Woodstock, NY Homes

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  /37

  $749,000

  Open Sun 11AM - 1PM

  • 3 Beds
  • 3 Baths
  • 1,991 Sq Ft

  72 Van Dale Rd, Woodstock, NY 12498

  Nestled in a quiet Woodstock neighborhood five minutes from the village center and a short drive from Kingston, The Van Dale offers the privacy of nature without sacrificing convenience. Set on 1.36 acres in a quiet neighborhood, the property is bordered by a private creek that winds through the backyard, creating a peaceful natural setting just minutes from some of the Hudson Valley's most

  Leslie Foti Coldwell Banker Village Green

  72 Van Dale Rd, Woodstock, NY 12498
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  /28

  $6,200 Per Month

  • 3 Beds
  • 2 Baths
  • 1,164 Sq Ft
  • House for Rent

  535 Mink Hollow Rd, Woodstock, NY 12498

  Tucked into a lush, storybook setting where a gentle stream winds through the landscape and the forest feels just within reach, this fully renovated Woodstock bungalow offers a rare blend of charm, privacy, and effortless modern living. Immaculately landscaped grounds create a true outdoor sanctuary, with multiple dining areas, a firepit for slow evenings under the stars, and peaceful vantage

  Catherine Quintard Compass Greater NY, LLC

  535 Mink Hollow Rd, Woodstock, NY 12498
• 

  

  

  /27

  $370,000

  Sold Oct 31, 2025

  38 Arnold Dr, Woodstock, NY 12498

  • 3 Beds
  • 1.5 Baths
  • 1,365 Sq Ft
  • Built 1961

  Last Sold Summary

  • 14% Below List Price
  • $271/SF
  • 48 Days On Market

  Current Estimated Value $405,231

  Last Listing Agent Laura Prince Hudson Dwellings Realty

  38 Arnold Dr, Woodstock, NY 12498
• 

  Not Listed For Sale

  1183-1185 Wittenberg Rd, Mount Tremper, NY 12457

  • 10 Beds
  • 3 Baths
  • 3,954 Sq Ft
  • Built 1924

  1183-1185 Wittenberg Rd, Mount Tremper, NY 12457

  Last Sold Summary

  • 151 Days On Market
• 

  

  

  /39

  $1,495,000

  Pending

  • 3 Beds
  • 3 Baths
  • 2,064 Sq Ft

  529 Mount Guardian Rd, Woodstock, NY 12409

  Welcome to the Mount Guardian Modern. Positioned on nearly four acres on Mount Guardian, this Woodstock contemporary is the rare new construction that gets everything right: the siting, the light, the materials, the silence. Completed in 2021, it offers three bedrooms, three bathrooms, and 2,064 square feet of architecture that feels both intentional and effortless, anchored by a first-floor

  Laurie Ylvisaker Coldwell Banker Village Green

  529 Mount Guardian Rd, Woodstock, NY 12409
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  /36

  $16,500 Per Month

  • 4 Beds
  • 2.5 Baths
  • 2,394 Sq Ft
  • House for Rent

  75 Hill 99, Woodstock, NY 12498

  AVAIL FROM SEPT 2025. Secluded Mountain Chalet with Breathtaking Views and Poolside Lodge - Set atop nine private acres, this stunning mountaintop chalet offers a rare combination of serenity, seclusion, and spectacular views. A long, private driveway winds through the property, leading to a retreat unlike any other. The property features a three-story main house and a separate two-story Poolside

  Alexis Li Corcoran Country Living

  75 Hill 99, Woodstock, NY 12498
• 

  

  /34

  $675,000

  Sold May 27, 2026

  117 Ohayo Mountain Rd, Woodstock, NY 12498

  • 2 Beds
  • 1 Bath
  • 1,436 Sq Ft
  • Built 1952

  Last Sold Summary

  • 4% Above List Price
  • $470/SF
  • 21 Days On Market

  Current Estimated Value $654,552

  Last Listing Agent Donna Brooks Compass Greater New York, LLC

  117 Ohayo Mountain Rd, Woodstock, NY 12498
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  Not Listed For Sale

  363 Cold Brook Rd, Bearsville, NY 12409

  • 3 Beds
  • 2 Baths
  • 3,126 Sq Ft
  • Built 1985

  363 Cold Brook Rd, Bearsville, NY 12409

  Last Sold Summary

  • 117 Days On Market
• 

  

