Woodstock, NY Homes

• 

  Est $1,048,284

  Not Listed For Sale

  688 Zena Rd, Woodstock, NY 12498

  • 4 Beds
  • 3.5 Baths
  • 3,554 Sq Ft
  • Built 2004

  688 Zena Rd, Woodstock, NY 12498

  Last Sold Summary

  • 154 Days On Market

  Last Listing Agent Greg Berardi Berardi Realty
• 

  

  

  /50

  $2,399,000

  Pending

  • 4 Beds
  • 4.5 Baths
  • 5,342 Sq Ft

  40 Mount Guardian Rd, Bearsville, NY 12409

  Guardian House is a private mountain retreat set into the wooded hills of Bearsville, designed by renowned Woodstock architect Barry Price and rebuilt in 2011 to live in harmony with its surroundings. Thoughtful, restrained, and deeply connected to the landscape, the home feels both grounded and elevated, a place meant for retreat, reflection, and gathering. Wrapped in forest and framed by long

  STEVEN WROBEL JR. Serhant LLC

  40 Mount Guardian Rd, Bearsville, NY 12409
• 

  

  

  /32

  $600,000

  Sold Apr 21, 2026

  110 Mill Hill Rd, Woodstock, NY 12498

  • 2 Beds
  • 1 Bath
  • 1,783 Sq Ft
  • Built 1951

  Last Sold Summary

  • 3% Above List Price
  • $337/SF
  • 42 Days On Market

  Current Estimated Value $604,206

  Last Listing Agent Karen Sullivan Coldwell Banker Village GreenK

  110 Mill Hill Rd, Woodstock, NY 12498
• 

  

  

  /34

  Est $844,670

  Not Listed For Sale

  252 John Joy Rd, Woodstock, NY 12498

  • 3 Beds
  • 2 Baths
  • 1,875 Sq Ft
  • Built 1988

  252 John Joy Rd, Woodstock, NY 12498

  Last Sold Summary

  • 16 Days On Market

  Last Listing Agent Leslie Foti Coldwell Banker Village Green
• 

  

  

  /21

  $420,000

  Under Contract

  • 1 Bed
  • 2 Baths
  • 1,012 Sq Ft

  121 Tinker St, Woodstock, NY 12498

  Prime Income Property | Woodstock 2-Family Opportunity Savvy investors and owner-occupants, take note. This exceptionally located 2-family property in high-demand Woodstock Hamlet rental market. The Units:The property consists of two highly rentable units. The ground floor unit is one bedroom, one bath in a footprint of 601 square feet. The upstairs unit is an open studio space with bath

  Peter Cantine Halter Associates Realty

  121 Tinker St, Woodstock, NY 12498
• 

  

  /24

  $1,062,000

  Sold Aug 03, 2026

  540 Mount Tobias Rd, Mount Tremper, NY 12457

  • 3 Beds
  • 4 Baths
  • 3,120 Sq Ft
  • Built 2007

  Last Sold Summary

  • 8% Below List Price
  • $340/SF
  • 55 Days On Market

  Last Listing Agent Alexander James Compass Greater NY, LLC

  540 Mount Tobias Rd, Mount Tremper, NY 12457
• 

  

  /33

  Est $1,140,052

  Not Listed For Sale

  9 Fox Hollow Rd, Woodstock, NY 12498

  • 3 Beds
  • 2.5 Baths
  • 2,527 Sq Ft
  • Built 1988

  9 Fox Hollow Rd, Woodstock, NY 12498

  Last Sold Summary

  • 119 Days On Market

  Last Listing Agent Richard Vizzini Corcoran Country Living
• 

  

  /9

  $199,000

  Pending

  • Land
  • 4 Acres
  • $49,750 per Acre

  20 Lion's Way, Woodstock, NY 12409

  Looking for a Unicorn? If you've been searching for a home near the village of Woodstock, with private panoramic mountain views, this may be the parcel for you to build your dream home! This 4 acre lot with beautiful glacial rock outcroppings is perched on the mountain with a nice level area and views in almost every direction and, it has already been rough cleared with a rough driveway as well.

