Woodbury CT Single Family Real Estate, Homes for Sale

Great Ranch well sited on level almost half acre yard, large living room with fireplace, kitchen and dining room overlooking back yard and deck, 2 bedrooms and 1 full bath, oversized back deck overlooking a small seasonal brook, private PHOTOS next week

555 Middle Road Tpke, Woodbury

$595,000

3 Beds ⋅ 3 Baths ⋅ 24217173 MLS

Step into timeless charm with this classic 1800 New England Colonial in historic Woodbury. Thoughtfully curated wallcoverings weave subtle, boutique elegance and modern personality throughout. The main level offers a bright kitchen with under-cabinet lighting and tiled backsplash, plus space to eat in or host just steps away in the formal dining room. Conveniently situated in the kitchen is a stylishly remodeled half bath featuring marble tile floors. Unwind in the large living room complete with fireplace and built-in bookshelves, or retreat to the freshly remodeled den or home office perfectly positioned off the living and dining rooms. A cozy screened-in porch completes the level. The second floor hosts three bedrooms and two full bathrooms, highlighted by an available ensuite primary retreat. Above, a fully finished, heated third-floor attic offers versatile bonus space with hardwood floors-ideal for a dedicated workout room, play room, or guest suite. Head to the attached two-car garage through a sunlit mudroom, which opens directly to the private back patio and flat, fenced-in backyard. Enjoy unbeatable village convenience with town sidewalk access leading directly to grocery stores, the post office, great restaurants, and the library. A perfect blend of antique character and modern everyday living.

36 Main St S, Woodbury

$375,000

3 Beds ⋅ 1 Baths ⋅ 24215409 MLS

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 boxes! Nestled along a quiet, country road, this meticulously maintained 3 bedroom ranch offers the perfect blend of comfort, convenience, and a picturesque setting. Pride of ownership shines throughout, featuring hardwood flooring, a bright and inviting interior, a spacious kitchen with white cabinetry and stainless steel appliances along with access to a newer deck, perfect for outdoor dining, entertaining, or enjoying your morning coffee. The expansive, backyard features mature trees, perennial gardens, & professionally landscaped grounds. A 1 car garage with attic storage and 3 additional sheds on the property offer plenty of space for tools, equipment, and seasonal items. Enjoy peace of mind with significant improvements including a BRAND NEW septic system, newer heating and cooling systems, roof, and water filtration system. Lovingly cared for and thoughtfully updated, this Woodbury home is ready for it's next chapter!

36 Atwood Rd, Woodbury

$649,900

4 Beds ⋅ 4 Baths ⋅ 24213335 MLS

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 bedrooms, 2 full baths, 2 half baths, a fully remodeled basement, central air, and a 2-car garage with low taxes! Some of the recent updates include a new roof, windows, doors, and mechanicals. Enjoy peaceful pond views from the screened-in porch. This exceptional property is waiting for its new owner!

67 Flanders Rd, Woodbury

$529,000

3 Beds ⋅ 2 Baths ⋅ 24210084 MLS

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 fireplace, built ins as well as oak flooring. It also features a French door to the rear porch overlooking the spacious rear yard. Located adjacent to the kitchen, the formal dining room features a built-in china closet and oak flooring. A powder room and laundry area complete the main level. Upstairs, a front to back primary bedroom with oak flooring. There are two bedrooms and a full bath on this level. Need more room? The walk-up attic is floored provides the opportunity for future expansion. There is a rec room on the lower level for additional space.

11 Judson Ave, Woodbury

$699,900

3 Beds ⋅ 2 Baths ⋅ 24211238 MLS

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 layout features a gorgeous new kitchen with center island opening to a spacious family and dining area with plenty of room for larger gatherings. No detail was overlooked in the renovation. All three bedrooms feature hardwood floors, while the home also offers a new full bath, new laundry room, and a private side deck just off the entry. The finished lower level provides valuable additional living space for a family room, home office, exercise area, or recreation room. A rare opportunity to own a like-new ranch-style home in Woodbury with nothing left to do but move in and enjoy.

1217 Main St N, Woodbury

$1,149,000

3 Beds ⋅ 3 Baths ⋅ 24209744 MLS

Private Litchfield County Retreat on Nearly 10 Acres Tucked among the picturesque hills of Litchfield County, along the desirable Woodbury/Roxbury line, this distinctive Colonial-Contemporary residence offers an exceptional combination of privacy, natural beauty, and modern comfort on nearly 10 acres. Surrounded by mature trees, lush landscaping, and vibrant plantings, the property enjoys a peaceful, secluded setting with the gentle sounds of Transylvania Brook flowing just beyond the backyard. A long, paved, beautifully illuminated driveway leads to the home, where an impressive double-door entrance welcomes you into a spacious foyer featuring a unique indoor water feature. The thoughtfully designed interior offers three generously sized bedrooms, two-and-a-half beautifully renovated bathrooms with luxurious Italian marble tile, and recessed lighting throughout. The inviting lower-level family room opens through French doors to an expansive stone patio and a heated, inground Gunite swimming pool, creating an ideal setting for relaxing or entertaining. A bright four-season sunroom captures sweeping views of the surrounding landscape, while a dedicated office provides a comfortable and private work-from-home space. The spacious primary suite is a true retreat, featuring a walk-in closet, Jacuzzi tub, private balcony overlooking the pool, and a versatile bonus room that can be customized as a reading room, home gym, nursery, or additional living space. Additional fe

