The agencies at Hillsdale
These agencies offer a selection of luxury properties vente at Hillsdale. Feel free to contact them for personalized assistance.
Welcome to DREAMLAND. Set along a quiet country road, this exceptional 22 acre parcel offers the rare combination of privacy, curated natural beauty, and effortless access from New York City. Just minutes from the Taconic State Parkway, the property is ideally positioned for seamless weekend escapes or full-time living. A sun-drenched open meadow—perfectly oriented for southern exposure—creates an ideal setting for a modern country estate, while a network of winding, tree-lined trails invites exploration through a landscape of mature hardwoods, including striking 200-year-old oak trees and historic stone walls. The setting feels both expansive and intimate, a 5 acre building site offering the opportunity to design a home that fully captures the surrounding natural beauty. Located moments from the renowned Hawthorne Valley School and its celebrated farm store, and within easy reach of the cultural richness of the Berkshires, this property places you at the intersection of nature, design, and lifestyle. Skiing, art, and dining are all nearby, while the vibrant riverfront city of Hudson is just 20 minutes away. A rare opportunity to create a legacy property in one of the Hudson Valley’s most sought-after settings—where architecture, landscape, and lifestyle come together seamlessly. BOHA, Driveway permit, survey
…By Four Seasons Sotheby's International Realty
Perched atop a breathtaking ridgeline with some of the most extraordinary panoramic views in the Berkshires, this remarkable almost 18-acre estate parcel is one of only seven exclusive homesites within this private enclave. With the most recent neighboring estate having changed hands for $5.6 million, the property's exceptional pedigree and enduring value are unmistakable. Surrounded by more than 220 acres of permanently protected conservation land, the property offers unparalleled privacy, timeless natural beauty, and direct access to a protected greensward ideal for hiking, cross-country skiing, and year-round outdoor enjoyment. A handcrafted stone bridge spanning a tranquil woodland stream welcomes you to an expansive, level building site with coveted southeastern exposure, perfectly positioned to capture dramatic sunrises, rolling hills, forested vistas, and ever-changing Berkshire skies. The entrance, approach, dwelling site, and selective clearing have all been thoughtfully completed, providing an exceptional canvas for a world-class estate. The property spans two of the Berkshires' most desirable low-tax towns--11.2 acres in Egremont and 6.8 acres in Alford and borders New York State, offering the perfect blend of Berkshire culture, Hudson Valley charm, and convenient access to major metropolitan destinations. Perfectly situated in the heart of the Berkshires--home to Tanglewood, Jacob's Pillow, exceptional farm-to-table dining, boutique shopping, renowned cultural institutions, and endless outdoor recreation--the location balances complete privacy with remarkable accessibility. Hudson, New York, with direct Amtrak service to New York City, is nearby, while Manhattan's Upper West Side is approximately two hours away. Boston is just 2½ hours, Albany one hour, and Hartford 1½ hours. With an existing well, roughed-in driveway, excellent percolation, and permanently protected unobstructed views, much of the essential groundwork has already been completed. Opportunities of this caliber are exceedingly rare--a chance to create a legacy estate in one of the Berkshires' most coveted and thoughtfully planned settings.
…By William Pitt Sotheby's International Realty
Big views in Clermont from this 7.63 acre parcel. Drive a private drive through a former train trestle, creating a dramatic entrance to this primo buildable lot. BOHA approved for in ground septic and a survey is available. The home site commands complete privacy with the Catskill Escarpment visible from a western facing design. Currently, a healthy meadow of native flowers with good tree lines surrounding the property and an elevation that is completely inviting. Situated between Red Hook and Germantown NY, this spot enjoys the Columbia County rural nature while being completely convenient to all that these Upstate hotspots have to offer from lunch at Ottos in Germatown or dinner at Bridgitte in Red Hook. Fifteen minutes from both Hudson and Rhinebeck and a short drive to both Amtrak stations. Build your Upstate farm to table dream house.
