Woodbury, CT Homes for Sale with Acreage

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 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

Exceptional Colonial in one of Woodbury's finest developments, beautifully set among similar distinguished homes at the end of Silver Brook Lane. Thoughtfully updated over the past five years with high-quality materials and careful attention to detail, this 4,000+ square foot residence offers an ideal blend of elegance, comfort, and modern convenience. The heart of the home is the stunning

Tim Drakeley Drakeley Real Estate, Inc.

Welcome to Upper Grassy Hill Living!

Susan Corleto William Pitt Sotheby's Int'l

Discover the charm of this beautiful antique home in the heart of Woodbury! Nestled on the serene Middle Quarter Road, this vintage gem is being restored by the current owner and is just a 2-minute stroll from coffee shops, top-notch restaurants, and the historic Main Street. The home will be meticulously updated from the ground up, featuring wide board antique flooring, a stunning great room

Tim Drakeley Drakeley Real Estate, Inc.

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.

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

Gloriously Peaceful, Private, Magnificent views...This exceptional residence among similar spectacular homes welcomes you with a dramatic two-story entry - designed for both refined entertaining and comfortable living. The heart of the home is a beautifully appointed chef's kitchen featuring porcelain countertops with waterfall island and slab backsplash. New Sub-Zero appliances: 48inch Sub-Zero

Becky Hood William Pitt Sotheby's Int'l

Charming Gentleman's Farm on 5.76 Acres. Welcome to this beautifully maintained gentleman's farm, perfectly set on 5.76 level acres of open pasture and riding space. Ideal for horse enthusiasts, the property features four barns with a total of 10 stalls, two wash stalls, and a 20x60 meter riding arena with quality stone dust and sand footing. The grounds offer a wonderful mix of functionality and

Heather Crabtree RE/MAX RISE

Completely renovated and move-in ready, this single-floor ranch offers effortless living with modern updates throughout. The brand-new kitchen is absolutely stunning and opens to the dining and living area, making the space perfect for both everyday comfort and entertaining. Enjoy peace of mind with all-new bathrooms, windows, lighting fixtures, a newly installed septic system and a brand new

Erin Loucks BHGRE Gaetano Marra Homes

Discover this beautifully updated ranch-style home ideally situated on over an acre of level, private land. Offering 2292 square feet of comfortable one-level 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 and expansive living room with cathedral ceilings,

Joseph Conforti West View Properties, LLC

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

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

Fantastic Potential in this home. Three bedroom Cape Cod sitting on 5.50 acre lot with a giant barn that has great potential living space to convert into an in-laws set up, office, studio space or music studio to fit your lifestyle. Home freshly painted interior and exterior. New updated kitchen and bathrooms. All newer energy star appliances. Walk out into your large screened in porch to enjoy

Beatriz Conroy William Raveis Real Estate

Price Improvement for this Charming Country Retreat- A perfect alternative to Condo Living! Nestled on a serene 3 acre lot with picturesque stream, this property offers the tranquility of country living while maintaining easy access to nearby amenities. One level living- enjoy the convenience of the primary bedroom with spacious walk-in closet on the same level as the open floor plan

Betsy Rosa Berkshire Hathaway NE Prop.

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

Located in picturesque Woodbury, voted Most Charming Town in CT by Reader's Digest in 2018, 2020 and 2024 and featured by Travel + Leisure among the 10 Best Places to Live. This stately circa 1845 home blends historic character with comfortable living. Set along scenic Good Hill Road and surrounded by lush, established gardens, featuring a black bottom gunite pool, private terrace, welcoming

Christina Zainc BHGRE Gaetano Marra Homes

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.

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

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