24 Roxbury Rd, Woodbury

$550,000

3 Beds ⋅ 3 Baths ⋅ 24210602 MLS

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 WITH BRICK FIREPLACE- MAIN FLOOR OFFICE OR WORKOUT RM- 3 HUGE BEDROOMS WITH THE PRIMARY HAVING IT'S OWN BRICK FIREPLACE, FULL BATH WITH JACUZZI TUB & WALK IN CLOSET- 2.5 BATHS- 2 CAR GARAGE WITH AN ADDIOTIONAL GARAGE IN THE BASEMENT- NEWER ROOF & WINDOWS IN 2012- BEAUTIFUL WOOD FLOORS THROUGHOUT- LARGE DECK-

164 Quanopaug Trl, Woodbury

$2,149,900

5 Beds ⋅ 5 Baths ⋅ 24209591 MLS

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 designed living space. Multiple bedroom suites and an open floor plan provide room for everyone, with inviting spaces for both everyday living and entertaining. The beautiful kitchen opens to a covered porch overlooking an expansive patio and gunite pool, creating a seamless connection between indoor and outdoor gatherings. Car enthusiasts will appreciate the remarkable garage and barn space. An attached, heated three-car garage is complemented by a lower-level garage with room for several additional vehicles. An impressive detached barn, constructed with steel and concrete, accommodates another six to eight cars and features heat, a half bath, glass garage doors, and both upper- and lower-level access. Outside, meticulous landscaping and a paved driveway enhance the setting, while a spacious front patio provides the perfect spot to enjoy the sunsets. An open meadow offers room for outdoor celebrations or potential equestrian use. With its generous living spaces, exceptional vehicle storage, and beautifully maintained grounds, this distinctive property offers far more than the ordinary.

348 Weekeepeemee Rd, Woodbury

$950,000

6 Beds ⋅ 4 Baths ⋅ 24209295 MLS

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 breathtaking views. Set against a backdrop of rolling hills, with gorgeous sunsets - where every season brings a beautiful new view. Step inside and you'll be greeted by expansive LR/Great RM featuring soaring cathedral ceilings, freshly painted walls, and an abundance of natural light. Kitchen is appointed with granite countertops, SS appliances, double pantries, double sinks and a wine chiller making it functional and inviting. Rich Brazilian Cherry HW floors add warmth and elegance throughout the first floor. The first floor primary suite offers a peaceful retreat of its own, highlighted by a claw-foot soaking tub to relax while taking in the views. Upstairs, three additional bedrooms, along with a renovated full bathroom featuring marble walk-in shower and marble countertops. A cozy area(den) for family time and dedicated office space. Lets not forget the bonus living space above the garage. This separate entrance living space includes two-bedroom, kitchen, LR, laundry and garage space. The possibilities for extended family, guests, au pair, rental income or Airbnb option are endless.

92 Quail Run Rd, Woodbury

$875,000

3 Beds ⋅ 3 Baths ⋅ 24209527 MLS

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 setting with a picturesque waterfall nearby, yet is within walking distance to an amazing collection of local favorites, including fine restaurants, diners, a brewery, pub with live entertainment, and French bakery. No wonder they call it "Food-bury!" A stone path leads to a beautiful stone landing and a home filled with warmth and character. The spacious L-shaped living room offers two inviting gathering areas-one centered around a wood-burning fireplace with room for a grand piano, and the other warmed by a woodstove beside a full-wall library and second seating area. Just beyond is a sun-filled, beamed room wrapped in windows on three sides, perfect for breakfast, reading, art, TV, or simply enjoying the view. The charming country kitchen is exceptionally appointed with premium Viking, Miele, Sub-Zero, Dacor and Fisher & Paykel appliances, including an induction cooktop, wall and speed ovens, warming drawer and 2-drawer dishwasher. Thoughtful details include Waterworks fixtures, a pot filler, custom pull-out cabinetry and under-cabinet lighting. Two staircases lead to three restful bedrooms and two beautifully renovated full baths. The primary bath features a Waterworks vanity with quartz top and Waterworks hardware, while the second bath creates a spa-like retreat with a soaking tub and steam shower.

2 Pomperaug Rd, Woodbury

$849,900

4 Beds ⋅ 2 Baths ⋅ 24208978 MLS

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 Main St N is an 1850 antique home with a 2002 addition, offering 4 bedrooms, 2 updated bathrooms and 2,662 square feet of delight on 0.36 acres. It has the historic character people expect from Main Street - mahogany-floored wrap-around porch, oak floors, built-ins and fireplaces - while also having an open kitchen/dining/family-room layout, gas log fireplace, first-floor bedroom, updated bath and attached garage. The backyard should be another major focus. It has beautiful stone walls, an outdoor fireplace, new 43" outdoor gas grill, hot tub, irrigation system and a completely flat yard with room for entertaining and potentially a future pool.