  /40

  $749,000

  Under Contract

  • 3 Beds
  • 2.5 Baths
  • 1,969 Sq Ft

  364 John Joy Rd, Woodstock, NY 12498

  Set off a quiet lane and approached by a gracious circular driveway, this classic Cape Cod carries the particular confidence of a house that has always known exactly what it is. Spanning 1,969 square feet, the home has been thoughtfully refreshed throughout with all-new wood flooring, freshly painted interiors, updated bathrooms, and an eat-in kitchen with marble countertops and custom wood

  Laurie Ylvisaker Coldwell Banker Village Green

  364 John Joy Rd, Woodstock, NY 12498
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  /31

  $12,000 Per Month

  • 3 Beds
  • 2.5 Baths
  • 2,200 Sq Ft
  • House for Rent

  206 Hutchin Hill Rd, Bearsville, NY 12409

  Escape the City and Find Your Peace Experience the height of summer in the Hudson Valley at this contemporary mountain home located on one of Woodstock's most coveted roads. This private sanctuary offers the perfect blend of secluded nature and modern luxury, just minutes from the Bearsville Theater and the heart of Woodstock village. Contemporary Design: An architectural gem featuring an

  Melissa Zoe Hirsch Coldwell Banker Village Green

  206 Hutchin Hill Rd, Bearsville, NY 12409
• 

  

  /27

  $942,200

  Sold Apr 16, 2026

  58 Jones Quarry Rd, Woodstock, NY 12498

  • 3 Beds
  • 2.5 Baths
  • 2,552 Sq Ft
  • Built 1985

  Last Sold Summary

  • 1% Below List Price
  • $369/SF
  • 36 Days On Market

  Current Estimated Value $946,958

  Last Listing Agent Michelle Bergkamp William Pitt Sotheby's Interna

  58 Jones Quarry Rd, Woodstock, NY 12498
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  /24

  Not Listed For Sale

  18 Vandermark Rd, Woodstock, NY 12498

  • 2 Beds
  • 2 Baths
  • 950 Sq Ft
  • Built 2024

  18 Vandermark Rd, Woodstock, NY 12498

  Last Sold Summary

  • 24 Days On Market
• 

  

  /40

  $825,000

  • 3 Beds
  • 2 Baths
  • 1,532 Sq Ft

  97 John Joy Rd, Woodstock, NY 12498

  Set beside one of Woodstock's most treasured and enduring landscapes, this quintessential Woodstock property unfolds along the edge of the Thorn Preserve--a protected 60-acre expanse celebrated for its sweeping open grasslands, riparian forest, ponds, and the most artist-captured views of Overlook Mountain. Even more remarkable, this landscape is permanently conserved, ensuring that the

  Richard Vizzini Corcoran Country Living

  97 John Joy Rd, Woodstock, NY 12498
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  /52

  $9,000 Per Month

  • 3 Beds
  • 2 Baths
  • 1,920 Sq Ft
  • House for Rent

  3870 New York 212, Bearsville, NY 12409

  Woodstock Summer 2026! Perched on a hill with panoramic views of the Cooper Lake this residence seamlessly blends European sophistication with Woodstock country vibes. Designed with an emphasis on light and line, the home features an open-concept layout framed by floor-to-ceiling glass, ensuring the mountain and lake vistas remain the focal point of every room. The interior aesthetic is a refined

  Melissa Zoe Hirsch Coldwell Banker Village Green

  3870 New York 212, Bearsville, NY 12409
• 

  

  /25

  $770,000

  Sold Mar 11, 2026

  86 Rock City Rd, Woodstock, NY 12498

  • 4 Beds
  • 2.5 Baths
  • 1,754 Sq Ft
  • Built 1910

  Last Sold Summary

  • 7% Below List Price
  • $439/SF
  • 90 Days On Market

  Current Estimated Value $758,201

  Last Listing Agent Michael Shaughnessy Halter Associates Realty

  86 Rock City Rd, Woodstock, NY 12498
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  /35

  Not Listed For Sale

  162 Van Dale Rd Unit 170, Woodstock, NY 12498

  • 3 Beds
  • 2 Baths
  • 2,299 Sq Ft
  • Built 1925

  162 Van Dale Rd Unit 170, Woodstock, NY 12498

  Last Sold Summary

  • 80 Days On Market
• 

  

