Hillsdale NY Homes for Sale

ADDITIONAL INFORMATION

Where Norman charm meets Hudson Valley splendor, "Dragonfly" stands as a fine example of country living - a rare 130-acre estate that marries grand European sophistication with the pastoral beauty of Claverack. Just twenty minutes from the cultural centers of Hudson and the Berkshires, this property strikes a balance between secluded sanctuary and connected countryside living.A winding private drive leads to the 7,200-square-foot Normandy-style residence with its stately stucco facade. Inside "Dragonfly'', the great room emerges as the heart of this extraordinary home, where soaring ceilings and dramatic walls of glass dissolve the boundary between interior luxury and a wall of white birches and the natural woodlands that lead to the private swimming pond beyond.Twin wood-burning fireplaces anchor this light-drenched gathering space, which flows to outdoor terraces and a dining room that adapts as gracefully to intimate family gatherings as it does to large dinner parties. The chef's kitchen has a professional-grade 48-inch range, generous island, and abundant storage, with a wall of french doors opening to a large terrace for summer gatherings.The primary suite is accessible via a sculptural staircase with a beautiful artisanal, wrought iron railing. The suite features a sitting room, spa-inspired bathroom with dual shower and soaking tub, walk-in closet, and a serene bedroom warmed by a gas fireplace. A private balcony offers a view over the estate's pastoral panorama.Four additional en-suite bedrooms are distributed throughout the residence, ensuring privacy and comfort for family and guests alike. The home's lower level spans the full footprint, including dedicated quarters for a caretaker."Dragonfly" is more than a home; it's a rare mix of architectural grace and a natural landscape that threads through the historic, stone walls to the private swimming pond and dock.For the discerning buyer seeking an extraordinary estate property in one of the Hudson Valley's most coveted locations, this singular offering is worth a visit.

ADDITIONAL INFORMATION

Welcome home." We finally got our lake house honey." This is the dream of many, the memories of your home at the lake will remain beautiful from childhood to retirement. Our custom ranch has so many extras. This beauty offers 3 good-sized bedrooms upstairs, and two additional bedrooms/ office downstairs. The setup is a mother-daughter. Two kitchens, two living rooms, separate bedrooms, and separate entrances all connected from upstairs. The owners have lived in this home for 27 years. It's been their dream home. They describe it as "the most tranquil place on earth." They lovingly cared for it. Upgrades include: an updated heating system, roof, whole house generator, and updated septic system 1,000 gallon concrete. There are 1.10 acres of beautiful property to explore, plant a garden, and make your oasis. The lake is slightly visible from the backyard not lakefront but truly convenient. There is a right away for access at the community entrance. One of the most beautiful features is the three-season sunporch. Right off the porch is a double deck. Loads of storage. The owner states no water issues and the house is well insulated. He has records dating back to 1997. This is a solid home with plenty of room for extended family or possibly rent out the lower level for additional income and let this lake home pay for itself. COPAKE LAKE Conservatory is a wealth of information. Hudson, NY, and Great Barrington, MA. are convenient for shopping and other adventures. Have lunch or dinner at the Greens County Club and play 18 holes on the well-manicured golf course. Get out the fishing poles and pack your bags; it's lake time. Appliances: Gas RangeWater Softener Owned BuildingAreaSource: Other, ConstructionDescription: Aluminum Siding, Vinyl Siding, ExteriorFeatures: None, Flooring: Ceramic Tile, FoundationDetails: Block, InteriorFeatures: Storage, LaundryFeatures: Gas Dryer Hookup, In Basement, Laundry Room, Washer Hookup, LotFeatures: Back Yard, Front Yard, OtherEquipment: Fuel Tank(s), Generator, Utilities: Propane,

