45 Connecticut Properties

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Contract Signed
Property for Sale at Old Sherman Hill Road, Woodbury, Connecticut - Bedrooms: 4 
Bathrooms: 5 
Rooms: 11  - $2,100,000 Previous PhotoNext Photo

Old Sherman Hill Road
$2,100,000

Woodbury, CT
House
Rooms: 11
Bedrooms: 4
Bathrooms: 5
Web ID: 24072926

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 system, central vac, generator, and 4-bay heated garage. The spectacular grounds include the inground gunite saltwater pool, spacious composite deck, mature professional landscaping, and amazing views of distant hills. For the horses there is a two-story 8 stall stable, 14 paddocks with aisle ways, 120' x 200' riding ring with Atwood Equestrian Surface (re-surfaced 4 years ago), 7 run-in sheds, 20' x 20' tractor barn and trail. Woodbury designated as Connecticut's Most charming small town, by Reader's Digest offers tree-lined Main St, parks, playgrounds, hiking trails...

(203) 253-1800

Painter Hill Road
$1,675,000

Woodbury, CT
House
Rooms: 9
Bedrooms: 4
Bathrooms: 3
Web ID: 24075060

Stunning Renovated Antique Home with Scenic Views & Luxurious Amenities, Discover the perfect blend of historic charm and modern luxury in this totally renovated antique home, and Barn set on 9.44 picturesque acres bordering 20 acres of Land Trust. This home offers 4 bedrooms, 3 full baths, and exquisite craftsmanship throughout. Step inside to find new wide plank floors, recessed lighting, skylights, and a wood-burning fireplace, creating a warm and inviting ambiance. The high-end Chef's Kitchen is a culinary dream, featuring granite countertops, Shaker-style cabinets, and top-of-the-line appliances. The Primary Bathroom boasts a large glass shower, with Waterworks hardware, adding a spa-like retreat to your daily routine. Outside, enjoy the beauty of open meadows, a rushing brook, and a breathtaking perennial garden designed by Pound Ridge Nurseries. Stone outcroppings, specimen trees, and charming stone walls enhance the landscape. A renovated in-ground Gunite pool offers the perfect spot for...

(203) 253-1800

Transylvania Road
$1,275,000

Woodbury, CT
House
Rooms: 10
Bedrooms: 3
Bathrooms: 4.5
Web ID: 24077441

Custom-built. This unique home is made for entertaining. 4000 ft.2 home with 3 bedroom suites each containing its own full bath. 5 Bathrooms. 3 Fireplaces. Chef's kitchen with granite counters, double ovens, bow window w/bench seat & walk out to deck. Formal dining room has tray ceiling. Great room with fireplace and full bar. Den/library has fireplace. Bright piano room/sunroom/office also walks out to deck. All 3 Fireplaces have fans for heat! Allergy free home has a comfort electronic system air cleaner built into furnace. Whole house has hardwood floors. All rooms CAT wired & wired for music. Professional wine cellar. Family room with fireplace and a half bath. French doors onto patio. Beautiful stone wall in back yard has 7 columns with granite tops, light fixtures, 3 Walpole woodworker gates. Heated 3 car garage with Epoxy covered flooring. Home in Superior condition! Surrounded by rolling views & privacy with...

(203) 253-1800
Contract Signed
Property for Sale at Owl Ridge Road, Woodbury, Connecticut - Bedrooms: 4 
Bathrooms: 4.5 
Rooms: 13  - $1,150,000 Previous PhotoNext Photo

Owl Ridge Road
$1,150,000

Woodbury, CT
House
Rooms: 13
Bedrooms: 4
Bathrooms: 4.5
Web ID: 24044196

Welcome to the Owl Ridge neighborhood of Woodbury, this newly renovated 4-bed, 5-bath home is in pristine condition and features a harmonious blend of comfort and space. The heart of the home is the newly renovated kitchen, with natural quartzite countertops, refinished hardwood floors and new stainless steel appliances. The open concept design seamlessly connects the eat-in kitchen to the expansive family room, where a cozy fireplace and cathedral ceilings invites you to relax and unwind. Entertain in the formal living and dining room plus a roomy great room as a separate play room, music or media room. Work from home in the dedicated office with its own half bath. The sunroom works as a play room or art studio complete with sink to wash out your brushes. Upstairs the primary bedroom suite is a private retreat, complete with a sitting room, where you can escape for moments of tranquility....

