Woodstock, NY Homes

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  /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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• 

  

  

  /16

  $2,975 Per Month

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

  53 Rock City Rd, Woodstock, NY 12498

  Charming, recently updated 2-bedroom, one bath cottage for rent, offering 871 square feet of comfortable living space in in the heart of Woodstock.This inviting cottage is an ideal home base for enjoying the best of Woodstock and the Hudson Valley. Spend your mornings surrounded by nature, afternoons exploring local shops, galleries, hiking trails, and farm stands, and evenings enjoying

  Joel Craig Coldwell Banker Village Green

  53 Rock City Rd, Woodstock, NY 12498
• 

  

  

  /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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  /33

  Est $2,069,380

  Not Listed For Sale

  70 Raybrook Dr, Woodstock, NY 12498

  • 4 Beds
  • 3.5 Baths
  • 3,100 Sq Ft
  • Built 2013

  70 Raybrook Dr, Woodstock, NY 12498

  Last Sold Summary

  • 68 Days On Market

  Last Listing Agent Laurie Ylvisaker Coldwell Banker Village Green
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  /50

  $2,200,000

  Under Contract

  • 3 Beds
  • 2 Baths
  • 3,530 Sq Ft

  639 W Saugerties Rd, Woodstock, NY 12498

  A treehouse retreat on almost 46 Acres - a rare architectural sanctuary. Tucked into the forest canopy and perched dramatically over a private waterfall ravine, this one-of-a-kind 3,530 square foot home offers an extraordinary blend of architecture and untouched nature across 45.68 sprawling acres. The home's striking cedar-shingled exterior rises multiple stories on a soaring arched

  Henry Ford Coldwell Banker Village Green

  639 W Saugerties Rd, Woodstock, NY 12498
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  /57

  $3,900 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 DesignJust 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 -

  Susanna Scott-Mitchell Compass Greater NY, LLC

  299 Wittenberg Rd, 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 $777,572

  Last Listing Agent Michael Shaughnessy Halter Associates Realty

  86 Rock City Rd, Woodstock, NY 12498
• 

  Est $1,137,043

  Not Listed For Sale

  18 Maple Ln, Wood Stock, NY 12498

  • 6 Beds
  • 6 Baths
  • 4,400 Sq Ft
  • Built 1910

  18 Maple Ln, Wood Stock, NY 12498

  Last Sold Summary

  • 52 Days On Market

  Last Listing Agent Heidi Maloney Four Seasons Sothebys Intl
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  /44

  $2,995,000

  $330K PRICE DROP

  • 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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  /43

  $9,400 Per Month

  • 4 Beds
  • 3 Baths
  • 2,400 Sq Ft
  • House for Rent

  12 W Ohayo Mountain Rd, Bearsville, NY 12409

  Monthly, 6 month or Annual furnished rental available. Includes all utilities, lawn, plow, internet. Beautifullyfurnished, newly renovated 4 Bd/ 3 Ba rental available minutes to the center of Woodstock. Tucked down a quiet road with a private pastoral setting this home offers the ultimate one floor living with one bedroom/ bath on second floor. Living room with cathedral ceilings and exposed

  Johanna Trimboli Halter Associates Realty

  12 W Ohayo Mountain Rd, Bearsville, NY 12409
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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
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  /32

  Est $931,106

  Not Listed For Sale

  185 John Joy Rd, Wood Stock, NY 12498

  • 3 Beds
  • 3 Baths
  • 2,258 Sq Ft
  • Built 2015

  185 John Joy Rd, Wood Stock, NY 12498

  Last Sold Summary

  • 37 Days On Market

  Last Listing Agent Sheena Lepez Compass Greater New York, LLC
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  /42

  $2,300,000

  • 3 Beds
  • 4 Baths
  • 3,481 Sq Ft

  56 Lauren Ct, Kingston, NY 12401

  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, Kingston, NY 12401
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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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  /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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  /47

  Not Listed For Sale

  76-78 Mid Mountain Way, Woodstock, NY 12498

  • 2 Beds
  • 1.5 Baths
  • 1,673 Sq Ft
  • Built 1915

  76-78 Mid Mountain Way, Woodstock, NY 12498

  Last Sold Summary

  • 34 Days On Market

  Last Listing Agent Laurie Ylvisaker Coldwell Banker Village Green
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  /34

  $795,000

  Open Sat 11AM - 1PM Under Contract

  • 3 Beds
  • 2 Baths
  • 1,709 Sq Ft

  2614 Glasco Turnpike, Woodstock, NY 12498

  Tucked into the Hillside at Byrdcliffe, halfway up and just below the legendary White Pines of the 300 acre Byrdcliffe sanctuary, is a truly special Woodstock jewel.Hardwood floors flow throughout the easy one-level layout. The spacious living and dining areas fold seamlessly into a generous, bright kitchen, the natural heart of the home. The dining table sits adjacent to a large picture

  Laurie Ylvisaker Coldwell Banker Village Green

  2614 Glasco Turnpike, Woodstock, NY 12498
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  /48

  $5,800 Per Month

  • 3 Beds
  • 3.5 Baths
  • 2,355 Sq Ft
  • House for Rent

  2 Raycliffe Dr, Woodstock, NY 12498

  This exciting 7 year young modern home has everything you want. There is no end to the quality and workmanship emanating from this home. From the bamboo floors, high end Meile appliances, custom cabinetry, quartz countertops, top quality bath fixtures with soapstone countertops and several stained glass windows. To fully bring in light and the spectacular Overlook mountain views, you'll find a

