Woodstock, NY Homes

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  /33

  $649,000 Under Contract

  • 2 Beds
  • 2 Baths
  • 1,208 Sq Ft

  18 Country Club Ln, Woodstock, NY 12498

  Welcome to 18 Country Club Lane. Located less than half a mile from the picturesque Village of Woodstock, this thoughtfully reimagined property offers easy access to shops, restaurants, fitness studios, playgrounds, and nearby nature trails, all just minutes from your front door. Designed by architects, the half-acre property includes two buildings and blends comfort, character, and modern

  Leslie Foti Coldwell Banker Village Green

  18 Country Club Ln, Woodstock, NY 12498
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  /53

  $4,900 per month

  • 3 Beds
  • 2 Baths
  • 1,876 Sq Ft
  • House for Rent

  17 Cross Patch Rd, Willow, NY 12495

  Beautifully renovated farmhouse set on 4.65 private acres with seasonal mountain views. This fully furnished 3BR/2BA home features an open floor plan, custom kitchen with vaulted ceilings, high-end appliances, marble countertops, and hardwood floors throughout. Living room with cobblestone fireplace and French doors to covered porch. Screened porch and large back deck overlook lush grounds.

  Susanna Scott-Mitchell Compass Greater NY, LLC

  17 Cross Patch Rd, Willow, NY 12495
• 

  $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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  /20

  Not Listed For Sale

  TBD Jessop Rd, Woodstock, NY 12498

  TBD Jessop Rd, Woodstock, NY 12498
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  /32

  $585,000 Under Contract

  • 2 Beds
  • 1 Bath
  • 1,783 Sq Ft

  110 Mill Hill Rd, Woodstock, NY 12498

  Can it get more magical than this? This property is a dream for anyone seeking a blend of artistic history and natural serenity. Experience true tranquility in a historic stone home where the landscape is the star. This property offers the rare opportunity to own both sides of the stream, ensuring total privacy for your morning dips in your private swimming holes. Host gatherings on the expansive

  Karen Sullivan Coldwell Banker Village GreenK

  110 Mill Hill Rd, Woodstock, NY 12498
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  /37

  $5,300 per month

  • 3 Beds
  • 2 Baths
  • 2,739 Sq Ft
  • House for Rent

  33 Race Track Rd, Bearsville, NY 12409

  ANNUAL FURNISHED RENTAL w POOL Lovely, meticulously maintained 3 bd/2 ba home with flex room and finished basement on amazing road. 3 plus bucolic acres minutes to the center of Woodstock HW floors, gourmet kitchen, living room with beautiful stone fireplace. Stone patio perfect for eating al fresco Sprawling grounds and gardens. Plenty of room to enjoy hosting family and friends.

  Johanna Trimboli Halter Associates Realty

  33 Race Track 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 $612,429

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

  3 Oriole Dr, Woodstock, NY 12498
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  /32

  Est $1,010,024 Not Listed For Sale

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

  185 John Joy Rd, Wood Stock, NY 12498

  185 John Joy Rd, Wood Stock, NY 12498
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  /27

  $949,000 Under Contract

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

  58 Jones Quarry Rd, Woodstock, NY 12498

  Set on over four acres just minutes from the heart of Woodstock, this contemporary retreat offers the perfect balance of modern living and a deep connection to nature. Thoughtfully designed for both comfort and flexibility, the home features three bedrooms and three bathrooms with a light-filled, open layout that encourages connection to the outdoors. The main level offers a full bathroom,

  Michelle Bergkamp William Pitt Sotheby's Interna

  58 Jones Quarry 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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  /39

  $522,000 Sold Mar 20, 2025

  250 MacDaniel Rd, Woodstock, NY 12498

  • 1 Bed
  • 1 Bath
  • 846 Sq Ft
  • Built 1984

  Last Sold Summary

  • 4% Above List Price
  • $617/SF
  • 46 Days On Market

  Last Listing Agent Darlene Griffin Halter Associates Realty

  250 MacDaniel 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
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  /22

  $699,000 Pending

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

  19 Livingston Ct, Woodstock, NY 12498

  Sophisticated Gated Retreat in Woodstock. Tucked within a serene, tree-lined neighborhood, this privately sited 4-bedroom, 2.5-bathroom colonial blends timeless comfort with thoughtful modern upgrades. Set behind a gated entry and encircled by approximately one acre of deer fencing, the property offers rare privacy while remaining minutes from the heart of Woodstock. Inside, natural light streams

