4-Bedroom Homes for Sale in Woodbury, CT

Welcome to a piece of New England history-an 1835 Farmhouse lovingly updated for today's living while preserving all its timeless charm. Set on 4.7 acres with a sun-kissed field framed by quiet woodlands, this property offers the perfect balance of country serenity and in-town convenience. From here, you can stroll into the heart of Woodbury, known for its storybook charm, delightful restaurants,

Heather Crabtree Coldwell Banker Realty

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

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.

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

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

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

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

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

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

Wonderful Ca 1840's Colonial on 3 acres with wrap around porch. In the heart of Woodbury, this lovely antique is just a short stroll to Main St, parks and town amenities. Charming period details throughout the home include built-ins and beautiful wide board wood floors. The current owners have lovingly cared for the home with many updates including exterior painting, updating garage doors to

Maria Taylor Klemm Real Estate Inc