  Richard Miller Win Morrison Realty - W

  2 Raycliffe Dr, Woodstock, NY 12498
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  /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
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  Not Listed For Sale

  11 Louie Way, Woodstock, NY 12498

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

  11 Louie Way, Woodstock, NY 12498

  Last Sold Summary

  • 31 Days On Market

  Last Listing Agent Gary Heckelman Halter Associates Realty Inc
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  /41

  $699,000

  Open Sat 12AM - 2PM

  • 1 Bed
  • 1 Bath
  • 1,179 Sq Ft

  35 Orchard Ln, Woodstock, NY 12498

  An opportunity to own a quintessentially Woodstock artist's home, set on half an acre, just moments from the heart of the village. This move-in-ready, character-filled 1920s property offers an appealing balance of original charm, contemporary comfort and exceptional flexibility for work, creativity and everyday living. A covered front porch, approached through colorful garden beds and a

  Laura Warren Coldwell Banker Village Green

  35 Orchard Ln, Woodstock, NY 12498
• 

  

  /15

  $3,500 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

  Amy Hawks Berardi Realty

  36 Northwoods Rd Unit A, 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
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  /36

  Est $1,444,276

  Not Listed For Sale

  97 Raycliffe Dr, Woodstock, NY 12498

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

  97 Raycliffe Dr, Woodstock, NY 12498

  Last Sold Summary

  • 31 Days On Market

  Last Listing Agent Richard Vizzini Corcoran Country Living
• 

  

  /14

  $199,000

  • Land
  • 3.19 Acres
  • $62,382 per Acre

  Lot 6 Mount Guardian Rd, Bearsville, NY 12409

  Discover 3.19 wooded acres in the heart of Bearsville, offering a rare opportunity to create your own Hudson Valley retreat just minutes from Woodstock. Set at the corner of Mt. Guardian Road and Mt. Guardian Road Extension, this fully wooded residentially zoned parcel is located along a privately maintained road in a peaceful, natural setting. Surrounded by the beauty and character that make the

  STEVEN WROBEL JR. Serhant LLC

  Lot 6 Mount Guardian Rd, Bearsville, NY 12409
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  /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
• 

  

  /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
• 

  

  /30

  $1,150,000

  • 4 Beds
  • 3.5 Baths
  • 2,448 Sq Ft

  9 Munchkin Ln, Kingston, NY 12401

  Selling fully furnished. 9 Munchkin Lane: A Designer Sanctuary in Woodstock Experience turnkey luxury on 5 private, wooded acres. Featured in Instagram’s "Best of Design," this stunning estate is being sold fully furnished—including all high-end decor, electronics, and linens. Just 5 miles from Tinker Street, the home has been meticulously renovated with exposed beams, hardwood floors, and a

  Jonathan Minerick HomeCoin.com

  9 Munchkin Ln, Kingston, NY 12401
• 

  $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
• 

  

  /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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  /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
• 

  $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
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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
• 

  

  /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
• 

  

  /19

  $375,000

  Sold Sep 17, 2026

  125 Tinker St, Woodstock, NY 12498

  • 2 Baths
  • 959 Sq Ft
  • Built 1945

  Last Sold Summary

  • 12% Below List Price
  • $391/SF
  • 71 Days On Market

  Current Estimated Value $416,985

  Last Listing Agent Peter Cantine Halter Associates Realty

  125 Tinker St, 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

  Last Listing Agent Roadman Etienne BHHS Hudson Valley Properties
• 

  

  /31

  $499,000

  $26K PRICE DROP

  • 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
• 

  

  /42

  $590,000

  Sold May 13, 2026

  83 Ratterman Rd, Woodstock, NY 12498

  • 5 Beds
  • 2.5 Baths
  • 1,939 Sq Ft
  • Built 1964

  Last Sold Summary

  • 8% Below List Price
  • $304/SF
  • 97 Days On Market

  Current Estimated Value $605,940

  Last Listing Agent Edwin Maldonado Howard Hanna Rand Realty

  83 Ratterman Rd, Woodstock, NY 12498
• 

  

  /28

  Est $552,526

  Not Listed For Sale

  44 Mink Hollow Rd, Willow, NY 12495

  • 3 Beds
  • 2 Baths
  • 1,867 Sq Ft
  • Built 1955

  44 Mink Hollow Rd, Willow, NY 12495

  Last Sold Summary

  • 93 Days On Market

  Last Listing Agent Lisa Halter Halter Associates Realty
• 

  

  /14

  $199,000

  • Land
  • 3.19 Acres
  • $62,382 per Acre

  Lot 6 Mt Guardian Rd, Bearsville, NY 12498

  Discover 3.19 wooded acres in the heart of Bearsville, offering a rare opportunity to create your own Hudson Valley retreat just minutes from Woodstock. Set at the corner of Mt. Guardian Road and Mt. Guardian Road Extension, this fully wooded residentially zoned parcel is located along a privately maintained road in a peaceful, natural setting.Surrounded by the beauty and character that make

  STEVEN WROBEL JR. Serhant LLC

  Lot 6 Mt Guardian Rd, Bearsville, NY 12498

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