luxury houses for sale Woodbury, United States

Nestled within one of Roxbury, Connecticut's most quiet and picturesque enclaves, this charming 3-bedroom, 2-bath Cape Cod home offers a rare opportunity to cultivate your dream country retreat. Built in the 1970s, this residence presents a wonderful canvas for those seeking to personalize and update a home within a highly sought-after area, celebrated for its exquisite properties and serene landscapes. The idyllic surroundings include a tranquil stream which meanders down through the property, while established mature plantings burst with color and life, providing a private oasis for relaxation and enjoyment. Imagine alfresco dining on the inviting stone terrace, or pursuing your gardening passions in the dedicated garden shed. This home is ready for its next chapter, offering a foundation of classic Cape Cod charm awaiting modern touches. It's an exceptional chance to invest in a lifestyle of peace and natural beauty, surrounded by the distinguished homes that define this desirable corner of rural Connecticut. *Town tax records - 3 bedrooms, health file has 2.

This cross gabled farmhouse was built in 2006 by its artisan craftsman owner, expanding upon the original foundation of a dwelling previously occupied by the caretaker of Arthur Miller's residence. The home was designed to leverage distant views east that stretch across thousands of acres of forested land to ridgelines in the towns of Woodbury and Bethlehem. The owner harvested and milled trees found locally to construct the flooring, stairs, cabinetry, interior doors and most of the finish moldings, creating exceptional detail and character rarely found at this price point. No less impressive is the handsome and considerable stonemasonry he crafted, surrounding the house and connecting its points of entry to exterior living spaces. All three bedrooms have windows facing the long views with both the primary suite and open kitchen/dining space featuring french doors to the outdoor stone terrace extending toward the panoramic scenery. Magnificent living room with granite framed wood burning fireplace and a flat screen TV cabinet above the mantle that is flanked by built-in bookshelves. Large main level den/office and dedicated pantry with sink, wine fridge and game freezer. Second floor office could also be used for overflow guests. Savor the secret lifestyle sauce located in Roxbury's coveted southeast hill country that has drawn luminaries past and present, including Miller, Monroe, Widmark, Matthau, Calder, McCourt, Hoffman, Rayburn, Reed, Bushnell, Leoni & Ecklund.

At the end of a long, winding private driveway, this exceptional Roxbury estate offers total seclusion & tranquility-surrounded entirely by protected land trust. Just 2 miles from Roxbury Center and a scenic 2-hr drive from NYC, this rare property is the perfect country escape or full-time residence. The main home is in impeccable, move-in condition, featuring dramatic vaulted ceilings in both the living room and kitchen. A striking floor-to-ceiling flagstone fireplace with a wood stove insert anchors the living room, while a cozy wood-burning fireplace warms the kitchen, creating a welcoming and timeless atmosphere. The chef's kitchen is outfitted w/ granite countertops & top-of-the-line stainless steel Viking appliances, opening seamlessly to a spacious stone patio ideal for entertaining. Luxury continues outdoors with a stunning in-ground pool surrounded by custom stonework, a charming gazebo, and a separate hot tub nestled in nature. A nearby fire pit invites cozy evenings under the stars. Just off the living room, a wet bar adds ease & sophistication to indoor gatherings. Add'l features include a large separate loft apt perfect for guests or remote work, a two-car garage, a second shed/1-car garage w/ electricity, and a full-house generator for year-round comfort. A driveway annunciator ensures privacy and peace of mind. Enjoy nearby shopping and dining in Washington & Woodbury while returning home to your private, resort-like sanctuary in the heart of Litchfield County.

