luxury properties for sale Woodbury, United States

Tucked away in one of Roxbury's most desirable neighborhoods, this 4-bedroom, 2.5-bath Colonial sits at the end of a quiet dead-end road, offering exceptional privacy and a peaceful setting, with the Natalie White Preserve just down the road. This beautifully updated Post & Beam home blends timeless craftsmanship with modern amenities, featuring warm architectural details, exposed white oak beams, and a dramatic living room with soaring 27-foot ceilings, along with thoughtfully designed living spaces. The flexible layout includes a private in-law or studio space, ideal for guests, extended family, or a home office. Set on a serene, wooded 3-acre lot with mature landscaping, the property provides a tranquil retreat perfect for relaxing or entertaining. Despite its secluded feel, it's a short 15 minutes drive from fine-dining, shopping, and easy access to I-84, and ideally located just over 90 minutes to NYC and approximately 2 hours 20 minutes to Boston, offering both convenience and comfort in a truly special location.

Your turnkey country escape is waiting in Roxbury - a modern shinglestyle home on 4+ manicured acres with a resortlevel pool, just far enough from the city to exhale, yet close enough to make spontaneous weekend getaways a reality. From the moment you arrive, this summer ready property feels like a private club: stone walls, curated landscaping, quiet woods, and outdoor spaces designed for long summer days and late night gatherings. The gunite pool is the centerpiece - sparkling, secluded, and ready the moment you are. Inside, sunlight pours through picture windows into an open layout built for effortless entertaining. Custom oak details, a dramatic fieldstone fireplace, and a chef's kitchen with high-end appliances and stone counters set the stage for everything from cozy winter weekends to lively holiday hosting. With 4 ensuite bedrooms, the home adapts beautifully to guests and long family weekends. The first floor ensuite offers effortless hospitality, while the second floor luxury primary suite- complete with 11 foot ceilings and a marble spa bath - provides a calm, spa-level retreat. A steel-and-glass office alcove and a bonus room above the garage with interior access, offer the perfect flex space for a studio, gym, or potential guest suite. The finished lower level and walkout access adds even more room to unwind. Fully renovated since 2021 including new HVAC, generator, and more - means no projects, no delays to start enjoying the Litchfield Lifestyle.

Own a Piece of Roxbury History! One of Roxbury's three oldest homes, this site has been cherished by seven generations of the Squire family. The existing antique home, while requiring reconstruction, has the potential to be reimagined as a charming guest house, preserving a tangible link to the past. Set on 12.7-acres this property and boasts breathtaking eastern views and the unique opportunity to create a stunning estate on land steeped in local heritage. A partially intact stone foundation (approximately 1500 sq ft) provides a solid base for this endeavor. Imagine building your dream home atop the hill, capitalizing on the panoramic vistas. A beautifully renovated barn, listed as historic landmark, adds further character and value. The property abuts Land Trust for hiking, ensuring privacy and natural beauty. Infrastructure is in place with a completed A-2 survey, installed driveway, and approved septic plans (3-bedroom for the antique home and 8-bedroom for a main residence). Electrical conduit is also installed to the proposed homesite. This land has subdivision potential and is ready for you to create a legacy of your own. **Note: Home is uninhabitable at this time. A full rebuild and renovation is required.