…By Four Seasons Sotheby's International Realty
Rarely does a property of this caliber become available. Spanning approximately 234 acres across two contiguous parcels (162 acres and 71.5 acres), this exceptional offering features productive hay and corn fields, rolling farmland, mature woodlands, and breathtaking long-range views of the Taconic Mountains and Catskills. Multiple elevated building sites provide the opportunity to create a private estate, compound, or working farm with spectacular panoramic views. Lovingly stewarded by the same family for generations, the land has been actively farmed and maintained, offering fertile soils and endless possibilities for agriculture, equestrian pursuits, recreation, or development. Private, scenic, and remarkably versatile, this is a rare opportunity to own a significant piece of Hudson Valley countryside.
…By William Pitt Sotheby's International Realty
Lake Mansfield Lakefront Lot. Rare chance to live on a private road, on the prettiest of Lakes, minutes to downtown Great Barrington. Over 3 Acres with 175 feet of frontage in the most bucolic of settings. Make your dreams come true.
…By William Pitt Sotheby's International Realty
471 Church Avenue , Lot 1 , Germantown, NY , 7.95 Acres The best of the Hudson Valley is within easy reach from this picturesque 7.95-acre parcel in Germantown. Set along a quiet country road and offering Board of Health approval, Lot One presents an exceptional opportunity to build a country home in one of Columbia County's most desirable locations. Here, peaceful rural living comes with remarkable convenience. Hudson, with its celebrated restaurants, galleries, shops and Amtrak service to New York City, is approximately 15 minutes away, while Rhinebeck Village is just 20 minutes in the opposite direction. Tivoli and Germantown's charming hamlet are also close at hand. A beautiful setting, generous acreage and an enviable location between two of the Hudson Valley's most sought-after destinations. A rare opportunity to create something entirely your own.
…By Four Seasons Sotheby's International Realty
471 Church Avenue, Lot 2 , Germantown, NY , 8 Acres Part of a rare offering of three distinctive parcels along a peaceful country road in Germantown, Lot 2 encompasses eight acres of beautiful Hudson Valley landscape and offers an inviting opportunity to build something entirely your own. With Board of Health approval already in place, the property provides a wonderful starting point for a thoughtfully designed country home--private enough to feel like a true retreat, yet remarkably convenient to the best of the region. Perfectly positioned between Hudson and Rhinebeck, both approximately 15-20 minutes away, the property offers easy access to restaurants, galleries, shops, farmers markets and Amtrak service while retaining the quiet, rural character that makes this corner of Columbia County so special. Whether considered individually or alongside the neighboring parcels, Lot 2 presents a rare opportunity to put down roots in one of the Hudson Valley's most sought-after settings
…By Four Seasons Sotheby's International Realty
471 Church Avenue, Lot 3 , Germantown, NY , 11.8 Acres The largest of three beautiful parcels at 471 Church Avenue, Lot 3 offers 11.8 acres in the heart of sought-after Germantown. Striking rock outcroppings, old stone walls and a charming water feature give the land a wonderful sense of character and place. Private and peaceful, the property offers an exceptional canvas for creating a country home thoughtfully connected to its natural surroundings. Mature landscape and generous acreage provide a sense of seclusion while remaining close to the vibrant communities, culture and beauty that define this special corner of the Hudson Valley. A rare opportunity to own a substantial piece of land in Germantown and create something entirely your own.
…By Four Seasons Sotheby's International Realty
Located on a splendid unpaved country road with tidy stone walls and tall trees in the heart of Milan NY, this particular 96 acre land offering comes with knockout views of the Catskill escarpment and a primo homesite located high on the parcel. Easy and enjoyable to walk to the crest due to a handy trail cut into the wild. The landscape features a quarter acre pond, undulating, forested hills, rock outcroppings, tangles of wild roses and native wildflowers, scenic meadows and vistas to the West while enveloped in it’s rural character and charm just begging for a visit from your talented architect. Rowe Road is conveniently located in the least populated town in all of Duchess County and at the heart of Milan under 2 hours from the city via the nearby Taconic State Parkway.
…By Four Seasons Sotheby's International Realty
Beautiful level lot with woods and meadow. Mountain views. Minutes to downtown Great Barrington and Butternut Ski Basin. Perced. Build your dream retreat in the Berkshires!
