luxury houses for sale Woodbury, United States

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.

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.

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 at the end of a quiet cul-de-sac in one of Roxbury's most desirable neighborhoods, this beautifully updated 4-bed, 3.5-bath Post & Beam Colonial offers a rare combination of privacy, character & flexibility. Exposed white oak beams, soaring 27ft ceilings, and 3 fireplaces create a warm architectural presence throughout the home, while thoughtful updates provide modern comfort and convenience. An active solar energy system helps offset utility costs and enhances long-term efficiency. Set on 3+ private acres, the property enjoys an exceptional natural backdrop with extensive undeveloped acreage beyond the rear property line, creating privacy and peaceful woodland views. Mature landscaping, a spacious deck, and a serene setting make the outdoor spaces ideal for entertaining or quiet enjoyment. The flexible floor plan includes a private in-law, studio, or home office space, ideal for today's evolving lifestyle needs. Beyond the 3,340 sq. ft. of above-grade living space, the home offers an expansive full lower level providing approximately 1,700 sq. ft. of dry bonus space ideal for storage, recreation, workshop, fitness, or future customization. An enormous walkable attic spanning nearly the entire 2nd floor footprint provides exceptional add'l storage rarely found in homes of this era.

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.

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.

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.

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.

Exceptional equestrian estate featuring a fully equipped horse facility and charming Cape-style home. Ideal for equestrians, trainers, or boarding professionals, the property offers 16 rubber-matted stalls, a large well-lit indoor arena, and a second-floor viewing lounge with kitchen amenities-perfect for lessons, clinics, and entertaining. The barn includes a wash stall, feed room, hay storage, boarder tack lockers, laundry area, and full bath. Safety is enhanced by a commercial sprinkler system. Owned pole-mounted solar panels are installed but are not currently operational. Outside, expansive grass paddocks and a large sand/stone dust outdoor arena provide ample space for training and turnout. Bordering Land Trust property with a river and miles of trails, you can horseback ride or hike directly from your back door. The Shepaug is one of those rivers that looks like it was painted by someone who had too much talent and not enough canvas. written by Charles Hayes. The Cape-style home features 3 bedrooms and 2 full baths, blending classic New England character with modern comfort. A 2-car attached garage is complemented by a detached 4-car garage, plus an additional detached 3-car garage with a second-floor apartment-ideal for guests, staff, rental income, or a home office.

Welcome to this impeccably maintained, sprawling Colonial situated in the heart of Watertown. Boasting 4,321 square feet of living space, this home offers a perfect blend of timeless design and modern comfort. The main level features a spacious chef's kitchen complete with an island, breakfast nook and a butler's kitchen for seamless food preparation. The great room boasts a cozy fireplace and sliders leading to a back patio, perfect for indoor-outdoor living. The office/den and formal dining room are elevated with crown molding and recessed lighting, with gleaming hardwood flooring throughout the main level. A half bath and attached three-car garage complete the main floor. The upper level features four spacious bedrooms and four full bathrooms, providing ample room for every lifestyle. Outside, you can enjoy the well-manicured grounds and a private concrete patio, an ideal setting for outdoor entertaining or peaceful relaxation. Built in 2000, this property is a rare opportunity to own a home of this scale and quality in a prime location with beautiful views of the Litchfield Hills.

A Mid-Century Masterpiece in Bridgewater- Perched atop one of Bridgewater's most scenic vantage points, this meticulously maintained modern retreat offers a rare blend of architectural integrity and breathtaking natural beauty. With its elevated views of rolling farmlands and protected open space, creating a sense of total tranquility. Step inside to a residence that truly needs nothing. Every inch of this 2-bedroom (Office can be used as 3rd bedroom), 3-full-bath home has been preserved and updated with an eye for detail. Stay perfectly comfortable year-round with central air conditioning and a state-of-the-art heating system. The open-concept layout and expansive windows invite the outside in, bathing the interior in natural light. From the pristine flooring to the high-end finishes, this is a home defined by pride of ownership. The exterior is a masterclass in professional landscaping. Wander through vibrant floral gardens that have been curated to bloom throughout the seasons, all while being bordered by the quiet majesty of Connecticut's rural landscape. It is a private sanctuary that feels worlds away, yet remains elegantly connected to the heart of Litchfield County. This isn't just a house; it's a piece of art waiting for its next chapter. Whether you are looking for a sophisticated weekend getaway or a permanent peaceful escape, this home is ready to welcome its new loving family. Schedule your private tour today