ADDITIONAL INFORMATION

Now You Can See Around Corners: Discover this extraordinary one-of-a-kind 1,700-sf octagonal contemporary barn home, conceived and built by its visionary owner, architectural designer Angela Patterson, and tucked away on more than four acres of woodlands on one of the most desirable streets in Columbia County. Boasting huge, pivoting picture windows that invite a flood of natural light and beautifully frame the natural surroundings, this one-level architectural gem offers a unique blend of modern elegance and rustic charm and truly re-defines country living. Inside, a soaring ceiling crowned by a cupola, as well as radiant-heat polished concrete floors enhance the airy, open-plan design. There's also an expansive floating propane-fired fireplace, a fully equipped designer kitchen that flows seamlessly into the living spaces, two loft-like bedrooms and two glass-and-stainless steel baths. This home is perfect for modern and sophisticated living and entertaining and is situated to provide ultimate privacy while being minutes from the charming Hillsdale hamlet, Hudson, and the cultural hubs of Egremont and Great Barrington in the Berkshires. A mere 2.5 hours to either NYC or Boston, this residence is an ideal full-time or weekend retreat for those seeking luxury, relaxation, tranquility, and convenience.

ADDITIONAL INFORMATION

Contemporary compound perched amongst the oaks with spectacular sunset views over the hills and dale of Hillsdale. The 3 bedroom, 2-1/2 bath 2,218 square foot main home has a tree-top wrap-around deck with access from both the great room and a main floor primary en-suite which includes a laundry area, walk-in closet, and a bath configured with double sinks, separate shower and tub. The 25' x 22' living/dining area features a massive wood burning fireplace, vaulted 14 foot ceilings and picture windows offering a sweeping view overlooking the valley, pond and the hills beyond. The multi-level home also offers two lower level bedrooms with a full bath, and a few steps up from the main living area you will find a family room or office. Also on this level is the eat-in galley kitchen which is adjacent to a sky-lit yoga studio. The prior owner (a noted craftsman) had a well-ventilated workshop a few steps down from the main level and accessible from the attached two-stall garage, which could be whatever you need it to be: additional storage, a new in-house gym?From the home's thoughtfully planted entrance courtyard, follow the bluestone path to the detached garage, showroom and workshop, which can be reconfigured to your needs. With two very large half baths and two levels of open space, this somewhat blank slate can be reconfigured for whatever you desire -- a tremendous gathering place, a display space for large collections, a studio? In addition, this 4+ acre property is part of the Overlook Development association which maintains walking trails and a swim pond, within a short walking distance. Bring your vision to this wonderful property, which offers so much and has even more potential.

ADDITIONAL INFORMATION

Nestled on over 4 acres of serene land, this property features a private pond, fenced garden and renovated cabin offering a large studio living space. An attached 1-car garage, and wrap-around deck complete this cozy home. Additionally, there is a potential building site where an old abandoned home currently stands, offering opportunities for expansion.Situated on a quiet country road along the border of Massachusetts, this property ensures privacy while still being easily accessible. Enjoy the convenience of being just a short drive from Great Barrington, and only 15 minutes from Hillsdale, NY, and 15 minutes to the Mass Pike.Whether you're looking for a peaceful retreat, a weekend getaway, or a place to call home, this unique property is ready for new ownership to take it to its next chapter!

ADDITIONAL INFORMATION

Discover the charm of this 1800s cedar-shingled home on 29 scenic acres in Hillsdale. The property features a heated pool, private tennis court, and meticulously maintained grounds. With 4 spacious bedrooms and 3.5 baths, it offers comfort and elegance. The living room has a working fireplace and opens to a bright dining room with a bluestone floor. The main-floor primary suite also has a fireplace for cozy nights, and an additional ensuite bedroom offers guest privacy or serves as a den. A three-season porch with a propane stove overlooks the gardens. Upstairs, find two more bedrooms and a full bath. Framed by stone walls, a serene pond, and fenced vegetable and floral gardens, the property is perfect for outdoor lovers with hiking trails leading to Catamount ski trails. Additional amenities include a three-car garage and generator, as well as proximity to Hillsdale Center and Great Barrington. A rare find in the Berkshires!

