Woodstock, NY Homes

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  /21

  $595,000

  Open Sun 3PM - 4PM

  • 2 Beds
  • 1 Bath
  • 1,338 Sq Ft

  357 Chestnut Hill Rd, Woodstock, NY 12498

  A STORYBOOK WOODSTOCK RETREAT IN THE WOODSSome homes provide shelter; others provide sanctuary. 357 Chestnut Hill Road is a sanctuary in the woods--a soulful Woodstock retreat where sunlight spills through skylights, pine glows underfoot, and the forest seems to lean in and whisper, ''stay awhile.''Set on 1.6 wooded acres with approximately 257 feet of road frontage, this

  Jacob Miles Brown Harris Stevens Hudson

  357 Chestnut Hill Rd, Woodstock, NY 12498
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  /28

  $999,000

  Sold Jan 23, 2026

  99 Cannon Cir, Woodstock, NY 12498

  • 3 Beds
  • 2 Baths
  • 1,948 Sq Ft
  • Built 2020

  Last Sold Summary

  • 18% Below List Price
  • $513/SF
  • 203 Days On Market

  Current Estimated Value $1,031,441

  Last Listing Agent Laurie Ylvisaker Coldwell Banker Village Green

  99 Cannon Cir, Woodstock, NY 12498
• 

  

  

  /19

  Est $441,343

  Not Listed For Sale

  777 Zena Rd, Woodstock, NY 12498

  • 3 Beds
  • 1.5 Baths
  • 1,305 Sq Ft
  • Built 1955

  777 Zena Rd, Woodstock, NY 12498

  Last Sold Summary

  • 108 Days On Market

  Last Listing Agent Mark Kanter BHHS HUDSON VALLEY PROP-WDST
• 

  

  

  /31

  $799,000

  Pending

  • 4 Beds
  • 3 Baths
  • 2,480 Sq Ft

  5 Lazy Brook Ln, Woodstock, NY 12498

  NEW NEW NEW! If you thought you have seen 5 Lazy Brook Lane, think again! This home is owned by a renowned architect and he has done a complete redesign! Mood, space, and finishes combine to create the ideal modern ranch. Coming to this 4 bedroom 3 bath home, you will first notice the new facade with white washed pine and a huge plate glass window where the unsightly bay window used to be. Now

  Richard Stoll Halter Associates Realty

  5 Lazy Brook Ln, Woodstock, NY 12498
• 

  $699,000

  Sold Mar 23, 2026

  19 Livingston Ct, Woodstock, NY 12498

  • 4 Beds
  • 2.5 Baths
  • 2,471 Sq Ft
  • Built 1973

  Last Sold Summary

  • 12% Below List Price
  • $283/SF
  • 167 Days On Market

  Current Estimated Value $737,243

  Last Listing Agent Timothy Ayers Berardi Realty

  19 Livingston Ct, Woodstock, NY 12498
• 

  

  /35

  Est $592,008

  Not Listed For Sale

  4 Lazy Brook Ln, Woodstock, NY 12498

  • 2 Beds
  • 2 Baths
  • 2,257 Sq Ft
  • Built 1956

  4 Lazy Brook Ln, Woodstock, NY 12498

  Last Sold Summary

  • 138 Days On Market

  Last Listing Agent Laura Wagner Past Member
• 

  

  /50

  $2,375,000

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

  235 California Quarry Rd, Woodstock, NY 12498

  Architect-Designed Modern Retreat with Unparalleled Views Over Woodstock! Perched high above the Town of Woodstock, this rare and exceptional home offers a front-row seat to breathtaking panoramic views that stretch from the mountains to the Ashokan Reservoir. Designed by noted architect Les Walker, this contemporary residence evokes the magic of living in a luxurious treehouse—where every room

