Hillsdale, NY Homes

• 

  

  

  /19

  $325,000

  • 2 Beds
  • 1 Bath
  • 736 Sq Ft

  81 SW Colony Rd, Hillsdale, NY 12529

  Welcome to THE UPSTATE RETREAT--where every day feels like a vacation on Copake Lake, the largest lake in Columbia County, spanning approximately 425 acres. Whether you're searching for the perfect weekend escape, a summer lake house, or a year-round getaway, this charming 2-bedroom, 1-bath bungalow offers the quintessential upstate lifestyle just over two hours from New York City. Beyond the

  

  Mark Saxby

  Berkshire Hathaway HomeService

  81 SW Colony Rd, Hillsdale, NY 12529
• 

  

  

  /18

  $8,000 Per Month

  • 3 Beds
  • 3 Baths
  • 1,885 Sq Ft
  • House for Rent

  70 SW Colony Rd, Hillsdale, NY 12529

  Set directly on the shores of Copake Lake, this character-filled lake house offers a rare opportunity to experience one of the Hudson Valley's most beloved waterfront communities through every season. Originally conceived as a weekend escape, the house combines the easygoing spirit of a classic lake cottage with a wonderfully considered mix of rustic, Scandinavian and mid-century

  Annabel Taylor Four Seasons Sotheby's Int.

  70 SW Colony Rd, Hillsdale, NY 12529
• 

  

  

  /14

  $104,000

  Sold May 27, 2026

  10021 New York 22, Hillsdale, NY 12529

  • 4 Beds
  • 1 Bath
  • 2,116 Sq Ft
  • Built 1856

  Last Sold Summary

  • 31% Below List Price
  • $49/SF
  • 91 Days On Market

  Last Listing Agent Paul Crayton Coldwell Banker Advisor Realty

  10021 New York 22, Hillsdale, NY 12529
• 

  Not Listed For Sale

  515 Turnpike, Hillsdale, NY 12529

  • 3 Beds
  • 2 Baths
  • 2,134 Sq Ft
  • Built 1983

  515 Turnpike, Hillsdale, NY 12529

  Last Sold Summary

  • 50 Days On Market

  Last Listing Agent Joseph Briggs William Pitt Sothebys Int Rlty
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  /36

  $650,000

  Under Contract

  • 3 Beds
  • 2.5 Baths
  • 1,977 Sq Ft

  3493 County Route 7, Hillsdale, NY 12529

  Escape to your own private retreat where lake living, outdoor adventure, and timeless country charm come together!Just steps from scenic Copake Lake, this property offers access to one of Columbia County's premier recreational destinations. The 410-acre, motorboat-friendly lake is perfect for boating, waterskiing, kayaking, paddleboarding, and excellent fishing, while nearby Copake

  

  Sabrina Puppolo

  Corcoran Country Living

  3493 County Route 7, Hillsdale, NY 12529
• 

  

  /24

  $1,850 Per Month

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

  3191 State Route 23 Unit 2, Hillsdale, NY 12529

  MULTIPLE APARTMENTS FOR RENTYour new digs? A.K.A, 3191 Route 23, Hilldale NY, one mile from Catamont on the Massachusetts border. Beautiful, updated two-bedroom, one bath apartments with pretty views and a balcony to enjoy them!! 1,850/mo. plus utilities. Laundry facility on property. Must have good credit and references. Pets allowed with additional funds. Additional units available, please

  Margaret Bower Avenia Columbia County RE Specialist

  3191 State Route 23 Unit 2, Hillsdale, NY 12529
• 

  

  /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 $663,088

  Last Listing Agent Blanche Mackey Copake Lake Realty Corp.

  63 Cherokee Dr, Hillsdale, NY 12529
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  /68

  Est $2,924,319

  Not Listed For Sale

  149 Tory Hill Farm Rd, Hillsdale, NY 12529

  • 4 Beds
  • 2.5 Baths
  • 3,604 Sq Ft
  • Built 1986

  149 Tory Hill Farm Rd, Hillsdale, NY 12529

  Last Sold Summary

  • 39 Days On Market

  Last Listing Agent John Barbato Compass, Hillsdale
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  /5

  $225,000

  • Land
  • 6 Acres
  • $37,500 per Acre

  L135.2 Rockledge Rd, Hillsdale, NY 12529

  Escape to your own private sanctuary in the heart of Columbia County's coveted Hudson Valley. This 6 acre wooded parcel on scenic Rockledge Road offers the perfect canvas for your dream retreat, with mature trees providing natural privacy and a peaceful, secluded setting that feels worlds away from the everyday. Ideally situated in the Town of Hillsdale -- one of the region's most sought-after

  

  Jamie Mazuryk

  Venture Fox Realty Group LLC

  L135.2 Rockledge Rd, Hillsdale, NY 12529
• 

  

