Woodstock, NY Homes

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  /49

  $799,999

  $25K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,372 Sq Ft

  29 Maurizi Ln, Woodstock, NY 12498

  Set on an almost 3-acre wooded lot, this property has so much to offer in a quiet location close to the Village Green. On the main floor, you have a choice of rooms in which to entertain. A generous foyer leads to a comfortable living room with an actual dining room opposite. Beyond that space, a bright, recently redone, cheery eat-in kitchen awaits. Down the hall, for those cozy nights, a

  Henry Ford Coldwell Banker Village Green

  29 Maurizi Ln, 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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  /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 $659,541

  Last Listing Agent Donna Brooks Compass Greater New York, LLC

  117 Ohayo Mountain Rd, Woodstock, NY 12498
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  /35

  Est $2,339,034

  Not Listed For Sale

  150 Meads Mountain Rd, Woodstock, NY 12498

  • 3 Beds
  • 3.5 Baths
  • 2,896 Sq Ft
  • Built 1995

  150 Meads Mountain Rd, Woodstock, NY 12498

  Last Sold Summary

  • 28 Days On Market

  Last Listing Agent Melissa Mayes Serhant LLC
• 

  

  

  /44

  $725,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 1,905 Sq Ft

  17 Knolls Ct, Woodstock, NY 12498

  Rarely available and beautifully renovated, this two-story residence at Maverick Knolls offers a unique opportunity to own in Woodstock's only townhouse condominium community. Nestled toward the back in one of the community's most private settings, this turnkey 3-bedroom, 2.5-bath home combines style, comfort, and convenience just minutes from the heart of Woodstock. The home features new wood

  Gail Cadden Coldwell Banker Village Green

  17 Knolls Ct, Woodstock, NY 12498
• 

  

  /15

  $3,400 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
• 

  

  /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 $934,623

  Last Listing Agent Michelle Bergkamp William Pitt Sotheby's Interna

  58 Jones Quarry Rd, Woodstock, NY 12498
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  /16

  Not Listed For Sale

  5305 New York 212, Mount Tremper, NY 12457

  5305 New York 212, Mount Tremper, NY 12457

  Last Sold Summary

  • 74 Days On Market

  Last Listing Agent Faye Storms Ruth Gale Realty
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  /56

  $2,300,000

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

  56 Lauren Ct, Woodstock, NY 12498

  Exceptional 3 bedroom, 4 bath light-filled contemporary home offering refined nouvelle living set on over 4 private acres in Woodstock, NY. This home has had a complete interior high-end designer renovation that has been thoughtfully curated with sophisticated finishes and fine craftsmanship blending seamless luxury, comfort, and architectural elegance.A dramatic great room framed by soaring

  Amy Owens Coldwell Banker Village Green

  56 Lauren Ct, Woodstock, NY 12498
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  /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
• 

  

  /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 $777,572

  Last Listing Agent Michael Shaughnessy Halter Associates Realty

  86 Rock City Rd, Woodstock, NY 12498
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  Not Listed For Sale

  0 Wittenberg Rd Unit KEYH6302035, Woodstock, NY 12498

  0 Wittenberg Rd Unit KEYH6302035, Woodstock, NY 12498

  Last Sold Summary

  • 64 Days On Market

  Last Listing Agent Sean Zimmerman Halter Associates Realty Inc
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  /37

  $749,000

  • 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
• 

  $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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  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

  Last Listing Agent Roadman Etienne BHHS Hudson Valley Properties
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  /40

  $749,000

  Pending

  • 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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  /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 $627,926

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

  3 Oriole Dr, Woodstock, NY 12498
• 

  

  /27

  Est $658,174

  Not Listed For Sale

  30 Little Deer Rd, Mount Tremper, NY 12457

  • 1 Bed
  • 1 Bath
  • 1,350 Sq Ft
  • Built 1974

  30 Little Deer Rd, Mount Tremper, NY 12457

  Last Sold Summary

  • 43 Days On Market

  Last Listing Agent Quinn Hagstrand BHHS HUDSON VALLEY PROP-WDST
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  /37