  Ellen Osgood Coldwell Banker Village Green

  235 California Quarry Rd, Woodstock, NY 12498
• 

  $840,000

  Sold Oct 20, 2025

  48 Cooper Hollow Ln, Bearsville, NY 12409

  • 4 Beds
  • 3 Baths
  • 2,125 Sq Ft
  • Built 1973

  Last Sold Summary

  • 11% Below List Price
  • $395/SF
  • 77 Days On Market

  Current Estimated Value $1,051,011

  Last Listing Agent Eric Amaral Coldwell Banker Village Green

  48 Cooper Hollow Ln, Bearsville, NY 12409
• 

  

  /17

  Est $516,637

  Not Listed For Sale

  16 Delisio Ln, Woodstock, NY 12498

  • 2 Beds
  • 1 Bath
  • 1,181 Sq Ft
  • Built 1951

  16 Delisio Ln, Woodstock, NY 12498

  Last Sold Summary

  • 32 Days On Market

  Last Listing Agent Mark Kanter BHHS HUDSON VALLEY PROP-WDST
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  /50

  $999,900

  $75K PRICE INCREASE Under Contract

  • 3 Beds
  • 3 Baths
  • 1,749 Sq Ft

  15 Upper West Ohayo Mountain Rd, Bearsville, NY 12409

  Tucked away on a quiet private road in coveted Bearsville, this light-filled contemporary sanctuary offers 1.87 serene acres and the ultimate Hudson Valley indoor-outdoor lifestyle. Perfectly positioned to capture sweeping mountain vistas, the home delivers an effortless blend of mid-century character and modern luxury. Step inside to an expansive main living area anchored by a whitewashed brick

  Stefan Sanzi Hudson Valley Real Estate Brok

  15 Upper West Ohayo Mountain Rd, Bearsville, NY 12409
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  /34

  $655,700

  Sold Jun 23, 2026

  203 Reynolds Rd, Woodstock, NY 12498

  • 2 Beds
  • 2 Baths
  • 1,322 Sq Ft
  • Built 1930

  Last Sold Summary

  • 4% Above List Price
  • $496/SF
  • 22 Days On Market

  Current Estimated Value $642,890

  Last Listing Agent Laurie Ylvisaker Coldwell Banker Village Green

  203 Reynolds Rd, Woodstock, NY 12498
• 

  

  /35

  Est $722,195

  Not Listed For Sale

  78 Ratterman Rd, Woodstock, NY 12498

  • 3 Beds
  • 2 Baths
  • 1,548 Sq Ft
  • Built 1955

  78 Ratterman Rd, Woodstock, NY 12498

  Last Sold Summary

  • 36 Days On Market

  Last Listing Agent Leslie Foti Coldwell Banker Village Green
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  /50

  $1,795,000

  Open Sat 11AM - 1PM

  • 5 Beds
  • 7 Baths
  • 10,275 Sq Ft

  34 Elwyn Ln, Wood Stock, NY 12498

  Where history meets reinvention in Woodstock. From 19th-century barn to 21st-century landmark, come explore one of Woodstock's most extraordinary buildings. With part of the building dating to 1865, this extraordinary 10,000+ square foot barn conversion has been renovated to a high-end standard and is unlike any other structure in Woodstock, and quite possibly unlike any other building in the

  Michelle Bergkamp William Pitt Sotheby's Interna

  34 Elwyn Ln, Wood Stock, NY 12498
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  /44

  $950,000

  Sold Aug 07, 2026

  9 Chesters Place, Woodstock, NY 12498

  • 3 Beds
  • 2 Baths
  • 1,912 Sq Ft
  • Built 2017

  Last Sold Summary

  • $497/SF
  • 48 Days On Market

  Current Estimated Value $933,740

  Last Listing Agent Amy Lonas Coldwell Banker Village Green

  9 Chesters Place, Woodstock, NY 12498
• 

  

  /43

  Est $1,307,860

  Not Listed For Sale

  13 Snow Ridge, Woodstock, NY 12498

  • 4 Beds
  • 3.5 Baths
  • 3,379 Sq Ft
  • Built 1890

  13 Snow Ridge, Woodstock, NY 12498

  Last Sold Summary

  • 21 Days On Market

  Last Listing Agent Marilyn Heir BHHS HUDSON VALLEY PROP-WDST
• 

  

