luxury house with pool for sale Canaan, United States

Commanding one of the highest residential elevations in the Hudson Valley, this extraordinary custom residence enjoys breathtaking, uninterrupted views across the Catskill Mountains and Hudson Valley, offering spectacular sunsets, endless skies, and extraordinary stargazing from the privacy of your own mountaintop retreat. Thoughtfully designed for luxurious everyday living and effortless entertaining, the home features a chef's kitchen appointed with premium Bosch, Sub-Zero, and other high-end stainless steel appliances, a gas cooktop, a handsome butler's bar, and exceptional custom cabinetry and built-ins handcrafted by renowned local artisan Vormer Cabinetry of Hillsdale. Superb craftsmanship is evident throughout, complemented by high-performance insulated Pella windows that enhance comfort and energy efficiency while framing the spectacular views. The dramatic great room is anchored by a striking stone fireplace with a reclaimed wood mantel, while a marble gas fireplace with a wood mantel creates an inviting atmosphere in the den. The spacious primary suite enjoys magnificent views and is complemented by an open spa-inspired bath, laundry, and generous closet space. The spacious two-car garage offers abundant storage for outdoor equipment, bicycles, paddleboards, and kayaks, perfectly complementing the property's proximity to Queechy Lake, Stockbridge Bowl, and the region's exceptional outdoor recreation. Modern conveniences include app-controlled security cameras and heating and cooling systems, allowing effortless remote management of the home. Outdoor living is equally impressive, with expansive decks and patios positioned to capture the extraordinary views, multiple barbecue and fire pit areas, and a heated saltwater swimming pool creating an exceptional setting for entertaining or quiet relaxation. A charming pool house with its own outdoor grilling patio extends the outdoor living experience, while the walkout lower level opens to an additional stone patio and fire pit--another spectacular vantage point from which to enjoy unforgettable Catskill sunsets beneath expansive evening skies. Raised garden beds, ornamental flower gardens, and fenced vegetable gardens with programmable drip irrigation provide an ideal setting for growing vegetables, herbs, and flowers. Flexible living space offers additional guest accommodations, while a backup generator provides year-round peace of mind. An additional five-acre parcel is included in the sale, presenting an exceptional opportunity to construct a guest house, studio, office, or other accessory structure, subject to approvals. Located within an exclusive community with privately maintained roads, the property offers exceptional privacy while remaining just minutes from Chatham, Hudson, and the Berkshires. Enjoy easy access to acclaimed dining, boutique shopping, yoga and Pilates studios, organic markets, farm stands, theater, antiquing, and renowned cultural destinations including Tanglewood, Jacob's Pillow, Stockbridge, Lenox, Egremont, Great Barrington, and the Shainman Gallery. Convenient to the Taconic State Parkway, Interstate 90, New York City, Boston, and Albany International Airport, this remarkable residence offers the very best of Hudson Valley luxury living.

Welcome to Red Rock House, a remarkable architectural compound privately set on 16 acres in the historic hamlet of Red Rock in East Chatham, New York. Designed by Anmahian Winton Architects with landscapes by Studio Reed-Hilderbrand, this extraordinary retreat seamlessly blends contemporary design with the surrounding natural landscape, creating an exceptional sanctuary. A winding driveway through the forest leads to the main house and guest house, both clad in darkened cedar wood with latticed privacy screens that blend effortlessly into their surroundings. A bluestone pathway connects the structures, leading to a terraced pergola with multiple seating areas, a wood-burning fireplace, sweeping meadow views, and a 60-foot heated saltwater pool. Just beyond, a secluded cottage overlooks a rushing creek, while a woodland trail leads to an elevated treehouse-perfect for yoga, meditation, or quiet reflection. Spanning three levels, the main house is a masterclass in modern minimalist design. Crisp white interiors create a gallery-like backdrop for art while framing spectacular four-season views through expansive walls of glass. A stone-paved foyer leads to a dramatic loft-like entertaining space anchored by a double-height living room with floor-to-ceiling windows overlooking the treetops. Nearby, a cozy lounge with a wood-burning fireplace opens to a wraparound terrace cantilevered into the forest. The windowed chef's kitchen with center island flows seamlessly into the dining area and features Vermont Danby marble countertops, abundant custom cabinetry, premium appliances by Wolf, Sub-Zero, and Miele, plus a balcony overlooking the pool and meadow. A tasteful powder room completes this level. A sculptural staircase leads up to the private primary suite level, an airy retreat filled with natural light. The king-sized bedroom includes a sitting area with a gas fireplace and a spa-like bathroom with double vanities, a rain shower, and a deep soaking tub for two. A spacious dressing room with custom built-ins offers exceptional storage, while a hallway with a laundry closet leads to a comfortable media room featuring a fireplace and custom bookshelves. The walk-out lower level opens directly to the pool and includes two bedrooms, a study, and a full bathroom. These flexible spaces can also serve as a gym, home office, or studio. A large mechanical room is also located on this level. Privately positioned from the main residence, the contemporary guest house offers bright open living spaces, oversized picture windows, two spacious bedrooms, a full bathroom, and a kitchenette. Below, a two-car garage provides abundant storage and a Tesla charging station. The entire compound is meticulously maintained and offers exceptional privacy and premium amenities, including multi-zone HVAC, radiant heated floors, custom architectural lighting, a central vacuum system, and a 22KW generator for the ultimate in comfort and security. This unique and remarkable offering is ideal for those who appreciate world-class modern architecture and are seeking a true refuge from the world outside. Though completely immersed in nature, the property sits just 10 minutes from the town of Chatham and 25 minutes from Hudson and the Berkshires, with easy access to renowned restaurants, farmers markets, Tanglewood, P.S. 21, and the highly anticipated Art Omi Pavilions. Red Rock House: not just a home, but a holistic and restorative experience!

