Courtesy: Four Seasons Sotheby's Int.
518-822-0800
For the first time on the market in 50 years, Underwood Farm, with its late 18th century cedar shake 3200 square foot salt box house, is 281 acres of primo hilltop exposure. Driving the property, the entire expanse is the high ground between West End Road and Rockledge Road with its equal parts woods, open meadows and fields with the rolling Taconics to the East. Below, the neighborhood is experiencing a renaissance and is dotted with new restorations of gorgeous farmhouses and new builds, adding a fresh dynamic to the area. This site is perfect for any health and wellness guru looking to recreate life on a farm for the benefit of the community, for an hotelier or hospitality group to develop an Upstate experience compound or simply to restore a piece of American architectural history to become a beautiful 4 bedroom 2 bathroom residence in the heart of the Craryville to Hillsdale corridor and all the conveniences that entails. The house sits high on a bluff overlooking West End Road and below the dale is a large former dairy barn with a metal roof and cattle stalls. There is a detached garage with an efficiency apartment over it behind the house with the opportunity to plant a crop in an adjacent waiting field. Three large parcels make up this offering and the residence has the opportunity to sell the remaining two while maintaining 100+ acres for an impressive estate.
Courtesy: Barns & Farms Realty, LLC
518-822-0226
Hillsdale 2500 SF 4BR3BA Residence with large deck, inground pool and 60 x 1003Garage on 2.9 acres. Currently Auto Repair Buiness near Junction of Routes 22 & 23 incredible opportunity to continue auto repair and towing business or convert 60 x 100 Garage into storage facility or other use.
Courtesy: The Meenagh Group Realty
518-281-5496
1800s farm house. Just waiting for some TLC. This property consists of the main farm house. one very large barn. Addtional 3 out building. One of the back building contains an attractive apartment.The property butts up to the Harlem Valley Rail Trail. Walking distant to the Hamlet of Hillsdale. Including the Roe Jan Brewing Co. IGA, The Hillsdale House, The town park. Less then 5 min ride to Catamount. 25 min ride to Hudson NY. 20 min ride to Great Barrington MA.Property is being sold as is.
Courtesy: Copake Lake Realty Corp.
518-325-9741
Classic Country Home with Pond, Pool & Barns Located just minutes from Catamount Ski Area, Hudson, NY, and Great Barrington, MA. Steeped in history and charm, this distinctive residence—believed to date back to the late 1800s—offers timeless character with thoughtful updates and plenty of space to enjoy country living. This 4 BR, 2.5 BA, 2,225± sq. ft. home is sited on 12+ acres. The rocking chair porch welcomes you. Featured are original hardwood and parquet flooring with a traditional layout. The main level offers an eat-in kitchen, formal dining room, office, and great room. The great room includes a fireplace, large picture window overlooking the pond, wet bar, built-in cabinetry, and a half bath—a warm and inviting gathering space. Upstairs, the primary suite offers a private bath, accompanied by three additional bedrooms and a hallway full bath, providing comfortable accommodations for family or guests. Outdoor living is equally impressive. A 16' x 32' in-ground pool is perfect for summer enjoyment. The picturesque pond, about ⅓ acre in size, is fed by a nearby stream, adding a tranquil view from the home and yard. There are walking trails throughout the property, ideal for exploring the natural beauty of the surroundings. Outbuildings include a large red barn with hand-hewn beams, as well as a red barn/shed behind the house that is used as a woodshed. The remains of what was likely a foundation for an old corn crib and a horse barn in need of total rehabilitation remain as echoes of the property's rich agricultural past. From antiquing, hiking, skiing, zip line, music, theater, farm-to-table restaurants, bicycling, and more—there's something for everyone! All this approximately 2 hours from NYC and 2.5 hours from Boston. A truly central meeting place for family and friends. With its scenic setting, historic details, and modern mechanicals, this property offers an ideal blend of vintage charm and rural functionality—ready for its next chapter.
