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23 Houses For Sale in Hillsdale, NY

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$5,250,000Est. Payment
5 Beds | 5 Baths | -- Sqft
199 Dawson Rd, Hillsdale, NY 12529
House For Sale

Sitting atop 230 tranquil acres consisting of fields, woods and expansive views, the home was built in 2006, is 7000+/- sqft, with 5 bedroom and 5 bath has everything one could want in either a full time residence or get away retreat. Miles of trails encompass the property perfect for hiking, biking or ATV's. Tennis court, treehouse, Basketball court, and large patio surround a nearly 3 acre spring fed swimming pond. Inside one will find the kitchen with top of the line appliances and informal dining area. Library and sitting room parallel each other on either side of the first floor with a billiard room and exterior doors leading to the patio located in the north west corner. The second floor is accessed from the central hall with two bedrooms sharing a full bath on one end and primary

$425,000Est. Payment
2 Beds | 1 Bath | 966 Sqft
42 Tory Hill, Hillsdale, NY 12529
House For Sale

English country charm: tasteful, simple and understated. Two cottages and one shed. Cottage 1: Main house, 2 bedrooms, beautiful light, cooks kitchen looks out to garden and Writer's cottage. Cottage 2: Writer's cottage or refuge, guest room or studio. Wonderful space, beautiful windows, high ceiling, inspiring. Shed: Solid, sweet, sits along a little creek with a porch handy for a nice stack of dry firewood. Lovely 2 acres of open and lightly wooded land. 3 minutes to Random Harvest,1.5 miles from the light in Hillsdale and 15 minutes to Hudson. If I ever go looking for my heart's desire again, I won't look any further than my own back yard. Because if it isn't there, I never really lost it to begin with.'' ? Noel Langley, The Wizard of Oz

$459,000Est. Payment
3 Beds | 2 Baths | 2,600 Sqft
957 Mitchell St, Hillsdale, NY 12529
House For Sale

A complete rehab by local master contractor - new roof, siding, windows, electric, plumbing, foam insulation, heat, a/c, bathrooms, kitchen, walls and floors! Living space is on first floor with a two-car garage attached to house with door into kitchen/dining/living room. Kitchen has all new stainless steel appliances and cabinetry, with an island holding the sink and to sit at as well as space for a dining table. Living room has a working wood burning fireplace with mantle. Bedrooms are off living room, all good sized and the Master has an ensuite bathroom. One of Bedrooms has a sliding glass door to a cement patio with country views. Space upstairs for more bedrooms or playroom or office, currently unfinished, but a blank canvas for your ideas. Basement is clean but unfinished with hookup for washer and dryer. This lovely house sits on .88 of an acre, semi-secluded and is ready for you to move in and start living the country life!

$3,500,000Est. Payment
4 Beds | 2 Baths | 2,377 Sqft
559 Hunt Road, Hillsdale, NY 12529
House For Sale

1890 Colonial Farmhouse with four bedrooms, almost 3,000 square feet and on 240+/- BEAUTIFUL acres. The property is ideally situated and perfect for a country estate or prime for development. Previously a working dairy farm, the land is mostly rolling fields under cultivation, woodlands with trails, and the most sensational views of the underlying valley and Catamount Ski Area. The maintained pastures and meadows allow for animals and/or livestock. Multiple out-of-this-world building sites with stunning classic Hillsdale views, from which, in extreme solitude and privacy life and the bucolic surroundings can be contemplated. The property is 2 hours from NYC, within a short drive of the Capital Region and equidistant between Hudson and the Berkshires. Come discover this oasis of solitude and tranquility for yourself. You'll never want to leave! 1890 Colonial Farmhouse with four bedrooms, almost 3,000 square feet and on 240+/- BEAUTIFUL acres. The property is ideally situated and perfect for a country estate or prime for development. Previously a working dairy farm, the land is mostly rollin

$2,075,000Est. Payment
3 Beds | 3 Baths | 2,091 Sqft
61 Dugway Rd, Hillsdale, NY 12529
House For Sale

This unique offering of a new construction house with custom floor plans available is the perfect opportunity. The land consists of eight separate adjoining parcels. Four in the town of Hillsdale, and four in Austerlitz. See lot and tax info in documents. More than 165 prime combined acres located in Hillsdale and Austerlitz, NY in the highly desirable Hudson Valley. This property has can be accessed by appointment from the private road, Knox Lane. There is an unpaved road in place and a cul-de-sac; ready for your next big project! The property has plenty of locations for prime homesites with gorgeous views, Much of the property is currently wooded offering privacy and excellent hunting opportunities.