  /44

  $3,325,000

  • 4 Beds
  • 3 Baths
  • 2,975 Sq Ft

  35 Van Wagner Rd, Willow, NY 12495

  More than a century in the making, and unlike anything else on the market, this extraordinary multi-residential estate began as a historic Hudson Valley farm before being thoughtfully transformed into a modern lifestyle retreat of remarkable scale and character. Over the years, musicians, entrepreneurs, and creative thinkers have called it home. Prior to that, it served as the Woodstock Farm

  Laurie Ylvisaker Coldwell Banker Village Green

  35 Van Wagner Rd, Willow, NY 12495
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  /49

  $5,500 Per Month

  • 3 Beds
  • 2 Baths
  • 1,342 Sq Ft
  • House for Rent

  299 Wittenberg Rd, Bearsville, NY 12409

  Luxury 3-Bed, 2-Bath Spa Retreat on over 6 Acres - Jet Tub, Sauna, Fire Pit & Handcrafted Natural Design Just 10 minutes from the heart of Woodstock and 5 minutes from the Bearsville Theater and restaurants, this stunning 3-bedroom, 2-bath retreat combines luxury, craftsmanship, and nature in perfect harmony. Every detail has been thoughtfully designed using only natural materials - stone, wood,

  Susanna Scott-Mitchell Compass Greater NY, LLC

  299 Wittenberg Rd, Bearsville, NY 12409
• 

  $1,150,000

  Sold Aug 22, 2025

  11 Louie Way, Woodstock, NY 12498

  • 2 Beds
  • 2 Baths
  • 2,209 Sq Ft
  • Built 1988

  Last Sold Summary

  • 5% Above List Price
  • $521/SF
  • 31 Days On Market

  Last Listing Agent Gary Heckelman Halter Associates Realty Inc

  11 Louie Way, Woodstock, NY 12498
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  /28

  Not Listed For Sale

  16 Deming St, Woodstock, NY 12498

  • 4 Beds
  • 1 Bath
  • 1,794 Sq Ft
  • Built 1930

  16 Deming St, Woodstock, NY 12498

  Last Sold Summary

  • 111 Days On Market
• 

  

  /23

  $415,000

  Pending

  • 3 Beds
  • 1.5 Baths
  • 1,033 Sq Ft

  92 Witch Tree Rd, Woodstock, NY 12498

  Pending, continue to show..Here is that very affordable, cute little three bedroom, one and a half bath Mid Century ranch in Woodstock that you have been waiting for! A Matterport walk through is available in videos. The semi-private lot is 1.2 level acres of beautifully groomed green areas, and a fully fenced large rear yard with cobblestone walls. This cozy home has hardwood floors, a beautiful

  William Chris St. John Win Morrison Realty

  92 Witch Tree Rd, Woodstock, NY 12498
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  /14

  $4,000 Per Month

  • 4 Beds
  • 2 Baths
  • 2,158 Sq Ft
  • House for Rent

  295 Grog Kill Rd, Willow, NY 12495

  SHORT TERM RENTAL: Private, fully furnished Woodstock Oasis with mountain views, is ready to be your country getaway! On a dead-end rd. up high on a hill, this Willow home has everything you need, close to hiking, skiing, restaurants and shopping, just minutes from Woodstock, Phoenicia and the NYS Thruway, this private retreat is available beginning March 2026

  Mark Kanter BHHS HUDSON VALLEY PROP-WDST

  295 Grog Kill Rd, Willow, NY 12495
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  /38

  $620,000

  Sold Sep 26, 2025

  3 Oriole Dr, Woodstock, NY 12498

  • 3 Beds
  • 2 Baths
  • 2,158 Sq Ft
  • Built 1967

  Last Sold Summary

  • 6% Above List Price
  • $287/SF
  • 32 Days On Market

  Current Estimated Value $617,505

  Last Listing Agent Mario Geissler Four Seasons Sotheby's Int'l R

  3 Oriole Dr, Woodstock, NY 12498
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  Not Listed For Sale

  15 Silver Wings Ln, Woodstock, NY 12498

  • 4 Beds
  • 6.5 Baths
  • 3,746 Sq Ft
  • Built 1900

  15 Silver Wings Ln, Woodstock, NY 12498

  Last Sold Summary

  • 58 Days On Market
• 

  