Courtesy: William Pitt Sothebys Intn'l
518-392-0244
This completely redone Hillsdale cottage is the perfect rustic but refined getaway! Only 525 square feet, with one studio style bedroom, it feels spacious with a vaulted beamed ceiling, new wideboard pine floors, a stunning new kitchen with all new appliances including a five burner gas stove with a stainless steel hood, Fisher Paykel dishwasher drawers, double sinks, butcher block counters and a convenient breakfast bar. The new bathroom has a large tiled shower and a country style sink. A new energy efficient mini-split provides heat and air conditioning. In excellent condition with freshly painted wood siding and front deck, a walk out basement for storage, a new well and a firepit for chilly evenings. On almost an acre of land on a country road but just 5 minutes to Hillsdale for groceries, Farmers Market, restaurants, shops, library, wine store and new bookstore. 10 minutes to Catamount for skiing or to Copake Lake for golf or boating. 20 minutes to the Berkshires for theatre and music or to Hudson for shops, galleries, top notch restaurants and Amtrak. Only 2 hours to NYC. Seller financing possible. House can be purchased furnished, completely turn key, and ready for you!
Courtesy: Four Seasons Sotheby's Int.
518-822-0800
Said to be Hillsdale's second oldest home, this historic c1788 Shaker built center chimney Colonial sits on 17 acres of sprawling green hillside, gardens, and fruit trees. Once the home of Captain John Collin III, the home sits along the beautiful corridor connecting the Hudson Valley and the Berkshires— an area characterized by its rolling hillsides and rural landscape. Meticulously restored, you'll find fabulous period details such as original 12-over-12 wavy glass windows with custom storms, beautiful curved walls, hand hewn beams and old growth pine floors. Enormous slabs of marble make up the front steps & foundation walls. You'll find wonderfully high ceilings for a house of this age, and a four season sunroom with radiant heated floors & AC. Despite its formal proportions the house lives comfortably, the kitchen opens to a lovely seating area with a wood burning fireplace, undoubtedly the room you'll spend most of your time in. There are two additional, large sitting/dining areas on the first floor, a mudroom & powder room. Upstairs, you'll find five bedrooms, some large & lightfilled and others charming & petite, and two full baths including an ensuite in the primary. Outside, the 17 acres are comprised of woods and meadow, there is a fenced in garden with ten raised beds & a garden shed, heirloom varieties of apples, peaches and pears. A trail meanders through the woods. There is a full house generator. An early home with pedigree, you are just 15m to Great Barrington, 20m to Hudson, and under 2.5h from NYC.
Courtesy: Four Seasons Sothebys Intl
518-822-0800
Said to be Hillsdale's second oldest home, this historic c1788 Shaker built center chimney Colonial sits on 17 acres of sprawling green hillside, gardens, and fruit trees. Once the home of Captain John Collin III, the home sits along the beautiful corridor connecting the Hudson Valley and the Berkshires— an area characterized by its rolling hillsides and rural landscape. Meticulously restored, you’ll find fabulous period details such as original 12-over-12 wavy glass windows with custom storms, beautiful curved walls, hand hewn beams and old growth pine floors. Enormous slabs or marble make up the front steps & foundation walls. You’ll find wonderfully high ceilings for a house of this age, and a four season sunroom with radiant heated floors & AC. Despite its formal proportions the house lives comfortably, the kitchen opens to a lovely seating area with a wood burning fireplace, undoubtedly the room you’ll spend most of your time in. There are two additional, large sitting/dining areas on the first floor, a mudroom & powder room. Upstairs, you’ll find five bedrooms, some large & lightfilled and others charming & petite, and two full baths including an ensuite in the primary. Outside, the 17 acres are comprised of woods and meadow, there is a fenced in garden with ten raised beds & a garden shed, heirloom varieties of apples, peaches and pears. A trail meanders through the woods. There is a full house generator. An early home with pedigree, you are just 15m to Great Barrington, 20m to Hudson, and under 2.5h from NYC.
Courtesy: Copake Lake Realty Corp.
518-325-9741
Reduced Price! Close to skiing and the Berkshires. Once the Flood farmhouse, circa 1850. Over 3400 sf sited on 5 acres. Beautiful perennial gardens. Farmland views of the Taconic Range. Attached 2-car garage. The main floor has an office, that connects the home to the garage. Formal living room and formal dining room. The primary suite includes both his and hers full bathrooms, and a changing room. On the second floor is an apartment with its own access to the outdoors. Seller wishes to reside as a paying tenant. and is on a wait list. Departure date is negotiable. This farmhouse has been loved throughout the years. The price reflects the need for some upgrades. Located just off Route 22. Yonderview Road also goes to Route 23 and close to Catamount Ski Area and Adventure Park. The Berkshires are moments away. Convenient to so many cultural venues such as Tanglewood, Jacobs Pillow, even Woodstock (just a little over an hour away). Take a bicycle ride on the Harlem Valley Rail Trail or experience the farm-to-table restaurants. There is so much to do. Columbia County is ~ two hours from New York City and ~2.5 hours from Boston. Amtrak is ~ 1/2 hour away in Hudson (shopping, antiquing). MetroNorth is in Wassaic, ~35 minutes south on Route 22.
