Hillsdale, NY Homes

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  $964,000

  • 3 Beds
  • 1.5 Baths
  • 1,293 Sq Ft

  44 SW Colony Rd, Hillsdale, NY 12529

  Set on the shores of Copake Lake, this charming waterfront home blends classic lake character with thoughtful modern updates. Offering three bedrooms and 1.5 baths, the home features a bright open kitchen, living, and dining area designed for easy lake living and entertaining. Recent renovations, including HVAC, septic system, and expansion to main floor, bring fresh style and comfort while

  Austin Urban Venture Fox Realty Group

  44 SW Colony Rd, Hillsdale, NY 12529
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  /22

  $13,000 Per Month

  • 4 Beds
  • 3 Baths
  • 3,164 Sq Ft
  • House for Rent

  85 Gellert Ln, Hillsdale, NY 12529

  Located 2.5 hours from NYC and Boston, this 4-bedroom, 3-bathroom Hillsdale summer rental offers a bright, contemporary interior with curated antiques on 8+ private acres featuring streams, a pond, and historic barns. The home includes a modern open kitchen with Caesarstone countertops and state-of-the-art appliances, which flows directly to a bluestone patio and stone terrace equipped with an

  Amy Longley William Pitt Sotheby's Int'l

  85 Gellert Ln, Hillsdale, NY 12529
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  /3

  $25,000 Sold May 28, 2025

  0 Stonehill Dr, Hillsdale, NY 12529

  • Land
  • 41,817 Sq Ft
  • $26,042 per Acre

  Last Sold Summary

  • 13 Days On Market

  Last Listing Agent David Birch Barns & Farms Realty, LLC

  0 Stonehill Dr, Hillsdale, NY 12529
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  /22

  Not Listed For Sale

  39 - stop 26 Justice Rd, Hillsdale, NY 12529

  • 2 Beds
  • 1 Bath
  • 1,896 Sq Ft
  • Built 1984

  39 - stop 26 Justice Rd, Hillsdale, NY 12529

  Last Sold Summary

  • $203/SF
  • 69 Days On Market

  • Last Sold Price $385,000
  • Sep 29, 2023

  Last Listing Agent Kelsey Winters Davala Real Estate, LLC
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  /28

  $1,275,000

  • 1 Bed
  • 2 Baths
  • 1,700 Sq Ft

  401 Collins St, Hillsdale, NY 12529

  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

  Pamela King-Belfor Four Seasons Sothebys Intl

  401 Collins St, Hillsdale, NY 12529
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  /10

  $1,850 Per Month

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Apartment for Rent

  3191 State Route 23 Unit 3, Hillsdale, NY 12529

  Well-maintained 2-bedroom, 1-bath apartment offering comfortable living with a functional layout. The unit features a bright living area, an updated kitchen with ample cabinetry, and two well-sized bedrooms with good natural light. The bathroom is clean and modern, with a full tub/shower. Enjoy easy access and sliding glass doors that open to a covered outdoor space—perfect for fresh air and

  Greg Berardi Berardi Realty

  3191 State Route 23 Unit 3, Hillsdale, NY 12529
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  /30

  $650,000 Sold Dec 22, 2025

  63 Cherokee Dr, Hillsdale, NY 12529

  • 3 Beds
  • 2.5 Baths
  • 2,256 Sq Ft
  • Built 1985

  Last Sold Summary

  • 2% Below List Price
  • $288/SF
  • 33 Days On Market

  Current Estimated Value $644,337

  Last Listing Agent Blanche Mackey Copake Lake Realty Corp.