Nestled perfectly on over five private acres, this classic three-bedroom Colonial offers the ultimate serene country escape. Step inside, and you are immediately greeted by radiant natural light and the warmth of newly refinished, gleaming hardwood floors that flow seamlessly throughout the home.To the right of the welcoming entryway, a spacious living room awaits, anchored by a cozy wood-burning fireplace. Just adjacent is a charming library nook, thoughtfully designed with two walls of custom built-ins, perfect for reading or family game night. On the opposite side of the home, the dining room flows into a kitchen that is as picturesque as it is functional. Well-appointed for the home chef, the kitchen also offers direct access to a brand-new deck, setting the ideal stage for summer barbecues and al fresco dining. Practicality meets luxury in the back hall, which boasts exceptional storage, a dedicated laundry room, a walk-in closet, and a pristine powder room.Upstairs, the generously proportioned primary suite serves as a true private retreat. It features its own romantic wood-burning fireplace, a wall of closets, and a full en-suite bath. Two additional bright bedrooms and a well-appointed guest bathroom complete the second floor.The walk-out lower level expands the living space remarkably, offering wonderful flexibility with an additional bedroom, a family room, a dedicated gym space, and utility access. Designed for easy maintenance, this quintessential country haven perfectly balances seclusion with convenience-offering total privacy while being just 10 minutes from Washington Depot and under 20 minutes to historic Litchfield.

Stone Bridge: The Ultimate Classic Country Estate - PERFECTION AND READY TO MOVE IN! Embodying the pinnacle of refined country living, Stone Bridge is a magnificent stone and shingle estate with Elevator to all floors and Geothermal Heating, that seamlessly marries timeless architectural grandeur with state-of-the-art modern amenities. Situated on over 24.9 private, bucolic acres in Washington, Connecticut's highly desirable Nettleton Hollow area, this masterfully crafted property offers an unparalleled sanctuary of elegance and privacy. Constructed by the HOBI Award-winning Corbo Associates, the residence spans more than 7,000 square feet of sophisticated living space, complemented by an additionally finished 3,100 square feet on the lower level. A seamless indoor-outdoor flow defines the main living areas, which open gracefully onto sprawling terraces and a covered patio complete with an outdoor fireplace. The manicured grounds serve as a private resort, featuring mature plantings, artisanal stonework, a full irrigation system, and a pristine, heated gunite pool. Inside, soaring ceilings and expansive walls of glass flood every room with natural light while bringing the breathtaking countryside views indoors. The estate features five luxurious bedroom suites, including the rare flexibility of both first- and second-floor primary retreats. An elevator effortlessly ensures absolute accessibility throughout the home. An entertainer's paradise, the estate boasts seven fireplaces, an elegant library, home theater, a game room, gym and a spectacular 1,500-bottle wine cellar with a dedicated tasting room. Culinary enthusiasts will appreciate the top-of-the-line main kitchen, which serves as the heart of the home, alongside a full butler's kitchen designed for seamless event hosting. Built to the highest standards of construction and energy efficiency, the home features sound-dampened walls, a comprehensive security system, an integrated generator, and central vacuum. Future-proof technology is woven throughout the property, utilizing a cutting-edge geothermal heating and cooling system and Cat 6 audio wiring for premium sound, data, and internet connectivity. The estate is approached via a long, meandering driveway that overlooks a nearby pond, leading to a three-car garage connected via a stately porte-cochere to a second garage. Stone Bridge is more than a residence; it is an extraordinary country lifestyle.

Welcome to 14 Cook Street, a charming circa-1900 Victorian located in the heart of Washington Depot. Rich in history, this home was once known as Cook's Boarding House, a local inn that helped shape the character of this picturesque New England village. Offering approximately 1,800 square feet of living space, this 4-bedroom, 2-bath home features a traditional layout with a living room, dining room, den, and kitchen with pantry. Period details blend seamlessly with comfortable living, providing both character and functionality. Set on 1.3+ acres, the property offers a rare combination of in-town convenience and private outdoor space. The level lot is enhanced by mature landscaping and includes a fenced in-ground pool-ideal for summer entertaining or quiet relaxation. Located just steps from the village center, enjoy easy access to local shops, cafes, and everyday conveniences. Washington Depot is widely known for its scenic beauty, historic charm, and proximity to Lake Waramaug, Steep Rock Preserve, and numerous outdoor recreation opportunities. Ideally situated between New York City and Boston, this property is well-suited as a full-time residence or weekend retreat. A unique opportunity to own a historic home in one of Litchfield County's most desirable towns. Buyer backed out 1 week before closing for personal reasons! Brand new pool liner, ready to move in!