ADDITIONAL INFORMATION

Secluded Hillsdale Contemporary on 27.7 acres with incredible far reaching views. Located off a scenic country road, the long private driveway leads to this 2200 square foot home. Originally built in 1970, the house has been upgraded with new windows and sliding doors which create walls of glass for enjoying the natural beauty of the surrounding landscape. The house features 3 bedrooms, 2.5 baths, a light filled great room with wood burning fireplace, maple floors throughout, cedar lined closets and cedar shake siding, metal roof, covered patio entry and an expansive wraparound deck. The detached 2 car garage has potential for a number of other uses. The property is a combination of open and wooded land with a meadow area and a spring fed pond. Wonderful area for outdoor enthusiasts with skiing, hiking and the rail trail close by. Only 8 minutes to Catamount Mountain Resort, 16 minutes to Great Barrington Airport, 30 minutes to Tanglewood and 35 minutes to Hudson Amtrak Station.

ADDITIONAL INFORMATION

Minutes to Great Barrington, this 300 acre wilderness provides waterfalls, Stream frontage, pond frontage and something for every outdoor enthusiast. Own your own mountain with trails throughout for hunting, hiking and camping. Build your dream house overlooking a stocked pond and classified trout stream while staying in the 3 bedroom 3 bath caretakers house. The possibilities are endless. Swim all summer in your own pond. Pull a trophy buck in the fall. Hike to the peak and back country ski down in the wintertime. Be the first to catch a trout in your own private trout stream.

ADDITIONAL INFORMATION

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 captures 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.

ADDITIONAL INFORMATION

Perched at the top of the hill sits a curated, modern home overlooking the valley with stunning views of the Catskills and breath-taking sunsets. Next to the 1,000 acre Rhinestrom Hill Audubon Society wildlife sanctuary in Hillsdale, this perfect getaway is private yet minutes to everything. Grand room with fireplace, wet/coffee bar, and a wall of glass. Fully-equipped chef's kitchen. Wideboard, rift-sawn White Oak flooring. 3 ensuite bedrooms on main level. 5.5 baths. Primary suite with spa bath - double showers, dual vanities, soaking tub. Custom millwork throughout. Lower level playroom, movie theater, and sauna. Home office with separate entrance that could be used as an additional bedroom with full bath. Screened porch with infrared heaters and outdoor television. Heated saltwater pool with automatic cover, extensive hardscape patio, mature landscaping, fire pit, and storage shed/playhouse. Pool bunkhouse has two full-size day beds to sleep additional guests, a kitchenette and its own full bath. Geothermal heating & cooling. Whole-house backup generator. Oversized, 2 car garage.

ADDITIONAL INFORMATION

Nestled into the hillside, this property is known as Springhill Farm, which dates back to the 1700s, an artist retreat. Since 2017, it has been recreated to combine a comfortable live and work environment. A Scandinavian inspired home and apartment built in 2019 & 2020 offer modern amenities and create a peaceful atmosphere. The 2 bedroom, 1 bath house features a large living space with a cozy woodstove for cooler months and large deck for entertaining and taking in the landscape. A barn apartment offers additional living space ideal for guests or rental income. Outside enjoy the expansive 25X50 barn, Cranse Creek, walking paths to a small pond, a fire pit, and an additional studio space. This property offers so much opportunity to live and work while enjoying the surrounding nature. With established rental history,Springhill Farm is ready to continue its journey to the next level.

ADDITIONAL INFORMATION

Located down a private winding drive The Passive House is an architect-designed modern home set amidst 15.7 wooded and pastoral acres. The home was designed and constructed to attain a rigorous level of energy efficiency and is a certified passive house (certified by the Passive House Institute US (PHIUS)). Conceived as a fossil-fuel free, all-electric home, solar panels work to bring this house close to net-zero. An ERV (Energy Recovery Ventilator) system is built into the HVAC, ensuring that fresh, clean air is circulating throughout every room at all times. The home is positioned to capture southern light and distant views. A bright, welcoming foyer leads to the first wing, which includes a bedroom, office space, full bathroom, and mechanical room. Steps lead past a powder room into the heart of the home a spacious, open-concept kitchen / dining / living area featuring 13-foot ceilings and floor-to-ceiling sliding doors that frame bucolic meadows and Catamount Mountain views. Beyond the living room, the west wing of the home has a media room/second living room, and a hall that leads to the additional two bedrooms, a second full bath, and the primary bedroom with ensuite bathroom. All bedrooms feature high quality triple glazed windows and doors. Enjoy indoor spaces that flow easily to the outdoor spaces creating a beautiful modern aesthetic blending seamlessly with nature. A 3-car garage pre-wired for EV charging and back bluestone patio complete this offering. Located in Hillsdale just minutes from the hamlet, 15 min to Great Barrington, and under 30 min to both Hudson and Millerton.