  63 Cherokee Dr, Hillsdale, NY 12529
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  /7

  Not Listed For Sale

  0 - No# Justice Rd, Hillsdale, NY 12529

  0 - No# Justice Rd, Hillsdale, NY 12529

  Last Sold Summary

  • 71 Days On Market

  • Last Sold Price $32,500
  • Sep 27, 2024

  Last Listing Agent John Avenia Columbia County RE Specialist
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  /37

  $695,000 New Construction

  • 3 Beds
  • 3 Baths
  • 1,824 Sq Ft

  30 Ridge Ln, Hillsdale, NY 12529

  Offering privacy, quality construction, and an ideal location. Set in the heart of the Roe-Jan region of the Hudson Valley and at the edge of the Berkshires, this home is tucked privately among mature trees on nearly eight acres while remaining close to the center of town. Recently constructed by one of the region's top builders, the residence was designed with both quality and longevity in mind.

  John Barbato Compass, Hillsdale

  30 Ridge Ln, Hillsdale, NY 12529
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  /13

  $2,500 Per Month

  • 2 Beds
  • 1 Bath
  • 832 Sq Ft
  • House for Rent

  9 Washington Dr Unit 17, Hillsdale, NY 12529

  9 Washington Drive, Copake Lake. Partially Furnished Cottage for rent. Offered both seasonally for 3,000/month or yearly for 2,500/month. Beautiful views of the lake from almost every room due to the OPEN FLOOR plan. The lake is literally steps away. (3rd house in on Washington Drive) 2 Bedrooms, galley kitchen, efficient gas heating, large deck overlooking the lake. Great yard for having summer

  Margaret Bower Avenia Columbia County RE Specialist

  9 Washington Dr Unit 17, Hillsdale, NY 12529
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  /18

  $500,000 Sold Jan 23, 2026

  2253 County Route 21, Hillsdale, NY 12529

  • 2 Beds
  • 2 Baths
  • 1,493 Sq Ft
  • Built 2021

  Last Sold Summary

  • 7% Below List Price
  • $335/SF
  • 124 Days On Market

  Last Listing Agent Jeffries Blackerby Houlihan Lawrence Inc.

  2253 County Route 21, Hillsdale, NY 12529
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  /10

  Not Listed For Sale

  199 Rt 217, Ghent, NY 12075

  • 2 Beds
  • 1 Bath
  • 960 Sq Ft
  • Built 1925

  199 Rt 217, Ghent, NY 12075

  Last Sold Summary

  • $292/SF
  • 99 Days On Market

  • Last Sold Price $280,000
  • Mar 21, 2025

  Last Listing Agent Kylah Campeta LYF Homes
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  /16

  $689,000

  • 3 Beds
  • 2.5 Baths
  • 2,256 Sq Ft

  621 County Route 21, Hillsdale, NY 12529

  This updated contemporary home in Hillsdale offers a perfect blend of comfort and style on 10 private acres. The interior features a mix of hardwood, carpet, and nearly new vinyl flooring complemented by fresh paint and trim throughout. The kitchen comes fully equipped with a refrigerator, microwave, and stove. Enjoy a semi-finished basement. Key updates include new electric and plumbing, an

  Derek Greene The Greene Realty Group

  621 County Route 21, Hillsdale, NY 12529
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  /13

  $1,850 Per Month

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Apartment for Rent

  3191 New York 23 Unit 3, Hillsdale, NY 12529

  Well-maintained 2-bedroom, 1-bath apartment offering comfortable living with a functional layout. The unit features a bright living area, an updated kitchen with ample cabinetry, and two well-sized bedrooms with good natural light. The bathroom is clean and modern, with a full tub/shower. Enjoy easy access and sliding glass doors that open to a covered outdoor space—perfect for fresh air and

  Greg Berardi Berardi Realty

  3191 New York 23 Unit 3, Hillsdale, NY 12529
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  /42

  $1,350,000 Sold Jun 27, 2025

  864 W End Rd, Hillsdale, NY 12529

  • 4 Beds
  • 3.5 Baths
  • 3,540 Sq Ft
  • Built 2003

  Last Sold Summary

  • 4% Above List Price
  • $381/SF
  • 15 Days On Market

  Current Estimated Value $1,378,168

  Last Listing Agent John Barbato Compass, Hillsdale

  864 W End Rd, Hillsdale, NY 12529
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  /27

  Not Listed For Sale

  3002 State Route 23 --, Hillsdale, NY 12529

  • 3 Beds
  • 1 Bath
  • 1,296 Sq Ft
  • Built 1975

  3002 State Route 23 --, Hillsdale, NY 12529

  Last Sold Summary

  • $304/SF
  • 59 Days On Market

  • Last Sold Price $393,500
  • Apr 15, 2025

  Last Listing Agent Paige Backhaus WILLIAM RAVEIS - BERKSHIRE
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  $785,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,500 Sq Ft