Courtesy: Gabel Real Estate
518-392-4975
Ridge Lane in Hillsdale is the perfect country retreat. Set on 7+ acres on a quiet dead end road. This newly built farmhouse captures the charm and solitude that make Hillsdale so desired. Come in to the mudroom, kick off your shoes and enjoy the space of a real country kitchen. The open living space flows easily to the dining area and living room or out to the deck to enjoy the blue sky. An office and bath round out the first floor. Upstairs there are two more bedrooms that share a full bath and the main suite is bathed in sunlight. A heated barn just off the house provides play space, work space and room for a car or two.
Courtesy: Columbia County RE Specialist
518-325-9784
If your checklist for a new home includes any of the following, your search may have reached a successful conclusion. Let us introduce you to 110 Meadow Lane in Hillsdale NY. Views - Totally unique forever views that will inspire for a lifetime Location - Near the NY and MA border offering easy access to both Columbia County and the Berkshires Single-Story Living - A popular option these days for many reasons Seclusion - The last lot at the cul-de sac end providing peace, quiet and hard to find tranquility Quality Materials - Hardie Plank siding, quartz countertops, white oak flooring, a new roof, new windows and doors, composite decking and exterior trims, radiant heated floors in both bathrooms, whole house backup generator, paved driveway, . . . Craftsmanship - Evident in every detail throughout the home Low-Maintenance - This ''like new'' home will provide years of low maintenance - high enjoyment home ownership Three bedrooms and two full baths provide plenty of space for family and guests. The large living room features a vaulted ceiling, propane fireplace, French doors to the deck and breathtaking views. The adjacent great room provides additional space when needed, while also serving as a tranquil room to relax or catch up on your reading in front of a fire. The exquisite kitchen would be the envy of any home with quartz counters, stainless appliances, luxury cabinets and plenty of storage. There is an oversized laundry room with additional storage, and the attached two-car garage provides all-weather protection and convenience. We don't believe that you will find a more complete, or desirable package at this price point. Come see what makes this home such a special opportunity and decide for yourself whether or not it completes your checklist!
Courtesy: Compass, Hillsdale
914-327-2777
Tucked away at Copake Lake! This fully renovated home is set on a private 5-acre lot and features an open floor plan with a spacious eat-in kitchen and large island, a dining area that seats 10, and a living room with a grand fireplace and custom built-in benches. French doors open to a large screened-in porch on a wrap-around deck, offering sweeping views of the surrounding landscape. A second, more secluded deck sits below, nestled among the trees—perfect for quiet moments. The main floor includes a primary bedroom with vaulted ceilings and deck access, and an en-suite bathroom with shower. Two additional bedrooms share a full bathroom. The lower level has a media/playroom plus two more bedrooms with windows and closets, along with a full bathroom featuring a large bathtub. There is also a unfinished storage area with outdoor access on this level. Outside, a large pool on the south side of the property with great sun adds to the perfect weekend or full-time home. The home enjoys a private gated lake-front expanse with beach and dock shared by the association. Experience the best of outdoor charm and adventure Copake Lake and the surrounding Hudson Valley towns offer. Located near the renowned Catamount Ski Area and adventure park, the area offers year-round appeal—from summer hikes at Bash Bish Falls and boating on Copake Lake to skiing and snowboarding in winter. Golf at Copake Country Club, stroll through nearby Historic Hillsdale and enjoy easy access to Hudson NY's art scene and Great Barrington's shops.
