Woodstock, NY Homes

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  /50

  $2,350,000

  Coming Soon

  • 3 Beds
  • 2 Baths
  • 2,322 Sq Ft

  24 Tanis Hollow Rd, Woodstock, NY 12498

  Million-Dollar Views as Far as the Eye Can SeePerched privately on 5.1 acres with breathtaking 100-mile panoramic views, this extraordinary log home is a true architectural masterpiece. Constructed from massive 18 to 20 inch in diameter logs that required cranes for assembly and individually placed upon an expertly engineered foundation, this remarkable residence represents a level of

  

  Randy Spiesman

  Weichert REALTORS

  24 Tanis Hollow Rd, Woodstock, NY 12498
• Explore Woodstock

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  /24

  $25,000 Per Month

  • 4 Beds
  • 2.5 Baths
  • 3,029 Sq Ft
  • House for Rent

  84 Sickler Rd, Lake Hill, NY 12448

  A Summer Like No Other Awaits You. Escape the ordinary and step into a world where luxury meets the unhurried beauty of the countryside. Nestled gracefully upon 17 pristine acres, this exquisite farmhouse retreat is a rare offering -- a sanctuary where pastoral meadows, rolling mountain vistas, and timeless charm converge in perfect harmony. Thoughtfully positioned to capture breathtaking views

  Quinn Hagstrand BHHS HUDSON VALLEY PROP-WDST

  84 Sickler Rd, Lake Hill, NY 12448
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  /33

  $225,000

  Sold Aug 26, 2025

  23 Cottonwood Ln, Woodstock, NY 12498

  • 2 Beds
  • 1 Bath
  • 704 Sq Ft
  • Built 1966

  Last Sold Summary

  • 36% Below List Price
  • $320/SF
  • 61 Days On Market

  Current Estimated Value $272,794

  Last Listing Agent James Murphy Patty Conti Realty Group LLC

  23 Cottonwood Ln, Woodstock, NY 12498
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  /29

  Not Listed For Sale

  3555 Route 212, Woodstock, NY 12498

  • 2 Beds
  • 1 Bath
  • 1,162 Sq Ft
  • Built 1915

  3555 Route 212, Woodstock, NY 12498

  Last Sold Summary

  • 52 Days On Market
• 

  

  

  /47

  $1,490,000

  Pending

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

  41 Shultis Farm Rd, Bearsville, NY 12409

  Designed with intention and sited with care, this stunning single-level home on Shultis Farm Road is one of Woodstock's most architecturally pleasing offerings. Commissioned from a noted architect and built for effortless and peaceful country living, the residence unfolds across three bedrooms and two and a half baths with an easy flow that opens naturally to the outdoors. Located in the

  

  Amy Lonas

  Coldwell Banker Village Green

  41 Shultis Farm Rd, Bearsville, NY 12409
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  /8

  $2,300 Per Month

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft
  • Condo for Rent

  5-7 Rock City Rd Unit 3D, Woodstock, NY 12498

  5-7 Rock City Rd Unit 3D, Woodstock, NY 12498
• 

  

  /37

  $825,000

  Sold Nov 18, 2025

  16 Marko Grove, Woodstock, NY 12498

  • 4 Beds
  • 2 Baths
  • 2,350 Sq Ft
  • Built 1964

  Last Sold Summary

  • 4% Above List Price
  • $351/SF
  • 17 Days On Market

  Current Estimated Value $831,199

  Last Listing Agent Leslie Foti Coldwell Banker Village Green

  16 Marko Grove, Woodstock, NY 12498
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  /40

  Not Listed For Sale

  3906 New York 212, Lake Hill, NY 12448

  • 3 Beds
  • 2 Baths
  • 1,748 Sq Ft
  • Built 1983

  3906 New York 212, Lake Hill, NY 12448

  Last Sold Summary

  • 67 Days On Market
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  /52

  $649,000

  Under Contract

  • 3 Beds
  • 3.5 Baths
  • 2,856 Sq Ft

  3 Coyote Ct, Woodstock, NY 12498

  Private and peaceful, 3 Coyote Lane is set on 2 manicured acres along a quiet country road where Kingston, Saugerties and Woodstock meet. With 2,856 square feet of comfortable living space, this 3-bedroom, 3.5-bath home features a practical, well-designed layout with generous room sizes and flexible living areas.The primary suite is a defining feature of the home, offering an unusually