63 Main St N, Woodbury

$550,000

3 Beds ⋅ 2 Baths ⋅ 24206868 MLS

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 convenience, with easy access to shopping, dining, and everyday amenities. The home has been freshly painted, meticulously maintained, and reflects pride of ownership throughout. Inside, you'll find a spacious and inviting floor plan featuring hardwood flooring in the living room and all three bedrooms, adding warmth and character to the main living spaces. The kitchen and pantry are finished with durable vinyl flooring, providing easy care and everyday practicality. The generously sized kitchen features ample counter space, a pantry, a cozy eating area, and a gas fireplace, making it an ideal gathering place for family and friends. The living room is enhanced by built-in bookcases, while the bedrooms offer hardwood floors and built-in desks, combining charm with functionality. The primary bedroom includes a private full bath, creating a comfortable retreat. Additional highlights include a lower-level room, a workshop with walkout access, a tandem garage with room for vehicles and storage, and a fully insulated walk-up attic offering exciting possibilities for future expansion, hobbies, or additional storage. If you're looking for a solidly constructed home with acreage, character, and room to grow, this property presents a rare opportunity to enjoy country-style tranquility without sacrificing convenien

578 Old Sherman Hill Rd, Woodbury

$800,000

4 Beds ⋅ 3 Baths ⋅ 24208716 MLS

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-bedroom, 3-bath home offers an incredible combination of space, privacy, and outdoor living. Surrounded by beautiful natural scenery, the expansive property provides plenty of room to spread out, explore, garden, entertain, or simply enjoy the peaceful setting. Spend warm summer days relaxing by the pool, host gatherings with family and friends, or unwind and take in the privacy of your own country retreat. Inside, the home offers a comfortable and inviting layout with three bedrooms and three full baths, providing plenty of space for everyday living and guests. But the lifestyle extends well beyond the walls-with nearly 10 acres and your own pool, there's plenty of opportunity to enjoy the property throughout the seasons. Located in the charming town of Woodbury, known for its quintessential New England character, historic appeal, local shops, restaurants, and picturesque countryside, this home offers a wonderful balance of privacy and convenience. If you've been dreaming of more land, more privacy, and a place where home feels like a getaway, 69 Nonnewaug Road is one you won't want to miss!

69 Nonnewaug Rd, Woodbury

$599,900

3 Beds ⋅ 2 Baths ⋅ 24207451 MLS

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 period character, the home features beautiful chestnut plank flooring, nearly 9-foot ceilings, and an original fireplace with a beehive oven. The first floor offers a study, living room, dining room, granite-countered kitchen, and a charming breakfast room with wood stove and half bath. Upstairs are three bedrooms, a full bath with marble counter, and conveniently located laundry. A full walk-up attic leads to a large finished space with additional storage and closet space. An attached shed provides a potting area and stairs to a second-floor loft. Set on 3.09 acres, the property also includes a historic barn with a two-car garage, two horse stalls, and a full second floor. Open field and wooded areas create a peaceful country setting, with elevated views toward the town of Woodbury from the upper portion of the property. Across the road, enjoy seasonal views of the Weekeepeemee River, adding to the charm and character of this special historic property.

10 Weekeepeemee Rd, Woodbury

$555,000

5 Beds ⋅ 3 Baths ⋅ 24206024 MLS

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. Boasting wood flooring and newer windows throughout, the main level features a spacious living room, formal dining room, an eat-in kitchen, a cozy family room with fireplace, a private home office, and a full bathroom. Upstairs, you'll find five sizable bedrooms, including a primary suite complete with a walk-in closet and en-suite bath. The remaining four bedrooms share a large full bathroom equipped with a double vanity. The expansive walk-out lower level adds incredible value with over 1,000 square feet of finished, heated living space. It includes a den with fireplace, a possible game room or in-law suite as light streams through a large picture window with views of the backyard. This finished area includes an additional guest room and half-bath. Outside, a circular driveway frames the property amidst mature, private landscaping, while the back deck is primed for summer grilling. Complete with an oversized two-car garage featuring a dedicated work area and abundant storage closets. Bring your design ideas and unlock this gem's full potential.

33 Hurds Hill Rd, Woodbury

$519,000

3 Beds ⋅ 2 Baths ⋅ 24203287 MLS

CHARM, CHARACTER & CLASSIC NEW ENGLAND APPEAL IN HISTORIC WOODBURY! Welcome to this distinctive 1895 Colonial farmhouse, where timeless architectural character blends beautifully with thoughtful modern updates. Offering 3 bedrooms and 1.5 baths, this inviting home is filled with warmth, natural light, and the craftsmanship that makes an older New England home so special. Step inside to discover beautiful hardwood floors, oversized windows, and comfortable living spaces designed for both everyday enjoyment and entertaining. The spacious living room provides an inviting place to gather, while the formal dining room is ready for holiday dinners, celebrations, and memorable evenings with family and friends. The updated kitchen brings modern convenience to the home's historic character with granite countertops and engineered wood flooring. An adjoining eat-in area with a woodstove that heats up to 2200 gross living area and vaulted ceiling creates an open, airy atmosphere and a wonderful place to enjoy morning coffee or casual meals. A convenient half bath completes the main level. Upstairs are three generously sized bedrooms and a full bath, providing plenty of room for a variety of living arrangements. Outside, enjoy the charm of the home's welcoming front porch, or head to the backyard where you'll find space for outdoor entertaining, gardening, recreation, or simply relaxing and enjoying your surroundings.

