Woodbury CT Real Estate & Homes for Sale

Welcome to Woodbury! 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.

First floor 1 bedroom unit in very good condition. Newer cabinets with granite countertops and hardwood floors. Heat, hot water, trash, snow removal, and grounds maintenance included. Occupied by long term tenant on month to month lease.

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 charming colonial style barn conversion, originally built in the early 1900s, offers 6 beds, 3 full baths, and spans 4,245 square feet on a picturesque 1.59 acre lot. Rich in character, the home showcases original architectural details including a hand carved front door, exposed wood beams, wide plank floors, cabin style latches, and more. The spacious wraparound kitchen with a center island is perfect for gatherings, offering plenty of room for multiple cooks and memorable dinner parties. The grand living room impresses with soaring 20+ foot ceilings, dramatic 2 story Palladian windows, and a cozy wood burning fireplace. On the lower level, you'll find a private in law suite featuring its own entrance, a modern galley kitchen, full bathroom, and an oversized living area complete with French doors, wraparound windows, and a second wood burning fireplace. Out back, a 2 level terrace opens to a sprawling, level backyard with stunning views, ideal for outdoor activities and entertaining. The space also includes an in ground pool and a beautifully landscaped three tier garden. 2 separate driveways and an oversized four car garage provide ample parking, storage, and room for guests.

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

Perhaps the most desirable condominium complex in Woodbury, Woodbury Hill offers a quiet, beautiful, rural location, yet is close to shopping and accessible to major routes. This Putnam's Loft offers a spacious, open entertaining area with living room open to dining room with oak flooring, fireplace and lots of light. The updated kitchen provides access to the deck overlooking rear property. With a main floor primary bedroom, walk in closet and full bath, this is a perfect home. On the upper level, a spacious loft with builts ins, another bedroom and a full bath. There is also an attached 2 car garage, full basement and attic storage. This complex features a pool and tennis. The new owners will be fortunate to call 23 Woodbury Hill home!

Auction Opportunity. Please review FAQ and Property Information Package included in the additional documents on MLS (you may have to request these directly from your agent or the auction company). Asking Price is Opening Bid only. Final price will be determined by competitive bidding. All bidding online, opening April 23 at 4pm and ending April 30 at 4pm. Bidding website available upon request. ~ Stunning 6-bedroom, 6 full bath, 2 half-bath, French-inspired estate with over 9,000 sq. ft. of luxurious living space, set atop one of Woodbury's highest points. This elegant retreat features soaring ceilings, detailed craftsmanship, a chef's kitchen, and grand entertaining areas. The main suite offers a private escape, while 3 additional en-suite bedrooms provide comfort and privacy. Ideal for multi-generational living, the estate includes a 2-bedroom guest house with full kitchen and private entrance, plus an in-law suite above the heated 3-car garage. Outside, enjoy a resort-style infinity pool, hot tub, and expansive decks with breathtaking views. Timeless design meets modern versatility. High bid as of 4/24/25 is $525,000. High bid as of 4/25/25 at 9:04 AM is $600,000.High bid as of 4/26/25 at 8:21 AM is 960,000. High bid as of 4/29/25 is $1,075,000.

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. 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 to be installed in month of March. 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.

Stunning Renovated Antique Home with Scenic Views & Luxurious Amenities, Discover the perfect blend of historic charm and modern luxury in this totally renovated antique home, and Barn set on 9.44 picturesque acres bordering 20 acres of Land Trust. This home offers 4 bedrooms, 3 full baths, and exquisite craftsmanship throughout. Step inside to find new wide plank floors, recessed lighting, skylights, and a wood-burning fireplace, creating a warm and inviting ambiance. The high-end Chef's Kitchen is a culinary dream, featuring granite countertops, Shaker-style cabinets, and top-of-the-line appliances. The Primary Bathroom boasts a large glass shower, with Waterworks hardware, adding a spa-like retreat to your daily routine. Outside, enjoy the beauty of open meadows, a rushing brook, and a breathtaking perennial garden designed by Pound Ridge Nurseries. Stone outcroppings, specimen trees, and charming stone walls enhance the landscape. A renovated in-ground Gunite pool offers the perfect spot for summer relaxation. Entertain in style in the spectacular barn, featuring a floor-to-ceiling stone fireplace, soaring windows, and a loft ideal for an office or study. A three-car garage with a loft for additional storage sits conveniently alongside the barn. This home and Barn have abundant storage throughout! This exceptional property is a rare find-offering privacy, natural beauty, and luxurious living in an unmatched setting. Schedule your private tour today!

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...

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