  

  Amy Lonas

  Coldwell Banker Village Green

  3 Coyote Ct, Woodstock, NY 12498
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  /20

  $9,800 Per Month

  • 4 Beds
  • 3 Baths
  • 2,714 Sq Ft
  • House for Rent

  64 Meher Cir, Woodstock, NY 12498

  Woodstock | Private Summer Residence with Pool | 4BR/3BA | May 22-Oct 31 Set on over two private acres in one of Woodstock's most desirable locations, this fully furnished 4-bedroom, 3-bath residence is available for an extended summer stay (31-day minimum). Recently renovated. Clean lines and strong natural light. Layout offers both flow and separation, with multiple areas for living, dining,

  Sheena Lepez Compass Greater New York, LLC

  64 Meher Cir, Woodstock, NY 12498
• 

  

  /50

  $976,000

  Sold Jan 29, 2026

  13 16 Torn Hill Rd, Bearsville, NY 12409

  • 4 Beds
  • 2.5 Baths
  • 2,780 Sq Ft
  • Built 1935

  Last Sold Summary

  • 12% Below List Price
  • $351/SF
  • 60 Days On Market

  Last Listing Agent Laurie Ylvisaker Coldwell Banker Village Green

  13 16 Torn Hill Rd, Bearsville, NY 12409
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  /35

  Est $1,249,069

  Not Listed For Sale

  2680 Glasco Turnpike, Wood Stock, NY 12498

  • 4 Beds
  • 2.5 Baths
  • 2,075 Sq Ft
  • Built 1898

  2680 Glasco Turnpike, Wood Stock, NY 12498

  Last Sold Summary

  • 56 Days On Market
• 

  

  /44

  $950,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,912 Sq Ft

  9 Chesters Place, Woodstock, NY 12498

  Tucked away at the end of a quiet dead-end road, just minutes from the center of Woodstock, 9 Chesters Place is the kind of home buyers ask for but rarely find. Lovingly maintained by two resident artists, the house reflects careful, creative stewardship and thoughtful details throughout. The home is nearly new, mindfully designed, and set in a peaceful, private setting. This bright, beautiful

  

  Amy Lonas

  Coldwell Banker Village Green

  9 Chesters Place, Woodstock, NY 12498
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  /11

  $5,500 Per Month

  • 2 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • House for Rent

  514 Ohayo Mountain Rd, Woodstock, NY 12498

  Woodstock Monthly Rental with Ashokan Reservoir Views | Private Main-Level Living in a Scenic Setting | July-August 2026 Spend a month living the Woodstock / Ashokan Reservoir lifestyle in this character-filled home set high above a peaceful stretch of Woodstock Road. With year-round reservoir views, a double-tiered yard, and a layout designed for easy indoor-outdoor living, this is the kind of

  Mark Kanter BHHS HUDSON VALLEY PROP-WDST

  514 Ohayo Mountain Rd, Woodstock, NY 12498
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  /41

  $892,000

  Sold Nov 04, 2025

  8 Pine Grove St, Woodstock, NY 12498

  • 5 Beds
  • 4 Baths
  • 2,426 Sq Ft
  • Built 1920

  Last Sold Summary

  • 10% Below List Price
  • $368/SF
  • 77 Days On Market

  Current Estimated Value $904,369

  Last Listing Agent Judy Steinfeld Halter Associates Realty

  8 Pine Grove St, Woodstock, NY 12498
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  /2

  Est $681,017

  Not Listed For Sale

  12 Tannery Brook Rd, Wood Stock, NY 12498

  • Studio
  • 2 Baths
  • 1,269 Sq Ft
  • Built 1975

  12 Tannery Brook Rd, Wood Stock, NY 12498
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  /52

  $1,180,000

  Under Contract

  • 3 Beds
  • 2 Baths
  • 1,772 Sq Ft

  34 Upper West Ohayo Mountain Rd, Bearsville, NY 12409

  Set on more than nine private acres just minutes from the heart of Woodstock, this elegant sprawling ranch is a rare offering where the views take center stage. Thoughtfully designed in the spirit of 1960s contemporary architecture, the home was created to celebrate its extraordinary natural setting, with sweeping vistas enjoyed from nearly every room. A substantial spring-fed pond, serene pine