50 Washington Rd, Woodbury

$679,900

3 Beds ⋅ 3 Baths ⋅ 24204212 MLS

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 entertaining family and friends in this beautiful and private setting.Situated on 2.31 acres, this charming 3/4-bedroom, 2.5-bath Cape/Colonial offers the perfect combination of classic New England character, comfortable living space, and a flexible floor plan. At the heart of the home is the spacious eat-in kitchen, offering plenty of counter and cabinet space and flowing naturally into the inviting family room with a cozy fireplace. Whether you're entertaining a crowd or enjoying a quiet evening at home, this warm and welcoming space is made for gathering.A separate living room and office/den provide additional options for relaxing, working from home, or creating a space that fits your lifestyle.Upstairs, the spacious primary suite is a true retreat with a large closet and private full bath featuring a spa tub and separate shower. Two additional generously sized bedrooms share another well-appointed full bathroom.Need even more room? The finished third floor offers wonderful flexibility and can easily become a fourth bedroom, private home office. Hardwood floors throughout add timeless appeal, while a new roof offers peace of mind.Outside, the 2.31-acre private lot and beautiful pond views create a setting that feels removed from it all, while still being conveniently located near amenities, and major highways

201 Transylvania Rd, Woodbury

$675,000

3 Beds ⋅ 3 Baths ⋅ 24200785 MLS

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 driveway that opens to a circular drive and generous garage parking, a gracious arrival that feels worlds away. Inside, the floor plan delivers more than expected: a sunlit living room, formal dining room, updated white kitchen with breakfast space, and a generous family room anchored by a dramatic stone fireplace. Upstairs are three bedrooms and two full baths, while the finished walkout lower level adds a recreation room, flex room, and dedicated laundry space that can shift with the way you live. The outdoor experience is equally considered, with three distinct places to gather: a welcoming front patio, elevated rear deck, and lower-level patio leading toward the in-ground pool. Framed by bluestone, open lawn, and mature woods, the pool feels less like an amenity and more like a private summer destination. Yet this retreat is only minutes from Woodbury's Main Street celebrated for its restaurants, local shops, and antiques and close to trails and open space at Minortown Road Preserve and Orenaug Park. Private without being remote, flexible without feeling ordinary, this is a home designed for quiet mornings, effortless entertaining, and unforgettable weekends.

61 Minortown Rd, Woodbury

$420,000

4 Beds ⋅ 2 Baths ⋅ 24203216 MLS

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 backsplash, stainless-steel appliances, and a ceramic kitchen floor. Solid pine doors throughout the home add warmth and character. The upstairs bathroom has been beautifully updated, including the tub and a solid-rock vanity countertop. The upper bedroom/closet offers flexible use and can easily be converted back to a bedroom. Additional improvements include updated closet systems, a refreshed closet near the upstairs bathroom, and a roof installed in 2011. The home is generator-ready, with the generator located outside. Enjoy the tranquility of the property while remaining just minutes from Main Street, shopping, and New Morning Market. Nearby schools and everyday conveniences make this a wonderful place to call home.

34 Pilgrim Trl, Woodbury

$875,000

4 Beds ⋅ 3 Baths ⋅ 24202477 MLS

Set on 3.29 picturesque acres bordering conservation land, this beautifully maintained and thoughtfully remodeled country Cape is filled with character, custom craftsmanship and modern amenities. The estate-like grounds and versatile floor plan offer privacy, comfort and functionality, including options for multigenerational living. At the heart of the home, the custom country kitchen features granite countertops, a farmhouse sink, stainless steel appliances and handcrafted cabinetry, opening to a sun-filled sitting/living room with a propane fireplace/stove. The generously sized dining room has its own fireplace, distinctive checkerboard wood floors and a bay window, with the versatility to serve as another living area if desired. The main level includes a primary bedroom with private full bath, a second bedroom, remodeled powder room and separate office or craft room. At the rear, the mudroom incorporates laundry and antique chestnut cabinetry, one of the many details that give this home its individual character. Upstairs are two spacious bedrooms, an updated full bath, built-in storage and a large walk-in attic with the potential for future finished space. The walk-out finished lower level adds another dimension to the home, with a fireplace and antique reclaimed pine cupboards and built-ins. This comfortable area lends itself to recreation, a home office or simply relaxing. A substantial unfinished basement provides abundant storage. The grounds are equally impressive.