Presenting a truly rare opportunity for BRAND NEW CONSTRUCTION in Roxbury, CT, this luxury residence offers approximately 3,300+ SF of meticulously designed living space, including a spacious finished basement & attached double garage. Enjoy exquisite finishes throughout, highlighted by 6 white oak hardwood flooring, custom architectural millwork and decorative shiplap details. The gourmet Kitchen is designed with a farmer sink, pot filler, stone countertops and high-end stainless steel appliances including double wall ovens, LP gas cooktop & microwave drawer. The open plan Living Room centers on a remote-controlled LP gas fireplace with stone surround and features a dramatic 16' wide x 8' high Andersen sliding glass door leading directly to the outdoor entertaining space. Two additional rooms could serve as a study/den and a formal dining room. A main-level Primary Bedroom offers a generous walk-in closet and en-suite bath featuring a spa-like experience with double shower systems, zero-clearance shower floor with a linear drain and wall-to-wall glass. The powder room and Mud room (with laundry) complete the main level. Upstairs there are two bedrooms which share a full bath, a large bedroom with an en-suite bath, and a large walk-in attic (approx 800 sq ft) ready for optional future finishing. Further living flexibility is provided by an expansive 41' long finished lower level and a full bath. The exterior boasts premium materials, including James Hardie cement fiber plank siding, black-clad Andersen 400 Series windows and doors, a wrap-around deck with mahogany surfaces and a bluestone rear patio & front walkway. Utilities are serviced by underground electrical wiring, a new drilled well and 5-bedroom septic system with an underground 1,000-gallon propane tank. The home is engineered for quality and efficiency, featuring full spray foam insulation (R30 walls, R60 ceiling/attic) and Central Air with a high-efficiency Heil three-zone propane gas fired HVAC system. Plans for a pool are available, along with architectural drawings and a detailed spec. sheet of all the features. Town approvals are already in place for a pool as well as a barn and shed.

Perfect Country Home! Located close to town on a quiet country road. Built is 2018, the new owners have done extensive Landscaping. A privacy fence was installed on the front of the property with evergreens planted on both sides of the fence . There is a small apple orchard planted on the property. Extensive stonework and plantings have been done around the house and an in ground pool with pebble tech finish was installed with fencing in the rear yard for the pool and pets. The house was originally built by a Master Craftsman with the finest materials.The gourmet kitchen is where everyone lives. There is a center island and field stone fireplace. Thermador appliances include a 6 burner cook top as well as wall oven, built in microwave, a warming drawer, dishwasher and refrigerator. The open floor plan allows you to set up the living room/dining room in a variety of ways. There is a lovely sunroom with a vaulted ceiling off the kitchen. There is a mudroom coming in from the garage with a half bath. The ceilings are 9' on the first floor. The upper level includes a lovely Primary Suite with walk in closets, a luxurious primary bath with 2 sinks, a walk in shower and a soaking tub. There are 3 additional bedrooms on the upper level with one en-suite and the other two sharing a hall bath. The house sits up high with mountain views. The land is gently sloping with a level area with plenty of room to play. Only 90 minutes to NYC!

Cottage & Guest House Located in pastoral Southern Roxbury, just 90 minutes from New York City. Set on 2 acres, the property features a historic c.1817 three-bedroom antique cape-featured in Elle Decor-a charming two-bedroom guest house. The main residence exudes rustic character, with original hand-hewn beams, wide-plank oak floors, a wood-burning fireplace, and classic plaster walls. At its heart is a spacious eat-in kitchen, flanked by a formal dining room and library on one side, and a sunlit living room wrapped in windows on the other. The 658 square-foot guest house overlooks the spring-fed pond and includes a generous living room, two bedrooms, and a full bath-serviced by its own septic. The grounds are serene and beautifully landscaped, with a cantilevered waterfront sun deck, mature trees, lush gardens, and gently rolling lawn. This charming home blends history, potential, and natural beauty in one of Litchfield County's most coveted locations., Additional acreage available- separate 6.71-acre buildable lot with potential for a spacious custom home at the end of a long, private driveway. Total square footage is combined main house and guest house.

Looking to escape the hectic pace of city life? Welcome to this peaceful, beautifully renovated 4-bedroom home, originally built in 2005, offering the perfect blend of comfort and tranquility. Featuring 2.5 baths and a spacious open-concept living and dining area, this home is ideal for hosting gatherings and entertaining with ease. The modern kitchen is a dream for any home chef, complete with state-of-the-art appliances, ample counter space, and generous storage. Enjoy stunning outdoor views from every angle and make the most of the inviting outdoor space. Perfect for alfresco dining or simply relaxing in nature. A 3-car garage provides plenty of room for parking, storage, and hobbies. This home offers a wonderful setting to grow and thrive, whether you're raising a family or settling into a peaceful lifestyle. Located in Roxbury, a quiet rural town rich in New England charm, you'll enjoy scenic countryside, historic sites, hiking at Mill Hill Preserve, and local artisanal goods at the Roxbury Market. A true retreat with timeless appeal.