  /34

  $539,000

  $30K PRICE DROP

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

  110 Cottontail Ln, Woodstock, NY 12498

  Tucked away at the end of a quiet cul-de-sac in Woodstock, and set against a backdrop of woods, a gentle stream and mountain views, this well-maintained two-family home offers flexibility and income potential. The main residence features a welcoming living room, an eat-in kitchen, and a convenient half bath on the first floor. Upstairs, three bedrooms and a full bath provide a functional and

  Sally Sprogis Four Seasons Sothebys Intl

  110 Cottontail Ln, Woodstock, NY 12498
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  /30

  $8,750 Per Month

  • 4 Beds
  • 2.5 Baths
  • 2,333 Sq Ft
  • House for Rent

  10 Purdy Hollow Rd, Woodstock, NY 12498

  Summer Rental Opportunity: Rent by the month or the full season. Nestled in the serene hamlet of Zena, just five minutes from the heart of Woodstock, this exquisitely renovated cedar contemporary home offers a blend of elegance, comfort, and modern convenience. It is a sanctuary of refined living, set on three private acres directly across from the pristine 60-acre Thorn Preserve, which offers

  Leslie Foti Coldwell Banker Village Green

  10 Purdy Hollow Rd, Woodstock, NY 12498
• 

  

  /21

  $507,500

  Sold May 22, 2026

  78 van de Bogart Rd, Woodstock, NY 12498

  • 4 Beds
  • 1.5 Baths
  • 1,669 Sq Ft
  • Built 1964

  Last Sold Summary

  • 3% Below List Price
  • $304/SF
  • 97 Days On Market

  Last Listing Agent Melissa Zoe Hirsch Coldwell Banker Village Green

  78 van de Bogart Rd, Woodstock, NY 12498
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  /35

  Not Listed For Sale

  2292 Glasco Turnpike, Woodstock, NY 12498

  • 3 Beds
  • 3 Baths
  • 2,870 Sq Ft
  • Built 1924

  2292 Glasco Turnpike, Woodstock, NY 12498

  Last Sold Summary

  • 7 Days On Market
• 

  

  /31

  $525,000

  • 2 Beds
  • 2 Baths
  • 1,502 Sq Ft

  18 Elting Ln, Bearsville, NY 12409

  Come and see this cute-as-a-button, circa 1950 brick cape on Elting Lane, one of Woodstock's most enchanting roads! This easy-to-manage home on just shy of an acre, boasts woodland surroundings plus seasonal meadow and mountain views and fruit trees.The main floor features a light flooded living room with fireplace, an efficient kitchen with adjacent dining area with double glass doors

  Pamela Hoveling Halter Associates Realty

  18 Elting Ln, Bearsville, NY 12409
• 

  

  /23

  $4,200 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,374 Sq Ft
  • House for Rent

  527 Zena Rd, Woodstock, NY 12498

  This lovingly renovated 1900 farmhouse provides 1374 square feet of living space on 2 floors with 3 bedrooms and 2 1/2 bathrooms on a desirable road in Woodstock. On the ground floor, the property boasts a fantastic chef's eat-in kitchen, comfy living room and extra room with 1/2 bath. Upstairs you'll find a master bedroom with ensuite bathroom and 2 additional bedrooms with shared bathroom and

  Victoria Stent Coldwell Banker Village Green

  527 Zena Rd, Woodstock, NY 12498
• 

  

  /28

  $257,000

  Sold Feb 27, 2026

  259 Silver Hollow Rd, Willow, NY 12495

  • 1 Bath
  • 475 Sq Ft
  • Built 1950

  Last Sold Summary

  • 1% Below List Price
  • $541/SF
  • 58 Days On Market

  Current Estimated Value $252,031

  Last Listing Agent Leslie Foti Coldwell Banker Village Green

  259 Silver Hollow Rd, Willow, NY 12495
• 

  

  /34

  Est $808,936

  Not Listed For Sale

  5249 Route 212, Mount Tremper, NY 12457

  • 4 Beds
  • 3 Baths
  • 2,201 Sq Ft
  • Built 1990

  5249 Route 212, Mount Tremper, NY 12457

  Last Sold Summary

  • 63 Days On Market
• 

  

