Woodstock, NY Homes

• 

  

  

  /33

  Est $695,624

  Not Listed For Sale

  4 Oriole Dr, Woodstock, NY 12498

  • 4 Beds
  • 2 Baths
  • 2,430 Sq Ft
  • Built 1960

  4 Oriole Dr, Woodstock, NY 12498

  Last Sold Summary

  • 19 Days On Market

  Last Listing Agent Elizabeth Suib-Parisio Past Member
• 

  

  

  /33

  $595,000

  Under Contract

  • 3 Beds
  • 2 Baths
  • 1,321 Sq Ft

  419 Sickler Rd, Willow, NY 12495

  Relax, unwind, and take in the views from this charming cottage on one of the most bucolic and peaceful roads in the Woodstock hamlet of Willow--where every day feels like a weekend escape. The tranquility, mountain views, and picturesque valley setting have been cherished by one family for 47 years. Tucked away from the road and nearly invisible to passersby, the property welcomes you with the

  Marcia Weiss Halter Associates Realty

  419 Sickler Rd, Willow, NY 12495
• 

  

  

  /47

  $1,596,500

  Sold Jun 26, 2026

  41 Shultis Farm Rd, Bearsville, NY 12409

  • 3 Beds
  • 2.5 Baths
  • 2,064 Sq Ft
  • Built 2006

  Last Sold Summary

  • 7% Above List Price
  • $773/SF
  • 33 Days On Market

  Current Estimated Value $1,456,911

  Last Listing Agent Amy Lonas Coldwell Banker Village Green

  41 Shultis Farm Rd, Bearsville, NY 12409
• 

  

  

  /30

  Est $690,102

  Not Listed For Sale

  104 Cardinal Ct, Woodstock, NY 12498

  • 3 Beds
  • 2.5 Baths
  • 2,280 Sq Ft
  • Built 1967

  104 Cardinal Ct, Woodstock, NY 12498

  Last Sold Summary

  • 59 Days On Market

  Last Listing Agent Hayes Clement Compass Greater New York, LLC
• 

  

  

  /41

  $1,450,000

  • 3 Beds
  • 2 Baths
  • 2,560 Sq Ft

  96 Wittenberg Rd, Bearsville, NY 12409

  There’s a distinctly Bohemian heartbeat to this Woodstock compound — the kind of place where every corner feels like it has a story to tell or awaits the hearing of yours. The 1850 respectfully updated, original farmhouse, with its rich hand-hewn beams, gleaming wide floorboards, and six over six windows carries the patina of time, offering warmth, charm, and the kind of character that make old

  Eliane Abramoff Four Seasons Sothebys Intl

  96 Wittenberg Rd, Bearsville, NY 12409
• 

  

  /29

  $860,000

  Sold Jan 08, 2026

  45 Rose Ln, Bearsville, NY 12409

  • 2 Beds
  • 1.5 Baths
  • 1,684 Sq Ft
  • Built 1985

  Last Sold Summary

  • 14% Below List Price
  • $511/SF
  • 75 Days On Market

  Current Estimated Value $918,745

  Last Listing Agent Johanna Trimboli Halter Associates Realty

  45 Rose Ln, Bearsville, NY 12409
• 

  

  /24

  Est $1,102,917

  Not Listed For Sale

  46 John Joy Rd, Woodstock, NY 12498

  • 4 Beds
  • 2 Baths
  • 1,923 Sq Ft
  • Built 1976

  46 John Joy Rd, Woodstock, NY 12498

  Last Sold Summary

  • 31 Days On Market

  Last Listing Agent Ashley Prather Corcoran Country Living
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  /36

  $1,700,000

  • 5 Beds
  • 5 Baths
  • 4,628 Sq Ft

  7 Downer Ln, Woodstock, NY 12498

  A Woodstock compound with two distinct residences on eight acres, currently set up as STR. Included as part of this unique offering, 7 Downer Road brings an entirely different yet equally compelling dimension to the property. Set on approximately two private acres with beautiful mountain views, this authentic mid-century ranch captures the simplicity and warmth. The one-bedroom home retains many

