Woodstock, NY Homes

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  /40

  $550,000

  $99K PRICE DROP Pending

  • 3 Beds
  • 2 Baths
  • 1,568 Sq Ft

  5 Streamside Terrace, Woodstock, NY 12498

  Major price reduction. Seller says sell!!Woodstock Village living doesn't get much better than this. Perfectly positioned on a quiet no outlet street just moments from the heart of town, this beautifully renovated three-bedroom, two-bath home offers the rare opportunity to enjoy both nature and village life without compromise.Step inside to bright, sun-filled interiors and an open,

  

  Amy Lonas

  Coldwell Banker Village Green

  5 Streamside Terrace, Woodstock, NY 12498
• Explore Woodstock

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  /11

  $4,200 Per Month

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

  3209 Route 212 Unit 1, Bearsville, NY 12409

  Welcome to the Woodstock Craftsman, a light-filled, fully furnished two bedroom, one bath mountain home nestled on a quiet 1.85-acre compound in the heart of Bearsville. Surrounded by blooming fruit trees, bluestone walkways, and serene views, this sun-drenched residence offers private stream access right across the road and comes complete with both a classic front porch and a private enclosed

  

  Kristen Zigouras

  eXp Realty

  3209 Route 212 Unit 1, Bearsville, NY 12409
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  /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 $840,183

  Last Listing Agent Leslie Foti Coldwell Banker Village Green

  16 Marko Grove, Woodstock, NY 12498
• 

  

  

  /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

  Last Listing Agent Julie Senecal Grist Mill Real Estate
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  /61

  $1,350,000

  Under Contract

  • 4 Beds
  • 3 Baths
  • 2,128 Sq Ft

  1748 Glasco Turnpike, Woodstock, NY 12498

  With nearly 14 acres, a heated saltwater pool, a separate two-bedroom ADU, and a warm character-filled main house, this Woodstock stream side country compound has been reimagined and meticulously updated within the last 5 years from soup to nuts. It is move-in ready as a weekend home, Air B&B or full-time residence. The main residence has the relaxed unpretentious character that makes a house

  

  Amy Lonas

  Coldwell Banker Village Green

  1748 Glasco Turnpike, Woodstock, NY 12498
• 

  

  /15

  $2,100 Per Month

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

  200 Van Dale Rd Unit Retreat, Woodstock, NY 12498

  Property Id: 1792319 Beautiful, quiet, one-bedroom apartment located on a secluded 4 acre lot, only 2 miles from town. Washer/Dryer in the apartment. RENT INCLUDES the following UTILITIES and AMENITIES: ELECTRIC, TRASH, WATER, FUEL OIL, ULTRA HIGH-SPEED WIFI, and STREAMING CONENT. Streaming content paid subscriptions currently include; Disney+, Apple+, Netflix, Amazon Prime, Paramount+,

  200 Van Dale Rd Unit Retreat, 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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  /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

  Last Listing Agent Amy Lonas Coldwell Banker Village Green
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  /59

  $1,375,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,993 Sq Ft

  60 Boggs Hill Rd, Woodstock, NY 12498

  A Rare Byrdcliffe-Era Magical Retreat with Artistic LegacyBuilt in 1905, just as the historic Byrdcliffe Arts Colony and the Art Students League of New York's renowned summer school were taking root, this extraordinary three-bedroom, two-bath, one-of-a-kind residence is a rare architectural treasure deeply woven into Woodstock's creative history.Rich in authenticity and soul, the home

  

  Amy Lonas

  Coldwell Banker Village Green

  60 Boggs Hill Rd, Woodstock, NY 12498
• 

  

  /15

  $2,100

  Total Monthly Price

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

  200 Van Dale Rd Unit Woodstcock 1 Bdm Apt, Woodstock, NY 12498

  Beautiful, quiet, one-bedroom apartment located on a secluded 4 acre lot, only 2 miles from town. Washer/Dryer in the apartment. RENT INCLUDES the following: ELECTRIC, TRASH, WATER, FUEL OIL, ULTRA HIGH-SPEED WIFI, and STREAMING CONENT. Streaming content paid subscriptions currently include; Disney+, Apple+, Netflix, Amazon Prime, Paramount+, Peacock, Hulu, HBOMax, Spotify, ESPN+, NFL+,… and

  200 Van Dale Rd Unit Woodstcock 1 Bdm Apt, 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 $926,485

  Last Listing Agent Judy Steinfeld Halter Associates Realty

  8 Pine Grove St, Woodstock, NY 12498
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  /28

  Est $972,270

  Not Listed For Sale

  390 Coldbrook Rd, Bearsville, NY 12409

  • 3 Beds
  • 2.5 Baths
  • 1,931 Sq Ft
  • Built 2012

  390 Coldbrook Rd, Bearsville, NY 12409

  Last Sold Summary

  • 56 Days On Market

  Last Listing Agent Johanna Trimboli Halter Associates Realty
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  /46

  $695,000

  • 3 Beds
  • 2 Baths
  • 1,842 Sq Ft

  47 van de Bogart Rd, Woodstock, NY 12498

  Set well back from the road and sited on 4+ acres, this wonderful 1935 farmhouse has been updated over the years yet retains its original charm and character. Most recent upgrades within the year include a new kitchen with marble and butcherblock counters, a completely renovated main bathroom, new roof, and more. The grounds are lovely with established perennials, level grassy meadow and woods to

  

