Step into timeless charm with this classic 1800 New England Colonial in historic Woodbury. Thoughtfully curated wallcoverings weave subtle, boutique elegance and modern p...

Looking for the ease of one level living, a beautiful backyard, and the peace of mind that comes with major updates already completed? This Woodbury ranch checks all the ...

Welcome to this stunning, fully remodeled Colonial in Woodbury, located in beautiful Litchfield County! Situated on over 2 acres with a private pond, this home features 4...

Looking for a convenient in town location? Built in 1940, this delightful vintage colonial is loaded with the charm of the 1940's. The front to back living room offers a ...

Completely renovated and move-in ready, this three-bedroom ranch in North Woodbury has been gutted to the studs and beautifully rebuilt throughout. The open-concept layou...

Private Litchfield County Retreat on Nearly 10 Acres Tucked among the picturesque hills of Litchfield County, along the desirable Woodbury/Roxbury line, this distinctive...

LARGE COLONIAL HOME ON A 4+ ACRE PRIVATE LOT- THIS HOME OFFERS A FULLY APPL KITCHEN WITH CENTER ISLAND- DINING RM THAT OPENS TO A FORMAL LIVING RM- MAIN FLOOR FAMILY RM W...

Set well back from Weekeepeemee Road in one of Woodbury's finest locations, this exceptionally well-built Colonial offers approximately 5,900 square feet of thoughtfully ...

A private retreat with Million dollar views! Nestled at the end of a peaceful cul-de-sac, this 3800+ Colonial offers a rare combination of privacy, space, and breathtakin...

Welcome to history, charm, and an incredible location-the best of both worlds! Tucked along a quiet side road, this lovingly cared-for antique offers a peaceful, private ...

Reader's Digest named Woodbury the "Most Charming Small Town in Connecticut" in 2024 and received the same recognition in 2020 and 2018.That fits this home perfectly. 63 ...

Charming Brick Ranch on 2+ Acres Nestled on more than two acres in a peaceful setting, this well-built brick ranch offers the perfect blend of privacy, comfort, and conve...

A Place Where Home Feels Like A Getaway Welcome to 69 Nonnewaug Road, where peaceful country living meets the charm of Woodbury! Set on approximately 9.47 acres, this 3-...

Welcome home to this beautifully maintained 4-bedroom, 2.5-bath center hall colonial, ideally situated on a desirable cul-de-sac just minutes from the charming town cente...

The John Cramer House at 10 Weekeepeemee Road is listed on the National Register of Historic Places and is a wonderful example of Greek Revival architecture. Rich in peri...

BACK ON THE MARKET with a NEW SEPTIC being installed, NEW WELL, and MORE. This generous 5-bedroom home offers a generous footprint to put your personal touches on. Boasti...

CHARM, CHARACTER & CLASSIC NEW ENGLAND APPEAL IN HISTORIC WOODBURY! Welcome to this distinctive 1895 Colonial farmhouse, where timeless architectural character blends bea...

Imagine starting your morning with a cup of coffee on the gorgeous wraparound front porch as you take in the view of Radey Pond or spending warm summer evenings entertain...

Some homes make their impression at the front door. This one begins long before it. Set nearly out of sight on almost three acres, the home is approached by a long drivew...

Welcome to 34 Pilgrim Trail, a home thoughtfully cared for and enjoyed for 25.5 years. This peaceful Woodbury property features granite kitchen countertops, a tiled backs...

Set on 3.29 picturesque acres bordering conservation land, this beautifully maintained and thoughtfully remodeled country Cape is filled with character, custom craftsmans...

From the moment you pull up to this House on the Hill, you will feel right at home. Built when homes were designed for gracious, comfortable living, it feels elegant yet ...

A Fresh Look at a Home with So Much Flexibility! Come take a look at this versatile and beautifully maintained home, where generous living spaces and unexpected possibili...

Original owner, large Colonial Home with 4 room, private entry inlaw suite on the main level. Close to town center and schools. With all this s/footage it's price at a...

Classic 1930s Colonial set along Main Street in Woodbury, offering the timeless character and craftsmanship of the era. Thoughtfully set back from the road on an expansiv...

Impressive and spacious 5,815 sq. ft. well maintained residence with BRAND NEW ROOF and all new skylight windows(installed 8/15/26) offering exceptional one-level living ...

Exceptional value and opportunity on 3.5 gorgeous acres! Bring this home back to its original charm. Features hardwood floors throughout and a cozy front porch. The upper...

Timeless Elegance & Immaculate Detail. Welcome to The Naramore House, a piece of living history. Lovingly preserved since 1898, this pristine colonial home seamlessly ble...

Steeped in 18th-century charm, this rare 1747 Saltbox estate seamlessly marries historic integrity with modern luxury. Tucked away on a peaceful country lane, the main ho...

Spacious Colonial in desirable Carriage Hills offers approximately 5,700 square feet of living space, including a walk-out lower level that is well suited for an in-law s...

Exceptional opportunity to renovate and create your dream country estate on 12.69 private acres in the heart of Woodbury. Privately sited along a quiet country road with ...

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 a...

INVESTORS TAKE NOTICE!! A rare opportunity to bring your vision to life in beautiful Woodbury. 3BR, 2.5 bath Cape just over 2,000 square feet of comfortable living space ...

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, ma...

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...

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 appr...

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 of...

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 ...

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 ...

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 fro...

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+...

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 ...

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 o...

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 Liv...

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...

To be built Modern style home with gorgeous southern views and privacy from your neighbors. Enjoy the wall of glass overlooking a bluestone patio, and beautiful views abo...