  /40

  $579,000

  Open Sun 11AM - 1PM

  • 3 Beds
  • 1.5 Baths
  • 1,480 Sq Ft

  28 Ballantine Ln, Bearsville, NY 12409

  One of Woodstock's Original Handmade homes tucked away on almost 3 private acres at the end of a dead end lane. This 3 Bd/ 1.5 Ba home minutes to the center of Woodstock is the quintessential country retreat. Blending in with the natural Hudson Valley landscape this cedar and bluestone sided home leans into Woodstocks rich history of artists and builders utilizing their surroundings for sourcing

  Johanna Trimboli Halter Associates Realty

  28 Ballantine Ln, Bearsville, NY 12409
• 

  

  /10

  $20,000

  Sold Jul 03, 2026

  Tbd New York 212, Woodstock, NY 12409

  • Land
  • 32,670 Sq Ft
  • $26,667 per Acre

  Last Sold Summary

  • 33% Below List Price
  • 63 Days On Market

  Last Listing Agent Ronin Ingwersen Serhant LLC

  Tbd New York 212, Woodstock, NY 12409
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  /50

  Est $676,436

  Not Listed For Sale

  64 Country Club Ln, Woodstock, NY 12498

  • 3 Beds
  • 2 Baths
  • 1,787 Sq Ft
  • Built 1963

  64 Country Club Ln, Woodstock, NY 12498

  Last Sold Summary

  • 95 Days On Market

  Last Listing Agent Steve Hubbard Hubbard, Steve Real Estate
• 

  

  /26

  $349,000

  • Land
  • 3 Acres
  • $116,333 per Acre

  547 Glenford Wittenberg Rd, Bearsville, NY 12409

  Three acres available on Yankee Town Pond in Bearsville. Convenient to Woodstock yet only 15 minutes to the NYS Thruway. Minutes to the Ulster County Rail Trail w hiking and biking all at your fingertips. Love to fish? This is perfect. This lot is being subdivided from a larger parcel and will be a buildable lot with engineered plans for the house. The taxes and assessment reflect the entire

  Siobhan Scanlan Win Morrison Realty-K

  547 Glenford Wittenberg Rd, Bearsville, NY 12409
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  /24

  $206,000

  Sold Jul 14, 2026

  113 Meadow Ct, Woodstock, NY 12498

  • 2 Beds
  • 1 Bath
  • 894 Sq Ft
  • Built 1952

  Last Sold Summary

  • 18% Above List Price
  • $230/SF
  • 34 Days On Market

  Current Estimated Value $223,011

  Last Listing Agent Laura Warren Coldwell Banker Village Green

  113 Meadow Ct, Woodstock, NY 12498
• 

  

  /29

  Est $890,977

  Not Listed For Sale

  108 Ratterman Rd, Woodstock, NY 12498

  • 4 Beds
  • 3.5 Baths
  • 2,906 Sq Ft
  • Built 1959

  108 Ratterman Rd, Woodstock, NY 12498

  Last Sold Summary

  • 86 Days On Market

  Last Listing Agent Richard Vizzini Corcoran Country Living
• 

  

  /45

  $1,200,000

  • 4 Beds
  • 4 Baths
  • 3,172 Sq Ft

  5 Downer Ln, Woodstock, NY 12498

  Set on six bucolic acres along one of Woodstock's most scenic country roads, this extraordinary barn residence captures sweeping views of Overlook Mountain, the timeless beauty of the Hudson Valley landscape, and the quiet rhythm of a true farm setting.Reimagined from a historic 19th-century barn that was carefully disassembled and relocated from farther north, the home is a remarkable

  Baris Demirel Serhant LLC

  5 Downer Ln, Woodstock, NY 12498
• 

  $785,000

  Sold Apr 06, 2026

  90 Van Dale Rd, Woodstock, NY 12498

  • 4 Beds
  • 2.5 Baths
  • 2,034 Sq Ft
  • Built 1967

  Last Sold Summary

  • 1% Below List Price
  • $386/SF
  • 87 Days On Market

  Current Estimated Value $782,193

  Last Listing Agent Baris Demirel Serhant LLC

  90 Van Dale Rd, Woodstock, NY 12498
• 

  