  9254 New York 22, Hillsdale, NY 12529

  Hillsdale 2500 SF 4BR residence with large deck, inground pool and 60x100 garage on 2.9 acs. Currently Auto Repair Business near Junction of Routes 22 & 23. Incredible opportunity to continue Auto Repair and towing business or convert 60x100 Garage into Storage Facility or other use. House would make great rental property.

  David Birch Barns & Farms Realty

  9254 New York 22, Hillsdale, NY 12529
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  /14

  $1,800 Per Month

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Apartment for Rent

  3191 New York 23 Unit 1, Hillsdale, NY 12529

  Well-maintained 2-bedroom, 1-bath ground-floor apartment (with limited steps) offering comfortable living with a functional layout. The unit features a bright living area, an updated kitchen with ample cabinetry, and two well-sized bedrooms with good natural light. The bathroom is clean and modern, with a full tub/shower. Enjoy easy access with ground-level entry and sliding glass doors that open

  Greg Berardi Berardi Realty

  3191 New York 23 Unit 1, Hillsdale, NY 12529
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  /20

  $605,000 Sold Sep 17, 2025

  15 Roosevelt Dr, Hillsdale, NY 12529

  • 1,080 Sq Ft
  • Built 1958

  Last Sold Summary

  • 34% Below List Price
  • $560/SF
  • 742 Days On Market

  Current Estimated Value $569,441

  Last Listing Agent Donna Peck Past Member

  15 Roosevelt Dr, Hillsdale, NY 12529
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  /19

  Est $205,000 Not Listed For Sale

  22 Anthony St, Hillsdale, NY 12529

  • 5 Beds
  • 5 Baths
  • 2,502 Sq Ft
  • Built 1888

  22 Anthony St, Hillsdale, NY 12529

  Last Sold Summary

  • 7% Above List Price
  • $76/SF
  • 83 Days On Market

  • Last Sold Price $191,000
  • Feb 12, 2025

  Last Listing Agent Margaret Bower Avenia Columbia County RE Specialist
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  /25

  $770,000 New Construction

  • 3 Beds
  • 3 Baths
  • 1,800 Sq Ft

  801 Rodman Rd, Hillsdale, NY 12529

  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 house to be built? This brand-new construction is being sold as it stands today, as a blank unfinished canvas 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

  Michael Castellano Gilcrest Properties

  801 Rodman Rd, Hillsdale, NY 12529
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  /30

  $5,000 Per Month

  • 4 Beds
  • 3 Baths
  • 2,349 Sq Ft
  • House for Rent

  125 Taconic Creek Rd, Hillsdale, NY 12529

  Experience the quintessential Hudson Valley retreat in this private, 4-bedroom, 3-bathroom country home. Located just minutes from the slopes of Catamount Mountain Resort, this residence offers a seamless blend of rustic charm and modern convenience. The interior features a well-appointed kitchen and a living area anchored by a cozy wood stove--all complemented by tasteful, high-quality

  Rochelle Bartolo Beach & Bartolo Realtors

  125 Taconic Creek Rd, Hillsdale, NY 12529
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  /20

  $295,000 Sold Dec 30, 2025

  376 Approx Whippoorwill Rd, Hillsdale, NY 12529

  • Land
  • 12 Acres
  • $24,583 per Acre

  Last Sold Summary

  • 39 Days On Market

  Last Listing Agent John Avenia Columbia County RE Specialist

  376 Approx Whippoorwill Rd, Hillsdale, NY 12529
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  Not Listed For Sale

