luxury houses for sale Pine Plains, United States

Call it grand, call it groovy, this one-of-a-kind 8,000+ SF estate encompasses a meticulous 1810 Federal manor with whimsical 70s-style wing that's true entertainment nirvana. Infinite space for a compound, guests, work from home or perhaps reconceived as a luxury inn----and all with a breathtaking gentleman's farm attached. 147 acres of rolling lawns, mature trees, ponds, pastures, pool and greenhouse with multiple potential building sites. Did we mention the stunning Catskill views? Imagine kicking off your gatherings by the textured gold fireplace in the spacious sunken living room in the Modern wing before mounting a few steps to the cavernous indoor pool with lounge and then on to the conservatory deck for sunset (or sunrise) cocktails. Nearby is a free-standing staircase (with original Corning glass blocks) up to 1500 SF primary suite with spa bathroom with dual sinks and dual dressing rooms. Back on the ground floor, an open plan multi-colored kitchen with exposed beams, frosted glass counters and sycamore cabinetry spills into a dining area and wetbar. A stunning rear breezeway with exposed beams and wall of windows serves not only as informal dining room but as connector to a comfy media room and the Federal-era part of the home. The finely-appointed Federal wing, a traditional center hall Colonial, is a favorite for guests, with 4 cozy bedrooms, ensuite bathrooms, and charming sitting and dining areas. A beautiful blue stone terrace leads to the pool and poolhouse with wood burning fireplace that can easily be reimagined as an apartment, office or party barn. Nearby is a 5-bay garage for a serious car collection. So much land, so much potential! With multiple parcels and prospective building lots, there's also agricultural options: Currently there are grazing pastures for Black Angus cattle and five acres of a black currant crop. When a meditation workshop beckons, head to the world-renowned Omega Institute in nearby Rhinebeck, also famous for farm-to-table restaurants. Craving culture? Architect Frank Gehry's celebrated Fisher Center at Bard only 15 minutes away. 2-hour drive to Manhattan. Bring your architect to Red Hook Farmstead and custom-design this into your dream house!

Mare's Nest ~ Circa 1890's equestrian property once home to many thoroughbred racehorses. This charming Colonial has been a cherished family home for over 50 years. The estate showcases a combination of period details and recent additions including a primary bedroom wing on the main level and a greenhouse. The main house boasts 4 fireplaces, 4 bedrooms and 5 baths. Fabulous heated in-ground pool and pool house located off the great room. Across the 27 rolling acres of lawns and pastures, the pastoral beauty of the landscape unfolds, offering a pond and a serene escape into nature. Outbuildings add to the charm and functionality of the property, with garages, 6 stalls and a paddock ~ the latter 2 for equine pursuits. A few minutes to the vibrant village of Millerton with great farm to table restaurants, the movie house, and shopping. Easy access to the rail trail for walking and biking. 2 hours to NYC.

Nestled in the serene beauty of Ancram's rolling landscapes, this stunning modern retreat offers a perfect blend of luxury and tranquility. A nearly new construction, 2020, this single-family residence is a delightful haven for first-time homebuyers, weekenders, or anyone seeking a peaceful country setting. Upon entering, you're greeted by an open and airy atmosphere, complemented by soaring cathedral ceilings that enhance the feeling of spaciousness. Enjoy quiet restful nights sleep in either of your two generously sized bedrooms. The heart of this home is undoubtedly its high-end kitchen, featuring state-of-the-art appliances and exquisite finishes, making it a joy for both the culinary enthusiast and casual cook alike. The adjacent living area is warmed by a huge stone fireplace, creating an inviting space for cozy gatherings or tranquil evenings. Beautiful ceramic tile floors adorn the entire first floor. Beauty meets function with the elegant bathroom renovations, boasting a soaking tub in the main bathroom, modern fixtures and pristine ceramic tile floors, while beautiful hardwood floors in the upstairs living spaces add a touch of timeless charm. Large windows frame enchanting views of the surrounding nature, inviting the outdoors in. Outside, the bluestone patio extends your living space into the fresh countryside air, perfect for your morning coffee in the sun, entertaining your guests or simply enjoying your amazing yard and woods. A detached oversized 1-car garage provides additional space, ideal for a studio or workshop. Added comforts include a state-of-the-art heating system and a sense of privacy that's increasingly hard to find. This property is a rare gem, offering the perfect blend of sophistication, comfort, and nature - a dreamy escape for those looking to downsize, make their first purchase, or secure a part-time sanctuary. Welcome to your idyllic home, where every day feels like a peaceful getaway.