$10,000
$199,900Est. Payment
3 Beds | 1 Bath | -- Sqft
6 Brady Lane, Hillsdale, NY 12529
House For Sale

This updated 1930's cape is sure to please. The kitchen and bath have been given makeovers and feature new appliances, a breakfast bar and sliders that open to the wrap around decking. There's a family room in the rear with knotty pine walls and a wood stove hook up in the corner. Some of the the other improvements include new carpeting and fresh paint in and out making it a ready to move into home. A nice level back yard and two sheds round out the picture. A great country home suitable for full time or weekend use and minutes to Bash Bish Falls and Copake Lake as well as many activities in the Berkshires! Taconic Hills School District

$149,000Est. Payment
2 Beds | 1 Bath | 800 Sqft
3298 County Route 7, Copake, NY 12529
House For Sale

Copake Lake cottage with shared dock rights. Gives you access to the water, while being just a short drive to other attractions like skiing, golf, music venues, hiking and farms. This particular area is home to many summer cottages, like this one, many of which have been updated. This handyman special is waiting for its' chance. Roughly 30 minutes or less to both Hudson, NY, and Great Barrington, MA. Sold As Is

$674,999Est. Payment
1 Bed | 1 Bath | -- Sqft
243 N Pumpkin Hollow Road, Hillsdale, NY 12529
House For Sale

Have you always dreamed about building a house with the best views? This is your chance. With a little more than 24 acres and 360 degree views of nothing but trees, mountains and the great outdoors, this site is perfect for your future building project. Live in or use the spacious 1 bed, 1 bathroom cabin while you build to start enjoying your new location right away. You'll be fully disconnected up here but only a short drive away to Copake Lake, Catamount Ski Area, Hudson and Great Barrington, MA.

$55,000
$795,000Est. Payment
6 Beds | 6 Baths | 2,882 Sqft
9315 State Route 22, Hillsdale, NY 12529
House For Sale

Three buildings + heated In-ground pool!! Gorgeous historic property in the hamlet of Hillsdale, formerly 'The Bell House Bed & Breakfast' & Red Fox Antiques'. 19th century home with old-world style. Huge wrap-around porch surrounded by mature landscaping that leads to the classic front door with original sidelights. Enter to a beautiful stairway and hall leading to the living room with fireplace, den/library with fireplace, enchanting dining room, kitchen, laundry and bath. The second floor features four bedrooms, three full baths and relaxing sitting area. In addition to the main house, there is a 22x32 heated barn, formerly known as 'Red Fox Antiques' Plus a Carriage house, w/a legal two-bedroom, two-bath apartment above, both built in 1900's. Just under 4 acres, walking distance to everything Hillsdale has to offer. The home is built to last a lifetime, with original details inside and out....and lets not forget the 21x41 in-ground pool. Amazing opportunity & Motivated Sellers.

$699,000Est. Payment
3 Beds | 3 Baths | 3,052 Sqft
35 Stone Ledge Rd, Hillsdale, NY 12529
House For Sale

SECLUDED MOUNTAIN TOP POST & BEAM - A wrap around deck allows for the enjoyment of nature. This contemporary offers 3 bedrooms, 2.5 baths on 14.2 acres (2 lots). Open First floor with open plan newly renovated kitchen, dining room, living room and den/first floor bedroom, foyer and half bath with laundry. Second floor primary bedroom suite with updated bath with tub and shower, guest bedroom and bonus room share bath with tub, and a indoor spa with hot tub and sauna. Two fireplaces and hardwoods throughout. Attached tool shed off spa. The house is on 6.2 acres being sold with an additional lot of 8 acres. Located in Hillsdale - close to all Columbia County and Berkshire County attractions.

