Courtesy: The Kinderhook Group, Inc.
518-751-4444
Nestled along a private picturesque country dirt road--surrounded by a serene freshwater pond, a flowing creek and wooded acreage, this charming 2 bedroom log cabin offers the perfect escape. The expansive property spans 193 acres, with 18 acres located outside the Columbia Land Conservancy and Forestry Program, allowing for taxes to be reduced and privacy enhanced. Recently renovated with a stylish bathroom and living room expansion! Geothermal heat and air conditioning provides energy efficient utilities. The outside work of staining wood and painting gives the property a fresh feeling! An additional structure provides flexible space, ideal for use as a studio or creative retreat. Situated across 2 tax parcels in the towns of Austerlitz and Hillsdale, the location offers convenient access to Hudson, The Berkshires and Albany.
Courtesy: Columbia County RE Specialist
518-325-9784
Classic country homes like this one don't come on the market often and don't last long when they do. This 1933 Cape Cod home is new to the market after 49 years of stewardship by the current owner. The 1.5 acre parcel is deep, with an open and private back yard. In the front, the parcel is bordered by a year-round stream that is a tributary of the Roeliff Jansen Kill. Collins Street is one of Hillsdale most charming country roads and is located about 2 miles from Catamount Ski Area and the Massachusetts border, leading to all that the Berkshires have to offer. The stylish cape offers 1,630 sq.ft. of living space, with a bedroom and bath on each of the two levels. Upon arrival you are greeted by an enchanting front entrance into the spacious great room with built-in bookcase and living room with wood burning fireplace. In need of some updating, but priced to sell. Your tasteful design ideas and updates will bring this grand home from another era back to its glorious self for its 100 th birthday.
Courtesy: Coldwell Banker Advisor Realty
518-828-7111
Come see the new me!. I've had a face lift and you are sure to enjoy the gleaming hardwood floors and the updated kitchen with granite counters and new appliances. It's one level of easy living, and offers many wonderful features. Enjoy the spacious living room framed by a fireplace, or the cozy den which has one as well..The middle bedroom features sliders that open onto a deck, great to enjoy your morning coffee, or use as office space and let the wonders of the outdoors inspire you. A new roof, fresh paint, inside and out, new septic and more, mean less work for you and more time for fun. A wonderful opportunity just minutes from the hub of Hillsdale, Copake Lake, Catamount Ski area and the beautiful Bash Bish waterfalls. A brief drive will get you to Great Barrington or Hudson and its just 2 hours to NYC.
Courtesy: Four Seasons Sotheby's Int.
518-822-0800
Discover a truly singular retreat: a 1,700-square-foot, octagonal contemporary barn residence designed and built by a noted architectural designer. Set deep within more than four acres of pristine woodlands on one of Columbia County's most coveted roads, this home offers the rare combination of modern architecture, privacy, and effortless living. Expansive pivoting picture windows invite a constant play of light throughout the interior and frame the surrounding landscape as living art. Inside, the soaring cupola-topped ceiling and radiant-heated polished-concrete floors create a calming, loft-like atmosphere, anchored by a dramatic floating propane fireplace. The designer kitchen integrates seamlessly into the open living and dining spaces, making the home equally suited for quiet evenings or stylish entertaining. Two airy, loft-style sleeping areas, and two sleek glass-and-steel baths complete the thoughtfully curated layout. Every element of the home blends sophistication with simplicity—ideal for a buyer who values design, nature, and ease. Tucked away yet minutes from Hillsdale, Hudson, Egremont, and Great Barrington, the location offers instant access to the region's best culture, dining, and outdoor recreation. With NYC and Boston a little over 2 hours away, this property is the perfect full-time escape or effortlessly luxurious weekend base. A rare architectural and design statement, this steel-and-glass modern barn redefines country living for the buyer seeking something truly unique.
Courtesy: Stone House Properties, LLC
413-232-4253
This home on almost 4 acres with a private pond and scenic mountain views year-round, also abuts the Harlem Valley Rail Trail. It is within walking distance to the village of Hillsdale. Including the Roe Jan Brewing Co. IGA, the Hillsdale House, and the town park. Less then 5-min drive to Catamount; 25 min to Hudson NY, and 20 min to Great Barrington MA.