  Mercedes Ross Coldwell Banker Village Green

  20 Lion's Way, Woodstock, NY 12409
• 

  

  /25

  $450,500

  Sold Dec 29, 2025

  44 Overlook Dr, Woodstock, NY 12498

  • 3 Beds
  • 1 Bath
  • 1,164 Sq Ft
  • Built 1956

  Last Sold Summary

  • 10% Below List Price
  • $387/SF
  • 153 Days On Market

  Current Estimated Value $463,498

  Last Listing Agent Jack Yao Realmart Realty, LLC

  44 Overlook Dr, Woodstock, NY 12498
• 

  

  /32

  Est $756,183

  Not Listed For Sale

  229 Chestnut Hill Rd, Woodstock, NY 12498

  • 4 Beds
  • 1 Bath
  • 1,713 Sq Ft
  • Built 1800

  229 Chestnut Hill Rd, Woodstock, NY 12498

  Last Sold Summary

  • 12 Days On Market

  Last Listing Agent Amy Lonas Coldwell Banker Village Green
• 

  

  /44

  $1,325,000

  $250K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,360 Sq Ft

  94 Chestnut Hill Rd, Woodstock, NY 12498

  A rare opportunity to own a truly special piece of the Hudson Valley. Nestled in the heart of Woodstock, NY, this iconic property offers 11.17 breathtaking acres of open meadows and sweeping mountain views that change beautifully with every season. The well-maintained 3-bedroom, 1-bath ranch house spans 1,360 square feet and offers comfortable single-level living with a warm, classic character. A

  Henry Ford Coldwell Banker Village Green

  94 Chestnut Hill Rd, Woodstock, NY 12498
• 

  

  /30

  $480,000

  Sold Feb 20, 2026

  5 Evergreen Ln, Woodstock, NY 12498

  • 2 Beds
  • 2 Baths
  • 1,073 Sq Ft
  • Built 1960

  Last Sold Summary

  • 9% Below List Price
  • $447/SF
  • 73 Days On Market

  Current Estimated Value $498,874

  Last Listing Agent Richard Miller Win Morrison Realty - W

  5 Evergreen Ln, Woodstock, NY 12498
• 

  

  /30

  Est $1,193,371

  Not Listed For Sale

  10 Raybrook Dr, Woodstock, NY 12498

  • 3 Beds
  • 3 Baths
  • 2,150 Sq Ft
  • Built 1989

  10 Raybrook Dr, Woodstock, NY 12498

  Last Sold Summary

  • 14 Days On Market

  Last Listing Agent Danielle Sevier Compass Greater NY, LLC
• 

  

  /19

  $799,000

  $60K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,562 Sq Ft

  2323 Glasco Turnpike, Woodstock, NY 12498

  A rare Byrdcliffe Colony offering, this 1911 Woodstock artist home sits just off Lower Byrdcliffe Road on a private half-acre of garden, lawn, patio, and woods. Rich with history and creative spirit, the original structure features the classic north-facing artist's window designed for painter's light, along with original beams and woodwork that speak to the home's early 20th-century

  Mark Kanter BHHS HUDSON VALLEY PROP-WDST

  2323 Glasco Turnpike, Woodstock, NY 12498
• 

  

  /29

  $475,000

  Sold May 20, 2026

  2 Fern Hollow, Woodstock, NY 12498

  • 2 Beds
  • 1 Bath
  • 1,263 Sq Ft
  • Built 1950

  Last Sold Summary

  • 13% Below List Price
  • $376/SF
  • 209 Days On Market

  Current Estimated Value $487,333

  Last Listing Agent Christine Chapman Chapman Realty of the Hudson V

  2 Fern Hollow, Woodstock, NY 12498
• 

  

  /30

  Est $1,160,665

  Not Listed For Sale

  19 Wilber Ln, Woodstock, NY 12498

  • 3 Beds
  • 2 Baths
  • 2,300 Sq Ft
  • Built 1940

  19 Wilber Ln, Woodstock, NY 12498

  Last Sold Summary

  • 8 Days On Market

  Last Listing Agent Quinn Hagstrand BHHS HUDSON VALLEY PROP-WDST
• 

  