  Timothy Ayers Berardi Realty

  19 Livingston Ct, Woodstock, NY 12498
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  /23

  $6,500 per month

  • 4 Beds
  • 2.5 Baths
  • 1,853 Sq Ft
  • House for Rent

  11 Shultis Farm Rd, Bearsville, NY 12409

  AVAIL FROM SEPT 2025. Private & Serene Modern Farmhouse Near Woodstock - Nestled on a private road just minutes from the heart of Woodstock, this beautifully renovated 4-bedroom, 2.5-bathroom modern farmhouse offers the perfect blend of charm, space, and privacy. Surrounded by mature trees, stone walls, and tall hedges, this home feels like a secluded retreat while remaining conveniently close

  Alexis Li Corcoran Country Living

  11 Shultis Farm Rd, Bearsville, NY 12409
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  /43

  $2,700,000 Sold Jun 13, 2025

  2655 Glasco Turnpike, Woodstock, NY 12498

  • 4 Beds
  • 3 Baths
  • 3,390 Sq Ft
  • Built 1945

  Last Sold Summary

  • 16% Below List Price
  • $796/SF
  • 209 Days On Market

  Current Estimated Value $2,775,352

  Last Listing Agent Richard Vizzini Corcoran Country Living

  2655 Glasco Turnpike, Woodstock, NY 12498
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  /24

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 950 Sq Ft

  18 Vandermark Rd, Woodstock, NY 12498

  18 Vandermark Rd, Woodstock, NY 12498
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  /29

  $898,000

  • 2 Beds
  • 2 Baths
  • 900 Sq Ft

  14 Old Forge Rd, Woodstock, NY 12498

  PROPERTY HIGHLIGHTS. Historic Meets Modern: Exquisitely renovated 1900 carriage house blending timeless charm with contemporary luxury. Layout: 2 bedrooms and 2 bathrooms. Exceptionally rare construction featuring Steel floor and ceiling joists with comprehensive Energy Efficient Upgrades throughout. INTERIOR FEATURESKITCHEN: Energy Efficient and dependable Bosch appliances. Custom

  Danielle Sevier Compass Greater NY, LLC

  14 Old Forge Rd, Woodstock, NY 12498
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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
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  $850,000 Sold May 08, 2025

  363 Cold Brook Rd, Bearsville, NY 12409

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

  Last Sold Summary

  • 23% Below List Price
  • $272/SF
  • 117 Days On Market

  Last Listing Agent Carol Spirig Halter Associates Realty Inc

  363 Cold Brook Rd, Bearsville, NY 12409
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  /35

  Not Listed For Sale

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

  162 Van Dale Rd Unit 170, Woodstock, NY 12498

  162 Van Dale Rd Unit 170, Woodstock, NY 12498
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  /49

  $785,000 Pending

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

  90 Van Dale Rd, Woodstock, NY 12498

  Make your next transition an easy one in this move-in-ready Woodstock home, where timeless comfort meets sophisticated design. Just minutes from Woodstock’s restaurants, music venues, and shops, it blends the best of convenience and style. With its modern updates, thoughtful details, and prime Woodstock location, 90 Van Dale strikes the perfect balance of comfort, practicality, and style.

  Baris Demirel Serhant LLC

  90 Van Dale Rd, Woodstock, NY 12498
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  /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
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  /28

  Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 1,794 Sq Ft

  16 Deming St, Woodstock, NY 12498

  16 Deming St, Woodstock, NY 12498
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  /36

  $1,195,000

  • 3 Beds
  • 4 Baths
  • 3,120 Sq Ft

  540 Mount Tobias Rd, Mount Tremper, NY 12457

  Step into the pages of Dwell magazine and immerse yourself in this architect-designed gem offering a harmonious blend of modern design and natural beauty. Feel a wave of calm wash over you, greeted by resplendent views, clean lines, and a wall of windows overlooking majestic mountain vistas. Modernists rejoice. Design aficionados delight. And nature enthusiasts revel. A minimalist aesthetic

  Alexander James Compass Greater NY, LLC

  540 Mount Tobias Rd, Mount Tremper, NY 12457
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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

  Last Listing Agent Carol Spirig Halter Associates Realty

  241 Silver Hollow Rd, Willow, NY 12495
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  Not Listed For Sale

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

  15 Silver Wings Ln, Woodstock, NY 12498

  15 Silver Wings Ln, Woodstock, NY 12498
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  /61

  $775,000

  • 2 Beds
  • 1.5 Baths
  • 1,410 Sq Ft

  15 Lake View Dr, Lake Hill, NY 12448

  Own this stunning, architect-designed contemporary home in Woodstock, NY. Professionally decorated and thoughtfully crafted with passive solar principles, this energy-efficient residence seamlessly blends modern design with its natural surroundings. Set just across the road from the famous Cooper Lake, the home is nestled in a beautiful, 3 acre wooded setting—private yet not isolated—surrounded

  Mackenzie Grate The Machree Group, LLC

  15 Lake View Dr, Lake Hill, NY 12448
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  $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 $1,031,619