Nestled in the heart of the Hudson Valley, this unparalleled 133 acre compound in Copake, NY is a masterpiece of luxury and sophistication. The sprawling private grounds are a haven of natural beauty, with serene water frontage on 46 acre Chrysler Pond, lush woodlands for outdoor adventures and farm facilities. Each corner of the property offers breathtaking mountain views and a sense of tranquility. The masterfully handcrafted 6-bedroom lodge, constructed with timber from British Columbia, offers over 8000 SF for year round entertainment. The residence exudes elegance with a chef's kitchen, gracious dining room and exquisite living room, complete with commanding fireplace crafted from local stone and vaulted beamed ceilings that seamlessly blends rustic charm with modern comfort. Additional features include breakfast nook, sunroom, outdoor kitchen and spa jacuzzi overlooking the Berkshire Hills. The meticulously designed one-bedroom pool house, salt water pool, USTA-grade tennis court, bocce court, shooting range and European spa with steam and sauna create a sanctuary for relaxation and recreation. The additional buildings are a testament to the estate's grandeur, featuring a three level 10,000 SF Barn with multiple floors for entertaining, showcasing prized vehicles and extensive storage. The second floor modern multi-purpose loft is suited for grand parties and guest accommodations. An additional large barn and various outbuildings cater to a range of uses. Additional acreage is available. Located within easy reach of Berkshire County and Hudson Valley's many attractions, this property is more than just a home - its a lifestyle.

Welcome to Two Arrows. Experience the epitome of elegance and luxury in this magnificent Williamsbug, Virginia-style estate, nestled in the picturesque hills of Ancram, NY. This stunning property seamlessly blends historic charm with modern conveniences, offering a serene retreat just a short drive from the hustle and bustle of city life. Step into a world of grandeur with this estate's classically inspired architecture. The meticulously designed exterior features including timeless stone facades and intricate masonry, evoke romantic allure. Inside, the estate boasts comfortable living spaces adorned with coffered ceilings , grand fireplaces, and exquisite finishes that reflect impeccable craftsmanship. The interior of this estate is designed to impress and comfort. Perfect for entertaining guests or enjoying intimate family gatherings. The eat-in kitchen is a chef's dream, equipped with top-of-the-line appliances and custom cabinetry. Retreat to the luxurious master suites, complete with ensuite bathrooms . Set on acres of manicured grounds, this estate offers unparalleled privacy and tranquility. Enjoy outdoor living at its finest with beautifully landscaped gardens. The property also features a charming guest house, perfect for accommodating visitors or providing additional living space. Each area of the estate is designed to be enjoyed throughout the seasons. Early spring mornings greet you with daffodils, crocus and grape hyacinth. As spring continues, you enjoy the lilacs and all the different fruit blossoms (apple, peach, pear, red splendor crabapple). The carefully trained wisteria erupts in bloom at the main house and garden house as the warm weather arrives. Enjoy the beauty of the formal parterre garden with its pink diamond topiary hydrangeas. Observe as the honey bees work diligently in the wildflower meadows and the hummingbirds drink from the trumpet vine. Late Summer and Autumn bring the bountiful harvest of peaches, apples and pears. Situated just two hours from NYC, this estate offers the best of both worlds: peaceful country living with convenient access to nearby amenities. Explore the scenic beauty of the Hudson Valley, enjoy local wineries and fine dining, or take a short drive to experience the cultural and recreational offerings.

Charming 3-Bedroom Spring Lake Cottage with 17 acres located in Red Hook, NY. This enchanting 3-bedroom, 1-bath cottage is surrounded by nature's beauty, complete with stonewalls, a picturesque stream, and serene lake access. The expansive lot offers abundant opportunities, with plenty of room to build a second dwelling, creating the perfect retreat or family compound. A spacious barn on the property adds additional charm and flexibility, ideal for storage or creative use. Whether you're looking to expand, enjoy the tranquility of waterfront living, or simply relish in the peace and quiet of the countryside, this property offers it all. Located just minutes from the heart of Red Hook and Bard College, this property combines rural serenity with convenient access to nearby amenities. Embrace the possibilities and make this idyllic Spring Lake escape your own.

Design and build your dream home with Welcome. This property pairs best with the Modern Cabin 3 home model, but it pairs with several other Welcome models as well. Customize your new home-fully online-with guaranteed pricing. Timing is estimated at 12 - 18 months from construction start to move-in. Buildability and pricing have been confirmed by Welcome, with a promise of no overages or surprise costs during construction. The Modern Cabin 3 by Welcome is a luxurious spin on the traditional cabin. It features 3 bedrooms and 2 full bathrooms, as well as an array of luxury amenities to meet the needs of even the most discerning owner. The open-concept kitchen and living area provide easy access to the rear deck, offering an ideal space for entertaining or unwinding. Upstairs, the loft space adds a touch of versatility and provides ample room for creative expression and personal design. Once you've made your design selections and have an accepted offer on both the construction costs and the land, Welcome handles everything else, from permitting through construction and everything in between. (See MLS #243314 for land-only information.)