  /15

  $595,000

  Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,133 Sq Ft

  501 Ohayo Mountain Rd, Woodstock, NY 12498

  Discover your Upstate sanctuary in this contemporary 3-bedroom, 1.5-bath gem on Ohayo Mountain Road. Nestled in wooded bliss on 1.8 acres and in close proximity to protected state land, this home delivers a rare sense of peace and enduring natural beauty. Gleaming hardwood floors, a cozy wood-burning stove, and an open-concept floorplan perfect for modern living. Step outside to your private

  James Angelakis BHHS HUDSON VALLEY PROP-WDST

  501 Ohayo Mountain Rd, Woodstock, NY 12498
• 

  

  /15

  $3,800 Per Month

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

  35 Race Track Rd, Bearsville, NY 12409

  Sweet bungalow in Bearsville available for rent and move in ready. Down private country lane situated next to lovely stream on almost 3 acres minutes to the center of Woodstock sits this remodeled 2 Bd/ 1 Ba home with polished concrete floors and perfectly furnished with a modern aesthetic. Sit on your covered deck looking out into the Catskill forest. Lounge in your cozy living room beside your

  Johanna Trimboli Halter Associates Realty

  35 Race Track Rd, Bearsville, NY 12409
• 

  

  /40

  $1,055,000

  Sold Aug 20, 2025

  10 Magnolia Trail, Woodstock, NY 12498

  • 4 Beds
  • 3 Baths
  • 2,613 Sq Ft
  • Built 2016

  Last Sold Summary

  • 4% Below List Price
  • $404/SF
  • 34 Days On Market

  Last Listing Agent Joseph Satto Fresh Air Realty

  10 Magnolia Trail, Woodstock, NY 12498
• 

  

  /31

  Est $936,267

  Not Listed For Sale

  40 Grove Rd, Willow, NY 12495

  • 5 Beds
  • 4 Baths
  • 2,892 Sq Ft
  • Built 1990

  40 Grove Rd, Willow, NY 12495

  Last Sold Summary

  • 163 Days On Market
• 

  

  /11

  $435,000

  $64K PRICE DROP

  • Land
  • 15.23 Acres
  • $28,562 per Acre

  Tbd Wardwell Ln, Woodstock, NY 12498

  A rarely available large, 15+ acre parcel in Woodstock -- less than a mile from the center of town! Completely private yet moments away from restaurants, music venues, shops, golf course and hiking. A mixture of mature deciduous and conifer trees offer a forest haven, with level land, rock features and an elevated knoll building site, ready for your next chapter.Much of the heavy lifting has

  Laurie Osmond BHHS HUDSON VALLEY PROP-WDST

  Tbd Wardwell Ln, Woodstock, NY 12498
• 

  

  /15

  $3,600 Per Month

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

  36 Northwoods Rd Unit A, Woodstock, NY 12498

  A stunning, fully furnished guest house in a private setting in Woodstock! There's nothing more to ask for in this single level guest home with two bedrooms, a single bathroom and stunning open kitchen and living area. This home is naturally well-lit including skylights and picturesque nature views from each window. If this wasn't enough inside, step outside to your private outdoor area with

  Amy Hawks Berardi Realty

  36 Northwoods Rd Unit A, Woodstock, NY 12498
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  /42

  $967,500

  Sold Dec 05, 2025

  241 Silver Hollow Rd, Willow, NY 12495

  • 3 Beds
  • 2.5 Baths
  • 1,932 Sq Ft
  • Built 1963

  Last Sold Summary

  • 3% Below List Price
  • $501/SF
  • 47 Days On Market

  Current Estimated Value $975,953

  Last Listing Agent Carol Spirig Halter Associates Realty

  241 Silver Hollow Rd, Willow, NY 12495
• 

  

  /54

  Est $469,897

  Not Listed For Sale

  203 Maverick Rd, Woodstock, NY 12498

  • 2 Beds
  • 1.5 Baths
  • 960 Sq Ft
  • Built 1977

  203 Maverick Rd, Woodstock, NY 12498

  Last Sold Summary

  • 68 Days On Market

Showing Results 41 - 80, Page 2 of 18