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42 Homes 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

Remodeled home on Mitchell Street in Hillsdale This completely remodeled home by local Master Carpenter, is situated on a sought-after street in Hillsdale, just waiting for you to move in. It sits on .88 of an acre, which is semi-secluded with country views. Living space is on first floor with open kitchen, dining and living room measuring 43 ' x 15' with a wood-burning fireplace in living room. The three bedrooms are good sizes and the Master has an ensuite bathroom and there is an additional bathroom between bedrooms. One bedroom could be used as a bedroom or sitting room with sliding glass doors to cement patio. Unfinished basement has hookup for washer and dryer. Upstairs is unfinished but has room for more bedrooms or office space at approximately 800 square feet. You don't want to miss this opportunity to live on Mitchell Street!

$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

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

$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

$1,350,000Est. Payment
0 Acres
Overlook Drive, Hillsdale, NY 12529
Lots Land For Sale

Overlook Forest. One hundred and fifty beautifully wooded acres in eastern Hillsdale: the ideal setting for a private retreat or family compound. There are logging roads, trails and stone walls throughout the property with potential mountain views. The land is currently enrolled in a Forestry Exemption plan which reduces taxes and schedules periodic revenue-generating cuttings. The land is conveniently situated with easy access to everything the Hudson Valley and Berkshires have to offer.

$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.

$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.

$1,350,000Est. Payment
0 Acres
0 Overlook Drive, Hillsdale, NY 12529
Lots Land For Sale

Overlook Forest. One hundred and fifty beautifully wooded acres in eastern Hillsdale: the ideal setting for a private retreat or family compound. There are logging roads, trails and stone walls throughout the property with potential mountain views. The land is currently enrolled in a Forestry Exemption plan which reduces taxes and schedules periodic revenue-generating cuttings. The land is conveniently situated with easy access to everything the Hudson Valley and Berkshires have to offer.

$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!

$1,030,000Est. Payment
0 Acres
66 Fado Road, Copake, NY 12529
Lots Land For Sale

Build your world class home tucked amidst 127 acres of naturally pristine landscape punctuated by demure pastureland, ancient stone walls, natural wetlands, and extensive hardwood forest. This property offers a perfect mix of rolling hills, open fields, tranquil woodland and stunning views. In addition, the property features a classic farmhouse and hay barn that will need some renovating to bring back their original glory. Enjoy timeless uninterrupted views of the sun rising over the Berkshires and setting over the Catskills. No restrictions or easements, 20 minutes to Hudson or Great Barrington, and within ten minutes of Catamount, Copake Lake, Copake Country Club, Bash Bish Falls and the Hudson Valley Rail Trail. The possibilities are endless. Come live out your fantasy! The property consists of two parcels (145.-1-7 at 121 acres in the Town of Copake) and (145.-1-46 at 6 acres in the town of Hillsdale).

$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

$100,000Est. Payment
10 Acres
0 Route 71, Unknown Ny City, NY 12529
Lots Land For Sale

HILLSDALE, NY: Very attractive 10 Acre lot, approved for septic, that offers lots of possibilities! Lightly wooded, with many level areas for building. Bring offers! Please excuse "unknown city" it is a system error we are trying to fix.

$1,600,000Est. Payment
0 Acres
0 Knox La, Austerlitz, NY 12529
Lots Land For Sale

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 only, 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 home sites with gorgeous views, Much of the property is currently wooded offering privacy and excellent hunting opportunities. There is also a large pond on the property as well. One lot has an existing well in place. Don't miss out on this outstanding opportunity. Copake-Taconic Schools.

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