(203) 253-1800

Middle Quarter Road
$1,150,000

Woodbury, CT
House
Rooms: 8
Bedrooms: 3
Bathrooms: 3
Web ID: 24049803

Discover the charm of this beautifully soon to be restored antique home in the heart of Woodbury! Nestled on the serene Middle Quarter Road, this soon to be renovated vintage gem 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. The exterior is equally impressive, offering room an in-ground gunite pool, 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...

(203) 253-1800

Gate Post Lane
$1,125,000

Woodbury, CT
House
Rooms: 12
Bedrooms: 4
Bathrooms: 4
Web ID: 24039243

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. 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 bath, and a primary suite with a spa-like bath and loft area. The lower level features three finished rooms and a full bath. The private backyard is surrounded by trees and dotted with perennial gardens. Woodbury is one of Connecticut's best small towns filled with charming shops, antiques, coffee shops and restaurants and it's only 90 minutes from NYC

(203) 253-1800
Contract Signed
Property for Sale at Bear Run, Woodbury, Connecticut - Bedrooms: 4 
Bathrooms: 5 
Rooms: 14  - $1,124,000 Previous PhotoNext Photo

Bear Run
$1,124,000

Woodbury, CT
House
Rooms: 14
Bedrooms: 4
Bathrooms: 5
Web ID: 24059188

Tucked away on a sought-after cul-de-sac, this open-layout home is crafted for exceptional entertaining. The light-filled, two-story foyer is framed by two sets of French doors: one opening to an office & the other leading to a living room that flows seamlessly into the dining room-an ideal setup for holiday gatherings. The custom kitchen, equipped with granite countertops, a center island, gas cooktop, walk-in pantry & dining area, overlooks the pool & patio. Adjacent to the kitchen is a sitting room & spacious family room featuring a fireplace & built-in bookcase. A generous 20x35 recreation room further enhances the home's entertainment options with a custom bar, vaulted ceiling, full bath & two sets of sliding doors that open to the pool, spa & patio area, creating a perfect indoor-outdoor experience. The upper level boasts a primary suite with a spacious bath & walk-in closet along with two additional bedrooms connected...

(203) 253-1800

Flanders Road
$975,000

Woodbury, CT
House
Rooms: 8
Bedrooms: 3
Bathrooms: 4
Web ID: 24043622

Come home to a unique 3082 sqft, one of a kind custom built Barn home all set on 5 secluded acres. Featuring an open floor plan, beamed ceilings, oak floors, Plaster Walls, fully applianced Kitchen with breakfast bar, a spacious Family Room with brick fireplace, built-ins, & slider leading to back deck. The Living Room with fireplace is adjacent to a spacious Dining Room area & slider leading to large deck with access to side yard. At the end of the day enjoy the cozy Library with fireplace and built-ins. First floor also has an Office as well as a full Bathroom. As you ascend the stairs to the second floor you will marvel at the unique lighted brick archway. Second floor boasts of lovely Primary Bedroom Suite with brick fireplace & raised hearth, walk-in closets, Full Bath with tub, shower & vanities, and slider leading to balcony. Two other...

(203) 253-1800
Contract Signed
Property for Sale at Birchwood Lane, Woodbury, Connecticut - Bedrooms: 3 
Bathrooms: 3 
Rooms: 9  - $949,000 Previous PhotoNext Photo

Birchwood Lane
$949,000

Woodbury, CT
House
Rooms: 9
Bedrooms: 3
Bathrooms: 3
Web ID: 24057609

Experience the epitome of architectural artistry with this contemporary home, a serene sanctuary that celebrates the fusion of nature and modern design. Perched on 3.4 acres and hidden amongst the trees, this property presents framed views of nature and mossy stone outcroppings. High-end appliances including Gaggenau and JennAir in the kitchen and hi-tech amenities throughout cater to a lifestyle of modern convenience. The primary suite exemplifies contemporary luxury with a pair of wall hung sinks, stall shower, separate w/c and a full swath of built-in closets. The upper bedroom provides an ensuite full bath and private entrance, while the lower bedroom shares its full bath with the great room. Audiophiles will appreciate the integrated surround sound in the great room with easy access to the bar for a chilled beverage or glass of wine. The artist loft/den with its own lookout creates a creative space for inspiration or work from...

