Woodbury, CT Homes for Sale with Acreage

Open Meadow Farm, a beautifully maintained property offering a blend of rural charm and modern conveniences. Set on 9.88 picturesque acres, this property features three fenced fields, ideal for horses or other livestock and a two-story barn equipped with four stalls, a tack room, gravel storage area and a gleaming concrete main floor. Recent updates include a paved driveway with turnaround, back

Sindy Butkus Klemm Real Estate Inc

Everything has already been done for you. Just move in, unpack, and enjoy the ease of single-floor living in this beautifully renovated ranch with endless potential below. Completely renovated and truly move-in ready, this home offers effortless living with every major updated already completed. From the brand-new HVAC system and newly installed septic to new windows, lighting, interior and

Erin Loucks BHGRE Gaetano Marra Homes

Nestled in the highly desirable town of Woodbury, this charming Cape offers just over 2,000 square feet of comfortable living space with endless potential. The home features 3 bedrooms, 2.5 bathrooms, and beautiful hardwood floors throughout. A dedicated home office with custom built-in shelving provides the perfect space for working from home or studying. The inviting living room includes a cozy

Rhya Szymansky Drakeley Real Estate, Inc.

Welcome to Bacon Pond House. A seamless blend of 19th-century soul and 21st-century luxury. Situated on over 3 acres, this antique Colonial has been thoughtfully revived to honor its heritage while offering every modern convenience. The interior, lovingly brought back to life, features wide-plank flooring and exposed hand-hewn beams that anchor the home's historic character. The rooms are

Christian Jensen William Pitt Sotheby's Int'l

It's rare to find a vintage estate tucked away from a main road, but this one sits at the end of a private lane, opening to 6.3 enchanting acres framed by stone walls, manicured gardens, and a charming vintage home. The property includes a large custom two-story pole barn, inground pool, detached three-bay garage, and an adorable potting shed. The great room flows into a kitchen with handmade

Mary Ann Bennett Drakeley Real Estate, Inc.

Built in 1854, this 5.91 acre property offers an incredible value impossible to replicate today for the price. The property includes an Italianate stone home with an approx 675 sq foot retail/office room with a separate entrance at the driveway, a 28' x 53' post and beam barn with a full walkout lower level, a large pond, stone walls, incredible perennial garden surround, and a 21' x 45'

Amy Lapierre Coldwell Banker Realty

Beautifully renovated 4-bedroom, 2.5-bath ranch set on a spacious corner lot in one of Woodbury's most desirable locations. Just two streets from Woodbury's nationally recognized Main Street, this home offers the perfect combination of modern updates, comfortable living, and exceptional outdoor entertaining. The complete interior renovation began in 2023 and has recently been completed, creating

Jonathan Pinto Pinto Real Estate Group LLC

Beautifully updated and impeccably maintained, this custom Colonial offers timeless New England charm in a private setting with gorgeous views of a picturesque waterfall and babbling brook. Set on beautifully landscaped grounds with an additional lot included, the home features wide-board hardwood floors, crown molding, custom built-ins, plantation shutters, French doors, and three fireplaces.

Tim Drakeley Drakeley Real Estate, Inc.

QUAIL RUN On the cul de sac - 4 NEW HOMES ALL ON FLAT LOTS! They might be what you have been looking for - SMALLER & SMARTER new homes with PRICES TO MATCH. Beautiful 1 acre+ lots on shared common drives surrounded by 12 ACRES OF PRIVATE OPEN SPACE. This is QUINTESSENTIAL WOODBURY - Quiet, woodsy, and BEAUTIFUL! Construction has begun on 2 homes with anticipated completion in August. #86 is a 3

Scott Volpe Coldwell Banker Realty

Step through the doors of history and into one of Connecticut's most treasured colonial residences. Built in 1760 and proudly listed on the National Register of Historic Places, the Jabez Bacon House is a rare masterpiece of 18th-century American architecture that has endured with remarkable grace for over 260 years. This distinguished home has also been recognized for its exceptional

Lisa Titcomb William Pitt Sotheby's Int'l

Warren's Landing on the Pomperaug is an extraordinary estate where historic character is centered around a beautifully preserved 1890 Greek Revival residence. The home offers four bedrooms, timeless architectural details, spacious rooms, 4 fireplaces and custom built-ins. The impressive six-barn complex provides exceptional flexibility, featuring a retail shop, extensive equipment storage, a

Maria Taylor Klemm Real Estate Inc

The Orton-Martin Homestead. One of Woodbury's oldest homes has been updated for today's lifestyle. History surrounds you with wide board flooring, library built-ins, two fireplaces and 1850 barn. This four -bedroom home offers spacious rooms, three finished levels and hidden delights. Enjoy picnics under the mature trees on your own fenced-in level yard. Sidewalks take you everywhere on Main St

Sindy Butkus Klemm Real Estate Inc

Welcome to Upper Grassy Hill Living!