Courtesy: Red Apple Realty
518-851-9601
Newly Renovated Hillsdale Gem! Welcome to this beautifully renovated 3-bedroom home in the heart of Hillsdale. Thoughtfully updated with today's buyer in mind, this residence blends modern comfort with timeless charm. Inside, you'll find a bright, welcoming kitchen featuring quartz countertops, high-end vinyl plank flooring, and a suite of updated appliances designed for both style and functionality. A large living room perfect for entertaining, with a potential dining area on one end featuring a built-in china cupboard. There is also a separate family room with a wood stove to keep you cozy on chilly nights, with glass doors that lead you out to the 18' x 18' stone patio that is ideal for summertime relaxation and entertainment. The two bedrooms on the main level are serviced by the updated 3/4 bath, while a large third room upstairs offers endless possibilities for an additional bedroom or office. For your convenience, there are laundry facilities with built in storage and cubbies located in the entry way mudroom. Step outside to your private backyard; a serene retreat perfect for morning coffee, entertaining, or simply unwinding in nature. The outdoor space offers a fenced-in portion of the 1-acre yard, privacy, and tranquility, making it a true extension of the home. Every detail has been carefully considered; from the freshly installed siding to the recent roof, ensuring peace of mind for years to come. This turnkey property is ready for its next chapter - whether you're seeking a weekend escape or full-time residence, this home delivers modern living in a peaceful Hudson Valley setting.
Courtesy: Gilcrest Properties
518-610-8121
New listing in Hillsdale, set high on a quiet dirt road where privacy, peace, and panoramic views define your backdrop. Why wait a year and a half for a new build when you could be in by Christmas? This brand-new construction is underway and ready for you to make it your own. The structure is in place with a brand-new drilled well, septic system, and 200-amp electrical service already set. Plumbing, electric hookups, walls, flooring, fixtures, and finishes are still needed—giving you full creative freedom to choose your style and finish every detail to your taste. The main level offers 1,800 sq ft with 3 bedrooms, 3 bathrooms, and a dedicated home office. With soaring 10' ceilings, oversized rooms, and new Pella windows and doors, the home is flooded with natural light and sweeping easterly views across the marsh and surrounding landscape. Step out onto the massive mahogany deck where Mother Nature puts on a show in all four seasons—whether it's fall foliage, winter snow-glow, spring blossoms, or endless summer skies, the scenery is ever-changing and unforgettable. The walk-out lower level adds another 1,800 sq ft of potential, waiting to be transformed into whatever you can dream up—an expansive recreation room, home theater, wet bar and lounge, gym, or even a golf simulator. The possibilities are truly limitless. Nestled among the trees with total seclusion yet close to everything, this home is ideally located. Just 15 minutes to Hudson for dining, shopping, and the Amtrak station, 2.5 hours to NYC, and surrounded by year-round recreation. Skiing at Butternut, Catamount, and Jiminy Peak are all within 30 minutes. Bash Bish Falls, multiple conservation areas, and endless hiking and biking trails are minutes away. This is more than just a house—it's an opportunity to skip the waiting list and create the Hudson Valley retreat you've always imagined. With the hard work done and the canvas set, the only thing missing is your vision.
Courtesy: Compass, Hillsdale
914-327-2777
Proudly offering one of Hillsdale's most iconic and enduring homes—an exquisite piece of the Hudson Valley's heritage, perfectly positioned at the crossroads between Hudson, NY and Great Barrington, MA. Set in the vibrant and historic hamlet center, this timeless 3-bedroom, 2-bathroom residence is simply beautiful colonial charm. Thoughtfully renovated from top to bottom, the home retains its original 1790's soul with restored wide-plank wood floors, antique glass windows, and two original fireplaces anchoring the front and rear parlors. The front parlor is formal and elegant, while the rear parlor offers flexible living space that is ideal as a first floor fourth bedroom, office, or cozy and quiet media room. The large eat-in kitchen is a standout, featuring Bosch appliances and an inviting breakfast bar. A traditional pantry nods to the home's roots, while Carrara marble bathrooms and central air conditioning provide the ease of modern living. The formal dining room is perfect for entertaining, and the cathedral-ceiled primary bedroom creates a peaceful retreat upstairs. Step outside to discover a surprisingly spacious and private backyard—an oasis in the center of town. Zoned for both residential and commercial use, the property offers rare flexibility: perfect as a full-time residence, a charming boutique, café, or even a destination restaurant in a town brimming with character and foot traffic. Live where everything is at your doorstep—walk to the local grocery, post office, hardware store, wine shop, retail shops, hair salon, diner, brewery, and even a historic tavern. Outdoor enthusiasts will appreciate quick access to the Harlem Valley Rail Trail for biking, walking, and running.
Courtesy: Houlihan Lawrence Inc.