  /39

  Est $1,025,955

  Not Listed For Sale

  115 Jones Quarry Rd, Woodstock, NY 12498

  • 3 Beds
  • 2 Baths
  • 3,010 Sq Ft
  • Built 1967

  115 Jones Quarry Rd, Woodstock, NY 12498

  Last Sold Summary

  • 38 Days On Market

  Last Listing Agent Margo Obourn Win Morrison Realty - W
• 

  $1,100,000

  Sold Apr 17, 2026

  178 Chestnut Hill Rd, Woodstock, NY 12498

  • 4 Beds
  • 2.5 Baths
  • 2,942 Sq Ft
  • Built 2024

  Last Sold Summary

  • 26% Below List Price
  • $374/SF
  • 37 Days On Market

  Last Listing Agent Richard Vizzini Corcoran Country Living

  178 Chestnut Hill Rd, Woodstock, NY 12498
• 

  

  /31

  Est $681,466

  Not Listed For Sale

  328 Ohayo Mountain Rd, Woodstock, NY 12498

  • 2 Beds
  • 2 Baths
  • 1,756 Sq Ft
  • Built 1934

  328 Ohayo Mountain Rd, Woodstock, NY 12498

  Last Sold Summary

  • 35 Days On Market

  Last Listing Agent Laurie Ylvisaker Coldwell Banker Village Green
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  /72

  $1,300,000

  Sold Jun 24, 2026

  1 Wittenberg Rd, Bearsville, NY 12409

  • 3 Beds
  • 3 Baths
  • 2,566 Sq Ft
  • Built 1873

  Last Sold Summary

  • 13% Below List Price
  • $507/SF
  • 127 Days On Market

  Current Estimated Value $1,351,933

  Last Listing Agent Jessica Brasseur Houlihan Lawrence, Inc.

  1 Wittenberg Rd, Bearsville, NY 12409
• 

  

  /27

  Est $422,141

  Not Listed For Sale

  178 Ohayo Mountain Rd, Woodstock, NY 12498

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • Built 1965

  178 Ohayo Mountain Rd, Woodstock, NY 12498

  Last Sold Summary

  • 40 Days On Market

  Last Listing Agent Gail Cadden Coldwell Banker Village Green
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  /55

  $762,900

  Sold Sep 10, 2026

  701 Zena-Highwoods Rd, Woodstock, NY 12498

  • 5 Beds
  • 4 Baths
  • 2,859 Sq Ft
  • Built 1979

  Last Sold Summary

  • 2% Above List Price
  • $267/SF
  • 14 Days On Market

  Last Listing Agent Mark Braverman Keller Williams Realty HV Nort

  701 Zena-Highwoods Rd, Woodstock, NY 12498
• 

  

  /58

  Est $1,144,444

  Not Listed For Sale

  2571 Route 212, Woodstock, NY 12498

  • 4 Beds
  • 2 Baths
  • 1,890 Sq Ft
  • Built 1939

  2571 Route 212, Woodstock, NY 12498

  Last Sold Summary

  • 213 Days On Market

  Last Listing Agent Jeanne Boice Howard Hanna Rand Realty
• 

  

  /38

  $885,000

  Sold Nov 21, 2025

  7 Maurizi Ln, Woodstock, NY 12498

  • 4 Beds
  • 2.5 Baths
  • 2,352 Sq Ft
  • Built 1979

  Last Sold Summary

  • 1% Below List Price
  • $376/SF
  • 30 Days On Market

  Current Estimated Value $920,380

  Last Listing Agent Catherine Quintard Compass Greater NY, LLC

  7 Maurizi Ln, Woodstock, NY 12498
• 

  