  /30

  $898,000

  $81K PRICE DROP Pending

  • 2 Beds
  • 2 Baths
  • 900 Sq Ft

  14 Old Forge Rd, Woodstock, NY 12498

  PROPERTY HIGHLIGHTS. Big ''Tiny House'': Designed for people who love Small Efficient Spaces, by the Water, with Mountain Views, enjoy living ''uncarred'', in the most Central Location in Woodstock. Layout: 2 bedrooms and 2 bathrooms. Exceptionally rare Climate Resilient Construction featuring Steel floor and ceiling joists with comprehensive Energy Efficient Upgrades throughout. INTERIOR

  Danielle Sevier Compass Greater NY, LLC

  14 Old Forge Rd, Woodstock, NY 12498
• 

  

  /37

  $745,000

  Sold Aug 13, 2025

  2366 Glasco Turnpike, Woodstock, NY 12498

  • 4 Beds
  • 2 Baths
  • 1,498 Sq Ft
  • Built 1922

  Last Sold Summary

  • 10% Below List Price
  • $497/SF
  • 86 Days On Market

  Current Estimated Value $772,292

  Last Listing Agent Margo Obourn Win Morrison Realty - W

  2366 Glasco Turnpike, Woodstock, NY 12498
• 

  

  /44

  Est $956,858

  Not Listed For Sale

  14 Wardwell Ln, Woodstock, NY 12498

  • 4 Beds
  • 2.5 Baths
  • 2,264 Sq Ft
  • Built 1978

  14 Wardwell Ln, Woodstock, NY 12498

  Last Sold Summary

  • 35 Days On Market

  Last Listing Agent Stacey Anderson BHHS HUDSON VALLEY PROP-WDST
• 

  

  /56

  $850,000

  • 2 Beds
  • 3.5 Baths
  • 3,256 Sq Ft

  95 W Saugerties Woodstock Rd, Woodstock, NY 12498

  An Energy-efficient home!Driven by a 13W solar array, airtight insulation and smart power management ,this south facing home offsets all current electrical usage with an energy-positive footprint. Included is an EV charging station used for 2 cars. Discover this Woodstock home which offers privacy and convenience. This rare property sits nestled at the end of a long, winding driveway,

  Carol Spirig Halter Associates Realty

  95 W Saugerties Woodstock Rd, Woodstock, NY 12498
• 

  

  /22

  $425,000

  Sold Sep 03, 2025

  512 Watson Woods, Lake Hill, NY 12448

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

  Last Sold Summary

  • 6% Below List Price
  • $373/SF
  • 55 Days On Market

  Current Estimated Value $495,965

  Last Listing Agent Megan Rios Berardi Realty

  512 Watson Woods, Lake Hill, NY 12448
• 

  

  /31

  Est $943,726

  Not Listed For Sale

  2492 Route 212, Woodstock, NY 12498

  • 4 Beds
  • 4 Baths
  • 2,216 Sq Ft
  • Built 1986

  2492 Route 212, Woodstock, NY 12498

  Last Sold Summary

  • 105 Days On Market

  Last Listing Agent Leslie Foti Coldwell Banker Village Green
• 

  

  /36

  $785,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,494 Sq Ft

  168 Jessop Rd, Willow, NY 12495

  Nestled in a storybook setting, this enchanting residence is embraced by a natural tapestry of mature trees and exquisite landscaping. Situated on Jessop Road, a peaceful dead-end lane, it offers the ultimate privacy and seclusion--an idyllic retreat perfectly nestled in the mountains. Immaculately maintained over the years, this home exudes timeless charm and quaint elegance. ''Romantic'' is the

  Danielle Marchisella Corcoran Country Living

  168 Jessop Rd, Willow, NY 12495
• 

  

  /30

  $2,675,000

  Sold Jun 26, 2026

  0 Wittenberg Rd Unit 20252191, Woodstock, NY 12498

  • 9 Beds
  • 10 Baths
  • 8,452 Sq Ft
  • Built 1929

  Last Sold Summary

  • 27% Above List Price
  • $316/SF
  • 286 Days On Market

  Last Listing Agent Nancy Felcetto Brown Harris Stevens Hudson

  0 Wittenberg Rd Unit 20252191, Woodstock, NY 12498
• 

  