385 Middle Road Tpke, Woodbury

$1,100,000

4 Beds ⋅ 5 Baths ⋅ 24202077 MLS

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 relaxed, filled with color and thoughtful character. The beautifully crafted floor plan offers intimate parlors, three fireplaces, a generous kitchen, spacious living and dining areas made for gathering, charming Dutch doors, a cozy den, well-proportioned bedrooms, and an exceptional laundry room conveniently located on the same level as the recreation room with its own fireplace. Outdoors, a pool, professionally designed gardens, a growing room, and welcoming terraces create a setting to be enjoyed for generations. Every detail reflects a deep understanding of what makes a house feel like home. This seller is motivated!

90 Sage Rd, Woodbury

$574,900

3 Beds ⋅ 3 Baths ⋅ 24200605 MLS

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 possibilities give you room to make it your own. The first floor offers a wonderful layout with a comfortable living room, spacious great room, and separate dining room, creating plenty of flexibility for everyday living and entertaining. The kitchen has been thoughtfully updated, from the main living spaces, step outside onto the deck - a natural extension of the home for relaxing, dining, or enjoying the outdoors. Upstairs, you'll find generously sized bedrooms with the space and comfort today's buyers are looking for. But the real surprise is downstairs. The walk-out lower level offers even more usable space, including a large room currently used as a workout area and another area that can serve as storage, recreation space, or additional living space. Step outside to the screened-in deck, adding another terrific spot to enjoy the property. And for those looking for flexibility, the large lower-level room has its own separate entrance and offers intriguing potential to create a private studio or guest suite with the addition of a kitchen and bathroom. Whether you envision a home office, gym, creative studio, guest quarters, or future additional living space, the possibilities are here. Turn-key, versatile, and full of potential - this is a home that can adapt to the way you live. Come see!

323 Upper Grassy Hill, Woodbury

$799,900

5 Beds ⋅ 4 Baths ⋅ 24200842 MLS

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 an unheard of $197. per! Bring on the big multi-generational family! Natural sun filtered house has front and back staircases, large rooms, 9'ceilings, and mostly hardwood. Granite kitchen/ great room open to breakfast nook, family room w fireplace and french doors to rear decking. Formal dining room and living room are a must in this classic style. The entertaining space is oversized so host all the holiday gatherings with ease. Primary suite is HUGE, walk in plus another closet and luxury bath. 3 additional bedrooms and an office. A separate 2nd floor laundry room, also very generous in size. Very level usable yard with a large area off the back deck fenced for dogs. (used to have a pool). Brand new central AC unit, refinished hardwood and fresh paint on the main level. In-law apartment is propane heat/ac

132 Good Hill Rd, Woodbury

$1,600,000

4 Beds ⋅ 3 Baths ⋅ 24199540 MLS

Turnkey Equestrian Facility on 21 Acres. A rare opportunity to own a fully operational equestrian property offering the perfect blend of functionality, comfort, and income potential. Set on 21 acres, this established working horse boarding facility features 21 stalls, a heated indoor riding arena with viewing area, heated tack rooms, two wash stalls, private storage lockers, two outdoor riding arenas, and newer RAM fencing throughout the property. The spacious 4-bedroom Colonial offers comfortable living with a primary suite featuring its own fireplace, two additional fireplaces with woodstoves, and a screened-in porch overlooking the property. The home provides plenty of space for both everyday living and entertaining. Adding even more versatility is the 2-bedroom apartment above the garage, ideal for a barn manager or helper, guest accommodations, or additional rental income. Whether you're looking to continue the existing boarding operation, create your own private equestrian retreat, or take advantage of the property's multiple income-producing possibilities, this exceptional horse property is ready to welcome its next owner. Agent owner.

138 Minortown Rd, Woodbury

$649,900

4 Beds ⋅ 2 Baths ⋅ 24194243 MLS

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 expansive lawn, the home features hardwood floors throughout, high ceilings, detailed moldings, interior French doors, charming built-ins, a generous foyer, and a graceful central staircase. The front-to-back living room is anchored by a brick fireplace and opens to a spacious covered porch, creating an inviting setting for everyday living and entertaining. The kitchen and both bathrooms have been updated, blending modern convenience with the home's original character. A beautiful 34' x 27' post-and-beam barn provides exceptional space for a workshop, studio, storage, or other uses. Located within Woodbury's Main Street Design District, the property also offers the flexibility to combine residential living with a business use, subject to applicable regulations. A distinctive property with room to live, work, and enjoy the best of classic Woodbury.

126 Main St N, Woodbury

$749,900

6 Beds ⋅ 4 Baths ⋅ 24187148 MLS

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 with 6 bedrooms, 4 full bathrooms, and an oversized heated 3-car garage. A welcoming 12' x 9' slate-floor foyer introduces the home and leads to generously proportioned living spaces designed for both everyday comfort and entertaining. The oversized formal dining room provides an impressive setting for large gatherings, while the well-appointed kitchen features granite countertops, a casual eat-in area, double Viking ovens, a Viking 6-burner cooktop, and Miele dishwasher. Two fireplaces add warmth and character throughout the home, while a whole-house sound system enhances both indoor and outdoor entertaining. The expansive 37' x 23' heated three-car garage offers abundant room for vehicles, storage, hobbies, or workshop space, feel secure with a whole house generator. Outdoors, enjoy a large slate patio entertainment area complete with a wood-fired grill, overlooking a spacious, level yard with plenty of room for recreation and gatherings. With six bedrooms, expansive living areas, quality amenities, and the convenience of true one-level living, this distinctive Woodbury property offers an exceptional combination of space, comfort, and versatility.