This charming Colonial-style home at 408 Hut Hill Road in Bridgewater, CT, offers a cozy retreat with modern amenities. The interior boasts a total of 7 rooms, including a spacious living room, a combined kitchen and dining area, and four bedrooms with a primary suite featuring a private bath. The finished lower level provides additional living space ideal for entertainment or relaxation. Custom carpentry details add character and functionality to the home, creating a warm and inviting atmosphere. With a living area of 2165 square feet, this property is perfect for those seeking a peaceful and connected lifestyle. Enjoy the best of both worlds at 408 Hut Hill Road, where modern comfort meets natural serenity. The exterior features of this home include a vinyl siding, gutters, garden area, and outdoor lighting. The property sits on a 2.08-acre lot that borders open space, offering a picturesque and tranquil setting. The attached garage with space for 3 vehicles provides convenience and storage options. The house is surrounded by a level lot and open land, providing plenty of space for outdoor activities and relaxation. Whether you're unwinding on the front porch or exploring the nearby hiking trails, this home offers a harmonious blend of indoor comfort and outdoor beauty. Nestled in the heart of Bridgewater, CT, this home offers a unique opportunity to embrace a lifestyle of peace and connection. The neighborhood provides access to various amenities, including a basketball court, lake, library, paddle tennis courts, playground, and stables for riding enthusiasts. With easy access to essential services and a close-knit community, residents can enjoy the tranquility of rural living without sacrificing convenience. The property's proximity to schools and local attractions makes it an ideal choice for families or anyone looking to immerse themselves in a vibrant and welcoming community.

Experience the perfect blend of sophisticated design and rural tranquility in Lakeside. This beautifully remodeled cottage has been reimagined with a distinct modern flair, offering a turnkey escape that balances contemporary finishes with the peaceful soul of Morris. This recent renovation has been executed with an eye for style, making it an ideal sanctuary for those seeking a chic weekend retreat from the city or a charming permanent residence. Set on a sprawling 3.68-acre lot, the property offers a rare level of privacy and serves as a true blank canvas for your future lifestyle. The interior radiates a bright, airy energy, featuring contemporary lines and thoughtful details that honor the home's original character. Outside, the vast grounds invite you to explore, garden, or simply soak in the quietude of Litchfield County. The location is a dream for outdoor enthusiasts and foodies alike. You are just moments away from the shimmering waters of Bantam Lake for summer recreation and the expansive trail systems of White Memorial Conservation Center for year-round hiking and exploring. When it's time to head into town, the iconic Litchfield Green is a short drive away, offering world-class restaurants, artisanal shops, and gourmet food markets. Whether you are looking for a minimalist haven or a stylish home base to enjoy the best of Northwest Connecticut, 72 Hickory Hill Road is a masterclass in modern country living.

A custom-built Victorian reproduction in the Italianate style. Masterfully designed by it's original owners. No detail has been overlooked in this remarkable design. This unique offering is equipped with all the modern conveniences of a newer home blended with charming architectural design elements and historic, vintage charm. The first floor boasts an open floor plan with expansive custom kitchen, pantry and formal dining area with reclaimed antique fireplace with custom carved mantel and surround. The spacious living room is equipped with a second fireplace with an efficient wood-burning insert. A first floor powder room and separate den with glass french doors completes the first floor. A breezeway with custom bench and storage area conveniently connects the first floor to the three car garage area and rear patio with custom grill area and hot tub/spa. A large primary bedroom suite on the second floor is well equipped with a soaking whirlpool bathtub, a separate tiled shower stall, large vanity with double sinks and a spacious walk-in closet. Two additional bedrooms share a hall bath with a separate laundry room. Beautiful hardwood flooring and custom trim, tray ceilings, and custom moldings throughout the home. A partially finished basement of approximately 1000/sf. consists of a large family room, a large recreation room and an additional area utilized as an exercise room. Proximate to the Watertown Country Club, Rumsey Hall, and the Taft School. Please do not enter the driveway or property without an appointment confirmed with the listing agent.