  /40

  Est $555,909

  Not Listed For Sale

  1979 Glasco Turnpike, Woodstock, NY 12498

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • Built 1930

  1979 Glasco Turnpike, Woodstock, NY 12498

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Maria Gianas The Machree Group, LLC
• 

  

  /33

  $569,000

  $30K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,300 Sq Ft

  328 John Joy Rd, Woodstock, NY 12498

  Nearly Six Lush, Scenic And Private Acres Located Eight Minutes From The Heart Of Woodstock! This Home Features Two / Possibly Three Bedrooms And Two Full Baths. Meticulously Maintained! Enjoy Sunrises Or Sunsets From The Wrap Around Deck. Relax And Take In All Of The Tranquility While Sitting Stream Side Or Enjoy The Changing Of The Leaves During The Beautiful Fall Season While Sipping Hot Cocoa

  Michael Alpert Daniel Gale Sothebys Intl Rlty

  328 John Joy Rd, Woodstock, NY 12498
• 

  

  /31

  $975,000

  Sold May 26, 2026

  33 Tannery Brook Rd, Woodstock, NY 12498

  • 4 Beds
  • 4 Baths
  • 1,811 Sq Ft
  • Built 1870

  Last Sold Summary

  • $538/SF
  • 32 Days On Market

  Current Estimated Value $975,812

  Last Listing Agent Danielle Sevier Compass Greater NY, LLC

  33 Tannery Brook Rd, Woodstock, NY 12498
• 

  

  /35

  Est $571,925

  Not Listed For Sale

  1800 Glasco Turnpike, Woodstock, NY 12498

  • 3 Beds
  • 1 Bath
  • 1,672 Sq Ft
  • Built 1984

  1800 Glasco Turnpike, Woodstock, NY 12498

  Last Sold Summary

  • 34 Days On Market

  Last Listing Agent Gail Cadden Coldwell Banker Village Green
• 

  

  /33

  $495,000

  • Land
  • 5 Acres
  • $99,000 per Acre

  0 Yerry Hill-Lot 2 Rd Unit 20263990, Woodstock, NY 12498

  Tucked away just minutes from the heart of Woodstock, this exceptional 5-acre parcel offers a rare opportunity to create something truly special in one of the Hudson Valley's most sought-after locations. Surrounded by mature woods and natural beauty, the property features the serene Little Beaver Kill winding through the land along with seasonal mountain views from the upper elevation, creating

  Eliana Amodio Amodio Real Estate & Prop

  0 Yerry Hill-Lot 2 Rd Unit 20263990, Woodstock, NY 12498
• 

  $515,000

  Sold Mar 09, 2026

  36-38 Ohayo Mountain Rd, Woodstock, NY 12498

  • 4 Beds
  • 3 Baths
  • 2,208 Sq Ft
  • Built 1925

  Last Sold Summary

  • 30% Below List Price
  • $233/SF
  • 123 Days On Market

  Last Listing Agent Sheena Lepez Compass Greater NY, LLC

  36-38 Ohayo Mountain Rd, Woodstock, NY 12498
• 

  

  /38

  Est $960,295

  Not Listed For Sale

  1964 Glasco Turnpike, Woodstock, NY 12498

  • 4 Beds
  • 3 Baths
  • 2,219 Sq Ft
  • Built 1973

  1964 Glasco Turnpike, Woodstock, NY 12498

  Last Sold Summary

  • 31 Days On Market

  Last Listing Agent Laurie Ylvisaker Coldwell Banker Village Green
• 

  

  /28

  $799,999

  Pending

  • 3 Beds
  • 2.5 Baths
  • 2,924 Sq Ft

  30 Whitney Dr, Woodstock, NY 12498

  The moment you turn onto the long private drive, something shifts. The world quietly falls away, and by the time you arrive at this exceptional 3-bedroom, 2.5-bath colonial, you already know this is different. Set on 3.35 wooded acres just minutes from the cultural heart of Woodstock, this is move-in luxury with genuine soul. The first-floor primary suite is the story within the story. A generous