(203) 253-1800

Saxony Lane
$899,900

Woodbury, CT
House
Rooms: 6
Bedrooms: 3
Bathrooms: 3.5
Web ID: 24072388

Do not miss this beautiful home set back on a private 4.15-acre lot. Main level features a total open floor plan with vaulted ceilings and half bath. Kitchen features Kucht stainless steel appliances, Quartz countertops, with an oversized walk-in pantry. Extra Large dining, kitchen, family room area with built in sound system perfect for entertaining. Upper level adds 2 large bedrooms along with a laundry room and two full bathrooms. Additional to the 2 bedrooms is the Massive Primary suite with fireplace and sitting area, 2 large walk-in closets and a gorgeous full bath with extra-large shower with dual heads. On top of all that a gigantic 1940 square foot 4 bay garage dual deep that can hold up to 7 cars easily with 3/ 9' garage doors and 1/12' door that has a car lift for that person who likes their toys!! Back patio with hot tub. Tesla solar...

(203) 253-1800
Contract Signed
Property for Sale at Transylvania Road, Woodbury, Connecticut - Bedrooms: 5 
Bathrooms: 4 
Rooms: 10  - $899,000 Previous PhotoNext Photo

Transylvania Road
$899,000

Woodbury, CT
House
Rooms: 10
Bedrooms: 5
Bathrooms: 4
Web ID: 24018837

Nestled at the intersection of Route 72 and Route 167 in Woodbury, this exceptional home is the perfect blend of modern amenities and unparalleled convenience. Located in close proximity to both the Center of Woodbury and the Southbury Green you'll be moments away from a diverse selection of shops and restaurants. Enjoy the close by natural beauty of Wood Lake, local parks, walking trails, and make the most of the nearby Southbury Dog Park. With easy access to exits 13, 14, and 15 off of I-84, as well as route 8, commuting will never be easier. This property is directly next to the entrance of Janie Pierce Park and backs up to over 30 acres of serene land conservation, guaranteeing exceptional privacy and tranquility for years to come. Upon entering, you'll be greeted by an open floor plan that seamlessly combines elegance and functionality. The inviting kitchen features granite countertops,...

(203) 253-1800
Contract Signed
Property for Sale at Fawn Meadow Lane, Woodbury, Connecticut - Bedrooms: 4 
Bathrooms: 4 
Rooms: 8  - $899,000 Previous PhotoNext Photo

Fawn Meadow Lane
$899,000

Woodbury, CT
House
Rooms: 8
Bedrooms: 4
Bathrooms: 4
Web ID: 24075051

Located in the heart of Woodbury, the antiques capital of Connecticut, with convenient access to the charming towns of Litchfield, Washington, and Roxbury, this newly built modern farmhouse offers a perfect balance of comfort and elegance. Thoughtfully designed with quality craftsmanship and energy-efficient features, this inviting retreat boasts 3 spacious bedrooms, 3.5 bathrooms, and a generously sized finished bonus room with its own full bath, providing endless possibilities for a guest suite, home office, or recreation space. Situated on approximately three acres surrounded by peaceful woodlands, the home is an entertainer's dream, featuring an open-concept kitchen, dining, and living area with a warm and inviting gas fireplace. Step outside to discover a beautifully designed outdoor oasis, complete with a pool, lush gardens, and a charming pool house, creating the perfect setting for relaxation and gatherings. Conveniently located near top private schools like Taft and Westover, as well as local farms,...

(203) 253-1800
Contract Signed
Property for Sale at Washington Road, Woodbury, Connecticut - Bedrooms: 3 
Bathrooms: 3 
Rooms: 8  - $885,000 Previous PhotoNext Photo

Washington Road
$885,000

Woodbury, CT
House
Rooms: 8
Bedrooms: 3
Bathrooms: 3
Web ID: 24024970

This recently fully renovated Antique has a combination of historic charm & modern amenities, which creates a truly exceptional living space. The potential for a pool adds an extra touch of luxury, while the delightful & well-maintained two-story barn in ready condition, presents exciting opportunities for conversion, whether for a guest house, pool house, or a private office on the 2nd floor office. Set within a private, park-like setting with picturesque features like a picket fence, stone walls, and professional landscaping, this home offers you a serene escape. The wide board floors and built-ins throughout add character and warmth, while the large foyer with a cedar closet sets a welcoming tone. The first floor is designed for both comfort & functionality, with a living room featuring a fireplace for cozy gatherings, a dining room that flows seamlessly into a charming kitchen equipped with custom cabinetry, marble counters, and stainless steel...