Enjoy sunrises from the covered front porch and stunning sunsets from the large back deck of this 4 bedroom and 2 1/2 bath Stately Colonial in the sought after location of Town Ridge Estates. Inside you'll find hardwood floors throughout the main level with a dining room, living room, and a spacious kitchen wide open to large family room, which is anchored by a gas burning fireplace. The primary bedroom is upstairs with 2 walk-in closets, a tray ceiling, and a primary bathroom with a jet tub and double sinks. There are 3 other bedrooms and a full bathroom with double sinks. Have fun in the 700sq.ft. of finished space in the walkout lower level with your own dance floor! The two car garage is oversized to accommodate lawn and gardening items.

Experience the quintessential Litchfield County lifestyle in this beautifully renovated 1930s cottage. Set in the prestigious New Preston section of Washington, CT, this property is a masterclass in country chic, offering a serene pastoral setting defined by stone walls and breathtaking orchard views. The grounds have been professionally landscaped to create a private sanctuary that delights the senses. A stunning, brand new saltwater gunite pool serves as the centerpiece for summer relaxation, framed by the quiet beauty of the Washington countryside. Whether you are a culinary enthusiast or a nature lover, you will appreciate pear and peach trees, thriving blueberry bushes, and a dedicated asparagus patch. There's also a fully fenced-in flower and vegetable garden with raised beds ready for your seasonal plantings. Inside, the home retains its historic 1930s soul while offering the modern comforts expected of a tasteful renovation to include an updated kitchen with vaulted ceiling, gas fireplace and hardwood floors throughout. It is the perfect turnkey solution for those seeking a cozy year-round residence or a sophisticated weekend retreat. This property is an absolute dream. New Preston is one of the most coveted corners of Litchfield County, and finding a renovated 1930s cottage with that specific orchard aesthetic-plus the infrastructure already vetted for expansion-is a rare find.

Back on the market in time for Spring!! This is the house you have been waiting for! Immaculate 4 bedroom, 3.5 bath Colonial sited on 1.16 acres of beautiful lawns and professionally landscaped gardens on a quiet cul de sac located in southern New Milford on the Brookfield line, with easy access to major highways. The home is light and bright and has been beautifully maintained with fresh interior and refinished floors. A cathedral ceiling foyer welcomes you into the home, you will enjoy 9 foot ceilings and great room flow on the main level. The eat-in kitchen opens to a family room with fireplace, formal living room and dining room. The second floor has a primary ensuite bedroom with wonderful walk-in closet. Another full bathroom and three spacious bedrooms complete the second level. There is an additional area (ensuite) over the garage which is perfect for a home office. This is a dream home for entertaining with an eat in kitchen that opens to the oversized deck, which overlooks the fenced in private backyard with heated inground pool, patio, fireplace and greenhouse.

An exceptional property with a rare convergence of historic provenance and modern excellence. This magical setting comprises a c.1777 home (once a Tollhouse), that blends 18th c. character, masterfully rebuilt in 2023. Step inside to a main floor that includes, a Kitchen, Dining Room, Parlor, Living Room & Primary BR suite including 3 FP's and a 3-season Solarium/Mudroom, Laundry room (ne' Buttery) and 1/2 BA. The Upper level has 2BR's and full bath. There are warm pine wood floors throughout. The enchanting park like setting includes, 3 parcels= 4.5ac.+-, with a pond, babbling stream, a 2-car barn-style garage with a ~400sf upper level studio incl. a sitting and sleeping area, a heated in-ground pool, well-established perennial gardens and pathways, stone walls and a gently rolling hill that borders the Land Trust. It is Connecticut pastoral perfection at its finest. WAIT!!! There's more...An opportunity to start a new, on-site business, currently, a 400 sf Antique Shop. For the collector, artisan or entrepreneur, seeking a life-work retreat or just pure tranquility. This is a one-of-a-kind property with incredible flexibility, delivering, history, beauty & endless possibilities, it is an extremely RARE opportunity. Are you ready to live your next chapter! Conveniently located between the storied villages of Litchfield, Bantam, New Preston & Washington for shopping, dining, hiking, skiing, boating or just relaxing. COME HOME TO THE HILLS OF NW CT 2 hrs. to NYC This property has audio and video surveillance .