ADDITIONAL INFORMATION

A Lake house in the country is perfect for those seeking a simple way of life. You'll feel like you're living in a storybook. Watch your story unfold before your eyes. Leona's Country Cottage is not your average cottage. It was architecturally designed and built to last many years to come. A new rebuild from the foundation up between 2020-2021 With all new requirements for efficiency and new code requirement for electrical and plumbing, you're getting one of the best constructed homes on Copake Lake. It's a perfect blend of modern craftmanship and comfort. Regarding value consideration, Copake Lake Real Estate is rarely available in this private community and has no HOA. New builds are selling from 620k to millions. The construction plans, survey and CO are available upon your request. There is direct access to the lake from the cottage. A newly constructed staircase will bring you to your dock. Deeded Right away & lake rights come with your ownership and a shed for storage. Important details: Septic is a 500 Gallen Poly Septic installed in 2011. Propane is owned, Electric is 200amps. 3 Ductless systems -Provides heat and air. Electric Company is NYSET. Yearly cost 1200. COPAKE LAKE Conservatory is a wealth of information. All appliance included in sale. Hudson NY and Great Barrington Ma. is convenient for shopping and more adventures. Have lunch or dinner at the Greens County club and play 18 holes on the well-manicured golf course. Get out the fishing poles, pack your bags its lake time. Note: Part of the front steps up to the house are owned by neighbor to the left. Survey pin near steps angles to metal post. Right away to lake is for multiple people to use as per deed. The dock, shed and lower-level land is owned by the current owner- The right of way is for 3 neighbors for access only as per deed. Additional Information: Amenities:Stall Shower, Appliances: Electric Water Heater ConstructionDescription: Vinyl Siding, InteriorFeatures: Built-in Features,

ADDITIONAL INFORMATION

Purchased by the Foster family in 1790, this property encompassed the majority of what is now the Historic Hamlet of Hillsdale. Sited in the center of the Hamlet, this Greek Revival home, built in 1810 by Isaac Foster, who inherited the land from his father. Prior to 1790, the property was in the family of Catherine Van Renssalaer Schuyler - mother-in-law of Alexander Hamilton. The home has been recently renovated to preserve its historic value as the third oldest house in town. With its large backyard and mature trees, the property was fully restored to respectfully celebrate its grandeur and elegance. This designer-ready, stylish farmhouse offers a unique opportunity to anyone wanting a turnkey property in the majestic Hudson Valley. The renovation included a new dual-zoned centralized heat and cooling systems, new plumbing, electrical wiring, water heater and furnace, structural re- stabilization, and a replaced roof. All new appliances were installed, including an upstairs laundry space with stacked Samsung washer and dryer. The walls, plaster and paint have been fully re-finished. Antique glass was used to restore the period windows, and original wood flooring was kept and restored to offer warm and cozy interiors. Upon entering, there are warm oak floors, view of both the living-room and formal dining room, windows' with unique casings, an example of Greek Revival design, and the fireplace features two original miniature carved Greek friezes guarding either end of the mantel. The spacious kitchen, a walk-in pantry, granite countertops, new Bosch appliances, and informal dining space. Carrara marble in both bathrooms with a full suite of traditional-styled fittings. The primary suite features a vanity set, soaking tub, separate shower. There can be up to 4 bedrooms, (including a first-floor mother-in-law style apartment with private entrance and bathroom with a shower). The home offers a flexible floor plan for use as a residence, a business, or dual use - the building is zoned as both commercial and residential. Situated halfway between Hudson, NY and Great Barrington, MA, walking distance to amenities of Hillsdale Hamlet, a general store, florist, kitchen store, brewery, restaurants, coffee shops, and grocery store with wine shop. Catamount skiing, hiking trails, lakes, and walkable access-point to the Rail Trail.

ADDITIONAL INFORMATION

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.