  /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
• 

  

  /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
• 

  

  /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

  • 69 Days On Market

  Last Listing Agent Kelsey Winters Davala Real Estate, LLC
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  /42

  $900,000

  $200K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,495 Sq Ft

  309 Pine Ridge Ln, Hillsdale, NY 12529

  Nestled on a wooded hillside on one of Hillsdale's prettiest country roads is where you will discover this exceptional 2,500 sq.ft. custom-built home. The 5.5-acre parcel sits above Pine Ridge Lane; a lightly travelled country road located just off Mitchell Street in the heart of Hillsdale. Surrounded by nature in every direction, the peaceful, park-like setting is unique and as beautiful as any

  Margaret Bower Avenia Columbia County RE Specialist

  309 Pine Ridge Ln, Hillsdale, NY 12529
• 

  

  /13

  $2,300 Per Month

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

  16 Longley Dr, Hillsdale, NY 12529

  Welcome to Four Seasons at Copake Lake, where country charm meets lake living. This partially furnished two-bedroom home features an updated kitchen and bathroom, along with beautiful wood floors throughout. Cozy and inviting in every season, the home offers a wood stove for warmth on chilly evenings and an outdoor fire pit perfect for gathering with family and friends under the stars. Enjoy

  Lindsay Lebrecht Copake Lake Realty Corp.

  16 Longley Dr, Hillsdale, NY 12529
• 

  

  /9

  $675,000

  Sold Jun 09, 2026

  3244 Cr 7, Hillsdale, NY 12529

  • Land
  • 56.9 Acres
  • $11,863 per Acre

  Last Sold Summary

  • 20% Below List Price
  • 809 Days On Market

  Last Listing Agent Theresa Westlake Copake Lake Realty Corp.

  3244 Cr 7, 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 Listing Agent John Avenia Columbia County RE Specialist
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  /6

  $175,000

  $120K PRICE DROP

  • Land
  • 33.31 Acres
  • $5,254 per Acre

  50 Dugway Rd, Hillsdale, NY 12529

  Escape to 33.31 acres of untouched beauty in Columbia County, NY. This stunning parcel of wooded land offers complete privacy with no neighbors in sight, just you and the tranquility of nature. Imagine the possibilities as you explore the lush, wooded landscape teeming with wildlife. This parcel features a dynamic topography of hills that reach an elevation of over 1,000 feet. With this parcel,

  Jeffrey McKinney Beach & Bartolo Realtors

  50 Dugway Rd, Hillsdale, NY 12529
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  /30

  $4,000 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
• 

  

  /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 $642,748

  Last Listing Agent Donna Peck Past Member

  15 Roosevelt Dr, 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

  • 99 Days On Market

  Last Listing Agent Kylah Campeta-Perez LYF Homes
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  /33

  $389,000

  • 4 Beds
  • 1 Bath
  • 2,229 Sq Ft

  1953 County Road 11, Claverack, NY 12513

  Step into a home that feels like it has been quietly telling its story since the 1800's, where every beam and board carries the charm of a bygone era. This classic colonial residence preserves its original character with exposed beams stretching across the main floor and a layout that balances simplicity with purpose. The kitchen is modest yet functional, anchored by a traditional wood store that

  Karen Davala Davala Real Estate, LLC

  1953 County Road 11, Claverack, NY 12513
• 

  

  /5

  $1,600 Per Month

  • 1 Bed
  • 1 Bath
  • 773 Sq Ft
  • Apartment for Rent

  32 Anthony St Unit 3B, Hillsdale, NY 12529

  Interested parties in this listing please contact Gerard Meenagh the listing agent

  Gerard Meenagh The Meenagh Group Realty

  32 Anthony St Unit 3B, Hillsdale, NY 12529
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  /77

  $1,625,000

  Sold May 18, 2026

  46 Collins St, Hillsdale, NY 12529

  • 4 Beds
  • 3 Baths
  • 2,608 Sq Ft
  • Built 1850

  Last Sold Summary

  • 4% Below List Price
  • $623/SF
  • 62 Days On Market

  Current Estimated Value $1,579,708

  Last Listing Agent Anthony D'Argenzio Houlihan Lawrence Inc.