Almost paradise!..lure of the good life in Taylor Brook Hollow. A most coveted location with parklike grounds, statuesque hardwoods, a wildflower meadow & a crystal clear brook nourishing an abundance of watercress is a nature lovers setting for this countryside cape. The home has been well maintained, has 4 bedrooms, 2 full baths, (one recently renovated) large formal living room with a fireplace, eat in kitchen, formal dining room and family room with sliders to the rear deck. Full dry basement a plus, lots of sunlight and a lantern lit driveway. Covered Bridge is a private road with only 9 residences. Situated in the beautiful Litchfield Hills you'll be in close proximity to the Berkshires MA & Hudson Valley NY and all that is offered in fine dining with farm to table fare, theatre, hike the AT, cycle or walk the rail trail, ski the slopes, play in our many lakes and rivers. Medical facilities, public & private schools, shopping are all nearby. 1-2 hrs to Bradley Int and NYC airports respectively.

Welcome to Post Hill, a captivating retreat in the heart of the Hudson Valley where history and modern luxury dovetail seamlessly. This 11-acre estate, just 15 minutes from Hudson and two hours from Manhattan, offers a rare chance to own a piece of architectural heritage lovingly maintained by three dedicated owners. The story of this exceptional property began in the 1980s when an 1880s barn was discovered in Pennsylvania. Recognizing the beauty and craftsmanship of the structure, its original stewards meticulously disassembled, transported, and reassembled the barn upon a bucolic parcel in southern Columbia County, NY. It was then expanded with additional bedrooms and modern amenities, and enhanced with reclaimed architectural elements dating back to the 1700s, including windows and wooden paneling from a 1780s English manor, two Adam-style fireplaces, and antique Delft tiles from 1760. Over 5000 reclaimed bricks from a 19th-century factory in Hudson pave the first floor, providing a cool environment in summer and warmth in winter. The current owners equipped the home with smart home technology and installed solar panels that dramatically reduce heating and cooling costs. The central living room boasts 40-foot high ceilings, a wood-burning fireplace, and a second-story library. The primary suite features a vaulted ceiling with hand-hewn beams, a seating area, and an en-suite bath with a bespoke copper soaking tub and walk-in shower. The downstairs bedroom showcases 18th-century English manor details, while a silo has been transformed into an elegant entrance with a spiral stair leading to a second-floor office and ensuite bedroom. The well-appointed brick kitchen, equipped with Bosch appliances, adjoins the spacious dining and living areas, making it ideal for entertaining. Manicured gardens with specimen plantings surround the home, providing a tranquil setting for outdoor activities. Spend chilly evenings around the fire pit, enjoy cocktails on the stone patio, or serve a summer meal in the outdoor screened-in dining room. Explore the grounds, including remnants of an 18th-century post house, or relax by the serene pond⁠ that hugs the forest's edge⁠. Post Hill is a testament to the dedication of its owners, each contributing to its rich history. Experience the perfect blend of past and present in this remarkable property, where every detail tells a story. Begin your own chapter at Post Hill.

Welcome to this captivating Taghkanic home, thoughtfully constructed in 2022 with meticulous attention to detail. This residence is designed for comfortable, contemporary living. The expansive and light-filled ground floor seamlessly connects the living, dining, family rooms, and kitchen, creating an open and airy ambiance. At the heart of the home is the Chef's kitchen, featuring a spacious island perfect for engaging with the cook during meal prep. The kitchen boasts a stunning glass tile backsplash, state-of-the-art appliances, and abundant storage, making it as functional as it is beautiful. The adjoining dining area is generous enough for holiday meals and Sunday breakfasts, with glass sliders opening to a large deck that offers a deep view of the surrounding acres. The family room, located opposite the kitchen, features a modern electric fireplace and is an ideal space for movie nights or watching playoff games. A hallway leads to the laundry room and back door, providing ample space for coats and boots. The ground floor primary suite includes a walk-in closet and a luxurious bathroom with a large vanity, soaking tub, and an oversized, glass-tiled step-in shower. Two additional bedrooms, each with closets and room for desks and computer setups, along with another full bath, complete the ground floor. Upstairs, two spacious rooms span the length of the house. These versatile spaces are perfect for a family room, gym, or large guest area. One room is currently dedicated to crafting and art projects but could easily be converted into an office or studio space. The dry basement features polished concrete floors and French doors that open to the outdoors, providing excellent storage for lawn furniture, tools, and outdoor sports equipment. Additional storage is available in the detached metal garage building. Situated on a mostly open 5-acre parcel with a wooded perimeter, this home offers a harmonious blend of style and practicality, ensuring it meets all your needs for modern living.