Meticulously maintained and privately set on 1.8 acres abutting protected open space, this three-bedroom home enjoys water views that shift beautifully through the seasons. Deeded access to the neighboring open space and reservoir invites fishing, kayaking, and quiet relaxing along the water. The main level's open-concept floor plan feels made for easy living, with an updated kitchen, featuring an island perfect for casual gatherings, flowing into a sunny eating area and on into a vaulted great room anchored by an impressive stone fireplace. Slide open the doors and you're on an elevated deck looking out over the water. A formal dining room, light-filled living room, laundry, and powder room complete the level. Upstairs, the spacious primary suite is a genuine retreat: private bath with soaking tub, walk-in closet, and the kind of stillness that makes unwinding effortless. The two additional bedrooms each offer flexible space for a home office, reading nook, or sitting area, and share a hall bath. The lower level adds finished space with a full bath, ready to become a guest suite, home gym, or media room. Secluded without being remote and close to everything that makes the Litchfield Hills worth calling home.

Escape to the beauty of Bridgewater, Connecticut! This completely renovated home on 2+ acres will welcome you. A stunning home from one room to the next with open space and perfect updates. The kitchen is a true show stopper. The abundant soft close cabinetry, stainless steel appliances, the granite countertop, and island create a great entertaining space framed perfectly with rich dark beams. Move to the dining room -there are walls of windows, moldings, and hardwood floors. A center staircase wraps to the living room, where a fireplace with a striking mantle centers the room. Step out to a screened-in porch surrounded by nature- a quiet brook and privacy set the mood. 4 bedrooms on the upper level, bright and spacious, hardwood, and plenty of closet space. A fully updated bath with detailed tiling is just lovely. The spacious finished attic has natural light, hardwood floors, and can be used for play space, extra beds, or an office. This special property offers a new professionally landscaped yard with a 2-car detached garage easily reached from the covered deck. Large basement with utility sink and newer mechanicals, dual AC/ heat electric system, oil furnace was replaced in January 2026, and additional storage and walkout. A favored escape spot for many, Bridgewater is unique. This home will not disappoint. Just open the door and discover for yourself how great it is to be home. Located just minutes from both Bridgewater's village center and the town of New Milford.

Lovely hilltop location in Heritage Village! This Sherman shows like a model home, offering a comfortable, functional layout with no stairs. Set in a wonderful private setting with beautifully maintained grounds, just minutes from the pool and pickleball courts. The open-concept living and dining areas feature a newer wood-burning fireplace, crown molding and wainscoting, and sliders to a private enlarged patio with a motorized awning and peaceful views. The eat-in kitchen includes quartz countertops, glass tile backsplash, stainless steel appliances, and breakfast bar plus dining area. Additional recent improvements include all new flooring in 2025, a new water heater in 2025, and updated custom light fixtures in the living room, dining area, kitchen, and primary bedroom. The primary suite offers a redesigned bath with double sinks, Carrera marble vanity top, walk-in closet, ceiling fan, and sliders to the patio. The guest bedroom provides added flexibility with a newly installed built-in Murphy bed, making it ideal as a bedroom, home office, or exercise room. Plenty of guest parking. Heritage Village offers an exceptional array of clubs and activities, along with convenient access to Southbury shopping, dining, medical providers, and major commuting routes. Nearby golf options include Silo Point Country Club, Gainfield Farms, and Pomperaug Golf Course.