Susan Corleto William Pitt Sotheby's Int'l

Cute as a button Cape Cod style home in charming and historic Woodbury! A lovingly cared for home within a short drive of main street, area schools, Walker Road Winery and all other major conveniences. Step right into this light and bright home that provides a newly remodeled kitchen, oak floors throughout, two bedrooms on the main level and charming exposed beams. Comfortable and cozy, sit and

Katherine Parlato Drakeley Real Estate, Inc.

Nestled in the well-established Sherman Hill neighborhood, this five-bedroom home offers a generous footprint to put your personal touches on. Boasting wood flooring and newer windows throughout, the main level features a fluid layout designed for effortless living: a spacious living room, formal dining room, an eat-in kitchen, a cozy family room with a fireplace, a private home office, and a

Christian Jensen William Pitt Sotheby's Int'l

Live Stress-Free in This Income-Producing Equestrian Retreat! Enjoy the best of country living while generating income from your property. Rental revenue from a separate 1 BR apartment and 4 of the 10 horse stalls offers a rare opportunity to offset ownership costs! Situated on 5.76 level acres of open pasture and riding space, this equestrian property is ideal for horse enthusiasts, trainers, or

Jill Sloane Brown Harris Stevens

QUAIL RUN On the cul de sac - 4 NEW HOMES ON FLAT LOTS! They might be what you have been looking for - SMALLER & SMARTER new homes with PRICES TO MATCH. Beautiful 1 acre+ lots on shared common drives surrounded by 12 ACRES OF PRIVATE OPEN SPACE. This is QUINTESSENTIAL WOODBURY - Quiet, woodsy and BEAUTIFUL! Construction has begun on 2 homes with anticipated completion in August. #94 is a 3 BR,

Scott Volpe Coldwell Banker Realty

Charming in-town Gambrel Colonial with views of Orenaug Pond, located just up the road from the South Green. Surrounded by historic landmarks such as King Solomon's Lodge, the Hurd House, the Glebe House, and other notable properties, this home offers three bedrooms, three full baths, and one half bath. It also features a remodeled kitchen with stainless appliances that opens to a family room

Sindy Butkus 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.

Sited privately on 2.7 scenic acres in Woodbury's desirable Cardinal Hill neighborhood, this classic four-bedroom Colonial offers a perfect blend of quiet country living and everyday functionality. As part of a low-fee, self-managed neighborhood association, residents enjoy a wonderful sense of privacy and peace of mind. The main level features a traditional flow, including a formal living room

Christian Jensen William Pitt Sotheby's Int'l

Experience the charm of this classic Cape Cod style property, featuring 3 bedrooms and 2 cozy fireplaces that invite warm gatherings on 1 acre of land perfect for outdoor enjoyment. This country eclectic home blends timeless architecture with modern comfort, offering a serene retreat that captures the essence of country living. Whether you're relaxing by the fire or exploring the great outdoors,

Jacqueline Voegeli Manzi Real Estate

Beautiful Colonial set on a private 3+ acre lot in sought-after Curtiss Meadows, ideally located on the southern end of Woodbury abutting the Southbury line. Set back from the cul-de-sac entryway, this well-cared-for home offers a wonderful blend of privacy, comfort, convenience, and thoughtful updates. The level, light-filled driveway provides easy access, while the peaceful setting creates a

Joyce Drakeley Drakeley Real Estate, Inc.

Step into History with Modern Comfort Experience the undeniable charm of this circa 1685 residence-one of the oldest continuously inhabited homes in the county. Thoughtfully restored and beautifully updated, this remarkable property blends centuries of character with today's modern conveniences. Inside, the open floor plan creates a warm and inviting flow, with three cozy sitting rooms

Stacey Matthews W. Raveis Lifestyles Realty