This architectural gem has been carefully restored and enhanced to exceptional standards, preserving its storied heritage while seamlessly integrating contemporary conveniences. The exceptional property features an elegant Main House, inviting Guest Cottage, Potting Shed/Studio and Barn. Framed by breathtaking panoramic vistas, the estate showcases classic stone walls, a serene spring-fed pond and a heated saltwater pool. The impeccably maintained lawns and expertly designed grounds establish a pristine country retreat. Premium upgrades include superior rock wool insulation throughout. Perfectly positioned just minutes from Tanglewood's celebrated performances, fine dining and thriving cultural attractions in the Berkshires.

Experience the perfect balance of grand-scale architecture and tranquil nature in this stunning 6,000+ sq. ft. modern Colonial. Nestled on 3.42 manageable acres within a private enclave near Onota Lake, this 5-bedroom, 5.5-bath estate offers sweeping meadow views just minutes from the world-class arts of Tanglewood and The Clark. The entry is marked by dramatic dry-laid stonework, leading into an interior defined by soaring heights. The heart of the home is a two-story living room featuring vaulted ceilings and a floor-to-ceiling stone fireplace. The expansive living space of the great room flows effortlessly into a gourmet chef's kitchen equipped for high-end entertaining with dual refrigerators, double wall ovens, and a center island cooktop with a built-in griddle. High-top island seating allows for social cooking and a sizable breakfast area flanked by a wall-to-wall credenza—ideal for buffet-style hosting. The home's floor plan thoughtfully blends communal areas with distinct privacy across three levels. The main level is designed for complete convenience and the primary suite is a true sanctuary. It features a private egress to the pool and a hidden back staircase leading to a secluded loft—perfect for a library or reading nook overlooking the suite. The upper level offers a sweeping gallery balcony overlooking the great room, leading to four spacious bedrooms. This includes two private ensuites and two additional bedrooms serviced by a full bath and a dedicated laundry room. The lower level is an entertainment hub featuring a home theater, gaming space, gym, full bath, and a secondary egress for easy garage access. The fully-fenced backyard makes for a resort-style oasis. Host movie nights on the expansive deck, or relax by the heated inground pool and custom-finished patio. The designer firepit is anchored by a unique stone compass inlay, and a poolside full bathroom ensures guests never need to track water through the main house. For the automotive hobbyist or enthusiast, a high-end, three-bay attached garage is professionally finished with epoxy floors, industrial-style metal cabinets, and an EV charger. You will also find a massive, 50x40 detached shop with four bays and oversized doors. Whether for housing a car collection, an RV, or a professional art studio, the possibilities of this space are endless. Embrace the Berkshire landscape in a home where every detail has been considered. Whether you are heading out for fine dining or staying in to enjoy your private oasis, Blythewood Estates offers a lifestyle of unparalleled peace and sophistication.

A Classic Modern Farmhouse with Incredible Views - This home has been thoughtfully updated to provide a seamless blend of style and comfort. The property features a resplendent in-ground pool, a spacious swim pond, and a three-car garage with an inviting guest suite above.The main residence welcomes you with a charming wrap-around porch and an enchanting screened porch, both perfect for enjoying the dynamic and ever-changing views. The interior is bright and lively, with each space thoughtfully designed to capture the natural beauty of the surroundings.The gourmet kitchen, a convivial hub with a grand stone fireplace, offers direct access to the screened porch and serves as the perfect backdrop for culinary exploration and social gatherings. The first floor also includes a welcoming foyer, a serene bedroom suite, and an elegant formal living room.Upstairs, the master suite is a haven of sophistication, complete with a stone fireplace and ample space for relaxation. Two additional guest bedrooms share a Jack and Jill bathroom, providing comfort and privacy for friends.The finished lower level is dedicated to leisure and repose, crafted with the ultimate goal of relaxation in mind. Here, in this tranquil setting, you'll find the peace and privacy you desire, all within a home that exudes charm and character.