  Baris Demirel Serhant LLC

  7 Downer Ln, Woodstock, NY 12498
• 

  

  /36

  $1,404,000

  Sold Aug 25, 2025

  97 Raycliffe Dr, Woodstock, NY 12498

  • 3 Beds
  • 3 Baths
  • 2,390 Sq Ft
  • Built 1988

  Last Sold Summary

  • 3% Below List Price
  • $587/SF
  • 31 Days On Market

  Current Estimated Value $1,444,276

  Last Listing Agent Richard Vizzini Corcoran Country Living

  97 Raycliffe Dr, Woodstock, NY 12498
• 

  

  /24

  Est $491,508

  Not Listed For Sale

  296 Yerry Hill Rd, Woodstock, NY 12498

  • 3 Beds
  • 2 Baths
  • 1,279 Sq Ft
  • Built 1942

  296 Yerry Hill Rd, Woodstock, NY 12498

  Last Sold Summary

  • 64 Days On Market

  Last Listing Agent Benjamin Armento Coldwell Banker Village Green
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  /48

  $679,000

  $50K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,128 Sq Ft

  14 Lions Way, Shady, NY 12409

  The essence of Woodstock; the artists, the poets, the musicians and the creatives who have gravitated to the beautiful, iconic Catskill Mountain town, no-one embodies the original spirit of Woodstock more than local artist and environmentalist Calvin Grimm. Every home tells a story. This custom built home.tucked away on 2 private acres with mountain views on a dead end lane speaks volumes.

  Johanna Trimboli Halter Associates Realty

  14 Lions Way, Shady, NY 12409
• 

  $308,000

  Sold Dec 09, 2025

  20 Overlook Dr, Woodstock, NY 12498

  • 3 Beds
  • 1 Bath
  • 917 Sq Ft
  • Built 1956

  Last Sold Summary

  • 3% Above List Price
  • $336/SF
  • 42 Days On Market

  Current Estimated Value $319,083

  Last Listing Agent Baris Demirel Serhant LLC

  20 Overlook Dr, Woodstock, NY 12498
• 

  

  /16

  Est $323,218

  Not Listed For Sale

  318 Yerry Hill Rd, Woodstock, NY 12498

  • 2 Beds
  • 1 Bath
  • 717 Sq Ft
  • Built 1940

  318 Yerry Hill Rd, Woodstock, NY 12498

  Last Sold Summary

  • 103 Days On Market

  Last Listing Agent Megan Rios Berardi Realty
• 

  

  /13

  $599,000

  • Land
  • 7.18 Acres
  • $83,426 per Acre

  Lot 2 11 Marions Way, Woodstock, NY 12498

  A once-in-a-generation opportunity to create your dream home in the heart of Woodstock, the coolest small town in America. Nestled on 7 shovel-ready acres just moments from the vibrant village center, this exceptional property offers the perfect balance of privacy, natural beauty, and convenience. Steeped in local history, the land is one of the last remaining vacant parcels from an historic

  Joel Craig Coldwell Banker Village Green

  Lot 2 11 Marions Way, Woodstock, NY 12498
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  /63

  $970,000

  Sold Nov 03, 2025

  109 the Middle Way, Mount Tremper, NY 12457

  • 2 Beds
  • 2.5 Baths
  • 2,010 Sq Ft
  • Built 1988

  Last Sold Summary

  • 16% Below List Price
  • $483/SF
  • 62 Days On Market

  Current Estimated Value $1,048,954

  Last Listing Agent Catherine Quintard Compass Greater NY, LLC

  109 the Middle Way, Mount Tremper, NY 12457
• 

  /2

  Est $3,350,789

  Not Listed For Sale

  1073 Wittenberg Rd, Mount Tremper, NY 12457

  • 5 Beds
  • 4 Baths
  • 3,848 Sq Ft
  • Built 1926

  1073 Wittenberg Rd, Mount Tremper, NY 12457
• 

  