…By William Pitt Sotheby's International Realty
Drive through Sharon's scenic pastoral landscape, past the serene waters of Indian Lake, and arrive at a rare 8 acre sanctuary that hasn't been on the open market in over 30 years. This gently sloping lot is the elusive combination you've been searching for: absolute privacy and unbeatable convenience. Anchored by the tranquil banks of Indian Lake Creek, the land naturally curves along the Millerton Road side, making it incredibly easy to envision your dream home tucked perfectly into the hillside. Directly across the street lies 81 acres of cherished, protected Sharon Land Trust, offering immediate access to hiking and untouched nature right outside your door. The property currently features a run-in shed and is perfectly suited to remain a haven for farm animals. Located just moments from the vibrant centers of Millerton, Lakeville, and the Sharon town green. Bring your architect and your vision. This is a truly rare find. Parcel is on the corner of Dakin Road/Millerton Road.
…By William Pitt Sotheby's International Realty
Nestled on a private road amid Salisbury's picturesque landscape, this 9.18-acre parcel presents a rare opportunity to craft your own secluded retreat. Enveloped by nature and bordered by open space, the land features rolling topography that offers both privacy and breathtaking views. Underground utilities are already in place, providing a seamless path from dream to development. Picture your custom home perched to take advantage of the serene surroundings-a place to unwind, reflect, and reconnect with nature. Ideally located near some of the Northeast's most prestigious schools, including The Hotchkiss School, Indian Mountain School, and Salisbury School, the property offers both a peaceful lifestyle and educational excellence. Outdoor enthusiasts will find themselves minutes from the Appalachian Trail and the Housatonic River, a destination prized by fly-fishing aficionados. Despite its tranquil setting, the property is conveniently located just two hours from New York City and only 25 minutes from the Metro-North station in Wassaic, NY. Your private escape awaits in the heart of Litchfield County.
…By William Pitt Sotheby's International Realty
Properties of this magnitude and character are becoming a true rarity in today's market. Brookmede Farm, isn't just a listing; it is a magnificent blank canvas of 22 beautiful scenic acres, defined by sweeping mountain views and a profound sense of quiet serenity. From the moment you arrive, the silence and the scale of the landscape invite you to imagine the unlimited possibilities. Whether you envision a world-class equestrian estate, a sustainable organic farm with cows and chickens, or a sophisticated multi-structure family compound, this land provides the space and the soul to make it a reality. Standing as a centerpiece to this vision is a towering, three-story Timber Frame barn. With its incredible volume and structural presence, it offers a legendary head start for a premier stable, a grand creative studio, or an architectural centerpiece for your new estate. The property is directly abutted by conservation land, ensuring your privacy and pristine views are preserved forever. The location is nothing short of ideal. You are nestled in a peaceful pocket of New Marlborough where complete privacy is guaranteed, yet you remain within touching distance of the Berkshires' most beloved landmarks. You are just two minutes from the world-class culinary experiences at Cantina 229 and The Old Inn on the Green, Gedney Farm and Southfield Store, and only ten minutes from the vibrant shops and culture of Great Barrington. This is the ultimate opportunity for a visionary buyer who wants a quiet, scenic retreat without sacrificing proximity to the best the region has to offer. You truly have to explore these 22 acres in person to feel the energy of the land and see the potential of the barn. Come stand on this ground, take in the mountain vistas, and see how you can transform this rare Berkshire find into your own dream property.
…By William Pitt Sotheby's International Realty
Build your dream home on this 9.33-acre parcel in the highly sought-after town of Salisbury, CT. Set on a scenic country road in the picturesque Northwest Hills, the site features completed engineering for a 3-bedroom residence, with the potential for a larger home. This property offers a quintessential New England lifestyle just minutes from prestigious private schools and bucolic villages. Enjoy the perfect balance of rural tranquility and premier access to the area's rich cultural heritage, lakes, outdoor recreation and world-class motorsport events at the historic Lime Rock Park. A perfect, blank canvas awaits your architectural vision.
…By William Pitt Sotheby's International Realty
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These agencies offer a selection of luxury properties vente at Hillsdale. Feel free to contact them for personalized assistance.