The Wheatleigh: A Gilded Age masterpiece on over 21 pristine acres overlooking the Stockbridge Bowl. Designed in 1893 by Peabody and Stearns, this Florentine palazzo features stunning grounds by Frederick Law Olmsted. Former home to the Boston Symphony Orchestra and moments from Tanglewood, this 25,000+SF architectural sanctuary seamlessly marries timeless grandeur with 21st-century luxury. The majestic layout boasts a soaring Great Hall, a formal dining room, a refined wine cellar (6,500-bottle capacity), and 19 uniquely curated bedroom suites. Breathtaking porticos frame panoramic vistas, while rolling lawns and mature gardens present paths to the pool and tennis court. This iconic estate offers utmost privacy, a deeply rich cultural heritage, and unmatched Berkshire elegance.

This stylish log home on 3+ acres is the complete Berkshire retreat. Recently updated and improved, the home pairs modern lodge character with resort-like amenities. A heated saltwater gunite pool and integrated hot tub anchor the beautifully landscaped grounds. A locust fence encloses the pool area, with bluestone patio, lush lawn, and a stunning renovated pool house designed for entertaining, dining, or remote work. Inside, the home is warm, open, and full of character, with the added benefit of true one-level living. The great room is the centerpiece, with soaring ceilings, exposed log beams, and a substantial stone fireplace. The adjoining kitchen and dining areas are designed for gathering, with cherry floors, custom pine cabinetry, a large island, and stainless appliances. A large screened porch and wraparound deck extend the living space outdoors and take in the wooded setting and ridge views. The luxurious first-floor primary suite offers private porch access and a spacious bath with soaking tub and separate shower. First-floor laundry completes the main-level living arrangement. Upstairs are three additional bedrooms and two full baths. The walk-out lower level includes a dedicated home gym and additional flexible space. Beyond the pool area are several other amenities, including a dramatic fire pit tucked into a natural rock outcropping, a children's playground, and open lawn for games and play. Private but not remote, the property is just minutes from downtown West Stockbridge, with Stockbridge, Lenox, Great Barrington, and Tanglewood all within easy reach.

Gracious colonial style home in the heart of the southeast historic neighborhood minutes to upstreet cultural art and theatre district with museums, galleries, theatres, eclectic dining, and more. This home awaits your finishing touches is search of a new homeowner with a sense of style and interior design to make this beauty the show piece it deserves to be. Abundance of living spaces on multi levels, finished attic for six bedrooms boasting three full baths and one half bath. Modern kitchen and primary bath give you the start you need. New hot water baseboard heating system and incredible front yard that is edged in custom cut marble for easy care maintenance. Lower level walk-out offers more space for exercise, crafting and workshop space. Incredible oversized yard for fun and enjoyment

Located in Stockbridge, this historic General Williams House (circa 1795) has been restored and updated. Featuring 6 bedrooms, 5.5 bathrooms, 6 beautiful wood burning fireplaces, large dining and living spaces and 2 kitchens. The ''Ice House'' features its own kitchen and bath, for family gatherings or as Artist Studio. A sparkling in-ground pool for your summer pleasure. All this and more exists close to Main Street Stockbridge, Norman Rockwell Museum, Tanglewood, and all the most important cultural amenities. Who could ask for anything more?

Charming in-town Cape on a spacious lot with inground pool. Located in a delightful neighborhood close to town, this inviting home built in 1951 offers 5 bedrooms and 2 full baths. Inside, the residence seamlessly balances ample room to spread out with warm, light-filled spaces tailored for everyday living and entertaining. Timeless architectural details throughout bring character and charm, including a wood-burning fireplace, graceful arched doorways, and custom built-in cabinetry. Outdoors, a private in-ground pool is set within a large, sunny yard, creating a wonderful oasis. Turn-key peace of mind is provided by recent upgrades, including a newer furnace, water heater, and pool filter. Town water, town sewer, and natural gas from the street. Close to everything; a must see!