518-822-0300
Historic Upstate NY Sanctuary - 8.7 Magical Acres in Hillsdale, NY - known for its scenic beauty and small-town charm Escape to your own private paradise on this enchanting 8.7-acre property featuring a charming 1820's cottage, pristine swimming pond with waterfall, and endless outdoor adventures. This secluded sanctuary offers the perfect blend of historic character and natural beauty, just minutes from world-class recreation and cultural attractions. The heart of the property centers around a charming historic cottage set well off the road for complete privacy, surrounded by lush landscapes and meandering walking trails. A babbling brook winds through the property, crossed by charming bridges that lead to hidden corners of this magical retreat. The crown jewel is a large spring-fed pond with its own waterfall—perfect for swimming—plus a dedicated pond house for changing and relaxing. Location Excellence: •5 minutes to Catamount Ski Mountain •15 minutes to Great Barrington's shops and dining •30 minutes to Tanglewood and Hudson's cultural scene •Prime Berkshire positioning for year-round recreation This exceptional property offers incredible potential: maintain the historic cottage as your getaway while building your dream home elsewhere on the expansive acreage or create a sophisticated compound with rental income opportunities. The combination of pristine natural features, historic charm, and unbeatable location makes this a rare find. Your private 8.7-acre playground awaits—where adventure meets tranquility just minutes from the Berkshires.
Courtesy: Four Seasons Sothebys Intl
518-822-0800
Step into a world of timeless charm and understated luxury with this impeccably restored 18th-century farmhouse, nestled on over 6 acres of landscaped lawns, flowering gardens, and river frontage along the trout-rich Roe-Jan Kill. The residence exudes warmth and authenticity, offering luminous interiors and inviting outdoor living spaces ideal for entertaining or quiet retreat. The grand living room, anchored by a wood-burning fireplace and lined with a wall of windows, frames views of the grounds and invites natural light throughout the day. The custom-designed kitchen marries modern function with period detail, while the sun-drenched dining room—with exposures on two sides—provides an elegant setting for intimate gatherings. A deep, screened porch spans the length of the north wing, overlooking the gardens and flowing lawns. On the main floor, a serene en suite bedroom and a private guest suite with sitting room and separate entrance offer flexible accommodations. Upstairs, two charming bedrooms share a beautifully appointed bath. A short stroll through lush gardens and across a second private drive leads to the stunning, two-story post-and-beam barn. Currently curated as an antique store, the structure offers an expansive lofted studio and is zoned for commercial or residential use—ideal for a gallery, guesthouse, or creative workspace. This rare, historic compound offers a peaceful, pastoral lifestyle just over two hours from Manhattan—a perfect fusion of old-world charm and modern-day potential. Tucked into the rolling foothills of the Berkshires, Hillsdale is one of the Hudson Valley’s most coveted enclaves—quietly elegant, unspoiled, and deeply rooted in charm. Just over two hours from Manhattan, it offers the ideal blend of refined rural living and easy access to the region’s most sophisticated cultural and culinary experiences. Here, sweeping vistas, winding country roads, and historic farmhouses coexist with curated farm-to-table restaurants, chic design shops, and proximity to world-class destinations like Hudson, Great Barrington, and Tanglewood. Hillsdale is home to Catamount Mountain Resort for year-round recreation, from skiing to ziplining, and just minutes from Copake Lake, private golf clubs, and nature preserves. Discreet, low-key, and deeply authentic, Hillsdale attracts those seeking serenity without sacrifice—an elevated escape that feels worlds away, yet entirely within reach. Hillsdale is fast becoming one of one of Columbia County’s most desirable investment destinations. Just over two hours from Manhattan, this historic town offers a rare combination of timeless charm and smart, long-term value. As boutique hospitality, curated design, and high-end food culture continue to expand nearby—in Hudson, Great Barrington, and Chatham—Hillsdale has quietly emerged as a prime location for luxury second homes and discreet development. With a strong track record of appreciation and zoning that allows for flexibility, it's an ideal market for those looking to balance lifestyle with strategic growth Hillsdale offers proximity to a refined network of private clubs, golf courses, and recreational resorts that define the elevated Hudson Valley lifestyle. You're just minutes from the exclusive Copake Country Club, private lakefront communities, and the slopes of Catamount Mountain, offering four-season access to skiing, hiking, and ziplining. Paired with nearby spas, organic farms, and award-winning restaurants, Hillsdale is a magnet for those who appreciate privacy, taste, and a quietly luxurious pace—without sacrificing access to world-class experiences.