24 Scuppo Rd, Woodbury

$499,900

3 Beds ⋅ 2 Baths ⋅ 24194640 MLS

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 level includes 3 bedrooms, a full bath, and access to a walk-up attic from the primary bedroom. The main level offers a half bath and a functional, open layout. Additional property highlights include a separate 962 sq. ft., 2-bedroom guest house-offering incredible potential for an in-law suite or rental income once renovated (appears to be separately metered). The property also features two massive, 2-story barns that appear to have electricity. Tremendous upside potential for an end-user, investor, or multi-generational living. Subject to probate approval. Property sold as-is; no disclosures.

153 Old Sherman Hill Rd, Woodbury

$959,000

4 Beds ⋅ 3 Baths ⋅ 24188039 MLS

Timeless Elegance & Immaculate Detail. Welcome to The Naramore House, a piece of living history. Lovingly preserved since 1898, this pristine colonial home seamlessly blends grand historic character with immaculate, turnkey maintenance. A classic wraparound front porch invites you through a charming dutch door into a formal, stately foyer featuring high ceilings and original pocket doors. The massive living room serves as the heart of the home, offering incredible square footage for multiple seating arrangements, media setups, and a cozy fireplace. Host effortlessly in the grand formal dining room and eat-in kitchen, complete with a generous pantry, a charming secondary rear staircase, and screened in sun porch. A luxurious primary retreat featuring a fireplace, private en-suite bath and massive 10x7 foot closet/dressing room. Three additional bright and spacious bedrooms include a versatile room-ideal for a dedicated home office, nursery, or library. The home has a huge attic with potential for expansion. A private patio, stunning formal garden with pagoda and mature trees offer the perfect setting for outdoor enjoyment. A recently renovated barn includes new structural beans and flooring. This lovely home offers in town conveniences like walking to restaurants, shops and local parades while set off of Main Street. Enjoy the beautiful historic architecture with the peace of mind that comes from a property that has been meticulously cared for inside and out.

11 Pleasant St, Woodbury

$1,278,000

3 Beds ⋅ 3 Baths ⋅ 24192284 MLS

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 home boasts original wide-plank wood floors, dual fireplaces, twin staircases, authentic built-ins, and freshly renovated baths. At its heart is the kitchen featuring Viking appliances and granite counters that open to garden views. Step through the screened stone-and-timber breezeway to a newly expanded patio and custom firepit crafted directly from native fieldstone, all beneath a classic wood-shingle and copper roof. The surrounding grounds function as a true New England compound. A separate two-bedroom carriage house offers built-in guest quarters with a covered porch and an oversized 2.5-car garage. Nearby, a newer two-story 40'x28' barn provides flexible space for a creative studio, vehicle storage, or livestock, complemented by two additional storage sheds. Recent improvements include, but are not limited to, a new cedar-shingle roof with copper downspouts (2025), new A/C, fresh interior paint throughout (2026), and refinished flooring. It is an unmistakable rural sanctuary with abundant room for hosting friends and extended family.

509 Weekeepeemee Rd, Woodbury

$1,100,000

4 Beds ⋅ 4 Baths ⋅ 24192457 MLS

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 suite or au pair quarters. The main level features wood floors, formal living and dining rooms, an eat-in kitchen, a bedroom, a full bath, and a family room with a fireplace that opens to an oversized deck. Upstairs, you'll find three bedrooms, a full bath, and a spacious primary suite with a spa-like bath and loft area. The walk-out lower level includes three finished rooms plus a full bath, offering flexible space for guests, extended living, recreation, or work-from-home needs. The private backyard is surrounded by trees and accented with perennial gardens. NEW Roof June 2026. Located in Woodbury-one of Connecticut's most beloved small towns-the home is close to charming shops, antique stores, coffee shops, and restaurants, all just about 90 minutes from New York City.

16 Gate Post Ln, Woodbury

$599,900

4 Beds ⋅ 3 Baths ⋅ 24192145 MLS

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 seasonal long views, this 2,972 sq. ft. contemporary offers an outstanding combination of acreage, privacy, and potential rarely found at this price point. Designed for comfortable living, the home features a dramatic sunken living room with soaring vaulted ceilings, a fireplace, and walls of windows overlooking the surrounding landscape. The main level includes a spacious primary suite, private office, butler's pantry, and access to expansive decks that invite outdoor entertaining. Upstairs are 3 additional bedrooms and an open den, while the unfinished walk-out lower level offers endless possibilities for future living space. The property's 12.69 acres provide a beautiful backdrop with open land, mature trees, and a four-stall barn, offering flexibility for a variety of country lifestyles. Priced to reflect the opportunity for renovation and updating, this is an exceptional chance for investors, builders, or buyers looking to customize a solidly built home in one of Woodbury's most desirable locations. With great bones, an outstanding setting, and significant upside potential, this property is ready for its next chapter. Sold as is.