Courtesy: Four Seasons Sothebys Intl
518-822-0800
Discover a truly singular retreat: a 1,700-square-foot, octagonal contemporary barn residence designed and built by a noted architectural designer. Set deep within more than four acres of pristine woodlands on one of Columbia County’s most coveted roads, this home offers the rare combination of modern architecture, privacy, and effortless living. Expansive pivoting picture windows invite a constant play of light throughout the interior and frame the surrounding landscape as living art. Inside, the soaring cupola-topped ceiling and radiant-heated polished-concrete floors create a calming, loft-like atmosphere, anchored by a dramatic floating propane fireplace. The designer kitchen integrates seamlessly into the open living and dining spaces, making the home equally suited for quiet evenings or stylish entertaining. Two airy, loft-style sleeping areas, and two sleek glass-and-steel baths complete the thoughtfully curated layout. Every element of the home blends sophistication with simplicity—ideal for a buyer who values design, nature, and ease. Tucked away yet minutes from Hillsdale, Hudson, Egremont, and Great Barrington, the location offers instant access to the region’s best culture, dining, and outdoor recreation. With NYC and Boston a little over 2 hours away, this property is the perfect full-time escape or effortlessly luxurious weekend base. A rare architectural and design statement, this steel-and-glass modern barn redefines country living for the buyer seeking something truly unique.
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: 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: 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: 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: 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: 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.
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'
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.
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.
Exceptional Setting - Mountain Views- Well maintained RanchWell maintained ranch set on 8.3 open acres with beautiful views of the Taconic Range. The home with 3 bedrooms and 2.5 baths is lovely as is, and offers excellent possibilities for future additions and upgrades.. Enjoy expansive mountain views from both the open living space and the primary bedroom. A large deck provides great outdoor living/dining space, mature gardens and landscaping finish the property beautifully. Central A/C and a wood burning fireplace provide comfort year-round, and the sunroom is perfect for a library/office. Breezy Hill Rd is one of the most desirable and convenient locations in the Berkshires - 2 miles to Catamount Mtn Resort (skiing), 4 miles to the center of Hillsdale, 9 miles to Great Barrington and 20 miles to Hudson.
Set amongst the rolling hills of southern Columbia County, this c1942 antique farmhouse sits on seven acres with beautiful, pastoral views down the valley to the east. There is a separate studio, a three car garage and a potting shed on the property. Renovated top-to-bottom, the main house has both old world charm with its original hardwood floors, and modern comforts like new windows and roof, new mechanicals, new plumbing and electric & central air. On the main floor you'll enter into a tiled mudroom with a half bath. The kitchen is large with quartz countertops, and from the sink you have a lovely view of the ridge line. A peninsula island connects the space to a formal dining room, and the large living room is anchored by a wood burning fireplace. Upstairs there are two guest rooms that share a full bath and a beautiful primary suite with a walk-in closet. The third floor is finished and light filled, a perfect place for an office, play room or additional sleeping quarters. A long covered porch runs the length of the house, a perfect place to take in the east facing view. The shingle style studio is notched into the field, historically a guest house, it has been gutted and work started. The space has endless potential with vaulted ceilings and a woodstove, the interior clad in reclaimed barn wood. Central to both Hudson and Great Barrington, this bucolic country property is just 2h north of NYC.
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.
Dating back to 1928, this stately brick building originally a Masonic Temple is a stunning blend of historic charm and modern functionality. Meticulously restored and reimagined as an artist live/work space, it offers a unique opportunity to enjoy both a stately residence and/or a thriving business location.Set on a private, gated 0.54-acre lot in the charming Hamlet of Hillsdale, this property occupies a generous 7,656 square-foot footprint (comprising approximately 5,600 square feet over two floors plus an additional 2,800-square-foot basement). Inside, original architectural details abound, from soaring tin ceilings (14 feet on the second floor and 12 feet on the first and approx. 8 feet in the basement) to expansive steel casement windows that bathe the interior in natural light and frame serene views of the surrounding hills.The move-in ready layout features two bedrooms, three bathrooms (one full and two half baths), and a streamlined kitchen that caters to modern living without sacrificing historic character. Zoned for mixed use residential, commercial, and live/work the property sits perfectly between popular local businesses such as Roe Jan Brewing Co, The Hillsdale General Store, Tiny Hearts Flower Shop, and Cook & Larder, offering a delightful walkable lifestyle and instant community for business owners.Ideally located this landmark connects the Catskills to the Berkshires and provides easy access to Rensselaer and Dutchess County, with Hudson, Great Barrington, and Millerton all just a 20-minute drive away. Recognized on the National Register of Historic Places, this exceptional property is a true architectural paragon, a rare upstate gem where the precision and artistry of its original Masonic builders continue to inspire. Truly a once in a lifetime opportunity!
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.