  

  Amy Lonas

  Coldwell Banker Village Green

  34 Upper West Ohayo Mountain Rd, Bearsville, NY 12409
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  /36

  $19,500 Per Month

  • 4 Beds
  • 2 Baths
  • 1,499 Sq Ft
  • House for Rent

  55 Nordic Dr, Woodstock, NY 12498

  *SUMMER & FALL RENTAL* (AVAIL May 25 - Oct 31, 2026) // This unique hilltop property includes two separate structures -- a beautifully designed three-bedroom main house and a private loft guest house offering flexible space so you have accommodations for up to 10+ guests. Tucked away on a private hilltop ridge just under three miles from the pulse of Woodstock, 55 Nordic Drive is a secluded

  Alexis Li Corcoran Country Living

  55 Nordic Dr, Woodstock, NY 12498
• 

  $1,100,000

  Sold Jul 10, 2025

  18 Maple Ln, Wood Stock, NY 12498

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

  Last Sold Summary

  • 14% Below List Price
  • $250/SF
  • 52 Days On Market

  Current Estimated Value $1,124,809

  Last Listing Agent Heidi Maloney Four Seasons Sothebys Intl

  18 Maple Ln, Wood Stock, NY 12498
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  /30

  Not Listed For Sale

  18 Rock City Rd, Wood Stock, NY 12498

  • 3 Beds
  • 3 Baths
  • 2,683 Sq Ft
  • Built 1890

  18 Rock City Rd, Wood Stock, NY 12498

  Last Sold Summary

  • 132 Days On Market
• 

  

  /46

  $1,150,000

  $50K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,363 Sq Ft

  4599 New York 212, Willow, NY 12495

  Creekside Modern Home with Mountain Views Near Woodstock Surrounded by mountains with private access to a year-round creek, this thoughtfully designed home feels deeply connected to its setting while offering comfort, privacy, and modern convenience. Built in 2017 and significantly expanded and upgraded in 2022, the property blends clean contemporary design with warmth and functionality. Large

  

  Leigh Bokser

  Compass Greater NY, LLC

  4599 New York 212, Willow, NY 12495
• 

  

  /25

  $18,500 Per Month

  • 3 Beds
  • 2.5 Baths
  • 2,393 Sq Ft
  • House for Rent

  20 Handys Walk, Shady, NY 12409

  Here's your chance to spend a flexible season staring at one of the most incredible views this seasoned agent has ever seen in the Catskills. Featured in the book Woodstock Handmade Houses, this beautiful and private home on Overlook Mountain is the perfect marriage of Swedish minimalism and antique rustic materials. The panoramic views reveal themselves immediately upon entering the home. The

  Briana Cermak Compass Greater NY, LLC

  20 Handys Walk, Shady, NY 12409
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  /41

  $530,000

  Sold Dec 19, 2025

  5 Violet Place, Woodstock, NY 12498

  • 3 Beds
  • 1.5 Baths
  • 1,804 Sq Ft
  • Built 1963

  Last Sold Summary

  • 2% Below List Price
  • $294/SF
  • 33 Days On Market

  Current Estimated Value $535,505

  Last Listing Agent Fawn Denue Keller Williams Realty HV Nort

  5 Violet Place, Woodstock, NY 12498
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  /24

  Est $693,491

  Not Listed For Sale

  7 Lark Dr, Wood Stock, NY 12498

  • 3 Beds
  • 2.5 Baths
  • 1,345 Sq Ft
  • Built 2024

  7 Lark Dr, Wood Stock, NY 12498

  Last Sold Summary

  • 37 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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  /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
• 