  $815,000

  Under Contract

  • 2 Beds
  • 2 Baths
  • 2,471 Sq Ft

  376 Abbey Rd, Mount Tremper, NY 12457

  This classic contemporary retreat owned by the same family for over 2 decades is privately nestled on five picturesque acres along one of Woodstock's most coveted roads. Tucked away on a town-maintained dead-end lane, the property offers exceptional privacy and a true escape, all while remaining just minutes from the heart of Woodstock.Filled with natural light, this two-bedroom, two-bathroom

  Victoria Stent Coldwell Banker Village Green

  376 Abbey Rd, Mount Tremper, NY 12457
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  /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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  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

  Last Listing Agent Carol Spirig Halter Associates Realty Inc
• 

  

  /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
• 

  

  /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 $262,977

  Last Listing Agent Leslie Foti Coldwell Banker Village Green

  259 Silver Hollow Rd, Willow, NY 12495
• 

  

  /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

  Last Listing Agent Zachary Jarvis BHHS Nutshell Realty
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  /8

  $249,000

  • Land
  • 10 Acres
  • $24,900 per Acre

  4912 Ny-212, Willow, NY 12495

  Discover the opportunity to create your dream escape on this serene 10-acre parcel nestled in the quiet hamlet of Willow, NY. Tucked away in nature yet just a short drive from the vibrant village of Woodstock, this expansive property offers the perfect blend of privacy and proximity. Towering trees, dappled sunlight, and the calming sounds of nature create a peaceful setting for your future home,

  Richard Vizzini Corcoran Country Living

  4912 Ny-212, Willow, NY 12495
• 

  

  /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 Compass Greater NY, LLC

  10 Magnolia Trail, 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

  Last Listing Agent Jeannine Simmons Corcoran Country Living
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  /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
• 

  

  /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 $1,028,802

  Last Listing Agent Carol Spirig Halter Associates Realty

  241 Silver Hollow Rd, Willow, NY 12495
• 

  

  /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

  Last Listing Agent Toby Ress Win Morrison Realty - W
• 

  

  /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
• 

  

  /38

  $897,250

  Sold May 01, 2026

  52 Meher Cir, Woodstock, NY 12498

  • 3 Beds
  • 2 Baths
  • 2,200 Sq Ft
  • Built 1973

  Last Sold Summary

  • 1% Above List Price
  • $408/SF
  • 28 Days On Market

  Current Estimated Value $880,547

  Last Listing Agent Steven DiLorenzo Compass Greater NY LLC

  52 Meher Cir, 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

  Last Listing Agent Hailey Kiesewetter Upstate Down
• 

  

  /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
• 

  $810,000

  Sold Oct 24, 2025

  11 Grogkill Rd, Willow, NY 12495

  • 3 Beds
  • 2.5 Baths
  • 3,080 Sq Ft
  • Built 2006

  Last Sold Summary

  • 42% Below List Price
  • $263/SF
  • 78 Days On Market

  Current Estimated Value $1,102,555

  Last Listing Agent Sharon Breslau BHHS Hudson Valley Properties

  11 Grogkill Rd, Willow, NY 12495
• 

  

  /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

  Last Listing Agent Daniel Romero Compass Greater New York, LLC
• 

  

  /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
• 

  $607,000

  Sold Jan 23, 2026

  18 Niles Dr, Woodstock, NY 12498

  • 3 Beds
  • 2.5 Baths
  • 1,992 Sq Ft
  • Built 1965

  Last Sold Summary

  • 11% Above List Price
  • $305/SF
  • 29 Days On Market

  Current Estimated Value $627,162

  Last Listing Agent Laurel Sweeney BHHS Nutshell Realty

  18 Niles Dr, Woodstock, NY 12498
• 

  

  /34

  Est $799,461

  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

  Last Listing Agent Hillary Kolos Compass Greater NY, LLC
• 

  

  /13

  $599,000

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

  Lot 2 11 Marion's 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 Marion's Way, Woodstock, NY 12498

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