  Amy Lonas

  Coldwell Banker Village Green

  47 van de Bogart Rd, Woodstock, NY 12498
• 

  

  /31

  $10,923

  Total Monthly Price

  • 4 Beds
  • 4 Baths
  • 2,798 Sq Ft
  • Condo for Rent

  28 Holiday Dr Unit SI ID1546434P, Woodstock, NY 12498

  The advertised rate of $10,923/month is the lowest available price, based on a 1 month(s) and 2 day(s) stay with a move-in date of February 16, 2027. Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed

  28 Holiday Dr Unit SI ID1546434P, Woodstock, NY 12498
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  /15

  $575,000

  Sold Aug 07, 2026

  501 Ohayo Mountain Rd, Woodstock, NY 12498

  • 3 Beds
  • 1.5 Baths
  • 1,133 Sq Ft
  • Built 1985

  Last Sold Summary

  • 3% Below List Price
  • $508/SF
  • 83 Days On Market

  Current Estimated Value $591,598

  Last Listing Agent James Angelakis BHHS HUDSON VALLEY PROP-WDST

  501 Ohayo Mountain Rd, 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

  Last Listing Agent Toby Ress Win Morrison Realty - W
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  /50

  $1,950,000

  $400K PRICE DROP Pending

  • 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
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  /28

  $5,500 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
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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 $549,376

  Last Listing Agent Fawn Denue Dalton Wade, Inc.

  5 Violet Place, Woodstock, NY 12498
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  /35

  Est $1,254,210

  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

  Last Listing Agent Kelcey Otten Compass Greater NY, LLC
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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
• 

  

  /6

  $2,250 Per Month

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • 5-7 Rock City Road

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

  Beautifully renovated 2-bedroom loft in the heart of Woodstock. Flooded with natural light, pet-friendly, and steps from town, with nearly all utilities included (tenant pays WiFi).Welcome to this completely renovated 2-bedroom, 1-bath apartment at 5 Rock City Road, ideally located in Woodstock. This unit offers a rare combination of modern upgrades, thoughtful design, and move-in-ready

  5-7 Rock City Rd Unit 3A, Woodstock, NY 12498
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  /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 $373,575

  Last Listing Agent Laurie Ylvisaker Coldwell Banker Village Green

  57 Overlook Dr, Woodstock, NY 12498
• 

  

  /22

  Est $487,983

  Not Listed For Sale

  512 Watson Woods, Lake Hill, NY 12448

  • 3 Beds
  • 1 Bath
  • 1,140 Sq Ft
  • Built 1970

  512 Watson Woods, Lake Hill, NY 12448

  Last Sold Summary

  • 55 Days On Market

  Last Listing Agent Megan Rios Berardi Realty
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  /74

  $1,195,000

  • 5 Beds
  • 4 Baths
  • 3,475 Sq Ft

  388-390 Wittenberg Rd, Bearsville, NY 12409

  A rare opportunity just minutes from the heart of historic Woodstock, this exceptional country compound pairs the timeless character of a beautifully updated farmhouse with the privacy and tranquility of an estate-like setting. A long private drive unfolds through peaceful, park-like grounds where meadow, mature woods, gardens, and abundant nature create a remarkable sense of seclusion so close

  Eric Amaral Coldwell Banker Village Green

  388-390 Wittenberg 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
• 

  

  /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
• 

  /2

  Est $704,480

  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
• 

  

  /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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  /8

  $2,300 Per Month

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft
  • 5-7 Rock City Road

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

  Beautifully designed, fully furnished 1-bedroom loft in the heart of Woodstock—flooded with natural light and steps from town, with nearly all utilities included (tenant pays WiFi).Welcome to this completely renovated 1-bedroom, 1-bath apartment at 5 Rock City Road, ideally located in Woodstock. This unit offers a rare combination of modern upgrades, thoughtful design, and true turnkey

  5-7 Rock City Rd Unit 3D, 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
• 

  

  /30

  Est $781,031

  Not Listed For Sale

  86 Baumgarten Rd, Woodstock, NY 12498

  • 2 Beds
  • 2 Baths
  • 2,280 Sq Ft
  • Built 2016

  86 Baumgarten Rd, Woodstock, NY 12498

  Last Sold Summary

  • 105 Days On Market

  Last Listing Agent Baris Demirel Serhant LLC
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  /37

  $699,000

  $50K PRICE DROP

  • 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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  /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 OCT 2026. 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
• 

  

  /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 $401,732

  Last Listing Agent Laura Prince Hudson Dwellings Realty

  38 Arnold Dr, Woodstock, NY 12498
• 

  

  /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

  Last Listing Agent Judy Steinfeld Halter Associates Realty
• 

  

  /37

  $815,000

  Pending

  • 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
• 

  

  /20

  $3,500 Per Month

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Woodstock/Hunter romantic getaway in nature on 3.5 acres

  452 Cold Brook Rd, Bearsville, NY 12409

  Available Immediately.** Vacation rental: available for various length of stays, $4500/month+cleaning $300 or $1200/week + cleaning $150 *** Bright, sweet, serene and also private! Pink House is a lovely 2BR house beauty at its 3.5 acre of greens in scenic nature just minutes to town center of Woodstock and Phoenicia! Close to many historic towns like Kingston, Saugerties, and Hunter ski resort

  452 Cold Brook Rd, Bearsville, NY 12409
• 

  

  /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
• 

  

  /24

  Est $719,018

  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

  Last Listing Agent Richard Vizzini Corcoran Country Living

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