  $4,600,000

  Sold Aug 25, 2025

  18 Striebel Rd, Woodstock, NY 12498

  • 4 Beds
  • 4 Baths
  • 3,899 Sq Ft
  • Built 1914

  Last Sold Summary

  • 8% Below List Price
  • $1,180/SF
  • 99 Days On Market

  Current Estimated Value $4,316,874

  Last Listing Agent Kathryn Johnson William Pitt Sothebys Int Rlty

  18 Striebel Rd, Woodstock, NY 12498
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  /35

  Est $1,831,033

  Not Listed For Sale

  85 Baumgarten Rd, Woodstock, NY 12498

  • 7 Beds
  • 3.5 Baths
  • 4,582 Sq Ft
  • Built 1720

  85 Baumgarten Rd, Woodstock, NY 12498

  Last Sold Summary

  • 54 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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  /12

  $2,900 Per Month

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

  2465 Glasco Turnpike Unit 1, Woodstock, NY 12498

  Enjoy the Woodstock lifestyle in this unique two-bedroom cottage with full bath set among the trees. Close to the Village, this charming cottage features an open-plan living area with a fireplace and Craftsman-style kitchen. Take pleasure in dining alfresco in the screened porch or relaxing outdoors on the wood deck or stone patio. For comfort and convenience, there are ample closets and a

  Lillian Kology Halter Associates Realty

  2465 Glasco Turnpike Unit 1, Woodstock, NY 12498
• 

  

  /20

  $325,000

  Sold Nov 04, 2025

  57 Overlook Dr, Woodstock, NY 12498

  • 2 Beds
  • 2 Baths
  • 1,177 Sq Ft
  • Built 1955

  Last Sold Summary

  • 1% Below List Price
  • $276/SF
  • 33 Days On Market

  Current Estimated Value $363,388

  Last Listing Agent Laurie Ylvisaker Coldwell Banker Village Green

  57 Overlook Dr, Woodstock, NY 12498
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  /33

  Est $2,071,620

  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
• 

  

  /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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  /24

  $4,200 Per Month

  • 2 Beds
  • 2 Baths
  • 2,471 Sq Ft
  • House for Rent

  376 Abbey Rd, Mount Tremper, NY 12457

  Located on one of Woodstock's most desirable roads sits this classic contemporary set on 5 acres. Privately situated on a town-maintained, dead end lane for that ultimate get-away feeling, this light-filled, two bedroom, two bathroom home with additional flex space, features soaring ceilings with solid wood floors, flooded with natural light from floor-to-ceiling windows. The main living area

  Victoria Stent Coldwell Banker Village Green

  376 Abbey Rd, Mount Tremper, NY 12457
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  /34

  $800,000

  Sold Dec 17, 2025

  3251 Route 212, Bearsville, NY 12409

  • 2 Beds
  • 2 Baths
  • 1,850 Sq Ft
  • Built 1925

  Last Sold Summary

  • 3% Above List Price
  • $432/SF
  • 62 Days On Market

  Last Listing Agent Laurie Ylvisaker Coldwell Banker Village Green

  3251 Route 212, Bearsville, NY 12409
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  /32

  Est $934,501

  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
• 

  

  /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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  /34

  $3,500 Per Month

  • 1 Bed
  • 1 Bath
  • 890 Sq Ft
  • House for Rent

  10 Fitzsimmons Ln, Woodstock, NY 12498

  Escape to your own private retreat nestled among mature trees and bordered by a tranquil stream. This unique property offers an extraordinary blend of nature, privacy, and relaxation, creating a setting that feels worlds away from everyday life. Designed with a Zen-inspired aesthetic, the home features a remarkable spa-like bath suite complete with a slate walk-in shower, bamboo accents, river

  Greg Berardi Berardi Realty

  10 Fitzsimmons Ln, Woodstock, NY 12498
• 

  $1,577,000

  Sold Jun 11, 2026

  551 Mount Guardian Rd, Shady, NY 12409

  • 2 Beds
  • 2 Baths
  • 2,308 Sq Ft
  • Built 1983

  Last Sold Summary

  • 1% Above List Price
  • $683/SF
  • 13 Days On Market

  Last Listing Agent Sharon Breslau BHHS Hudson Valley Properties

  551 Mount Guardian Rd, Shady, NY 12409
• 

  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

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