Welcome to Mac Brown Waterhouse, a 119-acre estate in Claverack, NY, offering total privacy, wide southern light, and a large swimmable pond with a pebble beach. The 1830s farmhouse features four bedrooms, two baths, original moldings and Dutch doors, and a bright, open layout designed for indoor-outdoor living. Additional spaces include an upgraded studio barn, oversized potting shed, EV-ready carport, and a dreamy outdoor bath deck. Rewilded fields and meadows unfold around the home, framed by extensive stone terracing and a cottage-style garden. Multiple covered porches, patios, and terraces encourage connection to the landscape in every season. Just 20 minutes from Hudson and Great Barrington, this beloved sanctuary offers space to create, reflect, and live fully in nature.
Courtesy: Copake Lake Realty Corp.
518-325-9741
A Home of Distinction -- there are two distinct sections of this 4+ BR, 4.5 BA, 2 office spaces, 3,666 sf home that is sited on 18.5 private acres. Wood-burning fireplace, 2 gas wood stoves. Pond with gazebo. The main section has 3 BR's, living room, family room, eat-in kitchen, access to the deck with Catamount views and an attached 2-car garage. The addition has a welcoming entrance, 1 BR. Here's what is really cool about this home -- there is a finished lower level that connects the addition to the main home. There you will find a extra room with radiant heat and exterior access, 2 offices and a spacious playroom. An opportunity not to be missed.
Courtesy: Brown Harris Stevens HV LLC
845-871-2700
Architecture meets nature in Hillsdale. A fully secluded getaway at the end of a private dead-end road on 7.3 pristine acres. This sunny 3-bedroom, 2-1/2 bath house is inspired by Scandinavian design and features 3 outdoor decks, with views of a spring-fed stream, a crystal clear pond, and deep green woodlands. Central AC for summer days and a wood stove for snowy nights. An ideal layout for working from home and for guests, this well-maintained house includes a ground-level walkout room which would be ideal for a studio or for entertaining. Reimagined by a fashion editor and creative director, 10 minutes from Great Barrington and 7 minutes to the Catamount Ski Resort, this property is situated between the Berkshires and the City of Hudson, with endless shopping, food and cultural destinations.
Courtesy: Columbia County RE Specialist
518-325-9784
Welcome to Copake Lake!! Sweet two-bedroom, one bath cottage, eat in kitchen, views of the lake from living room and one of the two bedrooms, nice big yard to enjoy outdoor fun. All appliances included. PLUS (As per Seller) water rights along that 20-foot stretch, a buyer may be able to agree with others in the area to extend the existing dock, which could be up to 60 feet into the lake! Property includes lake and water rights, and interested buyers can review the deed and survey with their attorney for further clarification or potential agreements regarding the dock use. Pretty Sweet!!! Sold 'As Is'
Courtesy: Compass Greater NY LLC
914-238-0676
Sited at the highest point in Hillsdale this modern home captures the world around while being incredibly private. Main house has tall ceilings tremendous natural light and doors bringing you outside from every space. Music room on the east side brings in the Berkshire hills with doors out to the breakfast patio. Office with en suite is off the entry. Second floor is the primary suite; everywhere you look you stop to take in the view, large bath with walk-in closet and laundry. The inner courtyard has a heated pool, sunken jacuzzi, outdoor shower, screened porch with fireplace and beautiful perennial gardens. Hidden off the drive is a guest cottage with open living area, bedroom and full bath.
Set on a generous 1.2 acre lot along the Agawamuck Creek, this legal 2-family property offers rare potential in a peaceful natural setting. Whether you restore it to a grand single family residence or maintain its multi-unit layout, the structure is partially demoed and ready for renovation. With direct creek frontage and nearby access to Summit Lake/Reservoir, this is a nature lover's dream. Located just min utesz to Hudson, Claverack and Taconic State Parkway, you'll enjoy both privacy and proximity to top dining, culture and outdoor recreation. Create your own dream home - or 2 - in a location that offers tranquility and convenience in equal measure.