  46 Collins St, Hillsdale, NY 12529
• 

  

  /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

  • 59 Days On Market

  Last Listing Agent Paige Backhaus WILLIAM RAVEIS - BERKSHIRE
• 

  

  /13

  $325,000

  • Land
  • 24.4 Acres
  • $13,320 per Acre

  120 Dugway Rd, Hillsdale, NY 12529

  If the home you dream of building includes a private setting, on a hill that's surrounded by nature, and valuable infrastructure already in place, then this is the land for you. The lot is 24.40 acres of beautiful, mostly wooded land with a cleared one-acre meadow BUILD SITE that is located high on the hill and far from the road. There's a roughed-in DRIVEWAY that starts at the road with a bridge

  Jeffrey McKinney Beach & Bartolo Realtors

  120 Dugway Rd, Hillsdale, NY 12529
• 

  $3,700,000

  Sold Jul 17, 2026

  54 Far View Ln, Hillsdale, NY 12529

  • 4 Beds
  • 3 Baths
  • 3,666 Sq Ft
  • Built 1971

  Last Sold Summary

  • 7% Below List Price
  • $1,009/SF
  • 20 Days On Market

  Current Estimated Value $3,926,762

  Last Listing Agent Anthony D'Argenzio Houlihan Lawrence, Inc

  54 Far View Ln, Hillsdale, NY 12529
• 

  

  /19

  Est $272,503

  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

  • 83 Days On Market

  Last Listing Agent Margaret Bower Avenia Columbia County RE Specialist
• 

  

  /23

  $305,000

  $15K PRICE INCREASE Pending

  • 2 Beds
  • 1 Bath
  • 925 Sq Ft

  9377 New York 22, Hillsdale, NY 12529

  WELCOME HOME to this charming and stylishly updated retreat situated on a spacious, level lot in beautiful Hillsdale, NY! Offering a perfect blend of modern character and country appeal, this home is ideal for those looking for a peaceful getaway with fantastic outdoor space. As you arrive, the striking dark grey exterior, crisp white accents, and charming fenced-in front yard lead you to a

  Ronald Green KW Mid-Hudson

  9377 New York 22, Hillsdale, NY 12529
• 

  

  /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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  /2

  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
• 

  

  /31

  $1,695,000

  Pending

  • Land
  • 127.1 Acres
  • $13,336 per Acre

  0 Mitchell St Unit 20262545, Hillsdale, NY 12529

  Mitchell St is one of the most picturesque roads in Hillsdale and this property has a beautiful gentleness to it. Comprising of three separate contiguous lots (35.2 acres, 43.1 acres and 48.8 acres per assessor); access comes in off the southern most lot (43.10) and meanders through the property by a pond site, open meadows, old fruit trees and views of the hills around. The middle lot takes you

  Jennifer Harvey Compass Greater NY LLC

  0 Mitchell St Unit 20262545, 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 $766,107

  Last Listing Agent John Avenia Columbia County RE Specialist

  15 Tory Hill Rd, Hillsdale, NY 12529
• 

  

  /18

  Est $350,005

  Not Listed For Sale

  118 Yonderview Rd, Hillsdale, NY 12529

  • 3 Beds
  • 1.5 Baths
  • 1,536 Sq Ft
  • Built 1963

  118 Yonderview Rd, Hillsdale, NY 12529

  Last Sold Summary

  • 58 Days On Market

  Last Listing Agent Lindsay Lebrecht Copake Lake Realty Corp.
• 

  

  /50

  $949,900

  $50K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  2955 State Route 23, Hillsdale, NY 12529

  Steeped in Hillsdale’s rich history, this extraordinary property began its life as one of the area’s original grist mills, situated in the area of Hillsdale once known as Murray’s Corner. Thoughtfully transformed over the years into a distinctive residence, it seamlessly blends historic character with the tranquility of a private country retreat. Set on 8.7 enchanting acres, the property feels as

  Jason Walch Coldwell Banker Advisor Realty

  2955 State Route 23, Hillsdale, NY 12529
• 

  

  /45

  $1,150,000

  Sold Jul 31, 2026

  1 van Bueran Dr, Hillsdale, NY 12529

  • 5 Beds
  • 3 Baths
  • 1,708 Sq Ft
  • Built 1988

  Last Sold Summary

  • $673/SF
  • 40 Days On Market

  Current Estimated Value $1,126,613

  Last Listing Agent Jessica Scott Compass Greater NY LLC

  1 van Bueran Dr, Hillsdale, NY 12529
• 

  

  /41

  Est $1,117,011

  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

  • 122 Days On Market

  Last Listing Agent Austin Urban Venture Fox Realty Group
• 

  

  /40

  $859,000

  $120K PRICE DROP

  • 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
• 

  

  /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 $966,958

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

  271 Texas Hill Rd, Hillsdale, NY 12529
• 

  /2

  Est $1,653,174

  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
• 

  

  /24

  $575,000

  $40K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 864 Sq Ft

  5 Adams Dr, Hillsdale, NY 12529

  This charming 3 BR, 1.5 Bath cottage is located across the street from Copake Lake and the HOA Waterfront, Marina and Beach area. Unlike some of the other homes in the area, the house is situated on an elevated, oversized lot with a big front yard and spectacular sunset views. Inside, the house features real wood paneling and a wood burning stove in the living room, a cozy kitchen with a new gas

  Russ Stein Compass Greater NY LLC

  5 Adams Dr, Hillsdale, NY 12529

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