  /33

  $1,750,000

  Pending

  • Land
  • 60.94 Acres
  • $28,717 per Acre

  Tbd Mulberry Ln, Woodstock, NY 12498

  An incredible, rare opportunity in Woodstock. It has been very long time since a parcel of this magnitude has available for sale in Woodstock. This contiguous 60-acre property, consisting of two 30-acre lots, features rolling hills, stunning rock outcroppings, mountain views, and diverse mature trees, uniquely offering both beauty and potential. A privately built road, completed by the owners,

  Baris Demirel Serhant LLC

  Tbd Mulberry Ln, Woodstock, NY 12498
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  /37

  $670,000

  Sold Oct 30, 2025

  10 Niles Dr, Woodstock, NY 12498

  • 4 Beds
  • 2 Baths
  • 2,008 Sq Ft
  • Built 1966

  Last Sold Summary

  • 1% Below List Price
  • $334/SF
  • 14 Days On Market

  Current Estimated Value $694,498

  Last Listing Agent Amy Owens Coldwell Banker Village Green

  10 Niles Dr, Woodstock, NY 12498
• 

  

  /43

  Est $524,456

  Not Listed For Sale

  11 Coyote Ct, Saugerties, NY 12477

  • 3 Beds
  • 2 Baths
  • 1,386 Sq Ft
  • Built 1988

  11 Coyote Ct, Saugerties, NY 12477

  Last Sold Summary

  • 83 Days On Market

  Last Listing Agent Kimberly Perry Howard Hanna Rand Realty
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  /26

  $470,000

  Under Contract

  • 2 Beds
  • 2 Baths
  • 1,284 Sq Ft

  123 Tinker St, Woodstock, NY 12498

  Woodstock Charm & Income Potential Near the Green Savvy investors and owner-occupants, take note of this exceptionally located 2-family property in high-demand Woodstock Hamlet rental market. Each of the two 650 sf sun-drenched units features 1 bedroom, 1 bathroom, and a classic country kitchen. Thoughtfully finished with a mix of rich wood and durable ceramic floors, the spaces feel bright,

  Peter Cantine Halter Associates Realty

  123 Tinker St, Woodstock, NY 12498
• 

  

  /23

  $675,000

  Sold Sep 15, 2025

  5 Briarwood Ln, Woodstock, NY 12498

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

  Last Sold Summary

  • 6% Below List Price
  • $308/SF
  • 55 Days On Market

  Current Estimated Value $713,383

  Last Listing Agent Mark Kanter BHHS HUDSON VALLEY PROP-WDST

  5 Briarwood Ln, Woodstock, NY 12498
• 

  

  /50

  Est $627,967

  Not Listed For Sale

  15 Schoonmaker Ln Unit 17, Woodstock, NY 12498

  • 2 Beds
  • 1 Bath
  • 1,044 Sq Ft
  • Built 1928

  15 Schoonmaker Ln Unit 17, Woodstock, NY 12498

  Last Sold Summary

  • 158 Days On Market

  Last Listing Agent Carol Spirig Halter Associates Realty
• 

  

  /13

  $135,000

  Pending

  • Land
  • 2 Acres
  • $67,500 per Acre

  0 Lot Cross Patch Rd, Woodstock, NY 12495

  Come experience the restorative powers of a mediative rest along side a rushing mountain creek. This 2 acre parcel with frontage on the East Branch of the Silver Hollow Creek will be an amazing location to build that country home that you have been envisioning. There is survey and preliminary site plan sketch to help you envision your dream. This parcel features a 19th Century building foundation

  Sean Zimmerman Halter Associates Realty

  0 Lot Cross Patch Rd, Woodstock, NY 12495
• 

  

  /38

  $635,000

  Sold Nov 06, 2025

  92 Erikas Walk, Mount Tremper, NY 12457

  • 3 Beds
  • 2 Baths
  • 1,684 Sq Ft
  • Built 1985

  Last Sold Summary

  • 2% Below List Price
  • $377/SF
  • 54 Days On Market

  Current Estimated Value $699,405

  Last Listing Agent Leslie Foti Coldwell Banker Village Green

  92 Erikas Walk, Mount Tremper, NY 12457
• 

  