Juniper Hill offers masterfully updated one level living in Roxbury, Connecticut. Dubbed a Little Gem on the Hill in Country Home, this unassuming ranch has been elevated with chic, yet family friendly styling. Modern comforts combine with country character in a home situated on compelling terrain. Kelly + Co Design awarded Best Interior Designer Small Home/Cottage, 2020, CT Cottage and Gardens for their work on this home. Primary bedroom en suite with stall shower and claw foot tub. Two guest bedrooms share full bath with wall to wall shower offering the choice of a traditional or rain shower head. Oversized living room windows face west and are opposite a grand wood burning fireplace. A bay window looking out to the pool lends charm to the dining area. Magnificent sunroom wrapped in windows that bring the outdoors in. Top of the range projection home theater. Chef's kitchen with fireplace has windows lined above the sink counter looking out to the large, level yard and play areas. Cooktop set in sizable island that has additional cabinet storage and breakfast bar. Whole house generator, Central air, brand new gas furnace heat and on-demand hot water. Two-bay, detached garage. Buried utility lines.

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.

Light-filled, modern living on a private nearly 3-acre corner lot - with room to grow. Set on a beautifully positioned corner parcel, this fully renovated home is defined by natural light and flexibility. Expansive windows and vaulted ceilings create a bright, open feel throughout the main living spaces, bringing in sunlight from multiple exposures and connecting the home to its surrounding landscape. Completely transformed with high-end finishes and energy-efficient upgrades, the home offers the ultimate floor plan, featuring two first-floor ensuite options and close proximity to Roxbury Market, town tennis courts and Hurlburt Park.Beyond what's already been thoughtfully updated, the property offers meaningful future potential. The grounds are well-suited for additional features creating an opportunity to further enhance the outdoor experience over time. Transition to outdoor living through the integrated open porch, featuring a dramatic black-vaulted ceiling and stone tile flooring-ideal for lounging or future screening. The finished lower level adds another layer of versatility, with walk-out access and the ability to evolve with your needs-whether as a pool house, gym, office, creative studio, or additional guest space. A rare combination of move-in-ready ease and long-term optionality, all set on a private and peaceful setting.

Perched above the tranquil waters of Jacks Brook in southern Roxbury, this Modern Mountain Tudor offers refined open-concept living with exceptional accessibility to New York City, just five minutes from Roxbury Center. Set on a private, level site, the property enjoys protected brookside land that preserves the natural landscape and uninterrupted views that define the home's character. A grand circular driveway introduces the residence, where sweeping lawns and striking architecture create a powerful sense of arrival, privacy, and seclusion. Inside, light-filled interiors showcase soaring ceilings and oversized windows that capture serene vistas from nearly every room, blending contemporary sophistication with warmth and comfort. The remodeled kitchen serves as the heart of the home, seamlessly combining modern design with functional luxury as it flows into the main living areas. With five generously proportioned bedrooms and six bathrooms, the thoughtfully scaled floor plan accommodates both grand entertaining and intimate everyday living. The lower level features a versatile in-law suite complete with a full kitchen, private bedroom, bathroom, living room, separate entrance, and direct access to the grounds, along with an additional great room or family room that opens to the expansive lawn, offering a seamless indoor-outdoor connection ideal for guests or multigenerational living.

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.

Western Sunset Views, a short distance from The Mayflower Inn and Washington Green. Discover the ultimate renovation project or the foundation for your future estate. Situated in an elite enclave of fine homes, this 1890s Barn-style residence-complete with its signature silo and 1970s additions-awaits a visionary touch. Whether you envision a meticulous restoration of a historic showpiece or a chic, modern transformation, the potential here is as vast as the western horizon. The acreage has been strategically cleared to unveil stunning western exposures. The property is anchored by a mature landscape, featuring: Stone Terrace & Deck: Perfect for seamless indoor-outdoor entertaining. Rustic Writer's Cottage: A charming, detached retreat for creative pursuits or a quiet home office. Additional structures offering utility and historic character. The interior features an existing open floor plan, providing a fluid transition between the kitchen, dining, and living areas. Renovate the existing structure into a sprawling, personalized dream retreat that blends 19th-century charm with 21st-century luxury. The Guest House Strategy: Scale back the current residence to serve as a sophisticated guest house or secondary dwelling while you build a new primary manor. Bring your architect and your ambition-your slice of paradise is ready to be built. The Vision: Restoration or Reimagination The interior features an existing open floor plan, providing a fluid transition between the kitchen, dining, and living areas. This layout serves as the perfect bones for a high-end modernization.