Welcome to 114 Sharon Valley Road, a charmingly renovated ranch set on a serene, park-like lot with mature trees and a spacious backyard that gently slopes down to a creek. This home has been thoughtfully updated in a modern farmhouse/colonial style, featuring fresh exterior paint, brand-new flooring in the master suite, a remodeled bathroom, custom blinds, and new lighting fixtures, and a whole-house water filtration system. Located just 10 minutes from Wassaic Train Station, offering a direct line to NYC, this property provides both tranquility and convenience. Inside, the home boasts stunning hardwood floors throughout, with bright, airy dining and living rooms that include a stylish dry bar perfect for entertaining. A versatile bonus room off the living room can be used as an office or den. The spacious primary suite features sliding doors leading to the back deck. Additional highlights include a cozy wood-burning fireplace, an eat-in kitchen and a charming electrified barn with a loft ideal for storage or creative use. The property also features an oversized septic system for added convenience and efficiency. Perfectly situated in the heart of the Litchfield Hills, just minutes from the village of Sharon Center and neighboring villages like Lakeville, Salisbury, Millerton, and West Cornwall. Whether you're looking for a full-time residence or a weekend getaway, this property offers the ideal balance of peaceful living and easy access to local amenities.

A bucolic country road leads you to 69 Yellow City. The approach up a long, winding driveway is lined with maple and pine trees. A dark facade opens to light filled interiors, sunlight dances through the house. Spanning three floors, a careful and considered design-focused renovation was completed in 2024 with minimalism, luxury, and comfortable living in mind. The kitchen has been transformed with limestone floors, beautiful green custom cabinetry, floating shelving and marble countertops. A central island grounds the space alongside a wood burning fireplace, and you’ll find a built in loveseat in the breakfast nook. The attached sunroom makes for an excellent dining room or gathering place, or a quiet spot to read a book while taking in the peaceful views of the surrounding woods and countryside. The sunken living room features wide board wood floors and a massive fieldstone fireplace, a perfect place to settle in. Upstairs there are three bedrooms, the master is ensuite with a wood burning fireplace while two guest rooms share a beautiful bath off of the hall. All of the bathrooms have been fitted with swoon-worthy Italian fixtures and stone basins. On the lower level you’ll find polished concrete floors, an additional bedroom and bathroom, and a living room/gym and kitchenette. Sliding glass doors line the back wall and lead out to a heated, saltwater pool. Walkable to the house is Troutbeck— an incredible c1920 hotel with sprawling grounds and a fabulous bar/restaurant, locals can become members with access to tennis, the spa, and the pool. Under 10m east lies the rolling hills of Litchfield County, CT where you’ll find destination shops and restaurants in Sharon and Salisbury, and just 10m from the house is the Wassaic train station which takes you & your guests into the city in under 2h. An incredible opportunity for weekend or full time use.

Towards the end of Sky Top Road and tucked away at the end of a long driveway sits The Nine-Square House. A modernist masterpiece, the home is perched amidst dramatic natural topography with magnificent views of the Taconic Hills. The Nine-Square House was born of a several-year-long collaboration between a multi-disciplinary artist/designer and an esteemed architect. The result is an immensely livable and sustainable 3,900 square-foot home that carefully balances the relationship between its well thought out interiors and the surrounding wooded landscapes and impressive open views of multiple mountain ranges. Every feature of the home was conceived to be both functional and pleasing to the eye; after all, the team behind the house spent more than two years planning a design that addressed every conceivable ergonomic and environmental question. The nine-square philosophy of living is very much felt in the distribution of spaces - on the main floor, the double living room, dining area, and kitchen all flow into each other and are anchored by a marble fireplace and three large glass doors opening to the exterior terrace with a breathtaking view. The kitchen features Danish-designed Reform cabinetry, Bardiglio marble, and Fisher Paykel appliances. An office, a washroom, a dry bar, and a generously proportioned laundry room complete the main level. The central architectural piece of the home is the solid white oak staircase leading up to the second floor. The four bedrooms upstairs, though spacious, are much more private and intimate, each with large windows on two sides, communing with the serene and quiet landscape outside. The two sizable bathrooms have dedicated shower rooms and freestanding soaking tubs with panoramic views. The expansive landing of this level has a reading room at one end and a sitting area at the other. Distinguishing features of the Nine-Square House include high energy efficiency due to insulation exceeding all current standards, multi-zone central AC, radiant heated floors, solid 200 lb interior doors, satin nickel Kohler fixtures, cast iron sinks, and solid forged and machined brass and satin nickel door hardware. An expansive floor plan and extensive technical solutions are met with human-scale rooms, creating an abundantly peaceful and welcoming environment. The land around the house, perfect as it is, has been touched as little as possible. There are wooded and open areas, with meandering walking paths trailing through the property. The minimal clearing around the house has been planted with native plants, allowing ferns and forest growth to come back up to the building over time. The Nine-Square House is just 20 minutes from Hudson, Great Barrington, and Millerton and two hours from New York City.

