luxury houses for sale Woodbury, United States

Painter Hill Cottage, a delightful 3BDR, 2 Bath cottage with heated, Gunite pool. Here is an opportunity to take this home to the next level on one of the most desirable roads in Roxbury. It offers a light and bright interior with an easy-living, one-level floor plan. A new deck is under construction and will be completed on or before 11/30/24. Enjoy the morning sunrise and beautiful light throughout the day, and soak in the captivating sunsets poolside. In the words of Debussy...there is nothing more musical than a sunset and the long western views will not disappoint. Let your eyes wander across the beautifully manicured, verdant lawns, providing a sense of both peace and privacy. This property is the perfect escape from city life but also allows one to venture out to local attractions: Refresh at the Roxbury Falls, enjoy local fairs and art shows, hike at Roxbury land trust, or try tennis, horseback riding and golf nearby. Shop at local Farmers markets and farm stands or go antiquing in neighboring Woodbury. Choose from a broad spectrum of dining options from farm to table to Michelin star restaurants. Just 1.5 hours from NYC.

Absolute peaceful, quiet and private Paradise with views and endless Possibilities. Immerse yourself in tranquility with this custom-built 5 bedroom Cape Cod estate boasting 900 feet of private frontage and captivating seasonal vistas. This expansive property offers the ultimate in privacy and flexibility, perfect for multigenerational living, entertaining, or simply enjoying the peace and quiet. Unwind in the grand entry foyer, leading to a dramatic great room with a soaring ceiling and a wall of windows showcasing the property's breathtaking beauty. The open concept floor plan seamlessly connects the great room to a chef's kitchen featuring a granite island, breakfast nook, and abundant cabinetry. Step out onto the expansive new 55-foot deck, ideal for al fresco gatherings with stunning seasonal views as your backdrop. The main floor master suite provides a haven of relaxation with a luxurious bath and an oversized walk-in closet, accompanied by a convenient home office. Upstairs, two generously sized bedrooms share a full bath, while one boasts an additional bonus space ideal as a playroom or extra office. This exceptional property caters to extended family or guests with a dedicated in-law suite accessible both from the main house and through its own private entrance. This self-contained haven features a four-room layout, including two bedrooms, a cozy living room with a fireplace, and a spacious kitchen with a dedicated dining area. The possibilities are endless..

Situated in the picturesque town of Roxbury, Connecticut—a mere 90 miles from midtown Manhattan—White Tail Farm epitomizes the pinnacle of New England living. This exceptional 86-acre estate is anchored by a c.1790s farmhouse that was restored in 1997 by Roderick Thorne, the esteemed builder of the renowned Mayflower Inn and Spa. In 2003, the property underwent a substantial renovation and expansion, resulting in a spacious residence that artfully combines historical elements with modern amenities. Ideal for discerning individuals seeking a private sanctuary or a multi-generational family compound, White Tail Farm offers an unparalleled living experience that balances rural serenity with convenient access to New York City. Main Residence: The 5,600+ square foot main residence seamlessly integrates period details with modern comforts. Wide plank oak flooring, beamed ceilings, six fireplaces, including wood-burning hearths in the formal living and dining rooms, create an inviting atmosphere throughout the home. The heart of the home features an open-concept kitchen and family room, equipped with premium appliances from SubZero, Wolf, Miele, and Viking. An informal dining area, framed by expansive windows, offers captivating views of the estate's rolling landscapes and memorable sunsets. The upper level comprises two primary suites, each boasting en-suite bathrooms, walk-in closets, dual vanities, soaking tubs and stall showers. One suite is fitted with a fireplace and bespoke built-ins. Two additional bedrooms, including another en-suite, and a guest room with panoramic southwestern vistas, provide ample, private accommodation for family and guests. The lower-level Great Room serves as an ideal space for recreation or movie nights. Amenities White Tail Farm caters to diverse interests and pursuits. Outdoor enthusiasts will appreciate the heated gunite pool, tennis court, and basketball/sports court. A covered porch overlooks the expansive lawn—a stunning 4-acre meadow surrounded by woods—perfect for al fresco dining or quiet contemplation. The property's trails offer excellent opportunities for hiking and snowshoeing, allowing residents to fully immerse themselves in the natural beauty of the estate throughout the year. Guest House Adjacent to the pool, the 1,890 square foot guest house exemplifies flexible luxury living. Its open floor plan encompasses combined living and dining areas, complemented by two wood-burning fireplaces. The recreation room, featuring French doors and a wall of windows, currently serves as a home gym. A well-appointed kitchenette and a private bedroom with an en-suite bathroom round out this adaptable space. Whether hosting guests, enjoying family time, or seeking a private retreat, this multi-functional building adapts to your needs. Moreover, it offers an ideal live-work space for those seeking a separate home office or studio. Natural Splendor The estate's 86 acres of unspoiled land invite exploration and appreciation of nature's beauty. The landscape design, masterfully crafted by renowned landscape architect Robin Key of RKLA—known for her work on New York's iconic Tavern on the Green—perfectly complements the natural surroundings. Highlights of the property include both banks of the pristine Battle Swamp Brook; a tranquil 1/4 acre spring-fed pond; meticulously curated landscaping with specimen plantings and mature trees, including a majestic sugar maple; winding trails ideal for walking, hiking, snowshoeing, equestrian activities, or recreational vehicle use; a stunning 4-acre meadow surrounded by woods, offering a picturesque setting for outdoor activities and events. Additional Features 9ft ceilings throughout, excluding formal dining room at 7'8 3-car heated garage 980 sq ft in-law/staff apartment above the garage 4-stall barn with electricity and water, perfect for equestrians or automotive enthusiasts Solar panels for sustainable energy efficiency Electronic fencing on the property for pet safety and freedom Recent significant upgrades include: new well pump, garage doors, siding and cedar roof on Pool House, and smart home technology Prime Location Accessed via a winding driveway at 62 Davenport Rd in Roxbury, White Tail Farm offers both seclusion and convenience. This estate presents a rare opportunity to own a piece of New England's pastoral elegance, perfectly suited for those who value privacy, architectural integrity, and seek a canvas for creating lasting memories.

