spectacular grounds include the inground gunite saltwater pool, spacious composite deck, mature professional landscaping, and amazing views of distant hills. For the horses there is a two-story 8 stall stable, 14 paddocks with aisle ways, 120' x 200' riding ring with Atwood Equestrian Surface (re-surfaced 4 years ago), 7 run-in sheds, 20' x 20' tractor barn and trail. Woodbury designated as Connecticut's "Most charming small town," by Reader's Digest offers tree-lined Main St, parks, playgrounds, hiking trails and streams to dip your toes in on those hot summer days. Also known as the "Antiques Capital of CT," there's no shortage of shops, boutiques and antiques homes lining the historic district. Woodbury is home to a half dozen fun and diverse restaurants and a brewery with music. Just twenty minutes to the historic Palace Theater for concerts, comedy and much more. Forty minutes to Mohawk Mountain for winter fun. 35 minutes to Brewster Train Station and 90 minutes to NYC. Come see what Litchfield Hills has to offer!

House is half finished. Seller has completed much of downstairs including kitchen and living area but still a work in progress. Downstairs is all open with a loft upstairs. Great value and beautiful surroundings sits on half an acre. Worth a look ! There are no disclosures and will not go FHA Woodbury is a beautiful town, make this house your own... *UPDATE Seller is continuing to work on the home, new photos coming soon!*

Discover the charm of this beautifully soon to be restored antique home in the heart of Woodbury! Nestled on the serene Middle Quarter Road, this soon to be renovated vintage gem is just a 2-minute stroll from coffee shops, top-notch restaurants, and the historic Main Street. The home could 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. The exterior could be equally impressive, offering room an in-ground gunite pool, 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!

Come home to a unique 3082 sqft, one of a kind custom built Barn home all set on 5 secluded acres. Featuring an open floor plan, beamed ceilings, oak floors, Plaster Walls, fully applianced Kitchen with breakfast bar, a spacious Family Room with brick fireplace, built-ins, & slider leading to back deck. The Living Room with fireplace is adjacent to a spacious Dining Room area & slider leading to large deck with access to side yard. At the end of the day enjoy the cozy Library with fireplace and built-ins. First floor also has an Office as well as a full Bathroom. As you ascend the stairs to the second floor you will marvel at the unique lighted brick archway. Second floor boasts of lovely Primary Bedroom Suite with brick fireplace & raised hearth, walk-in closets, Full Bath with tub, shower & vanities, and slider leading to balcony. Two other large Bedrooms with skylights, Full hallway Bathroom, and Laundry Room with utility sink. Lower level features an in-law/apartment, Storage Room & Mud Room with storage. This home has easy access to Woodbury's town center, shops, top restaurants, antiquing, and recreation with hiking trails & nearby lake. Enjoy all this property has to offer as well as the area!

LIMITED TIME OFFERED AT THIS PRICE!! ACT NOW!!! This elegant Colonial in Carriage Hills features approximately 5700 sqft of living space, including a walk-out lower level suitable for an in-law suite. The main level has wood floors, formal living and dining rooms, an eat-in kitchen, bedroom, a full bath, and a family room with a fireplace leading to an oversized deck. Upstairs, there are three bedrooms, a full bath, and a primary suite with a spa-like bath and loft area. The lower level features three finished rooms and a full bath. The private backyard is surrounded by trees and dotted with perennial gardens. Woodbury is one of Connecticut's best small towns filled with charming shops, antiques, coffee shops and restaurants and it's only 90 minutes from NYC