348 Hoop Pole Hill Rd, Woodbury

$895,000

4 Beds ⋅ 3 Baths ⋅ 24172964 MLS

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! 2 homes IN CONTRACT, 1 home available for FALL DELIVERY and this new build to start in later summer/early fall for SPRING DELIVERY 2027. Owner/Agent/Builder.

96 Quail Run Rd, Woodbury

$384,900

3 Beds ⋅ 3 Baths ⋅ 24099709 MLS

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 with endless potential. This home includes hardwood floors throughout. A dedicated home office with custom built-in shelving. Large living room with pellet stove and a spacious mudroom with vaulted ceilings, laundry hookups, and a large walk-in pantry. The property sits on 1.5 acres, complete with an in-ground pool and safety fence. Whether you're looking to restore its original charm or add your own personal touches, this home presents an excellent opportunity to build equity in one of Litchfield County's most sought-after communities. New windows, siding and gutters in 2024. The property is being sold "AS IS." PRICED TO SELL!!

241 Hoop Pole Hill Rd, Woodbury

$1,590,000

4 Beds ⋅ 3 Baths ⋅ 24184948 MLS

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 cabinetry, butler's pantry, soapstone counters, and a Vulcan stove, all centered around a brick fireplace flanked by double French doors leading to a shady brick patio. Off the kitchen, a spacious screened porch surrounded with stone walls, offers a peaceful spot to enjoy the seasons. The formal living room, currently an office, boasts a light-filled five-window bay, while two front entry rooms serve as a den and library. The primary suite, in its own wing above the great room, features a private living room, full bath, sleeping area, and views of Perkins Ponds. Three additional bedrooms, accessed via a second staircase, are bright, charming, and surprisingly well-appointed with closets. The impressive barn offers tandem bays for vehicles, a heated workshop, and two upper rooms perfect for future studio spaces. Relax by the pool, take in the flowers, and enjoy the chorus of birds. POTENTIAL FOR ADDITIONAL TWO LOTS SPLIT OFF OR SECONDARY HOME TO BE BUILT. BUYERS MUST DO THEIR OWN DUE DILIGENCE.

40 Ruffin Rd, Woodbury

$775,000

3 Beds ⋅ 2 Baths ⋅ 24182784 MLS

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 anyone seeking a peaceful rural lifestyle. The horse facilities include 4 barns with a total of 10 stalls, 2 wash stalls, and a 20 x 60-meter riding arena with premium stone dust and sand footing. The grounds offer ample space for turnout, training, recreation, and relaxation, creating the perfect balance of functionality and tranquility. At the heart of the property is a charming 3-bedroom, 2-bath ranch home featuring a windowed kitchen, spacious dining room for entertaining, vaulted ceilings, 2 fireplaces with wood stoves, a WIC, and an oversized lower-level bonus room. Step outside to a private backyard designed for gatherings and enjoyment, complete with a thriving vegetable garden. The 1 BR apartment is currently rented, but can easily serve as an in-law suite or guest quarters. There is also a 3 car garage for the car enthusiast! The possibilities are endless! The present owners, Serenity Farm Horse Rescue, have lovingly cared for this property for years. As their rescue continues to grow, they are seeking a larger facility to support their expansion. Shown by private appt.

92 Minortown Rd, Woodbury

$780,000

4 Beds ⋅ 2 Baths ⋅ 24183601 MLS

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' accessory building with heat - great guest house or in-law potential. Inspired by Tuscan villas, Italianate style homes, usually square and symmetrical, were popular in the late 19th C. in New England. Park-like grounds; large pond has goldfish (see pics). The 3532 square foot main home has potential for an in-home business, or retail shop as it once was. Other potential uses in this highly-visible location include using the barn for farm animals and/or horses. Home has 4 bedrooms, 2 full bathrooms, 3 fireplaces, and approx 435 sq foot foot, renovated, eat-in, sunny kitchen with leathered granite counters and stainless appliances. New oil furnace 2026. Septic recently maintained (new pump, piping, and floats in 2022 by Garrity, no problems since). 50 gallon water heater Oct 2022. Substantial moldings and built-ins, front and back staircases, specialty stainless skylights, and a rooftop belvedere, which looks beautiful lit up at night, atop the well maintained copper roof. Minutes to three towns centers of Woodbury, Watertown, and Bethlehem. Guesthouse has elec.

1917 Main St N, Woodbury

$2,995,000

4 Beds ⋅ 6 Baths ⋅ 24163576 MLS

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 two-car garage, pool cabana and pool equipment building. A newly constructed temperature controlled 3,800-square-foot post-and-beam barn with a half bath and laundry room at the rear of the property further expand the property's possibilities. There are also an equipment/horse barn and riverside cabin. Outdoor living is equally remarkable with a stunning new in-ground gunite pool surrounded by lush landscaping. Designed for both relaxation and entertaining, the grounds include a custom "summer kitchen" with a European-style outdoor pizza oven, gas grill, and screened dining pavilion-perfect for hosting gatherings or enjoying quiet evenings. The 18.3-acre setting includes mature trees, open meadows, scenic walking trails, and frontage along the protected Pomperaug River, creating a private and picturesque retreat. Rich in history yet thoughtfully updated, this rare estate offers an exceptional combination of beauty, functionality, and enduring charm. A comprehensive list of recent improvements is available upon request. Buyer must do due diligence with the town for possible uses.