Experience the luxury of gracious proportions, impeccable details, and stunning design in this exquisite classical villa that would be as at home in Italy as it is in the Berkshire landscape. Protected views of mountains, rolling hills, and meadows surround the 6.9-acre estate. The atmosphere of sophisticated luxury begins with the approach through an allee of willow trees and in the front courtyard, edged with stately Bradford pear trees and arbor vitae and anchored by the 2716sf, single-level residence and a matched pair of outbuildings--a two-car garage and a garden house. The front entry of architect-designed residence leads to a luminous interior with tall ceilings, reflective white walls, generous windows and 19 screened French doors that welcome sunlight and breezes and provide for ideal interior-exterior living. To the left of the entry are a living room with a wood-burning Rumford fireplace and hallway to the primary suite with an airy, comfortable bedroom, refined, restorative bath, and walk-in closet/dressing room. To the right, a spacious dining room, well-appointed kitchen, screened porch, and hallway to two bedrooms and full bath. The U-shaped floor plan embraces a secluded formal garden, reflecting pool with fountain, patio with pergola, and 40' lap pool. Completed in 1998, every element of the residence attests to architectural intelligence, superior craftsmanship, and love for the bucolic landscape. The high level of quality is evident in the visually commanding millwork, true stucco exterior, lath-and plaster walls in the principal rooms, east and south pergolas, west-facing screened porch, and sensitive choreography of space. With roots in the classical architecture of ancient Rome, this is a thoroughly modern dwelling replete with whole-house fan, air conditioning, generator, security system, 630-foot drilled well, and chef-ready appliances. The result is a home that feels both sculptural and deeply connected to its setting. With protected views, total privacy, and proximity to South County amenities (7 minutes to Guido's), this is a rare Berkshire offering -- serene, architecturally stunning, and eminently livable.

Tucked away at the end of a private cul-de-sac on 1.22 acres, this 4-bedroom, 4-bathroom contemporary home delivers sophisticated Berkshire living just minutes from downtown Great Barrington. Offering the perfect footprint for full-time remote professionals, weekend escapees, or downsizers, this property pairs a spacious layout with the effortless lifestyle of a premier community association. The heart of the home is a dramatic, light-filled great room anchored by soaring cathedral ceilings and a brick fireplace paired with charming built-ins. The main level is designed for entertainment and ease, featuring a lavish first-floor primary suite with walk-in closets and a spacious ensuite bath. Upstairs, three additional guest bedrooms are complemented by a private, separate bonus studio above the den--offering an ideal, quiet space for an executive home office or fitness room. Outdoor living is built for relaxation, featuring an expansive wrap-around deck with scenic views, a stone patio, and a spectacular 3-season screened porch overlooking mature perennial gardens. Modern mechanicals include central air and a full backup generator system for ultimate peace of mind. As a resident of this coveted neighborhood, you'll enjoy exclusive access to the heated community pool. Simply lock up, leave, and enjoy nearby Tanglewood, local ski mountains, and Main Street dining.

Fantastic opportunity to own a home in a peaceful cul-de-sac within the desirable Cornwall Estates. This lovely home sits on a level lot with almost 2.5 bucolic acres. Spanning just over 2,000 square feet, the home features a convenient first-floor primary bedroom and bathroom, vaulted ceiling in the living room and a screened in porch that leads to a large, partially fenced in backyard. Many recent updates and upgrades including kitchen and bathrooms, as well as the furnace and central AC system replacement. All of this and a heated community pool nearby and Great Barrington just minutes away, make this home ready for its next owners to create their own Berkshire journey and memories. Replaced/Updated Within the Last 3 Years: furnace, central AC, kitchen, bathrooms, all exterior doors, basement improvements Community Details: -8 homes in the community -$1,500 transfer fee due at closing from buyers to the Association -HOA dues will decrease to $900 per quarter ($300 per month) after two loans are paid off in July and October 2027 Rental Policy: -First rental term has a 28-day minimum -Second rental term has a 7-day minimum -Maximum rental term is 1 year -Lease extensions must be approved by the Association

Built in 1974 by an engineer, this mid century modern residence resembles a French chateau in concept yet retains all the modern flourishes true to the period. Once two identical houses then combined employing steel beam construction, the symmetry inside soothes the soul of the connoisseur but it is the 12’x 60’ lap pool and accompanying screened pool house that grabs the attention. Surrounded by hedges of hydrangeas and a tidy boxwood garden that lends to the European flair of this property, florals fall over all the edges of the sensational long lawn while providing a tucked-in experience of privacy. This 3 bedroom 2 bathroom house boasts lofty, two story atriums with dramatic, modern glass windows with vertical mullions casting inviting sunlight over the living spaces while the whole house white painted interiors add a lightness of being within all the rooms. The open kitchen with its mid mod mosaic tiles offer the clean lines you come to expect from this architectural specimen while also being warm and entertaining. This property is especially good at throwing parties as it lends itself to both indoor and outdoor lifestyle activities with patios in both the front and back lawns. Stuyvesant NY is a scenic, rural town tucked away in the northwestern corner of Columbia County. It is defined by its pristine agricultural landscape, deep-rooted Dutch history, and striking waterfront geography along the eastern shore of the Hudson River, all the while enjoying its unique proximity to the village of Kinderhook NY. Shop for CSA farm to table foodstuffs at Samascot just 5 miles away or hit up the Chatham Berry Farm for your groceries and never step foot into a box store again. Dining out in the evening is provided by the many lovely Kinderhook hotspots.