FoxCroft exudes simple elegance. She stands proudly mid block on South Street, the center of town where children bounce house to house trick or treating. Tucked on this quiet street lined with giant gracious old Maples, Oaks and stone walls. It appears time has stood still in Roxbury, in the very best way. The property is rare in that it seemingly has space for everything. A heated pool, studio, large three car garage, guest house and pond. Also giving clues to its past: an ice and well house. This house is short on nothing. Most of all, charm. This 1792 Colonial Farmhouse has certainly stood the test of time, and oh, the stories it would tell. Enter into the living room flanked by two massive fireplaces, lit up by a grand window. It's easy to imagine spending holidays with the fireplaces blazing. The dining room provides a moody space to enjoy dinner in front of yet another intimate fireplace, hewn beams accent the ceiling. The sunroom provides a space to read a book on a Fall afternoon surrounded by windows filled with the changing colors of the season. Built in bookshelves stand at the edge of the space for decor and beloved trinkets. The chic and updated kitchen provides modern amenities including a six burner Viking stove and a SubZero refrigerator. Connected to the kitchen is a pantry with ample storage and a place to tuck away kitchen goods. A front and back staircase connect you to the second level. Upstairs has three bedrooms and a bonus space. The primary has an ensuite bath. Guests will enjoy their choice of two other bedrooms, one with a connecting ensuite bath and fireplace. The other with a fireplace and its own full bath down the hall. The darling guest house was once a one room school house. Enter and prepare to be awestruck. The gray and white checkered floors, wood burning fireplace and sunny sitting room is both charming and functional. The space also includes an additional bedroom, small kitchenette and full bath. The heated pool provides a space of both entertainment and retreat on the property. Beyond the pool are perennial gardens and the original ice house that could be used for garden storage or a playhouse. The studio provides the ultimate work from home space. The dry erase material adorns the walls for note making, and brainstorming. The space has high ceilings and hewn beams and ample light. The attached half bath also has an additional washer/dryer. The property gives space to explore. Head to the pond through the perennial gardens. Or hike through the back field through your own meadow of serenity. FoxCroft beckons its next steward to begin its next chapter.

Nestled on one of the most picturesque roads in the region, straddling the border of Washington and Woodbury with views of nearby foothills, this extraordinary 1837 antique barn-style home is a perfect blend of historic character and modern comforts. Surrounded by major estates and bordered by the Steep Rock Land Trust on two sides, the property provides unmatched privacy and tranquility, with western-facing views over protected land. This 3-bedroom, 2.5-bath home w/1 br guest apt, features an open-concept floor plan, showcasing exposed beams, original charm, and high-end finishes. The vaulted living room is a true highlight, complete with built-ins, a wet bar, and an abundance of natural light that floods the space, creating a warm and inviting atmosphere. The spacious primary suite is conveniently located on the main level, which is a private retreat with an en suite bath, ensuring both comfort and privacy. A separate guest house adds to the property's appeal, providing additional living space ideal for visitors or extended family. Step outside to discover a stunning pool area with a stone terrace that overlooks the expansive level lawn and breathtaking western views. Whether you're entertaining or simply relaxing, this outdoor space is designed for enjoying the natural beauty of the surrounding countryside. The property has ample space for privacy, gardening, or additional outdoor activities, with Steep Rock Land Trust protecting the neighboring land