  /24

  Est $774,617

  Not Listed For Sale

  21 Casablanca Ln, Woodstock, NY 12498

  • 3 Beds
  • 1 Bath
  • 1,164 Sq Ft
  • Built 1963

  21 Casablanca Ln, Woodstock, NY 12498

  Last Sold Summary

  • 89 Days On Market

  Last Listing Agent Susanna Scott-Mitchell Compass Greater NY, LLC
• 

  $2,350,000

  Sold Jul 31, 2026

  9 Black Bear Rd, Bearsville, NY 12409

  • 4 Beds
  • 3 Baths
  • 3,539 Sq Ft
  • Built 1960

  Last Sold Summary

  • 4% Above List Price
  • $664/SF
  • 37 Days On Market

  Current Estimated Value $2,192,390

  Last Listing Agent Alexis Li Corcoran Country Living

  9 Black Bear Rd, Bearsville, NY 12409
• 

  

  /33

  Est $902,626

  Not Listed For Sale

  73 Ratterman Rd, Woodstock, NY 12498

  • 3 Beds
  • 3.5 Baths
  • 3,109 Sq Ft
  • Built 1958

  73 Ratterman Rd, Woodstock, NY 12498

  Last Sold Summary

  • 82 Days On Market

  Last Listing Agent Ita McAteer BHHS HUDSON VALLEY PROP-WDST
• 

  

  /33

  $810,000

  Sold Oct 24, 2025

  603-607 Wittenberg Rd, Mount Tremper, NY 12457

  • 5 Beds
  • 5 Baths
  • 3,085 Sq Ft
  • Built 1934

  Last Sold Summary

  • 5% Below List Price
  • $263/SF
  • 203 Days On Market

  Last Listing Agent Sharon Breslau BHHS HUDSON VALLEY PROP-WDST

  603-607 Wittenberg Rd, Mount Tremper, NY 12457
• 

  

  /23

  Est $713,383

  Not Listed For Sale

  5 Briarwood Ln, Woodstock, NY 12498

  • 3 Beds
  • 1 Bath
  • 2,195 Sq Ft
  • Built 1957

  5 Briarwood Ln, Woodstock, NY 12498

  Last Sold Summary

  • 55 Days On Market

  Last Listing Agent Mark Kanter BHHS HUDSON VALLEY PROP-WDST
• 

  

  /31

  $760,000

  Sold Oct 10, 2025

  49 Dorns Wood Rd, Woodstock, NY 12498

  • 4 Beds
  • 2.5 Baths
  • 2,657 Sq Ft
  • Built 1989

  Last Sold Summary

  • 1% Above List Price
  • $286/SF
  • 62 Days On Market

  Last Listing Agent Megan Rios Berardi Realty

  49 Dorns Wood Rd, Woodstock, NY 12498
• 

  

  /36

  Est $868,881

  Not Listed For Sale

  32 W Hurley Rd, Woodstock, NY 12498

  • 4 Beds
  • 3 Baths
  • 2,796 Sq Ft
  • Built 1948

  32 W Hurley Rd, Woodstock, NY 12498

  Last Sold Summary

  • 166 Days On Market

  Last Listing Agent Harris Safier Compass Greater New York, LLC
• 

  

  /49

  $1,550,000

  Sold Aug 04, 2026

  53 Little Deer Rd, Mount Tremper, NY 12457

  • 3 Beds
  • 3 Baths
  • 2,942 Sq Ft
  • Built 1971

  Last Sold Summary

  • 6% Below List Price
  • $527/SF
  • 27 Days On Market

  Current Estimated Value $1,575,382

  Last Listing Agent Quinn Hagstrand BHHS HUDSON VALLEY PROP-WDST

  53 Little Deer Rd, Mount Tremper, NY 12457
• 

  

  /20

  Est $522,637

  Not Listed For Sale

  123 Ohayo Mountain Rd, Woodstock, NY 12498

  • 2 Beds
  • 1.5 Baths
  • 958 Sq Ft
  • Built 1970

  123 Ohayo Mountain Rd, Woodstock, NY 12498

  Last Sold Summary

  • 27 Days On Market

  Last Listing Agent Mark Kanter BHHS HUDSON VALLEY PROP-WDST

Showing Results 281 - 320, Page 8 of 18