920 Main St S, Woodbury

$749,900

4 Beds ⋅ 4 Baths ⋅ 24138386 MLS

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 where you can enjoy the Library, antique and retail shops, schools, churches, great restaurants and coffee shops. Parks and the Senior Center are all nearby. Only 90 minutes to NYC. Named by Reader's Digest as one of CT most charming towns. Come call Woodbury home!

28 School St, Woodbury

$895,000

4 Beds ⋅ 3 Baths ⋅ 24172742 MLS

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 designed for both intimacy and entertaining. A cozy sitting room and a dedicated office/library-complete with a classic fireplace-offer quiet retreats. For larger gatherings, the front-to-back living room, with windows on three sides, is bathed in natural light. At the heart of the home is the remodeled kitchen, which opens to the dining room centered around the original refurbished center core fireplace. Upstairs, four bedrooms await. The primary bedroom offers a new ensuite bath detailed with custom tile. The three additional bedrooms share a fully renovated bathroom with a soaking tub/shower combo. Thoughtfully curated, professionally designed interior furniture and fixtures are available upon request. The property has benefited from extensive renovations that include new bathrooms and kitchen, floor refinishing, a new well, upgraded septic, and more; a substantial list is available upon request.

253 Bacon Pond Rd, Woodbury

$645,000

3 Beds ⋅ 3 Baths ⋅ 24165212 MLS

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, 2.5 BA FARMHOUSE STYLE SPLIT LEVEL with large front porch, oversized 2 car garage, CATHEDRAL LIVING ROOM and finished lower level with laundry room and half bath.

94 Quail Run Rd, Woodbury

$1,395,000

5 Beds ⋅ 5 Baths ⋅ 24168618 MLS

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 preservation and character, having been featured in Early American Life magazine and Historic Homes magazine-an honor that speaks to its authenticity and enduring appeal. This stately five bedroom home showcases original architectural details that collectors and history enthusiasts dream about. Seven fireplaces anchor the home's character across its generous 4,800+ square feet. Five beautifully paneled rooms reveal the craftsmanship of a bygone era, while antique wide-board flooring runs throughout, whispering stories of centuries past beneath every footstep.

30 Hollow Rd, Woodbury

$999,900

3 Beds ⋅ 3 Baths ⋅ 24146826 MLS

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 with a cathedral ceiling and fireplace, and formal living and dining rooms, each with its own fireplace. Upstairs, the primary suite boasts a vaulted ceiling with exposed beams, accompanied by two additional bedrooms and a walk-up attic. This will be a brand new house when complete; new mechanicals, new insulation, new wiring, new plumbing, new kitchen and baths - a new home with the charm of old. The exterior could be equally impressive, offering two post-and-beam barns, and a beautifully landscaped level lot. The Middle Quarter zoning adds extra versatility, allowing you to run a business from home and even expand the living space into the barns. This is truly one of the best locations in Woodbury!

27 Middle Quarter Rd, Woodbury

$1,790,000

4 Beds ⋅ 5 Baths ⋅ 24136657 MLS

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. 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 surrounding the impressive central hearth. The chef's kitchen features a large center island, breakfast bar, and sweeping views of the expansive lawn-perfect for both everyday living and entertaining. Original details abound, including hand-hewn beams, wide king's board flooring, and the historic cooking fireplace that anchors the heart of the home. Recent upgrades include a new HVAC system with humidification and numerous other enhancements (see attachments for the full list). A new mahogany deck overlooks the level backyard, leading toward a picturesque bridge, sparkling pool, and inviting cabana. Two barns sit near the parking area-one offering garage space and the other ready for your imagination: ideal for a future guest house, studio, or recreation room, this barn has new propane heat, water and electric service. This extraordinary home offers the rare opportunity to own a piece of history-beautifully updated for modern living.

55 Good Hill Rd, Woodbury

$289,000

2 Beds ⋅ 2 Baths ⋅ 24078648 MLS

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, level, potential building lot. Convert office to residential, build across river and rent out office or use office and workshop yourself. There are 2, 7ft' garage doors leading to basement/workshop. The potential uses for this property are many! Sold As-Is, Where-Is, Buyer to do all due diligence regarding potential uses, Cash or Hard Money Loan preferred, no Seller Financing.

439 Washington Rd, Woodbury

$990,000

3 Beds ⋅ 2 Baths ⋅ 24086595 MLS

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 above Main Street North! Just a few minutes from Woodbury's town center, this home provides an open floor with a kitchen/great room, a cathedral ceiling, and a floor-to-ceiling masonry fireplace. The first floor includes a primary suite and two other bedrooms while the upper level offers an office and a loft, both with a cathedral ceiling and views to the outside.

523 Main St N, Woodbury

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