  Amy McArdle eXp Realty

  30 Whitney Dr, Woodstock, NY 12498
• 

  

  /47

  $1,200,000

  Sold Dec 11, 2025

  11 Grog Kill Rd, Willow, NY 12495

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

  Last Sold Summary

  • 14% Below List Price
  • $390/SF
  • 77 Days On Market

  Current Estimated Value $1,102,555

  Last Listing Agent Sharon Breslau BHHS HUDSON VALLEY PROP-WDST

  11 Grog Kill Rd, Willow, NY 12495
• 

  

  /29

  Est $924,380

  Not Listed For Sale

  33 Maurizi Ln, Woodstock, NY 12498

  • 3 Beds
  • 4 Baths
  • 3,820 Sq Ft
  • Built 1992

  33 Maurizi Ln, Woodstock, NY 12498

  Last Sold Summary

  • 213 Days On Market

  Last Listing Agent Dana Matthews Rouse + Co Real Estate
• 

  

  /29

  $599,000

  $19K PRICE INCREASE

  • 3 Beds
  • 3 Baths
  • 1,824 Sq Ft

  171 Van Dale Rd, Woodstock, NY 12498

  Step into this meticulously maintained and tastefully updated Woodstock split-level. Set way back from the road on one beautifully landscaped acre, featuring stately mature shade trees, ornamental shrubs, huge rhododendrons and plenty of sun. The main living level has been renovated to create a new, more modern great room. The dinning room and living room flow seamlessly into a lovely, eat-in

  Brian Cafferty Halter Associates Realty

  171 Van Dale Rd, Woodstock, NY 12498
• 

  

  /31

  $785,000

  Sold Feb 20, 2026

  11 Forestwood Dr, Woodstock, NY 12498

  • 3 Beds
  • 2.5 Baths
  • 2,316 Sq Ft
  • Built 1966

  Last Sold Summary

  • 2% Below List Price
  • $339/SF
  • 44 Days On Market

  Current Estimated Value $796,287

  Last Listing Agent Laurie Ylvisaker Coldwell Banker Village Green

  11 Forestwood Dr, Woodstock, NY 12498
• 

  

  /35

  Est $714,818

  Not Listed For Sale

  23 Maurizi Ln, Woodstock, NY 12498

  • 4 Beds
  • 2.5 Baths
  • 2,320 Sq Ft
  • Built 1972

  23 Maurizi Ln, Woodstock, NY 12498

  Last Sold Summary

  • 29 Days On Market

  Last Listing Agent Melissa Mayes Serhant LLC
• 

  

  /42

  $799,900

  $195K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,316 Sq Ft

  5 Maverick Terrace, Woodstock, NY 12498

  Tucked away on a peaceful, wooded lane, this inviting home offers the perfect blend of privacy, space, and convenience- just minutes to the heart of Woodstock. Inside, the home opens to an expansive living room anchored by a beautiful brick fireplace, creating a warm and inviting centerpiece for gatherings or quiet evenings. This oversized space includes a full bathroom and flows effortlessly to

  Dominique Musialkiewicz Howard Hanna Rand Realty

  5 Maverick Terrace, Woodstock, NY 12498
• 

  

  /22

  $425,000

  Sold Apr 14, 2026

  3271 Route 212, Bearsville, NY 12409

  • 4 Beds
  • 2 Baths
  • 1,792 Sq Ft
  • Built 1923

  Last Sold Summary

  • 9% Below List Price
  • $237/SF
  • 57 Days On Market

  Current Estimated Value $429,086

  Last Listing Agent Pieta Williams Halter Associates Realty

  3271 Route 212, Bearsville, NY 12409
• 

  

  /29

  Est $683,687

  Not Listed For Sale

  14 Maurizi Ln, Woodstock, NY 12498

  • 4 Beds
  • 4 Baths
  • 2,481 Sq Ft
  • Built 1971

  14 Maurizi Ln, Woodstock, NY 12498

  Last Sold Summary

  • 66 Days On Market

  Last Listing Agent Laura Warren Coldwell Banker Village Green

Showing Results 201 - 240, Page 6 of 18