NOW, WITH 4 BEDROOMS IN THE MAIN HOUSE AND 2 BEDROOMS IN THE GUEST HOUSE. THE 2200 FT MAIN HOUSE ALONG WITH AN ADDITIONAL 1500 FT PRIVATE HOME! A long driveway winds you into this idyllic retreat with western views and sunsets, nestled minutes from town. This stunning Cape Cod Farmhouse thoughtfully constructed has been expanded to include two additional bedrooms in the Main House. An additional 780 ft of Lower Level walk out unfinished space boasting high ceilings is ready to finish as well. It is a harmonious blend of modern comfort and classic charm. The open floor plan invites effortless flow, while French doors beckon you to the expansive deck where western sunsets paint the sky. Inside, discover the allure of a gourmet kitchen with central island, perfect for culinary adventures and casual gatherings. Beyond the main house, a charming 1500 two-bedroom guest house adds versatility and privacy. The oversized two-car garage completes this exceptional property, providing ample space for your vehicles and storage. Enjoy open-concept living that seamlessly flows to a grand deck, where you can unwind while taking in breathtaking western sunsets over the neighboring horse pasture!

Modern Farmhouse Oasis on 4 Acres in Peaceful Roxbury. A winding drive leads you to the home, where elegant stone steps guide you to a covered porch, surrounded by a lush perennial garden. Inside, the sophisticated living room features French doors, grasscloth wall-covering, and crown molding. This seamlessly connects to a formal dining room with tray ceiling and a bay window. The heart of the home is the recently refreshed eat-in kitchen, equipped with modern appliances, bar seating for four, a large pantry, access to a large deck and a custom-built office nook ideal for multitasking. The great room offers comfort and style, centered around a large wood-burning fireplace with an ornate mantle that complements the home's beautiful millwork. Custom built-in cabinetry with inset lighting and a recessed ceiling enhance the charm of this space. Upstairs, the primary suite is a private retreat, complete with a walk-in closet and an oversized bath featuring a jetted tub and walk-in shower. The upper level also includes a linen closet, shared bath with dual vanities + bathtub, and 3 generous guest bedrooms, each with its own closet. The lower level provides access to a 3-bay garage and a large workshop with exterior access and ample natural light-perfect for a workshop or potential additional living space. Meticulously maintained; new roof, exterior paint, AC + Furnace in past 3 yrs. Ideally located, you are mins to Woodbury, Southbury and all Litchfield County has to offer!

Quintessential Roxbury Cape with detached studio space on a quiet road across from 300+ acres of Roxbury Land Trust and hiking. Enjoy modern amenities and unparalleled privacy in this serene setting with abundant windows and French doors that fill the space with natural light. Step inside to an open floor plan through an entry featuring custom built-ins and stone flooring, leading to a living room and dining area with intricate paneling. The updated kitchen, with breakfast bar, offers stunning views of the preserve, stone walls, and access to a large deck perfect for outdoor entertaining. The main floor primary suite includes a marble bath with dual vanity and opens to a flexible space-ideal as an office, den, dressing room, or additional guest space. Upstairs, find two bedrooms and a spacious bath with a window overlooking the grounds. The larger bedroom features vaulted ceilings and a large walk-in closet, offering potential for an alternative primary suite. The walk-out lower level adds living space and storage, while the heated and cooled studio above the garage is perfect for a home office, artist's studio, or potential guest retreat. Outside, manicured grounds boast local granite hardscaping, including a stone patio and sculptural steps leading to the studio. Ideally located with hiking trails out your door and proximity to Washington Depot, Woodbury, and New Milford! Agent/owner.

Historic Washington Cottage. There is a timeless elegance in this charming 1912 cottage with wood shingle roof and log exterior, which creates a haven on the 5 private acres. Situated off Wykeham Road, this historic gem gives tranquility and convenience, just moments from the Washington Green and the renowned Mayflower Inn. The cottage's captivating living room with it's soaring cathedral ceiling and a cozy stone fireplace, evokes a sense of warmth and nostalgia. The updated kitchen blends modern amenities with the home's original character. The primary sleeping area is currently a small loft area, which is accessed by a ladder, and provides a unique and cozy retreat. The full bath, which is split, with sink in a separate room creates European ambiance. A convenient laundry/utility room completes the functional layout. A recently constructed 2 level garage with a metal roof gives ample storage space and potential for future expansion. Enjoy the privacy and serenity of this idyllic setting, perfect for outdoor enthusiasts and those seeking a peaceful escape.