$55,000
$795,000Est. Payment
6 Beds | 6 Baths | 2,882 Sqft
9315 Route 22, Hillsdale, NY 12529
House For Sale

Three buildings + heated In-ground pool!! Gorgeous historic property in the hamlet of Hillsdale, formerly 'The Bell House Bed & Breakfast' & 'Red Fox Antiques'. 19th century home with old-world style. Huge wrap-around porch surrounded by mature landscaping that leads to the classic front door with original sidelights. Enter to a beautiful stairway and hall leading to the living room with fireplace, den/library with fireplace, enchanting dining room, kitchen, laundry and bath. The second floor features four bedrooms, three full baths and relaxing sitting area. In addition to the main house, there is a 22x32 heated barn, formerly known as 'Red Fox Antiques'... Plus a Carriage house, w/a legal two-bedroom, two-bath apartment above, both built in 1900's. Just under 4 acres, walking distance to everything Hillsdale has to offer. The home is built to last a lifetime, with original details inside and out....and lets not forget the 21x41 in-ground pool. Amazing opportunity & Motivated Sellers. Cultural attractions throughout the year include: Tanglewood Music Festival, The Berkshire Choral Festival, Shakespeare & Co. Theatre, Jacob's Pillow, Norman Rockwell Museum, Three Shaker Villages, Olana, home of Frederick Church, The Berkshire Theat

$325,000Est. Payment
4 Beds | 2 Baths | 2,479 Sqft
84 Connelly Road, Copake, NY 12529
House For Sale

Safe haven. Tucked away in the scenic hills of Craryville, this 2 story cape will bring the solitude you have been craving. Peaceful setting. Minutes to Copake Lake, water sports and golf. Near Berkshires. 20 minutes to Hudson, Amtrak. Lower level has fantastic party room opening to patio. A propane fireplace adds coziness in the winter months. See and hear no neighbors!

$1,350,000Est. Payment
3 Beds | 3 Baths | 2,620 Sqft
68 Peartree Ln, Copake, NY 12529
House For Sale

MESMERIZING VIEWS Walls of glass doors access the magnificent serenity and magic of every season; the ultimate house for indoor-outdoor living.Three bedroom, three bath, eat-in-kitchen, dining, sumptuous living room, with library/den, laundry room and two car garage. A team of leading Architects have combined warm eco-friendly materials, clean and spacious lines, high ceilings and thoughtful systems to create delightful sun drenched indoor spaces. Glass walled Living areas with 15' vaulted ceiling and fireplace, a perfect space for entertaining, or just relaxing, surrounded by captivating views. Wood floors and radiant floors throughout living spaces and bedrooms with glass, marble and stone bathrooms. Gracious stone patios and an outdoor kitchen make this the perfect escape from city stress the only sound are the wind through the mature tress and singing birds. Perfect location to enjoy and experience the best of the Hudson Valley

$689,000Est. Payment
3 Beds | 3 Baths | 2,583 Sqft
555 Overlook Road, Copake, NY 12529
House For Sale

I Wonder. It's the house that you've driven past and can't seem to get out of your mind. This 3 BR, 2.5 BA, 2583 sf Adirondack-style home is sited on 6+ acres. Private pond, mountain views. In close proximity to Bash Bish Falls, Catamount Ski/Aerial Park/Zip Line and the Berkshires. The home has wood floors, open floor plan, stainless appliances, wood-burning insert in the living room fireplace, vaulted ceiling. Master en-suite on the main living level. The master bath has both a soaking tub and custom walk-in over-sized shower. Access to the hot tub is from both the master bath and the living room. The upper level offers two bedrooms, one bathroom and a sitting area. The walk-out basement has 9' high ceilings and a wood stove. All this is located about equal distance between trending Hudson, NY and quaint Great Barrington, MA. It's about 2 hours to NYC and 2.5 hours to Boston. Hudson Valley country living in southern Columbia County, NY. Just loving it!

$26,000
$749,000Est. Payment
2 Beds | 2 Baths | 2,913 Sqft
2036 Route 11, Call Listing Agent, NY 12529
House For Sale