Nestled in a nice neighborhood, 46 High Ridge Road presents a fantastic opportunity for those seeking a spacious and well-built Colonial home with incredible potential. Situated on a picturesque and fully usable acre of park-like land, this 4-bedroom, 2.5-bath residence offers over 2,060 sq ft of thoughtfully designed living space. The main level boasts a kitchen with tile flooring that seamlessly transitions into a generously sized dining room featuring hardwood floors, a perfect space for family gatherings. The highlight of the main floor is the expansive front-to-back living room, complete with a wood-burning fireplace and custom built-ins, ideal for both relaxation and entertainment. A convenient powder room and a bright four-season sunroom with access to the deck and backyard complete the main level, providing a seamless indoor-outdoor living experience. Moving to the upper level, the primary suite includes a full bath and dual closets, offering a private retreat within the home. Three additional bedrooms, all with hardwood flooring, share a full hall bath with a tub, providing comfort and convenience for the entire household. The lower level adds an extra 264 square foot of finished walkout space, perfect for a recreation room, home office, or gym, while the clean, dry basement offers ample storage and utility space. The attached 2-car garage with direct kitchen access enhances everyday convenience for the residents. Beyond the walls of this charming home, enjoy the lush surroundings and the close proximity to top-rated schools, shopping centers, and major commuter routes, making daily life a breeze. With a little cosmetic refresh, this Colonial gem has the potential to shine brightly and become your forever home. Don't miss this chance to bring your vision to life and transform this property into a true masterpiece that reflects your style and personality. Come and experience the endless possibilities that await you at 46 High Ridge Road in Brookfield, CT.

This Charming Antique Cottage sits around the corner from Hopkins Inn and Hopkins Vineyard which both overlook Lake Waramaug. It is in need of some renovation which makes it a great opportunity to make it your own and well worth the effort. It is located in an area of scenic beauty and great estates. In the main level is a generous sized kitchen with a farm sink, an island and stainless appliances. Adjacent is a sweet dining room. A living room with a charming stone fireplace leads to a large sun room. A small reading room and half bath finish the main level. The upper level includes 3 bedrooms, a full bath and the laundry area. There is also a small barn that could be used for a potting shed, art studio or workshop. Enjoy the town beach on Lake Waramaug. The area has many hiking trails and outdoor activities. Enjoy the local farmers markets, restaurants, and boutiques. There are art galleries, local theatre and summer fairs to enjoy. (Will not qualify for FHA mortgage)

Nestled on 2 peaceful acres in Newtown, CT, 23 Old Green Road presents a beautifully maintained 4-bedroom, 2.5-bath Colonial retreat that exudes privacy and sophistication. Step inside this inviting residence to discover a remodeled kitchen boasting stainless steel appliances, marble countertops, and a butcher block island. French doors lead you from the kitchen to the expansive rear deck with built-in seating, offering the perfect setting for outdoor gatherings. The main level also features a cozy family room with a wood fireplace, a dining room with a bay window, a versatile living room or den with custom built-ins, and a convenient laundry/powder room with designer finishes. Make your way upstairs to find the primary suite, complete with a wood-burning fireplace, barn doors, custom closets, and an updated bath featuring elegant marble finishes and a rain shower. Three additional bedrooms provide flexible space for guests, a home office, or daily living needs. The property also includes a walk-up attic and a full basement with interior and garage access, offering ample space for hobbies, a workshop, a home gym, or storage. This Colonial gem has undergone major upgrades, including Central A/C installation in 2026, a high-efficiency System 2000 boiler added in 2025, rebuilt chimney with new flue liners, additional attic and basement insulation, upgraded electrical system, and a professionally painted exterior with a warranty. Additional highlights of this residence include recessed lighting, dimmers, fresh paint, upgraded closets, an epoxy garage floor, a security system, rebuilt front steps, new porch columns, beautifully landscaped grounds, a paver walkway, gravel patio, and fenced garden - all contributing to a welcoming outdoor space for relaxation and entertainment.