Complete Privacy in Bridgewater on 11+ Acres. Enjoy light-filled open concept space in a stunning setting which features a brook, rolling stone walls and a private drive. The main level offers a bedroom, full bath, laundry room and double height ceilings in the main living room. The second floor boasts a primary with vaulted ceiling, additional bedroom, full bath, and a cozy loft ideal for an office or reading nook. Other highlights include a detached barn with parking for two cars and a storage room above. The house has a full basement with walkout access as well. Wander trails throughout the 11+ acres that open to the brook and circle the expansive land. This property is a rare find, offering complete privacy while being conveniently located just 90 minutes from NYC. Explore nearby Bridgewater and Roxbury centers, local land trusts, shopping, and dining options.

Stone Bridge. The Ultimate Classic Country Estate with Modern Amenities. Impeccable Stone and Shingle home, set on 24.9+ private bucolic acres in the highly desirable Nettleton Hollow area in Washington, CT. Elevator to all Floors. Architect-designed and built by HOBI Award Winning, Corbo Associates, this 7000+ sq ft, with additional finished 3100 ft on the lower level is graced with 5 bedroom suites, including first and second floor master suites, state of the art easy care systems and heated gunite pool. The public spaces open on to terrace and covered patio space to bring the outdoors in. Garaging for 3 cars via porte cochere to a second garage. Privately set off the the road with a meandering driveway which overlooks a nearby pond, the elegant and comfortable spaces throughout flow from house to patio and pool. Soaring ceilings and glass bring the outdoors into every room. Sprawling spaces for entertaining with 7 fireplaces, elevator, library, home theater, game room, 1500 bottle wine cellar and tasting room, sound dampened walls, generator, central vacuum, home technology and security system. A top of the line kitchen is the center of the home with an additional butler's kitchen for entertaining. Top rated construction and energy efficiency, using state of the art geothermal heating and cooling system and Cat 6 audio wiring for sound, data and internet. The manicured grounds with mature plantings and stonework include an irrigation system. Magnificent Country Estate!

A once in a lifetime opportunity to own over 230 acres overlooking Lake Waramaug. Nestled high in the hills overlooking the pristine beauty of the lake, this offering comprises six parcels of open fields and forest with exceptional views. Owned by the same family for the last 70 years, dignitaries from the worlds of art, politics, and industry have been entertained here while the stables, paddocks and trails have been home to thoroughbred racehorses and generations of equestrians. This property includes two vintage main houses, a guest house, a guest cottage, an in-ground pool with pool house, and staff quarters attached to a twelve stall stable and carriage barn. Miles of footpaths and trails lead to natural springs, a seasonal pond and streams, and a rocky outcropping archaeologists believe was used as a shelter by native settlers. Located in the heart of Litchfield County, within two hours of Boston and Manhattan, this is the ideal opportunity for those that appreciate the history and grandeur of a property of this caliber.

The perfect blend of classic charm and modern living with this beautifully remodeled, Colonial style home - nestled on a generous 1.33-acre lot. As you step inside, you're greeted by the warmth of wide plank wood flooring that flows seamlessly throughout. Culinary enthusiasts will delight in the chef's kitchen, equipped with a double oven six-burner gas stove, Subzero fridge freezer, Miele d/washer, soapstone countertops, a chic farmhouse sink and a convenient breakfast bar for casual dining. Adjacent to the kitchen lies an elegant dining space, complete with a built-in buffet, ideal for hosting memorable dinners. The living room is a haven of natural light, offering a tranquil space to unwind or entertain guests. Step outside to the expansive flagstone patio, with a huge fire pit perfect for al fresco gatherings or simply to enjoy the serene surroundings. Upstairs, the home boasts a primary bedroom with walk-in closet & 2 further bedrooms with Queen beds & generous closets. Each room offers a peaceful retreat, complemented by a stylish brand new full bath with double vanity that exudes timeless elegance. Finished attic and L/L den with French doors. Brand new HVAC & ductwork across the 4 levels, Central air and electrical service (all in 2023). Located just minutes from the vibrant Depot Center - the heart of Litchfield County's finest! Indulge in local shops, restaurants, art galleries or explore the natural beauty of the Shepaug River, Lake Waramaug & Steep Rock Preserve. Additionally, this property comprises a lovely, level yard which has a small pond and a brook to the rear. There is plenty of parking and a detached garage and barn for the convenience of storing outdoor equipment.

Step into tranquility with this stunning 4 bedroom, 3.5 bath home designed to elevate your state of calm. Nestled between exquisite gardens crafted by an artist family, this property offers a pure zen- like atmosphere for those seeking peace and beauty. Beyond the serene gardens is the home designed to take advantage of its surrounds. The living room features a double-sided fireplace offering scenic views of the gardens and flows into the island kitchen with dining area and abundant storage. The formal dining area is ideal for larger gatherings. The remodeled bathroom is a true spa experience with soaking tub, open shower and lush plants. In addition to four bedrooms, there is a bonus room for possible study, home office, gym or meditation space. There's much more to explore making this a must see for anyone looking to live in a peaceful and inviting environment.