  Last Listing Agent Sharon Breslau BHHS Hudson Valley Properties

  11 Grogkill Rd, Willow, NY 12495
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  /35

  Not Listed For Sale

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

  2292 Glasco Turnpike, Woodstock, NY 12498

  2292 Glasco Turnpike, Woodstock, NY 12498
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  /42

  $1,199,000 Under Contract

  • 5 Beds
  • 3 Baths
  • 3,696 Sq Ft

  3207-3209 New York 212, Bearsville, NY 12409

  Enchanting Woodstock Compound with three separate buildings—Craftsman Home, Historic Barn & Cottage. Welcome to a truly rare offering in the heart of the Catskills—just minutes from the center of Woodstock, yet tucked away in a storybook setting of trees, meadows, and the soothing sounds of the Sawkill stream. This private 1.85-acre homestead compound blends rustic charm with modern versatility,

  Michelle Bergkamp William Pitt Sotheby's Interna

  3207-3209 New York 212, Bearsville, NY 12409
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  $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

  Last Listing Agent Laurel Sweeney BHHS Nutshell Realty

  18 Niles Dr, Woodstock, NY 12498
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  /34

  Est $808,791 Not Listed For Sale

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

  5249 Route 212, Mount Tremper, NY 12457

  5249 Route 212, Mount Tremper, NY 12457
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  /51

  $759,000

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

  97 John Joy Rd, Woodstock, NY 12498

  The best of both worlds!A boho cottage paradise and a modern ADU (Accessory Dwelling Unit). Peace and tranquility and 3 miles from the center of the most famous small town in the world. Five-star dining and unique shopping opportunities. The property is situated adjacent to the Thorne Preserve - 60 acres boasting the most painted views of Overlook Mountain. The preserve is a sweeping

  Benjamin Armento Coldwell Banker Village Green

  97 John Joy Rd, Woodstock, NY 12498
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  /39

  $585,000 Sold Sep 12, 2025

  148 Hutchin Hill Rd, Shady, NY 12409

  • 2 Beds
  • 1 Bath
  • 1,039 Sq Ft
  • Built 1949

  Last Sold Summary

  • 2% Below List Price
  • $563/SF
  • 76 Days On Market

  Current Estimated Value $575,860

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

  148 Hutchin Hill Rd, Shady, NY 12409
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  /32

  Est $2,485,419 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 3,954 Sq Ft

  34 Vandebogart Rd, Woodstock, NY 12498

  34 Vandebogart Rd, Woodstock, NY 12498
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  /25

  $795,000 Pending

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

  86 Rock City Rd, Woodstock, NY 12498

  Woodstock Charm Meets Modern Living at 86 Rock City Road! Step into a piece of Woodstock history with this beautifully updated 1910 home, ideally located less than half a mile from the vibrant heart of the village. This 4-bedroom, 2.5-bath property blends classic charm with thoughtful modern upgrades. The spacious, fully renovated kitchen features new appliances, updated countertops, and ample

  Michael Shaughnessy Halter Associates Realty Inc

  86 Rock City Rd, Woodstock, NY 12498
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  /31

  $978,000 Sold Apr 21, 2025

  38 Vandebogart Rd, Woodstock, NY 12498

  • 4 Beds
  • 3.5 Baths
  • 3,914 Sq Ft
  • Built 1920

  Last Sold Summary

  • 3% Above List Price
  • $250/SF
  • 12 Days On Market

  Current Estimated Value $981,091

  Last Listing Agent Alexis Li Corcoran Country Living

  38 Vandebogart Rd, Woodstock, NY 12498
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  /22

  Est $671,735 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,106 Sq Ft

  6 Allen Dr, Woodstock, NY 12498

  6 Allen Dr, Woodstock, NY 12498
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  /47

  $879,000 Pending

  • 2 Beds
  • 2.5 Baths
  • 2,068 Sq Ft

  636 Zena Rd, Woodstock, NY 12498

  Every so often, a house comes along that feels less like real estate and more like a work of art, and this mid-century modern gem on Zena Road is exactly that. With its roots in the 1950's (though the tax rolls say 1970), the home was designed by one of the last abstract expressionists, and it shows: glass, stone, and iron frame a structure that feels both timeless and deeply of its era. The home

  Kayla Camstra Anatole House LLC

  636 Zena Rd, Woodstock, NY 12498
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  /58

  $1,199,000 Sold Apr 04, 2025

  2571 Route 212, Woodstock, NY 12498

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

  Last Sold Summary

  • 20% Below List Price
  • $634/SF
  • 213 Days On Market

  Current Estimated Value $1,222,828

  Last Listing Agent Jeanne Boice Howard Hanna Rand Realty

  2571 Route 212, Woodstock, NY 12498

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