  105 Seekonk Rd, Hillsdale, NY 12529

  • 1 Bed
  • 1 Bath
  • 1,134 Sq Ft
  • Built 1984

  105 Seekonk Rd, Hillsdale, NY 12529

  Last Sold Summary

  • $306/SF

  • Last Sold Price $347,000

  Last Listing Agent Paige Paluch WILLIAM RAVEIS - BERKSHIRE
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  /34

  $719,000

  • 4 Beds
  • 3 Baths
  • 1,475 Sq Ft

  81 Black Grocery Rd, Hillsdale, NY 12529

  On a quiet country road, sit's the prettiest sunshine yellow house you've ever seen.Welcome to a property where outdoor splendor and indoor comfort merge seamlessly, where everything has been taken care of, and all you need to do is arrive and exhale. Rolling hills and open farmland stretch out before you, and they're all yours to enjoy.Inside, the dining room flows into an open kitchen

  Shaina Marron Houlihan Lawrence Inc.

  81 Black Grocery Rd, Hillsdale, NY 12529
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  /44

  $725,000 Sold Dec 09, 2025

  15 Tory Hill Rd, Hillsdale, NY 12529

  • 3 Beds
  • 2 Baths
  • 2,592 Sq Ft
  • Built 2007

  Last Sold Summary

  • $280/SF
  • 45 Days On Market

  Current Estimated Value $749,431

  Last Listing Agent John Avenia Columbia County RE Specialist

  15 Tory Hill Rd, Hillsdale, NY 12529
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  Est $1,067,505 Not Listed For Sale

  27 Maple St, Hillsdale, NY 12529

  • 4 Beds
  • 2.5 Baths
  • 2,538 Sq Ft
  • Built 1841

  27 Maple St, Hillsdale, NY 12529

  Last Sold Summary

  • 13% Below List Price
  • $483/SF
  • 122 Days On Market

  • Last Sold Price $1,225,000
  • Sep 17, 2024

  Last Listing Agent Austin Urban Venture Fox Realty Group
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  /28

  $810,000

  • 6 Beds
  • 2 Baths
  • 2,998 Sq Ft

  60 Anthony St, Hillsdale, NY 12529

  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

  Gerard Meenagh The Meenagh Group Realty

  60 Anthony St, Hillsdale, NY 12529
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  /57

  $1,168,500 Sold Jul 11, 2025

  523 Breezy Hill Rd, Hillsdale, NY 12529

  • 3 Beds
  • 2.5 Baths
  • 1,931 Sq Ft
  • Built 1973

  Last Sold Summary

  • 2% Below List Price
  • $605/SF
  • 44 Days On Market

  Current Estimated Value $1,187,592

  Last Listing Agent Claudia Crane COMPASS MASSACHUSETTS , LLC GB

  523 Breezy Hill Rd, Hillsdale, NY 12529
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  /2

  Est $1,573,219 Not Listed For Sale

  172 W End Rd, Hillsdale, NY 12529

  • 3 Beds
  • 3 Baths
  • 3,263 Sq Ft
  • Built 1900

  172 W End Rd, Hillsdale, NY 12529

  Last Sold Summary

  • 10% Below List Price
  • $437/SF

  • Last Sold Price $1,425,000

  Last Listing Agent Lance Vermeulen LANCE VERMEULEN RE, INC
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  /44

  $1,275,000

  • 4 Beds
  • 3 Baths
  • 3,282 Sq Ft

  9960 New York 22, Hillsdale, NY 12529

  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

  Pamela King-Belfor Four Seasons Sotheby's Int.

