Woodbury Homes for Sale

Private 3-Acre Retreat! Tucked away on a peaceful and private 3-acre lot, this beautifully maintained 5-bedroom, 3-bath home offers the perfect blend of luxury, space, and functionality-with over 3,450 sq ft of living space designed for comfort and entertaining.The main level features a flexible layout with either a first-floor primary suite and office or two spacious bedrooms, offering options

Kary Apanovitch Coldwell Banker Realty

Experience elevated New England living at 6 Strong Field Road, an exceptional 2024 custom-built Cape Cod residence set on a private, manicured 1-acre lot in one of Woodbury's most desirable enclaves. Designed for discerning buyers, this 4-bedroom, 2.5-bath masterpiece blends architectural sophistication with everyday comfort. Inside, you're welcomed by an airy open-concept floor plan, enhanced by

Mary Ann Bennett Drakeley Real Estate, Inc.

Lovely well maintained colonial just minutes to town. The dramatic double height entry invites you into the main living area which opens to the stunning luxury kitchen and sunny breakfast nook. The living room boasts a stone fireplace flanked by a picture window for enjoying sunset views. The main floor is completed by an addl den/media room and a formal dining room. Upstairs the primary suite

Stacey Matthews W. Raveis Lifestyles Realty

Welcome to Upper Grassy Hill Living!

Susan Corleto William Pitt Sotheby's Int'l

Welcome to one of the most charming communities in Connecticut. This darling of an antique home sits in the heart of Woodbury, CT. It is a Dutch colonial dating to circa 1700, bought in 1750 by a well-respected, wealthy local merchant/ financier, Jabez Bacon. The building became the town's first general store, known as the Red Store. After Bacon's death, the property served as a school and later

Lorraine Consiglio Coldwell Banker Realty

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

Jeff Colt Showcase Realty, Inc.

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

Michael Vartolone William Raveis Real Estate

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

Beatriz Conroy William Raveis Real Estate

Come home to a unique 3082 sqft, one of a kind custom built Colonial 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

Ron Nettleton William Raveis Real Estate

Falling water...Step away from the day and step on the property and take a deep breath. Instantly feel the weight of the worlds worries fade away. Commune with nature in this sanctuary property. From the front entry views direct to the back lush greenery, beautiful rock outcroppings and every window in between you can feel natures touch. Magnificent gardens and respite areas to sit and reflect

Mary Ann Bennett Drakeley Real Estate, Inc.

This comfortable Townhouse unit is located in a quiet complex located off Route 6 and close to downtown Woodbury. The main level has a half bath and laundry room with washer & dryer. There is a private patio off the kitchen accessible thru sliding glass doors. Upstairs there are 2 good sized bedrooms with ample closet space. the Unit comes with 1 built in air conditioner and 2 window units. There

Jack Gregory Sette Real Estate LLC

This well-appointed Colonial offers four spacious bedrooms and is set on a secluded lot for added privacy. The front-to-back living room features built-in shelving and a classic fireplace. A sunlit main-level family room includes a raised-hearth fireplace and expansive windows. The primary suite offers French doors leading to a covered porch overlooking the private backyard-ideal for quiet

Lawrence Madow Calcagni Real Estate

Spacious 3-bedroom, 2.5-bath end unit with 1,640 sq ft of interior space, ready for your personal touch. This 1980-built home features all hardwood floors, crown molding, central heat and air, and marble kitchen countertops. While the property needs cosmetic updates, it offers strong potential to add value. The finished basement provides clean, usable storage space. Great opportunity for buyers

Derek Greene Derek Greene

NOTE NEW PRICE POINT FOR THIS LOVELY WOODBURY RESIDENCE! TRAVEL OVER THE POMPERAUG RIVER AND WATERFALL TO THIS UNIQUE, ENCHANTING OASIS. Situated close to the center of Woodbury, yet the ambiance of this "country" setting provides the feeling of being miles away from it all! This is a unique opportunity to reside in an historic mill village on one of Woodbury's most picturesque town-maintained

Terry Lee Adams Adams & Adams Real Estate

Looking for space? Need a workshop? Collect cars? Need room for the in-laws? This ranch-style home might be the perfect fit! Just minutes from town, the property offers a variety of opportunities. The main level features three bedrooms, two bathrooms, a living room with a gas log fireplace, a formal dining room, and a spacious eat-in kitchen. The partially finished lower level includes a family

Sindy Butkus Klemm Real Estate Inc

Shingle style home with horse barn, paddocks & riding arena, set on over 9 acres with a gorgeous westerly view of Roxbury's bucolic rolling hills! This property is an equestrian's dream. Horse barn w 5 stalls w waterers. 2nd level in barn loft for additional space. 6 horse paddocks w waterers & electric fence. Perfectly set riding arena w views. Built in 2013, no expense was spared on the

John Donato Jr Showcase Realty, Inc.

Majestically perched on 2+ private acres, this beautifully maintained three-bedroom Colonial offers seasonal panoramic views of rolling hills and treetops, providing a picturesque year-round backdrop while being close to town. Thoughtfully updated with modern finishes, this home blends comfort and style with ease. Step into the inviting Great Room, where soaring ceilings with exposed beams,

Wendy Brazauskas Coldwell Banker Realty

Experience the true essence of country living in this classic Saltbox Colonial, perfectly situated on 2.5 acres of peaceful, wooded land in picturesque Woodbury. Surrounded by nature's beauty, this home offers a tranquil retreat. Inside, gleaming HW floors flow throughout a timeless layout designed for comfortable living and relaxed entertaining. The spacious eat-in kitchen features a welcoming

Tammy Powling Coldwell Banker Realty

Excellent 2nd floor unit. One of only 4 units in the complex that has direct interior access to the Laundry facility. Close to parking and mail. This bright unit has been well maintained and is move in ready. Updates to kitchen and bath with stall shower installed. Don't miss out on this great opportunity. Close to town for shopping, restaurants and recreation.

Jeff Boucher Drakeley Real Estate, Inc.

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

Heather Crabtree Coldwell Banker Realty

SELLERS HAVE REMOVED ALL CARPETS, INSTALLED LAMINATE HARD WOOD THROUGHOUT BOTH LEVELS. NEW STAINLESS STEEL REFRIGERATOR, PAINTED KITCHEN CABINETS W NEW HARDWARE, NEW KITCHEN FLOORING AND COUNTER TOPS. TWO BATHS COMPLETELY GUTTED AND REMODELED. Light, bright, clean! Is now ready to move right in. Natural light floods this home. Crown moldings in living and dining rooms, custom window

Mary Ann Bennett Drakeley Real Estate, Inc.

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

Donna Bannon BHGRE Gaetano Marra Homes

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

Tom Slekis Berkshire Hathaway NE Prop.

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

Maria Taylor Klemm Real Estate Inc

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,

Matthew Amatruda Drakeley Real Estate, Inc.

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

Maria Taylor Klemm Real Estate Inc

Need space! 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 or for your au pair . 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

Sindy Butkus Klemm Real Estate Inc