A Visionary Masterpiece in Columbia County Redefining Country Living. Tucked away on over four serene, wooded acres along one of Columbia County's most coveted roads, this extraordinary 1,700-square-foot contemporary barn home is an architectural work of art a one-of-a-kind residence conceived and crafted by acclaimed designer Angela Patterson. Marrying bold architectural innovation with the tranquil beauty of the natural world, this singular home is a celebration of light, space, and refined rustic elegance. From the moment you arrive, it's clear this is no ordinary home. The striking octagonal form is not only visually stunning but intentionally designed to harmonize with its forested setting, blending modern geometry with pastoral charm. Soaring ceilings topped by a central cupola create a cathedral-like volume that feels both dramatic and grounding. Massive, custom-engineered pivoting picture windows turn each room into a dynamic canvas of nature, bathing the interior in natural light and framing every season in exquisite detail. Inside, the home unfolds in a fluid, open-plan layout that is as ideal for peaceful reflection as it is for stylish entertaining. Radiant-heated polished concrete floors provide warmth and modern sophistication underfoot, while a dramatic, floating propane-fired fireplace becomes a central sculptural element an eye-catching focal point that anchors the living space with effortless style. The open kitchen is a masterclass in both function and form, featuring sleek, top-of-the-line appliances and custom cabinetry that seamlessly flows into the dining and living areas, perfect for gatherings that are both intimate and grand. Two loft-like bedrooms offer tranquil sleeping quarters that echo the home's minimalist luxury, each complemented by spa-like baths crafted in glass and stainless steel for a clean, contemporary feel. Despite its sense of remoteness, the home is just minutes from the charming hamlet of Hillsdale, vibrant Hudson, and the rich cultural offerings of Great Barrington in the nearby Berkshires. Whether you're seeking a stylish full-time sanctuary or an idyllic weekend escape, this home delivers an unparalleled blend of privacy, accessibility, and luxury all just 2.5 hours from both New York City and Boston. For those who crave design without compromise, light without limitation, and a lifestyle defined by beauty, calm, and connection, welcome home.
Centrally located in Hillsdale, Columbia County, NY. Just about equal distance to Great Barrington, MA and Hudson, NY.This three bedroom, one bathroom, 1,000+ sf home offers a great level yard and a view of your own pond!The area is full of activities such as found at Catamount, the Harlem Valley Rail Trail (nothing motorized), Tanglewood, Copake Country Club, Copake Lake, organic farms, farmer markets and many farm-to-table restaurants.Be it by car (Taconic Parkway, I-90) or by train (Amtrak or Metro-North) this is a very special place to be.
Tucked away on a quiet, secluded backroad, this striking contemporary home offers the perfect blend of privacy, modern design, and convenience. With three thoughtfully designed levels, the main house features 4 bedrooms and 3 recently updated full bathrooms, providing ample space for both everyday living and entertaining.The top floor is dedicated to the serene primary suite, featuring a spacious bedroom and private bathroom for a true retreat-like experience. On the second (main) floor, you'll find a light-filled kitchen, open dining area, expansive great room, a guest bedroom, and a full bathroom. This level is wrapped in sliding glass doors that open onto a generous wrap-around deckideal for enjoying the peaceful surroundings or hosting outdoor gatherings.The lower level offers a cozy family room with a wood-burning stove, two additional bedrooms, a full bathroom, and a laundry area. This level connects seamlessly to the large mudroom, which links the main house to both the garage and the full garage apartment.The garage apartment provides flexible living space, complete with a full kitchen, bathroom, bedroom, and its own washer/dryer perfect for guests, extended family, or rental opportunities.While beautifully private, the location is highly convenient: just 10 minutes to Great Barrington, MA, 10 minutes to the Hillsdale hamlet, and only 20 minutes to Hudson, NY and the Amtrak station. Whether you're looking for a full-time residence or a peaceful weekend escape, this unique property offers the best of Berkshires and Hudson Valley living.Please note that with the attached garage apartment the home is close to 4,000 sqft for a total of 5 bedrooms and 4 bathrooms on the property.
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Hillsdale is located in New York. Hillsdale, New York has a population of 1,659. Hillsdale is less family-centric than the surrounding county with 13.6% of the households containing married families with children. The county average for households married with children is 22.64%.
The median household income in Hillsdale, New York is $81,293. The median household income for the surrounding county is $73,065 compared to the national median of $69,021. The median age of people living in Hillsdale is 53.4 years.
The average high temperature in July is 82.4 degrees, with an average low temperature in January of 12.4 degrees. The average rainfall is approximately 46.2 inches per year, with 53.4 inches of snow per year.