  9960 New York 22, Hillsdale, NY 12529
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  /29

  $965,000 Sold Dec 22, 2025

  271 Texas Hill Rd, Hillsdale, NY 12529

  • 3 Beds
  • 2 Baths
  • 2,279 Sq Ft
  • Built 1930

  Last Sold Summary

  • $423/SF
  • 21 Days On Market

  Current Estimated Value $1,011,081

  Last Listing Agent Kelcey Otten Compass Greater NY, LLC d/b/a

  271 Texas Hill Rd, Hillsdale, NY 12529
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  /11

  Est $482,380 Not Listed For Sale

  40 Marsten Ln, Hillsdale, NY 12529

  • 4 Beds
  • 2 Baths
  • 1,900 Sq Ft
  • Built 1976

  40 Marsten Ln, Hillsdale, NY 12529

  Last Sold Summary

  • 47% Above List Price
  • $173/SF
  • 28 Days On Market

  • Last Sold Price $329,000
  • Sep 19, 2023

  Last Listing Agent Peter Darrell Tri Hudson Realty, LLC
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  /50

  $1,695,000 Pending

  • 4 Beds
  • 3 Baths
  • 2,608 Sq Ft

  46 Collins St, Hillsdale, NY 12529

  Welcome to Nobletown Farmhouse, a circa 1850 home on 2+ peaceful acres in prime Hillsdale, on one of Columbia County's prettiest country roads. This beautifully updated four-bedroom, three-bath antique farmhouse showcases the elegant proportions and craftsmanship of mid-19th century architecture, with designer finishes, modern systems, and a full complement of additional structures that make it a

  Anthony D'Argenzio Houlihan Lawrence, Inc

  46 Collins St, Hillsdale, NY 12529
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  /4

  $81,000 Sold Jan 27, 2026

  0 Rodman Rd, Hillsdale, NY 12529

  • Land
  • 4.4 Acres
  • $18,409 per Acre

  Last Sold Summary

  • 2% Above List Price
  • 14 Days On Market

  Last Listing Agent Theresa Westlake Copake Lake Realty Corp.

  0 Rodman Rd, Hillsdale, NY 12529
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  /2

  Est $853,234 Not Listed For Sale

  137 Whippoorwill Rd, Hillsdale, NY 12529

  • 4 Beds
  • 3 Baths
  • 2,322 Sq Ft
  • Built 1910

  137 Whippoorwill Rd, Hillsdale, NY 12529

  Last Sold Summary

  • 15% Below List Price
  • $319/SF

  • Last Sold Price $740,000

  Last Listing Agent marylou Kersten COPAKE LAKE REALTY CORP.
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  /17

  $999,000

  • 4 Beds
  • 2.5 Baths
  • 1,344 Sq Ft

  25 Nobletown Rd, Hillsdale, NY 12529

  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

  Andrew Gates HOULIHAN LAWRENCE, INC

  25 Nobletown Rd, Hillsdale, NY 12529
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  /4

  $199,999 Sold Dec 31, 2025

  2605 New York 23, Hillsdale, NY 12529

  • 5 Beds
  • 3 Baths
  • 2,578 Sq Ft
  • Built 1890

  Last Sold Summary

  • $78/SF
  • 40 Days On Market

  Last Listing Agent Lindsay Lebrecht Copake Lake Realty Corp.

  2605 New York 23, Hillsdale, NY 12529
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  /25

  Est $738,711 Not Listed For Sale

  274 Texas Hill Rd, Hillsdale, NY 12529

  • 3 Beds
  • 2.5 Baths
  • 2,272 Sq Ft
  • Built 2002

  274 Texas Hill Rd, Hillsdale, NY 12529

  Last Sold Summary

  • 9% Above List Price
  • $299/SF
  • 41 Days On Market

  • Last Sold Price $680,000
  • Aug 27, 2024

  Last Listing Agent Lori Mendelis Past Member
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  /14

  $150,000 Under Contract

  • 4 Beds
  • 1 Bath
  • 2,116 Sq Ft

  10021 New York 22, Hillsdale, NY 12529

  Step back in time and imagine the possibilities with this charming 1800s farmhouse, situated on a picturesque 1-acre lot complete with a pond and stream. Nestled in a desirable area, this property offers a rare opportunity to restore and customize a true piece of history. The home features solid construction and ''great bones,'' providing a strong foundation for a full renovation. A spacious

  Paul Crayton Coldwell Banker Advisor Realty

  10021 New York 22, Hillsdale, NY 12529

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