ADDITIONAL INFORMATION

For the first time on the market in nearly 60 years, Underwood Farm is a remarkable 117 acre spread across the rolling ridgelines of Hillsdale and harboring a magnificent, roaring piece of the Roeliff Jansen Kill. Once a thriving dairy farm, this offering includes an authentic Greek Revival farmhouse with all of its architectural integrity in place: wide plank wooden floors, original sash windows with wobbly glass surrounded by detailed trim work and a sweeping center hallway with 5 bedrooms, 2 full bathrooms, 3 fireplaces, a small barn and a large commercial dairy barn with 3 stories. The house enjoys exceptional proportions and far-reaching views of the Catamount ski slopes across a lovely field visible from almost every room. Driving into the property, once you cross the Roe-Jan, a natural fit for a new home sight reveals itself high on a knoll with the sounds of water breaking across stones downstream and the famed hills of Hillsdale are seen in every direction. Build your dream home and enjoy rental income from the original farmhouse and lease the acreage of fertile fields to nearby farmers in need of soil or hay or try your own hand at wildflower farming. Options abound.

ADDITIONAL INFORMATION

The House on Breezy Hill is a completely revitalized contemporary colonial situated aloft one of the most sought-after locations in Columbia County. Every element of this beautiful home was thoughtfully conceived and expertly crafted, making it the perfect opportunity to acquire an extraordinary property. Arrive via a circular driveway to a newly constructed oversized two-car garage. Enter the home via a beautifully designed passageway that leads to a media room where radiant concrete floors ground a space wrapped in shiplap. Offering surround sound and an elegantly concealed closet, the media room is both comfortable and practical. Steps lead to a kitchen and living room where floor-to-ceiling windows and custom sliding doors invite ample light into the space, highlighting the expert craftsmanship that defines this home. The kitchen offers a generous island space with marble countertops and elegant marble wall. Viking appliances including a six-burner gas range are sure to delight the consummate chef. The living space is centered around a gas fire place and flows seamlessly between the kitchen and dining area. Step through the floor-to-ceiling sliding doors onto a wrap-around deck of generous proportions where views of northern Hillsdale and the Taconic Hills captivate. Ascending the stairs to the second floor, a generous landing gives way to a primary bedroom that features double height ceilings. A private balcony offers an opportunity to take in the vista from a more secluded vantage point. There are three additional bedrooms of generous proportions, one of which boasts panoramic views of the landscapes. All three bathrooms offer luxury finishes and have been executed with meticulous detail. Located seconds to Catamount Mountain, 15 minutes to Great Barrington and 25 minutes to Hudson, this property is ideally situated to take full advantage of the abundant recreational and cultural attractions of the Hudson Valley and Berkshire Mountain regions.

ADDITIONAL INFORMATION

Indulge in ultimate luxury living in the heart of Columbia County, New York! This magnificent modern home is a true gem that showcases breathtaking views of the stunning Berkshire Hills and majestic Catamount Mountains. Step inside and be greeted by a double-height hallway leading to a dining room with floor-to-ceiling windows, providing a spectacular view of the pool area and stunning scenery beyond. The chef's kitchen is a dream come true for any culinary enthusiast. It opens to a spacious two-story Great Room with a warm and inviting fireplace and floor-to-ceiling windows that frame the stunning views. If you need a peaceful retreat, a cozy loft library is just a staircase away. Behind the Great Room, there is also an intimate home office space with a built-in closet, bookshelves, and bar, and can be used as an additional guest bedroom. The first floor features three luxurious guest bedrooms, each with access to full baths and a gym with sauna and pool access, offering the ultimate relaxation experience. The upper level boasts a magnificent master suite with a double-sided fireplace, an oversized bathroom, and a private terrace. There is easy access to a grand roof deck overlooking the shimmering pool, inviting hot tub, and outdoor kitchen. Perfect for entertaining! The lower level of this exceptional home is complete with a state-of-the-art movie room, a convenient laundry room, and a half-bath. Situated on 10+ acres of beautifully landscaped property featuring expansive lawns and open country fields, this is the perfect country escape you've been searching for in Columbia County! Don't miss out on this incredible opportunity to experience luxury living at its finest.

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