Discover exceptional country living in this updated vintage colonial set on a sprawling 2.5 acre private lot. This charming home is the perfect blend of classic architecture with modern amenities. Enjoy expansive outdoor space with a stunning stone heated pool and wonderful covered patio great for relaxation or entertaining. Inside the home boasts spacious living areas enhanced by large bay windows that flood the home with natural light, crown moldings, and hardwood floors. The main level includes both a living and family room each with its own fireplace, a large country kitchen, formal dining room and additional room on main level with full bath for office or au pair suite. The upper level features a primary suite complete with full bath, three additional well-appointed bedrooms, full bath, and laundry room. A standout feature of the upper level is the sleeping porch; this unique space is designed for relaxing and enjoying the outdoors while overlooking the scenic property. Convenient location to all that Brookfield has to offer! Shopping, restaurants, schools, parks, lakes, and easy access to the highway.

Set along a quiet ridgeline with long views over the surrounding countryside, this home offers a sense of privacy and space that's hard to find. A winding driveway leads you through manicured grounds to a timeless facade. Inside, the layout feels both open and purposeful. A two-story foyer and sweeping staircase create a strong first impression, while hardwood floors and custom millwork carry throughout the home. The main living areas connect easily; there's a formal dining room with a fireplace, a butler's pantry for added convenience, and a well-designed kitchen that opens to a casual dining area and a comfortable family room with a stone fireplace. The living room is lined with windows, bringing in natural light and framing the distant views. Built-ins add character and function, and the space extends to a covered porch, an easy spot to unwind. A main-level guest suite with its own entrance offers flexibility for extended family, guests, or a home office setup. Upstairs, you'll find four spacious bedrooms, including a primary suite with a sitting area, private balcony, and a spa-like bathroom with soaking tub and glass-enclosed shower. Outside, the stone patio creates a natural gathering space for entertaining or simply enjoying the setting. The grounds are open yet private, bordered by protected land, and a tucked-away hot tub adds a quiet place to relax at the end of the day. This is an unforgettable home in a setting that truly stands out.

Nestled in the serene cul-de-sac of prestigious Hubbell Mountain Farm North, 3 Partridge Trail in Sherman, CT, offers a luxurious and carefree lifestyle in a custom Colonial home. Set on 9.24 acres of level land adorned with colorful trees and charming stone walls, this property provides a tranquil retreat with picturesque country views. The open floor plan of this 4-bedroom, 2.5-bathroom residence exudes modern elegance and vintage charm, featuring gleaming hardwood floors, French doors, and antique finishes. The gourmet kitchen is a chef's dream, boasting a center cherry top island, Viking stove, Sub Zero refrigerator, and stainless steel appliances, seamlessly flowing into the dining and family room area with a custom wood-burning fireplace. A spacious living room, private home office, and powder room complete the main level, while a spindle staircase leads to the primary sanctuary upstairs, offering a walk-in closet and a luxurious marble bath with Edwardian-style console sinks and a soaking tub. Additional guest bedrooms with generous closet space and a shared full bath provide comfort and style, with a convenient laundry room rounding out the upper level. The full walk-out lower level offers potential for additional living space and storage, complemented by a 3-car garage and a Generac generator for added convenience.