(203) 253-1800
Contract Signed
Property for Sale at Quanopaug Trail, Woodbury, Connecticut - Bedrooms: 4 
Bathrooms: 4 
Rooms: 10  - $879,000 Previous PhotoNext Photo

Quanopaug Trail
$879,000

Woodbury, CT
House
Rooms: 10
Bedrooms: 4
Bathrooms: 4
Web ID: 24076275

Stunning! Dramatically open, spacious, modern colonial offers a perfect balance of comfort and elegance. Thoughtfully designed with quality craftsmanship and energy-efficient features, this inviting retreat boasts 4 spacious bedrooms, 3.5 bathrooms, and a generously sized finished Wow room with its own additional bedroom providing endless possibilities for a guest suite, home office, media room or recreation space. Situated on over two acres surrounded by peaceful woodlands, the home is an entertainer's dream, featuring an open-concept kitchen, dining, and living area with a warm and inviting fireplace. Step outside to discover a beautiful outdoor oasis with fire pit creating the perfect setting for relaxation and gatherings. Conveniently located near top private schools like Taft and Westover, as well as local farms, restaurants, boutique shopping, and outdoor recreation. This exceptional home offers the best of Litchfield County living with convenient access to the charming towns of Litchfield, Washington, and Roxbury. Less than...

(203) 253-1800
Contract Signed
Property for Sale at Main Street, Woodbury, Connecticut - Bedrooms: 3 
Bathrooms: 3 
Rooms: 7  - $849,000 Previous PhotoNext Photo

Main Street
$849,000

Woodbury, CT
House
Rooms: 7
Bedrooms: 3
Bathrooms: 3
Web ID: 24055622

Your home is your castle! If you've ever dreamed of calling a castle your home, this remarkable 5,000-square-foot stone house is the answer. Known fondly by locals as The Castle, this property has a fascinating history, with roots tracing back to the 1800s but the all updates including new mechanicals, plumbing, electric, floors, well, septic, roof and more will give you comfort and peace of mind. Originally a stagecoach stop, it stands near a brook that was once a favored path of the legendary Leatherman. In the 1970s, a visionary known as Cadillac Joe began expanding the home into a grand stone castle, meticulously crafting every stone by hand. Though his work was left incomplete due to his advancing age, the foundation he laid became the start of a stunning transformation. Enter Mario, whose dedication and years of hard work brought the vision to life, completing this architectural masterpiece with...

(203) 253-1800
Contract Signed
Property for Sale at Main Street, Woodbury, Connecticut - Bedrooms: 3 
Bathrooms: 5 
Rooms: 11  - $775,000 Previous PhotoNext Photo

Main Street
$775,000

Woodbury, CT
House
Rooms: 11
Bedrooms: 3
Bathrooms: 5
Web ID: 24074526

Set on 3.5 acres with 150 feet of Pomperaug River frontage, this expanded Cape blends classic charm with thoughtful updates. Featuring 3 bedrooms, 4.5 baths, and multiple living areas, this home is designed for comfort and entertaining. The kitchen has been beautifully updated, featuring leathered granite countertops, stainless steel appliances, and custom cabinetry, making it both stylish and functional. The sunlit family room boasts vaulted ceilings and a cozy window seat, offering a perfect spot to enjoy nature and birdwatch overlooking an expansive mahogany deck. A formal living room with a fireplace and a dining room with its own fireplace create warm, inviting spaces. The first-floor bedroom adds convenience and flexibility. Upstairs, the spacious master suite features a full bath, while a guest suite with a private bath provides extra comfort. . Refinished hardwood floors on the main level enhance the home's character and warmth, new flooring upstairs, and fresh...

(203) 253-1800
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