Up a private drive, and OUT OF THIS WORLD, waits a 2900 sqft 2 Bedroom, 2 Bath home with 17 x 8 foot PDC SWIM SPA INDOOR EXERCISE POOL on 40.7 acres in Taconic Hill Schools. You will love the dedicated 19 x 37 exercise room that houses the pool. You will love the light filled, airy spaciousness throughout the house. AND you are going to love the master suite with its 13x12 luxury bathroom with tile radiant-heat floor. Sitting by the fireplace in the open floor-plan living room / dining room will leave your cheeks rosey and charmed during those cooler evenings. The dining area is also open to the kitchen, with its ALL-DARK STAINLESS STEEL LG appliance suite, GRANITE counters, trash compactor and garbage disposal. There is a dedicated HOME-OFFICE space with room for three desks. And above the master bedroom is space available for an additional room ( no current access but the raw space is framed out up above). At the opposite end of the house from the master bedroom is the guest bedroom, with another full bathroom, the pantry and mudroom. There is easy to access to the 35 x 30 garage. And this is not your every-day garage -- convenient for tractors or snowmobiles, you can DRIVE STRAIGHT THROUGH - there are automatic doors on both sides of the main space! And easy walk-up to the 30x30 garage attic storage - this could become another room, office, or great media room. Wrap-around covered decking and a beautiful lawn awaiting your landscaping touches, this property is a great value. INSULATED CONCRETE forms, WHITE OAK flooring, easy to maintain vinyl siding, and a 30-year architectural shingle roof with leaf-cover-gutters - you've got very little to worry about here. Enjoy great mountain-bike or ATV trails throughout the property. 3 minutes to the Taconic State Parkway on ramp, 20 minutes to the Amtrak station, and 2 hours to Midtown Manhattan.

$20,000
$359,000Est. Payment
3 Beds | 2 Baths | 1,256 Sqft
1989 County Road 11, Hillsdale, NY 12521
House For Sale

Quaint, private, and sun-filled...this cozy, country saltbox home boasts charm galore! Sip your morning coffee overlooking beautiful views of your lower fields from your covered, front porch or spacious, side deck. Stone steps and tiered flower beds lead you into a large, eat-in kitchen. Through the kitchen is the living room with vaulted ceilings, a bright bay window, and wide french doors leading to the rear patio and large backyard. A bedroom and full bath downstairs with washer/dryer is great for family and guests. Upstairs is another full bathroom and 2 bedrooms with picturesque Berkshire Mountain views. The large, dry basement affords you your very own root cellar, plenty of room for storage, and a wood stove that can be used in place of the furnace. The 3.57 acres are perfect for growing your own fruits and vegetables while leaving plenty of room for children and entertaining. Green thumb? Grow your favorite plants in your own personal greenhouse. The home is in a wonderful location just 9 minutes from the highly regarded Waldorf Hawthorne Valley School, 15 minutes to Hudson, 25 minutes to Great Barrington, and only 20 minutes to skiing at Catamount, with easy access to the TSP! To schedule a private showing, contact: Luke Roach - The Truss Group 845-546-6673 cell [email protected]

$26,000
$749,000Est. Payment
2 Beds | 2 Baths | 2,913 Sqft
2036 County Route 11, Hillsdale, NY 12529
House For Sale

Up a private drive, and OUT OF THIS WORLD, waits a 2900 sqft 2 Bedroom, 2 Bath home with 17 x 8 foot PDC SWIM SPA INDOOR EXERCISE POOL on 40.7 acres in Taconic Hill Schools. You will love the dedicated 19 x 37 exercise room that houses the pool. You will love the light filled, airy spaciousness throughout the house. AND you are going to love the master suite with its 13x12 luxury bathroom with tile radiant-heat floor. Sitting by the fireplace in the open floor-plan living room / dining room will leave your cheeks rosey and charmed during those cooler evenings. The dining area is also open to the kitchen, with its ALL-DARK STAINLESS STEEL LG appliance suite, GRANITE counters, trash compactor and garbage disposal. There is a dedicated HOME-OFFICE space with room for three desks. And above the entire first floor is space available for an additional room ( no current access but the raw space is framed out up above). At the opposite end of the house from the master bedroom is the guest bedroom, with another full bathroom, the pantry and mudroom. There is easy to access to the 35 x 30 garage. And this is not your every-day garage -- convenient for tractors or snowmobiles, you can DRIVE STRAIGHT THROUGH - there are automatic doors on both sides of the main space! And easy walk-up to the 30x30 garage attic storage - this could become another room, office, or great media room. Wrap-around covered decking and a beautiful lawn awaiting your landscaping touches, this property is a great value. INSULATED CONCRETE forms, WHITE OAK flooring, easy to maintain vinyl siding, and a 30-year architectural shingle roof with leaf-cover-gutters - you've got very little to worry about here. Enjoy great mountain-bike or ATV trails throughout the property. 3 minutes to the Taconic State Parkway on ramp, 20 minutes to the Amtrak station, and 2 hours to Midtown Manhattan.

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