Quintessential Country Cottage, a perfect blend of form and forest. Privately tucked away on four acres of natural Connecticut landscape, this custom-built, two-bedroom shingle-style residence is a rare marriage of rugged post-and-beam soul and refined modern luxury. Ringed by ancient stone walls and shielded by a soaring canopy of mature oak, maple, and pine, the home serves as a secluded sanctuary. Following extensive renovation and enhancement by the master craftsmen at West Mountain Builders, every inch of the nearly 2,000-square-foot above grade interior reflects exquisite attention to detail. A studio apartment over the detached garage complete with kitchenette & full bath is ideal for guests or a private workspace. Washington is known for its charming village center, rolling hills, and vibrant cultural scene. Take advantage of nearby destinations, including the shops of New Preston, Lake Waramaug (residents have beach rights), the hiking trails of Steep Rock Preserve, and the renowned Mayflower Inn & Spa. Ideally located near top-rated schools, this home can serve as a full-time residence or a quiet weekend retreat. Two acres of the property have a conservation easement. Main house has geothermal heating/cooling system. Property has 2 septic systems, one for main house and one for garage apartment and a full property Kohler generator. Security cameras are operational on outside of house and garage.

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.

Effortless elegance meets modern convenience in this meticulously reimagined 9 room ranch on 1.8 private acres in coveted Washington. This 2,113-square-foot sanctuary offers sophisticated single-level living with nothing left to do but move in. Light-filled spaces feature two fireplaces with propane inserts and gleaming refinished hardwood floors. Stunning open-concept kitchen/family room showcases Taj Mahal quartz counters, porcelain backsplash, all new appliances including double oven and wine fridge, under counter lighting. Fireplace and stone hearth- ideal for entertaining. Three generous bedrooms include primary suite with Thasso marble bathroom with walk-in shower. Second full bathroom with Thasso marble and tub/shower. Bright half bath features full-sized stacked washer/dryer. Den/Office/4th bedroom w/built-ins. Charming garden room (22x13) with bluestone floor overlooks bucolic grounds. Comprehensive renovation includes new roof, new septic, all new windows, central air, Heil propane boiler, on demand hot water, new electrical panel, custom lighting, and new whole-house generator. Mahogany deck(42x13) expands entertaining space. Walk-out basement provides storage; full attic offers expansion potential. Two car attached garage. Complete turnkey. Near fine dining and shopping in Washington, New Preston, Bantam and Litchfield. Winter skiing at Mohawk Mountain and fishing in the Housatonic River...Steep Rock Park for wonderful walks-Lake Waramaug for a swim. Field card states 4 bedrooms - one bedroom has been turned into a library or office. Garden room is not heated but contributes an additional 286 square feet of living space.

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.

Discover this charming 4-bedroom Colonial with 1 additional bedroom is attached in-law apt on the southern side of Roxbury, offering an idyllic escape with seamless access to NYC. This privately situated home rests in a serene meadow, gracefully bordered by Pierce Brook. The main residence features a comfortable layout with a living room and fireplace that flows into the dining area and kitchen. Upstairs, you'll find four spacious bedrooms and two full bathrooms. A bright slate floored sunroom overlooks the inviting heated salt pool, perfect for relaxation and entertaining. Adding to its unique appeal is an attached 1-bedroom in law/guest house with propane heating and cooling, providing flexible space for visitors or extended family. The property boasts level land and lush grounds, including a expansive pasture area, all set against the picturesque backdrop of Pierce Brook. This Roxbury gem combines tranquility with convenience, making it an ideal retreat.

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.