Woodbury, CT Homes for Sale

If you are looking for peace and tranquility, you will find it here in this expansive cape. Located on a quiet country road, it provides the privacy and tranquility as well as great spaces for a variety of lifestyles. For preparing great meals, this oversized kitchen is just the place. Enjoy friends and family as you prepare & dine. Spill over into the 25' x 22' family room with custom

Donna Bannon BHGRE Gaetano Marra Homes

The Tomlinson House, built in 1786, offers a rare chance to own a piece of Woodbury's history. Set on 5.29 acres along Middle Road Turnpike, with an additional .87-acre lot across the street, this 4-bedroom Colonial combines period charm with enduring potential. Historic character is evident throughout-restored wide-board hardwood floors, original millwork, and four (non-working) fireplaces,

Kathryn Bassett William Pitt Sotheby's Int'l

Built in 1900 as a barn and converted to a home in 1990, the architecture fuses countryside charm and mid-century design - two contrasting genres married to create an interesting and unique experience. The home is entered via an offset entry that opens into an all-seasons sunken sunroom overlooking the expansive backyard. You flow directly into the eat-in kitchen, which is outfitted with maple

Michael Caporizzo William Pitt Sotheby's Int'l

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 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.

Charming one-level living in a beautiful setting. Enjoy the ease of one-level living in this thoughtfully designed home, nestled in a peaceful and scenic location. Step inside to an inviting open floor plan that seamlessly connects the bright living and dining areas-perfect for both relaxing and entertaining. Just off the dining room, you'll find a cozy family room ideal for gatherings or quiet

Nancy Langrock William Raveis Real Estate

Welcome to Woodlake! This spacious 3-bedroom, 3-full-bath townhouse offers a flexible layout, abundant natural light, and multiple outdoor spaces to enjoy. The main level features a bright living room with sliders to a large deck, creating the perfect indoor-outdoor flow. The kitchen includes ample cabinetry, an eat-in dining area, and its own slider to the back of the home that offers a brand

Chelsea Stinson Coldwell Banker Realty

Discover this beautifully updated ranch-style home ideally situated on over an acre of level, private land, backing onto a tranquil nature preserve in the heart of Woodbury. Offering 2292 square feet of comfortable living space, this 3-bedroom, 1.5 bath home combines timeless character with modern upgrades-perfect for those seeking space, tranquility, and convenience. Inside, you'll find a bright

Joseph Conforti BHGRE Gaetano Marra Homes

Welcome to a rare find in scenic Woodbury, CT! A spacious and adaptable 6-bedroom, 3 full bathroom home perfectly suited for multigenerational living. Nestled on over 2 private, park-like acres with a peaceful pond, this property offers a unique combination of comfort, functionality, and natural beauty. Thoughtfully designed for flexible living, the home features separate living quarters,

Shawna Mucherino Coldwell Banker Realty

Step into this well-cared-for 3 bedroom, 2 bath Victorian offering just over 2,000 sq. ft. of comfortable living space. Filled with natural light and character, this home blends historic charm with thoughtful updates, including a mix of original and newer engineered hardwood floors, and two generously sized, updated baths. Original architectural details add warmth and personality, while newer

Rhya Szymansky Drakeley Real Estate, Inc.

Tucked away in absolute privacy, yet centrally located, this exceptional estate offers 6,300+ square feet of refined living space that seamlessly blends country sophistication modern luxuries. Crafted w/warmth & character throughout, the home boasts wide board hardwood floors, coffered ceilings, French doors, exposed beams, & built-ins. With 13 thoughtfully designed rooms, the home features 6

April Furey Keller Williams Realty Prtnrs.

Simply an amazing opportunity awaits. This custom styled Cape Cod home, majestically sitting high on a hill above the town of Woodbury. Welcome to 158 Hazel Plain Road. Allow your imagination to run wild as you stroll through this wonderful property. The adjectives are endless, huge rooms, hardwood flooring, 1st floor master suite. View the kitchen/family room combination with French doors to a

Michael Ferris eXp Realty

The epitome of where Contemporary Design, open spaces, light and efficiency meet the true warmth and pride of local master craftsman. If 9 secluded acres is not peace and privacy enough, your abutting neighbor is 128 acres of protected land owned by Flanders Nature Center. Live amongst the trees and fabulous backdrop of rock outcroppings. Some selective clearing could bring back distant mountain

Mary Ann Bennett Drakeley Real Estate, Inc.

Positioned on a scenic lot, this versatile property offers multiple avenues for value-add improvements and long-term growth. The main single-family residence includes a legal in-law apartment with a walk-out basement-ideal for multi-generational living or flexible use. Two additional outbuildings-a two-story studio and a workshop-provide excellent potential for repurposing as creative spaces,

Mikaila Riedel eXp Realty

Much of the interior of this home is complete. There is still work to be done on the exterior of the home Everything in the interior was gutted and completely remodeled so everything is new. One bed downstairs and a large loft upstairs which could be a second bedroom or office. Basement is now partially finished and can easily be extra living space. Outside of the home is a work in progress.

Gayle Forster Century 21 AllPoints Realty

NEW PRICE OFFERING! .... 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 roads. Enjoy this lovely home

Terry Lee Adams Adams & Adams Real Estate

NEW PRICE! Don't wait! 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 room, office space, and a full bath. Built in 2008, the

Sindy Butkus Klemm Real Estate 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

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

Light, bright, clean! Ready for immediate occupancy. Natural light floods this home. Crown moldings in living and dining rooms, large picture window, built in and FP are focal points of the living room, DR has sliders to the deck with garden views. First floor den has a vaulted ceiling, skylight and picture window. Great for home office or guests flex/br space. Kitchen w newer appliances and

Mary Ann Bennett Drakeley Real Estate, Inc.

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

Tom Slekis Berkshire Hathaway NE Prop.

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.

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

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

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

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

Welcome to Benson Woods - an exclusive community of 78 single-family homes designed for active adults. This beautifully maintained home boasts an open floor plan, featuring a great room with a cozy fireplace and soaring cathedral ceilings. The eat-in kitchen is a chef's delight, complete with a spacious island, dining area, white shaker-style cabinets, granite countertops, and a stylish tile

Mary Ann Hebert BHGRE Gaetano Marra Homes