HYDRANGEA COTTAGE - Perfectly picturesque c1740 English-style colonial in the heart of Sharon. This lovely 2-3 bedroom, 3.5 bath home has been meticulously renovated and adorned with Farrow & Ball paint, creating comfortable living spaces with modern luxuries. Of note, this in-town gem features a charming eat-in kitchen with high-end appliances and gorgeous soapstone sink. Dining room with fireplace provides access to large deck, ideally positioned to capture stunning mountain views and sunsets. Large living room and study with period details and beautiful wood floors. Upstairs: Primary Bedroom en-suite with glass shower and porcelain console sink. Second Bedroom and full bath with clawfoot tub. Downstairs: fabulous extra room on lower level with outside access. Great as a study/exercise room or as additional bedroom. Also on lower level ~ full bath with clawfoot tub and washer/dryer. Flower gardens surround this sweet and very chic country cottage. Close to area private schools (Hotchkiss, Kent, Salisbury School and Indian Mountain School). Walk to the Historic Sharon Green, Hotchkiss Library, Sharon Playhouse or Historical Society. 2 hours to NYC. Absolutely enchanting!

Welcome to Hilltop Road. This stunning property offers the perfect blend of country living and urban convenience, nestled on 4 picturesque acres with a pool. With seven spacious bedrooms and 4.5 luxurious baths, there's plenty of room for family and guests alike. Step into the heart of the home-a breathtaking kitchen that's a culinary dream, featuring a grand center island and a captivating window that frames your idyllic surroundings. Enjoy cozy evenings in the family room with a fire or unwind on the charming screened-in porch with a beautiful view, designed for relaxation and entertainment. Ideal for entertaining and social events, this home features an expansive master suite along with four additional bedrooms located on the second floor. Ascend to the third floor, where you'll find two more spacious bedrooms and a versatile and bright playroom or gym. This layout ensures that everyone can enjoy their own space while providing ample room for memorable gatherings. Step outside to discover beautifully landscaped grounds, complete with a heated pool, fenced-in garden and a large bluestone terrace ideal for grilling and gatherings. Designed for entertaining and luxurious living, this home is not just a place to live-it's a lifestyle. Come and experience Hilltop Road for yourself.

A simple ranch in a spectacular location...an opportunity to create your dream house in a secluded parcel in the Town of Sharon. The land was part of an older farm, so surrounded by meadows filled with wildflowers and wildlife. Long, views to the east over wind blown fields with mowed trails to walk. Beautiful sunrises and big skies to enjoy. The driveway is a quarter mile long with underground utilities for unspoiled landscapes.

Capture the history and grandeur of Great Elm, the unparalleled 19th century Georgian colonial estate that was once the childhood home of author and influential political commentator, William F. Buckley Jr. Nestled in the heart of Sharon, CT, this prestigious property is a rare opportunity to acquire a residence steeped in historical significance and architectural elegance. Great Elm boasts 8,072 sqft of luxurious living space, crafted with impeccable design choices throughout. From the art deco bathrooms to the William Morris wallpaper, every room exudes sophistication and meticulous care. William Buckley Sr. purchased the original 1812 house in 1923, expanding it over time to accommodate his growing family. The main level primary bedroom suite and gracious sitting rooms, each with gorgeous detail and wood burning fireplaces, open to the dramatic three-story Atrium, a year-round haven reminiscent of New Orleans. Upstairs are 7 beautifully appointed ensuite bedrooms, one of which is used as a gym; another as an office. This property is the anchor of a community of homes joined by an Association that manages the 50 magnificent, park-like acres and amenities, including a heated, Gunite pool, pool house, tennis and paddle/pickle courts. This spectacular property in the beautiful Litchfield Hills is more than just a residence; it's a chance to own a piece of U.S. history. Close to Hotchkiss, Salisbury, Indian Mountain and Millbrook Schools. Only 2 hours to New York City.