  /15

  Est $792,547

  Not Listed For Sale

  63 Rock City Rd, Woodstock, NY 12498

  • 3 Beds
  • 3 Baths
  • 2,065 Sq Ft
  • Built 1974

  63 Rock City Rd, Woodstock, NY 12498

  Last Sold Summary

  • 54 Days On Market

  Last Listing Agent Gary Heckelman Halter Associates Realty
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  /63

  $915,000

  Under Contract

  • 3 Beds
  • 3 Baths
  • 2,265 Sq Ft

  15 Chipmunk Ln, Woodstock, NY 12498

  Rarely does a Woodstock home come along with this much soul, flexibility, and built-in opportunity. Tucked away on just over an acre off private Chipmunk Lane, this charming 2265 sq ft Cape Cod cottage style home captures the feeling people come to Woodstock hoping to find: a little privacy, a little magic, a little room to create, and a home that feels deeply personal from the moment you arrive.

  Dylan Taft Taft Street Realty, Inc.

  15 Chipmunk Ln, Woodstock, NY 12498
• 

  

  /36

  $299,000

  Sold Nov 12, 2025

  00 Lot 2 Church Rd, Woodstock, NY 12409

  • Land
  • 8.05 Acres
  • $37,143 per Acre

  Last Sold Summary

  • 105 Days On Market

  Last Listing Agent Melissa McGill Coldwell Banker Village Green

  00 Lot 2 Church Rd, Woodstock, NY 12409
• 

  

  /22

  Est $609,559

  Not Listed For Sale

  2281 Glasco Turnpike, Woodstock, NY 12498

  • 2 Beds
  • 2 Baths
  • 1,352 Sq Ft
  • Built 1996

  2281 Glasco Turnpike, Woodstock, NY 12498

  Last Sold Summary

  • 33 Days On Market

  Last Listing Agent Richard Vizzini Corcoran Country Living
• 

  

  /38

  $524,000

  Pending

  • 1 Bed
  • 1 Bath
  • 978 Sq Ft

  19 Schoonmaker Ln, Woodstock, NY 12498

  Built in 1908, this charming Woodstock home blends cottage warmth, handcrafted character, and a subtle Arts & Crafts sensibility. Less than a mile from the center of town yet off a quiet country lane, this home offers a peaceful haven, natural surroundings, and versatile spaces that extend beyond the main house. Much of the original character remains, including beautifully preserved wood floors,

  Adeline Ramirez Halter Associates Realty

  19 Schoonmaker Ln, Woodstock, NY 12498
• 

  

  /41

  $737,000

  Sold Sep 24, 2025

  1807 Glasco Turnpike, Woodstock, NY 12498

  • 3 Beds
  • 1.5 Baths
  • 2,290 Sq Ft
  • Built 1903

  Last Sold Summary

  • 13% Above List Price
  • $322/SF
  • 21 Days On Market

  Current Estimated Value $781,986

  Last Listing Agent Melissa Mayes Serhant LLC

  1807 Glasco Turnpike, Woodstock, NY 12498
• 

  

  /22

  Est $458,658

  Not Listed For Sale

  2289 Glasco Turnpike, Woodstock, NY 12498

  • 1 Bed
  • 1 Bath
  • 1,040 Sq Ft
  • Built 1953

  2289 Glasco Turnpike, Woodstock, NY 12498

  Last Sold Summary

  • 97 Days On Market

  Last Listing Agent Richard Vizzini Corcoran Country Living
• 

  

  /50

  $1,325,000

  • 8 Beds
  • 5.5 Baths
  • 4,648 Sq Ft

  2320 Glasco Turnpike, Woodstock, NY 12498

  Welcome to The Waterfall House, a rare opportunity tucked away in the heart of Woodstock Proper. Set on nearly 12 private acres, this classic brick Colonial offers an exceptional combination of privacy, natural beauty, and endless potential, all just minutes from the shops, restaurants, galleries, and vibrant arts scene that have made Woodstock an iconic destination. Offering approximately 3,000

  Leigh Wagner-Quintana KW Hudson Valley North

  2320 Glasco Turnpike, Woodstock, NY 12498
• 

  

  /39

  $700,000

  Sold Oct 22, 2025

  194 Wittenberg Rd, Bearsville, NY 12409

  • 3 Beds
  • 2.5 Baths
  • 1,592 Sq Ft
  • Built 1850

  Last Sold Summary

  • 12% Below List Price
  • $440/SF
  • 116 Days On Market

  Current Estimated Value $724,375

  Last Listing Agent Leslie Foti Coldwell Banker Village Green

  194 Wittenberg Rd, Bearsville, NY 12409
• 

  

  /34

  Est $588,625

  Not Listed For Sale

  50 Lower Byrdcliffe Rd, Woodstock, NY 12498

  • 2 Beds
  • 1 Bath
  • 1,201 Sq Ft
  • Built 1930

  50 Lower Byrdcliffe Rd, Woodstock, NY 12498

  Last Sold Summary

  • 138 Days On Market

  Last Listing Agent Toby Ress Win Morrison Realty - W
• 

  

  /39

  $775,000

  • 3 Beds
  • 2 Baths
  • 1,466 Sq Ft

  31 Pond Park Rd, Woodstock, NY 12498

  Woodstock Condo at Maverick Knolls Discover an exceptional opportunity to own a single-level corner condo in the desirable Maverick Knolls community of Woodstock, NY. This bright and airy residence combines convenience, modern updates, and the natural beauty of the Catskills, making it ideal for year-round living or as a low-maintenance retreat. The home has been refreshed with all new appliances

  Frank Lumia Frank Lumia Real Estate Plus

  31 Pond Park Rd, Woodstock, NY 12498
• 

  

  /32

  $710,000

  Sold Feb 06, 2026

  446 Abbey Rd, Woodstock, NY 12498

  • 3 Beds
  • 1.5 Baths
  • 1,468 Sq Ft
  • Built 1983

  Last Sold Summary

  • 3% Below List Price
  • $484/SF
  • 41 Days On Market

  Last Listing Agent Johanna Trimboli Halter Associates Realty

  446 Abbey Rd, Woodstock, NY 12498
• 

  

  /29

  Est $819,054

  Not Listed For Sale

  46 Lower Byrdcliffe Rd, Woodstock, NY 12498

  • 4 Beds
  • 2 Baths
  • 1,807 Sq Ft
  • Built 1928

  46 Lower Byrdcliffe Rd, Woodstock, NY 12498

  Last Sold Summary

  • 79 Days On Market

  Last Listing Agent Laurie Ylvisaker Coldwell Banker Village Green
• 

  

  /19

  $795,000

  $44K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,440 Sq Ft

  25 Pine Grove St Unit 27, Woodstock, NY 12498

  Streamside tranquility meets Village of Woodstock convenience in this beautifully renovated waterfront home. With Tannery Brook frontage extending to the centerline of the waterway, a sprawling deck overlooking the brook, and a stone stairway leading down to the water's edge, the setting is nothing short of enchanting. Inside, soaring 12.5-foot cathedral ceilings, expansive clerestory windows,

  Ita McAteer BHHS HUDSON VALLEY PROP-WDST

  25 Pine Grove St Unit 27, Woodstock, NY 12498
• 

  

  /17

  $455,000

  Sold Sep 22, 2025

  16 Delisio Ln, Woodstock, NY 12498

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

  Last Sold Summary

  • 14% Above List Price
  • $385/SF
  • 32 Days On Market

  Current Estimated Value $492,936

  Last Listing Agent Mark Kanter BHHS HUDSON VALLEY PROP-WDST

  16 Delisio Ln, Woodstock, NY 12498
• 

  

  /22

  Est $615,029

  Not Listed For Sale

  2411 Glasco Turnpike, Woodstock, NY 12498

  • 2 Beds
  • 2 Baths
  • 1,874 Sq Ft
  • Built 1860

  2411 Glasco Turnpike, Woodstock, NY 12498

  Last Sold Summary

  • 110 Days On Market

  Last Listing Agent Gail Saucier BHHS HUDSON VALLEY PROP-R

Showing Results 121 - 160, Page 4 of 18